Molecular Structure of 3-Hydroxy-4-Pyrone

Abstract

Aerial parts of Erigeron annuus and E. strigosus afforded 3-hydroxy-4-pyrone, the molecular structure of which was determined by single crystal X-ray diffraction.     

Trichosides A and B,new withanolide glucosides from Tricholepis eburnea

Trichosides A (1) and B (2), new withanolide glucosides, have been isolated from the n-butanolic fraction of the 75% methanolic extract of aerial parts of Tricholepis eburnea. Their structures were elucidated through spectroscopic analysis including ESI-MS, 2D NMR and acid hydrolysis.     

Chemical and genetic diversity of Ligularia virgaurea collected in northern Sichuan and adjacent areas of China. Isolation of 13 new compounds

Root chemicals and DNA sequences were analyzed for Ligularia virgaurea collected in the northern Sichuan Province and adjacent areas of China. Thirty-eight samples were found to contain five chemotypes, two known and three new ones. From samples of the new chemotypes, 13 new compounds were isolated, including 3 sesquiterpene dimers and some rearranged eremophilanes. The DNA sequences suggested that the chemotype differentiation had a genetic origin.     

20-Hydroxyecdysone from Stemmacantha uniflora Subsp. satzyperovii

The dynamics of 20-hydroxyecdysone content in vegetative and generative organs of Stemmacantha uniflora subsp. satzyperovii (Soskov) Dittrich, which is distributed over Primorskii Krai, were investigated. A high content of 20-hydroxyecdysone during the plant vegetative period is characteristic of growing organs. The amount is maximal for young leaves during development of racemes (7.8 g/mg) and for ripe achenes (11.15 g/mg).     

Structural studies of the chemical constituents of Tithonia tagetiflora Desv. (Asteraceae)

Tithonia tagetiflora Desv. (Asteraceae) is a widespread plant in Vietnam, and the species of Tithonia are known as plants containing many biologically active compounds. However, T. tagetiflora's chemical composition remains mostly unknown. Therefore, we now report the structural elucidation of two new sesquiterpene lactones, 8‐angeloyloxy‐2,14‐epoxygermacra‐4,10(1),11(13)‐trien‐6,12‐olide (1) and 6‐angeloyloxy‐1‐hydroxy‐3,4‐epoxygermacra‐9,11(13)‐dien‐8,12‐olide (2), together with three known compounds, including two norisoprenoids, (6S,9S)‐vomifoliol or (6R,9R)‐vomifoliol (3) and (6S,9S)‐roseoside (4), and one glutinane type triterpene, epi‐glutinol (5), from the leaves of T. tagetiflora. Their structures are established by 1D and 2D NMR spectroscopy, as well as ESI‐MS analysis and comparison with literature data. Copyright © 2013 John Wiley & Sons, Ltd.     

A new ent-clerodane diterpenoid from Crassocephalum bauchiense Huch. (Asteraceae)

A phytochemical investigation of the whole plant of Crassocephalum bauchiense Huch. resulted in the isolation of a new clerodane diterpenoid, ent-2β,18,19-trihydroxycleroda-3,13-dien-16,15-olide (1), together with two known flavonoids 3′,5-dihydroxy-4′,5′,6,7,8-pentamethoxyflavone (2) and 4′,5-dihydroxy-3′,5′,6,7,8-pentamethoxyflavone (3). The compounds were tested against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum. Compound 2 showed weak activity (IC₅₀ = 10.1 g/mL) whilst compounds 1 and 3 were inactive. The structures of the compounds were elucidated by using detailed spectral analyses, especially ¹H and ¹³C NMR, ¹H–¹H COSY, NOESY, HMBC and HR-ESI-MS.     

Complete NMR spectral assignments of two lactucin-type sesquiterpene lactone glycosides from Picris conyzoides

Complete (1)H and (13)C NMR signal assignments of two lactucin-type sesquiterpene lactone glycosides, derivatives of 11β,13-dihydrolactucin, isolated from roots of Picris conyzoides, were achieved by one- and two-dimensional NMR experiments, allowing the correction of previously published data for cichorioside B and the structure elucidation of its new ester with 3-hydroxy-2-methylpropanoic acid. In addition, seven known sesquiterpene lactones and three phenolic compounds were isolated from the plant material.     

Anticyanobacterial phenolic constituents from the aerial parts of Eupatorium fortunei Turcz

Four thymol derivatives and two phenolic compounds were isolated from the aerial parts of Eupatorium fortunei. The new structures were elucidated to be 7,8,9-trihydroxythymol (1), and 8,10-didehydro-7,9-dihydroxythymol (2) by means of MS and NMR analysis. The known compounds were identified as 8,9,10-trihydroxythymol (3), 10-acetoxy-8,9-dihydroxythymol (4), o-coumaric acid (5) and 4-(2-hydroxyethyl)benzaldehyde (6). Compound 3 showed strongest inhibitory effect on the growth of Microcystis aeruginosa in comparison with CuSO₄.     

The first two ecdysteroids containing a furan ring from Serratula wolffii

Two new ecdysteroids, named serfurosterone A and serfurosterone B, were isolated from a methanol extract of the roots of Serratula wolffii. Spectroscopic methods revealed that these compounds had previously unknown ecdysteroid structures with acetal functions in the side-chains.     

Cytotoxicity of an unprecedented brominated oleanolide and a new furoceramide from the Cameroonian spice,Echinops giganteus

A preliminary study on Echinops giganteus (Asteraceae) showed that the methanolic extract has interesting cytotoxicities against a panel of cancer cell lines. From this extract, a lignan, a flavonoid and a polyacetylenic thiophene identified were three times less cytotoxic than the extract. In the search of the metabolites responsible for the bioactivity, a new harvested E. giganteus was subjected to a phytochemical study using chromatographic methods. In the course of the work, two new compounds: a brominated oleanolide (1) and a tetrahydrofurano-ceramide (2) were obtained along with β-amyrin acetate (3), 2-(penta-1,3-diynyl)-5-(4-hydroxybut-1-ynyl)-thiophene (4), 2-(penta-1,3-diynyl)-5-(3,4-dihydroxybut-1-ynyl)-thiophene (5) and 4-hydroxy-2,6-di-(3′,4′-dimethoxyphenyl)-3,7-dioxabicyclo-(3.3.0)octane (6). Their structures were determined on the basis of NMR spectroscopy and mass spectrometry data in conjunction with those reported in the literature. The cytotoxicity of 1, 2 and 5 was evaluated by employing resazurin assay against a panel of cancer cell lines with IC₅₀ values in range 6.12 ± 0.46–46.96 ± 3.61 μM.