Anti-inflammatory and α-Glucosidase Inhibitory Activities of Labdane and Norlabdane Diterpenoids from the Rhizomes of Amomum villosum

  • J Nat Prod. 2019 Nov 22;82(11):2963-2971. doi: 10.1021/acs.jnatprod.9b00283.
Hong Yin  1 ,  Wen-Jia Dan  1 ,  Bo-Yi Fan  2 ,  Chao Guo  3 ,  Kui Wu  4 ,  Ding Li  1 ,  Kui-Feng Xian  1 ,  Gennaro Pescitelli  5 ,  Jin-Ming Gao  1
Affiliations
  • 1. Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy , Northwest A&F University , Yangling 712100 , Shaanxi , People's Republic of China.
  • 2. School of Pharmacy , Nantong University , Nantong 226001 , Jiangsu , People's Republic of China.
  • 3. School of Pharmacy , Xinxiang Medical University , Xinxiang 453003 , Henan , People's Republic of China.
  • 4. Department of Chemistry , University at Albany, State University of New York , Albany , New York 12222 , United States.
  • 5. Dipartimento di Chimica e Chimica Industriale , Università di Pisa , Pisa 56124 , Italy.
PMID: 31710213 DOI: 10.1021/acs.jnatprod.9b00283
Abstract

A new tetranorditerpenoid (1), two new labdane Diterpenoids (2, 3), and nine known analogues (4-12) were isolated from the rhizomes of Amomum villosum var. xanthioides. Compound 1 is an unprecedented rearranged tetranorlabdane diterpenoid, featuring a 6/6/5 fused tricarbocyclic skeleton with an α,β-unsaturated cyclopentenone unit, while 2 is a structurally rare labdane diterpenoid carrying a five-membered cyclic anhydride moiety. Their structures and absolute configurations were established on the basis of spectroscopic data and the experimental and calculated ECD data. Compound 4 showed inhibitory activity against nitric oxide production, with an IC50 value of 2.4 μM, and also inhibited α-glucosidase activity (IC50 = 10.0 μM).

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