title: Kujigamberol, a new dinorlabdane diterpenoid isolated from 85million years old Kuji amber using a biotechnological assay.
abstract: A new compound, 15,20-dinor-5,7,9-labdatriene-18-ol (1), named kujigamberol, was isolated from amber, fossilized tree resin from the Kuji area in Japan, has been dated as being 85 million years old (late Cretaceous). Kujigamberol was identified using the hypersensitive mutant yeast (zds1∆ erg3∆ pdr1∆ pdr3∆) with respect to Ca(2+)-signal transduction. The structure was elucidated on the basis of spectroscopic analysis including 1D NMR, 2D NMR and HR-EI-MS. It was different from known diterpenoids with a similar activity isolated from Baltic amber (agathic acid 15-monomethyl ester (2), dehydroabietic acid (3) and pimaric acid (4)). Kujigamberol showed glycogen synthase kinase-3β (GSK-3β) inhibition activity involving the growth restored activity against the mutant yeast and was cytotoxic to HL60 cells (IC(50)=19.6 μM).
authors.affiliation: Graduate School of Agriculture, Iwate University, Morioka, Japan. kimurak@iwate-u.ac.jp
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Kimura
authors.forename: Yuki
authors.initials: Y
authors.lastname: Minamikawa
authors.forename: Yukiko
authors.initials: Y
authors.lastname: Ogasawara
authors.forename: Jun
authors.initials: J
authors.lastname: Yoshida
authors.forename: Kei-ichi
authors.initials: K
authors.lastname: Saitoh
authors.forename: Hisao
authors.initials: H
authors.lastname: Shinden
authors.forename: Yue Qi
authors.initials: YQ
authors.lastname: Ye
authors.forename: Shunya
authors.initials: S
authors.lastname: Takahashi
authors.forename: Tokichi
authors.initials: T
authors.lastname: Miyakawa
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Koshino
mesh_terms: D018647:Amber / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology / Q000627:therapeutic use; D002118:Calcium / Q000378:metabolism; D004224:Diterpenes / Q000302:isolation & purification* / Q000494:pharmacology / Q000627:therapeutic use; D004791:Enzyme Inhibitors / Q000302:isolation & purification* / Q000494:pharmacology / Q000627:therapeutic use; D005580:Fossils; D038362:Glycogen Synthase Kinase 3 / Q000037:antagonists & inhibitors; D000071679:Glycogen Synthase Kinase 3 beta; D018922:HL-60 Cells; D006801:Humans; D007564:Japan; D015394:Molecular Structure; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D015398:Signal Transduction; D015003:Yeasts
chemical_list: C575153:15,20-dinor-5,7,9-labdatriene-18-ol; D018647:Amber; D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D004791:Enzyme Inhibitors; D010936:Plant Extracts; C000605506:GSK3B protein, human; D000071679:Glycogen Synthase Kinase 3 beta; D038362:Glycogen Synthase Kinase 3; D002118:Calcium