A sphingolipid and tyrosinase inhibitors from the fruiting body ofphellinus linteus

Abstract

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.

In Vitro Antioxidant and Anti-Inflammatory Activities of Protocatechualdehyde Isolated from Phellinus gilvus

“…This suggests that PCA may be the major active compound in the Fd fraction that accounts for the majority of the scavenging activity of Fd. PCA had also been isolated from other mushrooms, such as Phellinus linteus ( 9 ), and consistent with our findings, the antioxidant activity of this compound has been documented. For example, PCA isolated from the fruits of greater cardamom ( Amomum subulatum ) had a stronger DPPH scavenging activity than such natural antioxidants as alpha-tocopherol and L -ascorbic acid ( 6 ).…”

Inhibitory Constituents of Aldose Reductase in the Fruiting Body of Phellinus linteus

“…[8][9][10] Interestingly, these mushrooms commonly produce a number of yellow antioxidant pigments that comprise hispidin derivatives and polyphenols. Phellinus linteus, which is commonly referred to as Sangwhang in Korea, has been reported to have strong antioxidant and b-secretase inhibitory activity [11][12][13] as well as apoptotic and anti-complement activity. 14,15) Its known active principals are hispidin, hispolon, and phellinusfurans A and B.…”

An alkaloidal glycoside and other constituents from Leucosceptrum japonicum

“…Previous studies on the chemical constituents of L. japonicum have reported five flavonoids [1] and five acylglycosides [2]. In the present work, a new alkaloidal glycoside (1), a new phenylpropanoid glucoside (2), a new caffeic acid derivative (3), and 26 known compounds, verbascoside (4) [2], acteoside isomer (5) [2], lipedoside A (6) [3], 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-a-L-mannopyranosyl)-4-[(2Z)-3-(4-hydroxyphenyl)-2-propenoate]-b-D-glucopyranoside (7) [4], leucosceptoside A (8) [5], jionoside D (9) [5], martynoside (10) [6], leonoside B (11) [7], scutellarein 7-glucuronide (12) [8], 6-O-methylscutellarin (13) [9], comanthoside B (14) [1], hispidulin 7-O-glucuronide methyl ester (15) [10], hispidulin 7-O-b-D-glucopyranoside (16) [11], luteoline (17) [12], scutellarein (18) [10], 6-O-methyl-scutellarein (19) [10], citrusin C (20) [13], 10-O-(E)-p-coumaroylgeniposidic acid (21) [14], tyrosol (22) [15], protocatechualdehyde (23) [16], p-hydroxybenzoic acid (24) [17], 4-hydroxybenzoic acid methyl ester (25) [18], protocatechuic acid (26) [19], trans-caffeic acid (27) [13], indole-3-aldehyde (28) [20], and indole-3-carboxylic acid (29) [21], were isolated. d 3.08 showed a long-range coupling with a carbon signal at d 109.0 which was long-range coupled with a proton signal at d 7.51.…”