15596-19-7Relevant academic research and scientific papers
Antidiabetic principles of natural medicines. III. Structure-related inhibitory activity and action mode of oleanolic acid glycosides on hypoglycemic activity
Matsuda, Hisashi,Li, Yuhao,Murakami, Toshiyuki,Matsumura, Narumi,Yamahara, Johji,Yoshikawa, Masayuki
, p. 1399 - 1403 (1998)
We examined the structure-related activity of oleanolic acid glycosides with respect to their inhibitory effect on the increase in serum glucose in oral glucose-loaded rats and their mechanism of action using oleanolic acid 3-O-glucuronide and momordin Ic. Both the 3-O-monodesmoside structure and 28- carboxyl group were confirmed to be essential for such activity, and the 3- O-glucuronide was more potent than 3-O-glucoside. On the other hand, the 28- ester glucoside moiety and 6'-methyl ester of the glucuronide moiety reduced such activity. Oleanolic acid 3-O-glucuronide and momordin I(c), both of which inhibited the increase in serum glucose in oral glucose-loaded rats, did not lower serum glucose in normal or intraperitoneal glucose-loaded rats, or alloxan-induced diabetic mice. These glycosides were found to suppress gastric emptying in rats, and also inhibit glucose uptake in the rat small intestine in vitro. These results indicate that oleanolic acid 3-O- glucuronide and momordin Ic, given orally, have neither insulin-like activity nor insulin releasing-activity. They exhibit their hypoglycemic activity by suppressing the transfer of glucose from the stomach to the small intestine and by inhibiting glucose transport at the brush border of the small intestine.
Triterpenoid saponins of Acanthopanax nipponicus leaves
Miyakoshi, Masazumi,Shirasuna, Katsuya,Hirai, Yasuaki,Shingu, Kazushi,Isoda, Susumu,Shoji, Junzo,Ida, Yoshiteru,Shimizu, Torao
, p. 445 - 448 (1999)
Five new triterpenoid saponins, nipponosides A-E (1, 3-6), were isolated from Acanthopanax nipponicus leaves, along with a known saponin, kalopanaxsaponin G (2). Nipponosides A-E were characterized as the 28-O-α- L-rhamnopyranosyl(1-4)-β-D-glucopyranosyl(16)-β-D-glucopyranosyl ester of 3-oxohederagenin, oleanolic acid 3-O-β-D-glucopyranoside, gypsogenin 3-O- β-D-glucopyranoside, 3β,23,29-trihydroxyolean-12-en-28-oic acid, and 3β,20α,23-trihydroxy-30-nor-olean-12-en-28-oic acid, respectively. The structures of these new compounds were based on chemical and spectral methods.
Asteryunnanosides F and G: Two new triterpenoid saponins from Aster yunnanensis
Shao,Zhou,Lin,Cordell
, p. 446 - 449 (1995)
Two new triterpenoid saponins, asteryunnanosides F and G, were isolated from the roots of Aster yunnanensis. Their structures were determined as oleanolic acid-28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside and 3-O-β-glucopyranosyloleanolic acid-28-O-β-D-glucopyranosyl-(1→6)-[α-L-rhamnopyranosyl-(1→2)]-β- D-glucopyranoside by spectral data, especially 2D NMR analysis including COSY, HETCOR, HOHAHA, and ROESY techniques, and chemical transformation.
TRITERPENOID SAPONINS FROM FRUIT OF LAGENARIA BREVIFLORA
Elujoba, Anthony A.,Fell, Anthony F.,Linley, Peter A.,Maitland, Derek J.
, p. 3281 - 3285 (1990)
From the methanol extract of the fruit pulp of Lagenaria breviflora, three new saponins were characterized as 3-O-β-galactopyranosyl 28-O-β-xylopyranosyl(1-4)-α-rhamnopyranosyl(1-3)-β-xylopyranosyl(1-3)-α-arabinopyranopsylolean-12-en-28-oic acid ester, 3-O-β-galactopyranosyl 28-O-β-galactopyranosyl(1-4)-α-rhamnopyranosyl(1-3)-β-xylopyranosyl(1-3)-α-arabinopyranosylolean-12-en-28-oic acid ester and 3-O-β-galactopyranosyl 28-O-α-arabinopyranosyl(1-6)-β-galactopyranosyl(1-4)-α-rhamnopyranosyl(1-3)-β-xylopyranosyl(1-3)-α-arabinopyranosylolean-12-en-28-oic acid ester.Oleanolic acid and 3-O-acetyloleanolic acid were identified from the hydrolytic products of the pulp.
New triterpenoid saponin glycosides from the fruit fibers of: Trichosanthes cucumerina L.
Chulrik, Wanatsanan,Chunglok, Warangkana,Li, Jian-Xin,Suebsakwong, Parichat,Suksamrarn, Apichart,Yao, Zhu-Jun
, p. 10461 - 10470 (2020/03/27)
Five new triterpenoid saponin glycosides, trichocucumerisides A-E (1-5), together with eleven known compounds (6-16) were isolated from Trichosanthes cucumerina fruit fibers. The structures of the new compounds were elucidated by detailed analysis of NMR and mass spectroscopic data as well as chemical reactions. The anti-inflammatory study against nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 cells shows that compounds 7 and 9 exhibited stronger NO inhibitory activity, with IC50 values of 3.0 and 2.7 μM, respectively, with comparison to positive references Celecoxib and aminoguanidine (IC50 values 75.7 and 75.0 μM, respectively). Compounds 7 and 9 also possessed a greater selectivity index (SI) of approximately 3-4-fold activity than that of the positive references.
Ionic liquid-assisted catalysis for glycosidation of two triterpenoid sapogenins
Zhang, Tenghe,Li, Xinlu,Song, Hang,Yao, Shun
, p. 16881 - 16888 (2019/11/14)
In order to both investigate the universality of ionic liquid-based catalytic systems for synthesis of triterpene saponins and explore their effective application methods together with the catalytic behaviors of ionic liquids in related reactions by comparison between different initiators, oleanolic acid and ursolic acid were selected to establish a catalytic system for glycosylation in this study as typical representatives of pentacyclic triterpene sapogenins. As a result, it was found that the system of [C4mim][OTf] + TMSOTf in the reactions between the glycosyl receptors and donors showed obvious catalytic effects; also, the system was stable and could be recycled. The functions of IL include solvent, cocatalyst and stabilizer, simultaneously; thus, the current catalytic system is greener, simpler and more efficient. The reaction time was short, and only β-type products were obtained. This study offers a reference for developing a new glucoside synthesis technology and provides sufficient preliminary exploration and basic data for further large-scale applications.
Synthesis and Evaluation of a Series of Oleanolic Acid Saponins as α-Glucosidase and α-Amylase Inhibitors
Guo, Tiantian,Wu, Shaoping,Guo, Sen,Bai, Lu,Liu, Qingchao,Bai, Naisheng
, p. 615 - 628 (2015/09/15)
Sixteen naturally occurring oleanolic acid saponins and their derivatives were synthesized in an efficient and practical strategy, and their inhibitory activities against α-glucosidase and α-amylase were evaluated in vitro. Among all the compounds, 28-O-m
Biotransformation of oleanolic acid by Alternaria longipes and Penicillium adametzi
Liu, Dai-Lin,Liu, Ying,Qiu, Feng,Gao, Ying,Zhang, Jing-Ze
experimental part, p. 160 - 167 (2011/04/15)
Microbial transformation of oleanolic acid (1) was carried out. Six transformed products (2-7) from 1 by Alternaria longipes and three transformed products (8-10) from 1 by Penicillium adametzi were isolated. Their structures were elucidated as 2,3,19-trihydroxy-ursolic acid-28-O - d-glucopyranoside (2), 2,3,19-trihydroxy-ursolic acid-28-O - d-glucopyranoside (3), oleanolic acid 28-O - d-glucopyranosyl ester (4), oleanolic acid-3-O - d-glucopyranoside (5), 3-O-(-d-glucopyranosyl)-oleanolic acid-28-O - d-glucopyranoside (6), 2,3,19a-trihydroxy-oleanolic acid-28-O - d-glucopyranoside (7), 21-hydroxyl oleanolic acid-28-O - d-glucopyranoside (8), 21-hydroxyl oleanolic acid (9), and 7,21-dihydroxyl oleanolic acid (10) based on the extensive NMR studies. Among them, 10 was a new compound and compounds 5 and 8-10 had stronger cytotoxic activities against Hela cell lines than the substrate. At the same time, it was reported for the first time in this paper that the skeletons of compounds 2 and 3 were changed from oleanane to uranane and seven glycosidation products were obtained by biotransformation.
USE OF URSOLIC ACID SAPONIN,OLEANOLIC ACID SAPONIN IN PREPARATION OF INCREASING LEUCOCYTES AND/OR PLATELET MEDICINE
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Page/Page column 6, (2010/08/08)
The invention provides the use of ursolic acid saponin and oleanolic acid saponin of formula (I) in preparing medicaments for increasing leucocytes and/or platelets. The invention also provides a pharmaceutical composition containing the same compound. The invention utilizes the cheap and accessible ursolic acid and oleanolic acid which are widely present in natural plants as raw materials, introduces monosaccharyls or oligosaccharyls by structural modification. It is proved by pharmacological tests that the compound of formula (I) have an activity of obviously increasing leucocytes and/or platelets.
Synthesis and α-glucosidase inhibitory activity of oleanolic acid derivatives
Qian, Shan,Hai Li, Jiao,Wei Zhang, Yu,Chen, Xin,Wu, Yong
scheme or table, p. 20 - 29 (2010/09/18)
Glucosidations of oleanolic acid (1) and its dihydroxy-olide derivatives (2) were carried out to provide eight glycosides. All synthesized compounds were evaluated by in vitro α-glucosidase inhibitory activity assay. 3-Acetyl dihydroxy-olide oleanolic der
