Polyol monoterpenes isolated from Chenopodium ambrosioides

• Published in: Natural product research Vol. 31; no. 21; pp. 2467 - 2472
• Main Authors: Hou, Shu-Qun, Li, Yan-Hong, Huang, Xiang-Zhong, Li, Rong, Lu, Huai, Tian, Kai, Ruan, Rong-Sheng, Li, Yu-Kui
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 01.11.2017; Taylor & Francis Ltd
• Subjects: Alcohols; Animals; anti-inflammatory activity; Anti-inflammatory agents; Anti-Inflammatory Agents, Non-Steroidal - chemistry; Anti-Inflammatory Agents, Non-Steroidal - isolation & purification; Anti-Inflammatory Agents, Non-Steroidal - pharmacology; Cell Line; Chenopodium ambrosioides; Chenopodium ambrosioides - chemistry; Cyclohexane; Cyclohexene; Drug Evaluation, Preclinical - methods; Ethanol; Inflammation; Lipopolysaccharides; Macrophages; Macrophages - drug effects; Macrophages - metabolism; Magnetic Resonance Spectroscopy; Mice; Molecular Structure; Monoterpenes; Monoterpenes - chemistry; Monoterpenes - isolation & purification; Monoterpenes - pharmacology; NMR; Nuclear magnetic resonance; p-Menthane; Plant Stems - chemistry; Polymers - chemistry; Chenopodium ambrosioides; monoterpenes; anti-inflammatory activity
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2017.1314278

Phytochemical study on the 95% ethyl alcohol extract of stems of Chenopodium ambrosioides resulted in the isolation of two new polyol monoterpenes, 4-hydroxy-4(α or β)-isopropyl-2-methyl-2-cyclohexen-1-one (1) and 1-methyl-4β- isopropyl-1-cyclohexene-4α,5α,6α-triol (2), together with five known compounds, (1S,2S,3R,4S)-1-methyl-4-(propan-2-yl)cyclohexane-1,2,3,4-tetrol (3), (1R,2S,3S,4S)- 1,2,3,4-tetrahydroxy-p-menthane (4), (1R,2S)-3-p-menthen-1,2-diol (5), (1R,4S)-p- menth-2-en-1-ol (6) and 1,4-dihydroxy-p-menth-2-ene (7). The structures of the new compounds were established on the basis of detailed spectroscopic evidence including extensive 1D and 2D NMR techniques. Compounds 1-7 were evaluated for their anti-inflammatory activity, and compound 1 showed moderate ability to inhibit NO production of LPS-stimulated RAW 264.7 macrophages with an IC 50 value of 16.83 μM.