Constituents of Bupleurum praealtum and Bupleurum veronense with Potential Immunomodulatory Activity

• Published in: Journal of natural products (Washington, D.C.) Vol. 83; no. 10; pp. 2902 - 2914
• Main Authors: Radulovic, Niko, Stevanovic, Milica, Nesic, Milan, Stojanovic, Nikola, Randelovic, Pavle, Randelovic, Vladimir
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 23.10.2020; Amer Chemical Soc
• Subjects: Chemistry, Medicinal; Life Sciences & Biomedicine; Pharmacology & Pharmacy; Plant Sciences; Science & Technology; POLYACETYLENES; FINGERPRINTS; GENUS BUPLEURUM; CIS-PARINARIC ACID; BIOSYNTHESIS; APIACEAE; LIGNANS; POLYACETYLENVERBINDUNGEN; IDENTIFICATION; CYTOTOXICITY
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.0c00437

In this investigation, chromatographic separations of the diethyl ether extracts of two European annual Bupleurum taxa, B. praealtum and B. veronense, yielded nine new natural products, namely, a series of esters of stereoisomeric tetradeca-5,7,9,11-tetraen-1-ols (1–4 and 8), a tetra-unsaturated γ-tetradecalactone (5), a dibenzylbutyrolactone lignan (7-oxoarcitin, 6), a falcarinol-related 17-membered macrolide (7) possessing a conjugated diyne-system, and an acylphloroglucinol derivative (9). All these new compounds were fully characterized by NMR, IR, UV, MS, and optical rotation measurement, including 1H NMR full spin spectral simulation, whereas the absolute configurations of 1, 5, and 9 were determined via chemical correlations and NMR analysis of Mosher esters. The in vitro potential immunomodulatory activities of 1, 4, 5, and (+)-arcitin were assessed by determining their effects on the functional properties of isolated rat splenocytes and peritoneal macrophages. The results obtained support the known immunomodulatory ethnomedicinal usage of Bupleurum species.