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Issue 88, 2015
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Endophyte inspired chemical diversity from beta-caryophyllene

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The natural product (−)-β-caryophyllene is considered as an ideal initiator to generate diverse scaffolds by transannular cyclization due to its macrocyclic structure and abundant availability in nature. An endophytic strain Aspergillus tubingensis KJ-9 was screened in our lab to catalyse remodeling of the β-caryophyllene skeleton. In the fermentation, macrocyclic β-caryophyllene was remodeled into a series of natural product-like polycyclic compounds with unusual diverse skeletons (1–7). Their structures, including absolute configuration, were elucidated by several spectroscopic methods (1D & 2D NMR, HRMS, ECD and X-ray diffraction). Especially, scaffolds 1 and 3 were not found in acid-catalysed products before. Our findings demonstrated the potential of endophytic fungi for catalyzing macrocyclic compounds into diverse products.

Graphical abstract: Endophyte inspired chemical diversity from beta-caryophyllene

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The article was received on 19 Jul 2015, accepted on 19 Aug 2015 and first published on 19 Aug 2015

Article type: Communication
DOI: 10.1039/C5RA14243A
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RSC Adv., 2015,5, 72433-72436

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    Endophyte inspired chemical diversity from beta-caryophyllene

    H. Tang, J. Gao and Q. Zhang, RSC Adv., 2015, 5, 72433
    DOI: 10.1039/C5RA14243A

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