Isolation of tyrosinase inhibitors from Artocarpus heterophyllus and use of its extract as antibrowning agent

Abstract

A new furanoflavone, 7-(2,4-dihydroxyphenyl)-4-hydroxy-2-(2-hydroxy propan-2-yl)-2, 3-dihydrofuro(3, 2-g)chromen-5-one (artocarpfuranol, 1), together with 14 known compounds, dihydromorin (2), steppogenin (3), norartocarpetin (4), artocarpanone (5), artocarpesin (6), artocarpin (7), cycloartocarpin (8), cycloartocarpesin (9), artocarpetin (10), brosimone I (11), cudraflavone B (12), carpachromene (13), isoartocarpesin (14), and cyanomaclurin (15) were isolated from the wood of Artocarpus heterophyllus. Their structures were identified by interpretation of MS,( 1)H-NMR,( 13)C-NMR, HMQC, and HMBC spectroscopic data. Among them, compounds 1-6 and 14 showed strong mushroom tyrosinase inhibitory activity with IC(50) values lower than 50 microM, more potent than kojic acid (IC(50) = 71.6 microM), a well-known tyrosinase inhibitor. In addition, extract of A. heterophyllus was evaluated for its antibrowning effect on fresh-cut apple slices. It was discovered that fresh-cut apple slices treated by dipping in solution of 0.03 or 0.05% of A. heterophyllus extract with 0.5% ascorbic acid did not undergo any substantial browning reaction after storage at room temperature for 24 h. The antibrowning effect was significantly better than samples treated with the extract (0.03 or 0.05%) or ascorbic acid (0.5%) alone. The results provide preliminary evidence supporting the potential of this natural extract as antibrowning agent in food systems.

Skin whitening activity of supercritical fluid extract from spent coffee in B16F10 melanoma cell

“…The inhibition of tyroisnase activity can be accomplished by several mechanism, as follows: First, several polyphenols are accepted as substrates by tyrosinase. It is serves by the same slow-binding and competitive inhibition mode against mushroom tyrosinase (25,26). Second, a long-chain fatty acid inhibited monophenolase and diphenolase of mushroom tyrosinase (27,28).…”

Antibacterial assay-guided isolation of active compounds fromArtocarpus heterophyllusheartwoods

“…In addition, it also possessed some antiplatelet activity (Lin et al, 1996). Cyanomaclurin (4) inhibited mushroom tyrosinase activity with an IC 50 value of 68.7 mM (Zheng et al, 2008). Thus, some of these bioactive flavonoids may be recommended for use as markers for standardization of the extracts of A. heterophyllus heartwoods in a quality control process that might be involved in developing preparations suitable for use as herbal medicines.…”

“…The spectral data were compared with the data in the literature (Likhitwitayawuid et al, 2000;Wang et al, 2004;Zheng et al, 2008).…”

“…A variety of flavonoids and prenylflavonoids have been isolated from this plant (Chung et al, 1995;Lin et al, 1995). Their biological effects have also been reported, including anti-inflammatory (Wei et al, 2005) (Zheng et al, 2008), cytotoxicity (Arung et al, 2010), antiplatelet (Lin et al, 1996), and antibacterial activities .…”

Characterization of Flavonoids in the Ethomedicine Fordiae Cauliflorae Radix and Its Adulterant Millettiae Pulchrae Radix by HPLC-DAD-ESI-IT-TOF-MSn

“…Few pharmacological activities were reported for pachycarin A, 3',4'-dimethoxy[2",3": 7,8]furanoflavone and isoderricin A, even though they have been known for years. However, previous researchers showed that furanoflavones can be used as antibrowning agents [30] and can also have antioxidant and radical quenching activities [31]. Pyranoflavones have antimycobacterial [32] and cytotoxic activities [33], and so on.…”