Chodatiionosides A and B: two new megastigmane glycosides from Chorisia chodatii leaves

Mamdouh Nabil Samy; John Refaat Fahim; Sachiko Sugimoto; Hideaki Otsuka; Katsuyoshi Matsunami; Mohamed Salah Kamel

doi:10.1007/s11418-016-1052-7

Chodatiionosides A and B: two new megastigmane glycosides from Chorisia chodatii leaves

J Nat Med. 2017 Jan;71(1):321-328. doi: 10.1007/s11418-016-1052-7. Epub 2016 Oct 19.

Authors

Mamdouh Nabil Samy^{1

2}, John Refaat Fahim², Sachiko Sugimoto¹, Hideaki Otsuka^{1

3}, Katsuyoshi Matsunami⁴, Mohamed Salah Kamel²

Affiliations

¹ Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8553, Japan.
² Department of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia, 61519, Egypt.
³ Department of Natural Products Chemistry, Faculty of Pharmacy, Yasuda Women's University, 6-13-1 Yasuhigashi, Asaminami-ku, Hiroshima, 731-0153, Japan.
⁴ Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8553, Japan. [email protected].

PMID: 27761694
DOI: 10.1007/s11418-016-1052-7

Abstract

Phytochemical investigation of Chorisia chodatii Hassl. leaves led to the isolation of an unusual rearranged megastigmane glycoside; chodatiionoside A (1) and another new megastigmane glycoside; chodatiionoside B (2), together with three known megastigmane glycosides (3-5) and one known flavonoid glycoside (6). Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments (¹H, ¹³C, DEPT, COSY, HSQC and HMBC) in combination with HR-ESI-MS, CD and modified Mosher's method. As a result, chodatiionoside A has been elucidated as a first example of an unusual rearranged form of megastigmane.

Keywords: Bombacaceae; Chodatiionoside; Chorisia chodatii; Megastigmane glycoside.

MeSH terms

Cyclohexanones / chemistry*
Glucosides / chemistry*
Molecular Structure
Norisoprenoids / chemistry*
Plant Leaves / chemistry*

Substances

Cyclohexanones
Glucosides
Norisoprenoids
megastigmane