Acacienone, a terpenoid-like natural product having an unprecedented C20 framework isolated from Acacia mangium leaves
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ORIGINAL PAPER
Acacienone, a terpenoid‑like natural product having an unprecedented C20 framework isolated from Acacia mangium leaves Yasumasa Hara1,2 · Yuichi Totsugi1 · Hiroshi Ichikawa1 · Shinji Harada1 · Kazuki Fujii1 · Firoj Ahmed3 · Samir K. Sadhu4 · Midori A. Arai5 · Masami Ishibashi1,2 Received: 4 September 2020 / Accepted: 1 October 2020 © The Japanese Society of Pharmacognosy 2020
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 · Terpenoid-like C20 natural product · Androsterone-like cyclopentenone moiety · Bangladesh plant
Introduction The genus Acacia belongs to the subfamily Mimosoideae of the family Leguminosae and is distributed across the northern parts of Australia to Southeast Asia. Numerous plants of the Leguminosae family, especially the subfamily Faboideae, produce isoflavones, whereas plants of the genus Acacia in the subfamily Mimosoideae produce Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11418-020-01457-y) contains supplementary material, which is available to authorized users. * Masami Ishibashi mish@chiba‑u.jp 1
Graduate School of Pharmaceutical Sciences, Chiba University, 1‑8‑1 Inohana, Chuo‑ku, Chiba 260‑8675, Japan
2
Plant Molecular Science Center, Chiba University, 1‑8‑1 Inohana, Chuo‑ku, Chiba 260‑8675, Japan
3
Department of Pharmaceutical Chemistry, University of Dhaka, Dhaka 1000, Bangladesh
4
Pharmacy Discipline, Khulna University, Khulna 9208, Bangladesh
5
Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, 3‑14‑1 Hiyoshi, Kohoku‑ku, Yokohama, Kanagawa 223‑8522, Japan
5-deoxy-type leucoanthocyanidins and proanthocyanidins [1]. In our previous study, four terpenoids (taepeenin D, (+)-drim-8-ene, labdanolic acid, and 8,15-labdanediol) and one flavonoid (quercetin 3-O-β-d-glucopyranosyl-4-O-βd-glucopyranoside) were isolated from the leaves of Acacia pennata [2]. Acacia mangium, belonging to the genus Acacia, is planted predominantly in tropical regions. Previous studies have reported the isolation of three flavonoids, 2,3-trans-3,4′,7,8-tetrahydroxyflavanone, teracacidin, and 4′,7,8-trihydroxyflavanone from the wood of Acacia mangium [3–5]. Nonetheless, only a few reports exist on the isolation of natural compounds from this plant. In this study, we describe the isolation and structural elucidation of a new C20 natural product, acacienone (1), obtained from methanol (MeOH) extracts of Acacia mangium leaves. Acacienone (1) was found to possess a unique c
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