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Aerial parts of Carissa opaca have been investigated for the search of new bioactive secondary metabolites and a new nortriterpenoid: noropacursane (1) has been isolated together with three known compounds, namely, 6-methoxy-7-hydroxycoumarin (2), lupeol (3) and 4-ketopinoresinol (4). The structure of the new compound was established by 1D (¹H-, 13C-NMR), 2D-NMR (HMBC, HSQC, COSY and NOESY) and high resolution mass spectrometry (HR-EI-MS), where as the structures of the known compounds were elucidated through 1D-NMR, mass spectrometric analysis and compared with the reported data in literature. All the isolates were evaluated for their biological potential against the enzymes acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and lipoxygenase (LOX) as well as for DPPH free radical scavenging assays. Compound 4 was found active against DPPH radical scavenging activity and BChE with IC50 values of 83.41±0.17 and 101.81±0.24 μM, respectively, whereas compound 2 inhibited enzyme LOX with IC50 value of 102.25±0.17 μM. [ABSTRACT FROM AUTHOR]

The discovery of novel drugs against animal parasites is in high demand due to drug-resistance problems encountered around the world. Herein, the synthesis and characterization of 27 organic and organometallic derivatives of the recently launched nematocidal drug monepantel (Zolvix®) are described. The compounds were isolated as racemates and were characterized by 1H, 13C, and 19F NMR spectroscopy, mass spectrometry, and IR spectroscopy, and their purity was verified by microanalysis. The molecular structures of nine compounds were confirmed by X-ray crystallography. The anthelmintic activity of the newly designed analogues was evaluated in vitro against the economically important parasites Haemonchus contortus and Trichostrongylus colubriformis. Moderate nematocidal activity was observed for nine of the 27 compounds. Three compounds were confirmed as potentiators of a known monepantel target, the ACR-23 ion channel. Production of reactive oxygen species may confer secondary activity to the organometallic analogues. Two compounds, namely, an organic precursor ( 3 a) and a cymantrene analogue ( 9 a), showed activities against microfilariae of Dirofilaria immitis in the low microgram per milliliter range. [ABSTRACT FROM AUTHOR]

The ethyl acetate soluble fraction of the methanolic extract of Vincetoxicum stocksii yielded four new compounds; vincetolate (1), vincetoside (2), vincetetrol (3) and vincetomine (4) along with seven know compounds; 1-(4-hydroxy-3-methoxyphenyl)-1,2,3,-propanetriol (5), feruloyl-6-O-β-D-glucopyranoside (6), apocynin (7), 4-hydroxy-3,5-dimethoxybenzoic acid (8), 7- megastigmene-3,5,6,9-tetrol (9), qurcetin-3-O-β-D-glucopyranoside (10) and 4'- methoxykaempferol-3-O- β-D-glucopyranoside (11). The chemical structures of all the isolates were determined due to spectral analysis including sophisticated 1D- and 2D-NMR techniques and high resolution FABMS. Compounds 5-8 and 10 exhibited moderate to low antioxidant activity with IC50 values of 56.42±0.04-150±0.5 µg/ml whereas, compounds 1, 5 and 8-11 showed significant antiurease activity with IC50 values in the range of 22.1±0.43-105.47 ± 0.01µg/ml. [ABSTRACT FROM AUTHOR]

Chromatographic purification of the ethyl acetate soluble fraction from the methanolic extract ofAtriplex lasianthayielded a new triterpenoid, 7β,15α,16β-trihydroxyolean-12-ene-28,30-dioic acid-3-O-β-d-xylopyranoside (1), along with two known triterpenoids, rotundifolioside I (2) and corchorusin B (3). Structures of the compounds1–3were elucidated through sophisticated NMR studies and high resolution mass spectrometry. The three isolates (1–3) were evaluated for antibacterial, antioxidant, and antiurease activities. Compound2exhibited the best antibacterial activity againstEscherichiacoliwith IC50value of 66.25 μg/ml, whereas, all the tested compounds exhibited antioxidant (IC50values of 68.7–75.4 μg/ml) and antiurease (IC50values of 25.5–49.3 μg/ml) activities, respectively. [ABSTRACT FROM PUBLISHER]

Two new cryptosporioptide-derived polyketides cryptosporioptides A (2) and B (3) were isolated from the extract of endophytic fungus Cryptosporiopsis sp. associated with the shrub, Viburnum tinus. The structures of the isolates were determined through spectral analysis including 1D NMR (1H, 13C) and 2D NMR (HSQC, HMBC, COSY) techniques, HR-FAB-MS and by comparison with the reported data of cryptosporioptide (1). The relative stereochemistry was assigned with the help of NOESY analysis, the molecular model, and comparison of the optical rotation values with the reference compound 1. [ABSTRACT FROM AUTHOR]

Chromatographic purification of ethyl acetate soluble fraction of the methanolic extract of the flowers ofAerva javanicayielded three new acylated flavone glycosides: kaempferol-3-O-β-d-[4‴-E-p-coumaroyl-α-l-rhamnosyl(1 → 6)]-galactoside (1), kaempferol-3-O-β-d-[4‴-E-p-coumaroyl-α-l-rhamnosyl(1 → 6)]-(3″-E-p-coumaroyl)galactoside (2), and kaempferol-3-O-β-d-[4‴-E-p-coumaroyl-α-l-rhamnosyl(1 → 6)]-(4″-E-p-coumaroyl)galactoside (3), along withp-coumaric acid (4), caffeic acid (5), gallic acid (6), eicosanyl-trans-p-coumarate (7), hexadecyl ferulate (8), and hexacosyl ferulate (9). The compounds1–9were characterized using 1D (1H,13C) and 2D NMR (HMQC, HMBC, and COSY) spectroscopy and mass spectrometry (EI-MS, HR-EI-MS, FAB-MS, and HR-FAB-MS) and in comparison with the reported data in the literature. Compound1showed weak inhibitory activity against enzymes, such as acetylcholinesterase, butyrylcholinesterase, and lipoxygenase with IC50values 205.1, 304.1, and 212.3 μM, respectively, whereas compounds2and3were only weakly active against the enzyme acetylcholinesterase. [ABSTRACT FROM PUBLISHER]

Chromatographic separation of the ethyl acetate soluble part of the methanolic extract from Seriphidium stenocephalum yielded three new compounds: stenocepflavone (1), stenocepflavan (2), and stenocephol (3), together with cirsimaritin (4), 5,7,5′-trihydroxy-3′,4′,6-trimethoxyflavone (5), 5,6,7,5′-tetrahydroxy-4′-methoxyflavone (6), and axillaroside (7). All isolates were characterized with the help of spectroscopic data including 1D, 2D NMR, and high resolution mass spectrometry and/or in comparison with the related compounds in literature. All compounds were tested for in vitro enzyme inhibitory activities against acetylcholinesterase, butyrylcholinesterase, and lipoxygenase. Compounds 1 and 4–7 exhibited significant activity against all the tested enzymes, whereas compounds 2 and 3 were found inactive. [ABSTRACT FROM AUTHOR]

Bengalensinone (22β-hydroxylup-12,20-dien-3-one; 1), a new lupane triterpene, and benganoic acid (2), a new apocarotenoid, together with lupanyl acetate, 3-acetoxy-9(11),12-ursandiene, stigmasterol, alpinumisoflavone, 4-hydroxyacetophenone, 4-hydroxybenzoic acid, 4-hydroxymellein, and p-coumeric acid were isolated from the methanolic extract of the aerial roots of Ficus bengalensis. The structures of these compounds were established by the combination of 1D NMR (1H and 13C NMR) and 2D NMR (HMQC, HMBC, and COSY) analyses, and mass spectrometry (EI-MS and HR-EI-MS), and in comparison with literature data of the related compounds. Compounds 1 and 2 displayed inhibitory potential against enzyme cholinesterase in a concentration-dependent manner with IC50 values 194.5 and 154.5 μM for acetylcholinesterase and 224.9 and 120.0 μM for butyrycholinesterase, respectively. [ABSTRACT FROM AUTHOR]

Four new sphingolipids: nudicaulin A [(2S,3S,4R,14E)-2-{[octadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol; 1], nudicaulin B [(2S,3S,4R,14E)-2-{[(2R)-2-hydroxyoctadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol; 2], nudicaulin C [(2S,3S,4R,14E)-2-{[(2R)-2-hydroxyoctadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol-1-O-β-d-glucopyranoside; 3], and nudicaulin D [(2S,3S,4R)-2-{[(2R,3S,12E)-2,3-dihydroxyeicos-12-enoyl]amino}octadecane-1,3,4-triol; 4] together with 1-hexatriacontanol, β-sitosterol, octadecyl 4-hydroxycinnamate, elaidic acid, cholesta-5,22-diene-3,7-diol, oleanolic acid, apigenin, and β-sitosterol 3-O-β-d-glucopyranoside were isolated from the methanolic extract of the whole plant of Launaea nudicaulis. Their structures were elucidated using 1H and 13C NMR spectra and 2D NMR analyses (HMQC, HMBC, and COSY) in combination with mass spectrometry (EI-MS, HR-EI-MS, FAB-MS, and HR-FAB-MS) experiments and comparison with literature data of related compounds. Compounds 1–4 displayed moderate inhibitory potential against enzyme lipoxygenase in concentration-dependent manner with IC50 value ranges 103–193 μM. [ABSTRACT FROM AUTHOR]

Asphorins A and B ( 1 and 2, resp.), two new triterpene glycosides, have been isolated along with a new chromone, 3, from the AcOEt subfraction of the MeOH extract of the whole plant of Asphodelus tenuifolius. Their structures were elucidated by spectral analysis including 2D-NMR spectroscopic experiments. [ABSTRACT FROM AUTHOR]

Chromatographic purification of the methanolic extract of Plumeria obtusa yielded two new iridoid obtusadoids A (1) and B (2), along with eight known compounds plumieridin A (3), plumieridine (4), 1α-plumieride (5), 15-demethylplumieride (6), rel-(3R,3′S,4R,4′S)-3,3′,4,4′-tetrahydro-6,6′-dimethoxy[3,3′-bi-2H-benzopyran]-4,4′-diol (7), glochiflavanoside B (8), oleanolic acid (9), and methyl coumarate (10). The structures of all the isolates (1–10) were determined by NMR spectroscopy and mass spectrometry. The data of known compounds (3–10) were further compared with the reported data for these compounds. [ABSTRACT FROM PUBLISHER]

Chromatographic purification of the extract of an endophytic fungal culture yielded depsitinuside (1), a new phenolic ester together with ergosterol (2) and (22E,24S)-24-methyl-5-α-cholesta-7,22-diene-3β,5,6β-triol (3). The structure of 1 was elucidated based on 1D, 2D NMR spectroscopy and high-resolution mass spectrometry, whereas the known compounds (2 and 3) were identified by 1H NMR, mass spectrometry, and in comparison with the literature values. Compound 1 was evaluated for its enzyme inhibitory potential against acetylcholinesterase, butyrylcholinesterase and lipoxygenase, and was found inactive (10%–40% inhibition at a concentration of 2 mg/ml). [ABSTRACT FROM AUTHOR]

Abstract: A new series of fourteen numbers of organotin(IV) esters with NNDEG and NNDBG is being described. On the basis of IR, 1H-, 13C-NMR, Mass and Mössbauer spectroscopic studies and elemental analysis data, an interesting sinusoidal view of dimeric organotin(IV) is proposed and octahedral geometry is suggested for monomeric organotin(IV) esters while triorganotin(IV) complexes are assigned trigonal bipyramidal and tetrahedral geometry which is confirmed by 1H NMR. All the OTCs except 1, 4, 8 and 10 exhibited excellent rate of mortality against selected insects. OTCs (2, 6, 9, and 11) at 500ppm showed a two-fold positive role than standard drug Enoxacin as an antibiotic against the selected bacterial strains. ED50 of all OTCs is also reported here. The catalysis study of monomeric OTCs give 80% yield while dimeric OTCs give 100% yield of benzylacetate in six hours of reaction time. [ABSTRACT FROM AUTHOR]

The variety 'Shukri' is a new hybrid of Citrus sinensis and is frequently grown for its sweet edible fruits in the southern part of Pakistan. The leaves of this hybrid variety have been investigated in search of secondary metabolites for the first time. As a result of chromatographic analysis of the methanolic extract, a new ceramide along with a flavonone glycoside and two steroids has been isolated, which were spectroscopically characterized as (E)-N-(1,3,4,5-tetrahydroxyhexadecan-2-yl)dec-4-enamide (1), atripliside B (2), β-sitosterol (3), and β-sitosterol-3-O-β-D-glucopyranoside (4), respectively. Compound 1 was found to be a new addition in the list of natural products, whereas, to the best of our knowledge, compounds 2-4 have been isolated for the first time from this source. [ABSTRACT FROM AUTHOR]

Species of the genus Phyllanthus are known for their medicinal values and many are explored phytochemically. Some of them produce phthalates which usually have antimicrobial properties. This paper deals with the phytochemical investigation on Phyllanthus muellerianus. As a result, five compounds, bis(2-ethyloctyl)phthalate (1), bis(2-ethylicosyl)phthalate (2), 3-friedelanone (3), β-sitosterol (4), and methyl gallate (5), have been isolated and characterized. Metabolites 1 and 2 are new compounds, while 3-5 have been isolated for the first time from this source. Structures of all the isolates were established on the basis of MS, 1D and 2D NMR spectral data and in comparison with the reported data. [ABSTRACT FROM AUTHOR]