In vitro biotransformations of isocupressic acid by cow rumen preparations

Formation of agathic and dihydroagathic acids

Shwu Jiuan Lin, Robert E. Short, Stephen P. Ford, Elaine E. Grings, John P N Rosazza

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Isocupressic acid [15-hydroxylabda-8(17),13E-dien-19-oic acid] (1) was incubated under anaerobic conditions for 48 h in an in vitro ruminal fluid mixture and was transformed into two metabolites. The two metabolites were identified by GC/MS as agathic acid [labda-8(17),13(E)-diene-15,19-dioic acid] (4E) and dihydroagathic acid [labda-8(17)-ene-15,19-dioic acid] (6). Metabolite identities were confirmed by chemical conversions of isocupressic acid (1) and imbricataloic acid (5) into 4E and 6, respectively. Structures of synthetic metabolites were confirmed by 1H and 13C NMR, specific rotation, GC/MS, and high-resolution mass spectrometry. Plasma obtained from cows that were fed Ponderosa pine needles contained (13R,S)-dihydroagathic acid (6) but not isocupressic acid (1) or 4E. The results suggest that isocupressic acid (1) is metabolically oxidized to agathic acid (4E), subsequently reduced to (13R,S)-dihydroagathic acid (6) in the rumen, and then absorbed into the bloodstream of cattle.

Original languageEnglish
Pages (from-to)51-56
Number of pages6
JournalJournal of Natural Products
Volume61
Issue number1
DOIs
Publication statusPublished - Jan 1998
Externally publishedYes

Fingerprint

isocupressic acid
Rumen
Biotransformation
Metabolites
biotransformation
rumen
cows
acids
Acids
Pinus ponderosa
metabolites
Needles
Mass spectrometry
Mass Spectrometry
Nuclear magnetic resonance
Plasmas
Fluids
dihydroagathic acid
agathic acid
In Vitro Techniques

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

In vitro biotransformations of isocupressic acid by cow rumen preparations : Formation of agathic and dihydroagathic acids. / Lin, Shwu Jiuan; Short, Robert E.; Ford, Stephen P.; Grings, Elaine E.; Rosazza, John P N.

In: Journal of Natural Products, Vol. 61, No. 1, 01.1998, p. 51-56.

Research output: Contribution to journalArticle

Lin, Shwu Jiuan ; Short, Robert E. ; Ford, Stephen P. ; Grings, Elaine E. ; Rosazza, John P N. / In vitro biotransformations of isocupressic acid by cow rumen preparations : Formation of agathic and dihydroagathic acids. In: Journal of Natural Products. 1998 ; Vol. 61, No. 1. pp. 51-56.
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abstract = "Isocupressic acid [15-hydroxylabda-8(17),13E-dien-19-oic acid] (1) was incubated under anaerobic conditions for 48 h in an in vitro ruminal fluid mixture and was transformed into two metabolites. The two metabolites were identified by GC/MS as agathic acid [labda-8(17),13(E)-diene-15,19-dioic acid] (4E) and dihydroagathic acid [labda-8(17)-ene-15,19-dioic acid] (6). Metabolite identities were confirmed by chemical conversions of isocupressic acid (1) and imbricataloic acid (5) into 4E and 6, respectively. Structures of synthetic metabolites were confirmed by 1H and 13C NMR, specific rotation, GC/MS, and high-resolution mass spectrometry. Plasma obtained from cows that were fed Ponderosa pine needles contained (13R,S)-dihydroagathic acid (6) but not isocupressic acid (1) or 4E. The results suggest that isocupressic acid (1) is metabolically oxidized to agathic acid (4E), subsequently reduced to (13R,S)-dihydroagathic acid (6) in the rumen, and then absorbed into the bloodstream of cattle.",
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