Piperlonguminine from Piper longum with inhibitory effects on alpha-melanocyte-stimulating hormone-induced melanogenesis in melanoma B16 cells.
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.
Min
Kyung Rak
KR
College of Pharmacy and Research Center for Bioresource and Health, Chungbuk National University, Chenogju, Korea.
Kim
Kyeong-Soo
KS
Ro
Jai Seup
JS
Lee
Seung Ho
SH
Kim
Jeong Ah
JA
Son
Jong Keun
JK
Kim
Youngsoo
Y
D000818:Animals; D045744:Cell Line, Tumor / Q000187:drug effects; D004148:Dioxolanes / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D004305:Dose-Response Relationship, Drug; D005638:Fruit; D008543:Melanins / Q000096:biosynthesis; D051379:Mice; D014442:Monophenol Monooxygenase / Q000096:biosynthesis; D008517:Phytotherapy; D010859:Pigmentation Disorders / Q000188:drug therapy; D031701:Piper; D010936:Plant Extracts / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D000521:alpha-MSH / Q000037:antagonists & inhibitors* / Q000187:drug effects*; D010881:Piperidones
D004148:Dioxolanes; D008543:Melanins; D014442:Monophenol Monooxygenase; D010936:Plant Extracts; D000521:alpha-MSH; C498077:piperlongumine; D010881:Piperidones