121468-30-2Relevant academic research and scientific papers
The chemical and biological potential of C ring modified triterpenoids
Siewert, Bianka,Wiemann, Jana,K?witsch, Alexander,Csuk, René
, p. 84 - 101 (2014)
A convenient and elegant route has been developed to separate the natural regioisomers triterpenoids ursolic acid (UA) and oleanolic acid (OA) as well as derivatives thereof. Eleven unknown derivatives of OA were designed, synthesized, and their cytotoxicity was investigated. Further sixteen compounds were prepared to correlate all compounds in a SAR study. It could be shown that C-ring modifications of OA and UA have only a moderate influence onto the cytotoxic activity of the compounds but a significant impact onto the ability to trigger apoptosis in ovarian cancer cells (cell line A2780).
Identification of three triterpenoids in almond hulls
Takeoka,Dao,Teranishi,Wong,Flessa,Harden,Edwards
, p. 3437 - 3439 (2000)
Three triterpenoids, betulinic acid, oleanolic acid, and ursolic acid, were isolated as their methyl esters (treatment with diazomethane) from diethyl ether extracts of almond hulls (Nonpareil variety) using flash chromatography and preparative high-performance liquid chromatography. The triterpenoids, which comprised ~1% of the hulls, were characterized using chromatographic and spectroscopic methods. These studies demonstrate that almond hulls are a rich source of these triterpenoids, which have reported anti-inflammatory, anti-HIV, and anti-cancer activities.
Synthesis and anti-cancer activity of some novel C-17 analogs of ursolic and oleanolic acids
Mallavadhani, Uppuluri V.,Mahapatra, Anita,Pattnaik, Banita,Vanga, Nagireddy,Suri, Nitasha,Saxena, Ajit K.
, p. 1263 - 1269 (2013)
A series of seventeen novel analogs of ursolic and oleanolic acid were synthesized (60-98 %), and evaluated for their anti-cancer potential against a panel of eight human cancer cell lines. Compounds (3-10) showed comparable or better activities than their respective parent compounds against SiHa and HeLa (Cervix), A-549 (Lung), and IMR-32 (Neuroblastoma) cancer cell lines. Significantly, among the bromoalkyl esters (11-19), compound 13 showed promising anti-cancer activity against Leukemia THP-1 cell line at 10 μM concentration. In this series, it is interesting to note that the increase in chain length has an adverse effect on the activity.
Ursolic and oleanolic acid derivatives with cholinesterase inhibiting potential
Loesche, Anne,K?witsch, Alexander,Lucas, Susana D.,Al-Halabi, Zayan,Sippl, Wolfgang,Al-Harrasi, Ahmed,Csuk, René
, p. 23 - 32 (2019)
Triterpenoids are in the focus of scientific interest, and they were evaluated for many pharmacological applications among them their ability to act as inhibitors of cholinesterases. These inhibitors are still of interest as drugs that improve the life quality of patients suffering from age-related dementia illnesses especially of Alzheimer's disease. Herein, we prepared several derivatives of ursolic and oleanolic acid and screened them in Ellman's assays for their ability to inhibit acetylcholinesterase and/or butyrylcholinesterase, and for each of the active compounds the type of inhibition was determined. As a result, several compounds were shown as good inhibitors for acetylcholinesterase and butyrylcholinesterase even in a micromolar range. An ursolic acid derived hydroxyl-propinyl derivative 10 was a competitive inhibitor for butyrylcholinesterase with an inhibition constant of Ki = 4.29 μM, and therefore being twice as active as gold standard galantamine hydrobromide. The best inhibitor for acetylcholinesterase, however, was 2-methyl-3-oxo-methyl-ursoloate (18), acting as a mixed-type inhibitor showing Ki = 1.72 μM and Ki′ = 1.28 μM, respectively.
3β,24-DIHYDROXYOLEAN-12-EN-28-OIC ACID, A PENTACYCLIC TRITERPENE ACID FROM LANTANA INDICA
Singh, S. K.,Tripathi, V. J.,Singh, R. H.
, p. 3360 - 3362 (1990)
A new oleanane derivative, 3β,24-dihydroxy olean-12-en-28-oic acid, in addition to oleanolic and ursolic acids, has been isolated from the roots of Lantana indica.The structure of the new triterpene acid has been established by chemical and spectroscopic methods.
An efficient synthesis of methyl 2-cyano-3,12-dioxoursol-1,9-dien-28-oate (CDDU-methyl ester): Analogues, biological activities, and comparison with oleanolic acid derivatives
Fu, Liangfeng,Lin, Qi-Xian,Liby, Karen T.,Sporn, Michael B.,Gribble, Gordon W.
, p. 5192 - 5200 (2014)
An efficient synthesis of methyl 2-cyano-3,12-dioxoursol-1,9-dien-28-oate (CDDU-methyl ester) from commercially available ursolic acid, which features an oxidative ozonolysis-mediated C-ring enone formation, and provides the first access to ursolic acid-derived cyano enone analogues with C-ring activation. These new ursolic acid analogues show potent biological activities, with potency of approximately five-fold less than the corresponding oleanolic acid derivatives.
Inhibitory effects of constituents from Cynomorium songaricum and related triterpene derivatives on HIV-1 protease
Ma, Chaomei,Nakamura, Norio,Miyashiro, Hirotsugu,Hattori, Masao,Shimotohno, Kunitada
, p. 141 - 145 (1999)
From CH2Cl2 and MeOH extracts of the stems of Cynomorium songaricum RUPR. (Cynomoriaceae), ursolic acid and its hydrogen malonate were isolated as inhibitors of human immunodeficiency virus type 1 (HIV-1) protease, with 50% inhibitory concentrations (IC50) of 8 and 6 μM, respectively. Amongst various synthesized dicarboxylic acid hemiesters of related triterpenes, inhibitory activity tended to increase in the order of oxalyl, malonyl, succinyl and glutaryl hemiesters, for triterpenes such as ursolic acid, oleanolic acid and betulinic acid. The most potent inhibition was observed for the glutaryl hemiesters, with an IC50 of 4 μM. From the water extract of the stems of C. songaricum, flavan-3-ol polymers, consisting of epicatechin as their extender flavan units, were also found to be potent inhibitory principles against HIV-1 protease.
URSANE TRITERPENOIDS FROM NEPETA ERIOSTACHIYA
Bhandari, S. P. S.,Garg, H. S.,Agrawal, P. K.,Bhakuni, D. S.
, p. 3956 - 3958 (1990)
From the aerial parts of Nepeta eriostachiya two rare ursane triterpenoids, 2α,3α-dihydroxyurs-12-en-28-oic acid and 2α,3β-dihydroxyurs-12-en-28-oic acid, together with a new triterpene, nepetoic acid identified as 2α-methoxy-3β-hydroxyurs-12-en-28-oic acid were isolated as their methyl esters.Their structures were established by chemical and spectroscopic means.
New enone derivatives of oleanolic acid and ursolic acid as inhibitors of nitric oxide production in mouse macrophages
Honda, Tadashi,Finlay, Heather J.,Gribble, Gordon W.,Suh, Nanjoo,Sporn, Michael B.
, p. 1623 - 1628 (1997)
New derivatives of 3-oxoolean-1-en-28-oic acid and 3-oxours-1-en-28-oic acid were synthesized. Nine of them showed significant inhibitory activity against interferon-γ-induced nitric oxide production in mouse macrophages when assayed at the 1 μM level. 3,12-Dioxoolean-1,9-dien-28-oic acid (3) had the highest activity (IC50, 0.9 μM).
Chemical phenotypes of the hmg1 and hmg2 mutants of Arabidopsis demonstrate the in-planta role of HMG-CoA reductase in triterpene biosynthesis
Ohyama, Kiyoshi,Suzuki, Masashi,Masuda, Kazuo,Yoshida, Shigeo,Muranaka, Toshiya
, p. 1518 - 1521 (2007)
Plants produce a wide variety of cyclic triterpenes, such as sterols and triterpenoids, which are the major products of the mevalonate (MVA) pathway. It is important to understand the physiological functions of HMG-CoA reductase (HMGR) because HMGR is the rate-limiting enzyme in the MVA pathway. We have previously isolated Arabidopsis mutants in HMG1 and HMG2. Although the biochemical function of HMGR2 has been thought to be almost equal to that of HMGR1, based on similarities in their sequences, the phenotypes of mutants in these genes are quite different. Whereas hmg2 shows no abnormal phenotype under normal growth conditions, hmg1 shows pleiotropic phenotypes, including dwarfing, early senescence, and male sterility. We previously postulated that the 50% decrease in the sterol content of hmg1, as compared to that in the wild type, was a cause of these phenotypes,1) but comprehensive triterpene profiles of these mutants had not yet been determined. Here, we present the triterpene profiles of hmg1 and hmg2. In contrast to hmg1, hmg2 showed a sterol content 15% lower than that of the wild type. A precise triterpenoid quantification using synthesized deuterated compounds of β-amyrin (1), α-amyrin (2), and lupeol (3) showed that the levels of triterpenoids in hmg1 and hmg2 were 65% and 25% lower than in the wild type (WT), respectively. These results demonstrate that HMGR2 as well as HMGR1 is responsible for the biosynthesis of triterpenes in spite of the lack of visible phenotypes in hmg2.
