New Coumarins of the Family Apiaceae. I. Khellactone Esters from Phlojodicarpus sibiricus

• Published in: Chemistry of natural compounds Vol. 59; no. 5; pp. 842 - 847
• Main Authors: Olennikov, D. N., Chirikova, N. K.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.09.2023; Springer Nature; Springer; Springer Nature B.V
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry, Medicinal; Chemistry, Organic; Chemistry/Food Science; Coumarins; Esters; Hexanes; Life Sciences & Biomedicine; Mass spectrometry; NMR spectroscopy; Nuclear magnetic resonance spectroscopy; Organic Chemistry; Pharmacology & Pharmacy; Physical Sciences; Plant Sciences; Science & Technology; angular dihydropyranocoumarins; Apiaceae; cholinesterase; khellactone; ABSOLUTE-CONFIGURATION; Phlojodicarpus sibiricus; MS/MS; DERIVATIVES; CONSTITUENTS
• ISSN: 0009-3130; 1573-8388
• DOI: 10.1007/s10600-023-04131-3

An investigation of the hexane extract of subterranean organs of Phlojodicarpus sibiricus (Fisch.) Koso-Pol. (Apiaceae) led to the isolation of 20 compounds, including four new coumarins, the structures of which were elucidated using UV, CD, and NMR spectroscopy and mass spectrometry as (3′S,4′S)-3′-O-isovaleroyl-4′-O-isobutyroyl-cis-khellactone (phlojosibirin I, 1 ), (3′S,4′S)-3′-O-isobutyroyl-4′-O-angeloyl-cis-khellactone (phlojosibirin II, 2 ), (3′S,4′S)-3′-O-isobutyroyl-4′-O-senecioyl-cis-khellactone (phlojosibirin III, 3 ), and (3′S,4′S)-3′-O-senecioyl-4′-O-isobutyroyl-cis-khellactone (phlojosibirin IV, 4 ). Compounds 1–4 possessed inhibitory activity against acetyl- and butyrylcholinesterase.