Hitoyol A and B, Two Norsesquiterpenoids from the Basidiomycete Coprinopsis cinerea

Junnosuke Otaka; Daisuke Hashizume; Yui Masumoto; Atsuya Muranaka; Masanobu Uchiyama; Hiroyuki Koshino; Yushi Futamura; Hiroyuki Osada

doi:10.1021/acs.orglett.7b01784

Hitoyol A and B, Two Norsesquiterpenoids from the Basidiomycete Coprinopsis cinerea

Junnosuke Otaka, Daisuke Hashizume, Yui Masumoto, Atsuya Muranaka, Masanobu Uchiyama, Hiroyuki Koshino, Yushi Futamura, Hiroyuki Osada^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

Hitoyol A (1), an unprecedented norsesquiterpenoid with an exo-tricyclo[5.2.1.0^2,6]decane skeleton, was isolated from the culture broth of Basidiomycete Coprinopsis cinerea along with a novel skeletal hitoyol B (2) containing 4-cyclopentene-1,3-dione. Their structures and absolute configurations were analyzed by single-crystal X-ray diffraction and electronic circular dichroism spectroscopic methods. Compound 1 is possibly biosynthesized through decarboxylation-induced cyclization of lagopodin B, a known cuparene-type sesquiterpenoid. Compound 2 showed weak antimalarial activity with an IC₅₀ of 59 μM.

Original language	English
Pages (from-to)	4030-4033
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.7b01784
Publication status	Published - 2017 Aug 4
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.7b01784

Cite this

@article{5df36a2a536e4cc98c4011ac9ac5319a,

title = "Hitoyol A and B, Two Norsesquiterpenoids from the Basidiomycete Coprinopsis cinerea",

abstract = "Hitoyol A (1), an unprecedented norsesquiterpenoid with an exo-tricyclo[5.2.1.02,6]decane skeleton, was isolated from the culture broth of Basidiomycete Coprinopsis cinerea along with a novel skeletal hitoyol B (2) containing 4-cyclopentene-1,3-dione. Their structures and absolute configurations were analyzed by single-crystal X-ray diffraction and electronic circular dichroism spectroscopic methods. Compound 1 is possibly biosynthesized through decarboxylation-induced cyclization of lagopodin B, a known cuparene-type sesquiterpenoid. Compound 2 showed weak antimalarial activity with an IC50 of 59 μM.",

author = "Junnosuke Otaka and Daisuke Hashizume and Yui Masumoto and Atsuya Muranaka and Masanobu Uchiyama and Hiroyuki Koshino and Yushi Futamura and Hiroyuki Osada",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = aug,

day = "4",

doi = "10.1021/acs.orglett.7b01784",

language = "English",

volume = "19",

pages = "4030--4033",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - Hitoyol A and B, Two Norsesquiterpenoids from the Basidiomycete Coprinopsis cinerea

AU - Otaka, Junnosuke

AU - Hashizume, Daisuke

AU - Masumoto, Yui

AU - Muranaka, Atsuya

AU - Uchiyama, Masanobu

AU - Koshino, Hiroyuki

AU - Futamura, Yushi

AU - Osada, Hiroyuki

PY - 2017/8/4

Y1 - 2017/8/4

N2 - Hitoyol A (1), an unprecedented norsesquiterpenoid with an exo-tricyclo[5.2.1.02,6]decane skeleton, was isolated from the culture broth of Basidiomycete Coprinopsis cinerea along with a novel skeletal hitoyol B (2) containing 4-cyclopentene-1,3-dione. Their structures and absolute configurations were analyzed by single-crystal X-ray diffraction and electronic circular dichroism spectroscopic methods. Compound 1 is possibly biosynthesized through decarboxylation-induced cyclization of lagopodin B, a known cuparene-type sesquiterpenoid. Compound 2 showed weak antimalarial activity with an IC50 of 59 μM.

AB - Hitoyol A (1), an unprecedented norsesquiterpenoid with an exo-tricyclo[5.2.1.02,6]decane skeleton, was isolated from the culture broth of Basidiomycete Coprinopsis cinerea along with a novel skeletal hitoyol B (2) containing 4-cyclopentene-1,3-dione. Their structures and absolute configurations were analyzed by single-crystal X-ray diffraction and electronic circular dichroism spectroscopic methods. Compound 1 is possibly biosynthesized through decarboxylation-induced cyclization of lagopodin B, a known cuparene-type sesquiterpenoid. Compound 2 showed weak antimalarial activity with an IC50 of 59 μM.

UR - http://www.scopus.com/inward/record.url?scp=85027033092&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85027033092&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.7b01784

DO - 10.1021/acs.orglett.7b01784

M3 - Article

C2 - 28726419

AN - SCOPUS:85027033092

SN - 1523-7060

VL - 19

SP - 4030

EP - 4033

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Hitoyol A and B, Two Norsesquiterpenoids from the Basidiomycete Coprinopsis cinerea

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this