Bioactive Sesquiterpenoids from the Peeled Stems of Syringa pinnatifolia

Journal of Natural Products
Ruifei ZhangXingyun Chai

Abstract

Fourteen new sesquiterpenoids, alashanoids A-H (1, 2, and 4-9), (+)-2,9-humuladien-6-ol-8-one (3b), and five pairs of enantiomers (1 and 4-7), along with eight known analogues (3a and 10-16) were isolated from the stems of Syringa pinnatifolia. The structures were established using IR, UV, MS, and NMR data. The absolute configurations of the new compounds were resolved by X-ray diffraction, a modification of Mosher's method, and experimental and calculated ECD data analysis. The new sesquiterpenoids represent three skeletons: a rare 2,2,5,9-tetramethylbicyclo[6.3.0]-undecane (1), a humulane-type (2-8), and a caryophyllene-type (9) skeleton. Compounds 6a, 7, and 11 showed protective effects against hypoxia-induced injury to H9c2 cells at a concentration of 40 μM, and 5-7, 11, and 13 inhibited NO production in LPS-induced RAW264.7 macrophage cells with IC50 values ranging from 13.6 to 70.6 μM. These compounds decreased the TNF-α and IL-6 levels in RAW264.7 cells in a concentration-dependent manner at 20-80 μM.

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Citations

Nov 25, 2018·Natural Product Research·Feng ZhaoXingyun Chai
Oct 5, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yuanyuan JiChunlin Long
Nov 26, 2019·Journal of Asian Natural Products Research·Bing PengXing-Yun Chai
Jan 26, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jianxin HanTao Yuan
Jun 18, 2020·Marine Drugs·Irina I KapustinaValentin A Stonik
Feb 13, 2021·Chemistry & Biodiversity·Meiwen HuangXingyun Chai
Oct 14, 2020·Journal of Ethnopharmacology·Wenbo ZhuHaixue Kuang
Apr 30, 2021·The Journal of Organic Chemistry·Shungang JiaoXingyun Chai
Jun 19, 2021·Journal of Asian Natural Products Research·Miao-Miao LiTao Yuan
Oct 3, 2019·Journal of Natural Products·Lina WangQiulin Wang
Dec 21, 2021·Chemistry & Biodiversity·Changxin LiuXingyun Chai

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