Dhilirolides E鈥揘, Meroterpenoids Produced in Culture by the Fungus Penicillium purpurogenum Collected in Sri Lanka: Structure Elucidation, Stable Isotope Feeding Studies, and Insecticidal Activ
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- 作者：Ryan M. Centko ; David. E. Williams ; Brian O. Patrick ; Yasmin Akhtar ; Miguel Angel Garcia Chavez ; Yan Alexander Wang ; Murray B. Isman ; E. Dilip de Silva ; Raymond J. Andersen
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：April 18, 2014
- 年：2014
- 卷：79
- 期：8
- 页码：3327-3335
- 全文大小：442K
- 年卷期：v.79,no.8(April 18, 2014)
- ISSN：1520-6904
文摘
Extracts of laboratory cultures of the fungus Penicilium purpurogenum obtained from rotting fruit of the tree Averrhoa bilimbi growing in Sri Lanka have yielded 10 new meroterpenoids, dhilirolides E鈥揘 (5鈥?b>14). The structures of the new dhilirolides have been elucidated by analysis of spectroscopic data and a single-crystal X-ray diffraction analysis of dhilirolide L (12). Dhilirolides A鈥揘 (1鈥?b>14) represent the four unprecedented and rearranged dhilirane, isodhilirane, 14,15-dinordhilirane, and 23,24-dinorisodhilirane meroterpenoid carbon skeletons. Stable isotope feeding studies have confirmed the meroterpenoid biogenetic origin of the dhilirolides and provided support for a proposed genesis of the new carbon skeletons. Dhilirolide L (12) showed significant feeding inhibition and sublethal developmental disruption in the cabbage looper Trichoplusia ni, an important agricultural pest, at low concentrations.