Iridoids and other constituents from the leaves and stems of Valeriana officinalis var. latifolia

• Published in: Phytochemistry (Oxford) Vol. 218; p. 113934
• Main Authors: Liu, Jia-Jin, Hao, Jun-Jie, Tan, Min, Liao, Cai-Cen, Liu, Dan, Li, Hong-Mei, Li, Rong-Tao
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.02.2024; Elsevier
• Subjects: Anti-inflammatory; Biochemistry & Molecular Biology; Caprifoliaceae; Cytotoxicity; Iridoids; Iridoids - chemistry; Iridoids - pharmacology; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Roots - chemistry; Plant Sciences; Science & Technology; Valerian - chemistry; Valeriana officinalis var. latifolia; Valeriana officinalis var. latifolia; Cytotoxicity; Caprifoliaceae; Iridoids; Anti-inflammatory; MEGASTIGMANE; GLYCOSIDES; TERPENOIDS; FATTY-ACID ESTERS; SESQUITERPENES; IN-VITRO; CHEMICAL-CONSTITUENTS; LACTONES; ROOTS; ACYLATED IRIDOIDS
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2023.113934

Fifty-nine compounds, including nineteen previously undescribed iridoids (valeriananols A−S) and an undescribed alkaloid (5′-isovaleryl uridine), were isolated from the leaves and stems of Valeriana officinalis var. latifolia. Their structures were elucidated based on Mass spectrometry and NMR spectroscopy. The absolute configuration of valeriananols A−C, E−N, P, Q and S was determined by experimental and calculated electronic circular dichroism. Structurally, valeriananols A and B were two 1,3-seco-iridoids with a 3,6-epoxy moiety, valeriananols K and L were a pair of C-4 epimers, while valeriananol S was a 4′-deoxy iridoid glycoside. In addition, valeriananol P, stenopterin A and patriscabioin C exhibited significant inhibition on nitric oxide production with IC50 values of 10.31, 3.93 and 8.69 μM, respectively. Furthermore, stenopterin A and patriscabioin C showed anti-proliferation activity on the MCF-7 cell line with IC50 values of 17.28 and 13.89 μM, respectively. [Display omitted] •Twenty undescribed compounds were isolated from V. officinalis var. Latifolia.•Valeriananols A and B are two 1,3-seco-iridoids with 3,6-epoxy moiety.•Valeriananol S was a 4′-deoxy iridoid glycoside.•Three compounds showed significant inhibitory effects of nitric oxide production.•Stenopterin A and patriscabioin C showed cytotoxicity against the MCF-7 cell line.