Kaemgalangol A: Unusual seco-isopimarane diterpenoid from aromatic ginger Kaempferia galanga

Ningombam Swapana; Takehiro Tominaga; Abdelsamed I Elshamy; Mahmoud A A Ibrahim; Mohamed-Elamir F Hegazy; Ch Brajakishor Singh; Midori Suenaga; Hiroshi Imagawa; Masaaki Noji; Akemi Umeyama

doi:10.1016/j.fitote.2018.06.010

Kaemgalangol A: Unusual seco-isopimarane diterpenoid from aromatic ginger Kaempferia galanga

Fitoterapia. 2018 Sep:129:47-53. doi: 10.1016/j.fitote.2018.06.010. Epub 2018 Jun 18.

Affiliations

¹ Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan; S. Kula Women's College, India.
² Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
³ Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan; Department of Natural Compounds Chemistry, National Research Centre, 33 El Bohouth St., Dokki, Giza 12622, Egypt. Electronic address: elshamynrc@yahoo.com.
⁴ Computational Chemistry Laboratory, Chemistry Department, Faculty of Science, Minia University, Minia 61519, Egypt.
⁵ Phytochemistry Department, National Research Centre, 33 El-Bohouth St., Dokki, Giza 12622, Egypt; Department of Pharmaceutical Biology, Institute of Pharmacy and Biochemistry, University of Mainz, Staudinger Weg 5, 55128 Mainz, Germany.
⁶ Institute of Bioresources and Sustainable Development, India.
⁷ Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan. Electronic address: umeyama@ph.bunri-u.ac.jp.

PMID: 29913194
DOI: 10.1016/j.fitote.2018.06.010

Abstract

A new unusual seco-isopimarane, kaemgalangol A (1) and 12 usual analogs (2-13) were isolated from the rhizomes of Kaempferia galanga (Family: Zingiberaceae). KaemgalangolA (1) represented a rarely isolated 9,10-seco-isopimarane skeleton. The chemical structures of the isolated compounds were mainlyinvestigated by spectroscopic techniques such as 1D, 2D NMR, and HRMS. The absolute configuration of 1-3 was studied by X-ray diffraction analysis as well as experimental and TDDFT-calculated electronic circular dichroism. Among the isolated diterpenoids, 5, 6 and 9 exhibited cytotoxic activity against HeLa (IC₅₀ 75.1, 74.2 and 76.5 μM, respectively) and HSC-2 (IC₅₀ 69.9, 53.3 and 58.2 μM, respectively) cancer cells.

Keywords: Absolute configuration; Cytotoxicity; Kaemgalangol A; Kaempferia galanga; Seco-isopimarane; Theoretical calculations; X-ray.

MeSH terms

Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Diterpenes / chemistry*
Diterpenes / isolation & purification
HeLa Cells
Humans
Molecular Structure
Rhizome / chemistry*
Zingiberaceae / chemistry*

Substances

Antineoplastic Agents, Phytogenic
Diterpenes
kaemgalangol A