Bioactive Sesquiterpenoid and Polyacetylene Glycosides from Atractylodes lancea

Abstract

Nine new sesquiterpenoids (1-9), five new polyacetylenes (10-14), and six known compounds were isolated from the rhizomes of Atractylodes lancea. These new chemical structures were established using NMR, MS, and ECD data. Notably, compounds 3-5, the aglycone of which possesses two stereogenic centers (C-5 and C-7), exhibited similar ECD spectra to compounds 1 and 2, the aglycone of which possesses one stereogenic center (C-7). Such a difference was supported by the experimental and calculated ECD data and single-crystallographic analyses of 3a. In addition, compound 3 inhibited lipopolysaccharide-induced NO production in BV2 cells with an IC50 value of 11.39 μM (positive control curcumin, IC50 = 4.77 μM); compound 4 showed better hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury than the positive drug (bicyclol) at a concentration of 10 μM (p < 0.001).

Anticancer Properties of Lobetyolin, an Essential Component of Radix Codonopsis (Dangshen)

“…An anti-inflammatory activity has also been mentioned with other LBT-containing TCM preparations [86,87]. Several polyacetylene glycosides display anti-inflammatory properties [88][89][90][91][92], such as coreosides A-D which are potent inhibitors of cyclooxygenase-2 [93]. Illustration of the mechanism of action of LBT which was shown to block the transport of the tumor suppressor p53 from the cytoplasm to the nucleus, thereby modulating gene expression and inducing apoptosis of HCT-116 colon cancer cells [61].…”

Identification of Crepenynic Acid in the Seed Oil of Atractylodes lancea and A. macrocephala

“…Although polyacetylenes and polyacetylene glycosides are considered to be important bioactive components of atractyloides rhizome [5,7], and of many other traditional medicinal plants and fungi [26,27], their primary role in plants may be defense. Acetylenic acids and their derivatives have been shown to be potent antifungal and insecticidal agents, and they can also function as allelochemicals, inhibiting the growth of competing plants [27,28].…”

“…Extensive studies have been conducted to characterize the chemical composition of the rhizomes of both species. and a range of potential bioactive secondary metabolites have been identified including sesquiterpenoids, polyacetylenes and monoterpenes [3][4][5][6][7]. Although the roots of Atractylodes species have received much attention, seed acyl composition has not been reported.…”

Anti-Adipogenic Polyacetylene Glycosides from the Florets of Safflower (Carthamus tinctorius)

“…After solvent partition, the residue was solvent-partitioned again with acetone, affording the acetone-soluble fraction (68.7 g). All these fractions were initially analyzed by LC-MS, which confirmed the presence of components with a distinctive UV spectrum, which was characteristic of an enediyne chromophore [16,17] in the EtOAc-soluble fraction. To identify the compounds of interest, the EtOAc fraction (10.4 g) was resolved by silica gel column chromatography [300 g; eluted using a CH 2 Cl 2 /MeOH (50:1→1:1, v:v) gradient solvent system and washed with 90% MeOH] and investigated by monitoring through LC-MS using our in-house UV library.…”

“…The crude extract of the florets of C. tinctorius was solvent-partitioned using water and five organic solvents of increasing polarity (hexane, dichloromethane, ethyl acetate, n-butanol, and acetone). The obtained fractions were primarily monitored and analyzed by LC-MS, which allowed us to identify the presence of components with a distinctive UV spectrum in the EtOAc-soluble fraction, which is characteristic of an enediyne chromophore [16,17]. To identify the compounds of interest, the LC-MS-based phytochemical analysis of the EtOAc fraction and preparative and semi-preparative HPLC were performed; the processes resulted in the isolation of two new C 10 -polyacetylene glycosides (1 and 2) and five known analogs (3-7).…”