Structures of three new oleanene glucuronides isolated from Lathyrus palustris var

Author(s): Udayama M, Ohkawa M, Yoshida N, Kinjo J, Nohara T

Abstract

Three new saponins, named palustrosides I, II and III, together with azukisaponins II, V and soyasapogenol B monoglucuronide, were isolated from the aerial parts of Lathylus palustris L. var. pilosus Ledeb. The structures of palustrosides I, II and III were identified as 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosides of soyasapogenol E, abrisapogenol E, and bredemolic acid 28-O-beta-D-glucopyranoside, respectively, by spectroscopic and chemical methods. As part of our studies on hepatoprotective drugs, we also examined the hepatoprotective effects of these saponins towards immunologically induced liver injury in primary cultured rat hepatocytes. The activity of the disaccharide group was greater than that of the trisaccharide group. This information regarding the structure-activity relationships substantiated previously obtained data. Structure-hepatoprotective relationships for the sapogenol moiety suggested that the hydroxyl group at C-30 reduces the hepatoprotective effect. On the other hand, the carbonyl group at C-22 may be equivalent to a hydroxyl group at C-22 in terms of hepatoprotective action. Oleanolic acid-type saponins also exhibited hepatoprotective action.

Similar Articles

The biological action of saponins in animal systems: a review

Author(s): Francis G, Kerem Z, Makkar HP, Becker K

Saponins, classification and occurrence in the plant kingdom

Author(s): Vincken JP, Heng L, de Groot A, Gruppen H

Naturally occurring triterpenoid saponins

Author(s): Dinda B, Debnath S, Mohanta BC, Harigaya Y

Triterpenenoid Saponins and their genins

Author(s): Agarwal SK, Rastogi RP

Triterpenoid saponins and sapogenins: 1973-1978

Author(s): Chandel RS, Rastogi RP

Steroid Saponins

Author(s): Mahato SB, Ganguly AN, Sahu NP

Bacopasides III-V: Three New Triterpenoid Glycosidesfrom Bacopa monniera

Author(s): Chakravarty AK, Garai S, Masuda K, Nakane T, Kawahara N

Molecular weight determinations of proteins by californium plasma desorption mass spectrometry

Author(s): Sundqvist B, Roepstorff P, Fohlman J, Hedin A, Håkansson P, et al.

Polyacetyleneginsenoside-RO; a novel triterpene saponin from Panax ginseng

Author(s): Zhang H, Lu Z, Tan GT, Qiu S, Farnsworth NR et al.

Two New Bidesmoside Triterpenoid Saponins from the Seeds of Momordica charantia

Author(s): Ma L, Yu AH, Sun LL, Gao W, Zhang MM et al.

New triterpenoid saponins from the roots of Saponaria officinalis

Author(s): Moniuszko-Szajwaj B, Pecio L, Kowalczyk M, Simonet AM, Macias FA, et al.

Antifungal jujubogenin saponins from Colubrina retusa

Author(s): Li XC, ElSohly HN, Nimrod AC, Clark AM

Molluscicidal saponins from Anagallis arvensis against schistosome intermediate hosts

Author(s): Abdel-Gawad MM, El-Amin SM, Ohigashi H, Watanabe Y, Takeda N, et al.

Molluscicidal saponins from Pometia Eximia

Author(s): Jayasinghe ULB, Fujimoto Y, Hostettmann K

Three anti-tumor saponins from Albizia julibrissin

Author(s): Zheng L, Zheng J, Zhao Y, Wang B, Wu L, et al.

A cytotoxic triterpene saponin from the root bark of Aralia dasyphylla

Author(s): Xiao K, Yi YH, Wang ZZ, Tang HF, Li YQ, et al.

Cytotoxic triterpenoid glycosides from the roots of Camellia oleifera

Author(s): Li X, Zhao J, Peng C, Chen Z, Liu Y, et al.

Bioactive Saponins and Glycosides III

Author(s):  Yoshikawa M, Murakami T, Matsuda H, Yamahara J, Murakami N, et al.

Bioactive Saponins and Glycosides III

Author(s): Yoshikawa M, Murakami T, Matsuda H, Yamahara J, Murakami N, et al.

Assamicin I and II, Novel Triterpenoid Saponins with Insulin-Like activity from Aesculus assamica Griff

Author(s):  Sakurai T, Nishimura T, Otake N, Xinsheng Y, Abe K, et al.

Hypoglycemic Activity of Some Triterpenoid Glycosides

Author(s): Kako M, Miura T, Nishiyama Y, Ichimaru M, Moriyasu M, et al.

Assamicin I and II, Novel Triterpenoid Saponins with Insulin-Like activity from Aesculus assamica Griff

Author(s): Sakurai T, Nishimura T, Otake N, Xinsheng Y, Abe K, et al.

Protective role of Bacopa monniera on morphine induced hepatotoxicity in rats

Author(s): Sumathy T, Subramanian S, Govindasamy S, Balakrishna K, Veluchamy G

Hepatoprotective triterpenoid saponins from Callicarpa nudiflora

Author(s): Huang B, Fu HZ, Chen WK, Luo YH, Ma SC

Hepatoprotective triterpenoids and saponins of Schefflera kwangsiensis

Author(s): Wang Y, Zhang CL, Liu YF, Liang D, Luo H, et al.

Anti-HIV-1 protease triterpenoid saponins from the seeds of Aesculus chinensis

Author(s): Yang XW, Zhao J, Cui YX, Liu XH, Ma CM, et al.

Antiallergic activity of ginseng and its ginsenosides

Author(s): Choo MK, Park EK, Han MJ, Kim DH

Biosynthesis of isoprenoids via the non-mevalonate pathway

Author(s): Eisenreich W, Bacher A, Arigoni D, Rohdich F

Ginsenosides in Hairy roots of a Panax hybrid

Author(s): Washida D, Shimomura K, Nakajima Y, Takido M, Kitanaka S

Ginsenoside production in different phenotypes of Panax ginseng transformed roots

Author(s): Mallol A, Cusidó RM, Palazón J, Bonfill M, Morales C, et al.

Structures of two novel isomeric triterpenoid saponins from Anthocephalus cadamba

Author(s): Sahu NP, Koike K, Jia Z, Achari B, Banerjee S, et al.

Structure of a Further Triterpene Saponin from Arenaria fillicaulis

Author(s): Toth G, Simon A, Elganal MHA, Soliman SM, Elmunajjed DT, et al.

Kahiricosides II-V, cycloartane glycosides from an Egyptian collection of Astragalus kahiricus

Author(s): Radwan MM, El-Sebakhy NA, Asaad AM, Toaima SM, Kingston DG

Triterpenoid saponins from the stem bark of Elattostachys apetala

Author(s): Lavaud C, Crublet ML, Pouny I, Litaudon M, Sévenet T

Sulfated triterpene derivatives from Fagonia arabica

Author(s): Perrone A, Masullo M, Bassarello C, Hamed AI, Belisario MA, et al.

Triterpenoid saponins from Fagonia cretica

Author(s): Abdel Khalik SM, Miyase T, El-Ashaal HA, Melek FR

Two new nor-triterpene glycosides from peruvian "Uña de Gato" (Uncaria tomentosa)

Author(s): Kitajima M, Hashimoto K, Yokoya M, Takayama H, Sandoval M, et al.

Triterpenoid saponins and sapogenins from Vaccaria segetalis

Author(s): Jia Z, Koike K, Kudo M, Li H, Nikaido T

Three new oleanane saponins from Zanha africana

Author(s): Cuéllar MJ, Giner RM, Recio MC, Just MJ, Máñez S, et al.