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1.
Four new triterpenoid saponins, designated as stelmatotriterpenosides E-H (1-4), together with three known compounds, asterbatanoside B (5), 2alpha,3beta,19alpha,23-tetrahydroxy-olean-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl ester (6) and 2alpha,3beta,19alpha,23-tetrahydroxy-urs-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl ester (7), were isolated from the stems of Stelmatocrypton khasianum. On the basis of chemical and spectral evidence, the structures of 1-4 were established as 2alpha,3beta,23-trihydroxy-olean-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (1), 2alpha,3beta,23-trihydroxy-urs-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (2), 2alpha,3beta,19alpha-trihydroxy-urs-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl ester (3), and 2beta,3beta,19alpha-trihydroxy-urs-12-en-24,28-dioic acid-24-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl diester (4). 相似文献
2.
The stems of Akebia quinata have been analyzed for their triterpene glycoside constituents, resulting in the isolation of six new triterpene glycosides, along with 19 known ones. On the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence, the structures of the new compounds were deter-mined to be 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid, and 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-23,29-dihydroxyolean-12-en-28-oic acid, respectively. The main triterpene glycosides contained in the stems of A. quinata were found to have two sugar units at C-3 and C-28 of the aglycone in this study, whereas those of Akebia trifoliate were reported to possess one sugar unit at C-28 of the aglycone. It may be possible to distinguish between A. quinata and A. trifoliate chemically by comparing their triterpene glycoside constituents. 相似文献
3.
Yuan JQ Yang XZ Miao JH Tang CP Ke CQ Zhang JB Ma XJ Ye Y 《Molecules (Basel, Switzerland)》2008,13(9):2229-2237
Two new ursane-type triterpene glucosides, 2alpha,3alpha,24-trihydroxyurs-12,18-dien-28-oic acid beta-D-glucopyranosyl ester (1) and 2alpha,3alpha,23-trihydroxyurs-12,19(29)-dien-28-oic acid beta-D-glucopyranosyl ester (2), were isolated from the roots of Rosa laevigata, together with three known compounds: 2alpha,3beta,19alpha-trihydroxyurs-12-en-28-oic acid beta-Dglucopyranosyl ester (3), 2alpha,3alpha,19alpha-trihydroxyurs-12-en-28-oic acid beta-D-glucopyranosyl ester (4) and 2alpha,3beta,19alpha,23-tetrahydroxyurs-12-en-28-oic acid beta-D-glucopyranosyl ester (5). The structures of new compounds were established on the basis of detailed 1D and 2D NMR spectroscopic analyses. Compounds 2 and 5 exhibited modest in vitro antifungal activities against Candida albicans and C. krusei. 相似文献
4.
Four triterpenoid saponins were isolated from Amaranthus hypochondriacus which are grain crops in the Nepal, Mexico and South America. Their structures were elucidated based on spectral evidence to be: (1) 3-O-alpha-L-rhamnopyranosyl(1----3)-beta-D-glucuronopyranosyl-2 beta,3 beta-dihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopyranosyl ester. (2) 3-O-alpha-L-rhamnopyranosyl(1----3)-beta-D-glucuronopyranosyl-2 beta,3 beta- dihydroxyolean-12-en-23-al-28-oic acid 28-O-beta-D-glucopyranosyl ester; (3) 3-O-alpha-L-rhamnopyranosyl(1----3)-beta-D-glucuronopyranosyl-2 beta, 3 beta-dihydroxy-30-norolean-12,20(29)-dien-28-oic acid 28-O-beta-D-glucopyranosyl ester. (4) 3-O-alpha-L-rhamnopyranosyl (1----3)-beta-D-glucuronopyranosyl-2 beta, 3 beta-dihydroxy-30-norolean-12, 20(29)-dien-23-al-28-oic acid 28-O-beta-D-glucopyranosyl ester. 相似文献
5.
The structures of 6 new oleanene glycosides (1--6) isolated from the leaves of Acanthopanax japonicus FRANCH et. SAVART (Araliaceae) were elucidated by mass, 1D, and 2D NMR spectroscopy. The structures of 1--6 were established as 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester of 3beta,23-dihydroxy-olean-12-en-28,29-dioic acid, 3beta,30-dihydroxy-olean-12-en-23,28-dioic acid, 3beta,29-dihydroxy-olean-12-en-23,28-dioic acid (=dianic aicd), 3beta-dihydroxy-olean-12-en-23,28-dioic acid (=gypsogenic acid), 3beta,29-dihydroxy-23-oxo-olean-12-en-28-oic acid, and 3beta-hydroxy-23-oxo-olean-12-en-28,29-dioic acid, designated acanjaposide D (1), E (2), F (3), G (4), H (5), and I (6), respectively. 相似文献
6.
Our ongoing investigations on the stem bark of Uncaria macrophylla afforded a new ursolic triterpene, 3β,6β,19α-trihydroxy-urs-12-en-28-oic acid-24-carboxylic acid methyl ester (1), named uncariursanic acid, and three known ursolic triterpenes including 3β,6β,19α-trihydroxy-23-oxo-urs-12-en-28-oic acid (2), 3β,6β,19α-trihydroxy-urs-12-en-28-oic acid (3) and ursolic acid (4). Their structures were elucidated by extensive spectral methods, including 1D and 2D NMR and HR-ESI-MS. The cytotoxicities of the four compounds were evaluated against two cancer cell lines (MCF-7 and HepG2) by the MTT method, and only compound 4 exhibited potent activity. 相似文献
7.
五叶木通中一个新的三萜成分 总被引:1,自引:0,他引:1
对五叶木通藤茎进行了较为系统的研究, 从其体积分数为80%的乙醇提取物的正丁醇部分分离得到3个三萜成分, 通过理化性质和波谱分析鉴定为: 3α,24-二羟基-30-去甲齐墩果烷-12,20(29)-双烯-28-酸(Ⅰ); 3α,24,29-三羟基齐墩果烷-12-烯-28-酸(Ⅱ); 2α,3β,23-三羟基齐墩果烷-12-烯-28-酸(Ⅲ). 其中化合物Ⅱ为新化合物, 命名为木通茎酸(Quinatic stem acid). 相似文献
8.
Fu WW Shimizu N Dou DQ Takeda T Fu R Pei YH Chen YJ 《Chemical & pharmaceutical bulletin》2006,54(4):557-560
Five new triterpenoid saponins, platycoside H [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside I [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside J [3-O-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside K [3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23,24-pentahydroxyolean-12-en-28-oic acid], and platycoside L [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23,24-pentahydroxyolean-12-en-28 oic acid], and three known triterpenoid saponins, platycoside F, platycoside B, and platycoside C, were isolated from the roots of Platycodon grandiflorum A. DC. Their chemical structures were elucidated on the basis of their spectral data and chemical evidence. 相似文献
9.
A new triterpenoid, 3-oxo-22alpha-hydroxy-olean-12-en-28-oic acid (1), oleanolic acid (2) and a known iridoid, 10-hydroxy-1-oxo-7-iriden-11-oic acid methyl ester (3) have been isolated from the dichloromethane extract of the dried seeds of Gardenia volkensii. Their structures were established by 1D and 2D NMR spectroscopic and MS methods. 相似文献
10.
Two new lupene-type triterpenoids, 3β,6β-dihydroxylup-20(29)-en-28-oic acid β-glucopyranosyl ester (1) and 2α-acetoxyl-3β,6β-dihydroxylup-20(29)-en-28-oic acid β-glucopyranosyl ester (2), along with 18 known compounds, were isolated from Liquidambar formosana. The structures were elucidated on the basis of spectroscopic methods, including UV, IR, ESIMS, 1D- and 2D-NMR experiments, as well as by comparison of the spectral data with those of related compounds. 相似文献
11.
Two new compounds: 3-β,15-α,23,28-tetrahydroxyolean-12-en-3-O-arabinopyaranoside and 3-β,23,28-trihydroxy-olean-12-en-3-O-β-D-glucopyranoside were isolated from the aerial parts of Ammania auriculata along with the known compounds kaempferol, β-sitosterol-3-O-β- D-glucoside, 2-α,3-β,23-trihydroxyolean-12-en-28-oic acid-28-O-β-D-glucopyranoside, quercetin, kaempferol-3-O-α-L-arabinofuranoside, kaempferol-3-O-β-D-xylopyranoside and ellagic acid. Structures of these compounds were elucidated on the basis of their spectroscopic data (NMR, UV, MS and IR spectra). The antioxidant activities of the total extract, the fractions CH(2)Cl(2), EtOAc and the remaining aqueous together with the compounds 1, 6 and 9 were comparable with that of the standard antioxidant, ascorbic acid. 相似文献
12.
Choudhary MI Batool I Khan SN Sultana N Shah SA Ur-Rahman A 《Natural product research》2008,22(6):489-494
The biotransformation of a pentacyclic triterpene, oleanolic acid (1), with Fusarium lini afforded two oxidative metabolites, 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (2), and 2alpha,3beta,11beta-trihydroxyolean-12-en-28-oic acid (3). Metabolite 3 was found to be a new compound. The structures were characterized on the basis of spectroscopic studies. These metabolites exhibited a potent inhibition of alpha-glucosidase enzyme. 相似文献
13.
Orlando Muoz Roberto Ruiz Antonio Gonzles Mercedes P. Nüez Ignacio Jimnez Angel Ravelo 《Helvetica chimica acta》1993,76(7):2537-2543
The known triterpenoids β-amyrin (= olean-12-en-3β-ol; 22 ), lupeol (= lup-20(29)-en-3β-ol; 17 ), betulin (= lup-20(29)-ene-3β,28-diol; 18 ), lup-20(29)-ene-3β,30-diol ( 20 ), oleanolic acid (= 3β-hydroxyolean-12-en-28-oic acid; 21 ), and betulonic acid (= 3-oxolup-20(29)-en-28-oic acid; 19 ), together with epicatechol (= cis-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; 23 ), 5′-O-methylgallocatechol (= trans-2-(3,4-dihydroxy-5-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; 24 ), and 4-hydroxybenzaldehyde were isolated from the aerial parts of Maytenus boaria (MOL. ). Additonally, the eight 4,C4-dihydro-β-agarofuran sesquiterpenoids 1–8 , one of them a diol with a (4R)-configuration, and compound 9 were present in the extract. The structures of these compounds were established by spectroscopic and chemical means. 相似文献
14.
A new triterpenoid, 2alpha,3alpha,24-trihydroxyurs-12-en-28-oic acid-28-O-beta-D-glucopyranosyl ester (4) along with four known triterpenoids, ursolic acid (1), 2alpha-hydroxyursolic acid (2), 2alpha,3alpha,24-trihydroxyurs-12-en-28-oic acid (3), and 2alpha,3alpha,19alpha,24-tetrahydroxyurs-12-en-28-oic acid-28-O-beta-D-glucopyranosyl ester (5), were isolated from the leaves of Prunus serrulata var. spontanea (Rosaceae). Compounds 3-5 showed ONOO(-) scavenging activity, whereas compounds 1 and 2 were virtually inactive. 相似文献
15.
Fu H Koike K Zheng Q Mitsunaga K Jia Z Nikaido T Lin W Guo D Zhang L 《Chemical & pharmaceutical bulletin》2001,49(8):999-1002
Five new triterpenoid saponins, fargosides A, B, C, D, and E, were isolated from the roots of Holboellia fargesii. The structures of fargosides A-E were elucidated on the basis of chemical and physicochemical evidence and found to be 3beta,20alpha-dihydroxy-29-norolean-12-en-28-oic acid 3-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (1), 3beta,20alpha,24-trihydroxy-29-norolean-12-en-28-oic acid 23-O-beta-D-fucopyranosyl-(1-->2)-[alpha-L-arabinopyranosyl-(1-->3)]-beta-D-glucopyranoside (2), 3beta,23-dihydroxy-30-norolean-2,20(29)-dien-28-oic acid 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-glucopyranosyluronic acid-(1-->3)]-alpha-L-arabinopyranoside (3), 3beta,23-dihydroxy-30-norolean-12,20(29)-dien-28-oic acid 3-O-methyl beta-D-glucopyranosyluronate-(1-->3)-alpha-L-arabinopyranoside (4), and 3beta,23-dihydroxy-olean-12-en-28-oic acid 3-O-methyl beta-D-glucopyranosyluronate-(1-->3)-alpha-L-arabinopyranoside (5), respectively. 相似文献
16.
From the commercial extract of the leaves of Stevia rebaudiana, two additional new diterpenoid glycosides were isolated and their structures were characterized as 13-[(2-O-beta-glucopyranosyl-3-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid beta-D-glucopyranosyl ester (1) and 13-[(2-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid beta-D-glucopyranosyl ester (2) on the basis of extensive spectral data (NMR and MS) and chemical studies. 相似文献
17.
Wang XL Hay AE Matheeussen A Gupta MP Hostettmann K 《Magnetic resonance in chemistry : MRC》2011,49(4):184-189
Phytochemical investigation of dichloromethane (DCM) extract from the stems of Paragonia pyramidata var. pyramidata L. Rich. (Bur.) resulted in the isolation and characterization of two new triterpenoids 3β,19β-dihydroxylup-12, 20(29)-diene-28-oic acid (1) and 3β,19β-dihydroxylup-12-en-28-oic acid (2), three known triterpenoids lupeol (3), spinosic acid A (4) and oleanolic acid (5), together with four known steroids (20R)-22E-24-ethylcholesta-4,22-dien-3-one (6), (20R)-24-ethylcholest-4-en-3-one (7), stigmasterol (8) and β-sitosterol (9). HREIMS, GC-MS and NMR experiments including HSQC, HMBC, COSY and NOESY were used for the determination of the structures and NMR spectral assignments. This is the first report about the chemical constituents for this plant. 相似文献
18.
Min Yin Xiangyun Wang Ming Wang Yu Chen Yunfa Dong Youyi Zhao Xu Feng 《Chemistry of Natural Compounds》2012,48(2):258-261
A new triterpenoid saponin, 3β,29-dihydroxy-olean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester (1), together with four known triterpenoid saponins, i.e., oleanolic acid 28-O-β-D-glucoside (2), chikusetsusaponin IVa methyl ester (3), calenduloside E (4), and calenduloside E 6'-methyl ester (5), was isolated from Salicornia europaea Linn. Their structures were elucidated on the basis of spectral analysis. 相似文献
19.
Sensen Yan Haijun Lin Huilian Huang Min Yang Bohui Xu 《Natural product research》2019,33(13):1849-1855
Biotransformation of oleanolic acid (OA) by Circinella muscae AS 3.2695 was investigated. Nine hydroxylated and glycosylated metabolites (1–9) were obtained. Their structures were elucidated as 3β,7β-dihydroxyolean-12-en-28-oic acid (1), 3β,7β,21β-trihydroxyolean-12-en-28-oic acid (2), 3β,7α,21β-trihydroxyolean-12-en- 28-oic acid (3), 3β,7β,15α-trihydroxyolean-12-en-28-oic acid (4), 7β,15α-dihydroxy- 3-oxo-olean-12-en-28-oic acid (5), 7β-hydroxy-3-oxo-olean-12-en-28-oic acid (6), oleanolic acid-28-O-β-D-glucopyranosyl ester (7), 3β,21β-dihydroxyolean-12-en-28- oic acid-28-O-β-D-glucopyranosyl ester (8), and 3β,7β,15α-trihydroxyolean-12-en- 28-oic acid-28-O-β-D-glucopyranosyl ester (9) by spectroscopic analysis. Among them, compounds 4 and 9 were new compounds. In addition, anti-inflammatory activities were assayed and evaluated for the isolated metabolites. Most of the metabolites exhibited significant inhibitory activities on lipopolysaccharides-induced NO production in RAW 264.7 cells. 相似文献
20.
Five constituents including one new pentacyclic triterpenoid guajanoic acid (1) and four known compounds beta-sitosterol (2), uvaol (3), oleanolic acid (4), and ursolic acid (5) have been isolated from the leaves of Psidium guajava. The new constituent 1 has been characterized as 3beta-p-E-coumaroyloxy-2alpha-methoxyurs-12-en-28-oic acid through 2D NMR techniques and chemical transformations. This is the first report of isolation of compound 3 from the genus Psidium. 相似文献