title: Flavokawains B and C, melanogenesis inhibitors, isolated from the root of Piper methysticum and synthesis of analogs.
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.
authors.affiliation: 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.
authors.forename: Hye-Jin
authors.initials: HJ
authors.lastname: Jeong
authors.affiliation: Amorepacific R&D Unit, 314-1 Bora-dong, Giheung-gu, Yongin-si, Gyeonggi-do 449-729, Republic of Korea.
authors.forename: Chang Seok
authors.initials: CS
authors.lastname: Lee
authors.affiliation: College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University, Seoul, Republic of Korea.
authors.forename: Janggyoo
authors.initials: J
authors.lastname: Choi
authors.affiliation: Amorepacific R&D Unit, 314-1 Bora-dong, Giheung-gu, Yongin-si, Gyeonggi-do 449-729, Republic of Korea.
authors.forename: Yong Deog
authors.initials: YD
authors.lastname: Hong
authors.affiliation: Amorepacific R&D Unit, 314-1 Bora-dong, Giheung-gu, Yongin-si, Gyeonggi-do 449-729, Republic of Korea.
authors.forename: Song Seok
authors.initials: SS
authors.lastname: Shin
authors.affiliation: Amorepacific R&D Unit, 314-1 Bora-dong, Giheung-gu, Yongin-si, Gyeonggi-do 449-729, Republic of Korea.
authors.forename: Jun Seong
authors.initials: JS
authors.lastname: Park
authors.affiliation: Amorepacific R&D Unit, 314-1 Bora-dong, Giheung-gu, Yongin-si, Gyeonggi-do 449-729, Republic of Korea.
authors.forename: John Hwan
authors.initials: JH
authors.lastname: Lee
authors.affiliation: School of Pharmacy, Sungkyunkwan University, Suwan, Gyeonggi-do 440-746, Republic of Korea.
authors.forename: Seokyong
authors.initials: S
authors.lastname: Lee
authors.affiliation: 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.
authors.forename: Kee Dong
authors.initials: KD
authors.lastname: Yoon
authors.affiliation: Amorepacific R&D Unit, 314-1 Bora-dong, Giheung-gu, Yongin-si, Gyeonggi-do 449-729, Republic of Korea. Electronic address: jaeyoungko@amorepacific.com.
authors.forename: Jaeyoung
authors.initials: J
authors.lastname: Ko
mesh_terms: D000818:Animals; D005419:Flavonoids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D020901:Kava / Q000737:chemistry*; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000096:biosynthesis / Q000138:chemical synthesis; D008546:Melanoma, Experimental / Q000188:drug therapy; D051379:Mice; D013329:Structure-Activity Relationship
chemical_list: D005419:Flavonoids; D008543:Melanins; C452039:flavokawain B
keywords: Chalcones; Flavokawain B and C; Melanogenesis; Piper methysticum