UV-guided isolation of enantiomeric polyacetylenes from Bupleurum scorzonerifolium Willd. with inhibitory effects against LPS-induced NO release in BV-2 microglial cells.

UV-guided fractionation led to the isolation of thirteen new polyacetylenes (1-13) from the roots of Bupleurum scorzonerifolium Willd. All polyacetylenes were analyzed as racemates since the lack of optical activity and Cotton effects in the ECD spectra. The sequent chiral-phase HPLC resolution successfully gave twelve pairs of enantiomers 1a/1b and 3a/3b-13a/13b. Their structures were elucidated based on the HRESIMS and NMR data analyses. The absolute configurations were determined by the combination of Snatzke's method, electronic circular dichroism calculations, and single-crystal X-ray diffraction. Using Griess methods and MTT assays, polyacetylenes 1a, 3a, 4a/4b-12a/12b, and 13a displayed inhibitory activities against LPS-induced NO release in BV-2 microglial cells.

Secondary Metabolites from the Marine Sponges of the Genus Petrosia: A Literature Review of 43 Years of Research.

Sponges are prolific sources of various natural products that have provided the chemical scaffolds for new drugs. The sponges of the genus Petrosia inhabit various regions and contain a variety of biologically active natural products such as polyacetylenes, sterols, meroterpenoids, and alkaloids. This review aims to provide a comprehensive summary of the chemical structures and biological activities of Petrosia metabolites covering a period of more than four decades (between 1978 and 2020). It is also described in this review that the major groups of metabolites from members of the genus Petrosia differed with latitude. The polyacetylenes were identified to be the most predominant metabolites in Petrosia sponges in temperate regions, while tropical Petrosia species were sources of a greater variety of metabolites, such as meroterpenoids, sterols, polyacetylenes, and alkaloids.

Bioactive small secondary metabolites from the mushrooms Lentinula edodes and Flammulina velutipes.

Mushrooms have been attracting attention as a source of bioactive compounds for the development of dietary supplements and medicines. Many researchers have reported pharmacological effects of edible mushrooms, and have isolated and identified bioactive substances. Lentinula edodes (shiitake) and Flammulina velutipes (enokitake) are the cultivated edible mushrooms that are popular throughout the world. In L. edodes, polyacetylenes and sulfur compounds have been shown to display antimicrobial activity. In F. velutipes, many types of bioactive terpenes have been reported from mycelium culture filtrate or solid culture substrate. This article reviews the bioactive metabolites of low-molecular weight from L. edodes and F. velutipes.

Toonasindiynes A-F, new polyacetylenes from Toona sinensis with cytotoxic and anti-inflammatory activities.

The plants of genus Toona are well known for diverse limonoid secondary metabolites, while polyacetylenes are rarely found from Toona species. In this work, six new polyacetylenes toonasindiynes A-F (1-6) and six known analogues (7-12) were isolated from the root bark of Toona sinensis. Their structures and absolute configurations were elucidated by HRESIMS, 1D and 2D NMR spectroscopic analysis, modified Mosher's method, and biosynthetic consideration. These polyacetylenes share the same 4,6-diyne moiety with different side chain length and different oxidation degree. Bioactivity screening revealed the cytotoxic activity of 3, 5, 9, and 11 against U2OS cells, and the inhibitory effects on nitric oxide (NO) production of 1, 2, 5, 8, 9, and 11 in lipopolysaccharide-induced RAW 264.7 cells.

Three new polyacetylene glycosides (PAGs) from the aerial part of Launaea capitata (Asteraceae) with anti-biofilm activity against Staphylococcus aureus.

Four polyacetylenic glycosides, three of which are new, together with two known flavonoids were isolated from the methanol extract of the aerial parts of Launaea capitate, designated bidensyneoside A1 (1), 6´-O-acetyl-bidensyneoside A1 (2), bidensyneoside E (3), bidensyneoside F (4), luteolin (5) and luteolin-7-glucoside (6) also known as cynaroside. Their structures were elucidated by comprehensive analysis of 1D, 2D-NMR and HR-MS data. The absolute configuration of the bidensyneosides was determined by Mosher ester analysis and the optical rotation values. The isolated compounds were tested against biofilm formation of Staphylococcus aureus as well as against several pathogens including Gram-positive bacteria, Gram-negative bacteria, fungi and yeasts. Furthermore, they were tested for their cytotoxicity against two cancer cell lines L929 and KB-3-1. Compound 4 showed moderate inhibition of S. aureus biofilm formation with 30% and 25% at 256 and 128 µg/mL, respectively, while compounds 1 and 5 showed weak inhibition with 20% at 256 µg/mL. Compound 5 showed moderate cytotoxicity against both cell lines L929 and KB-3-1, with IC50 values of 18 µg/mL.

Isolation and structure elucidation of two new compounds from artemisia Ordosica Krasch.

Two new compounds, namely arteordoyn A (1) and arteordoyn B (2), together with four known compounds, were isolated from the petroleum ether extract of Artemisia ordosica Krasch. The structures elucidation of 1 and 2 were carried out by 1D-NMR (1H and 13C NMR), 2D-NMR (COSY, HSQC, HMBC and NOESY) and HR-ESI-MS spectral analysis.

Oxygenated C17 polyacetylene metabolites from Algerian Eryngium tricuspidatum L. roots: Structure and biological activity.

The secondary metabolite pattern of Eryngium tricuspidatum has been found to be dominated by C17 acetylene oxylipins, according to the chemistry reported in the literature for the genus Eryngium. Two new oxylipins, 11-acetoxy-falcarindiol (4) and 1,2-dihydro-11-acetoxy-falcarindiol (5) have been isolated, along with main related polyacetylenes 1-3 and the already known monoterpene aldehydes 6-10, from the petroleum ether extract of roots. The structure and the absolute configuration of compounds 4 and 5 have been determined by spectroscopic methods as well as by comparison with related known compounds. Polyacetylenes 1-4 inhibited significantly the in vitro growth of a series of cancer cell lines, ranging from 0.3 to 29 µM, whereas 5 was inactive.