New N-acylated aminoalkanoic acids from tea roots derived biocontrol agent Clonostachys rosea 15020

Jiaming Yu; Yue Zhang; Li Zhang; Jie Shi; Kun Wang; Weize Yuan; Zexu Lin; Shangqian Ning; Bohao Wang; Xinye Wang; Yuyang Qiu; Tom Hsiang; Lixin Zhang; Xueting Liu; Guoliang Zhu

Synthetic and Systems Biotechnology (Dec 2024)

New N-acylated aminoalkanoic acids from tea roots derived biocontrol agent Clonostachys rosea 15020

Jiaming Yu,
Yue Zhang,
Li Zhang,
Jie Shi,
Kun Wang,
Weize Yuan,
Zexu Lin,
Shangqian Ning,
Bohao Wang,
Xinye Wang,
Yuyang Qiu,
Tom Hsiang,
Lixin Zhang,
Xueting Liu,
Guoliang Zhu

Affiliations

Jiaming Yu: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
Yue Zhang: Department of Chemistry, Boston University, Boston, MA, USA
Li Zhang: Department of Chemistry, Boston University, Boston, MA, USA
Jie Shi: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
Kun Wang: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
Weize Yuan: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
Zexu Lin: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
Shangqian Ning: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
Bohao Wang: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
Xinye Wang: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
Yuyang Qiu: School of Insurance, Shandong University of Finance and Economics, Jinan, 250014, China
Tom Hsiang: School of Environmental Sciences, University of Guelph, Guelph, Ontario, N1G 2W1, Canada
Lixin Zhang: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
Xueting Liu: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
Guoliang Zhu: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China; Corresponding author.

Journal volume & issue: Vol. 9, no. 4
pp. 684 – 693

Abstract

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Four new N-acylated aminoalkanoic acids, namely clonoroseins E−H (1−4), together with three previously identified analogs, clonoroseins A, B, and D (5−7), were identified from the endophytic fungus Clonostachys rosea strain 15020 (CR15020), using Feature-based Molecular Networking (FBMN). The elucidation of their chemical structures, including their absolute configurations, was achieved through spectroscopic analysis combined with quantum chemical calculations. Bioinformatics analyses suggested that an iterative type I HR-PKS (CrsE) generates the polyketide side chain of these clonoroseins. Furthermore, a downstream adenylate-forming enzyme of the PKS (CrsD) was suspected to function as an amide synthetase. CrsD potentially facilitates the transformation of the polyketide moiety into an acyl-AMP intermediate, followed by nucleophilic substitution with either β-alanine or γ-aminobutyric acid to produce amide derivatives. These findings significantly expand our understanding of PKS-related products originating from C. rosea and also underscore the powerful application of FBMN analytical methods in characterization of new compounds.

Published in Synthetic and Systems Biotechnology

ISSN: 2405-805X (Online)
Publisher: KeAi Communications Co., Ltd.
Country of publisher: China
LCC subjects: Technology: Chemical technology: Biotechnology; Science: Biology (General)
Website: https://www.keaipublishing.com/en/journals/synthetic-and-systems-biotechnology/

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