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- Title
Withaninsams A and B: Phenylpropanoid Esters from the Roots of Indian Ginseng (Withania somnifera).
- Authors
Baek, Su Cheol; Lee, Seoyoung; Kim, Sil; Jo, Mun Seok; Yu, Jae Sik; Ko, Yoon-Joo; Cho, Young-Chang; Kim, Ki Hyun
- Abstract
Withania somnifera (L.) Dunal (Solanaceae), known as Indian ginseng or ashwagandha, has been used in Indian Ayurveda for the treatment of a variety of disorders, such as diabetes and reproductive and nervous system disorders. It is particularly used as a general health tonic, analgesic, and sedative. As part of continuing projects to discover unique bioactive natural products from medicinal plants, phytochemical investigation of the roots of W. somnifera combined with a liquid chromatography–mass spectrometry (LC/MS)-based analysis has led to the isolation of two novel phenylpropanoid esters, Withaninsams A (1) and B (2), as an inseparable mixture, along with three known phenolic compounds (3, 4, and 6) and a pyrazole alkaloid (5). The structures of the new compounds were elucidated using a combination of spectroscopic methods, including one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HR-ESIMS). Withaninsams A (1) and B (2) are phenylpropanoid esters that contain a side chain, 4-methyl-1,4-pentanediol unit. To the best of our knowledge, the present study is the first to report on phenylpropanoid esters with 4-methyl-1,4-pentanediol unit. The anti-inflammatory activity of the isolated compounds (1–6) was evaluated by determining their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages, where compound 3 inhibited LPS-induced NO production (IC50 = 33.3 μM) and TNF-α production, a pro-inflammatory cytokine (IC50 = 40.9 μM). The anti-inflammatory mechanism through the inhibition of transcriptional iNOS protein expression was confirmed by western blotting experiments for the active compound 3, which showed decreased iNOS protein expression.
- Subjects
LIPOPOLYSACCHARIDES; WITHANIA somnifera; LIQUID chromatography-mass spectrometry; PERITONEAL macrophages; INTERLEUKIN-33; ESTERS; NUCLEAR magnetic resonance; MASS spectrometry
- Publication
Plants (2223-7747), 2019, Vol 8, Issue 12, p527
- ISSN
2223-7747
- Publication type
Article
- DOI
10.3390/plants8120527