Highly Oxidized Guaianolide Sesquiterpenoids with Potential Anti-inflammatory Activity from Chrysanthemum indicum

Abstract

Ten new highly oxidized monomeric (1-8) and dimeric guaianolides (9 and 10), along with two known guaianolide derivatives (11 and 12), were isolated from the aerial parts of Chrysanthemum indicum using a bioassay-guided fractionation procedure. The new compounds were characterized by the basic analysis of the spectroscopic data obtained, and the absolute configurations were determined by both empirical approaches and ECD calculations. Inhibitory effects of 1-12 on nitric oxide production were investigated in lipopolysaccaride (LPS)-mediated RAW 264.7 cells, and most of them (1-8 and 11) displayed IC values in the range 1.4-9.7 μM. Moreover, a mechanistic study revealed that the potential anti-inflammatory activity of compound 1 appears to be mediated via suppression of an LPS-induced NF-κB pathway and down-regulation of MAPK activation.

Six New Methyl Apiofuranosides from the Bark of Phellodendron chinense Schneid and Their Inhibitory Effects on Nitric Oxide Production

“…An MTT assay was used to evaluate RAW 264.7 cell viability as previously described [34]. The mitochondrial-dependent reduction of 3-(4,5-dimethylthizaol-2yl)-2,5-diphenyl tetrazolium bromide (MTT) to formazan was used to measure cell respiration as an indicator of cell viability [35]. Briefly, after 24 h incubation with or without compounds (6.25–100 μM), an MTT solution (final concentration 5 mg/mL) was added and the cells were incubated for another 2.5 h at 37 °C.…”

Chemistry and Pharmacological Activity of Sesquiterpenoids from the Chrysanthemum Genus

“…Compound 90 contains chlorine atoms. So far, 60 chlorine-containing guaianolide-type sesquiterpenoids have been isolated from Compositae [39,46,47]. Examples of structures are given in Figure 3.…”

“…Chrysanthemulide H (86), 8tigloyldesacetylezomontanin (87), chrysanthemulide F (89), chrysanthemulide G (90), chrysanthemulide A (92), chrysanthemulide B (93), chrysanthemulide C (94), chrysanthemulide D (95), and chrysanthemulide E (96) and 98-103 displayed NO production inhibitory activities with IC 50 values ranging from 1.4 to 9.7 µM. The IC 50 value of the positive control drug L-NMMA was 25.8 µM [39,61]. These sesquiterpenoids have great antiinflammatory potential.…”

“…These sesquiterpenoids have great antiinflammatory potential. A mechanistic study revealed that the potential anti-inflammatory activity of compound chrysanthemulide A (92) appears to be mediated via suppression of an LPS-induced NF-κB pathway and downregulation of MAPK activation [39,61]. In addition, using H9c2 cardiocytes impaired by lipopolysaccharide (LPS), compounds chrysanthguaianolactone D (65), 3α,4α,10β-trihydroxy-8α-acetoxyguai-1,11(13)-dien-6α,12-olide (67), 3α,4α,10β-trihydroxy-8α-acetoxy-11βH-guai-1-en-6α,12-olide (68), 8α-(angelyloxy)-3β,4β-dihydroxy-5αH,6βH,7αH,11αH-guai-1(10)-en-12,6-olide (71), and 3β,4α-dihydroxy-8α-angelyloxy-1(10),11(13)-dien-6β,12-olide (75) exhibited anti-inflammatory activity [33].…”

Agrobacterium-Mediated Transformation of Chrysanthemum with Artemisinin Biosynthesis Pathway Genes

“…An obvious way to increase artemisinin production in heterologous systems is to select a plant-host with a naturally high content of terpenoids and their precursors. Many such plants are known, especially among crop plant belonging to flavor herbs or medicines, such as chrysanthemum [12][13][14]. The high content of various terpenoids is characteristic of the widespread Chrysanthemum morifolium Ramat, which is one of the leading ornamental crops, second to roses, cultivated almost everywhere [15,16].…”