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

Yoshiaki Manse; Kiyofumi Ninomiya; Ryosuke Nishi; Yoshinori Hashimoto; Saowanee Chaipech; Osamu Muraoka; Toshio Morikawa

doi:10.3390/molecules22122279

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

Molecules. 2017 Dec 20;22(12):2279. doi: 10.3390/molecules22122279.

Authors

Yoshiaki Manse¹, Kiyofumi Ninomiya^{2

3}, Ryosuke Nishi⁴, Yoshinori Hashimoto⁵, Saowanee Chaipech^{6

7}, Osamu Muraoka^{8

9}, Toshio Morikawa^{10

11}

Affiliations

¹ Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. yoshiaki4849sa735@gmail.com.
² Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. ninomiya@phar.kindai.ac.jp.
³ Antiaging Center, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. ninomiya@phar.kindai.ac.jp.
⁴ Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. kojirou922@gmail.com.
⁵ Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. yoshinorihashimoto0608@gmail.com.
⁶ Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. chaipechann@hotmail.com.
⁷ Faculty of Agro-Industry, Rajamangala University of Technology Srivijaya, Thungyai, Nakhon Si Thammarat 80240, Thailand. chaipechann@hotmail.com.
⁸ Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. muraoka@phar.kindai.ac.jp.
⁹ Antiaging Center, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. muraoka@phar.kindai.ac.jp.
¹⁰ Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. morikawa@kindai.ac.jp.
¹¹ Antiaging Center, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. morikawa@kindai.ac.jp.

Abstract

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, IC₅₀ = 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.

Keywords: Alpinia galanga; galangaldeterpene; labdane-type diterpene; melanogenesis inhibitor.

MeSH terms

Alpinia / chemistry*
Animals
Arbutin / chemistry
Arbutin / pharmacology
Cell Line, Tumor
Cell Survival / drug effects
Diterpenes / chemistry*
Diterpenes / isolation & purification
Diterpenes / pharmacology
Fruit / chemistry*
Melanins / metabolism*
Melanoma, Experimental
Mice
Molecular Conformation
Plant Extracts / chemistry
Plant Extracts / isolation & purification
Plant Extracts / pharmacology
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification
Sesquiterpenes / pharmacology
Structure-Activity Relationship

Substances

Diterpenes
Melanins
Plant Extracts
Sesquiterpenes
Arbutin