Melanin Synthesis Inhibitors from Balanophora fungosa

Abstract

Tyrosinase, trypsin, and tryptase are known to play important roles in melanin production of human skin. This paper describes the study of the inhibitory effect of Balanophora fungosa on melanin. The 50% EtOH extract obtained from B. fungosa indicated an inhibitory effect on mushroom tyrosinase activity with an IC(50) value of 15 μg/mL. Bioassay-guided fractionation of the active extract resulted in the isolation of four known compounds. Their structures were identified as 1-O-(E)-caffeoyl-3-O-galloyl-4,6-(S)-HHDP-β-d-glucopyranose (1), 1-O-(E)-caffeoyl-3,4,6-tri-O-galloyl-β-d-glucopyranose (2), caffeoyl-β-d-glucopyranose (3), and abietin (4) on the basis of spectroscopic analyses and comparison of their spectral data with those in the literature. Compounds 1 and 2 prevented pigmentation of melanin in a three-dimensional cultured human skin model. Furthermore, compounds 1 and 2 indicated inhibitory activities against trypsin and tryptase.

Isolation and Antibacterial Properties of Phenyl Acrylic Acid Derivatives from Balanophora elongata Blume

“…Balanophorin has been recorded as a secondary metabolite originated from B. elongata [4]. Bioactivity studies have revealed that isolated compounds of Balanophora species showed antioxidant activity [5]; anti-radical scavenging properties [6][7]; α-glucosidase inhibition [8][9]; cytotoxic toward cancer cell lines, including breast (MCF7), liver (HepG2), lung (SK-LU-1), and epidermal (KB) cancer [5]; xanthine-oxidase inhibition [10]; trypsin and tryptase inhibition [11]; vasodilator [12]; and HIV-1 Env Pseudovirus inhibition [13][14].…”

Phytochemicals and biological studies of plants from the genus Balanophora

“…[1,3,6,8-10]. Aside from those, the galloyl, HHDP and their derivatives linking the glucosyl unit at C(1), C(3), C(4) and / or C(6) positions through ester bonds are major constituents in the genus Balanophora [1,2,11-18]. …”

“…As for the HHDP groups, it was mostly joint to C(4) and C(6) [1,5,7,14,16-18]. Compounds 28–30, isolated from the plants B .…”

“…Balapolyphorins A (35) was also cinnamic acid derivative tannin with a balapolyphoroyl group at C(6) position in glucosyl unit to form aryl ester and a caffeoyl group to the C(1) by acyl O -glycosidic linkage [15]. Compounds 36–41 take the characteristics that a coumaroyl or cinnamoyl is connected to anomeric carbon by O -glycosidic bond, and several galloyl and HHDP groups are linked with the C(3), C(4) and / or C(6) positions in glucosyl moiety to form sugar aryl ester linkages [1,5,14,16-18]. …”

Diversion of the melanin synthetic pathway by dopamine product scavengers: A quantum chemical modeling of the reaction mechanisms

“…The inhibition of the synthesis of melanin using Lespedeza cyrtobotrya [11], Lespedeza floribunda and Balanophora fungosa [12] atoms before and after the formation of new bonds during the chemical reactions. The reactants as well as products have been assessed based on the potential energy surfaces (PES) and the geometry corresponding to the global minimum of the PES was considered for further calculations for each molecule.…”