2. Academic Validation
  3. Flavokawains B and C, melanogenesis inhibitors, isolated from the root of Piper methysticum and synthesis of analogs

Flavokawains B and C, melanogenesis inhibitors, isolated from the root of Piper methysticum and synthesis of analogs

  • Bioorg Med Chem Lett. 2015 Feb 15;25(4):799-802. doi: 10.1016/j.bmcl.2014.12.082.
Hye-Jin Jeong 1,  Chang Seok Lee 2,  Janggyoo Choi 3,  Yong Deog Hong 2,  Song Seok Shin 2,  Jun Seong Park 2,  John Hwan Lee 2,  Seokyong Lee 4,  Kee Dong Yoon 5,  Jaeyoung Ko 6
Affiliations

Affiliations

  • 1 Development Group for Global New Drug Developing Human Resources (BK21 Plus Project), Republic of Korea; School of Pharmacy, Sungkyunkwan University, Suwan, Gyeonggi-do 440-746, Republic of Korea.
  • 2 Amorepacific R&D Unit, 314-1 Bora-dong, Giheung-gu, Yongin-si, Gyeonggi-do 449-729, Republic of Korea.
  • 3 College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University, Seoul, Republic of Korea.
  • 4 School of Pharmacy, Sungkyunkwan University, Suwan, Gyeonggi-do 440-746, Republic of Korea.
  • 5 College of Pharmacy and Integrated Research Institute of Pharmaceutical Sciences, The Catholic University of Korea, Bucheon-si, Republic of Korea. Electronic address: kdyoon@catholic.ac.kr.
  • 6 Amorepacific R&D Unit, 314-1 Bora-dong, Giheung-gu, Yongin-si, Gyeonggi-do 449-729, Republic of Korea. Electronic address: jaeyoungko@amorepacific.com.
PMID: 25597012 DOI: 10.1016/j.bmcl.2014.12.082
Abstract

The ethanolic extract of the root of Piper methysticum was found to inhibit melanogenesis in MSH-activated B16 melanoma cells. Flavokawains B and C were isolated from this extract based on their anti-melanogenesis activity and found to inhibit melanogenesis with IC50 values of 7.7μM and 6.9μM, respectively. Flavokawain analogs were synthesized through a Claisen-Schmidt condensation of their corresponding acetophenones and benzaldehydes and were evaluated in terms of their Tyrosinase inhibitory and anti-melanogenesis activities. Compound 1b was the most potent of these with an IC50 value of 2.3μM in melanogenesis inhibition assays using MSH-activated B16 melanoma cells.

Keywords

Chalcones; Flavokawain B and C; Melanogenesis; Piper methysticum.

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