A sphingolipid and tyrosinase inhibitors from the fruiting body of Phellinus linteus.
This paper for the first time reports the isolation of 5 compounds from Phellinus linteus. A sphingolipid (1) and two tyrosinase inhibitory compounds (2, 3) along with two carboxylic acids (4, 5), were isolated from the fruiting body of Phellinus linteus (Berk & Curt) Aoshima. The structure of compound 1 was identified as 1-omicron-beta-D-glucopyranosyl-(2S, 3R, 4E, 8E)-2-[(2R)-2-hydroxyhexadecanoylamino]-9-methyl-4,8-octadecadiene-1,3-diol, known as cerebroside B, based on spectroscopic methods such as 1 D and 2D NMR as well as by acid hydrolysis. Compounds 2 -5 were identified as protocatechualdehyde (2), 5-hydroxymethyl-2-furaldehyde (HMF) (3), succinic acid (4), and fumaric acid (5) based on the spectroscopic evidence. Compounds 2 and 3 inhibited the oxidation of L-tyrosine catalyzed by mushroom tyrosinase with an IC50 of 0.40 and 90.8 microg/mL, respectively. The inhibitory kinetics, which were analyzed by the Lineweaver-Burk plots, were found to be competitive and noncompetitive inhibitors with a Ki of 1.1 microM and 1.4 mM, respectively.
Kang
Hye Sook
HS
Faculty of Food Science and Biotechnology, Pukyong National University, Busan 608-737, Korea.
Choi
Jin Ho
JH
Cho
Won Ki
WK
Park
Jong Cheol
JC
Choi
Jae Sue
JS
D000107:Acetylation; D001487:Basidiomycota / Q000737:chemistry*; D001547:Benzaldehydes / Q000032:analysis / Q000494:pharmacology; D002396:Catechols / Q000032:analysis / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification; D005650:Fumarates / Q000032:analysis / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D007700:Kinetics; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013107:Sphingolipids / Q000494:pharmacology*; D019802:Succinic Acid / Q000032:analysis / Q000494:pharmacology
D001547:Benzaldehydes; D002396:Catechols; D004791:Enzyme Inhibitors; D005650:Fumarates; D013107:Sphingolipids; C005581:protocatechualdehyde; C032005:fumaric acid; D019802:Succinic Acid; D014442:Monophenol Monooxygenase