- LUTEOLIN 8-C-RHAMNOSIDE-7-O-THAMNOSIDE FROM PTERIS CRETICA
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A new C-glycosylflavone O-glycoside from aerial part of Pteris cretica was characterised as luteolin 8-C-rhamnoside-7-O-rhamnoside by chemical and spectral method. - Key words: Pteris cretica; Pteridaceae; C-glycosylflavone; O-glycosides; luteolin 8-C-rhamnoside-7-O-rhamnoside.
- Imperato, Filippo
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- New triterpenoid saponin from the stems of Albizia adianthifolia (Schumach.) W.Wight
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As part of our continuing study of apoptosis-inducing saponins from Cameroonian Albizia genus, one new triterpenoid saponin, named adianthifolioside J (1), together with the known gummiferaoside E (2), were isolated from Albizia adianthifolia stems. The s
- Toukea, Daniel Djou,Kamto, Eutrophe Le Doux,Simo, Line Made,Mbing, Joséphine Ngo,Antheaume, Cyril,Haddad, Mohamed,Noté, Olivier Placide,Pegnyemb, Dieudonné Emmanuel
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p. 780 - 788
(2020/08/19)
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- Phenylpropanoids from Brachybotrys paridiformis Maxim. ex Oliv. and their anti-HBV activities
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Using chemical and spectroscopic data, this study on Brachybotrys paridiformis Maxim. ex Oliv. identified four undescribed phenylpropanoids, brachin A–C and brachoside A, together with nine other known compounds. The isolated compounds were tested for anti-hepatitis B virus activities in the HepG2.2.15 cell line. Among them, caffeic anhydride showed the most potent activity.
- Ma, Chun-Liu,Qiu, He-Qin,Wang, Guang-Shu,Wang, Yi-Xiao,Wu, Si-Tong,Yu, Bai-Hong
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- Ursane-type triterpene oligoglycosides with anti-hepatosteatosis and anti-hyperlipidemic activity from the leaves of Ilex paraguariensis A. St.-Hil.
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The methanol extract from the leaves of Ilex paraguariensis A. St.-Hil. (Aquifoliaceae), popularly known as mate, maté, or yerba maté, inhibits the intracellular triglyceride accumulation in HepG2 cells and suppresses the plasma triglyceride elevation in olive oil-treated mice. Three new triterpene saponins, termed mateosides I (1), II (2), and III (3), were isolated from the extract along with 29 known compounds. The structures of 1–3 were elucidated based on chemical and spectroscopic evidence. Among the isolates, principal saponin constituents, 2 and matesaponins 1 (7) and 2 (9), potently inhibited the triglyceride accumulation in HepG2 cells simultaneously treated with oleic acid and high glucose. In vivo assay of the methanol extract of I. paraguariensis revealed that 7 and 9 showed anti-hyperlipidemic activities in olive oil-treated mice. These results suggested that the saponin constituents of I. paraguariensis could be valuable bioactive marker for the anti-obesogenic activity. Graphical abstract: [Figure not available: see fulltext.]
- Inoue, Naoki,Konno, Takuya,Manse, Yoshiaki,Morikawa, Toshio,Muraoka, Osamu,Nagatomo, Akifumi,Ninomiya, Kiyofumi,Sakamoto, Chinatsu,Shibasaka, Aya,Sone, Mayuko,Xu, Yin,Yoshikawa, Masayuki
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- Oleanane-type saponins and prosapogenins from Albizia julibrissin and their cytotoxic activities
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Two undescribed oleanane-type saponins, julibrosides K–L, along with three undescribed oleanane-type prosapogenins, julibrosides M–O, were isolated from the stem bark of Albizia julibrissin Durazz. and the mild alkaline hydrolysate of the total saponin, r
- Han, Qinghua,Qian, Yi,Wang, Xuda,Zhang, Qingying,Cui, Jingrong,Tu, Pengfei,Liang, Hong
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- Isolation, characterization, complete structural assignment, and anticancer activities of the methoxylated flavonoids from rhamnus disperma roots
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Different chromatographic methods including reversed-phase HPLC led to the isolation and purification of three O-methylated flavonoids; 5,4’-dihydroxy-3,6,7-tri-O-methyl flavone (penduletin) (1), 5,3’-dihydroxy-3,6,7,4’,5’-penta-O-methyl flavone (2), and 5-hydroxy-3,6,7,3’,4’,5’-hexa-O-methyl flavone (3) from Rhamnus disperma roots. Additionlly, four flavonoid glycosides; kampferol 7-O-α-L-rhamnopyranoside (4), isorhamnetin-3-O-β-D-glucopyranoside (5), quercetin 7-O-α-L-rhamnopyranoside (6), and kampferol 3, 7-di-O-α-L-rhamnopyranoside (7) along with benzyl-O-β-D-glucopyranoside (8) were successfully isolated. Complete structure characterization of these compounds was assigned based on NMR spectroscopic data, MS analyses, and comparison with the literature. The O-methyl protons and carbons of the three O-methylated flavonoids (1–3) were unambiguously assigned based on 2D NMR data. The occurrence of compounds 1, 4, 5, and 8 in Rhamnus disperma is was reported here for the first time. Compound 3 was acetylated at 5-OH position to give 5-O-acetyl-3,6,7,3’,4’,5’-hexa-O-methyl flavone (9). Compound 1 exhibited the highest cytotoxic activity against MCF 7, A2780, and HT29 cancer cell lines with IC50 values at 2.17 μM, 0.53 μM, and 2.16 μM, respectively, and was 2–9 folds more selective against tested cancer cell lines compared to the normal human fetal lung fibroblasts (MRC5). It also doubled MCF 7 apoptotic populations and caused G1 cell cycle arrest. The acetylated compound 9 exhibited cytotoxic activity against MCF 7 and HT29 cancer cell lines with IC50 values at 2.19 μM and 3.18 μM, respectively, and was 6–8 folds more cytotoxic to tested cancer cell lines compared to the MRC5 cells.
- Abd El-Wahab, Mohammed F.,Abdalla, Ashraf N.,Mohammed, Abd El-Salam I.,Mohammed, Hamdoon A.,Ragab, Ehab A.,Shaheen, Usama
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- A new triterpenoid saponin from Glinus oppositifolius
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From the ethanol extract of Glinus oppositifolius, collected at Phu Yen province, Viet Nam, one new triterpenoid saponin (1) and four known compounds (2–5) were isolated. By means of NMR and HR-ESI-MS analyses, their structure was elucidated as 3-O-(β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl)spergulagenin A or glinusopposide V (1), glinusopposide L (2), spergulin B (3), vitexin (4) and astralagin (5). Two compounds (1–2) showed weak inhibitory activity against α-glucosidase.
- Phan, Thuy Thanh,Do, Lien T. M.,Phung, Trung Van,Nguyen, Thu Thi Hoai,Huynh, Vinh N.,Ngo, Duong Thi Thuy,Nguyen, Kim Phi Phung,Nguyen, Tuyet Thi Anh
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p. 171 - 176
(2020/07/03)
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- Undescribed chalcone and stilbene constituents from Lysimachia baviensis and their anti-inflammatory effect
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The chemical composition and anti-inflammatory activity of the endemic Lysimachia baviensis were investigated for the first time in this study. A phytochemical fractionation of the methanol extract of L. baviensis resulted in the isolation of a new stilbene (bavienside A, 1) and two new chalcone glycosides (baviensides B and C, 2 and 3). Their structures were elucidated via the interpretation of NMR and HRESIMS spectroscopic data. Compounds 1–3 strongly inhibited the production of nitric oxide in LPS-induced RAW264.7 cells with the IC50 values of 6.23, 2.86 and 3.51 μM, respectively. The C-acetylstilbene and carbomethyl chalcone structures in compound 1 and 3 were found for the first time from natural source and could be important markers for chemotaxonomy of Lysimachia baviensis.
- Dat, Nguyen Tien,Hau, Dang Viet,Hong Anh, Nguyen Thi,Hung, Nguyen Quang,Huong, Nguyen Thi Thanh,Khang, Nguyen Sinh,Luyenb, Nguyen Thi
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- Identification and occurrence of phenylethanoid and iridoid glycosides in six Polish broomrapes (Orobanche spp. and Phelipanche spp., Orobanchaceae)
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There are about 200 holoparasitic broomrapes (Orobanchaceae) known worldwide, however, only several species have been so far investigated phytochemically. Among Orobanche s.l. are both rare and endangered species, as well as onerous crop pests. This study aims to give a phytochemical description, both qualitative and quantitative, of six broomrape species (Orobanche and Phelipanche taxa) growing in Poland, including species that have not been tested in detail (O. caryophyllacea, O. lutea, O. picridis, and P. arenaria). Sixteen metabolites, including 14 phenylethanoid glycosides (PhGs) and 2 iridoid glycosides (IrGs), were isolated and identified using NMR spectroscopy and hydrolysis, revealing the presence of two previously undescribed PhGs in P. ramosa, named ramoside A and 2′-acetylramoside A. In addition, in the example of O. caryophyllacea, we have reported as the first occurrence of IrGs in broomrapes. Concentrations of phenylethanoids, the main constituents of broomrapes, in the studied plant material (flowering shoots with haustoria) were determined using the UHPLC-PDA method. It was found that P. ramosa has been the richest source of PhGs. In addition, the differences between broomrapes have been visualized using principal component and cluster analysis. The results of the antiradical DPPH test of 13 PhGs confirmed previous findings on the relation of the antioxidant potential with the structure of phenolic moieties – phenolic acid and phenylethanoid unit.
- Jedrejek, Dariusz,Pawelec, Sylwia,Piwowarczyk, Renata,Pecio, ?ukasz,Stochmal, Anna
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- Steroidal saponins from Trillium tschonoskii rhizomes and their cytotoxicity against HepG2 cells
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A phytochemical study on the rhizomes of Trillium tschonoskii led to the isolation of fourteen new steroidal saponins, trillitschosides S1-S14 (1–14), along with ten known analogues (15–24). Their structures were established mainly by spectroscopic analyses as well as necessary chemical evidence. All isolated compounds were screened for the cytotoxicity against HepG2 cells, and the results demonstrated that only the known compounds 21–24 exhibited the remarkable cytotoxic activity against HepG2 cells which is much better than the positive control of 5-FU.
- Chen, Xiao-Juan,Guo, Bao-Lin,Li, Qi,Ma, Bai-ping,Pang, Xu,Sun, Xin-Guang,Wang, Bei,Yang, Jie,Yang, Yin-Jun,Zhang, Jie
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- Triterpenic saponins from Medicago marina L
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The saponin composition of leaves and roots from Medicago marina L., sea medic, was investigated by a combination of chromatographic, spectroscopic and spectrometric (GC, LC, ESI-MS/MS, NMR) methods. Several compounds were detected and quantified by HPLC using the external standard method. Saponins from this plant species consist of a mixture of high molecular weight bidesmosidic derivatives of medicagenic and zanhic acid, containing up to six sugars in the molecules. Six of the detected saponins were previously isolated and reported as constituents of other Medicago spp.; one saponin was previously described in other plant species; four saponins are undescribed compounds in Medicago and never reported before in other plant species. These are: 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[β-D-apiofuranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester; 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester; 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylmedicagenic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester and 3-O-β-D-glucopyranosylmedicagenic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester. The specific saponins synthesized by M. marina may have a role in its tolerance to environment, representing a reservoir of osmolytic sugars.
- Accogli, Rita,Argentieri, Maria Pia,Avato, Pinarosa,Biazzi, Elisa,Doria, Filippo,Mella, Mariella,Ronga, Domenico,Tava, Aldo
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- Steroidal saponins and sapogenins from fenugreek and their inhibitory activity against α-glucosidase
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The seed of Trigonella foenum-graecum L. (fenugreek) has been reported to be rich in saponins, especially the dioscin or diosgenin, which are natural anti-diabetic agents with relatively low toxicity. Thus, the present study was to purify the saponins and sapogenins from fenugreek and to evaluate their α-glucosidase inhibitory activity in vitro. As a result, 33 steroidal saponins and sapogenins were isolated, including six undescribed ones and 27 previously known molecules. Among them, compounds 10, 12, 17, 22 and 29 were five 25R and 25S isomer mixtures of spirostanol saponins or sapogenins. The structures of compound 1–6 were established by 1D and 2D NMR spectroscopic analyses, high-resolution mass spectrometry, and chemical evidence. Compared to the positive control, sapogenins 26, 27, 14 and saponins 18 and 23 considerably inhibited α-glucosidase at IC50 values of 15.16, 8.98, 7.26, 5.49 and 14.01 μM, respectively. These results support the therapeutic potential of fenugreek in the treatment of diabetes with saponins and sapogenins as the active constituents.
- Dai, Rongke,Wang, Meizhe,Xia, Xiaoyan,Xu, Jing,Zhang, Huixing,Zhao, Yuqing
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- Identification of potential anti-inflammatory and melanoma cytotoxic compounds from Aegiceras corniculatum
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Many chemicals found in mangroves reportedly exhibit potent anticancer, antibacterial, anti-inflammatory, antioxidant, and antitumor properties. Several of such compounds include feature unique structures and display interesting pharmacological effects. Few medicinal mangrove plants from Vietnam have been characterized with regard to their chemical constituents. Aegiceras corniculatum (L.) Blanco is a mangrove shrub that exhibits activity against various types of cancer. To identify new secondary metabolites and determine the source(s) of biological activity in Vietnamese medicinal mangrove plants, the chemical constituents of A. corniculatum were isolated, and their structures were appropriately established using common spectroscopic methods (1D and 2D-NMR, IR, HR-ESI-MS), and by producing derivatives by chemical reactions. Complementarily, it is worth noting, that the anti-inflammatory effects of the isolated compounds were investigated by measuring the production of pro-inflammatory cytokines IL-12 p40, IL-6, and TNF-α in lipopolysaccharide-stimulated bone marrow-derived dendritic cells; in this sense, the target compounds 2 and 3 were potent inhibitors of cytokines TNF-α, IL-6, and IL-12 p40, indicating promising anti-inflammatory effects. Furthermore, compounds 1 and 4 strongly promoted apoptosis of B16F10 melanoma cells. It is convenient to highlight, that the obtained results suggest that saponins from A. corniculatum could be potential candidates for treating cancer and inflammatory illnesses.
- Vinh, Le Ba,Phong, Nguyen Viet,Ali, Irshad,Dan, Gao,Koh, Young Sang,Anh, Hoang Le Tuan,Van Anh, Do Thi,Yang, Seo Young,Kim, Young Ho
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p. 2020 - 2027
(2020/09/01)
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- Two new acylated triterpenoidal saponins from Gleditsia caspica Desf. and the effect of its saponin content on LPS-induced cognitive impairment in mice
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Two bisdismosidic triterpenoidal saponins, caspicaoside A1 (1) and caspicaoside B1 (2), were isolated from Gleditsia caspica fruit methanolic extract. The structures of 1 and 2 were determined using chemical and spectral techniques. Gleditsia caspica fruit methanolic extract (MEGC) and its saponin containing fraction (SFGC) at the two dose levels 45 and 90 mg/kg b.wt. were studied comparatively for their effect on LPS-induced cognitive impairment in mice using Ginkgo biloba (100 mg/kg b.wt.) as a standard drug. Neurobehavioral tests (Morris Water Maze and Novel Object Recognition tests) were conducted to prove that MEGC and SFGC at the two levels were able to significantly improve memory and learning in mice dose dependently. Also, the two test drugs were able to significantly decrease the levels of proinflammatory cytokines (Tumor necrosis factor alpha and Interleukin 1-beta) in addition to reducing the extra-cellular deposition of amyloid beta 42 in a dose dependent manner.
- Kassem, I. A. A.,Melek, F. R.,Nabil, Marian,Ragab, Mai F.
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- Flavonol Glycosides from Leaves of Allium microdictyon
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The composition of flavonoids from leaves of Allium microdictyon Prokh. (Amaryllidaceae) was studied for the first time and included 14 compounds including two new flavonol glycosides 1 and 2. UV, IR, and NMR spectroscopic and mass spectrometric data dete
- Olennikov
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p. 1035 - 1039
(2020/11/03)
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- Cycloartane and oleanane glycosides from the tubers of Eranthis cilicica
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Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1-11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.
- Watanabe, Kazuki,Mimaki, Yoshihiro,Fukaya, Haruhiko,Matsuo, Yukiko
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- An alkali tolerant α-L-rhamnosidase from Fusarium moniliforme MTCC-2088 used in de-rhamnosylation of natural glycosides
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Analkali tolerant α-L-rhamnosidase has been purified to homogeneity from the culture filtrate of a new fungal strain, Fusarium moniliforme MTCC-2088, using concentration by ultrafiltration and cation exchange chromatography on CM cellulose column. The molecular mass of the purified enzyme has been found to be 36.0 kDa using SDS-PAGE analysis. The Km value using p-nitrophenyl-α-L-rhamnopyranoside as the variable substrate in 0.2 M sodium phosphate buffer pH10.5 at50 °C was 0.50 mM. The catalytic rate constant was15.6 s?1giving the values of kcat/Km is 3.12 × 104M?1 s?1. The pH and temperature optima of the enzyme were 10.5 and 50 °C, respectively. The purified enzyme had better stability at 10 °C in basic pH medium. The enzyme derhamnosylated natural glycosides like naringin to prunin, rutin to isoquercitrin and hesperidin to hesperetin glucoside. The purified α-L-rhamnosidase has potential for enhancement of wine aroma.
- Kumar, Dhirendra,Yadav, Sarita,Yadava, Sudha,Yadav
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- Chemical Constituents from the Roots of Polygala arillata and Their Anti-Inflammatory Activities
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A new compound, named arillatanoside E, which was elucidated as 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1 - 3)-β-D-xylopyranosyl-(1 - 4)-α-L-rhamnopyranosyl-(1 - 2)-(4-O-acetyl)-β-D-fucopyranosyl ester, along with 11 known compounds was isolated from the ethanolic extract of the roots of Polygala arillata. The 11 known compounds were identified as oleanolic acid (2), 3′-E-3,4,5-trimethoxy cinnamoyl-6-benzoyl sucrose (3), trans-ferulic acid (4), trans-feruloyl-glucoside (5), feruloyl-glucoside (6), 2,4,6-trimethoxy-1-O-β-D-glycoside (7), 3-methoxy-4-hydroxybenzoic acid (8), monopentadecanoin (9), sinapic acid (10), p-hydroxybenzaldehyde (11), and palmitic acid (12). Among them, seven isolated compounds 1, 2, 4, 5, 7, 8, and 10 exhibited little cytotoxic activity on macrophage RAW 264.7 cells. Then, the inhibitory effects of 7 isolates on nitric oxide (NO) production in lipopolysaccharide-activated macrophages were evaluated. As a result, 3 compounds have significant anti-inflammatory activity, and they were arillatanoside E (1), oleanolic acid (2), and 2,4,6-trimethoxy-1-O-β-D-glycoside (7).
- Xiang, Wei,Zhang, Guo-Dong,Li, Fang-Yi,Wang, Teng-Long,Suo, Tong-Chuan,Wang, Chun-Hua,Li, Zheng,Zhu, Yan
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- New furostanol glycosides from Polygonatum multiflorum (L.) All
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The phytochemical investigation of the whole plant of Polygonatum multiflorum resulted in the isolation of two new steroidal glycosides, polmultoside A (4) and polmultoside B (5), along with three known glycosides protobioside (1), protodeltonin (2) and huangjiangsu A (3). The structures of the isolated compounds have been elucidated by extensive 1D (1H, 13C) and 2D (COSY, HSQC, HMBC) NMR spectral data analysis, as well as high-resolution mass determinations.
- Gvazava, Lili,Nebieridze, Vazha,Ganzera, Markus,Skhirtladze, Alexander
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- Six New Coumarin Glycosides from the Aerial Parts of Gendarussa vulgaris
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Six new coumarin glycosides, genglycoside A–F (1–6), were isolated from the aerial parts of Gendarussa vulgaris, along with ten known analogues (7–16). Their structures were unambiguously established on the basis of extensive spectroscopic data and HPLC analysis. The cytotoxic activities of all isolated compounds were evaluated by MTT assay. Compound 12 showed the most potent cytotoxicity in Eca-109, MCF-7, and HepG2 cell lines. By the preliminary structure–activity relationships, it was firstly discovered that the glycosylation or esterification at 7,8-dihydroxy or 7-hydroxy drastically reduced the cytotoxic activity of the parent coumarin.
- Sun, Yanjun,Gao, Meiling,Chen, Haojie,Han, Ruijie,Chen, Hui,Du, Kun,Zhang, Yanli,Li, Meng,Si, Yingying,Feng, Weisheng
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- Four New Flavonoids Isolated from the Aerial Parts of Cadaba rotundifolia Forssk. (Qadab)
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Cadaba rotundifolia (Forssk.) (family: Capparaceae; common name: Qadab) is one of four species that grow in the Red Sea costal region in the Kingdom of Saudi Arabia. The roots and leaves of C. rotundifolia is traditionally used to treat tumors and abscesses in Sudan. A previous phytochemical study of the roots yielded a quaternary alkaloid, but no report on chemical constituents of the aerial parts of the C. rotundifolia growing in Saudi Arabia has been issued so far. Oxidative stress and advanced glycation end products (AGEs) are thought as causal factors in many degenerative diseases, such as Alzheimer's disease, diabetes, atherosclerosis and aging. In this study, a total of twenty compounds, including four previously undescribed acylated kaempferol glucosides, were isolated from the aerial parts of C. rotundifolia collected in Saudi Arabia. These new compounds were identified as kaempferol 3-O-[2-O-(trans-feruloyl)-3-O-β-d-glucopyranosyl]-β-d-glucopyranoside (1), kaempferol 3-O-β-neohesperidoside-7-O-[2-O-(cis-p-coumaroyl)-3-O-β-d-glucopyranosyl]-β-d-glucopyranoside (2), kaempferol 3-O-[2,6-di-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside-7-O-[6-O-(trans-feruloyl)]-β-d-glucopyranoside (3) and kaempferol 3-O-[2,6-di-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside-7-O-[6-O-(trans-p-coumaroyl)]-β-d-glucopyranoside (4). Their structures were established based on UV-visible, 1D, 2D NMR, and HR-ESI-MS analyses. Of the assayed compounds, 17 and 18 showed potent radical scavenging activity with IC50 values of 14.5 and 11.7 μM, respectively, and inhibitory activity toward AGEs together with compound 7 with IC50 values 96.5, 34.9 and 85.5 μM, respectively.
- Al-Hamoud, Gadah Abdulaziz,Orfali, Raha Saud,Sugimoto, Sachiko,Yamano, Yoshi,Alothyqi, Nafee,Alzahrani, Ali Mohammed,Matsunami, Katsuyoshi
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- Purification and characterization of an intracellular α-L-rhamnosidase from a newly isolated strain, Alternaria alternata SK37.001
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A strain, Alternaria alternata SK37.001, which produces an intracellular α-L-rhamnosidase, was newly isolated from citrus orchard soil. The molecular mass of the enzyme was 66 kDa, as evaluated by SDS-PAGE and 135 kDa, as determined by gel filtration, which indicated that the enzyme is a dimer. The enzyme had a specific activity of 21.7 U mg?1 after step-by-step purification. The optimal pH and temperature were 5.5 and 60 °C, respectively. The enzyme was relatively stable at a pH of 4.0–8.0 and a temperature between 30 and 50 °C compared with other pH levels and temperatures investigated. The enzyme activity was accelerated by Ba2+ and Al3+ but inhibited by Ni2+, Cu2+ and Co2+, especially Ni2+. The kinetic parameters of Km and Vmax were 4.84 mM and 53.1 μmol mg?1 min?1, respectively. The α-L-rhamnosidase could hydrolyze quercitrin, naringin and neohesperidin, hesperidin and rutin rhamnose-containing glycosides but could not hydrolyze ginsenoside Rg2 or saiko-saponin C.
- Zhang, Tao,Yuan, Wenbo,Li, Mengli,Miao, Ming,Mu, Wanmeng
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- Chemical constituents and antioxidant, anti-inflammatory and anti-tumor activities of melilotus officinalis (linn.) pall
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Two new p-hydroxybenzoic acid glycosides, namely p-hydroxybenzoic acid-4-O-α-D-manopyranosyl-(1 → 3)-α-L-rhamnopyranoside (compound 1) and 4-O-α-L-rhamnopyran-osyl-(1 → 6)-α-D-manopyranosyl-(1 → 3)-α-L-rhamnopyranoside (compound 2), and seven known compounds, compound 3, 6, 7 (acid components), compound 8, 9 (flavonoids), compound 4 (a coumarin) and compound 5 (an alkaloid), were isolated from the 70% ethanol aqueous extract of the aerial parts of Melilotus officinalis (Linn.) Pall. The structures of all compounds were elucidated by use of extensive spectroscopic methods Infrared Spectroscopy (IR), High resolution electrospray ionization mass spectrometry (HR-ESI-MS), and1H and13C-NMR). Sugar residues obtained after acid hydrolysis were identified by high-performance liquid chromatography (HPLC). The antioxidant activity of all the compounds was evaluated by 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS+) and 1,1-diphenyl-2-picrylhydrazyl (DPPH). The anti-inflammatory effects of the compounds were also evaluated in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. All compounds were shown to inhibit LPS-induced nitric oxide (NO) and prostaglandin E 2 (PGE 2) production by suppressing the expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2), respectively, in LPS-stimulated RAW 264.7 cells. The inhibitory effect of all the compounds on MCF-7 cells was determined by Cell Counting Kit-8 (CCK-8) method. The results showed that compounds 1, 2, 7, 8, 9 exhibited better antioxidant activity compared to the other compounds. compounds 1–9 had different inhibitory effects on the release of NO, TNF-α and IL-6 in LPS-stimulated RAW264.7 cells by LPS, of which compound 7 was the most effective against inflammatory factors. compounds 1 and 2 have better antitumor activity compared to other compounds. Further research to elucidate the chemical composition and pharmacological effects of Melilotus officinalis (Linn.) Pall is of major importance towards the development and foundation of clinical application of the species.
- Liu, Yu-Ting,Gong, Pei-Han,Xiao, Feng-Qin,Shao, Shuai,Zhao, Da-Qing,Yan, Ming-Ming,Yang, Xiu-Wei
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- New steroidal saponins from the rhizomes of Paris vietnamensis and their cytotoxicity
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Four new spirostanol saponins, named pavitnosides A-D (1-4), with six known steroidal saponins 5-10 were isolated from the rhizomes of Paris vietnamensis. Their chemical structures were determined based on extensive spectroscopic studies and chemical methods. The aglycones of pavitnoside B and pavitnoside C were not reported in previous work. The cytotoxicity of all saponins was evaluated against human glioblastoma U87MG and U251 cell lines. The new spirostanol saponin 1 displayed weak anti-proliferative activity against U87MG cell line and the known saponins 8 and 9 exhibited significant cytotoxicity against the two tumor cell lines, with IC50 values of 2.16 to 3.14 μM, but did not affect the growth of primary cultures of human astrocytes.
- Liu, Yang,Wang, Minchang,Liu, Ke,Qiu, Pengcheng,Zhang, Shan,Lu, Yunyang,Tang, Na,Tang, Haifeng
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- New natural barrigenol-like triterpenoid isolated from the husks of Xanthoceras sorbifolia Bunge
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The Xanthoceras sorbifolia Bunge husks were known for their abundant triterpenoids resource, which contributed to many bioactivities, such as antitumor, antiinflammatory and neuroprotection. The present study has led to the purification of a new triterpenoid saponin, 21β-O-acetyl-xanthohuskiside A (1), together with six known barrigenol derivatives (2–7), whose structures were authenticated on the basis of NMR, HR-MS, IR spectrum and acid hydrolysis experiment. Compound 7 showed more noteworthy cytotoxicity towards three human tumour cell lines (HCT-116, HepG-2 and U87-MG) than other compounds.
- Wang, Da,Yu, Bin,Chen, Chuming,Duan, Jie,Di, Donghua,Xiong, Xin,Yang, Yiren,Gao, Huiyuan
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p. 997 - 1003
(2017/09/27)
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- Lignan glycosides and flavonoid glycosides from the aerial portion of Lespedeza cuneata and their biological evaluations
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Lespedeza cuneata (Fabaceae), known as Chinese bushclover, has been used in traditional medicines for the treatment of diseases including diabetes, hematuria, and insomnia. As part of a continuing search for bioactive constituents from Korean medicinal plant sources, phytochemical analysis of the aerial portion of L. cuneata led to the isolation of two new lignan glycosides (1,2) along with three known lignan glycosides (3–7) and nine known flavonoid glycosides (8–14). Numerous analysis techniques, including 1D and 2D NMR spectroscopy, CD spectroscopy, HR-MS, and chemical reactions, were utilized for structural elucidation of the new compounds (1,2). The isolated compounds were evaluated for their applicability in medicinal use using cell-based assays. Compounds 1 and 4–6 exhibited weak cytotoxicity against four human breast cancer cell lines (Bt549, MCF7, MDA-MB-231, and HCC70) (IC50 30.0 μM). However, none of the isolated compounds showed significant antiviral activity against PR8, HRV1B, or CVB3. In addition, compound 10 produced fewer lipid droplets in Oil Red O staining of mouse mesenchymal stem cells compared to the untreated negative control without altering the amount of alkaline phosphatase staining.
- Baek, Jiwon,Lee, Tae Kyoung,Song, Jae-Hyoung,Choi, Eunyong,Ko, Hyun-Jeong,Lee, Sanghyun,Choi, Sang Un,Lee, Seong,Yoo, Sang-Woo,Kim, Seon-Hee,Kim, Ki Hyun
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- Melanogenesis-Inhibitory and Cytotoxic Activities of Triterpene Glycoside Constituents from the Bark of Albizia procera
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Five oleanane-type triterpene glycosides including three new ones, proceraosides E-G (1-3), were isolated from a MeOH-soluble extract of Albizia procera bark. The structures of 1-3 were determined by use of NMR spectra, HRESIMS, and chemical methods. Compounds 1-5 exhibited inhibitory activities against the proliferation of the A549, SKBR3, AZ521, and HL60 human cancer cell lines (IC50 0.28-1.8 μM). Additionally, the apoptosis-inducing activity of compound 2 was evaluated by Hoechst 33342 staining and flow cytometry, while the effects of 2 on the activation of caspases-9, -8, and -3 in HL60 cells were revealed by Western blot analysis.
- Zhang, Jie,Akihisa, Toshihiro,Kurita, Masahiro,Kikuchi, Takashi,Zhu, Wan-Fang,Ye, Feng,Dong, Zhen-Huan,Liu, Wen-Yuan,Feng, Feng,Xu, Jian
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supporting information
p. 2612 - 2620
(2019/01/04)
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- Inhibitory effects of constituents from the aerial parts of rosmarinus officinalis L. on triglyceride accumulation
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Sixteen flavonoids (1-16) including two new ones, named officinoflavonosides A (1) and B (2) were obtained from the aerial parts of Rosmarinus officinalis. Among the known ones, 6, 10, and 13 were isolated from the rosmarinus genus for the first time. The
- Li, Jian,Adelakun, Tiwalade Adegoke,Wang, Sijian,Ruan, Jingya,Yang, Shengcai,Li, Xiaoxia,Zhang, Yi,Wang, Tao
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- Cytotoxic steroidal saponins from Trillium kamtschaticum
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Eight new steroidal saponins, trillikamtosides K–R (1–8), along with three known analogues, were isolated from the whole plants of Trillium kamtschaticum. Their structures were unambiguously established by interpretation of spectroscopic data (MS and NMR) and chemical methods. Compound 1 had a rare aglycone featuring a skeleton of 16-oxaandrost-5-en-3-ol-17-one, which was reported for the first time. The isolated saponins were tested for cytotoxicities against HCT116 cells, and trillikamtoside R (8) was found to show the most cytotoxic effect with an IC50 value of 4.92?μM.
- Qin, Xu-Jie,Si, Yong-Ai,Chen, Yu,Liu, Hui,Ni, Wei,Yan, Huan,Shu, Tong,Ji, Yun-Heng,Liu, Hai-Yang
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supporting information
p. 2267 - 2273
(2017/05/10)
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- Structural characterization of a new steroidal saponin from Agave angustifolia var. Marginata and a preliminary investigation of its in vivo antiulcerogenic activity and in vitro membrane permeability property
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A new furostane steroidal saponin was isolated from the leaves of Agave angustifolia var. marginata. On the basis of chemical conversions and spectroscopic analyses, its structure was established as 3-[O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→3)-O]-[O-6-deoxy-α-L-mannopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl)oxy]-(3β,5α,22α,25R)-26-(β-D-glucopyranosyloxy)-22-methoxy-furostane (1). Results of preliminary biological investigations indicated that compound 1 showed significant protective effects against induced gastric ulcers using in vivo experimental models and demonstrated negligible toxicity on membrane integrity in the in vitro assays.
- Pereira, Gabriela Moysés,Ribeiro, Marcela Gon?alves,da Silva, Bernadete Pereira,Parente, José Paz
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p. 4345 - 4349
(2017/09/12)
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- New triterpenoid saponins from the herb hylomecon japonica
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Background: Hylomecon japonica, a plant of the Papaveraceae family which is well-known for the alkaloids they produce, is a perennial plant widely distributed in the northeast, central and east regions of China. Although a variety of chemical constituents, including alkaloids, flavonoids, and megastigmoids, have been isolated from H. japonica, the investigation of saponins in H. japonica has not been reported until now. Methods: Various separation techniques, including polyporous resin column chromatography, silica gel column chromatography and hemi-preparative HPLC were applied to the isolation of triterpenoid saponins, and chemical methods such as acid hydrolysis and spectroscopic methods including HRESIMS and NMR were applied to their structure elucidation, and the XTT reduction method was used to assay cytotoxicity. Results: Two new triterpenoid saponins, named hylomeconoside A (1) and B (2) which were identified as 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl-gypsogenin-28-O-β-D-xylopyranosyl- (1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-quinovopyranoside (1) and 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl-gypsogenin-28-O-β-D-xylopyranosyl- (1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside (2), and two known triterpenoid saponins identified as dubioside C (3) and lucyoside P (4) on the basis of spectroscopic and chemical evidence, were isolated from H. japonica. Compound 1 exhibited moderate cytotoxicity on MGC-803 and HL-60 cells, with IC50 values of 43.8 and 32.4 μg.mL-1, respectively. Conclusions: Compounds 1 and 2 are new saponins, and 1 is considered to be one of the antitumor principles in this plant. This is the first time that triterpenoid saponins have been isolated from plants of the Papaveraceae family.
- Qu, Yan-Fei,Gao, Jing-Yu,Wang, Jing,Geng, Yan-Mei,Zhou, Yu,Sun, Cheng-Xin,Li, Fei,Feng, Lei,Yu, Meng-Juan,Wang, Guang-Shu
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- New triterpene saponins from the roots of Acacia macrostachya (Mimosaceae)
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Four new oleanane-type saponins, macrostachyaosides A, B, C, and D (1–4) were isolated from the roots of Acacia macrostachya. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR data and HR-ESI-MS analyses. At concentrations of 100 μM of each compounds, none of the tested compounds caused a significant growth reduction against HL60 cells.
- Tchoukoua, Abdou,Tabopda, Turibio Kuiate,Usukhbayar, Narandulam,Kimura, Ken-ichi,Kwon, Eunsang,Momma, Hiroyuki,Koseki, Takuya,Shiono, Yoshihito,Ngadjui, Bonaventure Tchaleu
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p. 2261 - 2267
(2017/12/26)
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- Bioactive compounds from the stems of clausena lansium
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In view of the significant neuroprotective effect of Clausena lansium, we continued to separate the n-butanol and the water extracts from the stems of C. lansium in order to find the leading compounds with significant activity. Two new phenolic glycosides, Clausenolside A-B (1-2), one new pair of phenolic enantiomers (3a, 3b), and two new monoterpenoids, clausenapene A-B (4-5), together with twelve known analogues (6-17) were isolated from the stems of C. lansium. Compounds 1-17 were obtained from C. lansium for the first time. Compounds 3a, 3b, 4, 16, and 17 showed strong or moderate potential neuroprotective effects on inhibited PC12 cell injury induced by okadaic acid, and compound 9 exhibited strong potential hepatoprotective activities. Their structures were elucidated on the basis of spectroscopic analyses, including UV, IR, NMR experiments, and electronic circular dichroism (ECD) spectra.
- Liu, Jie,Li, Chuang-Jun,Du, Yi-Qian,Li, Li,Sun, Hua,Chen, Nai-Hong,Zhang, Dong-Ming
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- Five New Oleanane Triterpenoid Saponins from the Aerial Parts of Elsholtzia bodinieri
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Five new oleanane triterpenoid saponins, bodiniosides H - L (1 - 5, resp.), were isolated from the aerial parts of Elsholtzia bodinieri. Their structures were elucidated on the basis of spectroscopic techniques, including HSQC, HMBC, and HSQC-TOCSY experiments, together with acid hydrolysis and GC analysis.
- Zhong, Jin-Dong,Zhao, Xue-Wei,Li, Hong-Mei,Gao, Ling-Huan,Li, Rong-Tao
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p. 204 - 209
(2016/04/19)
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- Acylated oleanane-type triterpene saponins from the flowers of Bellis perennis show anti-proliferative activities against human digestive tract carcinoma cell lines
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Seven oleanane-type triterpene saponin bisdesmosides, perennisaponins N–T (1–7), were newly isolated from a methanol extract of daisy, the flowers of Bellis perennis L. (Asteraceae). The structures were determined based on chemical and physicochemical data and confirmed using previously isolated related compounds as references. The isolates, including 13 previously reported perennisaponins A–M (8–20), exhibited anti-proliferative activities against human digestive tract carcinoma HSC-2, HSC-4, and MKN-45 cells. Among them, perennisaponin O (2, IC50?=?11.2, 14.3, and 6.9?μM, respectively) showed relatively strong activities. The mechanism of action of 2 against HSC-2 was found to involve apoptotic cell death.
- Ninomiya, Kiyofumi,Motai, Chiaki,Nishida, Eriko,Kitagawa, Niichiro,Yoshihara, Kazuya,Hayakawa, Takao,Muraoka, Osamu,Li, Xuezheng,Nakamura, Seikou,Yoshikawa, Masayuki,Matsuda, Hisashi,Morikawa, Toshio
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p. 435 - 451
(2016/07/16)
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- Six new compounds from Atractylodes lancea and their hepatoprotective activities
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Two new phenolic glycosides with a rare β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl moiety (1, 2), one new dihydrobenzofuran derivative (3), one new pyrazine derivative (4), two new furofuran lignan glycosides (5, 6), and six known compounds (7–12) were isolated from the rhizomes of Atractylodes lancea. The structures of these compounds were elucidated by extensive spectroscopic analyses combined with the experimental and calculated electronic circular dichroism and the Rh2(OCOCF3)4-induced circular dichroism for configurational assignments. Notably, compounds 1–3 showed significant hepatoprotective activities against N-acetyl-p-aminophenol-induced HepG2 cell injury. This study is also the first Letter on the isolation of furofuran lignans and pyrazine derivatives (4–7) from the genus Atractylodes.
- Xu, Kuo,Yang, Ya-Nan,Feng, Zi-Ming,Jiang, Jian-Shuang,Zhang, Pei-Cheng
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p. 5187 - 5192
(2016/11/09)
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- Alkaloids and phenolic glycosides from Clematis mandshurica and their inhibitory effects against NO production in LPS-induced RAW 246.7 macrophages
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Two new alkaloids (1 and 2), one new phenolic glycoside (3), and five known structures (4–8) were isolated from the roots and rhizomes of Clematis mandshurica. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products
- Fu, Qiang,Chen, Jiang,Yuan, Hai-Mei,Ma, Yu,Yu, Tian,Zou, Liang
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p. 238 - 241
(2016/08/15)
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- Steroidal saponins and homoisoflavanone from the aerial parts of Sansevieria cylindrica Bojer ex Hook.
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Phytochemical study on the methanolic extract of Sansevieria cylindrica aerial parts lead to the isolation, characterization and structure elucidation of a new steroidal saponin, 1β-hydroxy-kryptogenin-1-O-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranoside (1), a new homoisoflavanone, (3S)-3,7-dihydroxy-8-methoxy-3-(3′,4′-methylenedioxybenzyl) chroman-4-one (2) and the known saponin alliospiroside A (3). To the best of our knowledge, the genin 1β-hydroxy-kryptogenin is reported here for the first time. The structures of the new compounds were determined by UV, IR, EIMS, HRESIMS together with 1D (1H and 13C) and 2D (HSQC and HMBC) NMR spectral analysis. The isolated compounds 1-3 were tested for their radical scavenging activity (DPPH). Compound 2 exhibited activity compared to that of ascorbic acid as a standard. The cytotoxicity of the isolated compounds and the standard doxorubicin was tested against the three human tumor cell lines HT116, MCF-7 and PC-3. The results showed that the isolated compounds were inactive.
- Said, Ataa,Aboutabl, Elsayed Ali,Melek, Farouk Rasmy,Abdel Jaleel, Gehad Abdel Raheem,Raslan, Mona
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p. 113 - 118
(2015/05/05)
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- Characterization and antitumor activities of a water-soluble polysaccharide from Ampelopsis megalophylla
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Abstract A water-soluble polysaccharide named as AMP was isolated and purified from the leaves of Ampelopsis megalophylla by DEAE-52 Cellulose and Sephadex G-100 column chromatography. AMP had an average molecular weight of about 8.4 × 104 Da and was composed of galactose (Gal), mannose (Man), glucose (Glc), arabinose (Ara), and rhamnose (Rha) in a molar ratio of 2.7:1.6:1.1:0.6:0.3. After 10 days of AMP (50, 100, and 200 mg/kg) treatment once daily in tumor-bearing mice, AMP oral administration could inhibit the growth of transplantable Sarcoma 180 (S180) tumor in mice and increase the spleen index and body weight. Furthermore, AMP also promote splenocytes' proliferation induced by concanavalin A (ConA) and lipopolysaccharide (LPS), strengthen peritoneal macrophages to devour neutral red and increase the production of interleukin-2 (IL-2), tumor necrosis factor-alpha (TNF-α), and interferon-gamma (IFN-γ) in serum. These results suggest that AMP had clear antitumor activity, which might be related to its regulation of immune function in mice.
- Xie, Xianfei,Wang, Jianwu,Zhang, Hanping
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- Flavonoids isolated from heat-processed Epimedium koreanum and their anti-HIV-1 activities
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Systematic phytochemical investigation on heat-processed Epimedium koreanum led to the isolation of 13 flavonoids, including five new prenyl-flavonol glycosides, koreanosides A-E (1-5, resp.). Their structures were elucidated on the basis of detailed analysis of the 1D- and 2D-NMR spectroscopic data and chemical reactions. Apigenin (11) exhibited moderate anti-HIV-1 activity with an EC50 value of 12.8±3.27 μg/ml.
- Li, Hong-Mei,Zhou, Cheng,Chen, Chin-Ho,Li, Rong-Tao,Lee, Kuo-Hsiung
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p. 1177 - 1187
(2015/08/24)
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- Novel steroidal glycosides from the bulbs of lilium pumilum
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Examination of the bulbs of Lilium pumilum (Liliaceae) led to the isolation of four novel steroidal glycosides (1-4) with a 2,3,4-trisubstituted β-D-glucopyranosyl unit. In 1 and 3, the α-L-arabinopyranosyl moiety is linked to C-3 of the inner trisubstituted β-D-glucopyranosyl group and is present as an usual 4C1 conformation. In contrast, in 2 and 4, the α-L-arabinopyranosyl moiety, which is attached to C-4 of the inner trisubstituted β-D-glucopyranosyl group, is present as a 1C4 conformation. The structures of the new steroidal glycosides were determined based on the results of spectroscopic analyses, including two-dimensional (2D) NMR data and hydrolysis.
- Matsuo, Yukiko,Takaku, Reina,Mimaki, Yoshihiro
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p. 16255 - 16265
(2015/12/01)
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- Dracopalmaside, a New Flavonoid from Dracocephalum palmatum
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Phytochemical studies of the aerial part of Dracocephalum palmatum (Lamiaceae) isolated the new flavonoid dracopalmaside that was identified based on UV, MS, and NMR spectral data as luteolin-7,4′-di-O-α -Lrhamnopyranosyl-(1→6)-β-D-glucopyranoside (luteolin-7,4′-di-O-rutinoside) and the two known compounds cynarotriside and luteolin-7,4′-di-O-glucoside.
- Olennikov,Chirikova
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p. 1067 - 1069
(2016/02/18)
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- Leptocarposide: A new triterpenoid glycoside from Ludwigia leptocarpa (Onagraceae)
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A new triterpenoid bidesmoside (leptocarposide) possessing an acyl group in their glycosidic moiety (1), together with the known luteolin-8-C-glucoside (2) and 1-O-β-D-glucopyranosyl-(2S,3R,8E)-2-[(R)-2-hydroxypalmitoylamino]-8- octadecen-1,3- diol (3) was isolated from the n-butanol-soluble fraction of whole plant of Ludwigia leptocarpa (Nutt) Hara (Onagraceae). Structure of compound 1 has been assigned on the basis of spectroscopic data (1H and 13C NMR, 1H-1H COSY, HSQC, HMBC, and ROESY), mass spectrometry, and by comparison with the literature. This compound was further screened for its potential antioxidant properties by using the radical scavenging assay model 2,2-diphenyl-1-picrylhydrazyl and reveals non-potent antioxidant activities, while compound 2 shows SC50 of 0,038 mM.
- Mabou, Florence Declaire,Tebou, Perrin Lanversin Foning,Ngnokam, David,Haraka, Dominique,Voutquenne-Nazabadioko, Laurence
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- Anti-inflammatory components of Euphorbia humifusa Willd.
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Two new compounds, euphorbinoside (1) and dehydropicrorhiza acid methyl diester (2), along with 24 known compounds (3-26) were isolated from Euphorbia humifusa Willd. The effects of these compounds on soluble epoxide hydrolase (sEH) inhibitory activity we
- Luyen, Bui Thi Thuy,Tai, Bui Huu,Thao, Nguyen Phuong,Eun, Kim Ji,Cha, Ji Yun,Xin, Ming Jie,Lee, Young Mi,Kim, Young Ho
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supporting information
p. 1895 - 1900
(2014/04/17)
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- Two new cytotoxic spirostane-steroidal saponins from the roots of bletilla striata
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Two new spirostane-steroidal saponins, bletilnoside A (1) and bletilnoside B (2), together with five known compounds, 3-7, were isolated from the roots of Bletilla striata (Thunb.) Reichb. F. The structures of the new compounds were determined based on their 1D- and 2D-NMR spectral data. The isolated compounds 1-7 were tested for cytotoxicity against four human tumor cells (A549, SK-OV-3, SK-MEL-2, and HCT15) in vitro using a sulforhodamin B bioassay, and compounds 1, 2, and 5 showed significant cytotoxicities against all tested tumor cell lines with IC50 values ranging from 3.98±0.16 to 12.10±0.40 μM. Copyright
- Park, Jong Eel,Woo, Kyeong Wan,Choi, Sang Un,Lee, Je Hyun,Lee, Kang Ro
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- Triterpene glycosides from the stems and leaves of Lonicera japonica
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Five new triterpene glycosides, namely lonicerosides F-J (1-5), together with five known ones, were isolated from the stems and leaves of Lonicera japonica. Based on extensive spectroscopic analysis, including twodimensional (2D)-NMR experiments, and the
- Kuroda, Minpei,Shizume, Takaaki,Mimaki, Yoshihiro
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- New phenolic glycosides from Pilea cavaleriei
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Five new phenolic glycosides, 2-hydroxy-(2'E)-prenyl benzoate-2,4'-di-O- β-Dglucopyranoside (1), 2-hydroxy-(2'E)-prenyl benzoate-2-O-α-L- arabinopyranosyl- (1 → 6)-β-D-glucopyranoside (2), 4-methylphenol-1-O-α-L-rhamnopyranosyl- (1 → 6)-β-D- glucopyranosi
- Zhou, Yong,Ren, Heng-Chun,Qin, Ri-Dong,Zhang, Qing-Ying,Liang, Hong
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p. 565 - 573
(2014/08/18)
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- Two new acylated flavonol glycosides from the seeds of Lepidium sativum
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Two new acylated flavonol glycosides named kaempferol-3-O-(2-O-sinapoyl)- β-D-galactopyranosyl-(1→2)-β-D-glucopyranoside-7-O-α-L- rhamnopyranoside (1) and quercetin-3-O-(6-O-benzoyl)-β-D-glucopyranosyl- (1→3)-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside
- Fan, Qing-Lu,Zhu, Yin-Di,Huang, Wen-Hua,Qi, Yun,Guo, Bao-Lin
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p. 11341 - 11349
(2014/11/08)
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- One new flavonoid xyloside and one new natural triterpene rhamnoside from the leaves of Syzygium grande
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One new flavonoid glycoside, myricetin 4′-methyl ether 3-O-β-d-xylopyranoside (1) and one new natural triterpene glycoside, grandoside (2) were isolated from a MeOH extract of the leaves of Syzygium grande, together with thirteen known compounds (3-15). The structures of the new compounds were determined through a combination of spectroscopic and chemical analyses. All of the isolated compounds were evaluated for their antifungal, antibacterial, anti-leishmania, DPPH radical-scavenging and cytotoxic activities by means of MTT assay.
- Samy, Mamdouh N.,Sugimoto, Sachiko,Matsunami, Katsuyoshi,Otsuka, Hideaki,Kamel, Mohamed S.
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