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Molecules
Volume 23
Issue 11
10.3390/molecules23112772
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Article

Studies on the Chemical Diversities of Secondary Metabolites Produced by Neosartorya fischeri via the OSMAC Method

by
You-Min Ying
1,
Lu Huang
1,
Ting Tian
1,
Cui-Yu Li
1,
Shi-Lei Wang
2,
Lie-Feng Ma
1,
Wei-Guang Shan
1,
Jian-Wei Wang
1,* and
Zha-Jun Zhan
1,*
1
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, China
2
College of Biology and Environment Engineering, Zhejiang Shuren University, Hangzhou 310015, China
*
Authors to whom correspondence should be addressed.
Molecules 2018, 23(11), 2772; https://doi.org/10.3390/molecules23112772
Received: 22 September 2018 / Revised: 12 October 2018 / Accepted: 22 October 2018 / Published: 25 October 2018
(This article belongs to the Section Natural Products Chemistry)
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Abstract

The One Strain Many Compounds (OSMAC) method was applied to explore the chemical diversities of secondary metabolites produced by Neosartorya fischeri NRRL 181. Four pyripyropenes 1–4, eight steroids 5–11, and four prenylated indole alkaloids 12–15, were obtained from the fungus cultured in petri dishes containing potato dextrose agar (PDA). 1,7,11-trideacetylpyripyropene A (1) and 1,11-dideacetyl pyripyropene A (2) were obtained and spectroscopically characterized (1D, 2D NMR, and HR-ESI-MS) from a natural source for the first time. It offered a sustainable source of these two compounds, which were usually used as starting materials in preparing pyripyropene derivatives. In addition, as compared with all the other naturally occurring pyripyropenes, 1 and 2 possessed unique acetylation patterns that did not follow the established late-step biosynthetic rules of pyripyropenes. The natural occurrence of 1 and 2 in the fungus implied that the timing and order of hydroxylation and acetylation in the late-step biosynthetic pathway of pyripyropenes remained to be revealed. The isolation and identification of 1–15 indicated that the OSMAC method could remarkably alter the metabolic profile and enrich the chemical diversities of fungal metabolites. Compounds 1–4 exhibited no obvious cytotoxicity against the triple-negative breast cancer cell line MDA-MB-231 as compared with taxol. View Full-Text
Keywords: OSMAC; pyripyropenes; Neosartorya fischeri; secondary metabolites OSMAC; pyripyropenes; Neosartorya fischeri; secondary metabolites
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MDPI and ACS Style

Ying, Y.-M.; Huang, L.; Tian, T.; Li, C.-Y.; Wang, S.-L.; Ma, L.-F.; Shan, W.-G.; Wang, J.-W.; Zhan, Z.-J. Studies on the Chemical Diversities of Secondary Metabolites Produced by Neosartorya fischeri via the OSMAC Method. Molecules 2018, 23, 2772. https://doi.org/10.3390/molecules23112772

AMA Style

Ying Y-M, Huang L, Tian T, Li C-Y, Wang S-L, Ma L-F, Shan W-G, Wang J-W, Zhan Z-J. Studies on the Chemical Diversities of Secondary Metabolites Produced by Neosartorya fischeri via the OSMAC Method. Molecules. 2018; 23(11):2772. https://doi.org/10.3390/molecules23112772

Chicago/Turabian Style

Ying, You-Min, Lu Huang, Ting Tian, Cui-Yu Li, Shi-Lei Wang, Lie-Feng Ma, Wei-Guang Shan, Jian-Wei Wang, and Zha-Jun Zhan. 2018. "Studies on the Chemical Diversities of Secondary Metabolites Produced by Neosartorya fischeri via the OSMAC Method" Molecules 23, no. 11: 2772. https://doi.org/10.3390/molecules23112772

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