共查询到20条相似文献,搜索用时 31 毫秒
1.
Murakami T Nakamura J Kageura T Matsuda H Yoshikawa M 《Chemical & pharmaceutical bulletin》2000,48(11):1720-1725
Following the investigation of assamsaponins A, B, C, D, and E, four new saponins termed assamsaponins F, G, H, and I were isolated from the seeds of the tea plant (Camellia sinensis L. var. assamica PIERRE), while assamsaponin J was isolated from its leaves. The structures of assamsaponins F-J were elucidated on the basis of chemical and physicochemical evidence and found to be 16,22-O-diacetyl-21-O-angeloyltheasapogenol E 3-O-[beta-D-galactopyranosyl (1-->2)][beta-D-glucopyranosyl(1 -->2)- alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, 21-O-angeloyl-22-O-acetyltheasapogenol E 3-O-[beta-D-galactopyranosyl(1--> 2)][beta-D-glucopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->3)]- beta-D-glucopyranosiduronic acid, 21-O-angeloyl-28-O-acetyltheasapogenol E 3-O-[beta-D-galactopyranosyl(1-->2)][beta-D-glucopyranosyl(1--> 2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, 21-O-tigloyl-28-O-acetyltheasapogenol E 3-O-[beta-D-galactopyranosyl(1--> 2)][beta-D-glucopyranosyl(1--> 2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, and 16,21-O-diacetyl-22-O-cinnamoyltheasapogenol B 3-O-[beta-D-galactopyranosyl(l-->2)][beta-D-rhamnopyranosy(1-->2)- alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, respectively. The saponin mixture from the seeds of the tea plant was found to exhibit an inhibitory effect on gastric emptying and an accelerating effect on gastrointestinal transit in mice. Theasaponin E1 the principle saponin of the tea plant, showed potent activity, while theasaponin E2 showed none, so that the position of the acyl groups in the sapogenin moiety is important from a pharmacological point of view. 相似文献
2.
Yoshikawa M Morikawa T Li N Nagatomo A Li X Matsuda H 《Chemical & pharmaceutical bulletin》2005,53(12):1559-1564
The saponin fraction from the seeds of the tea plant [Camellia sinensis (L.) O. KUNTZE (Theaceae)] was found to exhibit potent protective effects on ethanol- and indomethacin-induced gastric mucosal lesions in rats. Five new triterpene saponins, theasaponins E3 (1), E4 (2), E5 (3), E6 (4), and E7 (5), were isolated together with 11 known saponins from the saponin fraction. The chemical structures of 1-5 were elucidated on the basis of chemical and physicochemical evidence. Among the isolated saponins, theasaponins E1 (6), E2 (7), and E5 (3) and assamsaponin C (10) showed an inhibitory effect on ethanol-induced gastric mucosal lesions at a dose of 5.0 mg/kg, p.o. and their activities were stronger than that of omeplazole. With regard to the structure-activity relationships of theasaponins, the following structural requirements for a protective effect on ethanol-induced gastric lesions were suggested; 1) the 21- and/or 22-acyl groups are essential for the activity, 2) acetylation of the 16-hydroxyl group reduce the activity. 相似文献
3.
M Yoshikawa T Murakami A Kishi T Kageura H Matsuda 《Chemical & pharmaceutical bulletin》2001,49(7):863-870
The methanolic extract and its 1-butanol-soluble fraction from the flowers of Calendula officinalis were found to show a hypoglycemic effect, inhibitory activity of gastric emptying, and gastroprotective effect. From the 1-butanol-soluble fraction, four new triterpene oligoglycosides, calendasaponins A, B, C, and D, were isolated, together with eight known saponins, seven known flavonol glycosides, and a known sesquiterpene glucoside. Their structures were elucidated on the basis of chemical and physicochemical evidence. The principal saponin constituents, glycosides A, B, C, D, and F, exhibited potent inhibitory effects on an increase in serum glucose levels in glucose-loaded rats, gastric emptying in mice, and ethanol- and indomethacin-induced gastric lesions in rats. Some structure-activity relationships are discussed. 相似文献
4.
Yoshikawa M Murakami T Oomiinami H Matsuda H 《Chemical & pharmaceutical bulletin》2000,48(7):1045-1050
The saponin fraction from the fresh leaves of Euiptelea polyandra Sieb. et Zucc. was found to exhibit potent gastroprotective activity. Fourteen new nortriterpene saponins called eupteleasaponins were isolated from the saponin fraction with gastroprotective activity. The structures of eupteleasaponins I, I1, III, IV, V, and V acetate were determined on the basis of chemical and physicochemical evidence as 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl(1 -->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl(1-->2)-[alpha-L-rhamnopyranosyl(1 -->4)-beta-D-glucopyranosyl(1-->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D- D-glucopyranosyl(1-->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-rhamnopyranosyl(1 -->4)-beta-D-glucopyranosyl(1-->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl(1 -->2)-[alpha-L-arabinopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-- >4)]-beta-D- glucopyranosyl(1-->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosvl(1-->2)-[alpha-L-arabinopyranosyl (1 -->4)-beta-L-rhamnopyranosyl(1 -->4)]-beta-D-glucopyranosyl(1 -->3)-beta-D-xylopyranosylakebonoic acid, 3-O-alpha-L-rhamnopyranosyl(1 -->2)-beta-D-glucopyranosvl(1-->3)-beta-D-xylopyranosyleupteleo genin, and 3-O-alpha-L-rhamnopyranosyl(1-->2)-6"-O-acetyl-gamma-D-glucopyranosyl(1 -->3)-beta-D-xylopyranosyleupteleogenin. 相似文献
5.
Matsuda H Nakamura S Fujimoto K Moriuchi R Kimura Y Ikoma N Hata Y Muraoka O Yoshikawa M 《Chemical & pharmaceutical bulletin》2010,58(12):1617-1621
The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia sasanqua THUNB. were found to show inhibitory activities on the release of β-hexosaminidase from rat basophile leukemia (RBL-2H3) cells. From the 1-butanol-soluble fraction, five new acylated oleanane-type triterpene saponins, sasanquasaponins I-V, were isolated together with a known saponin and their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The principal saponin constituents, sasanquasaponins I-III, with an acyl group at the 22-position of the aglycon part showed the inhibitory effects on the release of β-hexosaminidase and some structure-activity relationships were reported. 相似文献
6.
Five paeonol glycosides, suffruticosides A, B, C, D, and E, and a monoterpene glucoside, galloyl-oxypaeoniflorin, were isolated from the glycosidic fraction of Chinese Moutan Cortex, the root cortex of Paeonia suffruticosa Andrews, together with paeonolide, apiopaeonoside, galloyl-paeoniflorin, oxypaeoniflorin, and paeoniflorin. The structures of five suffruticosides and galloyl-oxypaeoniflorin were elucidated on the basis of chemical and physicochemical evidence. Suffruticosides A, B, C, and D, galloyl-oxypaeoniflorin, and galloyl-paeoniflorin exhibited more potent radical scavenging effects than alpha-tocopherol. 相似文献
7.
8.
Lobatoside E, a novel and complex cyclic triterpene saponin showing potent antitumor activities, has been synthesized for the first time, employing a highly modular approach. The synthesis, starting with oleanolic acid, D-glucose, D-galactose, L-arabinose, and L-rhamnose, requires a total of 73 steps, with the longest linear sequence of 31 steps and in 1.2% overall yield. 相似文献
9.
10.
Toshio Morikawa Hisashi Matsuda Ning Li Xian Li Masayuki Yoshikawa 《Helvetica chimica acta》2007,90(12):2342-2348
Three new acylated oleanane‐type triterpene saponins, theasaponins A6 ( 1 ), A7 ( 2 ), and B5 ( 3 ), were isolated from the saponin fraction of the seeds of the Japanese tea plant Camellia sinensis together with the known constituent foliatheasaponin III ( 4 ). The structures of the glycosides 1 – 3 were elucidated on the basis of spectroscopic, chemical, and physico‐chemical evidence. 相似文献
11.
Wei F Ma LY Jin WT Ma SC Han GZ Khan IA Lin RC 《Chemical & pharmaceutical bulletin》2004,52(10):1246-1248
Phytochemical study of the ethanol extract of the seeds of Aesculus chinensis led to the isolation of a new triterpenoid saponin (6), together with five known triterpenoid saponins (1-5). The structure of the new compound was elucidated on the basis of spectral data to be 21,28-di-O-acetylprotoaescigenin-3-O-[beta-D-glucopyranosyl(1-2)][beta-D-glucopyranosyl(1-4)]-beta-D-glucopyranosiduronic acid (aesculiside A, 6). The antiinflammatory activities of the four main saponins (1-4) were compared with those of total saponin extracts, and single saponins showed more potent activity than total saponin extracts in mice. 相似文献
12.
The present study was carried out to elucidate the anti-inflammatory effect of the methanol extract obtained from the rhizomes of Zingiber cassumunar Roxb. and its active principles. The methanol extract was partitioned between ether and water, and then the ether-soluble fraction was extracted with n-hexane. The n-hexane-soluble fraction was chromatographed and part of the fraction was rechromatographed by silica gel column. Three compounds were isolated from the n-hexane-soluble fraction and the chemical structures of these compounds were identified as (E)-1-(3,4-dimethoxyphenyl)but-1-ene, (E)-1-(3,4-dimethoxyphenyl)butadiene and zerumbone. The anti-inflammatory activity of these fractions was investigated on carrageenin-induced edema in rats, as well as on acetic acid-induced vascular permeability and writhing symptoms in mice. The methanol extract (p.o.) showed both anti-inflammatory activity and analgesic activity. These activities shifted successively to ether-soluble and n-hexane-soluble fractions and to (E)-1-(3,4-dimethoxyphenyl)but-1-ene. These results suggest that the anti-inflammatory action and analgesic action of Zingiber cassumunar is the result of the (E)-1-(3,4-dimethoxyphenyl)but-1-ene that it contains. 相似文献
13.
The highly potent anticancer natural saponin OSW-1 has been successfully synthesized from commercially available 5-androsten-3beta-ol-17-one 79 in 10 operations with 28% overall yield. The key steps in the total synthesis included a highly regio- and stereoselective selenium dioxide-mediated allylic oxidation of 80 and a highly stereoselective 1,4-addition of alpha-alkoxy vinyl cuprates 68 to steroid 17(20)-en-16-one 12E to introduce the steroid side chain. This total synthesis demonstrated once again the versatile synthetic applications of alpha-halo vinyl ether chemistry developed in our laboratories. 相似文献
14.
Ha YW Lim SS Ha IJ Na YC Seo JJ Shin H Son SH Kim YS 《Journal of chromatography. A》2007,1151(1-2):37-44
Ginseng (Panax ginseng C. A. Meyer) has been well known to have a variety of ginsenosides that show diverse biological activities. Especially, the components of ginsenosides are quite different depending on the processing method. Recently, there have been several reports showing that less polar ginsenosides from Korean red ginseng (steam-treated Panax ginseng) have potent biological activities such as radical scavenging, vasodilating and anti-tumor activities. In this study, we have isolated four known ginsenosides Rg3, Rk1, Rg5 and F4 from Korean red ginseng by high-speed counter-current chromatography (HSCCC) coupled with evaporative light scattering detection (ELSD). The enriched saponin fraction (350 mg) was separated by using methylene chloride-methanol-water-isopropanol (6:6:4:1, v/v) as the two-phase solvent system and yielded 28.6 mg of Rg5, 26.6 mg of Rk1, 32.2 mg of Rg3 and 8.1 mg of F4. The purity of these ginsenosides was assessed by HPLC-ELSD to be over 95%, and their structures were characterized by electrospray ionization mass spectrometry (ESI-MS), (1)H NMR and (13)C NMR. 相似文献
15.
The hydrolysis of protopanaxadiol-type saponin mixture by various glycoside hydrolases was examined. Among these enzymes, crude preparations of lactase from Aspergillus oryzae, beta-galactosidase from A. oryzae, and cellulase from Trichoderma viride were found to produce ginsenoside F(2) [3-O-(beta-D-glucopyranosyl)-20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol], compound K [20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol], and ginsenoside Rd {3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol}, respectively, from protopanaxadiol-type saponin mixture in large quantities. Moreover, the crude preparation of lactase from Penicillium sp. having a high producing activity of ginsenoside Rh(1) (6-O-beta-D-glucopyranosyl-20(S)-protopanaxatriol) from protopanaxatriol-type saponin mixture gave ginsenoside Rd as a main product, ginsenoside Rg(3) {3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-20(S)-protopanaxadiol}, and compound K from protopanaxadiol-type saponin mixture. The hydrolytic pathways of ginsenosides Rb(1), Rb(2), and Rc to ginsenosides Rd, Rg(3), and F(2), and compound K by crude preparations of four glycoside hydrolases were also studied. This is the first report on the enzymatic preparation of an intestinal bacterial metabolite, ginsenoside F(2), in quantity, and a considerable amount of a minor saponin, ginsenoside Rg(3), from a protopanaxadiol-type saponin mixture. 相似文献
16.
A spectrophotometric method was developed for the determination of saponin in Yucca extract or its preparation for food additive use. A saponin fraction of Yucca extract was prepared by column chromatography with porous polymer, and hydrolyzed with a 2 mol/L mixture of hydrochloric acid-ethanol (1 + 1) to generate sapogenin. Sapogenin amounts were determined by measuring absorbance at 430 nm, based on the color reactions with anisaldehyde, sulfuric acid, and ethyl acetate. Recoveries from Yucca extracts were 91.5-95.1%, and the detection limit was 10 microg/kg. Commercial Yucca extracts for food additive use were composed of 5.6-6.4% (w/w) saponin, making it a minor component. 相似文献
17.
A new and practical method was developed to synthesize OSW-1, a natural saponin with potent antitumor activities, from (+)-dehydroisoandrosterone, l-arabinose, and D-xylose on gram scale. The synthesis was achieved in 10 linear steps with an overall yield of 6.4% starting from (+)-dehydroisoandrosterone. 相似文献
18.
Kim JS Shim SH Chae S Han SJ Kang SS Son KH Chang HW Kim HP Bae K 《Chemical & pharmaceutical bulletin》2005,53(6):696-700
A new triterpenoid saponin, together with five known saponins, were isolated from the nonpolar n-hexane fraction of the leaves of Aralia elata. The structure of the new saponin, durupcoside C, was elucidated as hederagenin 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranoside on the basis of spectroscopic analysis. The known saponins were characterized as 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl hederagenin 28-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranosyl ester, hederagenin 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside, oleanolic acid 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside, hederagenin 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside (alpha-hederin), and hederagenin 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranoside (collinsonidin). In addition, two known lipids, Arisaema glyceride 3 and ceramide mixtures were also isolated and characterized. Collinsonidin and two known lipids were isolated for the first time from this plant. 相似文献
19.
Tanaka O Han EC Yamaguchi H Matsuura H Murakami T Taniyama T Yoshikawa M 《Chemical & pharmaceutical bulletin》2000,48(6):889-892
Panax pseudo-ginseng subsp. pseudo-ginseng has a carrot like root with a small rhizome. It was shown that the saponin composition of roots and rhizomes of this subspecies collected in Tibet and China was extremely poor. From the roots and rhizomes collected in Central Nepal, (specimen-PNct), only a small amount of an oleanolic acid saponin, beta-D-glucopyranosyl-oleanolate (2) was isolated together with a polyacetylene-alcohol, panaxynol (3). In another specimen (specimen-PNs), also collected in Central Nepal, two oleanolic acid saponins, stipleanoside R2 (4) and chikusetsusaponin IV (5) were detected. No dammarane saponin was identified in either specimen. P. pseudo-ginseng subsp. himalaicus (Subsp-H) has a big rhizome with a small round root. From rhizomes and roots of this subsp. collected in Central Nepal (specimen-HNct), a fairly large amount of dammarane saponins, ginsenosides-Rb1 (6), -Rd (7), -Re (9) and -Rg1 (10), gypenoside XVII (8), notoginsenoside-R1 (11), majonoside-R2 (12) and pseudo-ginsenoside-F11 (13) were isolated, while no oleanane saponin (oleanolic acid saponin) was identified in this subsp. Based on the present and previous studies, medicinal evaluation and chemogeographical correlation of Himalayan Panax spp. are discussed. 相似文献
20.
Pancreatic lipase-inhibiting triterpenoid saponins from fruits of Acanthopanax senticosus 总被引:1,自引:0,他引:1
Sixteen triterpenoid saponins were isolated from the fruits of Acanthopanax senticosus, including a new compound, acanthopanaxoside E (1), which was established as 3-O-beta-D-glucuronopyranosyl echinocystic acid 28-O-beta-D-glucopyranoside on the basis of various spectroscopic analyses and chemical degradation. By using a pancreatic lipase-inhibiting assay system, the crude saponin fraction showed inhibitory activity on pancreatic lipase, which is a key enzyme in lipid digestion. Among the isolated compounds, silphioside F (2), copteroside B (3), hederagenin 3-O-beta-D-glucuronopyranoside 6'-O-methyl ester (4) and gypsogenin 3-O-beta-D-glucuronopyranoside (5) showed inhibitory activity toward pancreatic lipase with IC(50) values of 0.22, 0.25, 0.26 and 0.29 mM, respectively, and the free carboxylic acid groups in position 28 within their chemical structures were required for enhancement of pancreatic lipase inhibition. 相似文献