Naphthalene derivatives and halogenate quinoline from the coral-derived fungus Trichoderma harzianum (XS-20090075) through OSMAC approach

Abstract

OSMAC approach was performed on the soft coral-derived fungus Trichoderma harzianum (XS-20090075) leading to the significant changes of its secondary metabolites by using two different cultures. A new naphthalene derivative, trichoharzin B (1) and a new natural product, methyl-trichoharzin (2) were isolated by using rice medium. Whereas, a new natural product, ethyl 2-bromo-4-chloroquinoline-3-carboxylate (9) was obtained by using Czapek’s medium. Their structures were established by extensive spectroscopic investigation. The absolute configuration of 5 was determined by single-crystal X-ray diffraction. Compound 9 was the first halogenate quinoline derivative isolated from the genus of Trichoderma.

Graphical Abstract

Keywords:

• Soft coral-derived fungus
• Trichoderma harzianum
• OSMAC
• naphthalene derivative
• halogenate quinolone

Supplementary material

Supplementary material relating to this article is available online, NMR, single-crystal and MS data for 1, 2, 5 and 9.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was financially supported by the National Science and Technology Major Project for Significant New Drugs Development, China [Grant number 2018ZX09735-004]; the National Natural Science Foundation of China [Grant number 81673350, U1606403]; the Fundamental Research Funds for the Central Universities of China [Grant number 201962002]; Open Research Fund Program of Qingdao National Laboratory for Marine Science and Technology [Grant number QNLM2016ORP0302], and the Taishan Scholars Program, China.