Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Brief Communication
  • Published:

A concise total synthesis and PPAR activation activity of hericerin from Hericium erinaceum

Abstract

Hericerin is an isoindolinone meroterpenoid alkaloid isolated from medicinal mushroom Hericium erinaceum with some bioactivities. Herein, a concise total synthesis of hericerin was described, with four steps and 30% overall yield starting from commercially available methyl 3-hydroxy-5-methoxybenzoate and geranyl bromide. A comprehensive effect of hericerin on HepG2 cell line was observed and confirmed by transcriptomic analysis. Furthermore, hericerin was found to be a new PPARĪ³ agonist.

This is a preview of subscription content, access via your institution

Access options

Buy this article

Prices may be subject to local taxes which are calculated during checkout

Scheme 1
Fig. 1

References

  1. Minagawa K, et al. Stachyflin and acetylstachyflin, novel anti-influenza a virus substance, produced by Stachybotrys sp. RF-7260. I. Isolation, structure elucidation and biological activities. J Antibiot. 2002;55:155ā€“64.

    ArticleĀ  CASĀ  Google ScholarĀ 

  2. Roggo BE, et al. Novel Spirodihydrobenzofuranlactams as antagonists of endothelin and as inhibitors of HIV-1 protease produced by Stachybotrys sp. I. Fermentation, isolation and biological activity. J Antibiot. 1996;49:13ā€“9.

    ArticleĀ  CASĀ  Google ScholarĀ 

  3. Xu XM, De Guzman FS, Gloer JB, Shearer CA. Stachybotrins A and B: novel bioactive metabolites from a brackish water isolate of the fungus Stachybotrys sp. J Org Chem. 1992;57:6700ā€“03.

    ArticleĀ  CASĀ  Google ScholarĀ 

  4. Nozawa Y, Ito M, Sugawara K, Hanada K, Mizoue K. Stachybotrin C and parvisporin, novel neuritogenic compounds. II. structure determination. J Antibiot. 1997;50:641ā€“5.

    ArticleĀ  CASĀ  Google ScholarĀ 

  5. Nagwa E, et al. Isolation and characterization of the bioactive metabolites from the soil derived fungus Trichoderma viride. Mycology. 2018;9:70ā€“80.

    ArticleĀ  Google ScholarĀ 

  6. Kimura Y, et al. Hericerin, a new pollen growth inhibitor from the mushroom Hericium erinaceum. Agric Biol Chem. 1991;55:2673ā€“4.

    CASĀ  Google ScholarĀ 

  7. Li W, et al. Isolation and identification of aromatic compounds in lionā€™s mane mushroom and their anticancer activities. Food Chem. 2015;170:336ā€“42.

    ArticleĀ  CASĀ  Google ScholarĀ 

  8. Li W, et al. Hericirine, a novel anti-inflammatory alkaloid from Hericium erinaceum. Tetrahedron Lett. 2014;55:4086ā€“90.

    ArticleĀ  CASĀ  Google ScholarĀ 

  9. Wittstein K, et al. Corallocins A-C, nerve growth and brain-derived neurotrophic factor inducing metabolites from the mushroom Hericium coralloides. J Nat Prod. 2016;79:2264ā€“9.

    ArticleĀ  CASĀ  Google ScholarĀ 

  10. Miyazawa M, Takahashi T, Horibe I, Ishikawa R. Two new aromatic compounds and a new D-arabinitol ester from the mushroom Hericium erinaceum. Tetrahedron 2012;68:2007ā€“10.

    ArticleĀ  CASĀ  Google ScholarĀ 

  11. Wang K, et al. Erinacerins Cā€“L, isoindolin-1-ones with Ī±-glucosidase inhibitory activity from cultures of the medicinal mushroom hericium erinaceus. J Nat Prod. 2015;78:146ā€“54.

    ArticleĀ  CASĀ  Google ScholarĀ 

  12. Kobayashi S, et al. Total synthesis and structural revision of Hericerin. J Org Chem. 2012;77:5819ā€“22.

    ArticleĀ  CASĀ  Google ScholarĀ 

  13. Gomez-Prado RA, Miranda LD. Concise total synthesis of hericerin natural product. Tetrahedron Lett. 2013;54:2131ā€“2.

    ArticleĀ  CASĀ  Google ScholarĀ 

  14. Mun B, Kim S, Yoon H, Kim KH, Lee Y. Total synthesis of isohericerin, isohericenone, and erinacerin A: development of a copper-catalyzed methylboronation of terminal alkynes. J Org Chem. 2017;82:6349ā€“57.

    ArticleĀ  CASĀ  Google ScholarĀ 

  15. Sugamoto K, Kurogi C, Matsushita Y, Matsui T. Synthesis of 4-hydroxyderricin and related derivatives. Tetrahedron Lett. 2008;49:6639ā€“41.

    ArticleĀ  CASĀ  Google ScholarĀ 

  16. Sugamoto K, Matsushita Y, Kurogi C, Matsui T. Isobavachalcone: an overview. Tetrahedron. 2011;67:5346ā€“59.

    ArticleĀ  CASĀ  Google ScholarĀ 

  17. Sharma GVM, Sharma A, Sreenivas P, Mahalingam AK. Alternative lewis acids to effect claisen rearrangement. Synlett. 2000;05:615ā€“8.

    Google ScholarĀ 

  18. Lambert TH, MacMillan DWC. Development of a new Lewis acid-catalyzed [3,3]-sigmatropic rearrangement: the Allenoate-Claisen Rearrangement. J Am Chem Soc. 2002;124:13646ā€“7.

    ArticleĀ  CASĀ  Google ScholarĀ 

  19. Semple RK, Chatterjee VKK, Oā€™Rahilly S. PPAR and human metabolic disease. J Clin Investig. 2006;116:581ā€“9.

    ArticleĀ  CASĀ  Google ScholarĀ 

  20. Liu C, et al. Identification of a novel selective agonist of PPARĪ³ with no promotion of adipogenesis and less inhibition of osteoblastogenesis. Sci Rep. 2015;5:9530.

    ArticleĀ  CASĀ  Google ScholarĀ 

Download references

Acknowledgements

This study was supported by the National Natural Science Foundation of China (21472233 and 21877124).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hongwei Liu.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisherā€™s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zheng, Z., Chen, B., Wang, K. et al. A concise total synthesis and PPAR activation activity of hericerin from Hericium erinaceum. J Antibiot 73, 646ā€“649 (2020). https://doi.org/10.1038/s41429-020-0303-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41429-020-0303-8

Search

Quick links