Mechanistic Insights into the Nonenzymatic Biosynthesis of Artemisinin and Related Natural Products: A Quantum Chemical Study DOI
Maocai Yan, Xiang Ding, Likun Zhao

et al.

Journal of Chemical Information and Modeling, Journal Year: 2025, Volume and Issue: unknown

Published: April 13, 2025

Artemisinin (Qinghaosu) is an important antimalaria natural medicine containing a unique endoperoxide bridge in its sesquiterpene structure. The last phase of artemisinin biosynthesis involves conversion dihydroartemisinic acid (DHAA) to artemisinin, and the detailed mechanism remains unclear. Based on previous experimental studies, this work investigated possible nonenzymatic DHAA identified most chemically plausible reaction pathway using quantum chemical computations. rate-determining step acid-catalyzed oxidation enol by triplet O2, with overall free energy barrier 22.5 kcal/mol. This also gives byproducts dihydroarteannuin B dihydro-epi-arteannuin B. In addition, formation 21 products from Artemisia annua was discussed work. These results provide fundamental knowledge biosynthetic processes related products, as well references for semisynthesis structural modification studies artemisinin.

Language: Английский

Humanized rodent models of neurodegenerative diseases and other brain disorders DOI
X.B Zhang, Jianxiang Wang, Jiewen Zhang

et al.

Neuroscience & Biobehavioral Reviews, Journal Year: 2025, Volume and Issue: unknown, P. 106112 - 106112

Published: March 1, 2025

Language: Английский

Citations

0
Mechanistic Insights into the Nonenzymatic Biosynthesis of Artemisinin and Related Natural Products: A Quantum Chemical Study DOI
Maocai Yan, Xiang Ding, Likun Zhao

et al.

Journal of Chemical Information and Modeling, Journal Year: 2025, Volume and Issue: unknown

Published: April 13, 2025

Artemisinin (Qinghaosu) is an important antimalaria natural medicine containing a unique endoperoxide bridge in its sesquiterpene structure. The last phase of artemisinin biosynthesis involves conversion dihydroartemisinic acid (DHAA) to artemisinin, and the detailed mechanism remains unclear. Based on previous experimental studies, this work investigated possible nonenzymatic DHAA identified most chemically plausible reaction pathway using quantum chemical computations. rate-determining step acid-catalyzed oxidation enol by triplet O2, with overall free energy barrier 22.5 kcal/mol. This also gives byproducts dihydroarteannuin B dihydro-epi-arteannuin B. In addition, formation 21 products from Artemisia annua was discussed work. These results provide fundamental knowledge biosynthetic processes related products, as well references for semisynthesis structural modification studies artemisinin.

Language: Английский

Citations

0