New alkaloidal metabolites from cultures of entomopathogenic fungus Cordyceps takaomontana NBRC 101754

Maichi Hama; Abdelsamed I Elshamy; Tatsuro Yoneyama; Yusuke Kasai; Hirohumi Yamamoto; Kana Tanigawa; Ayari Oshiro; Masaaki Noji; Sayaka Ban; Hiroshi Imagawa; Akemi Umeyama

doi:10.1016/j.fitote.2019.104364

New alkaloidal metabolites from cultures of entomopathogenic fungus Cordyceps takaomontana NBRC 101754

Fitoterapia. 2019 Nov:139:104364. doi: 10.1016/j.fitote.2019.104364. Epub 2019 Oct 17.

Affiliations

¹ Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
² Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan; Chemistry of Natural Compounds Department, National Research Centre, Dokki, 12622 Giza, Egypt. Electronic address: elshamynrc@yahoo.com.
³ Medical Mycology Research Center, Chiba University, Japan.

PMID: 31629870
DOI: 10.1016/j.fitote.2019.104364

Abstract

Two new alkaloidal metabolites, cordytakaoamides A (1) and B (2), as well as, 2-[(2-hydroxyethyl) amino] benzoic acid (3) and 2E-decenamide (4), and three known compounds (5-7) were isolated from ethyl acetate and n-butanol soluble portions of the entomopathogenic fungus, Cordyceps takaomontana NBRC 101754. Compounds 3 and 4 were isolated here for first time from natural resources. The chemical structures were established depending upon spectroscopic techniques such as 1D, 2D NMR, and HRMS. The absolute configuration of 1 and 2 was elucidated via the total synthesis of 1 as well as the experimental circular dichroism. Compound 3 was confirmed by a signal crystal X-ray analysis.

Keywords: Alkaloidal metabolites; Cordyceps takaomontana; Cordytakaoamides; Total synthesis; X-ray.

MeSH terms

Alkaloids / isolation & purification*
Cordyceps / chemistry*
Molecular Structure

Substances

Alkaloids