Cyclooxygenase-inhibitory and antioxidant constituents of the aerial parts of Antirhea acutata

Dongho Lee, Eun Jung Park, Muriel Cuendet, Franklin Axelrod, Pedro I. Chavez, Harry H.S. Fong, John M. Pezzuto, A. Douglas Kinghorn

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

Two new compounds, (6S)-hydroxy-29-nor-3,4-seco-cycloart-4(30),24-dien-3-oic acid (1) and 8-[1-(3,4-dihydroxyphenyl)-3-methoxy-3-oxopropyl]epicatechin (3), were isolated by bioassay-guided fractionation from the aerial parts of Antirhea acutata (DC.) Urb. (Rubiaceae). Compound 1 showed moderate inhibitory activities in cyclooxygenase-1 and -2 assays (IC50 43.7 and 4.7 μM, respectively), while compound 3 was active in 1,1-diphenyl-2-picrylhydrazyl free-radical and cytochrome c reduction antioxidant assays (IC50 29.1 and 16.3 μM, respectively). Additionally, one further new compound was isolated, (3S,24S)-25-trihydroxy-9,19-cycloartane-29-oic acid (2), but this was inactive in the bioassay systems used. Compound 1 is based on the unprecedented 29-nor-3,4-seco-cycloartane skeleton.

Original languageEnglish
Pages (from-to)1565-1568
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume11
Issue number12
DOIs
Publication statusPublished - 2001 Jun 18
Externally publishedYes

Bibliographical note

Funding Information:
This work was supported by Program Project P01-CA-48112 funded by the National Cancer Institute, NIH, Bethesda, MD. We thank Dr. D. Chávez, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago (UIC), for technical advice and Dr. K. Fagerquist, Mass Spectrometry Facility, Department of Chemistry, University of Minnesota, Minneapolis, MN, for the mass spectral data. We are grateful to the Research Resources Center, UIC, for the provision of certain spectroscopic equipment used in this investigation.

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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