53580-61-3Relevant articles and documents
Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit
Manse, Yoshiaki,Ninomiya, Kiyofumi,Nishi, Ryosuke,Kamei, Iyori,Katsuyama, Yushi,Imagawa, Takahito,Chaipech, Saowanee,Muraoka, Osamu,Morikawa, Toshio
, p. 6215 - 6224 (2016/12/06)
An aqueous acetone extract from the fruit of Alpinia galanga (Zingiberaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells (IC50= 7.3 μg/mL). Through bioassay-guided separation of the extract, a new 7-O-9'-linked neolignan, named galanganol D diacetate (1), was isolated along with 16 known compounds including 14 phenylpropanoids (2–15). The structure of 1, including its absolute stereochemistry in the C-7 position, was elucidated by means of extensive NMR analysis and total synthesis. Among the isolates, 1 (IC50= 2.5 μM), 1'S-1'-acetoxychavicol acetate (2, 5.0 μM), and 1'S-1'-acetoxyeugenol acetate (3, 5.6 μM) exhibited a relatively potent inhibitory effect without notable cytotoxicity at effective concentrations. The following structural requirements were suggested to enhance the inhibitory activity of phenylpropanoids on melanogenesis: (i) compounds with 4-acetoxy group exhibit higher activity than those with 4-hydroxy group; (ii) 3-methoxy group dose not affect the activity; (iii) acetylation of the 1'-hydroxy moiety enhances the activity; and (iv) phenylpropanoid dimers with the 7-O-9'-linked neolignan skeleton exhibited higher activity than those with the corresponding monomer. Their respective enantiomers [1' (IC50= 1.9 μM) and 2' (4.5 μM)] and racemic mixtures [(±)-1 (2.2 μM) and (±)-2 (4.4 μM)] were found to exhibit melanogenesis inhibitory activities equivalent to those of the naturally occurring optical active compounds (1 and 2). Furthermore, the active compounds 1–3 inhibited tyrosinase, tyrosine-related protein (TRP)-1, and TRP-2 mRNA expressions, which could be the mechanism of melanogenesis inhibitory activity.
Structure-activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages
Matsuda, Hisashi,Ando, Shin,Morikawa, Toshio,Kataoka, Shinya,Yoshikawa, Masayuki
, p. 1949 - 1953 (2007/10/03)
1′S-1′-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 μM. To clarify the structure-activity relationship of 1′S-1′- acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1′-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2′-3′ double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1′- and 2′-positions reduced the activity.
