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^*
, A. A.Leslie Gunatilaka^*

^*Corresponding author for this work

Not published at VTT

University of Arizona

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

3 Citations (Scopus)

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
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.

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

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

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10.1016/j.phytol.2023.05.001

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@article{e7e233a9e2384f308fdfa07a229056a8,

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\}",

note = "Publisher Copyright: {\textcopyright} 2023",

year = "2023",

month = jun,

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

language = "English",

volume = "55",

pages = "124--130",

journal = "Phytochemistry Letters",

issn = "1874-3900",

publisher = "Elsevier",

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TY - JOUR

T1 - Microbial transformation of some triterpenoids of Guayule resin by Chaetomium sp.

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

Y1 - 2023/6

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.

KW - Argentatins

KW - Biotransformation

KW - Chaetomium sp.PA001

KW - Enzymatic Baeyer-Villiger oxidation

KW - Guayule

KW - Parthenium argentatum

UR - https://www.scopus.com/pages/publications/85159406995

U2 - 10.1016/j.phytol.2023.05.001

DO - 10.1016/j.phytol.2023.05.001

M3 - Article

AN - SCOPUS:85159406995

SN - 1874-3900

VL - 55

SP - 124

EP - 130

JO - Phytochemistry Letters

JF - Phytochemistry Letters

ER -

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

Abstract

Funding

UN SDGs

Keywords

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