Homoisoflavonoids from the bulbs of Bellevalia longipes and an assessment of their potential cytotoxic activity. (November 2022)

• Record Type: Journal Article
• Authors: El-Elimat, Tamam; Al-Qiam, Reema; Burdette, Joanna E.; Al Sharie, Ahmed H.; Al-Gharaibeh, Mohammad; Oberlies, Nicholas H.
• Is Part Of: Phytochemistry. Volume 203(2022)
• Publication Date: 2022-11
• Subjects: Bellevalia longipes Post -- Asparagaceae -- Homoisoflavonoids -- Cytotoxic activity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2022.113343
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Seven undescribed homoisoflavonoids were identified from the bulbs of Bellevalia longipes Post (Asparagaceae) as well as thirteen known and one natural homoisoflavonoid that had been reported as a synthetic product previously. A general approach for recognizing homoisoflavonoids via NMR spectroscopy data were presented. The undescribed compounds were: 8-dehydroxy-5- O -demethyl-6-hydroxyscillapersicone, 6-methoxyscillapersicone, 5- O -demethyl-6-methoxyscillapersicone, 8- O -methylscillapersicone, 4′- O- methylscillapersicone, 4′, 8- O, O -dimethylscillapersicone, 3′- O- methylscillapersicone, and 3-hydroxy-desmethylophiopogonanone A. Structures were determined based on analysis of HRMS and NMR data, while absolute configurations were assigned using ECD spectroscopy. Human cancer cell lines were used to assess the cytotoxic activities of the isolated compounds, where 3-dehydroxy-3′-hydroxyeucomol showed IC50 values of 0.62 μM, 5.36 μM, and 2.52 μM, when tested against MDA-MB-435 (melanoma), MDA-MB-231 (breast), and OVCAR3 (ovarian) cells, respectively. Graphical abstract: A total of nineteen homoisoflavonoids, including seven that were undescribed, were identified from the bulbs of Bellevalia longipes Post (Asparagaceae). The cytotoxic activities of the isolated compounds were assessed using a panel of human cancer cell lines. Image 1 Highlights: Eight undescribed natural homoisoflavonoids were identified. Thirteen known compounds were identified. Structures determined based on HRMS and NMR data. Absolute configurations assigned via ECD spectroscopy. Cytotoxic activities assessed using an array of human cancer cell lines.