1. Academic Validation
  2. Polyoxygenated Cyclohexenes and Their Chlorinated Derivatives from the Leaves of Uvaria cherrevensis

Polyoxygenated Cyclohexenes and Their Chlorinated Derivatives from the Leaves of Uvaria cherrevensis

  • J Nat Prod. 2019 Jan 25;82(1):101-110. doi: 10.1021/acs.jnatprod.8b00794.
Chiramet Auranwiwat 1 2 Puttandon Wongsomboon 1 Thanaphat Thaima 2 Roonglawan Rattanajak 3 Sumalee Kamchonwongpaisan 3 Anthony C Willis 4 Surat Laphookhieo 5 Stephen G Pyne 2 Thunwadee Limtharakul 1
Affiliations

Affiliations

  • 1 Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, the Graduate School and Research Center on Chemistry for Development of Health Promoting Products from Northern Resources , Chiang Mai University , Chiang Mai 50200 , Thailand.
  • 2 School of Chemistry , University of Wollongong , Wollongong , New South Wales 2522 , Australia.
  • 3 Medical Molecular Biology Research Unit , National Center for Genetic Engineering and Biotechnology , National Science and Technology Development Agency, Thailand Science Park , Pathumthani 12120 , Thailand.
  • 4 Research School of Chemistry, Australia National University , Canberra , ACT 2601 , Australia.
  • 5 Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University , Tasud, Muang , Chiang Rai 57100 , Thailand.
Abstract

The chemical study of leaf extracts from Uvaria cherrevensis resulted in the identification of 11 new polyoxygenated cyclohexenes, cherrevenols A-K (1-11), and a new seco-cyclohexene derivative, cherrevenol L (12). Nine known compounds (13-21) were also isolated. Three of the isolated compounds are chlorinated polyoxygenated cyclohexenes. The structures of these compounds were determined using spectroscopic methods and, in some cases (compounds 2, 6, 8, and 10), single-crystal X-ray crystallographic structural analysis or chemical correlation (compounds 6 and 7). Compounds 6 and 7 were both isolated as scalemic mixtures (ee 23-24%).

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