Cladamide: a new ceramide from the endophytic fungus Cladosporium cladosporioides

Abstract

A new ceramide, named cladamide (1), in addition to cinnamic acid (2), para-coumaric acid (3), stigmasterol-3-O-β-D-glucoside (4), and uracil (5), was isolated from the white beans culture of Cladosporium cladosporioides, a marine-derived endohpytic fungus isolated from the leaves of the mangrove, Avicennia marina (Forssk.) Vierh. Structure elucidation of compound 1 was established on the basis of extensive 1D and 2D NMR spectroscopic techniques in combination with HR-ESI-MS. The ability of the isolated compounds to inhibit acetylcholine esterase was evaluated. Compound 3 showed the highest acetylcholine esterase inhibitory activity (IC₅₀ = 0.057 ± 0.003 µM), followed by compound 4 (IC₅₀ = 0.068 ± 0.003 µM) and compound 1 (IC₅₀ = 0.099 ± 0.005 µM) compared to donepezil, the positive control, (IC₅₀ = 0.044 ± 0.002 µM). Compounds 2 and 5 showed lower activity (IC₅₀ = 0.182 ± 0.009 and 0.236 ± 0.012 µM, respectively). The results were further validated by molecular docking study.

Graphical Abstract

Keywords:

• Cladosporium cladosporioides
• ceramide
• acetylcholine esterase
• molecular docking

Acknowledgments

Authors would like to express gratitude and thanks to Prof. Tomofumi Miyamoto, graduate school of pharmaceutical sciences, Kyushu University, Japan and to Dr. Yhiya Amen, Department of Pharmacognosy Faculty of Pharmacy, Mansoura University, Mansoura, Egypt and Graduate School of Bioresource and Bioenvironmental Sciences, Kyushu University, Fukuoka, Japan for measuring the optical rotation of compound 1.

Disclosure statement

The authors declare no conflicts of interest.