- Straightforward partial synthesis of four diastereomeric 2,3-dihydroxy-olean-12-en-28-oic acids from oleanolic acid
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The four diastereomeric 2,3-dihydroxy-olean-12-en-28-oic acids (maslinic, augustic, bredemolic and 3-epi-maslinic acid) were easily accessed from one single starting material, oleanolic acid. The procedures allow the medium-to-large scale preparation of these valuable starting materials. Except for maslinic acid, the triterpenoic acids showed only a low cytotoxicity towards several human tumor cell lines.
- Sommerwerk, Sven,Heller, Lucie,Serbian, Immo,Csuk, René
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p. 8528 - 8534
(2016/02/03)
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- Synthesis of oxygenated oleanolic and ursolic acid derivatives with anti-inflammatory properties
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The scalable syntheses of four oxygenated triterpenes have been implemented to access substantial quantities of maslinic acid, 3-epi-maslinic acid, corosolic acid, and 3-epi-corosolic acid. Semi-syntheses proceed starting from the natural products oleanolic acid and ursolic acid. Proceeding over five steps, each of the four compounds can be synthesized on the gram scale. Divergent diastereoselective reductions of α-hydroxy ketones provided access to the four targeted diol containing compounds from two precursors of the oleanane or ursane lineage. These compounds were subsequently evaluated for their ability to inhibit inflammatory gene expression in a mouse model of chemically induced skin inflammation. All compounds possessed the ability to inhibit the expression of one or more inflammatory genes induced by 12-O-tetradecanoylphorbol-13 acetate in mouse skin, however, three of the compounds, corosolic acid, 3-epi-corosolic acid and maslinic acid were more effective than the others. The availability of gram quantities will allow further testing of these compounds for potential anti-inflammatory activities as well as cancer chemopreventive activity.
- Nelson, Andrew T.,Camelio, Andrew M.,Claussen, Karin R.,Cho, Jiyoon,Tremmel, Lisa,Digiovanni, John,Siegel, Dionicio
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p. 4342 - 4346
(2015/11/03)
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- Convenient and chromatography-free partial syntheses of maslinic acid and augustic acid
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A convenient and chromatography-free 4-step synthesis of analytically pure maslinic acid (1, 41.2%) from oleanolic acid has been developed. Slight variations in the final steps gave an excellent yield of isomeric augustic acid (7, 71.9%).
- Sommerwerk, Sven,Csuk, René
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p. 5156 - 5158
(2014/12/11)
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- Four new triterpenoids isolated from the resin of Garcinia hanburyi
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Four new triterpenoids, 2-O-acetyl-3-O-(4′-O-acetyl)-α-l- arabinopyranosylmaslinic acid (1), 2-O-acetyl-3-O-(3′-O-acetyl)-α-l- arabinopyranosylmaslinic acid (2), 2-O-acetyl-3-O-(3′,4′-O-diacetyl) -α-l-arabinopyranosylmaslinic acid (3), and 3-O-(3′-O-acety
- Wang, Hong-Min,Liu, Qun-Fang,Zhao, Yi-Wu,Liu, Shuang-Zhu,Chen, Zhen-Hua,Zhang, Ru-Jun,Wang, Zhen-Zhong,Xiao, Wei,Zhao, Wei-Min
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- Semi-synthesis of acylated triterpenes from olive-oil industry wastes for the development of anticancer and anti-HIV agents
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A broad set of potential bioactive conjugate compounds has been semi-synthesized through solution- and solid-phase organic procedures, coupling two natural pentacyclic triterpene acids, oleanolic (OA) and maslinic acids (MA), at the hydroxyl groups of the A-ring of the triterpene skeleton, with 10 different acyl groups. These acyl OA and MA derivatives have been tested for their anti-proliferative (against the b16f10 murine melanoma cancer cells) and antiviral (as inhibitors of the HIV-1-protease) effects. Several derivatives have shown high levels of early and total apoptosis (up to 90%). Most of the compounds that exhibited anti-proliferative effects also generated ROS, probably involving the activation of an intrinsic apoptotic route. The only four compounds that did not cause the release of ROS could be related to the participation of a probable extrinsic activation of the apoptosis mechanism. A great number of these acyl OA and MA derivatives have proved to be potent inhibitors of the HIV-1-protease, the most active inhibitors having IC 50 values between 0.31 and 15.6 μM, these values being between 4 and 186 times lower than their non-acylated precursors. The potent activities exhibited in the apoptosis-activation processes and in the inhibition of the HIV-1-protease by some OA and MA acylated derivatives imply that these compounds could be used as new, safe, and effective anticancer and/or antiviral drugs.
- Parra, Andres,Martin-Fonseca, Samuel,Rivas, Francisco,Reyes-Zurita, Fernando J.,Medina-O'Donnell, Marta,Martinez, Antonio,Garcia-Granados, Andres,Lupia?ez, Jose A.,Albericio, Fernando
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p. 278 - 301
(2014/02/14)
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- Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: Synthesis, structure-activity relationships, and X-ray crystallographic studies
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Twenty-five naturally occurring pentacyclic triterpenes, 15 of which were synthesized in this study, were biologically evaluated as inhibitors of rabbit muscle glycogen phosphorylase a (GPa). From SAR studies, the presence of a sugar moiety in triterpene saponins resulted in a markedly decreased activity (7, 18-20) or no activity (21, 22). These saponins, however, might find their value as potential natural prodrugs which are much more water-soluble than their corresponding aglycones. To elucidate the mechanism of GP inhibition, we have determined the crystal structures of the GPb-asiatic acid and GPb-maslinic acid complexes. The X-ray analysis indicates that the inhibitors bind at the allosteric activator site, where the physiological activator AMP binds. Pentacyclic triterpenes represent a promising class of multiple-target antidiabetic agents that exert hypoglycemic effects, at least in part, through GP inhibition.
- Wen, Xiaoan,Sun, Hongbin,Liu, Jun,Cheng, Keguang,Zhang, Pu,Zhang, Liying,Hao, Jia,Zhang, Luyong,Ni, Peizhou,Zographos, Spyros E.,Leonidas, Demettes D.,Alexacou, Kyra-Melinda,Gimisis, Thanasis,Hayes, Joseph M.,Oikonomakos, Nikos G.
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experimental part
p. 3540 - 3554
(2009/04/07)
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- Pentacyclic triterpenes. Part 2: Synthesis and biological evaluation of maslinic acid derivatives as glycogen phosphorylase inhibitors
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The synthesis of a series of maslinic acid derivatives is described and their effect on rabbit muscle glycogen phosphorylase a evaluated. Within this series of compounds, 15 (IC50 = 7 μM) is the most potent GPa inhibitor. SAR of the maslinic acid derivatives are discussed.
- Wen, Xiaoan,Zhang, Pu,Liu, Jun,Zhang, Luyong,Wu, Xiaoming,Ni, Peizhou,Sun, Hongbin
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p. 722 - 726
(2007/10/03)
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- Pentacyclic triterpenes. Part 1: The first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases
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The semi-synthesis, in vitro and in vivo biological evaluation of corosolic acid (1) and maslinic acid (2) are described. Compounds 1 and 2 represent a new class of inhibitors of glycogen phosphorylases. Both 1 and 2 inhibit the increase of fasted plasma glucose of diabetic mice induced by adrenaline. It is therefore proposed that naturally occurring pentacyclic triterpenes 1 and 2 might reduce blood glucose, at least in part, through inhibiting hepatic glycogen degradation.
- Wen, Xiaoan,Sun, Hongbin,Liu, Jun,Wu, Guanzhong,Zhang, Luyong,Wu, Xiaoming,Ni, Peizhou
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p. 4944 - 4948
(2007/10/03)
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- Insulin secretion potentiator
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The invention provides an early insulin secretion stimulator comprising corosolic acid, etc. The early insulin secretion stimulator of the invention is capable of rapidly inducing secretion of insulin immediately after meals without inducing secretion of insulin in the absence of blood glucose increase.
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Page/Page column 5
(2008/06/13)
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- Retrovirus protease inhibitors
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A compound composition and method of treating a retrovirus infection are disclosed. In particular, isolated triterpenes have been shown to have significant inhibitory activity against HIV-1.
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- TRITERPENE SAPONOINS FROM ASTER YUNNANENSIS
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Four new triterpene saponins, asteryunnanosides A, B, C and D, have been isolated from Aster yunnanensis and their structures deduced as 2α,3β,23-trihydroxyolean-12-en-28-oic acid-28-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside, 2α,3β,23-trihydroxyolean-12-en-28-oic acid-28-O-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside, 2α,3β-dihydroxyolean-12-en-28-oic acid-28-O-α-L-rhamnopyranoside-(1->2)-β-D-glucopyranoside and 2α,3β-dihydroxyolean-12-en-28-oic acid-28-O-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside, respectively, by means of spectral and chemical data. - Key words: Aster yunnanesis; Compositae; triterpene saponins; asteryunnanosides A, B, C, D; arjunolic acid; maslinic acid.
- Shao, Yu,Zhou, Bing-Nan,Lin, Long-Ze,Cordell, Geoffrey A.
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p. 1487 - 1492
(2007/10/02)
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- 3-acetylmaslinic acid from the root bark of Terminalia alata
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A new triterpene acid, 3-acetylmaslinic acid, has been isolated from the root bark of Terminalia alata together with oleanolic acid, arjunic acid, arjunolic acid and arjunetin.
- Anjaneyulu,Reddy, A.V.Raghava,Mallavarapu, Gopal R.,Chandrasekhara
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p. 2670 - 2671
(2007/10/02)
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- TRITERPENOID SAPOGENOLS FROM THE LEAVES OF CAREYA ARBOREA: STRUCTURE OF CAREYAGENOLIDE
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The acid hydrolysate of the ethanol extract of Careya arborea leaves afforded a new triterpenoid lactone designated careyagenolide along with maslinic acid and 2α-hydroxy ursolic acid.The structure of careyagenolide has been established as 2α,3β-dihydroxytaraxastan-28,20β-olide by a variety of spectroscopic evidence, chemical transformations and correlation with ψ-taraxasterol.Key Word Index - Careya arborea; Lecythidaceae; careyagenolide; maslinic acid; 2α-hydroxy ursolic acid.
- Das, Manik C.,Mahato, Shashi B.
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p. 2069 - 2074
(2007/10/02)
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- A Simple Method for Hydrolysis of Hindered Esters: Hydrolysis of Methyl Oleanolate, Crategolate, Ursolate & Podocarpate
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Lithium and boiling ethylenediamine have been successfully used for the facile hydrolysis of hindered esters such as methyl oleanolate, crategolate, ursolate and podocarpate.
- Sengupta, Pasupati,Sen, Manju,Das, Saktipada
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p. 721 - 722
(2007/10/02)
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