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Anti‐Androgenic Activity of Fatty Acids
Author(s) -
Liu Jie,
Shimizu Kuniyoshi,
Kondo Ryuichiro
Publication year - 2009
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200800125
Subject(s) - chemistry , dihydrotestosterone , lncap , biochemistry , polyunsaturated fatty acid , reductase , degree of unsaturation , fatty acid , testosterone (patch) , androgen , prostate , enzyme , endocrinology , medicine , hormone , cancer , biology , organic chemistry
In this study, we show that 5 α ‐reductase derived from rat fresh liver was inhibited by certain aliphatic free fatty acids. The influences of chain length, unsaturation, oxidation, and esterification on the potency to inhibit 5 α ‐reductase activity were studied. Among the fatty acids we tested, inhibitory saturated fatty acids had C 12 –C 16 chains, and the presence of a CC bond enhanced the inhibitory activity. Esterification and hydroxy compounds were totally inactive. Finally, we tested the prostate cancer cell proliferation effect of free fatty acids. In keeping with the results of the 5 α ‐reductase assay, saturated fatty acids with a C 12 chain (lauric acid) and unsaturated fatty acids (oleic acid and α ‐linolenic acid) showed a proliferation inhibitory effect on lymph‐node carcinoma of the prostate (LNCaP) cells. At the same time, the testosterone‐induced prostate‐specific antigen (PSA) mRNA expression was down‐regulated. These results suggested that fatty acids with 5 α ‐reductase inhibitory activity block the conversion of testosterone to 5 α ‐dihydrotestosterone (DHT) and then inhibit the proliferation of prostate cancer cells.