3391-81-9Relevant academic research and scientific papers
Facile synthesis of oleanolic acid monoglycosides and diglycosides
Sha, Yu,Yan, Mao-Cai,Liu, Jiao,Liu, Yang,Cheng, Mao-Sheng
, p. 1472 - 1486 (2008)
Oleanolic acid and its glycosides are important natural products, possessing various attractive biological activities such as antitumor, antivirus and anti-inflammatory properties. In the present work, fifteen oleanolic acid saponins bearing various sacch
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.
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
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.
New triterpene glycosides of Clematis montana and their cytotoxic activities
Jangwan,Dobhal, Maneesha
experimental part, p. 313 - 316 (2009/06/25)
Two new triterpene glycosides designated as montanosides 1 and 2 were isolated from methanolic extract of Clematis montana. Their structures have been elucidated as 3-O-β-D-glucopyranosyl-oleanolic acid-28-O-β-D- glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)] -β-D-xylopyranoside and 3-O-β-D-glucopyranosyl-oleanolic acid-28-O-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3) -α-L-rhamnopyranosyl-(1→2)]-β-D-xylopyranoside, respectively by NMR and MS data. Cytotoxic activity of the compounds were evaluated against various squamous carcinoma cells (HSC-2) and human gingival fibroblast cells (HGF). Both of the compounds showed potent cytotoxic activity against the test cells.
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 (2007/10/03)
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.
