Pruinosanones A-C, anti-inflammatory isoflavone derivatives from Caragana pruinosa

doi:10.1038/srep31743

	Pruinosanones A-C, anti-inflammatory isoflavone derivatives from Caragana pruinosa
	Zheng, Chengjian 2; Wang, Liang 2; Han, Ting 2; Xin, Hailiang 2; Jiang, Yiping 2; Pan, Lan 1; Jia, Xiaoguang 1; Qin, Luping 2
刊名	Scientific reports
	2016-08-22
卷号	6 页码:31743
ISSN号	2045-2322
DOI	10.1038/srep31743
文献子类	Article
英文摘要	Pruinosanone A (1), a novel spirochromone, was isolated from the roots of Caragana pruinosa. Two biogenetically related isoflavone intermediates, pruinosanones B and C (2 and 3), were also isolated, together with five known analogs identified as 3-hydroxy-9-methoxypterocarpan (4), 7,2'-dihydroxy-4'-methoxyisoflavanol (5), retusin-8-methylether (6), 7,2'-dihydroxy-8,4'-dimethoxy isoflavone (7) and 7,3'-dihydroxy-8,4'-dimethoxy isoflavone (8). The structures of 1-3 were elucidated based on extensive spectroscopic methods. Notably, 1 is the first example of a spirochromone possessing an unprecedented pentacyclic skeleton containing a spiro[benzo[d][1,3]dioxole-2,3'-chroman]-4'-one motif, which was confirmed by X-ray diffraction analysis. A plausible biosynthetic pathway for 1 was also proposed. Compounds 1-8 were tested for their ability to inhibit nitric oxide (NO) production in LPS-induced RAW 264.7 macrophages, and compounds 1-3 were the most potent inhibitors of NO production, with IC50 values of 1.96, 1.93 and 1.58 μM, respectively. A structure-activity relationship analysis revealed that the fused 2-isopropenyl-2,3-dihydrofuran moiety plays a vital role in the potency of these compounds. Moreover, 1 was found to significantly inhibit inducible nitric oxide synthase (iNOS) protein expression, which accounts for the potent inhibition of NO production by this spirochromone.
语种	英语
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/266563]
专题	中国科学院上海药物研究所
作者单位	1.Xinjiang Institute of Chinese Materia Medica and Ethnodrug, Urumqi 830002, China 2.Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, Shanghai 200433, China;
推荐引用方式 GB/T 7714	Zheng, Chengjian,Wang, Liang,Han, Ting,et al. Pruinosanones A-C, anti-inflammatory isoflavone derivatives from Caragana pruinosa[J]. Scientific reports,2016,6:31743.
APA	Zheng, Chengjian.,Wang, Liang.,Han, Ting.,Xin, Hailiang.,Jiang, Yiping.,...&Qin, Luping.(2016).Pruinosanones A-C, anti-inflammatory isoflavone derivatives from Caragana pruinosa.Scientific reports,6,31743.
MLA	Zheng, Chengjian,et al."Pruinosanones A-C, anti-inflammatory isoflavone derivatives from Caragana pruinosa".Scientific reports 6(2016):31743.