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

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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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References

  1. Kusano R, Ogawa S, Matsuo Y, Tanaka T, Yazaki Y, Kouno I (2011) α-Amylase and lipase inhibitory activity and structural characterization of Acacia bark proanthocyanidins. J Nat Prod 74:119–128

    Article  CAS  Google Scholar 

  2. Rifai Y, Arai MA, Koyano T, Kowithayakorn T, Ishibashi M (2010) Terpenoids and a flavonoid glycoside from Acacia pennata leaves as Hedgehog/GLI-mediated transcriptional inhibitors. J Nat Prod 73:995–997

    Article  CAS  Google Scholar 

  3. Mihara R, Barry KM, Mohammed CL, Mitsunaga T (2005) Comparison of antifungal and antioxidant activities of Acacia mangium and A. auriculiformis heartwood extracts. J Chem Ecol 31:789–804

    Article  CAS  Google Scholar 

  4. Barry KM, Mihara R, Davies NW, Mitsunaga T, Mohammed CL (2005) Polyphenols in Acacia mangium and Acacia auriculiformis heartwood with reference to heart rot susceptibility. J Wood Sci 51:615–621

    Article  CAS  Google Scholar 

  5. Zhang L, Chen J, Wang Y, Wu D, Xu M (2010) Phenolic extracts from Acacia mangium bark and their antioxidant activities. Molecules 15:3567–3577

    Article  CAS  Google Scholar 

  6. Ishibashi M (2019) Screening for natural products that affect Wnt signaling activity. J Nat Med 73:697–705

    Article  Google Scholar 

  7. Sato T, Arai MA, Yixizhuoma HY, Koyano T, Kowithayakorn T, Ishibashi M (2020) Cadinane sesquiterpenoids isolated from Santalum album using a screening program for Wnt signal inhibitory activity. J Nat Med 74:476–481

    Article  CAS  Google Scholar 

  8. Karmakar UK, Arai MA, Koyano T, Kowithayakorn T, Ishibashi M (2017) Boesenberols I-K, new isopimarane diterpenes from Boesenbergia pandurata with TRAIL-resistance overcoming activity. Tetrahedron Lett 58:3838–3841

    Article  CAS  Google Scholar 

  9. Ahmed F, Ishibashi M (2016) Bio-active natural products with TRAIL-resistance overcoming activity. Chem Pharm Bull 64:119–127

    Article  CAS  Google Scholar 

  10. Ohtani I, Kusumi T, Kashman Y, Kakisawa H (1991) High-field FT NMR application of Mosher’s method. The absolute configurations of marine terpenoids. J Am Chem Soc 113:4092–4096

    Article  CAS  Google Scholar 

  11. Kubo I, Miura I, Pettei MJ, Lee Y, Pilkiewicz FG, Nakanishi K (1977) Muzigadial and warburganal, potent antifungal antiyeast, and African army worm antifeedant agents. Tetrahedron Lett 18:4553–4556

    Article  Google Scholar 

  12. Corbett RE, Chee TL (1976) Extractives from Pseudowintera colorata. V. A new sesquiterpene lactone, colorata-4(13),8-dienolide. J Chem Soc Perkin Trans 1(8):850–857

    Article  Google Scholar 

  13. Jansen BJM, Groot A (2004) Occurrence, biological activity and synthesis of drimane sesquiterpenoids. Nat Prod Rep 21:449–477

    Article  CAS  Google Scholar 

  14. Dewick PM (2001a) Medicinal natural products: a biosynthetic approach, 2nd edn. John Wiley & Sons Ltd., England, pp 234–235

    Book  Google Scholar 

  15. Dewick PM (2001b) Medicinal natural products: a biosynthetic approach, 2nd edn. John Wiley & Sons Ltd., England, pp 277–278

    Book  Google Scholar 

  16. Shimizu Y, Sato Y, Mitsuhashi H (1969) Isolation and characterization of fukujusonorone, an 18-norpregnane derivative from Adonis amurensis Regel et Radd. Experientia 25:1129–1130

    Article  CAS  Google Scholar 

Download references

Acknowledgements

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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Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, 260-8675, Japan

    Yasumasa Hara, Yuichi Totsugi, Hiroshi Ichikawa, Shinji Harada, Kazuki Fujii & Masami Ishibashi

  2. Plant Molecular Science Center, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, 260-8675, Japan

    Yasumasa Hara & Masami Ishibashi

  3. Department of Pharmaceutical Chemistry, University of Dhaka, Dhaka, 1000, Bangladesh

    Firoj Ahmed

  4. Pharmacy Discipline, Khulna University, Khulna, 9208, Bangladesh

    Samir K. Sadhu

  5. Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa, 223-8522, Japan

    Midori A. Arai

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  1. Yasumasa Hara
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  2. Yuichi Totsugi
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  3. Hiroshi Ichikawa
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  4. Shinji Harada
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  8. Midori A. Arai
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  9. Masami Ishibashi
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Correspondence to Masami Ishibashi.

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Hara, Y., Totsugi, Y., Ichikawa, H. et al. Acacienone, a terpenoid-like natural product having an unprecedented C20 framework isolated from Acacia mangium leaves. J Nat Med 75, 99–104 (2021). https://doi.org/10.1007/s11418-020-01457-y

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  • DOI: https://doi.org/10.1007/s11418-020-01457-y

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