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 journalArticle

22 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

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Bioassay
Prostaglandin-Endoperoxide Synthases
Biological Assay
Inhibitory Concentration 50
Assays
Antioxidants
Antennas
Cyclooxygenase 1
Rubiaceae
Acids
Catechin
Cyclooxygenase 2
Fractionation
Cytochromes c
Skeleton
Free Radicals
cycloartane
2,2-diphenyl-1-picrylhydrazyl

ASJC Scopus subject areas

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

Cite this

Cyclooxygenase-inhibitory and antioxidant constituents of the aerial parts of Antirhea acutata. / Lee, Dongho; Jung Park, Eun; Cuendet, Muriel; Axelrod, Franklin; Chavez, Pedro I.; Fong, Harry H S; Pezzuto, John M.; Kinghorn, A. Douglas.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 11, No. 12, 18.06.2001, p. 1565-1568.

Research output: Contribution to journalArticle

Lee, D, Jung Park, E, Cuendet, M, Axelrod, F, Chavez, PI, Fong, HHS, Pezzuto, JM & Kinghorn, AD 2001, 'Cyclooxygenase-inhibitory and antioxidant constituents of the aerial parts of Antirhea acutata', Bioorganic and Medicinal Chemistry Letters, vol. 11, no. 12, pp. 1565-1568. https://doi.org/10.1016/S0960-894X(01)00129-9
Lee, Dongho ; Jung Park, Eun ; Cuendet, Muriel ; Axelrod, Franklin ; Chavez, Pedro I. ; Fong, Harry H S ; Pezzuto, John M. ; Kinghorn, A. Douglas. / Cyclooxygenase-inhibitory and antioxidant constituents of the aerial parts of Antirhea acutata. In: Bioorganic and Medicinal Chemistry Letters. 2001 ; Vol. 11, No. 12. pp. 1565-1568.
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