Antioxidant Compounds, Kirenol and Methyl ent-16α, 17-dihydroxy-kauran-19-oate Bioactivity-Guided Isolated from Siegesbeckia glabrescens Attenuates MITF-Mediated Melanogenesis via Inhibition of Intracellular ROS Production

(Compositae), an annual herb indigenous to Korean mountainous regions and has been eaten as a food in Korea. This study investigated ABTS, DPPH and nitric oxide (NO) radical-scavenging activities, and melanin production and TYR inhibitory effects-guided fractionation to identify therapeutic phytoche...

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Published in:	Molecules (Basel, Switzerland) Vol. 26; no. 7; p. 1940
Main Authors:	Shim, Sun-Yup, Lee, Ye Eun, Lee, Mina
Format:	Journal Article
Language:	English
Published:	Switzerland MDPI AG 30-03-2021 MDPI
Subjects:	Acids Antioxidants Biological activity Butyl hydroperoxide Cytotoxicity Ethanol Fractionation Functional materials Homeostasis Hyperpigmentation Intracellular Kinases kirenol Melanin Melanoma methyl ent-16α, 17-dihydroxy-kauran-19-oate Microphthalmia-associated transcription factor Nitric oxide Oxidation Oxidation resistance Oxidative stress Phytochemicals Proteins reactive oxygen species Scavenging Siegesbeckia glabrescens Skin cancer Tyrosinase Siegesbeckia glabrescens microphthalmia-associated transcription factor methyl ent-16α, 17-dihydroxy-kauran-19-oate melanin kirenol reactive oxygen species
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Abstract	(Compositae), an annual herb indigenous to Korean mountainous regions and has been eaten as a food in Korea. This study investigated ABTS, DPPH and nitric oxide (NO) radical-scavenging activities, and melanin production and TYR inhibitory effects-guided fractionation to identify therapeutic phytochemicals from that can attenuate oxidation and melanogenesis in murine melanoma B16F10 cells. Nine compounds with inhibitory effects on melanin production, and TYR activity, and ABTS, DPPH, and NO radical scavenging activity were isolated from the 100% ethanol fraction from . Among the nine compounds, kirenol (K), methyl ent-16α, 17-dihydroxy-kauran-19-oate (MDK) had strong inhibitory effects on melanin production and TYR activity with antioxidant effects. Western blot analysis revealed that K and MDK suppressed tyrosinase-related protein (TYRP)-1, TYRP-2 and microphthalmia-associated transcription factor (MITF) expression. Moreover, these two compounds inhibited intracellular reactive oxygen species (ROS) level in tert-butyl hydroperoxide ( -BHP)-treated B16F10 cells. Our results suggest that containing active compounds such as K and MDK, which has antioxidant and antimelanogenesis effects, is the potent therapeutic and functional material for the prevention of oxidation-induced hyperpigmentation.
AbstractList	Siegesbeckia glabrescens (Compositae), an annual herb indigenous to Korean mountainous regions and has been eaten as a food in Korea. This study investigated ABTS, DPPH and nitric oxide (NO) radical-scavenging activities, and melanin production and TYR inhibitory effects-guided fractionation to identify therapeutic phytochemicals from S. glabrescens that can attenuate oxidation and melanogenesis in murine melanoma B16F10 cells. Nine compounds with inhibitory effects on melanin production, and TYR activity, and ABTS, DPPH, and NO radical scavenging activity were isolated from the 100% ethanol fraction from S. glabrescens . Among the nine compounds, kirenol (K), methyl ent-16α, 17-dihydroxy-kauran-19-oate (MDK) had strong inhibitory effects on melanin production and TYR activity with antioxidant effects. Western blot analysis revealed that K and MDK suppressed tyrosinase-related protein (TYRP)-1, TYRP-2 and microphthalmia-associated transcription factor (MITF) expression. Moreover, these two compounds inhibited intracellular reactive oxygen species (ROS) level in tert-butyl hydroperoxide ( t -BHP)-treated B16F10 cells. Our results suggest that S. glabrescens containing active compounds such as K and MDK, which has antioxidant and antimelanogenesis effects, is the potent therapeutic and functional material for the prevention of oxidation-induced hyperpigmentation. Siegesbeckia glabrescens (Compositae), an annual herb indigenous to Korean mountainous regions and has been eaten as a food in Korea. This study investigated ABTS, DPPH and nitric oxide (NO) radical-scavenging activities, and melanin production and TYR inhibitory effects-guided fractionation to identify therapeutic phytochemicals from S. glabrescens that can attenuate oxidation and melanogenesis in murine melanoma B16F10 cells. Nine compounds with inhibitory effects on melanin production, and TYR activity, and ABTS, DPPH, and NO radical scavenging activity were isolated from the 100% ethanol fraction from S. glabrescens. Among the nine compounds, kirenol (K), methyl ent-16α, 17-dihydroxy-kauran-19-oate (MDK) had strong inhibitory effects on melanin production and TYR activity with antioxidant effects. Western blot analysis revealed that K and MDK suppressed tyrosinase-related protein (TYRP)-1, TYRP-2 and microphthalmia-associated transcription factor (MITF) expression. Moreover, these two compounds inhibited intracellular reactive oxygen species (ROS) level in tert-butyl hydroperoxide (t-BHP)-treated B16F10 cells. Our results suggest that S. glabrescens containing active compounds such as K and MDK, which has antioxidant and antimelanogenesis effects, is the potent therapeutic and functional material for the prevention of oxidation-induced hyperpigmentation. (Compositae), an annual herb indigenous to Korean mountainous regions and has been eaten as a food in Korea. This study investigated ABTS, DPPH and nitric oxide (NO) radical-scavenging activities, and melanin production and TYR inhibitory effects-guided fractionation to identify therapeutic phytochemicals from that can attenuate oxidation and melanogenesis in murine melanoma B16F10 cells. Nine compounds with inhibitory effects on melanin production, and TYR activity, and ABTS, DPPH, and NO radical scavenging activity were isolated from the 100% ethanol fraction from . Among the nine compounds, kirenol (K), methyl ent-16α, 17-dihydroxy-kauran-19-oate (MDK) had strong inhibitory effects on melanin production and TYR activity with antioxidant effects. Western blot analysis revealed that K and MDK suppressed tyrosinase-related protein (TYRP)-1, TYRP-2 and microphthalmia-associated transcription factor (MITF) expression. Moreover, these two compounds inhibited intracellular reactive oxygen species (ROS) level in tert-butyl hydroperoxide ( -BHP)-treated B16F10 cells. Our results suggest that containing active compounds such as K and MDK, which has antioxidant and antimelanogenesis effects, is the potent therapeutic and functional material for the prevention of oxidation-induced hyperpigmentation.
Author	Lee, Ye Eun Lee, Mina Shim, Sun-Yup
AuthorAffiliation	2 College of Pharmacy and Research Institute of Life and Pharmaceutical Sciences, Sunchon National University, 255 Jungangno, Suncheon-si 57922, Korea; qjsro1124@naver.com 3 Institute of Jinan Red Ginseng, 41 Hongsamhanbang-Ro, Jinan-Eup, Jinan-Gun 55442, Korea 1 Department of Food Science and Biotechnology, Sunchon National University, 255 Jungangno, Suncheon-si 57922, Korea; shimsy@scnu.ac.kr
AuthorAffiliation_xml	– name: 3 Institute of Jinan Red Ginseng, 41 Hongsamhanbang-Ro, Jinan-Eup, Jinan-Gun 55442, Korea – name: 2 College of Pharmacy and Research Institute of Life and Pharmaceutical Sciences, Sunchon National University, 255 Jungangno, Suncheon-si 57922, Korea; qjsro1124@naver.com – name: 1 Department of Food Science and Biotechnology, Sunchon National University, 255 Jungangno, Suncheon-si 57922, Korea; shimsy@scnu.ac.kr
Author_xml	– sequence: 1 givenname: Sun-Yup surname: Shim fullname: Shim, Sun-Yup organization: Department of Food Science and Biotechnology, Sunchon National University, 255 Jungangno, Suncheon-si 57922, Korea – sequence: 2 givenname: Ye Eun surname: Lee fullname: Lee, Ye Eun organization: Institute of Jinan Red Ginseng, 41 Hongsamhanbang-Ro, Jinan-Eup, Jinan-Gun 55442, Korea – sequence: 3 givenname: Mina surname: Lee fullname: Lee, Mina organization: College of Pharmacy and Research Institute of Life and Pharmaceutical Sciences, Sunchon National University, 255 Jungangno, Suncheon-si 57922, Korea
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Keywords	Siegesbeckia glabrescens microphthalmia-associated transcription factor methyl ent-16α, 17-dihydroxy-kauran-19-oate melanin kirenol reactive oxygen species
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Snippet	(Compositae), an annual herb indigenous to Korean mountainous regions and has been eaten as a food in Korea. This study investigated ABTS, DPPH and nitric... Siegesbeckia glabrescens (Compositae), an annual herb indigenous to Korean mountainous regions and has been eaten as a food in Korea. This study investigated... Siegesbeckia glabrescens (Compositae), an annual herb indigenous to Korean mountainous regions and has been eaten as a food in Korea. This study investigated...
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SubjectTerms	Acids Antioxidants Biological activity Butyl hydroperoxide Cytotoxicity Ethanol Fractionation Functional materials Homeostasis Hyperpigmentation Intracellular Kinases kirenol Melanin Melanoma methyl ent-16α, 17-dihydroxy-kauran-19-oate Microphthalmia-associated transcription factor Nitric oxide Oxidation Oxidation resistance Oxidative stress Phytochemicals Proteins reactive oxygen species Scavenging Siegesbeckia glabrescens Skin cancer Tyrosinase
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Title	Antioxidant Compounds, Kirenol and Methyl ent-16α, 17-dihydroxy-kauran-19-oate Bioactivity-Guided Isolated from Siegesbeckia glabrescens Attenuates MITF-Mediated Melanogenesis via Inhibition of Intracellular ROS Production
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