Two new steroidal glycosides from Ophiopogon japonicus

Two new C27-steroidal glycosides were isolated from the fibrous roots of Ophiopogon japonicus. The spectral analysis and chemical evidence revealed their chemical structures to be （25R）-spirost-5,14-dien-3β-yl-O-α-L-rhamnopyranosyl-（1 → 2）-β-D- xylopyranosyl-（1 → 4）-β-D-glucopyranoside （1） and ophiogenin 3-O-β-D-glucopyranoside （2）.     

A new C27-steroidal glycoside from Ophiopogon japonicus

A new C27-steroidal glycoside with three known compounds were isolated from the tuber of Ophiopogonjaponicus （Thunb.） Ker-Gawl. Based on the spectral analysis, including HRMS, 1H NMR, 13C NMR, DEPT, 1H-1H COSY, HMQC and HMBC, their chemical structures were determined as pennogenin-3-O-α-L-rhamnopyranosyl-（1→ 2）-β-D-xylopyranosyl-（1→ 4）-13-D-gluco- pyranoside （1）, pennogenin-3-O-α-L-rhamnopyranosyl-（1→ 2）-β-D-glucopyranoside （2）, ophiopojaponin C （3） and ophiopogonin D （4）. 2007 Jian Zhong Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.     

Two new steroidal glucosides from Ophiopogon.japonicus （L.f.） Ker-Gawl

Two new steroidal glucosides, 26-O-β-D-glucopyranosyl （25S）-furost-5-ene-1β,3β,22α,26-tetraol l-O-β-D-xylopyranosyl- （1 → 3）-[α-h-rhamnopyranosyl-（1 → 2）]-[β-D-fueopyranoside and （25R） spirost-5-ene-3β,14α-diol-3-β-O-β-L-rhanmopyranosyl- （1 → 2）-[β-D-xylopyranosyl（1 → 4）]-[-β-D-glucopyranoside, were isolated from the Ophiopogon japonicus （L.f.） Ker-Gaw. Their structures were elucidated by spectroscopic methods.     

Three New Homoisoflavanones from the Ophiopogon japonicus Ker‐Gawler (Liliaceae)

Three new homoisoflavanones, 1 – 3 , together with a known one, 4 , were obtained from the AcOEt extract of the tuberous roots of Ophiopogon japonicus (Liliaceae). They were identified as (3R)‐2,3‐dihydro‐7‐hydroxy‐5‐methoxy‐3‐(4‐methoxybenzyl)‐6,8‐dimethyl‐4H‐chromen‐4‐one ( 1 ), (3R)‐3‐(1,3‐benzodioxol‐5‐ylmethyl)‐2,3‐dihydro‐7‐hydroxy‐5‐methoxy‐6,8‐dimethyl‐4H‐chromen‐4‐one ( 2 ), (3R)‐3‐(1,3‐benzodioxol‐5‐ylmethyl)‐2,3‐dihydro‐7‐hydroxy‐5‐methoxy‐6‐methyl‐4H‐chromen‐4‐one ( 3 ), and ophiopogonanone A ( 4 ). Their structures were determined on the basis of extensive NMR‐spectroscopic and mass‐spectrometric analyses. The three new compounds are rare homoisoflavanones which contain a MeO group at C(5). Compounds 1 and 2 showed weak cytotoxicity against the HepG2 (human hepatoma G2), KB (human oral epidermoid carcinoma), and MCF‐7 (human breast adenocarcinoma) cell lines in an MTT assay. Compound 3 exhibited weak cytotoxicity against HepG2 and MCF‐7, and moderate cytotoxicity against KB cell lines. Compound 4 showed moderate cytotoxicity against HepG2, KB, and MCF‐7 cell lines.     

A new steroidal glycoside and a new phenyl glycoside from a ripe cherry tomato

A new steroidal glycoside and a new phenyl glycoside have been isolated from a ripe cherry tomato [Lycopersicon esculentum var. cerasiforme (DUNAL) ALEF., Solanaceae] along with two known steroidal alkaloid glycosides, esculeoisides A and B, and five aromatic compounds, zizibeoside I, benzyl alcohol beta-gentiobioside, rutin, methyl caffeate, and phenylalanine. Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence.     

Homoisoflavonoids from Ophiopogon japonicus

Phytochemical study on the root tubers of Ophiopogon japonicus resulted in the isolation and identification of 13 homoisoflavonoids, including three new compounds, 8‐formyl‐7‐hydroxy‐5,4′‐dimethoxy‐6‐methylhomoisoflavone ( 1 ), 6‐formylisoophiopogonone B ( 2 ), and 8‐formylophiopogonanone B ( 4 ), and the ten known homoisoflavonoids 3 , and 5 – 13 . The absolute configurations of 8‐formylophiopogonanone B ( 4 ) and 8‐formyl‐7‐hydroxy‐5,4′‐dimethoxy‐6‐methylhomoisoflavanone ( 5 ) were confirmed by time‐dependent density‐functional‐theory (TD DFT) calculations of their theoretical electronic circular dichroism (ECD) spectra. The structure of the formerly reported ‘6‐aldehydoisoophiopogonone B’ was revised to 8‐formylophiopogonone B ( 3 ). All compounds were evaluated for their cytotoxic activities against the human‐lung‐tumor A549 cell line, and compounds 3, 9, 10 , and 13 exhibited promising antiproliferative activities with IC₅₀ values of 10.01, 6.40, 0.84, and 1.66 μM , respectively.     

日本续断中新的双糖链三萜皂苷的结构研究

从日本续断根部的乙醇提取物中分得一个新的三萜皂苷。经过测定,它为：3-O-α-L-吡喃鼠李糖(1→3)-β-D-吡喃葡萄糖(1→3)-α-L-吡喃鼠李糖(1→2)-α-L-吡喃阿拉伯糖9常春藤苷元－28-O-β-吡喃葡萄糖酯苷)。结果表明,采用一维SEMDY,旋转坐标NOE差谱和选择性远程DEPT核磁共振新技术相结合的方法测定糖链结构不需要对化合物进行化学降解或衍生化,方法简便、快速,测定结果可靠,每个糖基的信号可以分辨和明确归属。     

A new steroidal glycoside from Corypha taliera Roxb., a globally endangered species

The reversed-phased HPLC analysis of the methanol extract of the pericarp of C. taliera Roxb. (Talipalm), a rare species of Arecaceae family, afforded a new steroidal glycoside, β-sitosterol-3-O-α-l-rhamnopyranosyl-(1→4)-β-d-xylopyranosyl-(1→4)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside (1). The structure of the compound was elucidated unequivocally by UV, IR, HR-ESI-MS, ¹H and ¹³C NMR spectroscopic studies.     

Two New Steroidal Glycosides from Ophiopogon japonicus

The tuber of Ophiopogon japonicus Ker-Gawl. is recorded to have various functions, such as against cardiovascular diseases and anti-bacteria, and used as a potent drug to treat different diseases, especially heart diseases1. Since the first steriodal glycoside was isolated from the plant by Japanese scholars2, much attention has been paid to the studies of the chemical components of O. japonicus in recent decades. Steroidal glycosides as the major glycosides with the aglycones of ruscogenin …     

Two new triterpenoids and a steroidal glycoside from the aerial parts of Ocimum basilicum

Studies on the chemical constituents of the aerial parts of Ocimum basilicum have led to the isolation of three new compounds, basilol (1), ocimol (2), and basilimoside (3), along with two known constituents betulinic acid and oleanolic acid. The structures of the new constituents have been elucidated through spectral studies including 2D-NMR experiments (HMQC, HMBC, COSY, NOESY, and J-resolved) and chemical transformation, as p-formylphenyl 3beta-hydroxyolean-12-en-28-oate (1), 2-methoxy-4-carbomethoxyphenyl 3beta-hydroxy-lup-20(29)-en-28-oate (2), and (22E)-24xi-ethyl-25-methylcholesta-5,22-diene-3beta-ol-3-O-D-glucopyranoside (3).     

川麦冬皂苷类化学成分的研究

从川麦冬[Ophiopogon japonicus (Thunb.) Ker-Gawl.]中分离得到四个皂苷类成分, 分别鉴定为14-hydroxy sprengerinin C (1), sprengerinin C (2), ophiogenin-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (3)和β-胡萝卜苷(4, β-sitosterol β-D-glucopyranoside). 其中14-hydroxy sprengerinin C为新的C27甾体皂苷, 化合物sprengerinin C为首次从该植物分离得到. 运用现代波谱技术, 包括二维核磁共振谱和高分辨质谱, 对上述化合物的结构进行了确证.     

A new secoiridoid glycoside from the fruits of Cornus officinalis (Cornaceae)

A new secoiridoid glycoside, 7β-O-dimethyl butanedioate morroniside (1) was isolated from the fruits of Cornus officinalis (Cornaceae) along with the known compound, caffeoyltartaric acid dimethyl ester (2) which was isolated from the family Cornaceae for the first time. Their structures were elucidated by physical and spectroscopic data analysis, including 1D and 2D NMR, ESI-MS and CD experiments.     

New C21 steroidal glycoside from Cynanchum paniculatum

A new C21 steroidal glycoside, neocynapanogenin F 3-O-β-D-thevetoside 1, as well as its known aglycone neocynapanogenin F 2, which have an aberrant 13, 14:14, 15-disecopregnane-type skeleton were isolated from the root of Cynanchum paniculatum.Their structures were elucidated on the basis of spectroscopic data analysis. These compounds showed certain cytotoxic activities invitro.     

A new steroid glycoside from the starfishPatiria pectinifera

From the glycoside fraction of the starfishPatiria pectinifera, after its desulfation, an artefactural glycoside has been obtained: 29(-L-arabinofuranosyloxy)-5-stigmastane-3,6,8,15,16-pentaol (I). The structure of (I) was shown by¹H and¹³C NMR spectra and mass spectra and by acetylation and high-temperature hydrogenation.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Institute of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 356–361, May–June, 1985.     

Chemistry, bioactivity and geographical diversity of steroidal alkaloids from the Liliaceae family

Plants belonging to the Liliaceae family have been the topic of research in many phytochemical and pharmacological laboratories because they contain structurally complex and biologically fascinating steroidal alkaloids. This review, citing 153 references, summarises the chemistry, bioactivity and geographical diversity of steroidal alkaloids isolated from Veratrum and Fritillaria species, so as to illustrate the chemo-diversity and biological significance of these alkaloids, along with their geographical distribution where this is discernible.     

川麦冬中的新呋甾皂苷的分离与鉴定

从川麦冬块根总皂苷中分离并鉴定了4个双糖链甾体皂苷化合物, 其中化合物1为新化合物, 化合物2~4是已知化合物.     

A new steroidal alkaloid from Beaumontia grandiflora

A new steroidal alkaloid,beaumontamine(1),was isolated from the stems of Beaumontia grandiflora.The structure was elucidated on the basis of spectral analysis.     

A new steroidal saponin from Dioscorea cayenensis

The new 26-O-beta-D-glucopyranosyl-3beta,26-dihydroxy-20,22-seco-25(R)-furost-5-en-20,22-dione-3-O-alpha-L-rhamnopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (1), along with the known methyl protodioscin (2), asperoside (3) and prosapogenin A of dioscin (4) were isolated from the rhizomes of Dioscorea cayenensis LAM.-HOLL (Dioscoreaceae). Their structures were established mainly on the basis of 600 MHz 2D-NMR spectral data. 4 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (MICs of 20.8, 6.25, 25 microg/ml, respectively), whereas saponins 1-3 were inactive.