Biotransformation of (+)- and (−)-fenchone by cultured cells of Eucalyptus perriniana

Yutaka Orihara, Tsutomu Furuya

doi:10.1016/s0031-9422(00)97011-0

Biotransformation of (+)- and (−)-fenchone by cultured cells of Eucalyptus perriniana

DOI Web Site Web Site 被引用文献2件

書誌事項

公開日: 1994-05

権利情報

https://www.elsevier.com/tdm/userlicense/1.0/

DOI

10.1016/s0031-9422(00)97011-0

公開者: Elsevier BV

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説明

Abstract Six new biotransformation products, (1 R ,4 R ,5 S )-5-hydroxyfenchan-2-one 5- O -β- d -glucopyranoside and 5- O -β-gentiobioside, (1 R ,4 S ,6 R )-6-hydroxyfenchan-2-one 6- O -β- d -glucopyranoside and 6- O -β-gentiobioside, and (1 S ,4 S ,7 S )-7-hydroxyfenchan-2-one 7- O -β- d -glucopyranoside and 7- O -β-gentiobioside, were isolated from cell suspension culture of Eucalyptus perriniana following administration of (+)-fenchone. On the other hand, three new products, (1 S ,4 S ,5 R )-5-hydroxyfenchan-2-one 5- O -β- d -glucopyranoside, (1 S ,4 R ,6 S )-6-hydroxyfenchan-2-one 6- O -β- d -glucopyranoside and 6- O -β-gentiobioside, were isolated from the culture administered (−)-fenchone. Regio- and stereoselectivity of the hydroxylation of bicyclic monoterpenes are also discussed.