Triterpenoids fromFragaria ananassacalyx and their inhibitory effects on melanogenesis in B16-F10 mouse melanoma cells

Abstract

Column chromatographic technology was applied to isolate six purified ursane triterpenoids from the calyx of Fragaria ananassa and they were identified on the basis of spectroscopic methods to be ursolic acid (1), pomolic acid (2), 2-oxo-pomolic acid (3), 3-O-acetyl pomolic acid (4), fupenzic acid (5) and euscaphic acid (6). This is the first study in which these compounds have been isolated from the calyx of F. ananassa. Compared to a well-known inhibitor, α-arbutin, compounds 2-6 showed a significant decrease in intracellular melanin content in B16-F10 cells, and in culture media melanin.

p-Hydroxybenzoic Acid beta-D-Glucosyl Ester and Cimidahurinine with Antimelanogenesis and Antioxidant Effects from Pyracantha angustifolia via Bioactivity-Guided Fractionation

“…Considerable efforts have been made to develop products that reduce melanin synthesis for use as whitening constituents [33][34][35][36][37][38]. TYR is an oxidase that is the rate-limiting enzyme for controlling the production of melanin.…”

“…Fifteen compounds, four compounds from CHCl3 fraction, one compounds from EtOAc fraction, and ten compounds from n-butanol fraction, were isolated and chemical structure was identified (Figure 4). Among the fifteen phytochemicals, the anti-melanogenesis effects of the compounds are reported elsewhere, as representative whitening materials [33][34][35][36][37][38]. Seven compounds isolated from n-butanol fraction were assessed in the present study.…”

“…Among the fifteen phytochemicals, the anti-melanogenesis effects of compounds 1-3, 5-7, 9, and 11 are reported elsewhere. In particular, arbutin, a representative whitening material, was used as a positive control in this study [33][34][35][36][37][38]. Except for these compounds, seven compounds isolated from the n-butanol fraction were assessed for their anti-melanogenesis and anti-oxidant effects.…”

Biotransformation of Oleanane and Ursane Triterpenic Acids

“…The ethyl acetate fraction of Potentilla fulgens root extract containing ursane triterpenoids showed antioxidant activity by inhibiting the production of free radicals [58]. An alcohol extract and ethyl acetate fraction of Fragaria ananassa perianth containing various triterpenoids had a pronounced cytotoxic effect on B16-F10 melanoma cells and inhibited their melanogenesis by 79.1% and 80.2%, respectively [4]. The allelopathic effect (inhibition of seed maturation and root growth of nearby plants) of Alstonia scholaris was also due to high UA content (2.5 ± 0.6 mg/g dry weight of leaves) [49].…”

“…Naturally occurring triterpenoids are represented by more than 100 various types of skeletons [2]. Native triterpenoids, in particular, oleanane and ursane representatives, are of interest for researchers due to their availability and multiple biological activities, including antimicrobial, anti-inflammatory, antitumor, cytotoxic, hepatoprotective, and other activities [3][4][5][6][7]. Triterpenic molecules, however, are highly hydrophobic which significantly limits their use as effective pharmacological agents.…”