The anti-inflammatory properties of phenolic pine (Pinus sylvestris L.) bark extract were studied. The pine bark extract was fractionated by liquid-liquid extractions and semipreparative high-performance liquid chromatography to reveal the most potent constituents. The phenolic compositions of three pine bark samples obtained, a crude extract, a chloroform fraction, and a semipreparative fraction, were analyzed using high-performance liquid chromatography with UV diode array detection and/or electrospray ionization mass spectrometry. In addition, eight compounds were isolated and identified by NMR and MS techniques. In total 28 phenolic compounds were identified. The effects of the three pine bark samples on the synthesis of two proinflammatory mediators, nitric oxide and prostaglandin E(2), were measured. It was shown that pine bark contains compounds that inhibit the production of these proinflammatory mediators.
A previously isolated cDNA molecule from Gerbera hybrida (Asteraceae) codes for a new chalcone synthase-like polyketide synthase, 2-pyrone synthase (2PS). 2PS is able to synthesise 4-hydroxy-6-methyl-2-pyrone (triacetolactone), a putative precursor for gerberin and parasorboside, two abundant glucosides in gerbera. In this study, we show that gerbera plants transformed with the gene for 2PS in an antisense orientation and unable to synthesise gerberin and parasorboside are susceptible to Botrytis cinerea infection. In addition to the preformed glucosides, the transgenic plants also lack several compounds that are induced in control plants when infected with the mould. Some of these induced substances are effective in inhibiting fungal growth both in vitro and in vivo. Two of the phytoalexins were identified as the aglycones of gerberin and trans-parasorboside. The third phytoalexin is a rare coumarin, 4-hydroxy-5-methylcoumarin; however, it is typical of many plants of the sunflower family Asteraceae. The coumarin cannot be structurally derived from either gerberin or parasorboside, but may be derived from a related polyketide intermediate.
Treatment of 1-hydroxy-2,3-dihydro-1H-pyrazolo[1,2-a]pyridazine-5,8-diones and -1H-pyrazolo[1,2-b]phthalazine-5,10-diones with hydrazides produces corresponding acylhydrazino derivatives. In this work, ten new hydrazino derivatives were synthesized, and their properties were studied by 1 H and 13 C NMR spectroscopy. These compounds exhibited several types of structural variation, including ring-chain tautomerism, cis-trans isomerism with respect to the substituents in the pyrazole ring, and (E)/(Z) rotamerism with respect to the nitrogen−carbon hydrazide bond with partial double-
The essential oils obtained from the buds of Betula pubescens ssp. pubescens and B. pubescens ssp. czerepanovii were analyzed both by GC and GC/MS and, of the 31 compounds identified, 14-acetoxy-β-caryophyllene was determined to be the main component in both oils in addition to 25 other previously known compounds. Three of the compounds were isolated from the oils and further characterized by NMR spectroscopy and mass spectrometry, including a new bicyclic aldehyde (4,8,8-trimethyl-2-methylenebicyclo[-5.2.0]nonane-4-carbaldehyde, birkenal), a new tricyclic lactone (1,4,4,8-tetramethyl-10-oxatricyclo[6.2.1.0 2,5 ]undecan-9-one, hushinone), and the recently described 6-hydroxycaryophyllene. The isolation of birkenal also enabled identification of its corresponding alcohol { (4,8,8-trimethyl-2-methyl-
The molluscicidal activity of leaf and rhizome extracts of Iris germanica L. (var. alba) against Biomphalaria alexandrina snails was evaluated and the rhizome extracts were found to be the most potent. Activity-guided fractionation revealed that the chloroform extract showed the highest molluscicidal activity (LC90 = 1.26 mg/l) among the tested extracts of the rhizomes. Fraction B prepared from the chloroform extract was the most potent molluscicide (LC90 = 0.96 mg/l) in addition, it showed a significant heart rate reduction in the snail after a 6- to 24-h exposure period. It also displayed a significant level of cercaricidal potential in a time-concentration relationship pattern. Chromatographic fractionation and purification of fraction B resulted in the isolation of two novel compounds: 5,2′-dihydroxy-3-methoxy-6,7- methylenedioxyflavone and 5,7,2′-trihydroxy-6-methoxyflavanone. Their structures were established by one- and two-dimensional NMR methods and mass spectrometry
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