Acacienone, a terpenoid-like natural product having an unprecedented C20 framework isolated from Acacia mangium leaves

Yasumasa Hara; Yuichi Totsugi; Hiroshi Ichikawa; Shinji Harada; Kazuki Fujii; Firoj Ahmed; Samir K. Sadhu; Midori A. Arai; Masami Ishibashi

doi:10.1007/s11418-020-01457-y

Acacienone, a terpenoid-like natural product having an unprecedented C20 framework isolated from Acacia mangium leaves

Yasumasa Hara, Yuichi Totsugi, Hiroshi Ichikawa, Shinji Harada, Kazuki Fujii, Firoj Ahmed, Samir K. Sadhu, Midori A. Arai, Masami Ishibashi

Department of Biosciences and Informatics

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

Abstract

A novel C20 natural product, acacienone (1), was isolated from the leaves of Acacia mangium collected in Bangladesh. The structure of compound 1 was elucidated by spectral studies and X-ray crystallographic analysis. Acacienone (1) possesses a terpenoid-related tetracyclic framework containing 20 carbons with biogenetically unusual structural features: (i) vicinal C1-branches at the C-3 and C-4 positions in the A ring, and (ii) a cyclopentenone D ring in an androsterone-like assembly, lacking a methyl group at the C-13 position.

Original language	English
Pages (from-to)	99-104
Number of pages	6
Journal	Journal of Natural Medicines
Volume	75
Issue number	1
DOIs	https://doi.org/10.1007/s11418-020-01457-y
Publication status	Published - 2021 Jan

Keywords

Acacia mangium
Androsterone-like cyclopentenone moiety
Bangladesh plant
Terpenoid-like C20 natural product

ASJC Scopus subject areas

Molecular Medicine

Access to Document

10.1007/s11418-020-01457-y

Cite this

@article{fcbb45983cc64eb0a37ee1e8a1c0e785,

title = "Acacienone, a terpenoid-like natural product having an unprecedented C20 framework isolated from Acacia mangium leaves",

abstract = "A novel C20 natural product, acacienone (1), was isolated from the leaves of Acacia mangium collected in Bangladesh. The structure of compound 1 was elucidated by spectral studies and X-ray crystallographic analysis. Acacienone (1) possesses a terpenoid-related tetracyclic framework containing 20 carbons with biogenetically unusual structural features: (i) vicinal C1-branches at the C-3 and C-4 positions in the A ring, and (ii) a cyclopentenone D ring in an androsterone-like assembly, lacking a methyl group at the C-13 position.",

keywords = "Acacia mangium, Androsterone-like cyclopentenone moiety, Bangladesh plant, Terpenoid-like C20 natural product",

author = "Yasumasa Hara and Yuichi Totsugi and Hiroshi Ichikawa and Shinji Harada and Kazuki Fujii and Firoj Ahmed and Sadhu, {Samir K.} and Arai, {Midori A.} and Masami Ishibashi",

note = "Funding Information: This work was supported by KAKENHI Grant No. 20H03394 and 20K16024 from the Japan Society for the Promotion of Science. We would like to thank Dr. Tomoki Yoneda, Hokkaido University, for valuable suggestions. Publisher Copyright: {\textcopyright} 2020, The Japanese Society of Pharmacognosy.",

year = "2021",

month = jan,

doi = "10.1007/s11418-020-01457-y",

language = "English",

volume = "75",

pages = "99--104",

journal = "Journal of Natural Medicines",

issn = "1340-3443",

publisher = "Springer Japan",

number = "1",

}

TY - JOUR

T1 - Acacienone, a terpenoid-like natural product having an unprecedented C20 framework isolated from Acacia mangium leaves

AU - Hara, Yasumasa

AU - Totsugi, Yuichi

AU - Ichikawa, Hiroshi

AU - Harada, Shinji

AU - Fujii, Kazuki

AU - Ahmed, Firoj

AU - Sadhu, Samir K.

AU - Arai, Midori A.

AU - Ishibashi, Masami

N1 - Funding Information: This work was supported by KAKENHI Grant No. 20H03394 and 20K16024 from the Japan Society for the Promotion of Science. We would like to thank Dr. Tomoki Yoneda, Hokkaido University, for valuable suggestions. Publisher Copyright: © 2020, The Japanese Society of Pharmacognosy.

PY - 2021/1

Y1 - 2021/1

N2 - A novel C20 natural product, acacienone (1), was isolated from the leaves of Acacia mangium collected in Bangladesh. The structure of compound 1 was elucidated by spectral studies and X-ray crystallographic analysis. Acacienone (1) possesses a terpenoid-related tetracyclic framework containing 20 carbons with biogenetically unusual structural features: (i) vicinal C1-branches at the C-3 and C-4 positions in the A ring, and (ii) a cyclopentenone D ring in an androsterone-like assembly, lacking a methyl group at the C-13 position.

AB - A novel C20 natural product, acacienone (1), was isolated from the leaves of Acacia mangium collected in Bangladesh. The structure of compound 1 was elucidated by spectral studies and X-ray crystallographic analysis. Acacienone (1) possesses a terpenoid-related tetracyclic framework containing 20 carbons with biogenetically unusual structural features: (i) vicinal C1-branches at the C-3 and C-4 positions in the A ring, and (ii) a cyclopentenone D ring in an androsterone-like assembly, lacking a methyl group at the C-13 position.

KW - Acacia mangium

KW - Androsterone-like cyclopentenone moiety

KW - Bangladesh plant

KW - Terpenoid-like C20 natural product

UR - http://www.scopus.com/inward/record.url?scp=85092463273&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85092463273&partnerID=8YFLogxK

U2 - 10.1007/s11418-020-01457-y

DO - 10.1007/s11418-020-01457-y

M3 - Article

C2 - 33048280

AN - SCOPUS:85092463273

SN - 1340-3443

VL - 75

SP - 99

EP - 104

JO - Journal of Natural Medicines

JF - Journal of Natural Medicines

IS - 1

ER -

Acacienone, a terpenoid-like natural product having an unprecedented C20 framework isolated from Acacia mangium leaves

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this