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
N1 - Publisher Copyright:
© 2023
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
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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 -