Insect Antifeedants from Croton jatrophoides:  Structures of Zumketol, Zumsenin, and Zumsenol

Abstract

Three new A-seco limonoids, zumketol (1), zumsenin (2), and zumsenol (3), were isolated from a methanol extract of Croton jatrophoides by bioassay-guided fractionation, and their structures were determined by NMR analysis. The alpha-ketol 1 may be biosynthesized via the intramolecular acyloin condensation of a dicarboxylate intermediate.

Effect of seed extracts of Withania somnifera, Croton tiglium and Hygrophila auriculata on behavior and physiology of Odontotermes obesus (Isoptera, Termitidae)

“…An insect antifeedant was isolated from Croton jatrophoides (Nihei et al 2005). There is no record of the presence of such compounds in C. tiglium used in the present study, however, seed extract of this plant showed the lowest LT 50 at 50 and 100% concentrations, followed by W. somnifera.…”

A Review of Phytochemistry and Pharmacological Properties of Threatened Croton Species Used as Herbal Medicines in East Africa

“…These five Croton species have high pharmaceutical value due to alkaloids [14,15], diterpenoids [14,16], esters [14,15], furanoditerpenoids [23,24], limonoids [25][26][27][28][29], methylcyclohexane [14,15,30], steroids [15] and triterpenoids [14,15] that have been isolated from bark, leaves and roots. Chhabra et al…”

“…Ndunda [14] and Ndunda et al [15] isolated methylcyclohexane, pentacyclic triterpenoid, ester, alkaloid and steroid compounds, namely crotepoxide, dideacetylcrotepoxide, monodeacetylcrotepoxide, αsenepoxide, β-senepoxide, (+)-(2S, 3R)-diacetoxy-1benzoyloxymethylenecyclohex-4, 6-diene, acetyl aleuritolic, alienusolin, benzyl benzoate, crotonimide C, julocrotine and 24-ethylcholesta-4,22-dien-3-one24ethylcholesta-4,22-dien-3-one24-ethylcholesta-4,22dien-3-one from leaves and roots of C. alienus (Table 3). Limonoids, namely dumsin, zumsin, zumketol, zumsenin, zumsenol, dumnin, dumsenin, musidunin and musiduol were isolated from root bark of C. jatrophoides [25][26][27][28][29] (Table 3). Mbwambo et al [23] and Magadula et al [24]…”

“…Nihei et al [26][27][28][29] evaluated insect antifeedant activities of compounds dumnin, dumsenin, musidunin, musiduol, zumketol and zumsinisolated from C. jatrophoides using leaf disk assay and second-instar larvae of Pectinophora gossypiella and Spodoptera frugiperda as test organisms. The two compounds showed antifeedant activities with 50% protective concentration (PC 50 ), PC 90 and PC 95 values ranging from 0.5 µg/mL to 36 µg/mL against the larvae of Pectinophora gossypiella and Spodoptera frugiperda [26][27][28][29]. Similarly, Kinyoda et al [36] evaluated antifungal activities of hexane, ethyl acetate and methanol root, bark and leaf extracts of C. jatrophoides against Fusarium oxysporum f. sp.…”

New Furanoditerpenoids fromCroton jatrophoides

“…In addition chemical constituents with interesting biological activities have been obtained from this genus, such as insect antifeedant, antitumor and antifungal agents, and compounds active against digestive disorders, inflammation, fever, and malaria [3]. From Croton jatrophoides, a series of limonoids with insect antifeedant properties has been isolated [4], [5], [6], [7]. As part of our continuing studies on Tanzanian plants with medicinal interest [8], [9], [10], we examined the extract of roots of C. jatrophoides.…”