Microbial transformation of some triterpenoids of Guayule resin by Chaetomium sp.

Marielle C. Inacio; Weimao Zhong; Ya Ming Xu; E. M.Kithsiri Wijeratne; Chandrashekhar Madasu; István Molnár; A. A.Leslie Gunatilaka

doi:10.1016/j.phytol.2023.05.001

Microbial transformation of some triterpenoids of Guayule resin by Chaetomium sp.

Marielle C. Inacio, Weimao Zhong, Ya Ming Xu, E. M.Kithsiri Wijeratne, Chandrashekhar Madasu, István Molnár (Corresponding Author), A. A.Leslie Gunatilaka (Corresponding Author)

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University of Arizona

Research output: Contribution to journal › Article › Scientific › peer-review

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Abstract

Microbial biotransformation of argentatin A (1), isoargentatin A (2) and argentatin C (3), the triterpenoid constituents of guayule (Parthenium argentatum) resin was conducted with Chaetomium sp. PA001, an endophytic fungus of the same plant. The experiments yielded six new products (4–9) formed by: (i) nucleophilic oxygenation of the 3-ketone moiety resulting in Baeyer-Villiger oxidation; (ii) lactone ring opening of these oxidation products; (iii) rearrangement of the 9(10)-cyclopropane ring; and (iv) reduction of the 3-ketone moiety. The structures of all new biotransformation products were established by detailed analysis of their spectroscopic data. None of the products exhibited any antimicrobial activity. However, the hydroxy-carboxylic acid derivative 5 of argentatin A showed weak cytotoxic activity, but improved selectivity against human breast cancer cell line MCF-7 compared to the parent compound. This constitutes the first report of microbial biotransformation of isoargentatin A and argentatin C.

Original language	English
Pages (from-to)	124-130
Number of pages	7
Journal	Phytochemistry Letters
Volume	55
DOIs	https://doi.org/10.1016/j.phytol.2023.05.001
Publication status	Published - Jun 2023
MoE publication type	A1 Journal article-refereed

Funding

This project was supported by the USDA-NIFA (grant # 2017- 68005–26867 ; Dr. Kimberly Ogden, PI) and Hatch Projects 1005072 and 1020652 to A.A.L.G and I.M. Any opinions, findings, conclusions, or recommendations expressed in this publication/work are those of the authors and do not necessarily reflect the view of the U.S. Department of Agriculture. We thank Dr. Lijiang Xuan, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, P. R. China for HRMS data. This project was supported by the USDA-NIFA (grant # 2017- 68005–26867; Dr. Kimberly Ogden, PI) and Hatch Projects 1005072 and 1020652 to A.A.L.G and I.M. Any opinions, findings, conclusions, or recommendations expressed in this publication/work are those of the authors and do not necessarily reflect the view of the U.S. Department of Agriculture. We thank Dr. Lijiang Xuan, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, P. R. China for HRMS data.

Keywords

Argentatins
Biotransformation
Chaetomium sp.PA001
Enzymatic Baeyer-Villiger oxidation
Guayule
Parthenium argentatum

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.phytol.2023.05.001

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title = "Microbial transformation of some triterpenoids of Guayule resin by Chaetomium sp.",

abstract = "Microbial biotransformation of argentatin A (1), isoargentatin A (2) and argentatin C (3), the triterpenoid constituents of guayule (Parthenium argentatum) resin was conducted with Chaetomium sp. PA001, an endophytic fungus of the same plant. The experiments yielded six new products (4–9) formed by: (i) nucleophilic oxygenation of the 3-ketone moiety resulting in Baeyer-Villiger oxidation; (ii) lactone ring opening of these oxidation products; (iii) rearrangement of the 9(10)-cyclopropane ring; and (iv) reduction of the 3-ketone moiety. The structures of all new biotransformation products were established by detailed analysis of their spectroscopic data. None of the products exhibited any antimicrobial activity. However, the hydroxy-carboxylic acid derivative 5 of argentatin A showed weak cytotoxic activity, but improved selectivity against human breast cancer cell line MCF-7 compared to the parent compound. This constitutes the first report of microbial biotransformation of isoargentatin A and argentatin C.",

keywords = "Argentatins, Biotransformation, Chaetomium sp.PA001, Enzymatic Baeyer-Villiger oxidation, Guayule, Parthenium argentatum",

author = "Inacio, {Marielle C.} and Weimao Zhong and Xu, {Ya Ming} and Wijeratne, {E. M.Kithsiri} and Chandrashekhar Madasu and Istv{\'a}n Moln{\'a}r and Gunatilaka, {A. A.Leslie}",

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year = "2023",

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doi = "10.1016/j.phytol.2023.05.001",

language = "English",

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AU - Inacio, Marielle C.

AU - Zhong, Weimao

AU - Xu, Ya Ming

AU - Wijeratne, E. M.Kithsiri

AU - Madasu, Chandrashekhar

AU - Molnár, István

AU - Gunatilaka, A. A.Leslie

PY - 2023/6

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N2 - Microbial biotransformation of argentatin A (1), isoargentatin A (2) and argentatin C (3), the triterpenoid constituents of guayule (Parthenium argentatum) resin was conducted with Chaetomium sp. PA001, an endophytic fungus of the same plant. The experiments yielded six new products (4–9) formed by: (i) nucleophilic oxygenation of the 3-ketone moiety resulting in Baeyer-Villiger oxidation; (ii) lactone ring opening of these oxidation products; (iii) rearrangement of the 9(10)-cyclopropane ring; and (iv) reduction of the 3-ketone moiety. The structures of all new biotransformation products were established by detailed analysis of their spectroscopic data. None of the products exhibited any antimicrobial activity. However, the hydroxy-carboxylic acid derivative 5 of argentatin A showed weak cytotoxic activity, but improved selectivity against human breast cancer cell line MCF-7 compared to the parent compound. This constitutes the first report of microbial biotransformation of isoargentatin A and argentatin C.

AB - Microbial biotransformation of argentatin A (1), isoargentatin A (2) and argentatin C (3), the triterpenoid constituents of guayule (Parthenium argentatum) resin was conducted with Chaetomium sp. PA001, an endophytic fungus of the same plant. The experiments yielded six new products (4–9) formed by: (i) nucleophilic oxygenation of the 3-ketone moiety resulting in Baeyer-Villiger oxidation; (ii) lactone ring opening of these oxidation products; (iii) rearrangement of the 9(10)-cyclopropane ring; and (iv) reduction of the 3-ketone moiety. The structures of all new biotransformation products were established by detailed analysis of their spectroscopic data. None of the products exhibited any antimicrobial activity. However, the hydroxy-carboxylic acid derivative 5 of argentatin A showed weak cytotoxic activity, but improved selectivity against human breast cancer cell line MCF-7 compared to the parent compound. This constitutes the first report of microbial biotransformation of isoargentatin A and argentatin C.

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KW - Enzymatic Baeyer-Villiger oxidation

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JO - Phytochemistry Letters

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ER -

Microbial transformation of some triterpenoids of Guayule resin by Chaetomium sp.

Abstract

Funding

Keywords

UN SDGs

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