Synthesis and evaluation of potential complement inhibitory semisynthetic analogs of oleanolic acid

Assefa, Haregewein; Nimrod, Alison C.; Walker, Larry; Sindelar, Robert D.

doi:10.1016/s0960-894x(99)00314-5

Cited by 40 publications

(31 citation statements)

References 22 publications

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“…27) In addition, the ceanothic acid derivatives, colubrinic acid (1) and zizyberenalic acid (11), were also inactive in this assay system, However, 2-hydroxyl-3-coumaroyl-oleanolic acid (5, 6) possessed significant anticomplement activity compared with oleanolic acid (8). Accordingly, oleanolic acid (8) and its coumaroyl analogs (5, 6) might be good candidates as compounds for improving the unwanted and excessive activation of the complement system.…”

Section: Resultsmentioning

confidence: 94%

Anti-complementary Activity of Triterpenoides from Fruits of Zizyphus jujuba

Lee

Park

Lee

et al. 2004

Biological & Pharmaceutical Bulletin

101

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In order to determine on the anti-complement activity of triterpenes, following eleven triterpenoides were isolated from the fruits of the Zizyphus jujuba MILL: ceanothane-type triterpenes: colubrinic acid (1), zizyberenalic acid (11); lupane-type triterpenes: alphitolic acid (2), 3-O-cis-p-coumaroyl alphitolic acid (3), 3-O-trans-pcoumaroyl alphitolic acid (4), betulinic acid (7), betulonic acid (9); and oleanane-type triterpenes: 3-O-cis-pcoumaroyl maslinic acid (5), 3-O-trans-p-coumaroyl maslinic acid (6), oleanolic acid (8), oleanonic acid (10). These compounds were examined for their anti-complement activity against the classical pathway of the complement system. Among them, compounds 5, 6, and 8 exhibited significant anti-complement activity with IC 50 values of 101.4, 143.9, and 163.4 m mM, respectively, whereas the ceanothane-type and the lupane-type triterpenes were inactive. This suggests that the oleanane-structure plays an important role in inhibiting the hemolytic activity of human serum against erythrocytes.

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Section: Resultsmentioning

confidence: 94%

Anti-complementary Activity of Triterpenoides from Fruits of Zizyphus jujuba

Lee

Park

Lee

et al. 2004

Biological & Pharmaceutical Bulletin

101

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“…Oleanolic acid (83) inhibited the classic pathway of complement activation in vitro (Kapil and Sharma, 1994;Assefa et al, 1999) but did not inhibit the alternate pathway (Kapil and Sharma, 1994). The inhibition of the classic pathway by 83 was mainly due to inhibition of C 3 -convertase (EC 3.4.21.43), a serine protease in the pathway (Kapil and Sharma, 1994).…”

Section: Proinflammatory Enzymesmentioning

confidence: 99%

Medicinal chemistry and pharmacology of genus Tripterygium (Celastraceae)

et al. 2007

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Plants in the genus Tripterygium, such as Tripterygium wilfordii Hook. f., have a long history of use in traditional Chinese medicine. In recent years there has been considerable interest in the use of Tripterygium extracts and of the main bioactive constituent, the diterpene triepoxide triptolide (1), to treat a variety of autoimmune and inflammation-related conditions. The main mode of action of the Tripterygium extracts and triptolide (1) is the inhibition of expression of proinflammatory genes such as those for interleukin-2 (IL-2), inducible nitric oxide synthase (iNOS), tumor necrosis factor-α (TNF-α), cyclooxygenase-2 (COX-2) and interferon-gamma (IFN-γ). The efficacy and safety of certain types of Tripterygium extracts were confirmed in human clinical trials in the US and abroad. Over 300 compounds have been identified in the genus Tripterygium, and many of these have been evaluated for biological activity. The overall activity of the extract is based on the interaction between its components. Therefore, the safety and efficacy of the extract cannot be fully mimicked by any individual constituent. This review discusses the biochemical composition and biological and pharmacological activities of Tripterygium extracts, and their main bioactive components.

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“…Because of the relatively weak biological activities of the natural triterpenoids, new analogs of these molecules were synthesized in an attempt to identify more potent agents (21)(22)(23). One of these analogs is methyl-2-cyano-3,12-dioxooleana-1,9-dien-28-oate (CDDO-Me), which was found to induce apoptosis in human lung cancer cells and other types of cancer cells (24 -26).…”

Section: Introductionmentioning

confidence: 99%