Two new C-benzylated chalcones and one new mimosin-type homoisoflavonoid from the twigs and leaves of Caesalpinia digyna

Haobei Qin; Dewen Bi; Fengqiu Li; Ruilong Luo; Hongdan Zhuang; Liqin Wang

doi:10.1016/j.fitote.2022.105279

Two new C-benzylated chalcones and one new mimosin-type homoisoflavonoid from the twigs and leaves of Caesalpinia digyna

Fitoterapia. 2022 Oct:162:105279. doi: 10.1016/j.fitote.2022.105279. Epub 2022 Aug 12.

Authors

Haobei Qin¹, Dewen Bi¹, Fengqiu Li¹, Ruilong Luo¹, Hongdan Zhuang¹, Liqin Wang²

Affiliations

¹ Faculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650050, PR China.
² Faculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650050, PR China. Electronic address: lqwang@ynnu.edu.cn.

PMID: 35964851
DOI: 10.1016/j.fitote.2022.105279

Abstract

Two new C-benzylated chalcones, 2',4'-dihydroxy-3'-(2-hydroxylbenzyl) chalcone (1) and 2',4'-dihydroxy-5'-(2-hydroxybenzyl) chalcone (2), one new and one known mimosin-type homoisoflavonoid, mimosol H (7) and mimosol G (8), together with four known chalcones (3-6) and four known sappanin-type homoisoflavonoids (9-12), were isolated from the twigs and leaves of Caesalpinia digyna. Their structures were characterized by comprehensive spectroscopic analyses (including NMR and HRESIMS). Compounds 1, 2 and 8 exhibited moderate cytotoxicity against SMMC-7721, A-549 and/or MDA-MB-231 cell lines with IC₅₀ values ranging from 11.41 ± 0.88 to 30.01 ± 1.56 μM. Notably, C-benzyl chalcones (1 and 2) were isolated from species of the genus Caesalpinia for the first time. Homoisoflavonoids 7 and 8 are the first examples of mimosin-type homoisoflavonoids reported in Caesalpinia digyna.

Keywords: C-benzylated chalcones; Caesalpinia; Caesalpinia digyna; Mimosin-type homoisoflavonoid.

MeSH terms

Caesalpinia* / chemistry
Chalcone*
Chalcones* / pharmacology
Molecular Structure
Plant Leaves / chemistry

Substances

Chalcones
Chalcone