Inhibitors of melanogenesis in B16 melanoma 4A5 cells from flower buds of Lawsonia inermis (Henna)

Souichi Nakashima; Yoshimi Oda; Seikou Nakamura; Jiang Liu; Koko Onishi; Miki Kawabata; Hisako Miki; Yugo Himuro; Masayuki Yoshikawa; Hisashi Matsuda

doi:10.1016/j.bmcl.2015.04.052

Inhibitors of melanogenesis in B16 melanoma 4A5 cells from flower buds of Lawsonia inermis (Henna)

Bioorg Med Chem Lett. 2015 Jul 1;25(13):2702-6. doi: 10.1016/j.bmcl.2015.04.052. Epub 2015 Apr 22.

Authors

Affiliations

¹ Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan; N. T. H Co., Ltd, 1-8-11 4F Sky-ebisu Bldg., Ebisu, Shibuya-ku, Tokyo 150-0013, Japan. Electronic address: nakashima@nthhenna.co.jp.
² Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan; N. T. H Co., Ltd, 1-8-11 4F Sky-ebisu Bldg., Ebisu, Shibuya-ku, Tokyo 150-0013, Japan.
³ Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan.

PMID: 25987378
DOI: 10.1016/j.bmcl.2015.04.052

Abstract

The methanolic extract of Lawsonia inermis L. (henna) showed significant inhibitory activity toward melanogenesis in B16 melanoma 4A5 cells. Among the constituents isolated from the methanolic extract, luteolin, quercetin, and (±)-eriodictyol showed stronger inhibitory activity than the reference compound, arbutin. Several structure-activity relationships of the flavonoids were suggested, and OGlc<H=OH at the 3-position, OGlc<OH at the 4'-position, and the double bond between the 2- and 3-positions were important. The active constituents suppressed tyrosinase, tyrosinase related protein (TRP)-1, and TRP-2 mRNA expression. The suppression was considered as one of the mechanisms of action. Furthermore, the methanolic extract and several constituents, including luteoloside and spiraeoside, showed anti-plasmin activity, which is considered to play a key role in UV-stimulated melanogenesis in human skin.

Keywords: Anti-melanogenic activity; Ayurvedic plant; Henna; Lawsonia inermis; Plasmin.

MeSH terms

Animals
Antifibrinolytic Agents / chemistry
Antifibrinolytic Agents / isolation & purification
Antifibrinolytic Agents / pharmacology
Cell Line, Tumor
Cell Proliferation / drug effects
Flavonoids / chemistry*
Flavonoids / isolation & purification
Flavonoids / pharmacology*
Flowers / chemistry
Humans
Intramolecular Oxidoreductases / antagonists & inhibitors
Intramolecular Oxidoreductases / genetics
Lawsonia Plant / chemistry*
Melanins / biosynthesis*
Melanoma, Experimental / drug therapy*
Melanoma, Experimental / genetics
Melanoma, Experimental / metabolism*
Mice
Monophenol Monooxygenase / antagonists & inhibitors
Monophenol Monooxygenase / genetics
Oxidoreductases / antagonists & inhibitors
Oxidoreductases / genetics
Plant Extracts / chemistry
Plant Extracts / isolation & purification
Plant Extracts / pharmacology
Plants, Medicinal / chemistry
RNA, Messenger / genetics
RNA, Messenger / metabolism
RNA, Neoplasm / genetics
RNA, Neoplasm / metabolism
Structure-Activity Relationship

Substances

Antifibrinolytic Agents
Flavonoids
Melanins
Plant Extracts
RNA, Messenger
RNA, Neoplasm
Oxidoreductases
tyrosinase-related protein-1
Monophenol Monooxygenase
Intramolecular Oxidoreductases
dopachrome isomerase