Cytotoxic C(35) terpenoid cryptotrione from the bark of Cryptomeria japonica

Cheng-Chi Chen; Jyh-Horng Wu; Ning-Sun Yang; Jang-Yang Chang; Ching-Chuan Kuo; Sheng-Yang Wang; Yueh-Hsiung Kuo

doi:10.1021/ol1009027

Cytotoxic C(35) terpenoid cryptotrione from the bark of Cryptomeria japonica

Org Lett. 2010 Jun 18;12(12):2786-9. doi: 10.1021/ol1009027.

Authors

Cheng-Chi Chen¹, Jyh-Horng Wu, Ning-Sun Yang, Jang-Yang Chang, Ching-Chuan Kuo, Sheng-Yang Wang, Yueh-Hsiung Kuo

Affiliation

¹ Department of Chemistry, National Taiwan University, Taipei, Taiwan 106, ROC.

PMID: 20481455
DOI: 10.1021/ol1009027

Abstract

A novel C(35)-terpene, designated as cryptotrione (1), with an unprecedented skeleton possessing an abietane diterpene with a unique bicyclic sesquiterpene, is identified from the bark of Cryptomeria japonica. The carbon skeleton of 1 represents a new structural entity, and this is an intriguing addition to the structurally diverse diterpene-sesquiterpene class. A unique biosynthetic pathway is proposed to support the production of this phytocompound. Notably, 1 exhibits anticancer activity with an IC(50) value of 6.44 +/- 2.23 microM.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification*
Antineoplastic Agents / pharmacology*
Cryptomeria / chemistry*
Drug Screening Assays, Antitumor
Etoposide / pharmacology
Humans
Inhibitory Concentration 50
KB Cells
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Bark / chemistry
Plants, Medicinal / chemistry*
Taiwan
Terpenes / chemistry
Terpenes / isolation & purification*
Terpenes / pharmacology*

Substances

Antineoplastic Agents
Terpenes
cryptotrione
Etoposide