Glycosidic Inhibitors of Melanogenesis from Leaves of Passiflora edulis. Issue 10 (16th October 2013)

• Record Type: Journal Article
• Authors: Zhang, Jie; Koike, Ryosuke; Yamamoto, Ayako; Ukiya, Motohiko; Fukatsu, Makoto; Banno, Norihiro; Miura, Motofumi; Motohashi, Shigeyasu; Tokuda, Harukuni; Akihisa, Toshihiro
• Is Part Of: Chemistry & biodiversity. Volume 10:Issue 10(2013:Oct.)
• Page Start: 1851
• Page End: 1865
• Publication Date: 2013-10-16
• Subjects: Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.201300181
• Languages: English
• ISSNs: 1612-1872

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A new flavonoid glycoside, chrysin 6‐<italic>C</italic>‐<italic>β</italic>‐rutinoside (chrysin <italic>α</italic>‐<sc>L</sc>‐rhamnopyranosyl‐(1→6)‐<italic>C</italic>‐<italic>β</italic>‐glucopyranoside; <bold>2</bold>), and two new triterpene glycosides, (31<italic>R</italic>)‐31‐<italic>O</italic>‐methylpassiflorine (<bold>7</bold>) and (31<italic>S</italic>)‐31‐<italic>O</italic>‐methylpassiflorine (<bold>8</bold>), along with 14 known glycosides, including three flavonoid glycosides, <bold>1, 3</bold>, and <bold>4</bold>, six triterpene glycosides, <bold>5, 6</bold>, and <bold>9</bold>–<bold>12</bold>, three cyano glycosides, <bold>13</bold>–<bold>15</bold>, and two other glycosides, <bold>16</bold> and <bold>17</bold>, were isolated from a MeOH extract of the leaves of <italic>Passiflora edulis</italic> (passion flower; Passifloraceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of compounds <bold>1</bold>–<bold>17</bold> against the melanogenesis in the B16 melanoma cells induced with <italic>α</italic>‐melanocyte‐stimulating hormone (<italic>α</italic>‐MSH), three compounds, isoorientin (<bold>1</bold>), <bold>2</bold>, and (6<italic>S</italic>, 9<italic>R</italic>)‐roseoside (<bold>17</bold>), exhibited inhibitory effects with 37.3–47.2% reduction of melanin content with no, or almost no, toxicity to the cells (90.8–100.2% cell viability) at 100 μ<sc>M</sc>. <italic>Western</italic> blot analysis showed that compound <bold>2</bold> reduced the protein levels of MITF, TRP‐1, and tyrosinase, in a concentration‐dependent manner while exerted almost no influence on the level of TRP‐2, suggesting that this compound inhibits melanogenesis on the <italic>α</italic>‐MSH‐stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of TRP‐1 and tyrosinase. In addition, compounds <bold>1</bold>–<bold>17</bold> were evaluated for their inhibitory effects against the <italic>EpsteinBarr</italic> virus early antigen (EBV‐EA) activation induced by 12‐<italic>O</italic>‐tetradecanoylphorbol‐13‐acetate (TPA) in <italic>Raji</italic> cells.</p> </abstract>