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  • 1
    Electronic Resource
    Electronic Resource
    Lagotoside: A New Phenylpropanoid Glycoside from Lagotis stolonifera (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1273-1277 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: From the aerial parts of Lagotis stolonifera (Scrophulariaccae), a new phenylpropanoid glycoside, lagotoside (8), and the three known glycosides ehrenoside (5), verbascoside (= acteoside; 6), and plantamajoside (7) were isolated, together with the four known iridoid glucosides aucubin (1), catalpol(2), globularin (4), and lythantosalin (3). The structure of the new compound 8 was elucidated on the basis of chemical and spectral data as 2-(3-hy-droxy-4-methoxyphenyl)ethyl O-[α-L-arabinopyranosyl-(1 → 2)]-O-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-feruloyl-β-D-glucopyranoside.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740615
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  • 2
    Electronic Resource
    Electronic Resource
    Anatoliosides: Five Novel Acyclic Monoterpene Glylcosides from Viburnum orientaleThis paper was presented in two parts at the poster sessions of the' International Research Congress on Natural Products, 32nd Annual Meeting of the American Society of Pharmacognosy', Chicago, USA, July 21-26, 1991, and of the ‘39th Annual Congress on Medicinal Plant Research’, Saarbrücken Germany, September 3-7, 1991. (1993)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 76 (1993), S. 416-424 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Five new acyclic monoterpene glycosides 1-5 were isolated from the leaves of Viburnum orientale (Caprifoliaceae). Anatolioside (1) is a monoterpene diglycoside and its structure was elucidated as linalo-6-yl 2′-O-(α-L-rhamnopyranosyl)β-D-glucopyranoside (arbitrary numbering of linalool moiety). Compounds 2-5 are all derivatives of 1, containing additional monoterpene and sugar units, connected by ester and glycoside bonds. Their structures were established as linalo-6-yl O-[(2E,6R)-6-hydroxy-2, 6-dimethylocta-2,7-dienoyl]-(1‴ → 4″)-O-α-L-rhamnopyranosyl-(1″‴ → 2″″)-β-D-glucopyranoside ( = anatolioside A; 2), linalo-6-yl O-β-D-glucopyranosyl-(1‴ → 6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴ → 4″)-O-α-L-rhamnopyranosyl-(1″ → 2′)-β-D-glucopyranoside ( = anatolioside B; 3), linalo-6-yl O-β-Dribo-hexopyranos-3-ulosyl-(1′‴ → 6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴ → 4″)-O-α-L-rhamnopyranosyl-(1″ → 2′)-β-D-glucopyranoside ( = anatolioside C; 4) and linalo-6-yl O-[(2E, 6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1″‴ → 2″″)-O-β-D-glucopyranosly-(1″″ → 6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴ → 4″)-O-α-L-rhamnopyranosyl(1″ → 2′)-β-D-glucopyranoside ( = anatolioside D; 5). The structure determinations were based on spectroscopic and chemical methods (acid and alkaline hydrolysis, acetylation and methylation).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19930760125
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  • 3
    Electronic Resource
    Electronic Resource
    Determination of the Absolute Configuration of a Series of Halogenated Furanones from the marine alga delisea pulchra (1995)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 78 (1995), S. 758-764 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The absolute configuration of a series of naturally occurring and semi-synthetic halogenated furanones is proposed on the basis of chemical interconversions and X-ray and CD analyses. The CD analyses clearly reveal that the presence of the allylic O-atom has a strong influence in determining the sign and intensity of the low energy π→π* transition.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19950780320
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  • 4
    Electronic Resource
    Electronic Resource
    New Dolabellane Derivatives from the Brown Alga Dictyota pardalis (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1801-1807 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reinvestigation of the brown alga Dictyota pardalis f. pseudohamata CRIBB led to the crystallization of 1 and to the isolation of the two new dolabellane derivatives 2 and 3. X-Ray analysis of 1 and 2, together with detailed 1D-and 2D-NMR studies on 2 and 3, allowed their structures to be elucidated as (1R*,3S*,7S*,11R*,4Z)-dolabella-4,8(17), 12(18)-triene-3,7-diol (1), (1R*,3S*,4S*,7S*,8S*,11R*,14R*,12E)-3,4:7,8-diepoxydolabe11-12-ene-14, 18-diol (2), and (1R*,3S*,4S*,7S*,8S*,11R*,14R*)-3,4:7,8-diepoxy-l,4,8,12,12-pentamethylbicyclo[9. 3. 0]tetra-decan-14-ol(3).
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740822
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  • 5
    Electronic Resource
    Electronic Resource
    New Monoterpene-Substituted Dihydrochalcones from Piper aduncum (1993)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 76 (1993), S. 1481-1488 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Five New unusual monoterpene-substituted dihydrochalcones, the adunctins A-E (1″S)-1-{2′-hydroxy-4′-methoxy-6′-[4″-methyl-1″-(1‴-methylethyl)cyclohex-3″ -en-1″ -yloxy]phenyl}-3-phenylpropan-1-one (1), (5aR*,8R*,9aR*)-3-phenyl-1-[5′,8′,9′,9′a-tetrahydro-3′-hydroxy-1′-methoxy-8′-(1″-methylethyl)-5′-a-methyldibenzo-[b,d]furan-4′-yl]propan-1-one (2), (2′R*,4″S*)-1-{6′-hydroxy-4′-methoxy-4″-(1‴-methylethyl)spiro[benzo[b]-furan-2′(3′H),1″ -cyclohex-2″ -en]-7′-yl}-3-phenylpropan-1-one (3), (2′R*,4″R*)-1-{6′-hydroxy-4′-methylethyl-4″-(1‴-methylethyl)spiro[benzo[b]furan-2′(3′H),1″-cyclohex-2″-en]-7′-yl}-3-phenypropan-1-one (4), and (5′aR*,6′S*, 9′R*,9′aS*)-1-[5′a,6′,7′,8′,9′a-hexahydro-3′,6′-methoxy-6′-methyl-9′-(1″-methylethyl)dibenzo[b,d]-furan-4′-yl]-3-phenylpropan-1-one (5) were isolated from the leaves of Piper aduncum (Piperaceae) by preparative liquid chromatography. In addition, (-)-methyllindaretin (6), trans-phytol, and α-tocopherol ( = vitamin E) were also isolated and identified. The structures were elucidated by spectroscopic methods, including 1D- and 2D-NMR spectroscopy as well as single-crystal X-ray diffraction analysis. The antibacterial and cytotoxic potentials of the isolates were also investigated.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19930760409
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  • 6
    Electronic Resource
    Electronic Resource
    Anatolioside E: A New Acyclic Monoterpene Glycoside from Viburnum orientaleThis paper was presented at the poster session of the ‘40th Annual Congress on Medicinal Plant Research’, Trieste, Italy, September 1-5, 1992; see [1].Dedicated to Prof. Dr. Mekin Tanker on the occasion of his 40th academic year. (1993)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 76 (1993), S. 2563-2569 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new open-chain monoterpene glycoside, anatolioside E (1), was isolated from the leaves of Viburnum orientale in addition to three known acyclic monoterpene glycosides, betulalbusides A (2) and B (3), and 2(E)-2,6-dimethyl-2,7-octadien-1,6-diol-6-O-β-D-glucopyranoside(4). The structure of anatolioside E (1) was elucidated on the basis of chemical and spectral data as 6-O-[β-D-glucopyransoyl-(1‴‴ → 6‴″)-2-(E), 6(R), 2,6-dimethyl-6-hydroxy-2,7-octadienoyl-(1‴″ → 2″″)-β-D-glucopyranosyl-(1″″ → 6‴)-2-(E), 6(R), 2,6-dimethyl-6-hydroxy-2,7-octadienoyl-(1‴ → 4″)-α-L-rhamnopyranosyl-(1″″ → 2′)-β-D-glucopyranosyl]linalool.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19930760716
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  • 7
    Electronic Resource
    Electronic Resource
    A New Tyrosine Kinase Inhibitor from a Marine Isolate of Ulocladium botrytis and New Metabolites from the Marine Fungi Asteromyces cruciatus and Varicosporina ramulosa (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 2949-2955 
    Details
    ISSN: 1434-193X
    Keywords: Marine fungi ; Tyrosine kinase ; Natural products ; Macrodiolides ; Polyketides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The sponge-derived fungi Ulocladium botrytis and Asteromyces cruciatus, and the algal-derived fungus Varicosporina ramulosa, were isolated and extracts from cultures investigated for their metabolite production. Investigations of the extract of the culture of U. botrytis guided by bioassay yielded the new tyrosine kinase (p56lck) inhibitor ulocladol (1) together with 1-hydroxy-6-methyl-8-(hydroxymethyl)xanthone (3), which showed antifungal activity. The extract of the culture medium of A. cruciatus yielded the new metabolite (+)-2,4-dimethyl-4,5-dihydrofuran-3-carbaldehyde (4) together with the known compounds (3S,5R)-dimethyldihydrofuran-2-one (5) and tri-O-acetyl glycerol. From V. ramulosa the five macrodiolides grahamimycin A1 (6), colletoketol (7), (6R,11R,12R,14R)-colletodiol (8), 9,10-dihydro-(6R,11S,12S,14R)-colletodiol (9) and 9,10-dihydro-(6R,11R,12R,14R)-colletodiol (10) together with ergosterol were obtained, 9 and 10 being new fungal metabolites.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 8
    Electronic Resource
    Electronic Resource
    Concerted application of a shift reagent and 2D NOESY to the structure determination of new natural products from the tropical brown alga Dictyopteris delicatula (1995)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 33 (1995), S. 178-183 
    Details
    ISSN: 0749-1581
    Keywords: 1H NMR ; 13C NMR ; NOESY ; INADEQUATE ; lanthanide shift reagents ; brown algae ; sesquiterpenes ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: From the marine brown alga Dictyopteris delicatula Lamaouroux, two new (1, 3) and two previously reported sesquiterpenes (2, 4) were isolated and characterized. Compound 1 was identified as 4β,5α-dihydroxycubenol and 2 was found to be a non-racemic mixture of (±)-torreyol. Compound 3 was characterized as cubenol-3-one and 4 was identified as cubenol. For the assignment of the complete relative stereochemistry of compounds 1 and 2, it was necessary to employ extensive 2D NMR methodologies in combination with the lanthanide shift reagent europium(III) tris(1,1,1,2,2,3,3)-heptafluoro-7,7-dimethyl-d6-octane-4,6-dione-d3 [Eu(fod)3]. Anomalous proton shielding effects which occurred on addition of Eu(fod)3 to compound 1 suggested that classical lanthanide-induced shift (LIS) analysis for predicting proton chemical shifts was not applicable. Application of 2D NOESY measurements to NMR samples of 1 and 2 containing Eu(fod)3 clearly demonstrated an alternative to classical methods for interpreting lanthanide-induced shifts. The enhanced value of shift reagnents of this type as an aid to structure determination and as for assignment purposes is demonstrated.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1260330305
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