- Chemical structures of constituents from the seeds of Cassia auriculata
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Five new diterpene glycosides, auricuosides I (1), II (2), III (3), IV (4), and V (5), a new flavonol glycoside, auricuoflavonoside I (6), and a new megastigmane glycoside, auricuomegastigmane I (7), were isolated from the seeds of Cassia auriculata, together with 11 known constituents. The chemical structures of seven new constituents were characterized on the basis of chemical and physicochemical evidence. In the present study, auricuosides I (1)-V (5) were obtained from the seeds of C. auriculata. To the best of our knowledge, there is no report about the isolation of kaurenolides with hydroxy group at 14-position from plants. This finding is interesting from the perspective of chemotaxonomy and biosynthesis of kaurenolide.
- Zhang, Yi,Nakamura, Seikou,Nakashima, Souichi,Wang, Tao,Yoshikawa, Masayuki,Matsuda, Hisashi
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- The phenolic acids from Oplopanax elatus Nakai stems and their potential photo-damage prevention activity
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25 phenolic acids, including four new isolates, eurylophenosides A–D (1–4) and 21 known ones (5–25) were isolated and identified from the stems of Oplopanax elatus Nakai. Among the known compounds 5–9, 11–13, 16, 18–25 were isolated from the genus for the first time; 17 was first obtained from the plant; and the NMR data of 22 was reported here first. Meanwhile, the UVB-induced photodamage model of HaCaT cells was used to study the prevent-photodamage abilities of compounds 1–2, 4–8, 11–13 and 15–25 with a nontoxic concentration at 50?μM. Moreover, a dose-dependent experiment was conducted for active compounds at the concentration of 10, 25, and 50?μM, respectively. Consequently, pretreatment with compounds 1, 16, 17, 19, 20, 22, 24 and 25 could suppress the cell viability decreasing induced by UVB irradiation in a concentration-dependent manner. These results indicated that phenolic acids were one kind of material basis with prevent-photodamage activity of O. elatus. Graphic abstract: [Figure not available: see fulltext.].
- Han, Yu,Cheng, Dongsheng,Hao, Mimi,Yan, Jiejing,Ruan, Jingya,Han, Lifeng,Zhang, Yi,Wang, Tao
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- Bufadienolides and ecdysteroids from the whole plants of Helleborus niger and their cytotoxicity
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A new bufadienolide (1), two new bufadienolide glycosides (2 and 3), a new ecdysteroid (4), and four known compounds (5–8), were isolated from the whole plants of Helleborus niger L. (Ranunculaceae). The structures of the new compounds (1–4) were determined by spectroscopic analysis, including 2D NMR spectral data, and hydrolytic studies. Compounds 1–6 showed cytotoxicity against HL-60 human leukemia cells, A549 human lung adenocarcinoma cells, and SBC-3 human small-cell lung cancer cells, with IC50 values ranging from 0.0055 to 1.9?μM. HL-60 cells treated with either 3 or 4 showed apoptosis characteristics, such as nuclear chromatin condensation, accumulation of sub-G1 cells, and activation of caspase-3/7.
- Yokosuka, Akihito,Inomata, Mina,Yoshizawa, Yuka,Iguchi, Tomoki,Mimaki, Yoshihiro
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p. 393 - 402
(2021/01/29)
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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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- Phytochemical Study of Stem and Leaf of Clausena lansium
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Clausena lansium Lour. Skeels (Rutaceae) is widely distributed in South China and has historically been used as a traditional medicine in local healthcare systems. Although the characteristic components (carbazole alkaloids and coumarins) of C. lansium have been found to possess a wide variety of biological activities, little attention has been paid toward the other components of this plant. In the current study, phytochemical analysis of isolates from a water-soluble stem and leaf extract of C. lansium led to the identification of 12 compounds, including five aromatic glycosides, four sesquiterpene glycosides, two dihydrofuranocoumarin glycosides, and one adenosine. All compounds were isolated for the first time from the genus Clausena, including a new aromatic glycoside (1), a new dihydrofuranocoumarin glycoside (6), and two new sesquiterpene glycosides (8 and 9). The phytochemical structures of the isolates were elucidated using spectroscopic analyses including NMR and MS. The existence of these compounds demonstrates the taxonomic significance of C. lansium in the genus Clausena and suggests that some glycosides from this plant probably play a role in the anticancer activity of C. lansium to some extent.
- Peng, Wenwen,Fu, Xiaoxiang,Li, Yuyan,Xiong, Zhonghua,Shi, Xugen,Zhang, Fang,Huo, Guanghua,Li, Baotong
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- Phenolic Constituents from Fallopia multiflora (Thunberg) Haraldson
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Four naphtolic glycosides (1-4), three anthraquinones (5-7), two stilbenes (8-9), one benzyl glycoside (10), and one flavonoid (11) were isolated from the roots of Fallopia multiflora. The new compounds were elucidated to be 6-hydroxymusizin 8-O-α-D-apiof
- Nguyen, Thi Thoa,Pham, Thanh Binh,Thao, Nguyen Phuong,Dang, Nguyen Hai,Nguyen, Van Hung,Pham, Van Cuong,Minh, Chau Van,Tran, Quang Hai,Dat, Nguyen Tien
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- Naphthalene glycosides in the Thai medicinal plant Diospyros mollis
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This study evaluated methanol extracts from the leaves and branches of the Thai medicinal plant Diospyros mollis (Ebenaceae). Seven triterpenes and 22 aromatic compounds, including five new compounds, were isolated, and their structures were determined. The new compounds had the following structures: diospyrol glycoside (makluoside A, 1), 8,8′-di-O-6-β-d-apiofuranosyl-β-d-glucopyranosyl-6,6′-dimethyl-2,3′-binaphthalene-1-ol-1′,4′- dione (makluoside B, 2), and 3-methyl-1,8- naphthalenediol glycosides (makluosides C-E, 3–5). Makluoside B is the first example of a naphthoquinone glycoside that has both a 3-methyl-1,8-naphthalenediol unit and a 5-hydroxy-7-methyl-1,4-naphthoquinone unit. The hyaluronidase inhibitory activity of the isolates was evaluated, revealing that one of the triterpene derivatives possessed moderate inhibitory activity.
- Suwama, Takaharu,Watanabe, Keisuke,Monthakantirat, Orawan,Luecha, Prathan,Noguchi, Hiroshi,Watanabe, Kenji,Umehara, Kaoru
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p. 220 - 229
(2017/10/17)
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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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- From the stems of Hydrangea paniculata Sieb
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known compounds (4, 5), have been isolated from the stems of Hydrangea paniculata Sieb. Their structures have been determined by spectroscopic and chemical methods. Furthermore, compound 1 (50 μM) exhibited significant hepatoprotective activity against N-
- Ma, Jie,Li, Chuang-Jun,Yang, Jing-Zhi,Sun, Hua,Zhang, Dong-Ming
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- The antitumor constituents from hedyotis diffusa willd
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As a TCM, Hedyotis diffusa Willd. has been using to treat malignant tumors, and many studies also showed that the extracts from Hedyotis diffusa Willd. possessed evident antitumor activities. Therefore, we carried out chemical study on Hedyotis diffusa Willd. and investigated the cytotoxicity of the obtained compounds on a panel of eight tumor cell lines. As a result, four new compounds were isolated from Hedyotis diffusa Willd., including three iridoid glycosides of Shecaoiridoidside A-C (1-3) and a cerebroside of shecaocerenoside A (4). Also, six known iridoid compounds (5-10) were also obtained. The cytotoxicity of all compounds against human tumor cell lines of HL-60, HeLa, HCT15, A459, HepG2, PC-3, CNE-2, and BCG-823 were also evaluated in vitro. New compound 3 exhibited evident cytotoxicity to all tumor cell lines except the Hela, and the IC50 values are from 9.6 μ M to 62.2 μ M, while new compound 4 showed moderate cytotoxicity to all the cell lines, and the IC50 values are from 33.6 μ M to 89.3 μ M. By contrast, new compound 1 and known compound 9 showed moderate cytotoxicity to HCT15, A459, and HepG2 selectively. Known compound 7 also exhibited moderate cytotoxicity to HCT15 and A459 selectively.
- Wang, Changfu,Zhou, Xuegang,Wang, Youzhi,Wei, Donghua,Deng, Chengjie,Xu, Xiaoyun,Xin, Ping,Sun, Shiqin
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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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- Efficient chemoenzymatic synthesis of 4-nitrophenyl β-d-apiofuranoside and its use in screening of β-d-apiofuranosidases
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4-Nitrophenyl β-d-apiofuranoside as a chromogenic probe for detection of β-d-apiofuranosidase activity was prepared in 61% yield from 2,3-isopropylidene-α,β-d-apiofuranose through a sequence of five reactions. The synthesis involves one regioselective enz
- Kis, Peter,Potocká, Elena,Mastihuba, Vladimír,Mastihubová, Mária
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- Seven New Acyl Glycosides from Erycibe obtusifolia
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Seven new acyl glycosides, benzyl 5-O-vanilloyl-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (1), 4-hydroxy-3-methoxyphenyl 5-O-syringoyl-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (2), isopentyl 5-O-syringoyl-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (3), 3,4,5-trimethoxyphenyl 5-O-sinapoyl-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (4), 6-methoxy-7-[(6-O-sinapoyl-β-d-glucopyranosyl)oxy]coumarin (5), 6-methoxy-7-[(2-O-sinapoyl-β-d-glucopyranosyl)oxy]coumarin (6), and isopentyl β-d-apiofuranosyl-(1→6)-[5-O-syringoyl-β-d-apiofuranosyl-(1→2)]-β-d-glucopyranoside (7), were isolated from Chinese folk herb Erycibe obtusifolia. Their structures were elucidated on the basis of extensive spectroscopic analysis, including UV, IR, MS, and 1D- and 2D-NMR techniques. Further, these compounds were evaluated against HCT-8 (human colon carcinoma), Bel-7402 (human liver carcinoma), BGC-823 (human stomach carcinoma), A549 (human lung carcinoma), and A2780 (human ovarian carcinoma) cell lines, however, none of them exhibited a significant bioactivity (IC50 > 10 μm).
- Feng, Zi-Ming,Liu, Zhao-Zhen,Xu, Kuo,Yang, Ya-Nan,Jiang, Jian-Shuang,Zhang, Pei-Cheng
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p. 197 - 203
(2016/04/19)
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- Crotocascarins I-K: Crotofolane-type diterpenoids, crotocascarin γ, isocrotofolane glucoside and phenolic glycoside from the leaves of croton cascarilloides
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From the 1-BuOH-soluble fraction of a methanol (MeOH) extract of the leaves of Croton cascarilloides, crotofolanes: crotocascarins I-K, nor-crotofolane: crotocascarin γ, isocrotofolane glucoside and phenolic glycoside were isolated by a combination of various separation techniques. Their structures were elucidated mainly from the NMR spectroscopic evidence. The structure of crotocascarin K was first elucidated by spectroscopic analysis and then was confirmed by X-ray crystallographic analysis. Its absolute structure was finally determined by the modified Mosher's method. Isocrotofolane glucoside was found to possess a new skeleton, however, its absolute structure remains to be determined.
- Kawakami, Susumu,Matsunami, Katsuyoshi,Otsuka, Hideaki,Inagaki, Masanori,Takeda, Yoshio,Kawahata, Masatoshi,Yamaguchi, Kentaro
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p. 1047 - 1054
(2016/02/03)
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- Antineuroinflammatory and antiproliferative activities of constituents from Tilia amurensis
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As part of our ongoing search for bioactive constituents of natural Korean medicinal resources, we found in a preliminary study that the methanol (MeOH) extract from the trunks of Tilia amurensis RUPR. showed an inhibitory effect on nitric oxide (NO) production in an activated murine microglial cell line. A bioassayguided fractionation and chemical investigation of the MeOH extract resulted in the isolation and identification of a new isoflavonoid glycoside, orobol 4'-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (1) and 16 known compounds (2-17). The structure of the new compound was determined by spectroscopic methods, i.e., one-dimensional (1D) and two-dimensional (2D)-NMR techniques and high resolution (HR)-MS, and chemical methods. The antineuroinflammatory activities of the isolated compounds were determined by measuring NO levels in the medium using murine microglial BV-2 cells. Among them, 12 compounds, including compound 1 (most active with an IC50 value of 23.42 μm), inhibited NO production in lipopolysaccharidestimulated BV-2 cells. Moreover, compounds 1-4 showed moderate antiproliferative activities against the SK-MEL-2 cell line, with IC50 values ranging from 12.31 to 19.67 μM.
- Kim, Ki Hyun,Moon, Eunjung,Cha, Joon Min,Lee, Seulah,Yu, Jae Sik,Kim, Chung Sub,Kim, Sun Yeou,Choi, Sang Un,Lee, Kang Ro
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p. 837 - 842
(2015/11/27)
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- Chemical constituents of Miliusa balansae leaves and inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 cells
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Abstract Methanolic extract of Miliusa balansae Finet et Gagnep exerts an anti-inflammatory effect via inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophage cells. Three new megastigmane glycosides, milbasides A-C (1-3), together with fifteen known compounds (4-18), were isolated from the active fraction. Their chemical structures were elucidated using extensive spectroscopic analyses, including 1D and 2D NMR, HR ESI MS, and CD analysis, as well as comparison with previously reported data. Compounds 1-3, 11 and 14 (20.0 μM) showed potent inhibitory activities with inhibition values of 98.5 ± 1.6%, 90.9 ± 7.8%, 84.8 ± 3.5%, 91.5 ± 8.7%, and 91.8 ± 2.7%, respectively. Our results suggest that megastigmane glycosides from M. balansae leaves may be used to treat inflammatory diseases.
- Thao, Nguyen Phuong,Luyen, Bui Thi Thuy,Tai, Bui Huu,Cuong, Nguyen Manh,Kim, Youn Chul,Minh, Chau Van,Kim, Young Ho
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supporting information
p. 3859 - 3863
(2015/08/24)
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- A new cyclolignan glycoside from the tubers of Pinellia ternata
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A new 2,7′-type cyclolignan glycoside, cyclolignanyingoside A (1), together with six known compounds (2-7) were isolated from the tubers of Pinellia ternata (Thunb.) Breit. The structure of 1 was elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses, HR-ESI-MS, and CD spectrometry. The cytotoxic, antioxidant and tyrosinase-inhibiting activities of all the isolates were determined. However, all the isolates exhibited no activity on the selected cell lines (Hep-3B, Bcap-37, and MCF-7). In addition, compounds 1-3 and 7 exhibited strong 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) free radical scavenging activity, and compounds 2 and 4 showed a moderate mushroom tyrsinase inhibitory activity.
- Wu, Ying-Ying,Huang, Xiao-Xiao,Wu, Jie,Zhou, Le,Li, Dan-Qi,Liu, Qing-Bo,Li, Ling-Zhi,Yan, Xin-Jia,Song, Shao-Jiang
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p. 1097 - 1103
(2015/11/18)
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- NF-κB inhibitory activities of glycosides and alkaloids from zanthoxylum schinifolium stems
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Zanthoxylum schinifolium is an aromatic shrub, the pericarp and leaves of which are widely used in culinary applications in East Asian countries. In the present study, one new neolignan glycoside, zanthoxyloside A (1) together with 16 known glycosides (2-12) and alkaloids (13-17), were isolated from methanol extract of the stems of Z. schinifolium. The absolute configuration of one known monoterpenoid glycoside (2) was determined. The structures of the isolated compounds were established by one dimensional (1D), 2D NMR and mass spectrometry. The nuclear factor-κB (NF-κB) inhibitory activities of the isolated compounds stimulated with tumor necrosis factor alpha (TNFa) were measured using a luciferase reporter system. Compounds 1, 5, 16, and 17 exhibited significant inhibition of NF-κB activation in a dose-dependent manner. Furthermore, compounds 1, 5, 16, and 17 inhibited TNFa-induced expression of inducible nitric oxide synthase (iNOS) and intercellular adhesion molecule-1 (ICAM-1) mRNA and dose-dependent inhibition of iNOS promoter activity.
- Li, Wei,Yang, Seo Young,Yan, Xi Tao,Sun, Ya Nan,Song, Seok Bean,Kang, Hee Kyoung,Kim, Young Ho
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p. 196 - 202
(2014/03/21)
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- A new phenolic glycoside from the barks of Cinnamomum cassia
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A new phenolic glycoside (1), named methyl 2-phenylpropanoate-2-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranoside, was isolated from the barks of Cinnamomum cassia, along with three known phenolic glycosides and four known lignan glycosides. The structure of 1 was elucidated by extensive interpretation of spectroscopic data and chemical method. Selected compounds were evaluated for their immunosuppressive activities against murine lymphocytes. Compounds 1, 2, 6 and 8 exhibited differential inhibition against ConA-induced T cells proliferation.
- Zeng, Junfen,Xue, Yongbo,Lai, Yongji,Yao, Guangmin,Luo, Zengwei,Zhang, Yonghui,Zhang, Jinwen
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p. 17727 - 17734
(2015/01/09)
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- Two new glycosides from Duboscia macrocarpa Bocq.
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Two new compounds namely dubosciasides A (1) and B (2) were isolated from stem bark of Duboscia macrocarpa Bocq. together with three known flavonoids. Their structures were determined by spectroscopic methods including one- and two-dimensional NMR, EIMS and HRESIMS. The new compounds were identified as 6-C-β-d-apiofuranosyl-(1 → 4)-β-d-galactopyranosylnaringetol (1) and 1-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-xylopyranosyl-3,4,5-trimethoxyphenol (2).
- Tchuendem, Marguerite H.K.,Douanla, Pascal D.,Tabopda, Turibio K.,Tchinda, Alembert T.,Tamze, Véronique,Nkengfack, Augustin E.,Abegaz, Berhanu M.,Connolly, Joseph D.
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- Hepatoprotective acyl glycosides obtained from Erycibe hainanesis
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An ongoing search for naturally occurring hepatoprotective constituents has identified three new acyl glycosides (1-3) and a new lignan glycoside (4) in the roots and stems of Erycibe hainanesis using various column chromatography methods. The structures of these compounds have been determined based on chemical and spectroscopic evidence, and the following bioassay indicates that all four glycosides have moderate hepatoprotective activities against d-galactosamine induced toxicity in WB-F344 rat hepatic epithelial stem-like cells.
- Feng, Ziming,Song, Shuang,An, Yawen,Yang, Yanan,Jiang, Jianshuang,Zhang, Peicheng
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p. 163 - 167
(2014/08/05)
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- A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity
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Two new compounds, piperoside (1) and isoheptanol 2(S)-O-β-d- xylopyranosyl (1→6)-O-β-d-glucopyranoside (11), along with 10 known compounds 3,4-dihydroxyallylbenzene (2), 1,2-di-O-β-d-glucopyranosyl-4- allylbenzene (3), tachioside (4), benzyl-O-β-d-glucopyranoside (5), icariside F2 (6), dihydrovomifoliol-3′-O-β-d- glucopyranoside (7), isopropyl O-β-d-glucopyranoside (8), isopropyl primeveroside (9), n-butyl O-β-d-glucopyranoside (10), isoheptanol 2(S)-O-β-d-apiofuranosyl-(1→6)-O-β-d-glucopyranoside (12), were isolated from the leaves of Piper retrofractum. Their structures were determined from 1D-NMR, 2D-NMR, and HR-ESI-MS spectral, a modified Mosher's method, and comparisons with previous reports. All of the isolated compounds showed modest α-glucosidase inhibitory (4.60 ± 1.74% to 11.97 ± 3.30%) and antioxidant activities under the tested conditions.
- Luyen, Bui Thi Thuy,Tai, Bui Huu,Thao, Nguyen Phuong,Yang, Seo Young,Cuong, Nguyen Manh,Kwon, Young In,Jang, Hae Dong,Kim, Young Ho
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supporting information
p. 4120 - 4124
(2014/11/27)
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- Two new glycosides from Duboscia macrocarpa Bocq.
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Two new compounds namely dubosciasides A (1) and B (2) were isolated from stem bark of Duboscia macrocarpa Bocq. together with three known flavonoids. Their structures were determined by spectroscopic methods including one- and two-dimensional NMR, EIMS and HRESIMS. The new compounds were identified as 6-C-β-d-apiofuranosyl-(1 → 4)-β-d-galactopyranosylnaringetol (1) and 1-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-xylopyranosyl-3,4,5- trimethoxyphenol (2).
- Tchuendem, Marguerite H.K.,Douanla, Pascal D.,Tabopda, Turibio K.,Tchinda, Alembert T.,Tamze, Véronique,Nkengfack, Augustin E.,Abegaz, Berhanu M.,Connolly, Joseph D.
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- Diterpenoids and phenylethanoid glycosides from the roots of Clerodendrum bungei and their inhibitory effects against angiotensin converting enzyme and α-glucosidase
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Abietane derivatives, bungnates A, B, 15-dehydrocyrtophyllone A and 15-dehydro-17-hydroxycyrtophyllone A, and two phenylethanoid glycosides, bunginoside A and 3″,4″-di-O-acetylmartynoside, together with nine known abietane derivatives and fourteen known phenylethanoid glycosides, were isolated from dried roots of Clerodendrum bungei. Their structures were determined on the basis of detailed spectroscopic analyses and acidic hydrolysis. The absolute configuration of bunginoside A was established from analysis of CD data. Selected compounds were evaluated for inhibitory effects against angiotensin converting enzyme (ACE) and α-glucosidase. 15-Dehydrocyrtophyllone A showed an ACE inhibitory effect, and verbascoside, leucosceptoside A and isoacteoside exhibited strong inhibitory capacity against α-glucosidase.
- Liu, Qing,Hu, Hai-Jun,Li, Peng-Fei,Yang, Ying-Bo,Wu, Li-Hong,Chou, Gui-Xin,Wang, Zheng-Tao
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p. 196 - 202
(2014/06/09)
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- Six new steroidal saponins from helleborus thibetanus
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Six steroidal saponins, including five spirostanol glycosides, 1 - 5, and one furostanol glycoside 1- sulfonate, 6, previously unknown in nature, together with three known compounds, 7 - 9, were isolated from dried roots and rhizomes of Helleborus thibetanus. Their structures were elucidated by extensive 1D- And 2D-NMR experiments, along with IR and HR-ESI-MS data, as well as the results of acid hydrolysis. Compounds 1 - 5 possessed a C(25)=C(27) bond and were glycosylated at HO-C(1), which was unusual in steroidal saponins.
- Zhang, Hui,Su, Yan-Fang,Yang, Feng-Ying,Zhao, Ze-Qing,Gao, Xiu-Mei
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p. 1652 - 1665
(2015/02/19)
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- Chemical constituents isolated from Disporum viridescens leaves and their inhibitory effect on nitric oxide production in BV2 microglial cells
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Excessive NO (nitric oxide) has been associated with the pathogenesis of various neurodegenerative diseases including Alzheimer's disease (AD). In our screening system using LPS-activated BV2 microglial cells, the methanolic extract of Disporum viridescen
- Cho, Namki,Yang, Heejung,Kim, Jung Wha,Kim, Young Choong,Sung, Sang Hyun
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p. 5675 - 5678
(2015/01/08)
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- Schoepfiajasmins A-H: C-glycosyl dihydrochalcones, dihydrochalcone glycoside, C-glucosyl flavanones, flavanone glycoside and flavone glycoside from the branches of schoepfia jasminodora
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From the branches of Schoepfia jasminodora collected in Okinawa, three new dihydrochalcone C-glycosides, one dihydrochalcone di-O-glucopyranoside, two flavanone C-glycosides, one flavanone O-glycoside and one flavone O-glycoside were isolated. Their structures were elucidated by extensive study of one- and twodimensional NMR spectroscopic data.
- Ukida, Kouki,Doi, Takashi,Sugimoto, Sachiko,Matsunami, Katsuyoshi,Otsuka, Hideaki,Takeda, Yoshio
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p. 1136 - 1142
(2014/01/06)
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- Four new glycosides from the fruit of Xanthium sibiricum patr.
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Four new glycosides, namely 3β-norpinan-2-one 3-O-β-D- apiofuranosyl-(1→6)-β-D-glucopyranoside (1), (6Z)-3-hydroxymethyl-7- methylocta-1,6-dien-3-ol 8-O-β-Dglucopyranoside (2), (6E)-3-hydroxymethyl- 7-methylocta-1,6-dien-3-ol 8-O-β-D-glucopyranoside (3),
- Jiang, Hai,Yang, Liu,Liu, Chang,Hou, Hui,Wang, Qiuhong,Wang, Zhibin,Yang, Bingyou,Kuang, Haixue
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p. 12464 - 12473
(2013/11/06)
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- Acyl glycosides with rare β-d-apiofuranosyl-β-d-glucopyranosyl- β-d-apiofuranosyl from Erycibe hainanesis
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Three new acyl glycosides with rare β-d-apiofuranosyl-(1 → 2)-[β-d-apiofuranosyl-(1 → 6)]-β-d-glucopyranosyl moieties, 2-O-[2,6-O-bis(5-O-syringoyl-β-d-apiofuranosyl)-β-d-glucopyranosyl] -isopropyl alcohol (1), 1-O-[2,6-O-bis(5-O-syringoyl-β-d-apiofuranos
- Feng, Zi-Ming,Song, Shuang,He, Jun,Yang, Ya-Nan,Jiang, Jian-Shuang,Zhang, Pei-Cheng
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- Inhibitory constituents from the aerial parts of Polygala tenuifolia on LPS-induced NO production in BV2 microglia cells in commemoration of Professor Xin-Sheng Yao's 80th Birthday
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Five new phenolic glycosides, tenuisides A-E (1-5), and a new megastigmane glycoside, tenuiside F (6), along with seventeen known compounds (7-23) were isolated from the aerial parts of Polygala tenuifolia Willd. Their structures were established by detailed analysis of NMR and HRESIMS spectroscopic data, and the absolute configurations of compounds 5 and 6 were determined by CD spectra and in-NMR-tube Mosher's method. The inhibitory effects of these compounds were evaluated on NO production in LPS-activated BV-2 microglia cells. Compound 17 showed the strongest activity, with an IC50 value of 7.4 μM, while compounds 1, 8, 14, and 18 showed the moderate activities, with IC50 values of 16.2-38.5 μM. And their primary structure-activity relationships (SARs) of NO inhibitory effects were also briefly discussed.
- Shi, Tian-Xing,Wang, Shu,Zeng, Ke-Wu,Tu, Peng-Fei,Jiang, Yong
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supporting information
p. 5904 - 5908
(2013/10/22)
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- Five new phenolic glycosides from Hedyotis scandens
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Five new phenolic glycosides, hedyotosides A-E (1-5), including a new cyanogenic glycoside (1), along with 10 known compounds (6-15) were isolated from the whole plants of Hedyotis scandens. The structures of compounds 1-5 were established by extensive spectroscopic analyses and acid hydrolysis. All the isolated compounds were evaluated for their in vitro antiviral activity against respiratory syncytial virus (RSV) with cytopathic effect (CPE) reduction assay. Compounds 6 and 15 showed anti-RSV effects with IC50 values of 20 and 25 μg/mL, respectively.
- Wang, Guo-Cai,Li, Tao,Deng, Fang-Ye,Li, Yao-Lan,Ye, Wen-Cai
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p. 1379 - 1382
(2013/03/14)
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- Identification of compounds from the water soluble extract of cinnamomum cassia barks and their inhibitory effects against high-glucose-induced mesangial cells
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The difficulty of diabetic nephropathy (DN) treatment makes prevention the best choice. Cinnamomum cassia barks, known as Chinese cinnamon or Chinese cassia, is one of the most popular natural spices and flavoring agents in many parts of the World. Since
- Luo, Qi,Wang, Shu-Mei,Lu, Qing,Luo, Jie,Cheng, Yong-Xian
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p. 10930 - 10943
(2013/10/22)
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- Bioactivity of diosmetin glycosides isolated from the epicarp of date fruits, Phoenix dactylifera, on the biochemical profile of alloxan diabetic male rats
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The new natural flavonoid compounds - diosmetin 7-O-β-L- arabinofuranosyl (1 → 2) β-D-apiofuranoside (1) and diosmetin 7-O-β-D-apiofuranoside (2) - were isolated from the acetone extract of date fruits epicarp belonging to family Arecaceae (Palmae). Elucidation of their chemical structures was determined by different spectroscopic methods in addition to the chemical and physical methods of analysis. These compounds were assessed for their biological activity on alloxan diabetic rats. A dose of 1.5 ml of (1) and (2) suspensions/100 gm b. wt were orally administrated to alloxan diabetic rats for 30 days. The treatment of diabetic rats with these compounds resulted in marked improvement of the different biochemical results, i.e. The serum glucose level (highly significant, from 330 + 5.5 mg/dL to 140 + 1.2 mg/dL) treated with (1); liver functions markedly developed both by AST and ALT levels, (reduced significantly from 68.3 + 4.8 μ/L to 54 + 5.5 μ/L and from 61.0 + 3.6 μ/L to 40.1 + 3.6 μ/L, respectively) treated with (2), accompanying with mild decrease in both cholesterol and triglycerides levels with (1) or (2). Decrease of TBARS level was observed in whole blood when treated with (1) or (2), while levels of glutathione peroxidase and superoxide dismutase were increased in liver. Serum testosterone level was highly significantly increased (from 705.1 + 3.6 mg/100 ml to 720 + 4.7 mg/100 ml), total acid phosphatase and prostate acid phosphatase activities were highly significantly decreased (from 16.9 + 0.28 μ/L to 10.7 + 1.2 μ/L and from 9.7 + 0.7 μ/L to 6.5 + 1 μ/L, respectively) for compound (1). Copyright
- Michael, Helana Naguib,Salib, Josline Yehia,Eskander, Emad Fawzi
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p. 699 - 704
(2013/06/26)
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- Oblongionosides A-F, megastigmane glycosides from the leaves of Croton oblongifolius Roxburgh
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From the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Croton oblongifolius Roxburgh, collected in Chiang Mai, Thailand, six megastigmane glycosides, named oblongionosides A-F were isolated together with eight known compounds, and their structures elucidated on the basis of spectroscopic data. Absolute structures were determined by HPLC analyses and application of the modified Mosher's method.
- Takeshige, Yuya,Kawakami, Susumu,Matsunami, Katsuyoshi,Otsuka, Hideaki,Lhieochaiphant, Duangporn,Lhieochaiphant, Sorasak
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experimental part
p. 132 - 136
(2012/08/27)
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- Steroidal saponins from Paris polyphylla var. yunnanensis
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Eleven steroidal saponins, along with seven known steroidal saponins, were isolated from rhizomes of Paris polyphylla var. yunnanensis. Their chemical structures were elucidated on the basis of spectroscopic analyses and acid hydrolysis. Two of these compounds contained a spirostanol saponin aglycone, hitherto unknown in Nature. The isolated compounds were tested for their cytotoxic effects on human nasopharyngeal carcinoma epithelial (CNE) cells, and seven compounds displayed more potent inhibitory effects than cisplatin (the positive control). One compound with diosgenin and tetrasaccharide moieties possessed the strongest inhibitory effect on CNE cells through the induction of apoptosis and cell cycle arrest.
- Wu, Xia,Wang, Lei,Wang, Hui,Dai, Yi,Ye, Wen-Cai,Li, Yao-Lan
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experimental part
p. 133 - 143
(2012/10/08)
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- Xanthine oxidase inhibitory activity of constituents of Cinnamomum cassia twigs
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A methanol extract of the twigs of Cinnamomum cassia was found to inhibit xanthine oxidase. Purification of the methanol extract afforded three new phenolic glycosides, cinnacasolide A-C (11-13), together with 10 known compounds (1-10). The structures of
- Ngoc, Tran Minh,Khoi, Nguyen Minh,Ha, Do Thi,Nhiem, Nguyen Xuan,Tai, Bui Huu,Don, Dao Van,Luong, Hoang Van,Son, Doan Cao,Bae, Kihwan
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experimental part
p. 4625 - 4628
(2012/08/13)
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- Antiparasitic antioxidant phenylpropanoids and iridoid glycosides from Tecoma mollis
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A radical scavenging guided phytochemical study on the stem bark of Tecoma mollis afforded seven active phenylpropanoid glycosides (1-7), including a new one (4), and one iridoid (8). The structures of the isolated compounds were elucidated on the basis of spectroscopic evidences and correlated with known compounds. Compounds (1-7) displayed promising antioxidant activity (DPPH assay) in relation to ascorbic acid (positive control). The antimicrobial activity for compounds (1-8) was evaluated against five bacterial and five fungal strains. The isolated compounds exhibited nonselective weak to moderate antimicrobial activity. The highest antileishmanial activity against Leishmania donovani was observed for compound (7) with an IC50 value of 6.71 μg/ml, using pentamidine and amphotericin B as drug controls. Compound (5) exhibited moderate antimalarial activity (45% inhibition) against chloroquine sensitive (D6) clones of Plasmodium falciparum.
- Abdel-Mageed, Wael M.,Backheet, Enaam Y.,Khalifa, Azza A.,Ibraheim, Zedan Z.,Ross, Samir A.
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experimental part
p. 500 - 507
(2012/07/13)
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- A new triterpenoid and a new glycoside from Pilea cavaleriei
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A new triterpenoid, 11α,12α-epoxy-3β-hydroxy-24-nor-olean- 4(23)-en-28,13β-olide (1), and a new glycoside, benzyl 2-O-β-d- apiofuranosyl-(1 → 2)-β-d-glucopyranosyl benzoate (2), together with eight known triterpenoids (3-10), were isolated from Pilea cavaleriei subsp. cavaleriei. Their structures were established on the basis of spectroscopic analysis including HR-ESI-MS, 1D NMR, and 2D NMR techniques. All compounds showed no anti-hepatitis C virus activity.
- Ren, Heng-Chun,Qin, Ri-Dong,Wang, Qi,Cheng, Wei,Zhang, Qing-Ying,Liang, Hong
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p. 1032 - 1038
(2013/03/13)
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- Phenolic glycosides from sugar maple (Acer saccharum) bark
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Four new phenolic glycosides, saccharumosides A-D (1-4), along with eight known phenolic glycosides, were isolated from the bark of sugar maple (Acer saccharum). The structures of 1-4 were elucidated on the basis of spectroscopic data analysis. All compounds isolated were evaluated for cytotoxicity effects against human colon tumorigenic (HCT-116 and Caco-2) and nontumorigenic (CCD-18Co) cell lines.
- Yuan, Tao,Wan, Chunpeng,Gonzalez-Sarrias, Antonio,Kandhi, Vamsikrishna,Cech, Nadja B.,Seeram, Navindra P.
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experimental part
p. 2472 - 2476
(2012/02/01)
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- Antioxidant activity of a new C-glycosylflavone from the leaves of Ficus microcarpa
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By bioactive-guided fractionation of methanol extract of the Ficus microcarpa leaves, one new C-glucosylflavone, ficuflavoside (1), one new megastigmane glycoside, ficumegasoside (8), and twelve known compounds including flavonoids (2-6), phenylpropanoids (7), megastigmanes (9-11) and sterol derivatives (12-14) were isolated. Their chemical structures were elucidated by mass, 1D, and 2D NMR spectroscopies. The antioxidant activities of these compounds were measured using the oxygen radical absorbance capacity methods. Compounds 1-6 exhibited potent antioxidant activities of 6.6-9.5 μM Trolox equivalents at the concentration of 2.0 μM. The results indicated 2, 3, and 5 having meaningful reducing capacity of copper (I) ions concentration of 6.1-8.4 μM.
- Kiem, Phan Van,Cuong, Nguyen Xuan,Nhiem, Nguyen Xuan,Thu, Vu Kim,Ban, Ninh Khac,Minh, Chau Van,Tai, Bui Huu,Hai, Truong Nam,Lee, Sang Hyun,Jang, Hae Dong,Kim, Young Ho
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experimental part
p. 633 - 637
(2011/02/27)
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- Unusual oleanane-type saponins from Arenaria montana
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Three oleanane-type saponins, 3-O-β-d-glucopyranosylechinocystic acid 28-O-β-d-xylopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→2)] -α-l-rhamnopyranosyl ester (1), 3-O-β-d-glucopyranosylechinocystic acid 28-O-α-l-arabinopyranosyl-(1→3)-β-d-xylopyranosyl- (1→4)-[α-l-rhamnopyranosyl-(1→2)]-α-l-rhamnopyranosyl ester (2), 3-O-β-d-glucopyranosylcaulophyllogenin 28-O-β-d- apiofuranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-[β-d- apiofuranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2) -α-l-rhamnopyranosyl ester (3) were isolated from the whole plant of Arenaria montana. Their unusual structures for the Caryophyllaceae family were established mainly by 2D NMR techniques and mass spectrometry.
- Timité, Gaoussou,Mitaine-Offer, Anne-Claire,Miyamoto, Tomofumi,Tanaka, Chiaki,Mirjolet, Jean-Franois,Duchamp, Olivier,Lacaille-Dubois, Marie-Aleth
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experimental part
p. 503 - 507
(2012/05/04)
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- Crotonionosides A-G: Megastigmane glycosides from leaves of Croton cascarilloides R?uschel
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From the 1-BuOH-soluble fraction of a MeOH extract of leaves of Croton cascarilloides, collected in Okinawa, Japan, seven megastigmane glycosides, named crotonionosides A-G, were isolated together with three known megastigmane glucosides, dendranthemosides A and B, and citroside A. This structures were elucidated by a combination of spectroscopic analyses, HPLC analyses, and application of the modified Mosher's method.
- Kawakami, Susumu,Matsunami, Katsuyoshi,Otsuka, Hideaki,Shinzato, Takakazu,Takeda, Yoshio
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experimental part
p. 147 - 153
(2011/10/08)
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- Two new iridoid glycosides from the root barks of Sambucus williamsii Hance
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Chemical investigation of the ethanol extract of the root barks of Sambucus williamsii Hance collected in the Heilongjiang province of China resulted in the isolation of two new iridoid glycosides, williamsoside A (1) and williamsoside B (2). Their structures were elucidated on the basis of extensive spectroscopic analysis (1D, 2D-NMR and HRESIMS) and chemical studies. Iridoid glycosides have for a long time been considered as characteristic ingredients of S. williamsii. However, the presence of iridoid glycosides with apiofuranosyl moieties in S. williamsii is reported for the first time in this study.
- Wang, Zhen-Yue,Han, Hua,Yang, Bing-You,Xia, Yong-Gang,Kuang, Hai-Xue
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experimental part
p. 3869 - 3874
(2011/07/30)
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- A novel 8,4′-oxyneolignan diglycoside from Ligusticum sinensis
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A novel 8,4′-oxyneolignan diglycoside, named ligusinenoside d (1), was isolated from the rhizomes of Ligusticum sinensis, together with five known analogues 2-6. The absolute configurations of 1 and 2 were elucidated by means of enzymatic hydrolysis and spectroscopic data.
- Ma, Jian Ping,Tan, Chang Heng,Zhu, Da Yuan,Jin, Ling
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experimental part
p. 1454 - 1456
(2012/06/01)
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- Two new C-glycosylflavones from Boea hygrometrica
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Two new C-glycosylflavones, named 5,7,3′,4′-tetrahydroxy-6- methoxy-8-C-β-Dgluco-pyranosyl flavonoside (1), 5,3′,4′- trihydroxy-6,7-dimethoxy-8-C-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranosyl flavonoside (2), together with nine known compounds (3-11), were isolated from 50% acetone extract of Boea hygrometrica (Bunge.) R.Br. Their structures were established by spectroscopic techniques including MS, IR, UV, and 2D NMR.
- Feng, Wei-Sheng,Li, Yuan-Jing,Zheng, Xiao-Ke,Wang, Yan-Zhi,Su, Fang-Yi,Pei, Yuan-Yuan
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experimental part
p. 618 - 623
(2011/10/04)
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- New Hedgehog/GLI signaling inhibitors from Excoecaria agallocha
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The inhibition of the Hedgehog (Hh) signaling pathway has emerged as an anti-cancer strategy. Three flavonoid glycosides including 2 new compounds (1-2) were isolated from Excoecaria agallocha as Hedgehog/GLI1-mediated transcriptional inhibitors and exhibited cytotoxicity against human pancreatic (PANC1) and prostate (DU145) cancer cells. Our data revealed that compound 1 clearly inhibited the expression of GLI-related proteins (PTCH and BCL-2) and blocked the translocation of GLI1 transcription factors into the nucleus in PANC1. Deleting the Smoothened (Smo) function in PANC1 treated with 1 led to downregulation of the mRNA expression of Ptch. This study describes the first Hh signaling inhibitor which blocks GLI1 movement into the nucleus without interfering with Smo.
- Rifai, Yusnita,Arai, Midori A.,Sadhu, Samir K.,Ahmed, Firoj,Ishibashi, Masami
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supporting information; experimental part
p. 718 - 722
(2011/03/18)
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- Two new lignan glycosides from the seeds of Cuscuta chinensis
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Two new lignan glycosides, 2'-hydroxyl asarinin 2'-O-β-D- glucopyranoside (cuscutoside C, 1) and 2'-hydroxyl asarinin 2'-O-β-D- apiofuranosyl-(1→2)-[-D-glucopyranosyl-(1→6)]-D-glucopyranoside (cuscutoside D, 2), were isolated from the seeds of Cuscuta chinensis Lam., along with six known compounds, 2'-hydroxyl asarinin 2'-O-β-D- glucopyranosyl-(1→6)-D-glucopyranoside (3), 2'-hydroxyl asarinin 2'-O-β-D-apiofuranosyl-(1→2)-D-glucopyranoside (cuscutoside A, 4), kaempferol 3,7-di-O-β-D-glucopyranoside (5), 5-caffeoyl quinic acid (6), 4-caffeoyl quinic acid (7), and cinnamic acid (8). Their structures were elucidated on the basis of spectroscopic analyses including HR-ESI-MS, ESI-MS/MS, 1H and 13C NMR, HSQC, HMBC, and TOCSY.
- He, Xiang-Hui,Yang, Wen-Zhi,Meng, A-Hui,He, Wen-Ni,Guo, De-An,Ye, Min
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experimental part
p. 934 - 939
(2011/02/22)
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- Eight new oleanane-type triterpenoid saponins from Platycodon Root
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Eight new triterpenoid saponins, platyconic acids B (1), C (2), D (3), E (4), platycodins J (5), K (6), L (7) and platycosaponin A (8), were isolated from Platycodon Root, together with twelve known compounds, and they were characterized on the basis of their spectroscopic and chemical data. The Japan Institute of Heterocyclic Chemistry.
- Fukumura, Motonori,Iwasaki, Daigo,Hirai, Yasuaki,Hori, Yumiko,Toriizuka, Kazuo,Kenny, Peter T. M.,Kuchino, Yoshiyuki,Ida, Yoshiteru
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experimental part
p. 2793 - 2806
(2011/04/24)
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- Chemical constituents from Saussurea cordifolia
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Thirty-six naturally occurring compounds, including four C10-acetylenic glycosides and a lignan, were isolated from the whole plants of Saussurea cordifolia. Their structures were elucidated by means of spectroscopic and chemical methods to be 4,6-decadiyne-1-O-β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranoside (1), 4,6-decadiyne-1-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside (2), (8E)-decaene-4, 6-diyn-1-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside (3), (8Z)-decaene-4,6-diyn-1-O-β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranoside (4), and (2R, 3S, 4S)-4-(4-hydroxy-3-methoxybenzyl)-2-(5-hydroxy-3-methoxyphenyl)-3-(hydro xymethyl)-tetrahydrofuran-3-ol (5).
- Li, Xu-Wen,Guo, Zi-Tao,Zhao, Yun,Zhao, Zheng,Hu, Jin-Feng
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experimental part
p. 682 - 687
(2010/06/17)
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- New saponins from Sechium mexicanum
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The chemical study of Sechium mexicanum roots led to the isolation of the two new saponins {3-0-β-d-glucopyranosyl (1→3)-β-d- glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-0-α-l-rhamnopyranosyl-(1→3)-β-d- xylopyranosyl-(1→4)- α-l-rham
- Hernandez-Carlos, Beatriz,Carmona-Pineda, Miriam,Villanueva-Canongo, Claudia,Lopez-Olguin, Jesus F.,Aragon-Garcia, Agustin,Joseph-Nathan, Pedro
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experimental part
p. 994 - 1003
(2010/06/15)
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