Hydroxylated furanoditerpenoids from pupal cases produced by the bruchid beetle Sulcobruchus sauteri inside the seeds of Caesalpinia decapetala. (December 2018)

• Record Type: Journal Article
• Authors: Akihara, Yui; Kamikawa, Sayuri; Harauchi, Yui; Ohta, Emi; Nehira, Tatsuo; Ômura, Hisashi; Ohta, Shinji
• Is Part Of: Phytochemistry. Volume 156(2018)
• Page Start: 151
• Page End: 158
• Publication Date: 2018-12
• Subjects: Caesalpinia decapetala -- Leguminosae -- Bruchid seed beetle -- Sulcobruchus sauteri -- Cassane diterpenoid -- Detoxification; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2018.09.007
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Seven undescribed hydroxylated cassane-type furanoditerpenoids were isolated from pupal cases formed from the secretion/excretion of the larvae of the wild bruchid seed beetle Sulcobruchus sauteri in infested Caesalpinia decapetala seeds, and their structures were elucidated by interpreting their spectra. The hydroxylated furanoditerpenoids found in the pupal cases were not present in the seeds of the host plant. Caesalacetal and caesaljapin obtained from the intact seeds exhibited larvicidal activity against the larvae of Aedes albopictus, while the hydroxylated furanoditerpenoids isolated from the pupal cases were inactive. The larvae of S. sauteri are proposed to detoxify larvicidal diterpenoids that occur in the seeds of the host plant by regiospecific hydroxylation. Graphical abstract: Seven furanoditerpenoids were isolated from the pupal cases produced by Sulcobruchus sauteri inside the seeds of Caesalpinia decapetala and their structures were determined from spectroscopic data. Image 1 Highlights: Seven furanoditerpenoids were isolated from the bruchid pupal case inside seed. Their structures were elucidated based on the spectroscopic data. The absolute configurations were determined via TDDFT calculations of the ECD spectra. Possible bioconversion pathways of furanoditerpenoids by bruchids were proposed. The ability of the bruchid to hydroxylate diterpenoids may relate to its host-specificity.