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Sesquiterpenoids from <i>Seriphidium transiliense</i> and Their Melanogenic Activity

J. F. WuState Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization and Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, People’s Republic of ChinaAblajan TurakState Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization and Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, People’s Republic of ChinaDeng ZangState Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization and Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, People’s Republic of ChinaGuo‐An ZouState Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization and Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, People’s Republic of ChinaHaji Akber AisaState Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization and Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, People’s Republic of China

2022en

ABI

Annotatsiya

A sesquiterpenoid with an unprecedented 5/5/4 tricyclic skeleton (1), a nor-sesquiterpenoid with a rare 6/7 bicyclic skeleton (2), 10 new sesquiterpenoids (3–12), and six known analogues (13–18) were isolated from the whole plants of Seriphidium transiliense. The structures of compounds 1–12 were elucidated by spectroscopic data analysis. Compound 7 showed melanogenic promotion activity in murine melanoma (B16) cells more potent than the positive control used, 8-methoxypsoralen (8-MOP). Further mechanistic studies indicated that compound 7 promotes melanogenesis through activating the transcription of microphthalmia-associated transcription factor (MITF) and tyrosinase family genes in B16 cells. Moreover, compound 7 also inhibited the expression of IFN-γ-chemokine through the JAK/STAT signaling pathway in immortalized human keratinocyte (HaCaT) cells. These results suggest that the sesquiterpenoid 7 shows potential activity for treating vitiligo.

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Identifikatorlar

DOI: 10.1021/acs.jnatprod.2c00527

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