Antifeedant Activity of Some Pentacyclic Triterpene Acids and Their Fatty Acid Ester Analogues

Abstract

The 3-O-fatty acid ester derivatives (C(12)-C(18)) of two pentacyclic triterpenic acids, ursolic acid and oleanolic acid, were synthesized under mild esterification conditions in excellent yields (80-85%) and screened for their antifeedant activity, together with the parent acids, against the agricultural pest tobacco caterpillar larvae (Spodoptera litura F) in a no-choice laboratory study. The Urs-12-ene-28-carboxy-3beta-octadecanoate and olean-12-ene-28-carboxy-3beta-hexadecanoate were found to exhibit exceptionally potent antifeedant activities at 50 microg/cm(2) concentration, even after 48 h.

Chemical constituents from Aspidosperma illustre (Apocynaceae)

“…The hexane and MeOH extracts of stem bark and leaves of A. illustre were subjected to a classical chromatographic methods to yield the a new oleanane-type triterpene, olean-12-ene-11a-methoxy-3β-acetate (10), in addition to known, β-amyrin (3), 4 lupeol (4), 4 β-amyrin acetate (5), 4 lupeol acetate (6), 4 olean-12-ene-28-hydroxy-3β-tetradecanoate (7), 4 olean-12-ene-28-carboxy-3β-hexadecanoate (8), 5,6 ursolic acid (9), 4 β-yoimbine (1) The oxidation at CH-11 of 10 is adequate to introduce significant modification in fragmentation of this pentacyclic triterpene containing double bond between the carbon atoms CH-12 e C-13 in the mass spectrometer, revealing the absence of peaks produce by reaction Retro-DielsAlder (RDA), as observed in other triterpenes with such characteristics. 13,14 Confirmation of structure 10 was done by comparison with authentic sample of derivative monoacetate of triterpene 11-a-methoxy-β-amyrin isolated from Myroxylon balsamum (Fabaceae).…”

“…A partir de Aspidosperma illustre, foi obtido como produto natural um novo triterpeno da série oleanano, o olean-12-en-11a-metóxi-3β-acetato (10), além dos triterpenos β-amyrina (3), lupeol (4), acetato de β-amyrina (5), acetato de lupeol (6), olean-12-en-28-hidróxi-3β-tetradecanoato (7), olean-12-en-28-carboxi-3β-hexadecanoato (8), ácido ursólico (9) e dois alcalóides indólicos monoterpênicos, β-ioimbina (1) e 1,2-desidroaspidospermidina (2). As substâncias isoladas foram identificadas através de métodos espectroscópicos, principalmente uni (RMN 1 H, 13 C, APT) e bidimensionais ( A new natural product oleanane-type triterpene, olean-12-ene-11a-methoxy-3β-acetate (10) was isolated from Aspidosperma illustre, together with β-amyrin (3), lupeol (4), β-amyrin acetate (5), lupeol acetate (6), olean-12-ene-28-hydroxy-3β-tetradecanoate (7), olean-12-ene-28-carboxy-3β-hexadecanoate (8), ursolic acid (9) triterpenes, and two monoterpenic indole alkaloids, β-yoimbine (1) and 1,2-dehydroaspidospermidine (2).…”

Medicinal chemistry and pharmacology of genus Tripterygium (Celastraceae)

“…It also showed strong antimolting activity against the last of these. Oleanolic acid (83) had some antifeedant activity against Spodoptera litura (Mallavadhani et al, 2003), and 3-acetoxy-oleanolic acid (84) showed antifeedant activity against Leptinotarsa decemlineata (the Colorado potato beetle) (Hua et al, 1991). (Fig.…”

Clinically useful anticancer, antitumor, and antiwrinkle agent, ursolic acid and related derivatives as medicinally important natural product

“…The Urs-12-ene-28-carboxy-3β-octadecanoate and olean-12-ene-28-carboxy-3β-hexadecanoate were found to exhibit exceptionally potent antifeedant activities at 50 µg/cm 2 concentration (Scheme 13). 334 9.10.Anti-AIDS agents. Anti-HIV activity of ursolic acid and structurally related triterpenoids Oxidation of ursolic acid (1) yielded a 3-oxo-derivative (89), which was more toxic against uninfected H9 cells than its parent compound, but inhibited HIV-1 replication, with an improved EC 50 value of 0.11 g/mL.…”