Sesquiterpenes and Other Constituents from Dendranthema zawadskii var. latilobum

Abstract

Six new germacranolides, zawadskinolides A-F (1-6), and a new eudesmane glucoside, chrysantiloboside (7) were isolated from the aerial parts of Dendranthema zawadskii var. latilobum, along with thirteen known constituents. Their structures were elucidated by means of spectroscopic evidence. Bioassay showed that flavonoids such as apigenin (9) farnesyl protein transferase (FPTase) inhibition, 12) and quinone reductase modulation.13) In addition, the 70% EtOH extract and its hexane-soluble fraction were reported to strongly inhibit inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) activity.14) In the course of our studies on the constituents of the MeOH extract of the aerial parts of D. zawadskii var. latilobum, six new sesquiterpene lactones, zawadskinolides A-F (1-6), and a new eudesmane glucoside, chrysantiloboside (7), together with thirteen known compounds were isolated. Since NO and prostaglandin E 2 are considered the major inflammatory mediators and in keeping with the traditional medical applications of this herb 2) and the previous report on its anti-inflammatory activity, 14) the isolates were evaluated for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells. In this paper, we report the isolation, structural elucidation and biological evaluation of these compounds. Results and DiscussionDried aerial parts of D. zawadskii var. latilobum were extracted with MeOH and then fractionated with hexane, CH 2 Cl 2 , EtOAc, n-BuOH and water. By combined chromatographic separations of these extracts, seven new and thirteen known compounds were isolated. Their structures were elucidated using physicochemical and spectroscopic methods.

Hyperoside and rutin of Nelumbo nucifera induce mitochondrial apoptosis through a caspase-dependent mechanism in HT-29 human colon cancer cells

“…Numerous previous studies aimed to identify anticancer components from natural sources (20)(21)(22)(23). Therefore, the effects of hyperoside and rutin on the proliferation and apoptosis in HT-29 human colon cancer cells, through activity-guided fractionation and isolation methods, are investigated in the present study.…”

Sesquiterpenes From Oplopanax elatus Stems and Their Anti-Photoaging Effects by Down-Regulating Matrix Metalloproteinase-1 Expression via Anti-Inflammation

“…Moreover, the HMBC cross-peaks were observed from H 2 -6 to C-7, C-8; H-11 to C-6–8; H 2 -12 to C-7, C-13; H 3 -13 to C-7, C-12; H 3 -14 to C-1, C-5, C-9, C-10; H 3 -15 to C-3–5; H-1′ to C-1 ( Figure 3 ). Then, the planar structure of two was determined, which was the same as those chrysantiloboside ( Shin et al, 2012 ) and iwayoside C ( Ding et al, 2011 ). The NOE cross-peaks between δ H 1.30 (H-5) and δ H 1.14 (H 3 -15), 1.90 (H α -9), 3.42 (H-1); δ H 2.14 (H β -9) and δ H 1.01 (H 3 -14) ( Figure 4 ) consolidated that 1-OH, 4-OH, H-5, and 14-CH 3 was in β , β , α , and β orientation, respectively.…”

Chemistry and Pharmacological Activity of Sesquiterpenoids from the Chrysanthemum Genus

“…All the sesquiterpenoids have been isolated from air-dried flowers or aerial parts of the Chrysanthemum genus, except angeloylcumambrin B (53), cumambrin A (54), cumambrin-B (55), and handelin (104) which were obtained from fresh whole herbs (Table 1). C. morifolium, C. indicum, C lavandulifolium, C. zawadskii, and C. ornatum have been reported to be rich in sesquiterpenoids, especially the C. morifolium and C. indicum species [16][17][18][19]. To the best of our knowledge, there is not a single comprehensive review on the sesquiterpenoids of the Chrysanthemum genus.…”