Suppression of Melanin Synthesis by the Phenolic Constituents of Sappanwood (Caesalpinia sappan)

Kaoru Mitani; Fumihide Takano; Tetsuro Kawabata; Ahmed E. Allam; Mayumi Ota; Tomoya Takahashi; Nobuo Yahagi; Chikai Sakurada; Shinji Fushiya; Tomihisa Ohta

doi:10.1055/s-0032-1327897

Planta Medica, Inhaltsverzeichnis

Planta Med 2013; 79(01): 37-44
DOI: 10.1055/s-0032-1327897

Natural Product Chemistry

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Suppression of Melanin Synthesis by the Phenolic Constituents of Sappanwood (Caesalpinia sappan)

Authors

Kaoru Mitani

¹Pharmacognosy and Chemistry of Natural Products, School of Pharmacy and Pharmaceutical Sciences, Kanazawa University, Kanazawa, Japan
Fumihide Takano

¹Pharmacognosy and Chemistry of Natural Products, School of Pharmacy and Pharmaceutical Sciences, Kanazawa University, Kanazawa, Japan

²Nihon Pharmaceutical University, Saitama, Japan
Tetsuro Kawabata

¹Pharmacognosy and Chemistry of Natural Products, School of Pharmacy and Pharmaceutical Sciences, Kanazawa University, Kanazawa, Japan
Ahmed E. Allam

¹Pharmacognosy and Chemistry of Natural Products, School of Pharmacy and Pharmaceutical Sciences, Kanazawa University, Kanazawa, Japan
Mayumi Ota

¹Pharmacognosy and Chemistry of Natural Products, School of Pharmacy and Pharmaceutical Sciences, Kanazawa University, Kanazawa, Japan
Tomoya Takahashi

¹Pharmacognosy and Chemistry of Natural Products, School of Pharmacy and Pharmaceutical Sciences, Kanazawa University, Kanazawa, Japan
Nobuo Yahagi

¹Pharmacognosy and Chemistry of Natural Products, School of Pharmacy and Pharmaceutical Sciences, Kanazawa University, Kanazawa, Japan
Chikai Sakurada

²Nihon Pharmaceutical University, Saitama, Japan
Shinji Fushiya

²Nihon Pharmaceutical University, Saitama, Japan
Tomihisa Ohta

¹Pharmacognosy and Chemistry of Natural Products, School of Pharmacy and Pharmaceutical Sciences, Kanazawa University, Kanazawa, Japan

Abstract

Sappanwood (Caesalpinia sappan Linn.) is used as an herbal medicine. It is sometimes used to treat skin damage or as a facial cleanser. In the present study, the methanol (MeOH) extract of sappanwood was found to inhibit melanin synthesis in cultured human melanoma HMV-II cells stimulated with forskolin, and six active compounds (1–5 and 7) were isolated from the extract along with a non-active compound (6). Compounds 2–7 were identified as sappanchalcone (2), 3′-deoxy-4-O-methylsappanol (3), brazilein, (4), brazilin (5), sappanol (6), and 4-O-methylsappanol (7). Compound 1 was a new compound, and its structure was determined to be (6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,6a,10,11-tetrol by spectroscopic analyses. Among the six active compounds, brazilin (5) (EC₅₀: 3.0 ± 0.5 µM) and 4-O-methylsappanol (7) (EC₅₀: 4.6 ± 0.7 µM) strongly suppressed melanin synthesis in HMV-II cells. Bioactive compounds showed moderate cytotoxicities against HMV-II cells with IC₅₀ values of 83.1 ± 4.0 µM (for 2), 72.0 µM ± 2.4 (for 3), 33.8 ± 1.1 µM (for 4), 18.4 ± 0.8 µM (for 5), and 20.2 ± 0.8 (for 7), respectively. Brazilin (5) selectively suppressed the expression of mRNAs for tyrosinase-related protein (TYRP) 2 and tyrosinase but did not influence the expression of TYRP1. These results suggest that brazilin (5) is a new class of melanin inhibitor and that sappanwood could be used as a cosmetic material.

Key words

Caesalpinia sappan Linn. - Fabaceae - antimelanogenesis - brazilin - mRNAs expression

Volltext

Referenzen

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