Unusual pyranosyl cembranoid diterpene from Sarcophyton trocheliophorum

2016 ◽  
Vol 71 (12) ◽  
pp. 1211-1217 ◽  
Author(s):  
Mohamed Shaaban ◽  
Mohamed A. Ghani ◽  
Khaled A. Shaaban
Keyword(s):  
Quantum Coherence ◽  
Soft Coral ◽  
High Resolution Mass Spectrometry ◽  
Nuclear Overhauser Effect ◽  
Multiple Bond ◽  
2D Nmr ◽  
Correlation Spectroscopy ◽  
Multiple Quantum ◽  
Chemical Structures ◽  
Sarcophyton Trocheliophorum

Abstract9-Hydroxy-10,11-dehydro-sarcotrocheliol (1), a new pyrane-based cembranoid diterpene, has been isolated along with three other known compounds, namely, sarcotrocheliol acetate (2), (+)-sarcophytol A (3), and (−)-sarcophytonin A (4), from the organic extract of the soft coral Sarcophyton trocheliophorum. The chemical structures of compounds 1–4 were determined on the basis of their 1D and 2D NMR [1H, 13C, 1H–1H correlation spectroscopy, heteronuclear multiple-quantum coherence, heteronuclear multiple-bond correlation, and nuclear Overhauser effect (NOE)] and mass spectra [electron ionization (EI), electrospray ionization, and high resolution mass spectrometry (HRMS)], and by comparison with related structures. The compounds 1–4 showed neither antimicrobial activity against 11 diverse tested microorganisms, nor cytotoxicity against brine shrimp, whereas the soft coral extract showed low cytotoxicity with a mortality rate of 1.7%.

The isolation and structural elucidation of a new iridoid glycoside from Cymbaria dahurica L.

2018 ◽  
Vol 73 (6) ◽  
pp. 377-379 ◽  
Author(s):  
Cui-Lan Bai ◽  
Qing-Hu Wang ◽  
Yan-Hua Xu ◽  
Jun-Sheng Han ◽  
Yin-Ping Bao
Keyword(s):  
Quantum Coherence ◽  
Nuclear Overhauser Effect ◽  
Multiple Bond ◽  
2D Nmr ◽  
Iridoid Glycoside ◽  
Correlation Spectroscopy ◽  
Etoac Extract ◽  
Overhauser Effect ◽  
Nuclear Overhauser ◽  
C Nmr

AbstractA new iridoid glycoside, namely, cymdahoside A (1), together with two known ones, 2 and 3, were isolated from the EtOAc extract of Cymbaria dahurica. The structure elucidation of 1 was carried out by one-dimensional (1D) NMR (1H and 13C NMR) and 2D NMR (correlation spectroscopy, heteronuclear single-quantum coherence, heteronuclear multiple-bond correlation and nuclear Overhauser effect spectroscopy) spectral analyses.

scholarly journals Bioassay-Guided Isolation and Structure Elucidation of Fungicidal and Herbicidal Compounds from Ambrosia salsola (Asteraceae)

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 835 ◽  
Author(s):  
Wilmer H. Perera ◽  
Kumudini M. Meepa ◽  
Frank R. Fronczek ◽  
Daniel D. Cook ◽  
David E. Wedge ◽  
...  
Keyword(s):  
Quantum Coherence ◽  
High Resolution Mass Spectrometry ◽  
Sesquiterpene Lactones ◽  
Multiple Bond ◽  
Direct Analysis ◽  
Double Quantum ◽  
Multiple Quantum ◽  
Spectra Analysis ◽  
Quercetin Derivatives ◽  
Chemical Structures

The discovery of potent natural and ecofriendly pesticides is one of the focuses of the agrochemical industry, and plant species are a source of many potentially active compounds. We describe the bioassay-guided isolation of antifungal and phytotoxic compounds from the ethyl acetate extract of Ambrosia salsola twigs and leaves. With this methodology, we isolated and identified twelve compounds (four chalcones, six flavonols and two pseudoguaianolide sesquiterpene lactones). Three new chalcones were elucidated as (S)-β-Hydroxy-2′,3,4,6′-tetrahydroxy-5-methoxydihydrochalcone (salsolol A), (S)-β-Hydroxy-2′,4,4′,6'-tetrahydroxy-3-methoxydihydrochalcone (salsolol B), and (R)-α, (R)-β-Dihydroxy-2′,3,4,4′,6′- pentahydroxydihydrochalcone (salsolol C) together with nine known compounds: balanochalcone, six quercetin derivatives, confertin, and neoambrosin. Chemical structures were determined based on comprehensive direct analysis in real time-high resolution mass spectrometry (HR-DART-MS), as well as 1D and 2D NMR experiments: Cosy Double Quantum Filter (DQFCOSY), Heteronuclear Multiple Quantum Coherence (HMQC) and Heteronuclear Multiple Bond Coherence (HMBC), and the absolute configurations of the chalcones were confirmed by CD spectra analysis. Crystal structure of confertin was determined by X-ray diffraction. The phytotoxicity of purified compounds was evaluated, and neoambrosim was active against Agrostis stolonifera at 1 mM, while confertin was active against both, Lactuca sativa and A. stolonifera at 1 mM and 100 µM, respectively. Confertin and salsolol A and B had IC50 values of 261, 275, and 251 µM, respectively, against Lemna pausicotata (duckweed). The antifungal activity was also tested against Colletotrichum fragariae Brooks using a thin layer chromatography bioautography assay. Both confertin and neoambrosin were antifungal at 100 µM, with a higher confertin activity than that of neoambrosin at this concentration.

scholarly journals One New Royleanumoate fromTeucrium royleanumWall. ex Benth

2014 ◽  
Vol 2014 ◽  
pp. 1-3
Author(s):  
Shabir Ahmad ◽  
Riaz Ullah ◽  
Naser M. AbdElsalam ◽  
Hassan Fouad ◽  
Ahtaram Bibi ◽  
...  
Keyword(s):  
Structure Elucidation ◽  
Quantum Coherence ◽  
Multiple Bond ◽  
2D Nmr ◽  
Correlation Spectroscopy ◽  
Multiple Quantum ◽  
Heteronuclear Multiple Bond Correlation ◽  
Heteronuclear Multiple Quantum Coherence ◽  
Nmr Techniques ◽  
Multiple Quantum Coherence

One new royleanumoate, a benzene ester (1), has been isolated fromT. royleanumWall. ex Benth along with two known compounds, namely, 3,4-dihydroxymethyl benzoate (2) and oleanolic acid (3). The structure elucidation of the isolated compounds was established on two-dimensional (2D) NMR techniques including heteronuclear multiple bond correlation (HMBC), heteronuclear multiple quantum Coherence (HMQC), and correlation spectroscopy (COSY) experiment.

Nepetolide: A New Diterpene from Nepeta suavis

2008 ◽  
Vol 63 (5) ◽  
pp. 591-594 ◽  
Author(s):  
Javid Hussain ◽  
Farman Ullah ◽  
Hidayat Hussain ◽  
Tasleem Hussain ◽  
M. Raza Shah
Keyword(s):  
Structure Elucidation ◽  
Quantum Coherence ◽  
Multiple Bond ◽  
2D Nmr ◽  
Correlation Spectroscopy ◽  
Multiple Quantum ◽  
Heteronuclear Multiple Bond Correlation ◽  
Heteronuclear Multiple Quantum Coherence ◽  
Nmr Techniques ◽  
Multiple Quantum Coherence

A new tricyclic clerodane-type diterpene, nepetolide (1), has been isolated from Nepeta suavis along with three known compounds namely β -sitosterol, stigmasterol, and ursolic acid. The structure elucidation of the isolated compounds was based primarily on two-dimensional (2D)-NMR techniques including correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond correlation (HMBC) experiments.

Sesquiterpenes from the Saudi Red Sea: Litophyton arboreum with their cytotoxic and antimicrobial activities

2018 ◽  
Vol 73 (1-2) ◽  
pp. 9-14 ◽  
Author(s):  
Lamia T. Abou El-Kassem ◽  
Usama W. Hawas ◽  
Samy K. El-Desouky ◽  
Radwan Al-Farawati
Keyword(s):  
Red Sea ◽  
Quantum Coherence ◽  
Nuclear Overhauser Effect ◽  
Multiple Bond ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
Correlation Spectroscopy ◽  
Coherence Spectroscopy ◽  
Nuclear Overhauser

AbstractA new pseudoguaiane-type sesquiterpene named litopharbol (1) was isolated from the methanolic extract of the Red Sea soft coralLitophyton arboreum, along with known sesquiterpenoids alismol (2), alismorientol B (3), teuhetenone A (4), and calamusin I (5); steroid, 24-methyl-cholesta-5,24(28)-diene-3β-ol (6), alkyl glyceryl ether, chimyl alcohol (7); sphingolipid, erythro-N-dodecanoyl-docosasphinga-(4E,8E)-dienine (8); and nitrogenous bases, thymine (9) and thymidine (10). The structures were determined on the basis of nuclear magnetic resonance (NMR) spectroscopic (1D and 2D NMR data including heteronuclear single quantum coherence spectroscopy, heteronuclear multiple-bond correlation spectroscopy, and nuclear Overhauser effect spectroscopy) and mass spectrometric analyses. Compounds1–5were explored for antimicrobial activity and cancer cell line sensitivity tests. Compound1exhibited antibacterial activity againstBacillus cereuswith a minimum inhibition concentration of 1.8 μg/mL, whereas compound3showed significant potent cytotoxic effect against MCF-7 (breast cancer cells) with IC504.32 μM.

Two-dimensional NMR studies of acrylate copolymers

2009 ◽  
Vol 81 (3) ◽  
pp. 389-415 ◽  
Author(s):  
A. S. Brar ◽  
Ashok Kumar Goyal ◽  
Sunita Hooda
Keyword(s):  
Methyl Methacrylate ◽  
Methyl Acrylate ◽  
Quantum Coherence ◽  
Multiple Bond ◽  
Microstructural Analysis ◽  
2D Nmr ◽  
Correlation Spectroscopy ◽  
Nmr Studies ◽  
Poly Methyl Methacrylate ◽  
Nmr Study

High-resolution NMR spectroscopy is the most versatile, reliable, and generally acceptable technique for the determination of the microstructure of polymers. 2D NMR techniques, along with 1D NMR, have more potential to study absolute configurational assignments and sequence distribution of copolymers. Physical and chemical properties of polymers are influenced fundamentally by their microstructure. We discuss the detailed microstructure analysis of a large number of homopolymers, copolymers, and terpolymers. 2D NMR study of poly(methyl methacrylate) (PMMA), poly(methyl acrylate) (PMA), and poly(methacrylonitrile) (PMAN) is discussed in this article. In addition to homopolymers, 2D heteronuclear single-quantum coherence (HSQC), total correlation spectroscopy (TOCSY), and heteronuclear multiple-bond correlation (HMBC) study of different copolymers such as poly(methyl methacrylate-co-methyl acrylate), poly(styrene-co-methyl methacrylate), and poly(methyl methacrylate-co-methacrylonitrile) have also been reported here. This in turn helps in microstructural analysis of terpolymers such as poly(methacrylonitrile-co-styrene-co-methyl methacrylate), poly(acrylonitrile-co-methyl methacrylate-co-methyl acrylate), and poly(ethylene-co-vinyl acetate-co-carbon monoxide).

scholarly journals Tryptophan glycoconjugates in food and human urine*

1999 ◽  
Vol 343 (1) ◽  
pp. 11-19 ◽  
Author(s):  
Birgit GUTSCHE ◽  
Christoph GRUN ◽  
Dieter SCHEUTZOW ◽  
Markus HERDERICH
Keyword(s):  
Human Urine ◽  
Quantum Coherence ◽  
Nuclear Overhauser Effect ◽  
Multiple Bond ◽  
Spatial Arrangement ◽  
Coupling Constants ◽  
Tandem Ms ◽  
Multiple Quantum ◽  
Hydroxymethyl Group ◽  
Ms Analysis

Evaluating the formation of tryptophan glycoconjugates other than well-established Amadori rearrangement products, HPLC-tandem MS (MS/MS) analysis of human urine collected from several healthy individuals proved the presence of one distinct tryptophan C-glycosyl compound [Horiuchi, Yonekawa, Iwahara, Kanno, Kurihara and Fujise (1994) J. Biochem. (Tokyo) 115, 362-366]. After isolation, unambiguous identification of this novel tryptophan metabolite as 2-(α-mannopyranosyl)-L-tryptophan was achieved by tandem MS combined with NMR spectroscopy including homonuclear COSY, heteronuclear multiple-bond connectivity and 1H-detected heteronuclear multiple-quantum coherence experiments. Remarkably, a thorough evaluation of vicinal proton-proton coupling constants in different solvents and nuclear Overhauser effect experiments demonstrate the predominant axial orientation of the hydroxymethyl group of the hexopyranosyl residue. Likewise this spatial arrangement indicates that the respective α-anomeric C-mannosylhexopyranose is preferentially adopting a 1C4 conformation in acidic methanol. Whereas only one distinct tryptophan mannoconjugate could be observed in human urine, HPLC-MS/MS analysis of food samples for the first time led to the identification of numerous N1-(β-D-hexopyranosyl)-L-tryptophan, 2-(β-D-hexopyranosyl)-L-tryptophan and 1-(1,2,3,4,5-p e n t a h y d r o x y p e n t - 1 - yl) - 1, 2, 3, 4 - t e t r a h y d r o - β - c a r b o l i n e - 3 -carboxylic acid derivatives derived from the condensation of tryptophan with aldohexoses. Taking into consideration the significant differences between profiles and configurations of tryptophan glycoconjugates originating from dietary sources and human urine, C-2 mannosylation of tryptophan residues [de Beer, Vliegenthart, Loeffler and Hofsteenge (1995) Biochemistry 34, 11785-11789] represents a novel enzymic pathway in tryptophan metabolism in humans.

A norterpenoid and tripenoids from Commiphora mukul: isolation and biological activity

2017 ◽  
Vol 72 (1) ◽  
pp. 11-15 ◽  
Author(s):  
Najeeb Ur Rehman ◽  
Hidayat Hussain ◽  
Husain Yar Khan ◽  
René Csuk ◽  
Ghulam Abbas ◽  
...  
Keyword(s):  
Cancer Cells ◽  
Quantum Coherence ◽  
Nuclear Overhauser Effect ◽  
Multiple Bond ◽  
Cancer Cell Line ◽  
Inhibitory Effect ◽  
Correlation Spectroscopy ◽  
Ionization Mass ◽  
Commiphora Mukul ◽  
Substantial Decline

AbstractBio-guided fractionation of the guggul gum resin of Commiphora mukul HOOK using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay for the breast cancer cell line MDA-MB-231 led to the isolation of a new C17 norditerpene named myrrhanone C (1) along with two known polypodane-type triterpenes, namely, myrrhanone B (2) and myrrhanol B (3). The structures of the isolated compounds were elucidated by means of 1D (1H and 13C) and 2D (correlation spectroscopy, heteronuclear single-quantum coherence, heteronuclear multiple-bond correlation, and nuclear Overhauser effect spectroscopy) NMR spectroscopy as well as mass (electrospray ionization-mass spectroscopy) spectral analyses. Interestingly myrrhanone C (1) was able to induce a substantial decline in cell proliferation. It reduced the viability of cancer cells by almost 81% and 87% at concentrations of 50 and 100 μg mL−1, respectively. Myrrhanone B (2) and myrrhanol B (3) showed a concentration-dependent growth inhibitory effect on cancer cells, with the latter being slightly more cytotoxic than the former at both the concentrations tested. Furthermore, myrrhanone C (1) and myrrhanone B (2) showed good α-glucosidase and urease inhibition.

Anti-inflammatory activity of highly oxygenated terpenoids from Achillea biebersteinii Afan

2016 ◽  
Vol 71 (11-12) ◽  
pp. 429-432 ◽  
Author(s):  
Abou El-Hamd H. Mohamed ◽  
Naglaa S. Mohamed ◽  
Ahmed R. Hamed ◽  
Mohamed-Elamir F. Hegazy
Keyword(s):  
Quantum Coherence ◽  
Methylene Chloride ◽  
Multiple Bond ◽  
Correlation Spectroscopy ◽  
Inflammatory Activity ◽  
No Production ◽  
Multiple Quantum ◽  
Heteronuclear Multiple Quantum Coherence ◽  
Achillea Biebersteinii ◽  
Anti Inflammatory

Abstract In continuation of our chemical investigation on some medicinal plants of the genus Achillea, chromatographic investigation of the methylene chloride/methanol (1:1) extract of the air-dried aerial part of Achillea biebersteinii Afan. (family Asteraceae) afforded a new natural monoterpene (2), in addition to two known sesquiterpenes (3 and 4). Compound 1 was isolated as light needle crystals. Structures were established on the basis of MS and NMR spectroscopic (1H, 13C, 1H-1H correlation spectroscopy, heteronuclear multiple-quantum coherence and heteronuclear multiple-bond correlation) data and in case of compound 1 were confirmed by X-ray analysis. All isolated compounds were examined for their anti-inflammatory activity to inhibit lipopolysaccharide-induced NO production in RAW264.7 macrophage cells. Compounds 3 and 4 produced a promising anti-inflammatory effect (76% and 80% inhibition, respectively). However, compounds 1 and 2 produced moderate inhibition of NO release recording a 41% and 36% inhibition of NO production, respectively.

scholarly journals Tyrosinase Inhibition Activity of Monoterpene Glucosides From Brugmansia arborea Flowers

2019 ◽  
Vol 14 (7) ◽  
pp. 1934578X1986350
Author(s):  
Hyoung-Geun Kim ◽  
Jung-Hwan Ko ◽  
Hyun-Ji Oh ◽  
Jung-Hwa Kwon ◽  
Eun-Ji Oh ◽  
...  
Keyword(s):  
Quantum Coherence ◽  
Multiple Bond ◽  
Ethyl Acetate Fraction ◽  
2D Nmr ◽  
Correlation Spectroscopy ◽  
Tyrosinase Activity ◽  
Heteronuclear Single Quantum Coherence ◽  
Inhibition Activity ◽  
Tyrosinase Inhibition ◽  
High Inhibition

Three monoterpene glucosides were isolated from the flowers of Brugmansia arborea L. using repeated silica gel and octadecyl SiO2 column chromatography. Based on spectroscopic data including 1d-NMR (1H, 13C, and distortionless enhancement by polarization transfer (DEPT)), 2D-NMR (gradient correlation spectroscopy (gCOSY), gradient heteronuclear single quantum coherence (gHSQC), and gradient heteronuclear multiple bond coherence (gHMBC)), Infrared Spectroscophy, and Mass Spectroscophy, the glucosides were identified as citronellol O- β-D-glucopyranoside (1), jasminoside N (2), and jasminoside P (3). The EtOAc ( Brugmansia arborea Flowers ethyl acetate fraction [BAFE]) and n-BuOH ( Brugmansia arborea Flowers n-butanol fraction [BAFB]) fractions showed high inhibition of tyrosinase activity (BAFE: IC50 = 68.0 and BAFB: IC50 = 59.3 μg/mL), and all isolated monoterpenes inhibited tyrosinase activity (1: IC50 = 156.5, 2: IC50 = 198.2, and 3: IC50 = 191.0 μM).

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