Aromadendrane and cyclofarnesane sesquiterpenoids from cultures of the basidiomycete Inonotus sp. BCC 23706

Masahiko Isaka; Arunrat Yangchum; Sumalee Supothina; Thitiya Boonpratuang; Rattaket Choeyklin; Palangpon Kongsaeree; Samran Prabpai

doi:10.1016/j.phytochem.2015.08.011

Aromadendrane and cyclofarnesane sesquiterpenoids from cultures of the basidiomycete Inonotus sp. BCC 23706

Phytochemistry. 2015 Oct:118:94-101. doi: 10.1016/j.phytochem.2015.08.011. Epub 2015 Aug 22.

Authors

Masahiko Isaka¹, Arunrat Yangchum², Sumalee Supothina², Thitiya Boonpratuang², Rattaket Choeyklin³, Palangpon Kongsaeree⁴, Samran Prabpai⁴

Affiliations

¹ National Center for Genetic Engineering and Biotechnology (BIOTEC), 113 Thailand Science Park, Phaholyothin Road, Klong Luang, Pathumthani 12120, Thailand. Electronic address: isaka@biotec.or.th.
² National Center for Genetic Engineering and Biotechnology (BIOTEC), 113 Thailand Science Park, Phaholyothin Road, Klong Luang, Pathumthani 12120, Thailand.
³ Biodiversity-Based Economy Development Office, The Government Complex, Chaeng Wattana Road, Bangkok 10210, Thailand.
⁴ Department of Chemistry, Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand; Center for Excellence in Protein Structure and Function, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand.

PMID: 26307664
DOI: 10.1016/j.phytochem.2015.08.011

Abstract

Twelve aromadendrane sesquiterpenoids, inonotins A-L, and a previously unknown cyclofarnesane, i.e., inonofarnesane, together with two known compounds, were isolated from cultures of the wood-rotting basidiomycete Inonotus sp. BCC 23706. Inonotin I is identical to a previously reported compound with an incorrect structure. Structures of the compounds were elucidated by spectroscopic analysis and X-ray crystallography. The absolute configurations of inonotin D and inonofarnesane were determined by application of the modified Mosher's method.

Keywords: Aromadendrane; Basidiomycete; Cyclofarnesane; Inonotus.

Publication types

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

MeSH terms

Basidiomycota / chemistry*
Crystallography, X-Ray
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification*
Sesquiterpenes, Guaiane

Substances

Sesquiterpenes
Sesquiterpenes, Guaiane
aromadendrane