A novel cyclohexane carboxylic acid derivative from Black Turtle Bean (Phaseolus vulgaris L.)

Authors: BALKISU, ABDULRAHMAN - University Of Mississippi; FADIME, AYDOGAN - University Of Mississippi; ZULFIQAR, FAZILA - University Of Mississippi; ZHAO, JIANPING - University Of Mississippi; KHAN, IKHLAS - University Of Mississippi

Submitted to: Records of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 4/22/2022
Publication Date: 5/5/2022
Citation: Balkisu, A., Fadime, A., Zulfiqar, F., Zhao, J., Khan, I. 2022. A novel cyclohexane carboxylic acid derivative from Black Turtle Bean (Phaseolus vulgaris L.). Records of Natural Products. http://doi.org/10.25135/rnp.325.2202.2361.
DOI: https://doi.org/10.25135/rnp.325.2202.2361

Interpretive Summary: Black turtle bean is a variety of common bean belonging to the Phaseolus vulgaris L. species of the Fabaceae family and is one of the most important varieties of cultivated edible legumes like kidney, pea, white, yellow beans, etc. P. vulgaris seeds are an important dietary component widely cultivated and consumed in Nigeria and other tropical and subtropical countries. Black turtle beans, considered a functional food due to the presence of nutrients such as lectins and proteins, may exhibit the ability to prevent disease conditions like cardiovascular, diabetes, cancer, metabolic syndrome, and obesity. Various biological activities for extracts of P. vulgaris seeds have been reported including antidepressant, antioxidant, anti-inflammatory, anti-sickling, antioxidative, and antidiabetic. Beans have high nutritional value due to their protein content with peptides, lectins, and amino acids. Furthermore, flavonoids, phenolic acids, tannins, alkaloids, sapogenins, and lectins-type phytochemicals have been reported in P. vulgaris seeds. The growing interest in the identification of naturally occurring nutritive and non-nutritive chemical components of cereals, legumes, and spices and their roles in preventing chronic diseases has led to investigation of P. vulgaris seeds. The secondary metabolite profiles of beans differ by variety and environmental factors. This study reports the isolation of five constituents from the ethanolic extract of black turtle beans including a previously undescribed compound.

Technical Abstract: Black turtle bean is a variety of Phaseolus vulgaris L. in the legume family Fabaceae and is consumed as food worldwide. A targeted phytochemical investigation of the ethanolic extract of its seeds, focusing on constituents other than the lipophilic metabolites, resulted in the isolation and characterization of five compounds (1-5). Compound 1 (phasvulic acid), a previously undescribed cyclohexane carboxylic acid derivative, was characterized as (Z)-3-hydroxy-2-(5-hydroxypent-2-en-1-yl)cyclohexane-1-carboxylic acid based on spectral data including 1D and 2D NMR (1H, 13C, COSY, HSQC, and HMBC) and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). Other compounds were formerly described as dihydrophaseic acid (2), uridine (3), stigmasterol-3-O-ß-D glucopyranoside (4), and ß-sitosterol-3-O-ß-D-glucopyranoside (5).