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Chemical characterization of lysyl oxidase inhibitor from avocado seed oil
Author(s) -
Rosenblat Gennady,
Kagan Herbert M.,
Shah Manzoor A.,
Spiteller Gerchard,
Neeman Itshak
Publication year - 1995
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02638904
Subject(s) - lysyl oxidase , chemistry , furan , moiety , biochemistry , enzyme , oxidase test , substrate (aquarium) , stereochemistry , organic chemistry , biology , ecology
The active factor of lysyl oxidase inhibition was separated from unsaponifiables of avocado seed oil and characterized by gas chromatography‐mass spectrometry. Results indicated the presence of furan‐containing lipids in the active factor mixture and also showed a structural difference compared to previously reported furan‐containing lipids of avocado which relates to the length of the hydrocarbon chain substituent. Another structural difference evinced was the availability of the hydroxyl group in the aliphatic moiety of the investigated substances. A purified mixture of furan‐containing compounds was tested in vitro for inhibitory activity on pure bovine aorta lysyl oxidase. It was shown that mixing furan‐containing lipids in Tween 80 reversibly inhibited pure bovine aorta lysyl oxidase activity against tritiated recombinant tropoelastin with the I 50 value of inhibition of 105 µM. These in vitro studies suggested that the mixture of avocado seed oil furan‐containing lipids was not a substrate‐specific inhibitor of lysyl oxidase, and it might prove to be useful as a potential antifibrotic drug. Moreover, the unique chemistry of the studied compound for lysyl oxidase inhibition should enable the designing of new probes of the active site of this important enzyme.