Crotocascarins I–K: Crotofolane-Type Diterpenoids, Crotocascarin γ, Isocrotofolane Glucoside and Phenolic Glycoside from the Leaves of Croton cascarilloides

Susumu Kawakami; Katsuyoshi Matsunami; Hideaki Otsuka; Masanori Inagaki; Yoshio Takeda; Masatoshi Kawahata; Kentaro Yamaguchi

doi:10.1248/cpb.c15-00635

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Crotocascarins I–K: Crotofolane-Type Diterpenoids, Crotocascarin γ, Isocrotofolane Glucoside and Phenolic Glycoside from the Leaves of Croton cascarilloides

Susumu Kawakami, Katsuyoshi Matsunami, Hideaki Otsuka , Masanori Inagaki, Yoshio Takeda, Masatoshi Kawahata, Kentaro Yamaguchi

Author information

Susumu Kawakami
Department of Natural Products Chemistry, Faculty of Pharmacy, Yasuda Women’s University
Katsuyoshi Matsunami
Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University
Hideaki Otsuka Corresponding author
Department of Natural Products Chemistry, Faculty of Pharmacy, Yasuda Women’s University
Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University
Masanori Inagaki
Department of Natural Products Chemistry, Faculty of Pharmacy, Yasuda Women’s University
Yoshio Takeda
Department of Natural Products Chemistry, Faculty of Pharmacy, Yasuda Women’s University
Masatoshi Kawahata
Department of Analytical Chemistry, Faculty of Pharmaceutical Sciences, Tokushima Bunri University Kagawa Campus
Kentaro Yamaguchi
Department of Analytical Chemistry, Faculty of Pharmaceutical Sciences, Tokushima Bunri University Kagawa Campus

Keywords: Croton cascarilloides, Euphorbiaceae, crotocascarin, crotofolane, nor-crotofolane, isocrotofolane

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2015 Volume 63 Issue 12 Pages 1047-1054

DOI https://doi.org/10.1248/cpb.c15-00635

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Abstract

From the 1-BuOH-soluble fraction of a methanol (MeOH) extract of the leaves of Croton cascarilloides, crotofolanes: crotocascarins I–K, nor-crotofolane: crotocascarin γ, isocrotofolane glucoside and phenolic glycoside were isolated by a combination of various separation techniques. Their structures were elucidated mainly from the NMR spectroscopic evidence. The structure of crotocascarin K was first elucidated by spectroscopic analysis and then was confirmed by X-ray crystallographic analysis. Its absolute structure was finally determined by the modified Mosher’s method. Isocrotofolane glucoside was found to possess a new skeleton, however, its absolute structure remains to be determined.

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