- Antiacetylcholinesterase triterpenes from the fruits of: Cimicifuga yunnanensis
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Two new cycloartane triterpenes, cimyunnin E (1), containing a unique oxaspiro[4.4]nonanedione moiety based on rings D and E, together with cimicifine B (2), a 25,26,27-trinortriterpene featuring a pyridine ring E, were purified from the fruits of Cimicifuga yunnanensis. Their structures were elucidated by spectroscopic methods and ECD (electronic circular dichroism calculations). Compounds 1 and 2 showed significant acetylcholinesterase (AChE) inhibition with IC50 values of 1.58 and 3.87 μM, respectively. In addition, they noticeably enhanced the neurite outgrowth of nerve growth factor (NGF) mediated PC12 cells at a concentration of 10 μM.
- Nian, Yin,Lu, Ni-Hong,Liu, Xiao-Ling,Li, Da-Shan,Zhou, Lin,Qiu, Ming-Hua
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- Exceptionally high yields of furfural from assorted raw biomass over solid acids
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Development of stable and recyclable solid acid catalysts in the efficient valorisation of hemicellulose to yield C5 sugars and furfural is vital to boost the prospects of using lignocelluloses for chemicals synthesis. Using an silicoaluminopho
- Bhaumik, Prasenjit,Dhepe, Paresh Laxmikant
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- LC-MS- and 1H NMR Spectroscopy-Guided Identification of Antifungal Diterpenoids from Sagittaria latifolia
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Antifungal screening of small-molecule natural product libraries showed that a column fraction (CF) derived from the plant extract of Sagittaria latifolia was active against the fungal pathogen Cryptococcus neoformans. Dereplication analysis by liquid chromatography-mass spectrometry (LC-MS) and proton nuclear magnetic resonance spectroscopy (1H NMR) indicated the presence of new compounds in this CF. Subsequent fractionation of the plant extract resulted in the identification of two new isopimaradiene-type diterpenoids, 1 and 2. The structures of 1 and 2 were determined by chemical methods and spectroscopic analysis as isopimara-7,15-dien-19-ol 19-O-α-l-arabinofuranoside and isopimara-7,15-dien-19-ol 19-O-α-l-(5′-acetoxy)arabinofuranoside, respectively. Compound 1 exhibited IC50 values of 3.7 and 1.8 μg/mL, respectively, against C. neoformans and C. gattii. Its aglycone, isopimara-7,15-dien-19-ol (3), resulting from acid hydrolysis of 1, was also active against the two fungal pathogens, with IC50 values of 9.2 and 6.8 μg/mL, respectively. This study demonstrates that utilization of the combined LC-MS and 1H NMR analytical tools is an improved chemical screening approach for hit prioritization in natural product drug discovery.
- Ravu, Ranga Rao,Jacob, Melissa R.,Jeffries, Cynthia,Tu, Ying,Khan, Shabana I.,Agarwal, Ameeta K.,Guy, R. Kiplin,Walker, Larry A.,Clark, Alice M.,Li, Xing-Cong
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- Triterpenes from the aerial parts of Cimicifuga yunnanensis and their antiproliferative effects on p53N236S mouse embryonic fibroblasts
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Nine new triterpene derivatives, yunnanterpenes A-F (1-6), 15,16-seco-cimiterpenes A and B (7, 8), and cimilactone C (9), and 15 known analogues (10-24) were isolated from the aerial parts of Cimicifuga yunnanensis. The new structures were established using a combination of MS, NMR, and single-crystal X-ray diffraction techniques. WT MEFs (wild-type mouse embryonic fibroblasts) and tumorigenic cell lines p53-/-+H-RasV12 and p53 -/-+p53N236S+H-RasV12 were used for evaluating active structures, targeting p53N236S (corresponding to p53N239S in humans) mutation. Compound 5 showed nonselective activities against these cell lines, with IC50 values of 5.8, 8.6, and 6.0 μM, respectively. Compound 4 exhibited greater selectivity against the p53 -/-+p53N236S+H-RasV12 cells (IC50 5.5 μM) than against the WT MEFs cells (IC50 14.3 μM).
- Nian, Yin,Zhu, Hui,Tang, Wen-Ru,Luo, Yin,Du, Jiang,Qiu, Ming-Hua
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- Three new benzophenone glycosides with MAO-A inhibitory activity from Hypericum thasium Griseb.
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Purification of n-BuOH fraction from 80% ethanol extract of Hypericum thasium Griseb. resulted in the isolation of three new compounds 3′,4,5′-trihydroxy-6-methoxy-2-O-α-l-arabinosylbenzophenone (1), 3′,4,5′,6-tetrahydroxy-2-O-α-l-arabinosylbenzophenone (2), and 3′,4-dihydroxy-5′-methoxy-2-O-α-l-arabinosyl-6-O- β-d-xylosylbenzophenone (3) along with a known flavonoid glycoside quercetin-3-O-α-l-arabinofuranoside (4). The structures of the new compounds were elucidated by 1D and 2D NMR analysis as well as HRESIMS. The isolated compounds (1-4), as well as quercetin, and kaempferol previously isolated from EtOAc fraction were screened against MAO-A inhibitory activity. When tested against the MAO-A quercetin and kaempferol displayed IC50 values of 19.6, and 17.5 μM, respectively. The IC50 values for MAO-A inhibition by compounds (1-4) were 310.3, 111.2, 726.0, and 534.1 μM, respectively. Standard inhibitor (clorgyline) exhibited MAO-A inhibition with an IC50 value of 0.5 μM.
- Demirkiran, Ozlem
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- Bruceadysentoside A, a new pregnane glycoside and others secondary metabolites with cytotoxic activity from brucea antidysenterica J. F. Mill. (simaroubaceae)
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The chemical investigation of the root barks leaves and stem barks of Brucea antidysenterica J. F. Mill. (Simaroubaceae) led to the isolation of a new pregnane glycoside, named Bruceadysentoside A or 3-O-β-L-arabinopyranosyl-pregn-5-en-20-one (1) together with seventeen known compounds. Their structures were established from spectral data, mainly HRESIMS, 1D and 2D NMR and by comparison with literature data. Compounds 1, 2, 5, 6, 8, 10, 12 and 13 were tested in vitro for their effects on the viability of two different human cancer cell lines, namely prostate PC-3 adenocarcinoma cells and colorectal HT-29 adenocarcinoma cells. No substantial activities were recorded for 2, 10, 12 and 13 (up to 10 μM concentration). 1, 5 and 8 did not show strong anti-proliferative effects up to 100 μM, however, 6 exhibited a stronger anti-proliferative effect with IC50 values of ～ 100 μM against PC-3 and ～ 200 μM against HT-29.
- Makong, Yves Salomon,Fotso, Ghislain Wabo,Mouthe, Gervais Happi,Lenta, Bruno,Rennert, Robert,Sewald, Norbert,Arnold, Norbert,Wansi, Jean Duplex,Ngadjui, Bonaventure Tchaleu
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- A SPIROSTANOL GLYCOSIDE FROM AERIAL PARTS OF DIOSCOREA TENUIPES
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A new spirostanol glycoside isolated from aerial parts of Dioscorea tenuipes was characterized as 5β,25-L-spirostan-1β,2β,3α,4β-tetrol (1β-hydroxydiotigenin or 4β-hydroxyneotokorogenin) 1-O-α-L-arabinopyranoside on the basis of chemical and 1H NMR spectral data. - Key Word Index: Dioscorea tenuipes; Dioscoreaceae; structure determination; 1H NMR; spirostan-tetrol glycoside; 1β-hydroxydiotigenin 1-O-arabinoside.
- Kiyosawa, Shiu,Goto, Katsumi,Sakamoto, Kenji,Kawasaki, Toshio
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- POLYSACCHARIDES FROM THE INFLORESCENCES OF Matricaria matricarioides
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Fractionation of the polysaccharide complex of the inflorescences of pineapple weed has given a galacturonan and a pectic acid.The structures of the galacturonan and pectic acid have been studied by the methods of enzymatic hydrolysis, periodate oxidation, and exhaustive methylation.It has been established that the galacturonan is a linear polysaccharide consisting of D-galacturonic acid residues in the pyranose form with α-1->4-bonds.The main polysaccharide chain of the pectic acid consists of D-galacturonic acid residues in the pyranose form, D-galactose, L-arabinose, and D-xylose residues are covalently bound to carbon atoms 2 or 3 of the main chain of the polysaccharide.
- Yakovlev, A. I.,Shmyreva, E. N.
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- Two new oleanane-type saponins from Elaeocarpus hainanensis Oliv. growing in Vietnam
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Two new oleanane-type saponins, 1α-hydroxy-olean-12-en-3-O-β-D-xylopyranoside (1) and 1α-hydroxy-olean-12-en-3-O-α-L-arabinopyranoside (2), along with six known compounds (3-8), were isolated from the leaves and twigs of Elaeocarpus hainanensis Oliv. Their structures were determined based on chemical and spectroscopic analyses. This is the first report on oleanane-type triterpenoids in the genus Elaeocarpus.
- Nga, Dao Thu,Duong, Pham Quang,Le Dang, Quang,Tung, Nguyen Huu,Hoang, Vu Dinh
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- MK800-62F1, a new inhibitor of apoptotic cell death, from Streptomyces diastatochromogenes MK800-62F1. II. Structure elucidation
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A new compound, MK800-62F1, was isolated from a cultured broth of Streptomyces diastatochromogenes MK800-62F1. The structure was determined by NMR analysis and degradation experiments.
- Yoshimoto, Yuya,Sawa, Tsutomu,Naganawa, Hiroshi,Sugai, Takeshi,Takeuchi, Tomio,Imoto, Masaya
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- Structural characterization and antioxidant activity of a novel heteropolysaccharide from the submerged fermentation mycelia of Ganoderma capense
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A novel heteropolysaccharide (GCPB-2) with a molecular mass of 1.03 × 105 Da was isolated from the submerged fermentation culturing mycelia powder of Lingzhi, Ganoderma capense, by DEAE-52 cellulose, DEAE Sepharose CL-6B, and Sephadex G-75 column chromatography. Its chemical structure was characterized for the first time. The antioxidant activity was evaluated by two antioxidant assay methods. The result of this study introduced G. capense as a possible valuable source that helped to exhibit some antioxidant properties. The homogeneous polysaccharide was composed of xylose and arabinose in the molar ratio of 1:1, and showed a specific optical rotation of [α]D25 = +161° (c 1.0, H2O). Monosaccharide analysis, partial acid hydrolysis, periodic acid oxidation, methylation analysis, gas chromatography-mass spectrometry (GC-MS), Fourier transform-infrared spectroscopy (FT-IR), and nuclear magnetic resonance (NMR) spectroscopy (1H, 13C, HMQC and HMBC) were conducted to elucidate its structure. The backbone of GCPB-2 was composed of (1 → 4)-linked-β-d-xylopyranose residues which branched at O-3. The two branches consisted of (1 → 3)-linked-β-l-arabinopyranose terminated with β-d-xylopyranose residues, and (1 → 4)-linked-β-l-arabinopyranose terminated with β-d-arabinopyranose residues. In the in vitro antioxidant assay, GCPB-2 was found to possess 1-diphenyl-2-picryl-hydrazyl (DPPH) radical-scavenging activity with an EC50 value of 0.379 μM. The findings of this study indicated that GCPB-2 possesses the hydroxyl radical-scavenging activity, which provided an experimental evidence to support the G. capense as functional foods in some Asian countries. To understand better the bioactivity of GCPB-2, the antioxidant activity should be further investigated to find out its mechanism in future work.
- Huang, Yating,Li, Naisheng,Wan, Jian-Bo,Zhang, Dezhi,Yan, Chunyan
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- Two new triterpenoid saponins: telephiifoliosides A and B from the roots of Corrigiola litoralis subsp. telephiifolia (Pourr.) Briq
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The polar fraction of the MeOH extract of the roots of Corrigiola litoralis subsp. telephiifolia (Pourr.) Briq. (Caryophyllaceae) was investigated for its constituents and two previously unreported monodesmosides triterpene saponins, telephiifoliosides A and B (1 and 2), along with the known bonushenricoside A (3) were isolated. Their structures were elucidated by combined spectroscopic and spectrometric techniques (1H NMR, 13C NMR, HSQC, 1H-1H COSY, HMBC, TOCSY, NOESY, HRESIMS) and chemical methods. The structures of the new saponins were established as; 3-O-α-L-arabinopyranosyljaligonic acid (1), and 3-O-α-L-arabinopyranosylphytolaccagenin ester (2). Upon evaluation of the antiproliferative activity on human malignant epithelial (HeLa) cells, none of the isolated compounds was efficient at the concentration of 33 μM. Highlights This is the first phytochemical study on Corrigiola litoralis subsp. telephiifolia. Two new saponins were isolated from the roots of Corrigiola litoralis subsp. telephiifolia. The isolated compounds were tested for their antiproliferative activity.
- Fouedjou, Romuald Tématio,Ponou, Beaudelaire Kemvoufo,Teponno, Rémy Bertrand,Melzig, Matthias,Tanaka, Chiaki,Miyamoto, Tomofumi,Tapondjou, Léon Azefack
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- New lupane-type and ursane-type triterpene saponins from the leaves of Trevesia palmata
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Three new triterpene saponins including two lupane-types and an ursane-type were isolated from the leaves of Trevesia palmata. Their structures were determined as 2α,3β,23-trihydroxylup-20(29)-en-28-oic acid 3-O-α-L-arabinopyranoside (1), 2α,3β,23-trihydroxylup-20(29)-en-28-oic acid 3-O-[α-L-arabinopyranoside]-28-O-[β-D-glucopyranosyl] ester (2), and 2α,3β,23-trihydroxyurs-12-en-28-oic acid 3-O-[α-L-arabinopyranoside]-28-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl] ester (3) by analysis of their HR-ESI-MS, 1D and 2D NMR spectra. The 2α,3β,23-trioxygenated pentacyclic triterpenes were uncommonly found in the nature. At concentration of 100 μM, compounds 1–3 inhibited NO production in LPS activated BV2 cells with inhibitory rates of 17.4 ± 1.8%, 33.1 ± 1.2%, and 11.7 ± 2.2%, respectively. But, they did not significantly inhibit yeast α-glucosidase activity.
- Yen, Pham Hai,Doan, Vu Van,Lien, Giang Thi Kim,Chuong, Nguyen Th? Hong,Thanh, Nguyen Thi Viet,Trang, Do Thi,Dung, Duong Thi,Nhiem, Nguyen Xuan,Tai, Bui Huu,Minh, Chau Van,Kiem, Phan Van
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p. 3285 - 3292
(2019/12/11)
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- Triterpenoid glycosides from the rhizomes of Allium ascalonicum and their anoctamin-1 inhibitory activity
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Ten triterpenoid glycosides including two undescribed compounds (1 and 2) were isolated from the methanol extract of Allium ascalonicum rhizomes. These compounds were structurally elucidated to be 3β-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-19α-hydroxyolean-12-ene-28-oic acid 28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl] ester (1), 3-O-β-D-glucopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl-3β,19α-dihydroxyoleanane-12-en-28-oic acid (2), lactifoloside C (3), lactifoloside H (4), randiasaponin IV (5), kudinoside G (6), ilexkudinoside W (7), lactifoloside G (8), kudinoside D (9), and ilexkudinoside T (10) by analyzing their HR-ESI-MS, NMR spectral data and by comparison with those reported in the literature. Compounds 1–10 were evaluated for anoctamin-1 (ANO1) inhibitory activity using yellow fluorescent protein reduction assays. At the concentration of 30 μM, compounds 2 and 9 displayed moderate ANO1 inhibitory percentages of 28.9 ± 0.85% and 26.2 ± 0.65%, respectively.
- Mai, Nguyen Thi,Dung, Duong Thi,Nga, Tran Thuy,Xuan, Vu Thi,Doan, Vu Van,Tai, Bui Huu,Nhiem, Nguyen Xuan,Yen, Pham Hai,Kiem, Phan Van,Seo, Yohan,Namkung, Wan,Park, SeonJu,Kim, Seung Hyun
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p. 4338 - 4346
(2020/01/31)
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- A novel low-molecular-mass pumpkin polysaccharide: Structural characterization, antioxidant activity, and hypoglycemic potential
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The novel natural low-molecular-mass polysaccharide (SLWPP-3) from pumpkin (Cucurbia moschata) was separated from the waste supernatant after macromolecular polysaccharide production and purified using a DEAE cellulose-52 column and gel-filtration chromatography. Chemical and instrumental studies revealed that SLWPP-3 with a molecular mass of 3.5 kDa was composed of rhamnose, glucose, arabinose, galactose and uronic acid with a weight ratio of 1: 1: 4: 6: 15, and primarily contained →3,6)-β-D-Galp-(1→, →4)-α-GalpA-(1→(OMe), →4)-α-GalpA-(1→, →2,4)-α-D-Rhap-(1→, →3)-β-D-Galp-(1→, →4)-α-D-Glcp, and →4)-β-D-Galp residues in the backbone. The branch chain passes were connected to the main chain through the O-4 atom of glucose and O-3 atom of arabinose. Physiologically, the ability of SLWPP-3 to inhibit carbohydrate-digesting enzymes and DPPH and ABTS radicals, as well as protect pancreatic β cells from oxidative damage by decreasing MDA levels and increasing SOD activities, was confirmed. The findings elucidated the structural types of pumpkin polysaccharides and revealed a potential adjuvant natural product with hypoglycemic effects.
- Huang, Linlin,Li, Fei,Li, Quanhong,Liang, Li,Wei, Yunlu,Yu, Guoyong
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- Cytotoxic triterpenoid saponins from Thalictrum atriplex
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Two new cycloartane glycosides, cycloatriosides A and B (1–2), and a new oleanolic acid glycoside, thaliatrioside A (3), along with 7 known triterpenoids (4–10) were isolated from Thalictrum atriplex. The structures of the new compounds were established as 3-O-β-D-galactopyranosyl (20S, 24 R)-3β,16β,25,29-tetrahydroxy-20,24-epoxycycloartane-29-O-β-D-glucopyranoside (1), 3-O-β-D-glucopyranosyl-(1→2)-α-arabinopyranosyl-3β,22ξ,30-trihydroxycycloart-24-en-21-oic acid α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (2) and 3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl]-oleanolic acid 28-O-β-D-glucopyranosyl ester (3) on the basis of extensive NMR and HR-ESI-MS analyses, along with acid hydrolysis. Their cytotoxic activities against human lung cancer cells A549 and human breast cancer cells MDA-MB-231 were evaluated using MTT method. Compound 9 showed cytotoxicity against MDA-MB-231 cell line with the IC50 value of 72.53 ± 1.08 μM.
- Meng, FanCheng,Wei, XiaoDong,Sun, Yan,Zeng, QingHong,Wang, Guowei,Lan, XiaoZhong,Liao, ZhiHua,Chen, Min
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p. 5757 - 5764
(2020/10/20)
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- New dammarane-type glycosides from Gynostemma pentaphyllum and their lipid-lowering activity
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Gynostemma pentaphyllum (Thunb.) Makino has a long history as food and diary supplement in China. At present, there are some products for hyperlipidemia in the market, including G. pentaphyllum tea, healthy wine and healthy food. In order to discover proprotein convertase subtilisin/kexin type 9 (PCSK9) inhibitors, fourteen new triterpenoid saponins named gypenoside LXXXVIII-CI (1–14) along with six known compounds (15–20) were isolated from G. pentaphyllum. Their structures were elucidated by means of various spectroscopic techniques. Eight isolates were evaluated the inhibitory effect on PCSK9 in HepG2 cells. The results showed that three dammarane-type glycosides (2, 3, 15) remarkably reduced PCSK9 expression at 10 μM concentration. These findings suggested that G. pentaphyllum was worthy of further investigation to find small molecule PCSK9 inhibitors and facilitate their utilization as functional food ingredients.
- Weng, Xin,Lou, Yun-Yun,Wang, Yun-Shan,Huang, Ya-Ping,Zhang, Jian,Yin, Zhi-Qi,Pan, Ke
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- Two new triterpenoid glycosides from leaves of Cyclocarya paliurus
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Two dammarane glycosides (1-2) were isolated from the leaves of Cyclocarya paliurus. The structures of new compounds were established by application of spectroscopic methods, including one-dimensional and two-dimensional NMR, HRESIMS, and chemical hydroly
- Chang, Xiwen,Chen, Huiyun,Gui, Rui,He, Xiaoai,Li, Guihua,Liu, Yiqian,Lu, Shijuan,Ou, Saiyu,Shangguan, Dangang,Sun, Huihui,Wang, Yuyan,Wu, Jianping,Xu, Kangping,Zha, Wenwen,Zhu, Hui
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- α-Glucosidase inhibitory and anti-inflammatory activities of dammarane triterpenoids from the leaves of Cyclocarya paliurus
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Diabetes mellitus is caused by chronic inflammation and affects millions of people worldwide. Cyclocarya paliurus leaves have been widely used in traditional folk tea as a remedy for diabetes, but the antidiabetic constituents remain to be further studied. The α-glucosidase inhibitory and anti-inflammatory activities were examined to evaluate their effects on diabetes mellitus, and bioassay-guided separation of C. paliurus leaves led to the identification of twenty dammarane saponins, including eleven new dammarane saponins (1–11). The structures of the isolates were elucidated by spectroscopic methods. Bioactivity assay results showed that compounds 1 and 2 strongly inhibited α-glucosidase activity, with IC50 values ranging from 257.74 μM, 282.23 μM, and strongly inhibited the release of NO, with IC50 values of 9.10 μM, 9.02 μM. Moreover, compound 2 significantly downregulated the mRNA expression of iNOS, COX-2, IL-1β, NF-κB, IL-6 and TNF-α in LPS-mediated RAW 264.7 cells and markedly suppressed the protein expression of iNOS, NF-κB/p65, and COX-2. Dammarane glucoside 2 exhibited the strongest α-glucosidase inhibitory and anti-inflammatory activities. In addition, the structure–activity relationships (SARs) of the dammarane saponins were investigated. In summary, C. paliurus leaves showed marked α-glucosidase inhibitory and anti-inflammatory activities, and dammarane saponins are responsible for regulating α-glucosidase, inflammatory mediators, and mRNA and the protein expression of proinflammatory cytokines, which could be meaningful for discovering new antidiabetic agents.
- Deng, Shengping,Hao, Lili,Huang, Xishan,Huang, Yan,Li, Chenguo,Li, Jun,Liang, Cheng-qin,Liu, Wei,Su, Shanshan,Xu, Xia,Yang, Ruiyun,Zhang, Gaorong,Zhou, Dexiong
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supporting information
(2021/07/22)
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- Protective effects of four new saponins from Gynostemma pentaphyllum against hydrogen peroxide-induced neurotoxicity in SH-SY5Y cells
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Gynostemma pentaphyllum has been used as a medicine-food homologious health product in China for a long time. This research aimed to isolate and identify its active compounds with protective effects against hydrogen peroxide induced SH-SY5Y cell death. Four new dammarane-type saponins were isolated from G. pentaphyllum using various chromatographic methods. They were identified as gypenoside S1 (1), gypenoside S3 (2), gypenoside S2 (3) and gypenoside S4 (4), respectively by HRESIMS and NMR spectra. Their cytotoxic activity was evaluated against three human cancer cell lines, A549 (lung), HepG2 (liver), SH-SY5Y (nerve), by MTT method. They showed low cytotoxicities with the IC50 values of more than 100 μM on three cancer cell lines. However, they appeared protective effects against hydrogen peroxide induced SH-SY5Y cell death in a dose-dependent manner. They recovered cell viability more than 69% at the concentration of 20 μM from 66%, while as vitamin C to 67%. Compound 3 and 4 recovered more than 79% at 100 μM. The present study suggests that G. pentaphyllum has antioxidative potential and the saponins from G. pentaphyllum are considered as the active compounds with safe and neuroprotecitve effect.
- Zhai, Xin-Fang,Zu, Ma-Li,Wang, Yu-Rong,Cui, Wei-Ye,Duan, Yu,Yang, Ce,Piao, Xiang-Lan
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- A new anti-inflammatory lignan from Lonicerae Japonicae flos
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One new lignan, loniceralanside A (1), together with three known compounds (2–4), were purified from Lonicerae Japonicae Flos. Their structures were determined by HR-ESI-MS, 1 D and 2 D NMR data. Compounds 2–4 were separated from the plant for the first time. The biological test showed that compound 1 had significant anti-inflammatory activity with inhibiting the release of β-glucuronidase induced by platelet-activating factor (PAF) in rat polymorphonuclear leukocytes (PMNs) (IC50 = 3.05 μM).
- Yang, Ran,Fang, Lei,Li, Jia,Zhang, Yong-Qing
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p. 587 - 592
(2019/03/21)
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- Phytochemicals from the Leaves of Cyclocarya paliurus and their 11β-HSD1 Enzyme Inhibitory Effects
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Two new dammarane-type triterpenoid saponins, 3β-(α-l-arabinopyranosyloxy)-24,25-dihydroxydammar-20-en-12α-yl 6-deoxy-β-d-glucopyranoside (1) and (24R)-3β-[(4-O-acetyl-α-l-arabinopyranosyl)oxy]-25-hydroxy-20,24-epoxydammaran-12β-yl 6-deoxy-β-d-glucopyrano
- Yan, Huan,Li, Xiang,Ni, Wei,Zhao, Qing,Leng, Ying,Liu, Hai-Yang
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- Glycosides of polygalacic acid from the stem barks of Piper guineense Schum and Thonn
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In a continuation of our study on constituents of P. guineense now focusing on the search for saponins, phytochemical investigation of the n-BuOH fraction of P. guineense stem bark led to the isolation of three previously undescribed triterpenoid saponins, named guineenosides A─C (1─3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-{α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (1), 3-O-{α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (2), and 3-O-{α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-[α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (3). This is the first report of triterpenoid saponins from P. guineense.
- Le Doux Kamto, Eutrophe,Noté, Olivier Placide,Kinyok, Mc Jesus,Wilhelm, Anke,Mbing, Joséphine Ngo,Antheaume, Cyril,de Théodore Atchadé, Alex,Pegnyemb, Dieudonné Emmanuel,Ndinteh, Derek Tantoh,Haddad, Mohamed,Bonnet, Susan L.
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- Triterpenoid saponins and others glycosides from the stem barks of Pancovia turbinata Radlk
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In our continuing search of saponins from the plant of Sapindaceae family, phytochemical investigation of the stem barks of Pancovia turbinata Radlk., led to the isolation and structural characterization of two new triterpenoid saponins, named turbinatosi
- Moffi Biang, Armand Emmanuel,Messi, Lin Marcellin,Le Doux Kamto, Eutrophe,Simo, Line Made,Lavedan, Pierre,Vedrenne, Marc,Mbing, Josephine Ngo,Pegnyemb, Dieudonné Emmanuel,Haddad, Mohamed,Noté, Olivier Placide
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- Studies on isolation and structural identification of saponins from the herb Hylomecon japonica and their bioactivities
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Three undescribed oleanane type triterpenoid saponins (1–3), along with one known saponin (4) were isolated from the whole herb of Hylomecon japonica. Their structures were elucidated by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HR-ESI-MS) and chromatographic date (GC and LC) as 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranosyl ester (1), 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranosyl ester (2), 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranosyl ester (3), 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl ester (4). All saponins possess a partial sequence β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl at C-3 of the aglycon. Compound 1 has cytotoxic activity against human colon cancer cell lines HT29, 3 against human gastric cancer cell lines AGS, and 4 against human lung cancer cell lines A549, AGS and HT29. Among them, compounds 3 and 4 showed significant inhibitory effect against AGS with IC50 value of 6.01 ± 1.4 μM, 3.66 ± 1.8 μM, respectively. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon japonica and their bioactivities.
- Li, Fei,Wu, Si-Tong,Qu, Ming-Hui,Wang, Yi-Xiao,Ma, Chun-Liu,Yu, Bai-Hong,Wang, Guang-Shu
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- New dammarane-type triterpenoid saponins from Gynostemma pentaphyllum and their Sirt1 agonist activity
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Gynostemma pentaphyllum (Thunb.) Makino (Cucurbitaceae family) is a perennial creeping plant with a common Chinese name of “south ginseng”. To date, more than 250 individual saponins with dammarane-type skeleton have been isolated from G. pentaphyllum. The purpose of this study was the isolation and structural characterization of novel, minor gypenosides from G. pentaphyllum and evaluation of their Sirt1 agonist activity. Individual saponins from G. pentaphyllum were isolated and purified by a variety of chromatography techniques, and their structures were elucidated by means of various spectroscopic analysis and comparision with the reported data. Sirt1 enzyme activity detection kit was used to preliminarily evaluate the Sirt1 agonist activity of thirty three individual saponins purified from G. pentaphyllum. Fourteen new triterpenoid saponins named gypenoside CII-CXV (1–14) along with twenty six known compounds (15–40) were isolated from G. pentaphyllum. Thirty three of all the isolates were screened for Sirt1 agonist activity, and the results showed that three dammarane-type saponins (2, 18, 37) and one cucurbitane-type saponin 33 exhibited satisfactory Sirt1 agonist activity. These findings suggested that G. pentaphyllum was worthy of further investigation to find small molecule Sirt1 agonist and facilitate their utilization as “south ginseng”.
- Lou, Yun-Yun,Zheng, Xian,Huang, Ya-Ping,Mu, Long,Zhang, Xiao-Gai,Zhao, Zhi-Wei,Song, Zhe,Zhang, Jian,Yin, Zhi-Qi,Pan, Ke
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- Neuroprotective triterpene saponins from the leaves of Panax notoginseng
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Two new triterpene saponins, namely notoginsenoside Ng5 (1) and notoginsenoside Ng6 (2) were isolated from the leaves of Panax notoginseng, along with five known ones. Their structures were determined by chemical methods, NMR and X-ray experiments. The absolute configuration of compound 3 with four sugar units was confirmed by single crystal X-ray analysis. Compounds 2–4 and 6 inhibited PC12 cell damage induced by serum deprivation, and increased cell viability from 58.7 ± 6.7% to 66.7 ± 4.5%, 76.1 ± 6.1%, 64.7 ± 5.2% and 67.2 ± 5.0% at 10 μM, respectively.
- Huang, Ji-Wu,Du, Yi-Qian,Li, Chuang-Jun,Yang, Jing-Zhi,Ma, Jie,Zang, Ying-Da,Chen, Nai-Hong,Zhang, Dong-Ming
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supporting information
p. 2388 - 2394
(2019/11/13)
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- Oleanane-type triterpene saponins from Aralia armata leaves and their cytotoxic activity
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Two new, aramatosides A and B (1 and 2), together with seven known oleanane-type triterpene saponins (3–9) were isolated from the leaves of Aralia armata. Their structures were determined by combination of HR-ESI-MS, 1 D and 2 D NMR spectral data as well as comparison with the previous literature. Compounds 6–9 exhibited cytotoxic effects towards three human cancer cell lines (HT29, A2058, and A549) with IC50 values ranging from 2.01 ± 0.17 to 18.8 ± 1.17 μM. Especially, compound 7 (narcissiflorin) showed significant cytotoxic activity against HT29 and A549 cell lines with IC50 values of 2.02 ± 1.65 and 2.01 ± 0.17 μM, respectively, which are smaller than those of positive control irinotecan hydrochloride (IC50 values of 10.3 ± 1.32 and 9.89 ± 0.19 μM).
- Yen, Pham Hai,Chuong, Nguyen Th? Hong,Lien, Giang Thi Kim,Cuc, Nguyen Thi,Nhiem, Nguyen Xuan,Thanh, Nguyen Thi Viet,Tai, Bui Huu,Seo, Yohan,Namkung, Wan,Park, SeonJu,Kim, Seung Hyun,Minh, Chau Van,Kiem, Phan Van
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supporting information
p. 142 - 149
(2020/06/03)
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- Triterpenoid saponins from the leaves and stems of Pericampylus glaucus and their insulin mimetic activities
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During an attempt to discover insulin mimetics, thirteen new triterpenoid saponins (1–13), including three phytolaccagenic acids (1, 2, and 12) and ten serjanic acids (3–11 and 13), as aglycones were isolated from a 70% ethanol extract of leaves and stems from Pericampylus glaucus. The chemical structures of compounds 1–13 were determined through spectroscopic data analysis, including NMR, IR, and HRESIMS. All isolated compounds (1–13) were evaluated using 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose (2-NBDG) as a fluorescent-tagged glucose probe to determine their stimulatory effects on glucose uptake in differentiated 3 T3-L1 adipocyte cells. Consequently, four compounds (4, 7, 11, and 12) exhibited stimulatory effects on glucose uptake.
- Lee, Hee-Ju,Cho, Hyo-Moon,Park, Eun-Jin,Lee, Ba-Wool,Nghiem, Duc-Trong,Pham, Ha-Thanh-Tung,Pan, Cheol-Ho,Oh, Won-Keun
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- Monodesmosidic oleanene-type saponins from kidney vetch (Anthyllis vulneraria L.) with hemolytic activity
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Two undescribed monodesmosidic oleanene-type saponins, namely 3β-O-{[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl}-saikogenin G (1) and 3β-O-{[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl}-16-deoxysaikogenin F (2), named anthylloside A and B, have been isolated from an acetone-water extract from aerial parts of kidney vetch (A. vulneraria L.). Isolation of 1 and 2 was achieved by solvent partition with EtOAc and subsequent repeated chromatographic purification. The structures of the isolated compounds were elucidated by spectrometric (HR-MS) and spectroscopic methods (1H- and 13C-NMR, UV, IR and CD), as well as GC–MS analysis of samples after 1 N HCl hydrolysis and subsequent derivatization. The configuration and conformation of both 1 and 2 were assigned by means of comprehensive 2D-NMR analyses including 1H-1H?COSY, ROESY, decoupled gHSQC, gHMBC and selective 1D-TOCSY experiments. Moreover, 1 and 2 possess significant hemolytic activity, which was assessed in a blood agar assay and compared to that of three reference saponins.
- Bunse, Marek,Kammerer, Dietmar R.,Klaiber, Iris,Lorenz, Peter,Pfeiffer, Tanja,Stintzing, Florian C.,Conrad, Jürgen
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- Four New Triterpenoid Saponins from the Root of Ilex centrochinensis
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One new siaresinolic acid saponin (1) and three new rotundic acid saponins (2–4) were isolated from the roots of Ilex centrochinensis. Their structures were confirmed by detailed analysis of standard spectroscopic data (IR, MS, 1D and 2D NMR). Compounds 1–4 exhibited anti-inflammatory activity by inhibiting nitric oxide production in a lipopolysaccharide-induced RAW264.7 cell inflammatory model. However, they showed no significant lipid-lowering activity against the production of triglycerides in the lipid-accumulation model of HepG2 cells induced by oleic acid.
- Deng, Xue-Ying,Hu, Ze-Hua,Li, Lu-Jun,Lu, Yan-Xia,Shi, Yu,Yang, Hang,Yi, Ying-Tao
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- The anti-hyperuricemic effects of green alga Enteromorpha prolifera polysaccharide via regulation of the uric acid transporters in vivo
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A novel polysaccharide obtained from Enteromorpha prolifera (EPP) was purified through diethylaminoethyl cellulose-52 and Sephadex G-75 chromatography. Fourier transform infrared spectroscopy, high-performance liquid chromatography, and nuclear magnetic resonance (NMR) spectroscopy were employed to analyse the structure of EPP. It mainly comprised rhamnose, glucuronic acid, galactose, arabinose, and xylose at a molar ratio of 20.45:12.74:10.99:5.84:1.95, and its average molecular weight was 46.56 kDa. The seven major glycosidic residues identified by NMR were as follows: →2)-α-L-Araf-(1→, →2)-α-L-Rhap-(1→, →4)-α-L-Rhap-(1→, →2,6)-β-D-Galp-(1→, →4)-β-D-GlcpA-(1→, →3,4)-β-D-GlcpA-(1→, and →4)-β-Xylp-(1→. The effect of EPP on hyperuricemic mice was determined by analysing correlative general physical parameters, renal histopathology, renal gene expressions, and gut microbiome. EPP significantly reduced serum uric acid (UA), serum blood urea nitrogen, serum xanthine oxidase (XOD), and hepatic XOD as well as improved histological parameters in hyperuricemic mice. Furthermore, mRNA and protein expression analyses showed the upregulation of UA excretion genes such as ABCG2, OAT1, and NPT1 and downregulation of UA resorption gene URAT1. Moreover, EPP maintained the stability of the intestinal flora and confirmed that Parasutterella is closely related to the regulation of hyperuricemia. This study is the first to demonstrate the anti-hyperuricemic activity of EPP and highlight its therapeutic potential for hyperuricemia-related diseases.
- Chen, Xinhua,Gao, Xiaoxiang,Li, Xiaoqing,Liu, Yuanyuan,Sarker, Md Moklesur Rahman,Wu, Yijing,Zhang, Hui,Zhao, Chao
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- Hypoglycemic triterpenoid glycosides from Cyclocarya paliurus (Sweet Tea Tree)
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Four new rarely occurred seco-dammarane triterpenoid glycosides (1–4) and four new dammarane triterpenoid glycosides (5–8), along with four known triterpenoids (9–12), were isolated from the 70% ethanol extract of the leaves of Cyclocarya paliurus (family Juglandaceae). Their structures were elucidated by extensive spectroscopic methods, including 1D/2D NMR and HRESIMS data, together with chemical analysis and DFT GIAO 13C NMR calculation. In bioassay, compounds 5–8 significantly increased glucose consumption in 3T3-L1 adipocytes, which could be the bioactive constituents for the anti-diabetes effect of the traditional usage of C. paliurus.
- Chen, Zuhui,Li, Jing,Lv, Wenyan,Sun, Huihui,Tan, Jie,Wang, Wenxuan,Wu, Jianping,Xu, Jialing,Xu, Kangping,Xuan, Tongyao,Yang, Zhichun,Ye, Zijun,Zhu, Hui,Zou, Zhenxing
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- Triterpene glycosides from Silene odontopetala
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Silene species are known for their use in traditional medicine in treating several diseases. To the authors’ knowledge there is no report on the chemical composition of S. odontopetala. Therefore, the phytochemical investigation of the methanol extract of S. odontopetala was carried out, leading to the isolation of six undescribed oleanane-type glycosides along with the known saponin azukisaponin IV. Their structures were elucidated by the analysis of 1D and 2D-NMR experiments, along with mass spectrometry analysis. The cytotoxic activity of oleanane-type saponins was evaluated against a small panel of cancer cell lines, including PC-3 (prostate carcinoma cells), MCF-7 (breast cancer cells), A549 (alveolar basal carcinoma cells), and HeLa (cervical carcinoma cells). Furthermore, the activity of isolated compounds against a normal cell line HEK-293, used for assessing their cytotoxicity, was evaluated.
- ün, Rabia Nur,Alankus, Ozgen,Karayildirim, Tamer,Masullo, Milena,Nalbantsoy, Ay?e,Piacente, Sonia
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- Lanostane triterpene glycosides from the flowers of Lyonia ovalifolia var. hebecarpa and their antiproliferative activities
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Sixteen lanostane-type triterpene glycosides including eight new ones, named lyonicarposides A–H (1–8), were isolated from the flowers of Lyonia ovalifolia var. hebecarpa (Franch. ex F.B. Forbes & Hemsl.) Chun (Ericaceae). The chemical structures of the new compounds were elucidated by the comprehensive spectroscopic techniques and chemical methods. The Mo2(OAc)4–induced electronic circular dichroism method was used to determine the absolute configurations of C-24 in lyonicarposides A (1), C (3), and E (5). This is the first phytochemical study on the flowers of L. ovalifolia var. hebecarpa. All the isolates were evaluated for their antiproliferative activities against SMMC-7721, HL-60, SW480, MCF-7, and A-549 cell lines. Lyonicarposides A (1) and B (2) showed moderate antiproliferative activities against five cancer cell lines with IC50 values ranging from 12.39 to 28.71 μM. Lyonicarposides C (3) and G (7) and lyonifoloside M (12) selectively inhibited the proliferation of HL-60 and MCF-7 cell lines with IC50 values ranging from 13.03 to 17.71 μM. Interestingly, lyonifoloside L (13) selectively inhibited the proliferation of MCF-7 cell line with an IC50 value of 16.27 μM. Their structure-activity-relationships were discussed.
- Li, Shunyi,Liu, Junjun,Peng, Xiang,Teng, Yang,Yao, Guangmin,Zhang, Hanqi,Zheng, Xiaofeng,Zou, Congming
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- 3,4-seco-Dammarane Triterpenoid Saponins with Anti-Inflammatory Activity Isolated from the Leaves of Cyclocarya paliurus
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Cyclocarya paliurus is commonly used for the prevention and treatment of hypertension, diabetes, and inflammation in South China. Although research on the anti-inflammatory effects of C. paliurus leaves has been reported, no active anti-inflammatory compounds have been identified. In the present study, RAW 264.7 cells were used to establish a bioactivity-guided identification model to verify the inhibitory effects of C. paliurus leaves on inflammation and identify the anti-inflammatory constituents. The active fraction was isolated to yield 18 dammarane triterpenoid saponins, including 11 new 3,4-seco-dammarane triterpenoid saponins (1-11), the structures of which were identified on the basis of analyses of nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS) and comparison with literature data. Compounds 7, 8, 10, and 11 showed strong inhibition on nitric oxide (NO) productions, with IC50 values ranging from 8.23 to 11.23 μM. These four compounds significantly decreased the secretion of tumor necrosis factor-alpha (TNF-α), prostaglandin E2 (PGE2), and interleukin 6 (IL-6) in lipopolysaccharide-activated RAW 264.7 cells. Furthermore, compound 7 decreased the expression of the proteins cyclooxygenase-2 (COX-2), inducible nitric-oxide synthase (iNOS), and nuclear factor kappa-B (NF-κB/p65). In addition, the structure-activity relationships of the isolates were investigated. The results suggest that 3,4-seco-dammarane triterpenoid saponins may be used as potential anti-inflammatory drugs and warrant further investigation.
- Deng, Shengping,Hao, Lili,Huang, Xishan,Huang, Yan,Li, Chenguo,Li, Jun,Liu, Wei,Su, Shanshan,Xu, Xia,Yang, Ruiyun,Zhang, Gaorong,Zhou, Dexiong
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p. 2041 - 2053
(2020/03/06)
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- Structural features and anti-gastric cancer activity of polysaccharides from stem, root, leaf and flower of cultivated Dendrobium huoshanense
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The structure features and anti-gastric cancer activities in vitro of stem, root, leaf and flower polysaccharides from cultivated Dendrobium huoshanense were investigated systematically. Stem polysaccharide (cDHPS) was composed of →4)-β-D-Glcp-(1→, →4)-β-
- Liu, Bing,Shang, Zhen-Zi,Li, Qiang-Ming,Zha, Xue-Qiang,Wu, De-Ling,Yu, Nian-Jun,Han, Lan,Peng, Dai-Yin,Luo, Jian-Ping
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p. 651 - 664
(2019/12/24)
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- Saponins and flavonoid glycosides from the leaves of Ziziphus mauritiana Lam. native of a forest area of Ivory Coast
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Ziziphus mauritiana Lam (Rhamnaceae) is traditionally used in the treatment of various ailments. The aim of the present study is to identify the major compounds of the methanol extract of the leaves of Ziziphus mauritiana growing in Ivory Coast. The methanol extract of this plant was purified by combining silica gel and RP18 HPLC to give an undescribed compounds, 6’’’-O-malonyl-ziziphus saponin I (1) along with nine known compounds from which two saponins, six flavonoids, and one chalcone derivate.The structures of these compounds were elucidated by analysis of 1D- and 2D-NMR spectroscopic data and mass spectrometry (HR-ESI-MS). A part from zizyphus saponin I (2), all the others compounds were isolated for the first time from the leaves of this species.
- Seri, Chardin Seri,Okpekon, Timothée Aboua,Yao-Kouassi, Philomene Akoua,Magid, Abdulmagid Alabdul,Sayagh, Charlotte,Voutquenne-Nazabadioko, Laurence
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- New 20(S)-protopanaxadiol type saponins from the leaves of Panax notoginseng and their potential anti-inflammatory activities
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Through the combination of various chromatographies, 11 new 20(S)-protopanaxadiol (PPD) type saponins, named as notoginsenosides NL-E1 ? NL-E4 (1–4), NL-F1 (5), NL-F2 (6), NL-G1 (7), NL-G2 (8), NL-H1 ? NL-H3 (9–11) were obtained from the leaves of Panax notoginseng. Their structures were ascertained based on the extensive spectroscopic methods and chemical reactions. Meanwhile, the 20(S)-PPD type saponins with aglycone, (20S,24ζ)-3β,12β,20,24,25-pentahydroxy dammarane, was only found from the leaves of P. notoginseng. The characteristic could be used to distinguish the extracts of P. notoginseng leaves from its other medicinal parts such as roots, rhizomes, flowers or seeds. Furthermore, the nitric oxide (NO) inhibitory activities of all compounds were examined in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. As a result, compounds 2–7, 10 could exert NO inhibitory activity at 25 μM without cytotoxicity. Moreover, the inhibitory activities of them were in dose-dependent manner at 1, 10, and 25 μM. Especially, notoginsenoside NL-F2 (6) still possessed strong biological activity at 1 μM.
- Ruan, Jingya,Sun, Fan,Wang, Tao,Xiang, Guilin,Zhang, Yi,Zhang, Ying,Zhao, Wei,Zheng, Dandan
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- New C,O-Glycosylflavones from the Genus Silene
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Chromatographic separation of extracts from the aerial parts of three Silene species (Caryophyllaceae) isolated 26 flavonoids including the four new C,O-glycosylflavones acacetin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-7-O-β-D-glucopyranoside (s
- Olennikov,Kashchenko
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p. 1026 - 1034
(2020/11/05)
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- Novel steroidal glycosides from the whole plants of helleborus foetidus
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Phytochemical analysis of the whole Helleborus foetidus plants identified 28 steroidal glycosides (1-28), including 20 novel spirostanol glycosides (1-20) and a novel furostanol glycoside (21). The structures of the newly identified compounds were elucidated by two-dimensional NMR spectroscopy and hydrolytic cleavage. Compounds 12, 13, and 15 were determined to be spirostanol trisdesmosides bearing sugar moieties at the C-1, -21, and -24 hydroxy groups of the aglycone unit. The isolated compounds were subsequently evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells and A549 human lung carcinoma cells. In particular, 7 showed cytotoxic activity against the HL-60 and A549 cells, with IC50 values of 5.9 and 6.6μM, respectively, whereas 19 was selectively cytotoxic to A549 cells with an IC50 value of 5.5μM.
- Iguchi, Tomoki,Uchida, Yuka,Takano, Shingo,Yokosuka, Akihito,Mimaki, Yoshihiro
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p. 273 - 287
(2020/11/26)
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- Triterpenoid saponins with hepatoprotective effects from the fresh leaves of Metapanax delavayi
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The fresh leaves of Metapanax delavayi (Araliaceae) have been used as a common wild vegetable for salad and soup, and also herbal tea by the local people living in its growing areas of Yunnan province, China. Detailed chemical investigation led to the identification of a new triterpenoid saponin, 3-O-α-L-arabinopyranosyl-28-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl-3β-hydroxyolean-12-ene-28,29-dioic acid (1) from the fresh leaves, together with 11 known compounds, including six triterpenoid saponins (2–7), two caffeoylquinic acid derivatives (8–9), and three flavonoid glycosides (10–12). Their structures were determined on the basis of spectroscopic analysis and acidic hydrolysis. Compounds 3–5 and 8–12 were isolated from M. delavayi for the first time. Moreover, the known saponins 3-O-β-D-xylopyranosyl-3β-hydroxyolean-12-ene-28,29-dioic acid (3) and yiyeliangwanoside IV (5) exhibited protective effects on HepG2 cells damaged by the alcohol intakes, at a concentration of 1.0 μg/mL. The results indicated M. delavayi is an ideal dietary vegetable and herbal tea with potential hepatoprotective activity. (Figure presented.).
- Abe, Yuko,Gao, Da-Fang,Tanaka, Yoshihisa,Wang, Dong,Wei, Xin,Yang, Chong-Ren,Zhang, Ying-Jun,Zhu, Hong-Tao
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supporting information
p. 1373 - 1379
(2018/12/11)
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- Symplocosins C-P: Fourteen triterpene saponins from the leaves of symplocos cochinchinensis var. philippinensis
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Extensive phytochemical work on the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Symplocos cochinchinensis var. philippinensis resulted in the isolation of 14 new triterpenene saponins, along with four known ones. Their structures were elucidated by comparison of NMR spectroscopic data with related compounds reported in the literature. Three oleanane-type saponins, symplocosins K, M, and P, possessed glucuronic acid as a sugar component, and their carboxyl groups appeared as methyl esters. These are probably formed during extraction and isolation procedures. Symplocosin K (9) showed moderate cytotoxicity toward A549 cells. In addition, all isolated compounds did not show α-glucosidase inhibitory activity.
- Ohyama, Nobuhiro,Cai, Wen-Hu,Kawakami, Susumu,Sugimoto, Sachiko,Matsunami, Katsuyoshi,Otsuka, Hideaki
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p. 1090 - 1099
(2020/11/26)
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- Phenolic glycosides from Sanguisorba officinalis and their anti-inflammatory effects
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Two new phenolic glycosides 7R,8R-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-(3''-α-L-arabinofuranosyl)-β-D-glucopyranoside. (1), 4-(4'-hydroxyphenyl)-2-butanone-4''-O-(6-β-D-xylosyl)-β-D-glucopyranoside (2), along with two known related
- Chen, Jin-feng,Deng, Fang,Deng, Yun,Gu, Yu-cheng,Guo, Da-le,Jiang, Li-shi,Ju, Feng,Kuang, Qi-xuan,Tan, Lu,Yang, Tian-long
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- Antineurodegenerative Labdane Diterpenoid Glycosides from the Twigs of Pinus koraiensis
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Eleven new labdane-type diterpenoid glycosides, koraiensides A-K (1-11), together with two known analogues were isolated from the twigs of Pinus koraiensis. Their structures were elucidated via NMR, HRMS, and ECD data, DP4+ statistical analysis, and hydrolysis. The metabolites were tested for induction of nerve growth factor in C6 glioma cells to evaluate their potential neuroprotective activity. The compounds were measured for production of nitric oxide levels in lipopolysaccharide (LPS)-activated murine microglia BV2 cells to assess their antineuroinflammatory activity. Compounds 10 and 13 showed NGF secretion inducing effects from C6 glioma cells (162.3 ± 13.9percent and 162.7 ± 6.9percent, respectively). Compound 6 showed an IC50 value of 24.1 μM, implying significant inhibition of NO production.
- Khan, Zahra,Kim, Sun Yeou,Lee, Kang Ro,Park, Kyoung Jin,Subedi, Lalita
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- Antiproliferative activity of new pentacyclic triterpene and a saponin from: Gladiolus segetum Ker-Gawl corms supported by molecular docking study
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A new triterpenoidal saponin identified as 3-O-[β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-xylopyranosyl]-2β,3β,16α-trihydroxyolean-12-en-23,28-dioic acid-28-O-α-l-rhamnopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranoside 1 together with a new oleanane triterpene identified as 2β,3β,13α,22α-tetrahydroxy olean-23,28-dioic acid 2 and 6 known compounds (3-8) have been isolated from Gladiolus segetum Ker-Gawl corms. The structural elucidation of the isolated compounds was confirmed using different chemical and spectroscopic methods, including 1D and 2D NMR experiments as well as HR-ESI-MS. Moreover, the in vitro cytotoxic activity of the fractions and that of the isolated compounds 1-8 were investigated against five human cancer cell lines (PC-3, A-549, HePG-2, MCF-7 and HCT-116) using doxorubicin as a reference drug. The results showed that the saponin fraction exhibited potent in vitro cytotoxic activity against the five human cancer cell lines, whereas the maximum activity was exhibited against the PC-3 and A-549 cell lines with the IC50 values of 1.13 and 1.98 μg mL-1, respectively. In addition, compound 1 exhibited potent activity against A-549 and PC-3 with the IC50 values of 2.41 μg mL-1 and 3.45 μg mL-1, respectively. Interestingly, compound 2 showed the maximum activity against PC-3 with an IC50 of 2.01 μg mL-1. These biological results were in harmony with that of the molecular modeling study, which showed that the cytotoxic activity of compound 2 might occur through the inhibition of the HER-2 enzyme.
- Abd El-Kader, Adel M.,Abdelmohsen, Usama Ramadan,Hajjar, Dina,Hayallah, Alaa M.,Mahmoud, Basma Khalaf,Mohamed, Mamdouh F. A.
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p. 22730 - 22741
(2020/07/03)
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- α-Tetralone glycosides from the green walnut husks of Juglans mandshurica Maxim. and their cytotoxic activities
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Five new α-tetralone glycosides, juglanbiosides A-E (1–5), together with an α-tetralone derivative (15) and nine known 1,4-naphthoquinones (6–14) were isolated from the 95percent EtOH extract of green walnut husks of Juglans mandshurica Maxim. Their structures were elucidated by comprehensive spectroscopic methods (1H, 13C NMR, DEPT, HSQC, HMBC, CD, HR-ESI-MS). In vitro cytotoxicities of all the isolated compounds were evaluated against BGC-823, HCT-15 and K562 cancer cell lines. (Figure presented.).
- Gao, Hui-Rui,Guo, Shuang,Kuang, Hai-Xue,Liu, Yan,Song, Hong-Juan,Sun, Yan-Ping,Wang, Ying,Yang, Bing-You,Zhang, Xiao-Juan,Zhou, Yuan-Yuan
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p. 1805 - 1813
(2019/02/01)
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- Antioxidant Activity of Compounds Isolated from Elaeagnus umbellata Promotes Human Gingival Fibroblast Well-Being
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Four new triterpenoid bidesmosidic saponins (1-4) and a sesquiterpenoid glucoside (5), together with nine known phenolic compounds (6-14), were isolated from the fruits of Elaeagnus umbellata. Their structures were elucidated using 1D and 2D NMR spectroscopy and mass spectrometry data. The antioxidant capability of the isolated compounds was evaluated in human gingival fibroblasts. Compound 6 decreased ROS production and promoted cell proliferation. It also counteracted the cell cycle blockade induced by a low concentration of H2O2 decreasing the expression of p21 and CDKN2A (p16INK4A). Compound 6 decreased the expression of inflammatory cytokines (IL-6 and IL-8) in response to inflammatory stimuli, supporting its possible use in periodontitis lesions.
- Braca, Alessandra,Camangi, Fabiano,De Leo, Marinella,De Tommasi, Nunziatina,Giacomelli, Chiara,Iannuzzi, Anna Maria,Martini, Claudia,Pietrobono, Deborah,Trincavelli, Maria Letizia
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- Anti-adipogenic 18,19-seco-ursane stereoisomers and oleane-type saponins from Ilex cornuta leaves
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Three undescribed seco-ursane stereoisomers, ilexcornutosides A–C, two undescribed triterpenoid saponins, ilexcornutosides D–E, and 11 known triterpenoids were isolated from the leaves of Ilex cornuta Lindl. & Paxton. Ilexcornutosides A–C and F with the same planar structures are unique 13(18)-ene-18,19-seco-ursane skeleton triterpenoids, identified as (3S,12R)-3-O-[β-D-glucopyranosyl-(1 → 2)-α-L-arabinopyranosyl]-12-hydroxyl-19-oxo-18,19-secours-13(18)-en-28,21-lactone. Among them, ilexcornutosides A and F (or ilexcornutosides B and C) are a pair of diastereomers at the C-20 position; ilexcornutosides A and C (or ilexcornutosides B and F) are a pair of diastereomers with epimerization at the C-21. Their structures were established by extensive spectroscopic (IR, 1D and 2D NMR, and HR-ESI-MS) and chemical analyses. The absolute configurations of ilexcornutosides A, B, D and F were determined by a single crystal X-ray diffraction analysis with a Cu Kα radiation. The inhibitory effect of ilexcornutosides A–F on the PPARγ expression was assessed in the 3T3-L1-Lenti-PPARγ-Luc cells using a single luciferase reporter assay. Ilexcornutosides A and C showed a comparable activity in decrease of the PPARγ expression to the positive control (T0070907) at 5 μM.
- Cheng, Zhihong,Feng, Haiyan,Miao, Yu,Tang, Jihe,Wu, Tao,Zhang, Peiliang
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- Three new spirostanol glycosides from Helleborus thibetanus
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An ongoing chemical investigation on n-BuOH extract of roots and rhizomes of Helleborus thibetanus afforded three new spirostanol glycosides (1–3). Their structures were elucidated by extensive analysis of 1 D, 2 D NMR spectra, together with IR and MS met
- Li, Zhang-Peng,Su, Yan-Fang,Wei, Zi-Ye,Yang, Feng-Ying,Zhang, Hui
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p. 975 - 980
(2019/01/09)
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- Novel polysaccharide from Chaenomeles speciosa seeds: Structural characterization, α-amylase and α-glucosidase inhibitory activity evaluation
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Purification and structural characterization of a novel polysaccharide fraction from Chaenomeles speciosa seeds were investigated. After hot water extraction and ethanol precipitation, the crude polysaccharide was sequentially purified with Cellulose DEAE-52 and gel-filtration chromatography, and a highly purified polysaccharide fraction (F3) was obtained. The structure of F3 was characterized by high-performance gel permeation chromatography (HPGPC), high performance liquid chromatography (HPLC), ultraviolet-visible (UV), Fourier transform infrared (FT-IR) and nuclear magnetic resonance (NMR) spectrum, together with methylation, scanning electron microscopy (SEM), atomic force microscope (AFM), and Congo-red test analysis. The results indicated that F3 was a homogeneous polysaccharide fraction with a molecular weight of 8.65 × 106 Da, and it was composed of Rha, GlcA, Gal, and Ara in a molar ratio of 6.34:5.73:47.14:40.13. The backbone of F3 was consisted of →3,6)-Galp-(1→, and the side chains of F3 were composed of Araf-(1→, →4)-GlcpA-(1→, →4)-Galp-(1→ and →3)-Rhap-(1→. The hypoglycemic assays demonstrated F3 had good α-amylase and α-glucosidase inhibition activities, and their IC50 values were 6.24 mg/mL and 4.59 mg/mL respectively. Thus, the polysaccharide from Chaenomeles speciose could be applied as a potential natural source in retarding postprandial hyperglycemia effects.
- Cheng, Jiang,Deng, Yejun,Huang, Lixin,Liu, Lujie,Wang, Xiang,Xie, Pujun,Zhang, Caihong
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p. 755 - 766
(2020/03/18)
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- Steroidal glycosides from Ornithogalum dubium Houtt
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The phytochemical study of Ornithogalum dubium Houtt. (Asparagaceae) led to the isolation of five undescribed steroidal glycosides together with two known ones. Their structures were established by using NMR analysis and mass spectrometry as (25R)-3β-hydroxyspirost-5-en-1β-yl O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside, (25S)-3β-hydroxyspirost-5-en-1β-yl O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, (22S)-16β-[(α-L-rhamnopyranosyl)oxy]-22-hydroxycholest-5-en-3β-yl O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside, (22S,23S)-1β,3β,11α,16β,23-pentahydroxy-5α-cholest-24-en-22β-yl β-D-glucopyranoside, (22S,23S)-3β-[(β-D-glucopyranosyl)oxy]-22,23-dihydroxy-5α-cholest-24-en-16β-yl O-α-L-rhamnopyranosyl)-(1 → 4)-β-D-glucopyranoside. Their cytotoxic activities against two human cells, a lung carcinoma A-549 and a promyelocytic leukemia HL-60 cell lines, were evaluated by using the XTT method. The results showed no significant cytotoxicity on the tested cells. The influence of the potentiation of cisplatin cytotoxicity in A-549 cells was also investigated and a slight effect was observed only for the (25R) spirostane-type derivative.
- Andriamisaina, Nampoina,Mitaine-Offer, Anne-Claire,Miyamoto, Tomofumi,Tanaka, Chiaki,Paululat, Thomas,Lirussi, Frédéric,Lacaille-Dubois, Marie-Aleth
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- Structural characterization of an active polysaccharide of longan and evaluation of immunological activity
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An active polysaccharide (LPD2) was isolated from longan pulp by comparing the effects of polysaccharides on the phagocytosis of macrophages. LPD2 was composed of arabinose, mannose, glucose, and galactose in a molar ratio of 0.25:0.49:1:0.5 with average molecular weight of 9.64 × 106 Da. The main linkages of the sugar residues of LPD2 were (1→4)-β-Glc and (1→6)-β-Man. LPD2 significantly enhanced the lymphocytes proliferation, phagocytosis and NO and IL-6 secretion by macrophage. The anti-TLR2 and anti-TLR4 mAbs markedly suppressed LPD2-mediated NO and IL-6 production. Furthermore, anti-TLR4 or anti-TLR2 plus anti-TLR4 treatment significantly decreased LPD2-induced increase of MyD88, IRAK4, TRAF6 and INOS mRNA expression. Moreover, western blotting analysis showed that LPD2 enhanced the expression of target proteins in MyD88/IRAK4-TRAF6- INOS pathways. These results suggested that LPD2 induced macrophage activation partly via the TLR2- and TLR4-mediated MyD88/IRAK4-TRAF6 signaling pathways. Knowing the structural features and activities of active polysaccharide of longan gives the insights into longan polysaccharide application as an immunomodulatory agent.
- Rong, Yu,Yang, Ruili,Yang, Yuzhe,Wen, Yazhou,Liu, Sixin,Li, Congfa,Hu, Zhuoyan,Cheng, Xiangrong,Li, Wu
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p. 247 - 256
(2019/03/08)
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- Saponins from the roots of Chenopodium bonus-henricus L.
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Two new glycosides of phytolaccagenin and 2β-hydroxyoleanoic acid, namely bonushenricoside A (3) and bonushenricoside B (5) together with four known saponins, respectively compounds 3-O-L-α-arabinopyranosyl-bayogenin-28-O-β-glucopyranosyl ester (1), 3-O-β-glucuronopyranosyl-2β-hydroxygypsogenin-28-O-β-glucopyranosyl ester (2), 3-O-β-glucuronopyranosyl-bayogenin-28-O-β-glucopyranosyl ester (4) and 3-O-β-glucuronopyranosyl-medicagenic acid-28-β-xylopyranosyl(1→4)-α-rhamnopyranosyl(1→2)-α-arabinopyranosyl ester (6) were isolated from the roots of Chenopodium bonus-henricus L. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, IR and HRMS). The MeOH extract and compounds were tested for cytotoxic activity on five leukemic cell lines (HL-60, SKW-3, Jurkat E6-1, BV-173 and K-562). In addition, the ability of metanolic extract and saponins to modulate the interleukin-2 production in PHA/PMA stimulated Jurkat E6-1 cells was investigated as well.
- Kokanova-Nedialkova, Zlatina,Nedialkov, Paraskev T.,Momekov, Georgi
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p. 2024 - 2031
(2018/06/12)
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- New glycosides from the twigs and leaves of Rhododendron latoucheae
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Six new glycosides (1?6), together with three known ones, were isolated from the twigs and leaves of Rhododendron latoucheae. Their structures were elucidated based on the spectroscopic data, including infrared spectrometry, mass spectrometry, and nuclear magnetic resonance experiments, along with Mosher's method. In addition, all compounds were tested their antiviral (herpes simplex virus-1 and influenza A/95-359) activities.
- Wang, Ya-Nan,Liu, Fei,Li, Yong,Ma, Shuang-Gang,Qu, Jing,Liu, Yun-Bao,Niu, Chang-Shan,Tang, Zhong-Hai,Li, Yu-Huan,Wang, Ru-Bing,Yu, Shi-Shan
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p. 299 - 307
(2019/04/01)
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- Anti-breast cancer triterpenoid saponins from the thorns of Gleditsia sinensis
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One new triterpenoid saponin (1), as well as six known ones (2–7), were isolated from the ethanol extract of the thorns of Gleditsia sinensis. Their structures were elucidated by extensive spectroscopic analysis in conjunction with chemical evidence. Cytotoxic activity of compounds 1–6 was evaluated against human breast cancer MCF 7 cells in vitro by the MTT method. Our results revealed moderate activities for compounds 1–6 with IC50 values of 18.43, 30.47, 18.46, 10.02, 30.76, and 17.32?μM, respectively. Furthermore, compounds 1, 3, 4, and 6 induced apoptosis in MCF 7 cell, with 1 and 6 causing late apoptosis of MCF 7 cells, while 3 and 4 acting oppositely.
- Yu, Jinqian,Li, Gang,Mu, Yan,Zhou, Honglei,Wang, Xiao,Yang, Peng
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supporting information
p. 2308 - 2313
(2018/03/01)
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- Megastigmane and abscisic acid glycosides from the leaves of Laurus nobilis L.
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Two new megastigmane glycosides, laurusides E-F (1 and 3) and three known ones (2, 5, and 7), together with a new abscisic acid glycoside, lauruside G (4) and a known one (6), were isolated from a methanolic extract of Laurus nobilis L. leaves using various chromatographic techniques. The structures of these compounds were fully characterized using a combination of spectroscopic techniques including multinuclear and multidimensional NMR and mass spectrometry. All of the isolates were evaluated for their inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW264.7 cells.
- Duc Dat, Le,Viet Duc, Ngo,Thuy Luyen, Bui Thi,Van Oanh, Ha,Jang, Hyun Jae,Huong, Tran Thu,Ho Kim, Young,Thao, Nguyen Phuong
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- Terpenoid and phenolic constituents from the roots of Ilex pubescens
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Five new metabolites, including two monoterpene glycosides Pubescenosides L–M (1–2) and three phenolic glycosides, Pubescenosides N-P (3–5), along with nineteen known ones, including liganoids, hemiterpenoids and caffeoylquinic acid derivates, were isolated from the roots of Ilex pubescens. Their structures were elucidated from extensive spectroscopic analysis, including 1D and 2D NMR experiments. This study is the first to report monoterpene glycosides with β-pinene aglycone in Aquifoliaceae. Nine of these compounds were evaluated in vitro for their anti-platelet aggregation activities. Among them, compounds 3 and 4 showed moderate inhibitory activities on ADP-induced blood platelet aggregation [inhibition (%): 32.3 and 33.6, respectively] as compared to aspirin.
- Zhou, Xu-Dong,Xu, Xiang-Wei,Xi, Yi-Yuan,Zhou, Yuan
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- Molecular networking-based strategy for the discovery of polyacetylated 18-norspirostanol saponins from Trillium tschonoskii maxim.
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Nine undescribed polyacetylated 18-norspirostanol saponins, trilliumosides A?J, were obtained after a guidance based on a molecular networking strategy from the rhizomes of Trillium tschonoskii. Their structures were established by analysis of comprehensive spectroscopic data and chemical methods after their isolation in pure form. All isolated saponins were evaluated for their cytotoxicities against five selected human cancer cell lines (Huh7,A549,MCF-7,HepG2, and MOLT-4) and anti-inflammatory effects on a lipopolysaccharide (LPS)-stimulated NO production model in RAW264.7 macrophages. Trilliumoside D showed significant cytotoxicity against MOLT-4 cell lines with an IC50 value of 1.0 ± 0.1 μM, whereas trilliumosides H and I displayed remarkable anti-inflammatory effects on NO production with inhibitory rates of 56.3 ± 1.5 and 56.2 ± 2.2% at the concentration of 1.0 μM, respectively.
- Li, Dan,Liu, Hui,Ni, Wei,Xiao, Wei-Lie,He, Li,Guo, Zhen-Yu,Qin, Xu-Jie,Liu, Hai-Yang
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- C-Glycosyl Flavones from Two Eastern Siberian Species of Silene
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Flavonoids from Silene aprica Turcz. and S. samojedorum (Sambuk) Oxelman (Caryophyllaceae) growing in Baikal region were studied for the first time. A total of 14 compounds including three new compounds 1–3 were isolated. Their structures were established using UV, IR, and NMR spectroscopy and mass spectrometry. Apigenin-6-C-(2″-O-α-L-arabinopyranosyl-6″-O-acetyl)-β-D-glucopyranoside (sileneside A, 1) and apigenin-6-C-(2″-O-β-D-glucopyranosyl-6″-O-acetyl)-β-D-glucopyranoside (sileneside B, 2) were observed in S. aprica; 1 and luteolin-6-C-(2″-O-α-L-arabinopyranosyl-6″-O-acetyl)-β-D-glucopyranoside (sileneside C, 3), in S. samojedorum.
- Olennikov,Chirikova
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p. 642 - 647
(2019/08/08)
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