114394-01-3Relevant articles and documents
Urodiolenone from grapefruit juice, a urinary metabolite found in hypertensive subjects
Chayen, Ralph,Mazur, Yehuda,Wyler, Hugo,Berman, Elisha,Potgieter, Eleanor,Goldberg, Sara
, p. 369 - 372 (1988)
Urodiolenone, a compound isolated from the urine of hypertensive subjects, is a 1:1 epimeric mixture of two dihydroxy derivatives of nookatone, a constituent of grapefruit. The structure of urodiolenone was suggested by NMR spectroscopy and confirmed by partial synthesis from nootkatone, a sesquiterpenoid ketone with a valencene skeleton. In addition, we show that urodiolenone itself is also present in the grapefruit in free form and possibly also as a glucuronide. The question whether urodiolenone is produced exogenously or endogenously is discussed.
Biotransformation of citrus aromatics nootkatone and valencene by microorganisms
Furusawa, Mai,Hashimoto, Toshihiro,Noma, Yoshiaki,Asakawa, Yoshinori
, p. 1423 - 1429 (2007/10/03)
Biotransformations of the sesquiterpene ketone nootkatone (1) from the crude drug Alpiniae Fructus and grapefruit oil, and the sesquiterpene hydrocarbon valencene (2) from Valencia orange oil were carried out with microorganisms such as Aspergillus niger, Botryosphaeria dothidea, and Fusarium culmorum to afford structurally interesting metabolites. Their stereostructures were established by a combination of high-resolution NMR spectral and X-ray crystallographic analysis and chemical reaction. Metabolic pathways of compounds 1 and 2 by A. niger are proposed.
