Styryllactones from Goniothalamus tamirensis.

The phytochemical investigation of the twig and leaf extracts of Goniothalamus tamirensis led to the isolation and identification of 15 compounds including three rare previously undescribed styryllactones, goniotamirenones A-C, together with 12 known compounds. (Z)-6-Styryl-5,6-dihydro-2-pyranone and 5-(1-hydroxy-3-phenyl-allyl)-dihydro-furan-2-one are reported here for the first time as previously undescribed natural products. Their structures were elucidated by spectroscopic methods. Goniotamirenone A was synthesized via a [2 + 2] cycloaddition reaction of 6-styrrylpyran-2-one in quantitative yield. The absolute configurations of goniotamirenones B and C were identified from experimental and calculated ECD data, while the absolute configurations of (-)-5-acetoxygoniothalamin, (-)-isoaltholactone, parvistone E, and 5-(1-hydroxy-3-phenyl-allyl)-dihydro-furan-2-one were identified by single-crystal X-ray diffraction analysis using Cu Kα radiation. The absolute configurations of the other related compounds were determined from comparisons of their ECD spectra with relevant compounds reported in the literature. (-)-5-Acetoxygoniothalamin exhibited potent cytotoxicity against the colon cancer cell line (HCT116) with an IC50 value of 8.6 µM which was better than the standard control (doxorubicin, IC50 = 9.7 µM), while (Z)-6-styryl-5,6-dihydro-2-pyranone was less active with an IC50 value of 22.1 µM.

Characteristic Scent from the Tahitian Liverwort, Cyathodium foetidissimum.

The volatile components of the Tahitian liverwort Cyathodium foetidissimum was analyzed using headspace solid phase micro-extraction (SPME) and GC-MS. Three volatile components, 4-methoxystyrene (24.4%), 3,4-dimethoxystyrene (28.7%), and skatole (15.9%) were identified as the major components from the fresh C. foetidissimum, along with several aliphatic aldehydes, n-octanal, n-nonanal, and n-decanal. However, (E)-2-nonenal recognized as aged malodor was not identified. In GC-O analysis, 2-aminoacetophenone was detected as one of the minor components with a strong aging note. In fact, C. foetidissimum showed the characteristic aging odor reminiscent the damp smell from old chest of drawers, or the civet like note with very strong feces and urine odor. The mixture consisted of 4-methoxystyrene, 3,4-dimethoxystyrene, and skatole in the detected ratio showed the sedative effect on CNV (contingent negative variation) measurement.

Phenolic Compounds of Inonotus rheades (Agaricomycetes) Mycelium: RP-UPLC-DAD-ESI/MS Profile and Effect of Light Wavelength on Styrylpyrone Content.

The phenolic compounds of Inonotus rheades (Pers.) Bondartsev and Singer (Hymenochaetaceae), a typical xylotrophic basidiomycete, and accumulation of styrylpyrones in mycelium under the influence of light of different wavelengths were investigated. Six styrylpyrones (cis- and trans-hispidin, cis- and trans-bisnoryangonin, and phellinins A1 and A2) and 5 bis(styrylpyrones) (3,14'-bishispidinyl, hypholomin B, 3-bisnoryangonyl-14'-hispidin, 1,1-distyrylpyrylethane, and rheadinin) were detected in the extract of I. rheades mycelium using reversed phase ultra-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry (RP-UPLC-DAD-ESI/MS). The results showed that the maximal content of styrylpyrones was observed under the influence of blue light (8.10 mg/g of dry mycelium weight). Moreover, hispidin was the dominant compound in all experimental groups. Pigmentation intensity gradually decreased after shifting the light spectrum into darkness. It can be concluded that cultivation of I. rheades mycelium under the blue part of the light spectrum leads to the accumulation of styrylpyrones that have nutraceutical and medicinal significance.

[A new styrene dimer derivative from Litsea greenmaniana].

A new styrene dimer derivative has been isolated from the branch of Litsea greenmaniana by column chromatography over silica gel and Sephadex LH-20, as well as semi-preparative HPLC. Its structure was identified by spectroscopic data analysis (MS, UV, IR, 1D and 2D NMR) as (E)-2,4-bis(p-hydroxyphenyl)-2-butenol, named as listeanol. At a concentration of 1×10-5 mol•L⁻¹, compound 1 was inactive in the assays, including cytotoxicity against human tumor cell lines (HCT-8, Bel-7402, BGC-823, A549 and A2780), antioxidant activity in Fe²âº-cystine-induced rat liver microsomal lipid peroxidation, neuroprotective activity against serum deprivation or glutamate induced neurotoxicity in cultures of PC12 cells, and the inhibitory activity against protein tyrosine phosphatase 1B (PTP1B).

Dihydrogoniothalamin, an Endothelium and NO-Dependent Vasodilator Drug Isolated from Aniba panurensis.

Dihydrogoniothalamin is a styrylpyrone isolated from the leaves of Aniba panurensis. The present work aimed at investigating the vasorelaxant activity of dihydrogoniothalamin and its underlying mechanism of action in the rat aorta. Dihydrogoniothalamin (0.01-100 µM) induced a concentration-dependent vasodilatation of aortas precontracted with phenylephrine. Endothelium removal or pretreatment of the preparation with NG nitro-L-arginine-methyl-ester abolished the vasodilator response for dihydrogoniothalamin. Pretreatment with calmidazolium did not affect the vasodilator response of dihydrogoniothalamin. On the other hand, wortmannin, a nonselective inhibitor of phosphatidylinositol 3-kinases, and protein kinase B inhibitor IV significantly shifted the concentration-response curve of dihydrogoniothalamin to the right and reduced its maximal effect. A nonselective antagonist of estrogen receptors, ICI 182,780, and a selective antagonist of estrogen receptor α, methyl-piperidino-pyrazole, were able to reduce the relaxation induced by dihydrogoniothalamin, but no effect was observed in the presence of the selective antagonists of estrogen receptor ß and G protein-coupled receptor 30, 4-[2-phenyl-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]phenol (PHTPP), and G-15, respectively. Dihydrogoniothalamin also increased the phosphorylation of the activation sites of endothelial nitric oxide synthase and protein kinase B. The present results led us to conclude that dihydrogoniothalamin is a vasodilator drug acting in an endothelium- and nitric oxide-dependent manner through a mechanism involving the activation of nitric oxide synthase via the phosphatidylinositol 3-kinase/protein kinase B pathway, partially by stimulation of estrogen receptor α.

Larvicidal activity of lansiumamide B from the seeds of Clausena lansium against Aedes albopictus (Diptera: Culicidae).

The larvicidal activity of crude petroleum ether, toluene, n-butanol, ethyl acetate, acetone, and methanol extracts of the seeds of Clausena lansium was assayed for their toxicities against the early fourth instar larvae of Aedes albopictus. The larval mortality was observed after 24-h exposure. The LC(50) value of petroleum ether extract was 22.99 ppm, showing the best larvicidal activity among all six solvent extracts. A cinnamon amide compound lansiumamide B (N-methyl-N-cis-styrylcinnamamide) was isolated from the petroleum ether extract by column chromatographic method, which exhibited a strong larvicidal activity against the early fourth instar larvae of A. albopictus with LC(50) and LC(90) values of 0.45 and 2.19 ppm, respectively. The structure was elucidated by (1)H NMR, (13)C NMR spectral data. The larvicidal activity against mosquito of lansiumamide B from the seed of C. lansium was evaluated for the first time.

Alkaloid and sesquiterpenes from the root tuber of Curcuma longa.

One new quinoline alkaloid and seven known bisabolane sesquiterpenes: 2-(2'-methyl-1'-propenyl)-4, 6-dimethyl-7-hydroxyquinoline (1), 2, 5-dihydroxybisabola-3, 10-diene (2), 4, 5-dihydroxybisabola-2,10-diene (3), turmeronol A (4), bisacurone (5), bisacurone A (6), bisacurone B (7) , bisacurone C (8), as well as dehydrozingerone (9) and zingerone (10) were isolated from the root tuber of Curcuma longa. Their structures were identified by spectral evidence. Compound 1 is a new compound, compounds 6 -8 were isolated from this plant for the first time and compounds 9 - 10 from Curcuma for the first time.

[Studies on chemical constitutes of Acantophora spicifera].

OBJECTIVE: To study the chemical constitutes of Acantophora spicifera. METHOD: Compounds were isolated by normal phase silica gel and Sephadex LH-20 gel column chromatography, and reverse-phase HPLC, as well as recrystallization. Their structures were elucidated by spectroscopic methods. RESULT: Seven compounds were isolated from A. spicifera and their structures were identified as aplysin (1), loloilide (2), (R)-(-)-dehydrovomifoliol (3), uracil (4), thymine (5), 1-methoxy-4-(1-propenyl) benzene (6). CONCLUSION: The compounds were obtained from this genus for the first time. Compound 6 was firstly obtained from marine organisms.

Determination of active components in rhubarb and study of their hydrophobicity by micellar electrokinetic chromatography.

A micellar electrokinetic chromatographic (MEKC) method has been developed for the determination of five anthraquinones and one distyrene derivative in rhubarb. The separation conditions were optimized and two kinds of rhubarb plants and rhubarb-containing medicines were analyzed. The negatively charged solutes migrated toward the anode and were retarded by their interaction with the micelle. Hydrophobicity of the solutes was studied by both MEKC with SDS and SDS-free capillary zone electrophoresis in the buffer of 15 mmol/L NaH(2)PO(4)+ 20 mmol/L borax and 15% ethanol (v/v). Linear correlation between log k' and log P(OW) was obtained for the five anthraquinones in SDS micelle system. The capacity factor, k', and free energy differences delta(deltaG) derived from this method provided fundamental information on the interaction between the solutes and the micelle.

Identification of major water-soluble fluorescent components of some petrochemicals.

The chemical identities of several organic compounds that dominate the ultraviolet (UV) fluorescence of water after exposure to gasoline, diesel fuel and crude oil are presented. A combination of high-performance liquid chromatography with UV-fluorescence detection, fluorescence spectroscopy and gas chromatography-mass spectrometry (GC-MS) is used to show that naphthalene, methylnaphthalene and methylstyrene are the major fluorescent species in water following exposure to gasoline. These compounds are not dominant in water exposed to other petrochemicals we studied.

3-acetylaltholactone and related styryl-lactones, mitochondrial respiratory chain inhibitors.

A novel furano-pyrone, 3-acetylaltholactone, and two other known styryl-lactones, altholactone and 5-acetoxyisogoniothalamin oxide, have been isolated from Goniothalamus arvensis (Annonaceae) stem bark. We report here the isolation and structural elucidation of these compounds with furane-pyrone and styryl-pyrone skeletons, postulating also for the first time their mechanism of cytotoxicity based on inhibition on mammalian mitochondrial respiratory chain.

Bioactive amides from Glycosmis species.

Besides the known imide ritigalin (9), six new phenethyl/styrylamine-derived amides isolated from lipophilic leaf extracts of Glycosmis cf. mauritiana, Glycosmis cf. cyanocarpa, and Glycosmis crassifolia displayed pronounced antifungal and/or insecticidal activity against Cladosporium herbarum and Spodoptera littoralis, respectively, the methylthiocarbonic acid derivatives niranin (1), dehydroniranin A (2), and dehydroniranin B (3) as well as the isovaleric and senecioic acid derivatives thalebanin B (4), dehydrothalebanin B (5), and dehydrothalebanin A (6).

Two new aromatic constitutents from the rootwood of Aeschynomene mimosifolia.

The rootwood of Aeschynomene mimosifolia Vatke (Leguminosae) has yielded a new neoflavonoid, mimosifoliol (1), and an unusual C16-styrylcycloheptenone derivative, mimosifolenone (2). The structures of these compounds were determined on the basis of spectral analysis. Compound 1 demonstrated weak activity in DNA-strand scission assay, while compound 2 was found to be inactive. Mimosifoliol (1) was inactive toward several human cell lines, while 2 was moderately active against the KB cell line.

The crystal structure and cytotoxicity of goniodiol-7-monoacetate from Goniothalamus amuyon.

The styrylpyrone, goniodiol-7-monoacetate [1] [6R-(7R,8R-dihydro-7-acetoxy-8-hydroxystyryl)-5, 6-dihydro-2-pyrone], has been isolated from Goniothalamus amuyon, and its detailed molecular structure has been determined by X-ray crystallographic analysis. Goniodiol-7-monoacetate showed potent (ED50 values less than 0.1 microgram/ml) cytotoxicities against KB, P-388, RPMI, and TE671 tumor cells.