Labdane-Type Diterpenes, Galangalditerpenes A–C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga

In our continuing study of biologically active natural products from the fruit of Alpinia galanga (Zingiberaceae), we newly isolated three new labdane-type diterpenes, termed galangalditerpenes A–C (1–3), along with four known sesquiterpenes (4–7) and two diterpenes (8 and 9). The stereostructures o...

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Autores principales: Manse, Yoshiaki, Ninomiya, Kiyofumi, Nishi, Ryosuke, Hashimoto, Yoshinori, Chaipech, Saowanee, Muraoka, Osamu, Morikawa, Toshio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6149739/
https://www.ncbi.nlm.nih.gov/pubmed/29261124
http://dx.doi.org/10.3390/molecules22122279
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author Manse, Yoshiaki
Ninomiya, Kiyofumi
Nishi, Ryosuke
Hashimoto, Yoshinori
Chaipech, Saowanee
Muraoka, Osamu
Morikawa, Toshio
author_facet Manse, Yoshiaki
Ninomiya, Kiyofumi
Nishi, Ryosuke
Hashimoto, Yoshinori
Chaipech, Saowanee
Muraoka, Osamu
Morikawa, Toshio
author_sort Manse, Yoshiaki
collection PubMed
description In our continuing study of biologically active natural products from the fruit of Alpinia galanga (Zingiberaceae), we newly isolated three new labdane-type diterpenes, termed galangalditerpenes A–C (1–3), along with four known sesquiterpenes (4–7) and two diterpenes (8 and 9). The stereostructures of 1–3 were elucidated on the basis of their spectroscopic properties. The melanogenesis inhibitory activities in theophylline-stimulated murine B16 melanoma 4A5 cells of these isolates, including the new diterpenes (1–3, IC(50) = 4.4, 8.6, and 4.6 μM, respectively), were found to be more than 6–87-fold higher than that of arbutin (174 μM), a commercially available positive control.
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spelling pubmed-61497392018-11-13 Labdane-Type Diterpenes, Galangalditerpenes A–C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga Manse, Yoshiaki Ninomiya, Kiyofumi Nishi, Ryosuke Hashimoto, Yoshinori Chaipech, Saowanee Muraoka, Osamu Morikawa, Toshio Molecules Article In our continuing study of biologically active natural products from the fruit of Alpinia galanga (Zingiberaceae), we newly isolated three new labdane-type diterpenes, termed galangalditerpenes A–C (1–3), along with four known sesquiterpenes (4–7) and two diterpenes (8 and 9). The stereostructures of 1–3 were elucidated on the basis of their spectroscopic properties. The melanogenesis inhibitory activities in theophylline-stimulated murine B16 melanoma 4A5 cells of these isolates, including the new diterpenes (1–3, IC(50) = 4.4, 8.6, and 4.6 μM, respectively), were found to be more than 6–87-fold higher than that of arbutin (174 μM), a commercially available positive control. MDPI 2017-12-20 /pmc/articles/PMC6149739/ /pubmed/29261124 http://dx.doi.org/10.3390/molecules22122279 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Manse, Yoshiaki
Ninomiya, Kiyofumi
Nishi, Ryosuke
Hashimoto, Yoshinori
Chaipech, Saowanee
Muraoka, Osamu
Morikawa, Toshio
Labdane-Type Diterpenes, Galangalditerpenes A–C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga
title Labdane-Type Diterpenes, Galangalditerpenes A–C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga
title_full Labdane-Type Diterpenes, Galangalditerpenes A–C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga
title_fullStr Labdane-Type Diterpenes, Galangalditerpenes A–C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga
title_full_unstemmed Labdane-Type Diterpenes, Galangalditerpenes A–C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga
title_short Labdane-Type Diterpenes, Galangalditerpenes A–C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga
title_sort labdane-type diterpenes, galangalditerpenes a–c, with melanogenesis inhibitory activity from the fruit of alpinia galanga
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6149739/
https://www.ncbi.nlm.nih.gov/pubmed/29261124
http://dx.doi.org/10.3390/molecules22122279
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