Anti-Alzheimer's flavanolignans from Ceiba pentandra aerial parts.

Mohamed E Abouelela, Mohamed A A Orabi, Reda A Abdelhamid, Mohamed S A Abdelkader, Faten M M Darwish, Mayumi Hotsumi, Hiroyuki Konno

Journal: Fitoterapia 2021;143():104541

PMID: 32151639

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Abstract

Four flavanolignans, ceibapentains A (1) and B (2) and cinchonains Ia (3) and Ib (4), were isolated for the first time from an ethyl acetate extract of Ceiba pentandra (L) (Bombacaceae) aerial parts. The ceibapentains A (1) and B (2) are new compounds and their structures, including the absolute configurations, were determined by HRESIMS, 1D and 2D NMR, and electronic circular dichroism analyses, then compared with reported data. Compounds 1-4 were tested for their anti-Alzheimer's activity via an assessment of their inhibitory effect on amyloid β42 aggregation using a thioflavin T assay. The results revealed that cinchonain Ia (3) showed a higher inhibitory effect (91%) than the standard curcumin (70%). Compounds 1, 2, and 4 exhibited moderate activity, with inhibition ratios of 43%, 47%, and 58%, respectively. A molecular docking study on the binding mode of 3 and curcumin with an amyloid β1-40 peptide fibril structure indicated a high affinity of cinchonain 1a (3) towards amyloid β1-40 peptide, in agreement with the experimental results.

Address: Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut-Branch, 71524 Assiut, Egypt.; Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut-Branch, 71524 Assiut, Egypt. Electronic address: [email protected].; Department of Pharmacognosy, Faculty of Pharmacy, Sohag University, Sohag 11432, Egypt.; Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt.; Department of Biochemical Engineering, Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata 992-8510, Japan.

DOI: 10.1016/j.fitote.2020.104541

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MeSH Terms: Amyloid beta-Peptides, Ceiba, Circular Dichroism, Egypt, Flavonolignans, Humans, Molecular Docking Simulation, Molecular Structure, Peptide Fragments, Phytochemicals, Plant Components, Aerial, Plant Extracts