- SPECTROSCOPIC STUDIES ON A WITHANOLIDE FROM WITHANIA COAGULANS
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The structure of a new withanolide was elucidated as 3β,14α,20αF,27-tetrahydroxy-1-oxo-20R,22R-witha-5,24-dienolide using chemical and spectroscopic methods.The structure was corroborated by comparative studies with known closely related withanolides.Sitosterol-β-D-glucoside was identified through chemical and spectroscopic means.Key Word Index - Withania coagulans; Solanaceae; whitanolides; steroidal lactones; trichloroacetylcarbamate esters; sitosterol glucoside.
- Ramaiah, Parimi Atchuta,Lavie, David,Budhiraja, Ramji D.,Sudhir, Sharan,Garg, Kailash N.
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- Leonurosides A-D: Steroid N-acetylglucosaminides from the fruits of Leonurus japonicus
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Four new naturally occurring steroidal glycosides (leonurosides A-D, 1-4) were isolated from the dried fruits of Leonurus japonicus (motherwort fruit). Their structures were established by spectroscopic and chemical methods. The monosaccharide unit was identified to be a 2-acetamido-2-deoxy-β-d-glucose and the aglycone is either a common 3β-stigmasterol or 3β-ergosterol derivative. These compounds are the first representatives of steroid N-acetylglucosaminides from vascular plants.
- Ye, Miao,Ma, Guang-Lei,Su, Jing-Jing,Xiong, Juan,Hu, Jin-Feng
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- Biosynthesis of Sitosterol in Tissue Cultures of Rabdosia japonica Hara and Ergosterol in Yeast from Acetate
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The fate of the hydrogen atoms originating from acetate was investigated in the biosynthesis of sitosterol (5) in cultured cells of Rabdosia japonica Hara and ergosterol (6) in yeast and the 1,2-hydride shifts, 20-H from C-17 and 17-H from C-13, were verified.
- Seo, Shujiro,Sankawa, Ushio,Seto, Haruo,Uomori, Atsuko,Yoshimura, Yohko,et al.
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- New compounds from the Red Sea marine sponge Echinoclathria gibbosa
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Three new compounds; β-sitosterol-3-O-(3Z)-pentacosenoate (1), 5α-pregna-3β-acetoxy-12β,16β-diol-20-one (2), and echinoclathriamide ((R)-2′-hydroxy-N-((2S,3S,4R)-1,3,4-trihydroxy-19- methylicosan-2-yl)heptadecanamide) (3), together with two known compound
- Mohamed, Gamal A.,Abd-Elrazek, Ali E.E.,Hassanean, Hashim A.,Youssef, Diaa T.A.,Van Soest, Rob
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- Sitosterol 3-O-α-riburonofuranoside from Bauhinia candicans
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From the aerial parts of Bauhinia candicans a novel steroidal glycoside was isolated and identified as sitosterol 3-O-α-D-riburonofuranoside.
- M. Iribarren, Adolfo,B. Pomilio, Alicia
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- New n-nonadecanoyl-β-sitosterol and other constituents from the stem-bark of Anacardium occidentale
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A new steroidal ester bearing n-nonadecanoyl moiety (1) and a mixture of isomeric cerebrosides (2) along with two known compounds were isolated from the methanol extract of the stem-bark of Anacardium occidentale. The structure of the new steroidal ester was determined as 3-n-nonadecanoyl-β-sitosterol on the basis of modern spectroscopic techniques (IR, ESI-MS, HR-ESIMS, 1D and 2D NMR) and chemical degradation studies. The structures of the known compounds were identified as gallic acid and tanacetene by comparison of the spectroscopic data with those of reported data. The mixture of cerebrosides was confirmed based on the analysis of 1D and 2D NMR. These compounds were evaluated for cytotoxicity against human cancer cell lines A549, SCOV3 and rat normal cell line NRK49f.
- Shehu, Abdullahi,Ponnapalli, Mangala Gowri,Mahboob,Prabhakar,Olatunji, Gabriel Ademola
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p. 1357 - 1363
(2019/08/22)
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- Chemical constituents of the aerial parts of Algerian Galium brunneum: Isolation of new hydroperoxy sterol glucosyl derivatives
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The liposoluble extract of Galium brunneum aerial parts from North-eastern Algeria was chemically investigated. The EtOAc soluble portion contained a series of glycosyl cucurbitacins and sterols including three new glucosyl hydroperoxy sterols 1–3 among other phenolic components whereas the BuOH soluble fraction was dominated by glycosyl derivatives of flavonoids, iridoids and lignans, according to the chemistry reported in the literature for the genus Galium. The structure of new oxidized sterols 1–3 was determined by spectroscopic methods as well as by comparison with related known metabolites. Selected main compounds from both extracts, which revealed moderate antibacterial activities, were tested for their growth inhibitory properties against Gram-positive and Gram-negative bacteria. This is the first report of cucurbitacins in plants of genus Galium.
- Bertella, Anis,Bitam, Fatma,Carbone, Marianna,Ciavatta, Maria Letizia,Gavagnin, Margherita,Smadi, Abla
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- Nurotoxic sterol glycosides
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The invention relates to compositions for use in animal models of neurodegenerative disease and methods therefor. More particularly, the invention relates to the use of neurotoxic sterol glycosides or neurotoxic glycolipids, or combinations thereof, in animal models of neurodegenerative disease. Neurotoxicity-modulating chromenols can also be used in these animal models in combination with the neurotoxic sterol glycosides or neurotoxic glycolipids, or combinations thereof.
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Page/Page column 47; 48; 49
(2017/03/14)
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- Practical and facile route to a functional intermediate from stigmasterol for the synthesis of 1α-hydroxyvitamin D5 and related compounds
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As a functional and versatile intermediate for the synthesis of 1α-hydroxyvitamin D5 and related compounds, 1α,2α-epoxy-3β-hydroxystigmasta-5,7-diene was synthesized by a practical and facile 17-step route from stigmasterol in 17% overall yield.
- Takahashi, Michiyasu,Hosokawa, Seiya,Ono, Yuuya,Kubodera, Noboru
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p. 101 - 113
(2017/03/11)
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- Identification and characterization of β-sitosterol target proteins
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β-Sitosterol is the most abundant plant sterol in the human diet. It is also the major component of several traditional medicines, including saw palmetto and devil's claw. Although β-sitosterol is effective against enlarged prostate in human clinical trials and has anti-cancer and anti-inflammatory activities, the mechanisms of action are poorly understood. Here, we report the identification of two new binding proteins for β-sitosterol that may underlie its beneficial effects.
- Lomenick, Brett,Shi, Heping,Huang, Jing,Chen, Chuo
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p. 4976 - 4979
(2015/03/30)
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- New cytotoxic cycloartane triterpene from Cassia italica aerial parts
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Phytochemical study of the aerial parts of Cassiaitalica Mill. (family: Fabaceae) growing in Saudi Arabia afforded one new cycloartane triterpene, named (22E)-3-β-hydroxycycloart-22-en-24-one (2), together with eight known compounds: β-sitosterol (1), uvaol (3), daucosterol (4), methyl 3,4-dihydroxybenzoate (5), emodin (6), 4-hydroxypheny-O-β-D-glucopyranoside (7), aloin (8) and rutin (9). The structure of the isolated compounds was determined by physical, chemical and spectral data (UV, IR, MS, 1D ( 1H, 13C and DEPT) and 2D (1H-1H COSY, HSQC and HMBC) NMR), as well as by comparing with authentic samples. Compounds 3-5 and 7-9 were isolated for the first time from the plant. Compound 2 was evaluated for its cytotoxic activity against the L5178Y and PC12 cell lines. The total methanolic extract and compounds 5-9 exhibited free radical-scavenging activity using DPPH assay.
- Mohamed, Gamal A.
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p. 976 - 983
(2014/07/21)
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- Chemical constituents from Zizyphus oenoplia
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Four compounds, β-sitosterol, β-sitosteryl-β-D-glucoside, luteolin and quercetin have been isolated from the barks of Zizyphus oenoplia and their structures were established on the basis of spectral evidences. This is the first report of these compounds in Z. oenoplia.
- Singh,Singh
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p. 433 - 434
(2012/10/29)
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- New steroidal glycoside ester and aliphatic acid from the fruits of Lycium Chinense
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Two new compounds stigmast-5-en-3β-ol-3-O-β-D-(2′-n- triacontanoyl) glucopyranoside (1) and 19,21-dimethyl triacont-17,22,24,26,28- pentaene-1-oic acid (2), along with the three known compounds n-tetracosanyl octadec-9-enoate (3), β-sitosterol, and β-sito
- Jung, Woo-Suk,Chung, Ill-Min,Ali, Mohd,Ahmad, Ateeque
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experimental part
p. 301 - 307
(2012/08/28)
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- A concise synthesis of β-sitosterol and other phytosterols
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A convenient synthesis of sidechain-modified phytosterols is achieved via a temporary masking of the stigmasterol 5,6-alkene as an epoxide. Following performance of the desired modification, the alkene is regenerated through a mild deoxygenation. The approach is applied to the syntheses of β-sitosterol and campesterol acetate, and suggests a facile route to the (Z)-isomers of Δ22-23 phytosterols.
- Hang, Jiliang,Dussault, Patrick
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experimental part
p. 879 - 883
(2010/10/19)
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- A tetranuclear-zinc-cluster-catalyzed practical and versatile deprotection of acetates and benzoates
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A new catalytic deacylation of acetates and benzoates through transesterification with methanol was developed (see scheme). Reactions with various acidand nucleophile-sensitive functional groups proceeded efficiently in the presence of a catalytic amount of the tetranuclear zinc cluster. The present catalysis is applicable to less-reactive tertiary acetates, the deacylation of which is difficult to achieve by transesterification with other catalysts.
- Iwasaki, Takanori,Agura, Kazushi,Maegawa, Yusuke,Hayashi, Yukiko,Ohshima, Takashi,Mashima, Kazushi
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supporting information; experimental part
p. 11567 - 11571
(2010/11/24)
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- New steroidal glycosides from the stem bark of Mimusops elengi
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Two new steroidal glycosides (1 and 2) have been isolated from the ethanolic extract of the stem bark of Mimusops elengi L. and characterized as stigmasta-5,22-dien-3β-ol-3β-D-glucuropyranosyl-(6'β→1'') -Dglucopyranoside (1) and β-sitosterol-3β-(3''',6'''
- Akhtar,Ali,Alam
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experimental part
p. 549 - 553
(2010/12/25)
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- Phytochemical investigation of the fruit peels of Citrus reticulata Blanco
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Phytochemical investigation of the fruit peels of Citrus reticulata Blanco (Rutaceae) resulted in the isolation of three new phytoconstituents along with n-hexacosonoic acid. Their structures have been established as 18H-urs-5,11-dien-3-ol-11-one-3-D-gluc
- Khan, M. Aasim,Ali,Alam, Prawez
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experimental part
p. 610 - 620
(2010/08/20)
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- PROCESS FOR RECOVERING STEROLS FROM A CRUDE SOURCE CONTAINING STEROL ESTERS
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A process of obtaining sterols suitable for human consumption from a crude wood pulping source containing sterol esters is disclosed. The sterols are obtained at high yield and purity. In particular, a process of obtaining sterols at high yield and purity from tall oil pitch (TOP) is disclosed. The sterols obtained can be esterified to sterol esters for use in dietary supplements and as additives for food and beverage products.
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(2008/12/06)
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- Synthesis of highly pure oxyphytosterols and (oxy)phytosterol esters. Part I. Regioselective hydrogenation of stigmasterol: An easy access to oxyphytosterols
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The synthesis of several oxyphytosterols is described starting from stigmasterol, the key step being the regioselective hydrogenation of the 22-23 double bond of the latter.
- Geoffroy, Philippe,Julien-David, Diane,Marchioni, Eric,Raul, Francis,Aoude-Werner, Dalal,Miesch, Michel
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p. 702 - 707
(2008/09/21)
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- Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide
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Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates, whereas several functional groups of the steroids and diterpenes were retained and neither isomerization nor degradation of these substrates was observed. It seems that the acetyl groups with lower steric hindrance or near carbonyl, alkoxy, or hydroxyl groups can be cleaved by the reaction, whereas the acetyl groups with higher steric hindrance or without carbonyl, alkoxy, or hydroxyl groups neighboring were retained under the same conditions. One of the interesting results obtained was the selective hydrolysis of the 3β-O-acetyl group in the presence of the 6β group in 3β,6β-Di-O-acetyl-5α-hydroxypregn-16-en-20-one. This allows for subsequent introduction of one unit at C-3 and the other unit at C-6. This procedure is useful for the synthesis of a series of closely related isomers of 3β,5α,6β-trihydroxypregn-16-en-20-one and other widespread polyhydroxysteroids in marine organisms and some terrestrial species.
- Wang, Shao-Min,Zhang, Yan-Bing,Liu, Hong-Min,Yu, Guo-Bin,Wang, Ke-Rang
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- A mild and efficient desilylation of O-tert-butyldimethylsilyl ethers mediated by chlorotrimethylsilane and potassium fluoride dihydrate in acetonitrile
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Desilylation of O-tert-butyldimethylsilyl ethers was achieved by a reagent system consisting of chlorotrimethylsilane and potassium fluoride dihydrate in acetonitrile. This alternative desilylation procedure is chemoselective, generally effective and operationally simple, and should find practical applications in organic synthesis. Georg Thieme Verlag Stuttgart.
- Peng, Yu,Li, Wei-Dong Z.
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p. 1165 - 1168
(2007/10/03)
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- Process for recovery of plant sterols from by-product of vegetable oil refining
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The process for recovery of plant sterols and tocopherols from deodorization distillates formed during chemical or physical refining of vegetable oils consists of the following steps: free fatty acids are removed from the deodorization distillate by vacuum distillation or by continuation solvent saponification, after the removal of free fatty acids, the received material is reacted with an aromatic carboxylic acid anhydride at a temperature of 50-150° C., under reduced pressure, after the treatment with anhydride, tocopherols are removed from the mixture, and crystalline free sterols are recovered from the distillation residue containing sterol esters, di- and triglycerides by transesterification.
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(2008/06/13)
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- Synthesis, isolation and characterisation of β-sitosterol and β-sitosterol oxide derivatives
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β-Sitosterol is the most prevalent plant cholesterol derivative (phytosterol) and can undergo similar oxidation to cholesterol, leading to β-sitosterol oxides. The biological impact of phytosterol oxides has only been evaluated in a phytosterol blend (usually of β-sitosterol, campesterol, stigmasterol and dihydrobrassicasterol). The lack of pure phytosterols, including β-sitosterol, hinders the collection of significant toxicity data on the individual β-sitosterol oxides. An efficient synthetic route to multi-gram quantities of pure β-sitosterol is described here, together with the first syntheses and characterisation of pure β-sitosterol oxides. The Royal Society of Chemistry 2005.
- McCarthy, Florence O.,Chopra, Jay,Ford, Alan,Hogan, Sean A.,Kerry, Joe P.,O'Brien, Nora M.,Ryan, Eileen,Maguire, Anita R.
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p. 3059 - 3065
(2007/10/03)
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- Mechanism of the second methylation in sitosterol side-chain biosynthesis in higher plants: Metabolic fate of 28-hydrogens of 24- methylenecholesterol in Morus alba cell cultures
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Biosynthesis of the side-chain of sitosterol in higher plants involves two methylation steps by attack of S-adenosylmethionine. The stereochemical features of the second methylation, namely, of the conversion from 24- methylenecholesterol to isofucosterol in higher plants has been investigated. Feeding studies of synthesized [28E-2H]- and [28Z-2H]-24- methylenecholesterols to cultured cells of Morus alba followed by 2H NMR analysis of the resulting isofucosterol established that the second methylation proceeded in such a manner that addition of the methyl group and proton loss occur on opposite faces of the original Δ(24(28))-double bond. (C) 2000 Elsevier Science Ltd.
- Okuzumi, Tatsuya,Kaji, Yuko,Hamada, Hiroki,Fujimoto, Yoshinori
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p. 3623 - 3626
(2007/10/03)
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- Cucurbitacins of Cucumis prophetarum and Cucumis prophetarum
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Cucurbitacin B, isocucurbitacin B, dihydrocucurbitacin B, cucurbitacin E, dihydrocucurbitacin E, isocucurbitacin D, dihydroisocucurbitacin D, cucurbitacin I, dihydrocucurbitacin I, cucurbitacin Q1, and dihydrocucurbitacin Q1 were identified for the first time as constituents of Cucumis prophetarum L., Cucurbitacin B, Cucurbitacin O, cucurbitacin P, cucurbitacin Q1, dihydrocucurbitacin Q1, isocucurbitacin E, and dihydroisocucurbitacin E also were identified as constituents of C. prophetatum Jusl. ssp. Dissectus. Isocucurbitacin E and dihydroisocucurbitacin E were isolated for the first time in nature. The chemical structures were determined with extensive spectroscopic analysis including 2D NMR, 1H NMR, 13C NMR, correlated spectroscopy (COSY), heteronuclear chemical shift correlation (HETCOR), attached proton test (AFT), and distortionless enhancement by polarization transfer (DEPT).
- Afifi,Ross,Elsohly,Naeem,Halaweish
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p. 847 - 859
(2007/10/03)
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- Montmorillonite clays catalysis IX: A mild and efficient method for removal of tetrahydropyranyl ethers
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A variety of tetrahydropyranyl ethers of alcohols and phenols are easily removed in the presence of catalytic of amount of montmorillonite clays in methanol at 40-50 °C in excellent yield.
- Li, Tong-Shuang,Zhang, Zhan-Hui,Jin, Tong-Shou
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p. 181 - 188
(2007/10/03)
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- Montmorillonite clay catalysis XI1: Protection and deprotection of hydroxyl group by formation and cleavage of trimethylsilyl ethers catalysed by catalysed by montmorillonite K-10
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An easy preparation of trimethylsilyl ethers of alcohols and phenols with 1,1,1,3,3,3-hexamethyldisilazane(HMDS) catalysed by montmorillonite K- 10 at room temperature has been carried out in excellent yields. Desilyation of trimeylsilyl ethers is catalysed by K-10 in methanol at ambient temperature in high yields.
- Zhang, Zhan-Hui,Li, Tong-Shuang,Yang, Feng,Fu, Cheng-Guang
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p. 3105 - 3114
(2007/10/03)
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- Inhibitory effect of cycloartenol ferulate, a component of rice bran, on tumor promotion in two-stage carcinogenesis in mouse skin
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Inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)- induced inflammation in mice was observed in the methanol extract of rice bran and γ-oryzanol. The active components of rice bran, sitosterol ferulate, 24-methylcholesterol ferulate, cycloartenol ferulate and 24- methylenecycloartanol ferulate inhibited markedly the TPA-induced inflammation in mice. The 50% inhibitory dose of these compounds for TPA- induced inflammation was 0.2-0.3 mg/ear. Furthermore, cycloartenol ferulate markedly inhibited the tumor-promoting effect of TPA in 7,12- dimethylbenz[α]lanthracene-initiated mice.
- Yasukawa, Ken,Akihisa, Toshihiro,Kimura, Yumiko,Tamura, Toshitake,Takido, Michio
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p. 1072 - 1076
(2007/10/03)
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- Synthesis of Triaromatic Steroid Hydrocarbons Methylated at Position 2, 3 or 6: Molecular Fossils of Yet Unknown Biological Origin.
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C21-29 triaromatic steroid hydrocarbons bearing a methyl group at unusual positions 2, 3 or 6 have been synthesized from pregnenolone, cholesterol or stigmasterol via stera-3,5-dienes.Their occurence in various sedimentary rocks and petroleums suggests the presence of yet unknown biological precursors.
- Lichtfouse, Eric,Albrecht, Pierre
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p. 1731 - 1744
(2007/10/02)
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- Chemical Studies on the Constituents of Hyphear Tanakae HOSOKAWA from Different Host Trees
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The chemical constituents of Hyphear Tanakae HOSOKAWA epiphyting to four different host trees were examined.A new triterpene fatty acid ester (III) and four known flavonoid glycosides, rhamnocitrin-3-O-rhamnoside (V), kaempferol-3-O-rhamnoside (VI), rhamnetin-3-O-rhamnoside (VII), and quercetin-3-O-rhamnoside (VIII) have been isolated from the leaves and twigs of this plant epiphyting to Castanea crenata SIEB., together with fatty acids (I), phytosterol (II), and phytosterol-glucoside (IV).The present investigation has revealed that compounds II-V, VII, and VIII are contained in this plant irrespective of the host, among the four host trees, examined.Keywords - Hyphear Tanakae; misletoe; Loranthaceae; triterpene; lup-20(29)-ene-3β,7β,15α-triol; flavonoid; rhamnocitrin-3-O-rhamnoside; kaempferol-3-O-rhamnoside; rhamnetin-3-O-rhamnoside; quercetin-3-O-rhamnoside
- Fukunaga, Takehiko,Nishiya, Koichi,Kajikawa, Ikuko,Watanabe, Yoshikuni,Suzuki, Nobuo,et al.
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p. 1180 - 1184
(2007/10/02)
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- Stereochemistry in the Hydrogenation of Steroidal (22R)- and (22S)-Δ24-26,22-Lactones
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Catalytic hydrogenation of the (22R)-unsaturated lactone 8 and its (22S)-epimer 9 afforded stereoselectively the (22R,24R)-saturated lactone 10 and the (22S,24S)-isomer 11, respectively.The C-24 stereochemistry of the hydrogenated products was determined by their conversion into 24-ethylcholesterols.Keywords - stereoselective hydrogenation; stereoidal lactone; sitosterol; clionasterol
- Iwadate, Hiroshi,Gamoh, Keiji,Fujimoto, Yoshinori,Ikekawa, Nobuo
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p. 2061 - 2065
(2007/10/02)
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- Side Chain Structural Requirement for Utilization of Sterols by the Silkworm for Growth and Development. Non-stereoselective Utilization of the 24-Stereoisomeric Pairs of 24-Alkylsterols
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Four C-24 epimeric pairs of 24-alkylsterols 1-8 were stereoselectively synthesized via orthoester Claisen rearrangement of the (22)R or (22S)-Δ23Z steroid derivatives (11 and 12).These compounds were tested on the silkworm larvae, Bombyx mori, in order to examine the relationship of the C-24 stereochemical arrangement and utilizability as a nutrient sterol.All of the tested sterols effectively supported the growth and development of the insect and were converted into cholesterol regardless of the C-24 configuration.Keywords - 24-alkylcholesterol; 24-alkyl-22-dehydrocholesterol; orthoester Claisen rearrangement; stereoselective synthesis; insect sterol; silkworm
- Fujimoto, Yoshinori,Kimura, Miki,Khalifa, Fathy A. M.,Ikekawa, Nobuo
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p. 4372 - 4381
(2007/10/02)
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- Sitoindosides I and II, Two New Anti-ulcerogenic Sterylacylglucosides from Musa paradisiaca
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Two new sterylacyl glucosides, sitoindosides I and II, isolated from the fruits of musa paradisiaca (banana, vegetable variety), have been assigned sitosterol 3-(6-O-palmitoyl-β-D-glucopyranoside) (1) and sitosterol 3-(6-O-oleoyl-β-D-glycopyranoside) (2) structures on the basis of spectroscopic analysis and chemical transformation.A 5:1 mixture of (1) and (2) (in doses of 50 mg/kg, oral administration) provided complete protection against aspirin-induced ulcer in albino rats and was free from any toxicity.
- Ghosal, Shibnath,Saini, Kulwant S.
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p. 965 - 975
(2007/10/02)
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- Comparative Studies on the Constituents of Ophiopogonis Tuber and Its Congeners. III. Studies on the Constituents of the Subterranean Part of Ophiopogon ohwii Okuyama and O. jaburan (Kunth) Lodd.
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Six steroidal glycosides tentatively named glycosides O-1, O-2 (1), O-3 (2), O-4 (3), O-5 (4) and O-6 (5), were isolated from the subterranean part of Ophiopogon ohwii Okuyama (Liliaceae) and another six steroidal glycosides, tentatively named glycosides J-1, J-2 (6), J-3 (7), J-4 (8), J-5 (9) and J-6 (10), were isolated from the subterranean part of O. jaburan (Kunth) Lodd.Glycosides O-1 and J-1 were identified as so-called β-sitosterol β-D-glucopyranoside.The structures of 1-10 were established as ophiopogonin B (1), Ophiopogonin D (2), ruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside (3), ruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-α-L-arabinopyranoside (=glycoside E of O. planiscapus Nakai) (4), 26-O-β-D-glucopyranosyl 22-hydroxy-25(R)-furost-5-en-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside (5), ophiopogonin D (=glycoside O-3 (2)) (6), a mixture of 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranosido-3-O-β-D-glucopyranosides of ruscogenin and neoruscogenin (7), neoruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-α-L-arabinopyranosido-3-O-β-D-glucopyranoside (8), a mixture of 26-O-β-D-glucopyranosyl 22-hydroxy-25(R)-furost-5-en-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranosido-3-O-β-D-glucopyranoside and 26-O-β-D-glucopyranosyl 22-hydroxyfurost-5,25(27)-dien-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranosido-3-O-β-D-glucopyranoside (9), and 26-O-β-D-glucopyranosyl 22-hydroxyfurost-5,25(27)-dien-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-α-L-arabinopyranosido-3-O-β-d-glucopyranoside (10).It is interesting that the main saponins, ophiopogonins B and D, found in Ophiopogonis Tuber (obtained from O. japonicus Ker-Gawler) were also found in O. ohwii (Okuyama and the latter saponin was also found in O. jaburan (Kunth) Lodd.Further, several steroidal glycosides carrying sulfate on the sugar moiety were found in Liliaceous plants belonging to the genus Ophiopogon. Keywords - Ophiopogonis Tuber; Ophiopogon ohwii; Ophiopogon jaburan; Liliaceae; spirostanol glycoside; furostanol glycoside; sulfated steroidal glycoside
- Watanabe, Yoshiaki,Sanada, Shuichi,Ida, Yoshiteru,Shoji, Junzo
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p. 3994 - 4002
(2007/10/02)
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- New Cytotoxic Principles from Datisca glomerata
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Datisca glomerata has been systematically fractionated by following cellular toxicity in an effort to identify previously uncharacterized cytotoxic principles.Several new cucurbitacin glycosides, including datiscosides B(8), C(3), D(9), E(4), F(5), G(6), and H(10) and the known compound datiscoside (1), as well as cucurbitacins B(11), D(2), and F(7) have been isolated and characterized.Structures were assigned to the compounds on the basis of their high field 1H n.m.r., 13C n.m.r., high-resolution mass spectra (CI, EI, and FD) and chemical interconversions.The structure of datiscoside C(3) was independently established by single-crystal X-ray analysis at 193 and 293 K.
- Sasamori, Hiroshi,Reddy, K. Sambi,Kirkup, Michael P.,Shabanowitz, Jeffrey,Lynn, David G.,at al.
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p. 1333 - 1347
(2007/10/02)
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- BIARYLHEPTANOIDS AND OTHER CONSTITUENTS FROM WOOD OF ALNUS JAPONICA
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The wood of Alnus japonica has been shown to contain a number of biarylheptanoids as well as other phenolics, including secoisolariciresinol diferulate.The co-occurence of cyclized biarylheptanoids with their corresponding acyclic biarylheptanoids has been demonstrated and this fact may have biosynthetic significance.The possible chemotaxonomic importance of biarylheptanoids in members of the Betulaceae is discussed.The isolation and identification of several steroids and triterpenoids are also described.Key Word Index- Alnus japonica; Betulaceae; new biarylheptanoids; biosynthesis; chemotaxonomy; secoisolariciresinol diferulate; steroids; oleanan triterpenoids.
- Nomura, Masayasu,Tokoroyama, Takashi,Kubota, Takashi
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p. 1097 - 1104
(2007/10/02)
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- Triterpene constituents of Tabernaemontana laurifolia and Haplophyton cimicidum
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The triterpene bauerenyl acetate was isolated directly by crystallization from the non-polar neutral extract of the bark of Tabernaemontana laurifolia D.C. A similar extract of Haplophyton cimicidum (whole plant) yielded, after chromatography, the triterpenes erythrodiol monostearate, bauerenol and betulin, as well as the steroid β-sitosterol.
- Cava,Shubber,Rao, Kota V.
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p. 1301 - 1303
(2007/10/12)
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