Triterpenoid Saponins from Clematis tangutica

Clenlall\vlanglllica(Maxim).KorshisaTibetanherbandhasbeenusedtotreatindigestionandskindiseasesl.Nophytochemicalworkonthisplanthasbeenreportedinliterature.Inourwork.someglycosideswereobtainedtyomaerialpartofthisplant.Inthispaper.thestructureelucidationoftwonewtriterpenoidsaponins.tanguticosideAandBaredescribed.Onmineralacidhydrolysis.both1and2yieldedthesameaglycone.BycomparingMP.MS,'HNMRand13CNMRspectratheaglyconewasdeterminedtobehederagenin=.Glucoseandrhamnosewereobtainedfromhydrolysis…     

青海省唐古特铁线莲质量控制标准的研究

目的对青海省唐古特铁线莲质量控制标准进行研究。方法采用薄层色谱法对唐古特铁线莲进行定性鉴定,展开剂为氯仿与丙酮（95：5）,显色剂为10％硫酸甲醇;采用HPLC（Lc-2010HT）法测定唐古特铁线莲中齐墩果酸的含量,色谱柱为PhenomenexLunaCt8（250mm×4．6mm,5Ixm）,流动相为y（乙腈）＋V（0．2％磷酸水溶液）=35＋65,流量为1mL／min,柱温为室温（25℃）,检测波长为205nm。结果薄层色谱鉴定中,供试品色谱与对照品色谱相应的位置上,显示出相同颜色的荧光斑点;齐墩果酸在0．0233—0,7000mg／mL范围内呈良好的线性关系,线性回归方程为Y=2×10-6＋360803,r。=0．9917,RSD为1．61％,并对青海省野生和栽培唐古特铁线莲中齐墩果酸进行了定量分析,结果显示前者平均值为0．1184％、RSD为2．5113％,后者平均值为0．0651％、RSD为2．92％。结论该法操作简单、快速、准确、灵敏、重现性好,可有效控制青海省唐古特铁线莲的质量。     

Two Novel Epimeric Eremophilane Sesquiterpenes from the Flower of Cacalia tangutica

Two novel epimeric eremophilane sesquiterpenes, 7β-H-3α-angeloyl-9(10)-ene-11,12-epoxy-8-oxoeremophilane (1) and 7β-H-3α-angeloyl-9(10)-ene-11, 12-epoxy-8-oxoeremophilane (2) were isolated from the methanol extract of the flower of Cacalia tangutica (Franch.) Hand-Mazz. Their structures were characterized by 1D-, 2D-NMR (^1H-^1H COSY, HMQC, HMBC, ^1H-^1H NOESY) and HRESI-MS techniques.     

Two Novel Saponins from Lysimachia capillipes

We have isolated some flavones, lactone and two new saponins from Lysimachia capillipes1-3, now we continue to report the isolation and structural elucidation of two novel saponins, capilliposide C 1 and capilliposide D 2. Capilliposide C showed significant cytotoxic activity against human A2780 cells. The whole plant of Lysimachia capillipes was extracted with 95% and 50% EtOH, successively, and the extracts were combined and concentrated. The residue was chromatographed on silica gel res…     

Oleanane-triterpene Saponins from Clinopodium urticifolium

Four new oleanane triterpene saponins were isolated and purified from the whole plant of Clinopodium urticifolium. They were 3β, 16β, 23, 28-tetrahydroxyoleana-9 (11), 12(13)-diene-3-yl-[β-D-glucopyranosyl-(1→2)]-[β-D-glucopyranosyl-(1→3)]- β-D-fucopyranoside 1; 3β, 16β,21β, 23, 28-pentahydroxyoleana-9(11), 12(13)-diene-3-yl-[β-D-glucopyranosyl-(1→2)]-[ β-D-glucopyranosyl-(1→3)]- β-D-fucopyranoside 2; 3β, 16β, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[β-D-glucopyranosyl-(1→β)- β-D-glucopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside 3; 3β, 16β, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[β-D-gluco-pyranosyl-(1→4)-β-D-glucopyranosyl-(1→β)-β-D-glucopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→2)]- β-D-fucopyranoside 4. Their structures were elucidated on the basis of interpretation of NMR and MS data and from chemical evidence.     

A new indole-type alkaloid from the roots of Clematis florida var. plena

One new indole-type alkaloid, α-L-rhamnopyranosyl-(1→6)-β-D- glucopyranosyl 6-methoxy-3-indolecarbonate (1), together with three known alkaloids (2–4), one aromatic acid (5) and five known saponins (6–10), was isolated from the roots of Clematis florida var. plena. Their structures were established by NMR spectroscopic analysis and acid hydrolysis. In in vivo anti-inflammatory activity, n-butanol extract was found to be potent against ear edema in mice, with inhibition rate of 48.7% at a dose of 800?mg/kg. Furthermore, compounds 8 and 9 obtained from the n-butanol extract exhibited significant anti-inflammatory activities with inhibition rates of 50.9% and 54.7% at a dose of 200?mg/kg.     

A New Flavan from Sinacalia tangutica

A new flavan named 4α; 5-dimethoxy-8-formyl-7-hydroxy-6-methylflavan （1） was isolated from Sinacalia tangutica. Its structure was determined using spectroscopic methods and X-ray diffraction experiments.     

青海省唐古特铁线莲中齐墩果酸含量的测定

建立了唐古特铁线莲中齐墩果酸含量测定的HPLC方法。色谱条件:采用Phenomenex Luna C18(250 mm×4.6 mm,5μm),流动相:乙腈-0.2%H3PO4(35:65),流速:1 mL/min,柱温:室温(25℃),检测波长:205 nm。齐墩果酸在0.0233～0.7000 mg范围内呈良好的线性关系,线性回归方程为y=2E+06x+360803,R2=0.9917,回收率RSD为1.7%,并对青海省野生和栽培唐古特铁线莲中齐墩果酸进行了定量分析,结果显示前者平均值为0.1184%,后者平均值为0.0651%。方法可用以测定唐古特铁线莲中齐墩果酸的含量。     

Two New Saponins from Lysimachia davurica

Two new saponins named davuricoside I (1) and davuricoside E (2) were isolated from the whole plants ofLysimachia davurica. Their structures were determined by 1D and 2D NMR, FAB-MS techniques, and chemical methods.     

Two New Steroidal Saponins from Tacca plantaginea

Two new C27 steroidal glycosides, named taccaoside A(1) and B(2), were isolated from the traditional Chinese herb Tacca plantaginea. The spectroscopic and chemical evidences revealed their structures to be 26-O-β-D-glucopyranosyl-(25R)-3β,26-dihydroxy furost-5,20-diene-3-O-[α-L-rhamnopyranosyl(1→2)]-[α-L-rhamnopyranosyl(1→3)]-β-D-glucopyranoside(1) and 26-O-β-D-glucopyranosyl-(25R)-3β,26-dihydroxy furost-5,20-diene-3-O-[α-L-rhamnopyranosyl-(1→2)]-[β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl(1→3)]-β-D-glucopyranoside(2),respectively.     

Saponins from the roots of Chenopodium bonus-henricus L.

Two new glycosides of phytolaccagenin and 2β-hydroxyoleanoic acid, namely bonushenricoside A (3) and bonushenricoside B (5) together with four known saponins, respectively compounds 3-O-L-α-arabinopyranosyl-bayogenin-28-O-β-glucopyranosyl ester (1), 3-O-β-glucuronopyranosyl-2β-hydroxygypsogenin-28-O-β-glucopyranosyl ester (2), 3-O-β-glucuronopyranosyl-bayogenin-28-O-β-glucopyranosyl ester (4) and 3-O-β-glucuronopyranosyl-medicagenic acid-28-β-xylopyranosyl(1→4)-α-rhamnopyranosyl(1→2)-α-arabinopyranosyl ester (6) were isolated from the roots of Chenopodium bonus-henricus L. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, IR and HRMS). The MeOH extract and compounds were tested for cytotoxic activity on five leukemic cell lines (HL-60, SKW-3, Jurkat E6-1, BV-173 and K-562). In addition, the ability of metanolic extract and saponins to modulate the interleukin-2 production in PHA/PMA stimulated Jurkat E6-1 cells was investigated as well.     

Synthesis of Novel Antifungal Triazole Compounds

Based on our previous studies of 3D-QSAR, 38 novel objective compounds belonging to 4 series were designed and successfully synthesized directed by the idea of reconstructing the structure of non-pharmacophores while reserving essential ones in triazoles. In vitro pilot studies on their antifungal activities showed that most compounds have inhibitory effects on C.albicans and some inhibit S.cerevisiae also. The effects on C.albicans of 5 compounds are more potent than or equal to that of fluconazole or itraconazole.     

Two New Spirostanol Saponins from Reineckia carnea

Two new spirostanol saponins, (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐(β‐D ‐xylopyranoside) ( 1 ) and (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐fucopyranoside] ( 2 ), along with two known compounds, (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐xylopyranoside] ( 3 ) and (1β,3β,4β,5β,25S)‐spirostan‐1,3,4,5‐tetrol 5‐(β‐D ‐glucopyranoside) ( 4 ) were isolated from the whole plant of Reineckia carnea. The structures of the new steroids were determined by detailed analysis of their 1D‐ and 2D‐NMR spectra and chemical methods, and by comparison with spectral data of known compounds. Compounds 3 and 4 were isolated from the genus Reineckia for the first time.     

Two New Acylated Tridesmosidic Saponins from Astragalus armatus

Two new tridesmosidic glycosides of (3β,6α,16β,20R,24S)‐20,24‐epoxycycloartane‐3,6,16,25‐tetrol (=cycloastragenol), armatosides I and II ( 1 and 2 , resp.), were isolated from the roots of Astragalus armatus (Fabaceae) as well as the known bidesmosidic glycosides of cycloastragenol, trigonoside II ( 3 ) and trojanoside H ( 4 ). Their structures were elucidated as (3β,6α,16β,20R,24S)‐3‐O‐(2,3‐di‐O‐acetyl‐β‐D ‐xylopyranosyl)‐20,24‐epoxy‐25‐O‐β‐D ‐glucopyranosyl‐6‐O‐β‐D ‐xylopyranosylcycloartane‐3,6,16,25‐tetrol ( 1 ), and (3β,6α,16β,20R,24S)‐3‐O‐(2‐O‐acetyl‐β‐D ‐xylopyranosyl)‐20,24‐epoxy‐25‐O‐β‐D ‐glucopyranosyl‐6‐O‐β‐D ‐xylopyranosylcycloartane‐3,6,16,25‐tetrol ( 2 ). These structures were established by extensive NMR and MS analyses and by comparison with literature data.     

Microwave-Assisted Desulfation of the Hemolytic Saponins Extracted from Holothuria scabra Viscera

Saponins are plant and marine animal specific metabolites that are commonly considered as molecular vectors for chemical defenses against unicellular and pluricellular organisms. Their toxicity is attributed to their membranolytic properties. Modifying the molecular structures of saponins by quantitative and selective chemical reactions is increasingly considered to tune the biological properties of these molecules (i) to prepare congeners with specific activities for biomedical applications and (ii) to afford experimental data related to their structure–activity relationship. In the present study, we focused on the sulfated saponins contained in the viscera of Holothuria scabra, a sea cucumber present in the Indian Ocean and abundantly consumed on the Asian food market. Using mass spectrometry, we first qualitatively and quantitatively assessed the saponin content within the viscera of H. scabra. We detected 26 sulfated saponins presenting 5 different elemental compositions. Microwave activation under alkaline conditions in aqueous solutions was developed and optimized to quantitatively and specifically induce the desulfation of the natural saponins, by a specific loss of H₂SO₄. By comparing the hemolytic activities of the natural and desulfated extracts, we clearly identified the sulfate function as highly responsible for the saponin toxicity.     

Antifungal Activity of New Diterpenoid Alkaloids Isolated by Different Chromatographic Methods from Delphinium peregrinum L. var. eriocarpum Boiss

This paper aimed to investigate the potential antifungal influences of new alkaloids from Delphinium peregrinum L. var. eriocarpum Boiss. New Diterpenoid alkaloids Delcarpum (1), Hydrodavisine (4) and known alkaloids Peregrine (2), Delphitisine (3) were isolated by different chromatographic methods from the aerial parts of D. Peregrinum eriocarpum Boiss, which grows in Syria. The structures of alkaloids were proposed based on 1D NMR spectroscopy ¹H-NMR, ¹³C-NMR, DEPT-135, DEPT-90, 2D NMR spectroscopy DQF-COSY, HMQC, EI-Ms mass spectrum, and IR spectroscopic measurements. The antifungal activity of the isolated alkaloids was evaluated against different dermatophyte fungal isolates compared with fluconazole. In the case of Peregrine (2) the minimum inhibitory concentrations(MICs) recorded 128–256, 32–64, and 32 for Epidermophyton floccosum, Microsporum canis, and Trichophyton rubrum, respectively, compared to 32–64, 16, and 32 μg/mL in the case of fluconazole, respectively. The MICs recorded on application of the four alkaloids mixture were 64, 32, and 16 in the case of E. floccosum, M. canis, and T. rubrum, respectively, which were significantly lower than that measured for each of the individual alkaloid and were compatible for fluconazole. In conclusion, MICs of the tested alkaloids showed a variable potential effect on the investigated fungal isolates. Peregrine (2) was the most effective alkaloid, however, the application of the mixture of alkaloids induced significant synergistic activity that was more pronounced than the application of individual ones.     

Two New Triterpenes from Astilbe chinensis

Astilbe chinensis (Maxim.) Franch. et Sav. is a perennial herbaceous plant growing in China, Russia, Japan, and Korea. Its rhizome has been used for headache, arthralgia, chronic bronchitis and stomachalgia in traditional Chinese medicine1. Pharmacologica…     

两个非对映异构三萜皂甙的结构鉴定

从合欢皮95%乙醇提取物中分得2个新三糖链九糖皂甙(1,2),经化学方法和光谱分析,将其结构分别鉴定为:3-O-[β-D-吡喃木糖基-(1→2)-β-D-吡喃阿拉伯糖基-(1→6)-β-D-葡萄糖基]-21-O-(6S)-2-反式-2,6-二甲基-6-O-[4-O-((6R)-2-反式-2,6-二甲基-6-O-β-D-吡喃鸡纳糖基-2,7-辛二烯酸基)-β-D-吡喃鸡纳糖基]-2,7-辛二烯酸基金合欢酸28-O-β-D-吡喃葡萄糖基-(1→3)-[α-L-呋喃阿拉伯糖基-(1→4)]-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖基酯(1)和3-O-[β-D-吡喃阿拉伯糖基-(1→2)-β-D-吡喃呋糖基-(1→6)-β-D-葡萄糖基]-21-O-(6S)-2-反式-2,6-二甲基-6-O-[4-O-((6S)-2-反式-2,6-二甲基-6-O-β-D-吡喃鸡纳糖基-2,7-辛二烯酸基)-β-D-吡喃鸡纳糖基]-2,7-辛二烯酸基金合欢酸28-O-β-D-吡喃葡萄糖基-(1→3)-[α-L-呋喃阿拉伯糖基-(1→4)]-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖基酯(2),分别命名为合欢皂甙J₁₄(JulibrosideJ₁₄)和合欢皂甙J₁₅(JulibrosideJ₁₅)     

Two New Triterpenoid Saponins from Stauntonia obovatifoliola Hayata ssp. intermedia

Two new hederagenin‐type saponins, staunoside G ( 1 ) and staunoside H ( 2 ), along with twelve known triterpenoid saponins, were isolated from stems of Stauntonia obovatifoliola Hayata ssp. intermedia. Their structures were determined by analysis of HR‐EI‐MS, and 1D‐ and 2D‐NMR data, and comparison with those in literature. The two new compounds showed moderate cytotoxicities against three tumor cells, i.e., A549 (lung carcinoma), 4T1 (mammary carcinoma), and HeLa (cervical carcinoma).