Highly oxygenated guaianolides and eudesman-12-oic acids from Balsamorhiza sagittata and Balsamorhiza macrophylla.
Investigation of lipophilic exudates from the aerial parts of Balsamorhiza sagittata and B. macrophylla afforded three new highly oxygenated guaianolides (1-3), in addition to known guaianolides, germacranolide and eudesmane acids. Their chemical structures were elucidated by spectroscopic methods and the data for the compounds are reported in Tables 1 and 2 and in Experimental. (+info)
Medical benefits of using natural compounds and their derivatives having multiple pharmacological actions.
The multiple pharmacological actions of a unique compound are a prerequisite for classifying drugs as highly efficacious, because the multiple pharmacological actions offer the possibility of treating various symptoms of chronic diseases as described below. 1) Sustained hyperglycemia induces macrovascular and microvascular complications in type 2 diabetes mellitus. Antihyperglycemic medication and the control of postprandial hyperglycemia are essentially important for normalizing plasma glucose level. Gymnemic acid IV isolated from Gymnema sylvestre (Asclepiadaceae) leaves has antisweet, antihyperglycemic, glucose uptake inhibitory, and gut glycosidase inhibitory effects. Most of these pharmacological effects may synergistically contribute to alleviating type 2 diabetes-related symptoms. 2) Diabetic skeletal and vascular smooth muscles are hypersensitive to chemical transmitters, cytokines and autacoids. The sensitivity of neuromuscular synapses is enhanced in diabetes, which seems to be closely associated with neuropathy as one of the diabetic complications. beta-Eudesmol found in Atractylodes lancea rhizome has a desensitizing channel blocking action to nicotinic acetylcholine receptors, anti-angiogenic action in vascular endothelium, and neuronal differentiation actions. These multiple pharmacological actions are favorable for treating angiogenic diseases possibly including the complications of diabetes, namely, retinopathy and nephropathy, and cancer. 3) Nipradilol is clinically utilized as a topical antiglaucoma drug. The ocular hypotensive effects of this compound are brought about by its alpha1 and beta-adrenergic receptor blocking actions, and nitric oxide (NO) releasing action. NO directly activates cyclooxygenases. All these pharmacologic effects are beneficial for treating glaucoma. The selectivity and specificity of drug action are required for treating acute diseases, infections or for acting as useful reagents. The pleiotropic actions of natural compounds and their derivatives serve as important clues for developing new drugs for various chronic diseases. (+info)
Pimarane diterpenes and a sesquiterpene from Salzmmania nitida.
Two new terpenoids, (+)-3-oxo-thermarol and 11-acetoxyeudesman-4alpha-methyl-5alpha-ol along with the (+)- thermarol were isolated from the aerial parts of Salzmmania nitida. The structures and unambiguous 1H and 13C chemical shift assignments were established by spectroscopic means, including homo and heteronuclear techniques. (+info)
A new eudesmane derivative and a new fatty acid ester from Sambucus williamsii.
1,4,13-Trihydroxy-eudesm-11(12)-ene, a new eudesmane derivative (3), (9E)-8,11,12-trihydroxyoctadecenoic acid methyl ester, a new fatty acid ester (2) and tianshic acid (1) were obtained from the stems of Sambucus williamsii. Their structures were elucidated by physiochemical properties and spectroscopic analysis. Both compounds 1 and 2 showed stimulating effects on alkaline phosphatase activity of the osteoblastic UMR106 cell about 1.5 fold at 30 mumol/l while they had no effects on cell proliferation. (+info)
Antioxidant and alpha-amylase inhibitory compounds from aerial parts of Varthemia iphionoides Boiss.
Various extracts of aerial parts of Varthemia (Varthemia iphionoides Boiss) were investigated for radical-scavenging activity, antioxidative activity, and porcine pancreas alpha-amylase inhibitory activity. The ethanol and water extracts showed a pronounced 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity, with inhibition of about 90% at a concentration of 100 microg/ml, and alpha-amylase inhibitory activity of about 70% at a concentration of 200 microg/ml by the 2-chloro-4-nitrophenyl alpha-maltotrioside (CNP-G3) degradation method. The ethanol extract was purified by column chromatography to give seven 3-methoxyflavones (1-7) and eudesmane sesquiterpene, selina-4,11(13)-dien-3-on-12-oic acid (8). The structures of these compounds were established by NMR, MS, and UV spectroscopy. Of 3-methoxyflavones, 5,7,4'-trihydroxy-3,6-dimethoxyflavone (1), 5,7,4'-trihydroxy-3,3'-dimethoxyflavone (2), and 5,4'-dihydroxy-3,7,3'-trimethoxyflavone (3,7,3'-tri-O-methyl-quercetin) (7) exhibited pronounced radical-scavenging activity. The antioxidative activity in the linoleic acid system was considerable in compounds 1, 2, and 5,4'-dihydroxy-3,6,7-trimethoxyflavone (4). Compounds 1, 2, 4, 5 (5,7,4'-trihydroxy-3-methoxyflavone), and 6 (5,4'-dihydroxy-3,7-dimethoxyflavone) showed markedly high inhibitory activity against porcine pancreas alpha-amylase. Eudesmane sesquiterpene did not show any activity. (+info)
Two minor diterpene glycosides and an eudesman sesquiterpene from Coleus forskohlii.
Two new labdane diterpene glycosides, forskoditerpenosides A, B (1, 2) and a new eudesmane sesquiterpene, 4beta,7beta,11-enantioeudesmantriol (3), were isolated from the ethanol extract of the whole plant of Coleus forskohlii. Their structures and stereochemistry were elucidated by extensive spectroscopic analysis and chemical methods. The structure of compound 3 was confirmed by X-ray diffraction. This is the first report about the occurrence of glycosides derived from the kind of labdane diterpene, 8,13-epoxy-labd-14-en-11-one, in the nature. Compounds 1 and 2 showed relaxative effects on isolated guinea pig tracheal spirals in vitro. (+info)
Isolation and functional characterization of a beta-eudesmol synthase, a new sesquiterpene synthase from Zingiber zerumbet Smith.
New eudesmane derivatives and other sesquiterpenes from the epigeal parts of Dittrichia graveolens.
In bioassay-guided searches for novel bioactive natural products from higher plants of the Egyptian flora, two new eudesmane sesquiterpene derivatives, 3alpha-hydroxyilicic acid methyl ester (1) and 2alpha-hydroxy-4-epi-ilicic acid (2), together with 11 known sesquiterpenes were isolated from bioactive fractions of the active epigeal parts extracts of Dittrichia graveolens (L.) GREUTER (Asteraceae) growing in the coastal regions of northwestern Egypt. Four other known sesquiterpene lactones with different carbon skeletons, named 2alpha-hydroxy-2R-xanthalongin (8), 4-epi-isoinuviscolide (9), 8-epi-helenalin (10), and bigelovin (11), were also isolated for the first time from the same source. The stereochemical structures of the isolated compounds were elucidated on the basis of physical and spectroscopic methods including UV, IR, 1H-, 13C-NMR, distortionless enhancement by polarization transfer, 2D NMR, 1H-1H correlation spectroscopy, 1H-13C heteronuclear single-quantum coherence, 1H-13C heteronuclear multiple-bond connectivity, 1H-1H nuclear Overhauser effect spectroscopy experiments, and high-resolution mass spectrometry, as well as some chemical transformations. The antimicrobial, antiinflammatory, and antipyretic activities of D. graveolens extracts and chromatographic fractions were carried out and the various bioactivities of our findings are discussed. (+info)