Tobacco Caterpillar Antifeedent from the Gotti Stem Wood Triterpene Betulinic Acid

Abstract

Betulinic acid (I), a pentacyclic triterpene, on derivatization gives six compounds: 3β-hydroxylup-20(29)-en-28 oic acid methyl ester (II), 3β-acetoxylup-20(29)-en-28-oic acid (III), 3β-allyloxylup-20(29)-en-28-oic acid (IV), 3β-p-methylcinnamatoxylup-20(29)-en-28-oic acid (V), 3β-p-methoxycinnamatoxylup-20(29)-en-28-oic acid (VI), and 3β-tri-O-methylgallotoxylup-20(29)-en-28-oic acid (VII). Their antifeedent activity against the agricultural pest tobacco caterpillar larvae (Spodoptera litura F) in a no-choice laboratory study showed the active compounds are V, VI, and VII. Keywords: Antifeedent; betulinic acid derivatives; tobacco caterpillar; Spodoptera litura (F)

Isolation, characterization and biological activity of betulinic acid and ursolic acid from Vitex negundo L.

“…Compound 1 also showed relatively strong antifeedant activity at all dosages but compounds 2 and 5 showed relatively low antifeedant activity. Similar results were obtained with studies on betulinic acid and their derivatives against larvae of Spodoptera litura (Jagadeesh et al, 1998), and with betulin as an antifeedant against the Colorado Potato Beetle (Huang et al, 1995).…”

Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection

“…[10][11][12] Other known sources of betulinic acid include Ziziphus spp. (Rhamnaceae), [13][14][15] Syzygium spp. (Myrtaceae), 16,17 Diospyros spp.…”

“…26,110 In addition, betulinic acid has been shown to exert inhibitory activity against cyclic AMP-dependent protein kinase, 111 sulfonylureas, 29 and stromelysin and collagenase. 28 Betulinic acid and derivatives do not exhibit tobacco larvae antifeedant, 15 spermicidal, 112 or icthyotoxic 19 activities. Because of conflicting data, it is unclear whether betulinic acid possesses germination and root growth inhibitory effects against plants.…”

Triterpene-based plant defenses

“…Thus, b-amyrin palmitate, isolated from Santalum album, acts as an insect growth inhibitor and exhibits chemosterilant properties (Shankaranarayana et al 1980). Betulin derivatives are effective agents against bollworm larvae (Heliothis zea; Lugemwa et al 1990) and Colorado potato beetle (Leptinotarsa decemlineata; Huang et al 1995), while betulinic acid derivatives are active against S. litura (Jagadeesh et al 1998). Oleanolic acid derivatives act as a feeding deterrent against L. decemlineata (Kubo et al 1990;Hua et al 1991), while ursolic and oleanolic acids and their fatty acid ester analogues, have been screened for their activity against S. litura (Mallavadhani et al 2003).…”