Piperlonguminine from Piper longum with inhibitory effects on alpha-melanocyte-stimulating hormone-induced melanogenesis in melanoma B16 cells.

Abstract

Skin hyperpigmentations such as melasma, freckles and senile lentigines can be subjectively treated by depigmenting agents. In our ongoing study to find melanogenesis inhibitors from natural sources, Piper longum L (fruits, Piperaceae) was discovered to have an inhibitory effect on alpha-melanocyte-stimulating hormone (alpha-MSH)-induced melanogenesis in melanoma B16 cells. Piperlonguminine has been identified as the melanogenesis inhibitor from P. longum by activity-guided extraction and isolation. The compound showed dose-dependent inhibitory effects with 85.1 +/- 4.9% inhibition at 25 microM, 62.1 +/- 6.1% at 12.5 microM, 36.4 +/- 4.6% at 6.3 microM and 18.4 +/- 5.1% at 3.1 microM on alpha-MSH-induced melanogenesis, showing an IC50 value of 9.6 microM. As a positive control, kojic acid exhibited an IC50 value of 44.6 microM on the melanogenesis. As to the mode of action, piperlonguminine showed an inhibitory effect on alpha-MSH-induced tyrosinase synthesis, documented by Western immunoblot analysis. However, piperlonguminine did not show an inhibitory effect on tyrosinase activity or a direct depigmenting effect of melanin.

• Authors: Kyung Rak Min, Kyeong-Soo Kim, Jai Seup Ro, Seung Ho Lee, Jeong Ah Kim, Jong Keun Son, Youngsoo Kim
• Journal: Planta medica (Planta Med) Vol. 70 Issue 12 Pg. 1115-8 (Dec 2004) ISSN: 0032-0943 [Print] Germany
• PMID: 15643542 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Dioxolanes
• Melanins
• Plant Extracts
• alpha-MSH
• Monophenol Monooxygenase
• piperlonguminine

Topics

• Animals
• Cell Line, Tumor (drug effects)
• Dioxolanes (administration & dosage, pharmacology, therapeutic use)
• Dose-Response Relationship, Drug
• Fruit
• Melanins (biosynthesis)
• Mice
• Monophenol Monooxygenase (biosynthesis)
• Phytotherapy
• Pigmentation Disorders (drug therapy)
• Piper
• Plant Extracts (administration & dosage, pharmacology, therapeutic use)
• alpha-MSH (antagonists & inhibitors, drug effects)