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

生命情報学科

研究成果: Article › 査読

抄録

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.

本文言語	English
ページ（範囲）	99-104
ページ数	6
ジャーナル	Journal of Natural Medicines
巻	75
号	1
DOI	https://doi.org/10.1007/s11418-020-01457-y
出版ステータス	Published - 2021 1

ASJC Scopus subject areas

Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

文献へのアクセス

10.1007/s11418-020-01457-y

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引用スタイル

Acacienone, a terpenoid-like natural product having an unprecedented C20 framework isolated from Acacia mangium leaves. / Hara, Yasumasa; Totsugi, Yuichi; Ichikawa, Hiroshi; Harada, Shinji; Fujii, Kazuki; Ahmed, Firoj; Sadhu, Samir K.; Arai, Midori A.; Ishibashi, Masami.

In: Journal of Natural Medicines, Vol. 75, No. 1, 01.2021, p. 99-104.

研究成果: Article › 査読

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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.",

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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. ",

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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

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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.

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