Synthesis and structure–activity relationship of kujigamberol B, a dinorlabdane diterpenoid isolated from an ancient Kuji amber-Reference-Cited by-同舟云学术

Synthesis and structure–activity relationship of kujigamberol B, a dinorlabdane diterpenoid isolated from an ancient Kuji amber

Published:2023-03-10 Issue:6 Volume:87 Page:575-583
ISSN:1347-6947
Container-title:Bioscience, Biotechnology, and Biochemistry
language:en
Short-container-title:

Author:

Kishibata Sakura¹,Tanaka Kurumi²,Saito Tatsuo³^ORCID,Kimura Ken-ichi²,Yajima Arata³^ORCID

Affiliation:

1. Graduate School of Life Sciences, Tokyo University of Agriculture , 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo, Japan

2. Chemical Biology Laboratory, Graduate School of Arts and Sciences, Iwate University , Morioka, Japan

3. Department of Chemistry for Life Sciences and Agriculture, Faculty of Life Sciences, Tokyo University of Agriculture , 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo, Japan

Abstract

ABSTRACT The versatile methodology was developed for synthesizing kujigamberol B, a dinorlabdane diterpenoid isolated from the methanol extract of Kuji amber. A highly efficient intramolecular cyclization is followed by a Sonogashira-coupling reaction during the total synthesis. The synthesized compounds were evaluated for the growth-restoring activity against the mutant yeast (zds1Δ erg3Δ pdr1Δ pdr3Δ) and for the degranulation of RBL-2H3 cells. We found that in both activities, primary alcohol and secondary alcohol analogs are as active as kujigamberol B.

Funder

Tokyo University of Agriculture

Hiroshima University

Publisher

Oxford University Press (OUP)

Subject

Organic Chemistry,Molecular Biology,Applied Microbiology and Biotechnology,General Medicine,Biochemistry,Analytical Chemistry,Biotechnology

Link

https://academic.oup.com/bbb/advance-article-pdf/doi/10.1093/bbb/zbad027/49686692/zbad027.pdf

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