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 - Funding Information:
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.
Funding Information:
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.
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
UR - http://www.scopus.com/inward/record.url?scp=85159406995&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85159406995&partnerID=8YFLogxK
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 -