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  • 1
    Electronic Resource
    Electronic Resource
    Effect of euplotin C on swimming behavior in Paramecium (2005)
    Oxford, UK : Blackwell Science Inc
    The @journal of eukaryotic microbiology 52 (2005), S. 0 
    Details
    ISSN: 1550-7408
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Biology
    Notes: The effect of euplotin C—a lipophilic toxic metabolite produced by the protist ciliate Euplotes crassus—on the swimming behavior was studied in a single-celled system represented by the ciliate Paramecium primaurelia. When in P. primaurelia internal Ca2+ concentration coupled to membrane depolarization increases, a reversal in the direction of ciliary beating and consequently in swimming direction occurs. The ciliary reversal is correlated to Ca2+ influx amount. In this study, evidence was given that continuous ciliary reversal (CCR) duration, induced by high external KCl concentrations, is longer in euplotin C-treated cells than in control cells. To test the hypothesis that euplotin C increases CCR duration by modulating a specific subtype of Ca2+ channel, selective Ca2+ channel blockers were used. Blocking L-type channels by nimodipine and verapamil, N- and Q-type channels by Ω-conotoxins, fractions GVIA and MVIIC, significantly reduced the CCR duration evoked by membrane depolarization, suggesting an involvement of these channels in ciliary reversal in Paramecium. The effect of euplotin C on CCR duration persisted when Ω-conotoxin GVIA or Ω-conotoxin MVIIC were applied, conversely, it disappeared when L-type channel blockers were used. The magnitude of the block by nimodipine and verapamil in the presence of euplotin C was comparable with that observed in the absence of euplotin C, suggesting that the Ca2+ channels modulated by euplotin C were dihydropyridine-sensible calcium channels similar to L-type channels found in mammalian cells.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1550-7408.2005.05202003_6_12.x
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  • 2
    Electronic Resource
    Electronic Resource
    Sesquiterpenoids of the Sponge Dysidea fragilis of the North-Brittany SeaPresented by F.P. as a part of a lecture at the University of Innsbruck on March 15th, 1984. (1985)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 68 (1985), S. 39-48 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The title sponge is shown to contain eight new sesquiterpenoids for which a common, unusual biogenetic origin is postulated. The compounds are shown to be: (-)-(1R*,4R*)-3-(3′-furyl)methyl-2-p-menthen-7-yl acetate ((-)-8b); two diols separated as the monoacetates (-)-(1S*,4R*)-3-(3′-furyl)methyl-l-hydroxy-2-p-menthen-7-yl acetate ((-)-13a) and the (-)-(1R*,4R*)-epimer (-)-13b, the two C(4)-epimeric 4-ethoxy-3-(1′(7′),2′-p-menthadien-3′-yl)methyl-2-buten-4-olides ((+)-14a and (-)-14b), (-)-3-(3′-furyl)methyl-7-nor-2-p-menthen-l-one ((-)-11), (-)-(3Z)-1-(3′-furyl)-4,8-dimethylnona-3, 7-dien-2-yl acetate ((-)-17), and (+)-3-(5′,7′-seco-2′(10′)-pinen-7′-yl)methylfuran ((+)-15).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19850680105
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  • 3
    Electronic Resource
    Electronic Resource
    New Furano-sesquiterpenoids from Mediterranean Sponges (1985)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 68 (1985), S. 1276-1282 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A mixture of sponges of the East Pyrenean Mediterranean is shown to contain the known sponge products longifolin (1), avarol ((+)-3), and avarone (4) and the terrestrial-plant product sesquirosefuran (2), besides to the new furano-sesquiterpenoids tavacfuran (= 3-methyl-2-[(3′Z)-3′-methyl-4″-methyl-2″-furyl-3′-butenyl]furan; (5) and tavacpallescensin (= 5,10-dihydro-6,9-dimethyl-4H-benzo[5,6]cyclohepta[1,2-b]furan; 6) and the new furano-butenolide sesquiterpenoids tavacbutenolide-1 (= (±-4-ethoxy-2-methyl-4-)[(2′E)-2′-methyl-4′-(3″-methyl-2″-furyl)-2′-butenyl]-2-buten-4-olide; (±)-7) and tavacbutenolide-2 (= (±)-4-ethoxy-3-methyl-4-[2′E)-3′-methyl-4′-(4″-methyl-2″-furyl)-2′-butenyl]-2-buten-4-olide; (±)-8). Structural assignments are based on NMR data and on the synthesis of the (E)-isomer of 5. The sponge Dysidea tupha of the same area is also shown to contain the two sesquiterpenoids ent-furodysinin ((-)-14), which is enantiomeric to a product of a Dysidea sp. of Australian waters, and tuphabutenolide ((+)-15).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19850680523
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  • 4
    Electronic Resource
    Electronic Resource
    Verapliquinones: Novel Diprenylquinones from an Aplidium sp. (Ascidiacea) of Ile-Verte Waters, Brittany (1987)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 70 (1987), S. 621-626 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An Aplidium sp. (Ascidiacea), collected in French Atlantic waters near the Ile Verte, is shown to contain verapliquinone B (2) and verapliquinone D (6) as the first examples of linear diprenylquinones of the neryl type, besides their respective isomers 1 and 5 of the geranyl type.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19870700316
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  • 5
    Electronic Resource
    Electronic Resource
    Cacospongione A, cacospongienone A, and cacospongienone B, new C21 difuran terpenoids from the marine sponge Cacospongiascalaris SCHMIDT of the Côte d' Azur (1986)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 69 (1986), S. 726-733 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The sponge Cacospongia scalaris (family Thorectidae), collected at the Cap de Nice (Cǒte d'Azur), is shown to contain a series of truncated, linear C21 difuran terpenoids comprising the known sponge products furospongin-1 ((+)-1), furospongin-2 (2), and dihydrofurospongin-2 ((-)-(E)-3), besides the new products cacospongione A ((-)-4), cacospongienone A ((-)-(Z)-6), and cacospongienone B ((-)-(E)-6), whose absolute configurations have been assigned by chemical correlations with (+)-1. Possibly, one of the two cacospongienones is an artifact, as these two terpenoids interconvert on standing. This is the first finding of linear C21 difuran terpenoids, which are typical of the Spongiidae, in a member of the family Thorectidae.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19860690325
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  • 6
    Electronic Resource
    Electronic Resource
    Oxidative Breaking of Long-Chain Acetylenic Enol Ethers of Glycerol of the Marine Sponges Raspailia pumila and of Model Compounds with Aerial Oxygen (1987)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 70 (1987), S. 1400-1411 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The raspailynes (novel long-chain enol ethers of glycerol having the enol ethers double bond conjugated in sequence, to an acetylenic and an olefinic bond, isolated from the North-East-Atlantic sponges Raspailia pumila and R. ramosa) are stable under normal hydrolytic conditions for enol ethers. In contrast, when their solutions are evaporated, these lipids such as raspailyne Bl (=(-))-3-[(1Z,5Z)-(tetradeca-1,5-dien-3-ynyl)oxy]-1,2-propanediol;(--2) rapidly react with aerial O2 under normal laboratory-daylight conditions, with rupture of the C=C enol ether bond to give 1-O-formylglycerol (3) and an aldehyde (such as tridec-4-en-2ynal(4) from (-)-2). This reaction must be caused by triplet O2, since thermally generated singlet O2 has no effect on (-)-2 in solution. That the mere presence of an enol-ether moiety conjugated to an acetylenic group is responsible for such a behaviour is demonstrated with the model compounds 1-methoxypentadec-1-en-3-yn-5-ol (6a) and its 5-O-acetyl or 5-O-tetra-hydropyranyl derivatives 6b and 6c, respectively. Resistance to both hydroytic conditions and singlet O2 of these compounds is thought to arise from electron depletion at the enol-ether C(beta;) atom by the acetylenic group. Plausible reaction pathways for enol-ether bond rupture in these compounds by aerial O2 are outlined.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19870700521
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  • 7
    Electronic Resource
    Electronic Resource
    Sphinxolide, a 26-Membered Antitumoral Macrolide Isolated from an Unidentified Pacific Nudibranch (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 237-246 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: It is shown that an unidentified nudibranch of Hawaiian waters contains a 26-membered macrolide, sphinxolide ((-)-1) with potent activity against the KB cell line. The structure of sphinxolide, a 2:1 mixture of (E/Z)-isomers at the formamide moiety, is established to be (-)-1 on the basis of extensive NMR and FAB-MS analysis, in combination with data for the products of mono- (→(-)-2) and diacetylation (→(+)-3).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720207
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  • 8
    Electronic Resource
    Electronic Resource
    Rogiolol Acetate: A Novel β-Chamigrene-Type Sesquiterpene Isolated from a Marine SpongeWe use the chamigrene numbering for the structural formulae and spectroscopic data; IUPAC nomenclature and numbering are used for retrieval purposes (1990)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 73 (1990), S. 1612-1620 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The marine sponge Spongia zimocca SCHMIDT, 1862, collected in front of the torrent II Rogiolo, south of Livorno, contains the sesquiterpene rogiolol acetate (= (+)-(2R,3S,6R,8R,9R)-2,8-dibromo-9-chloro-1,1,9-trimethyl-5-methylidenespiro[5.5]undec-3-yl acetate; (+)-3a), which represents the first chamigrane isolated from a sponge. Although compounds of this class are common in red seaweeds of the genus Laurencia, and our sponge actually contains 9-bromochamigrene and a variety of other metabolites of nearby growing Laurencia sp., (+)-3a is unique to our sponge.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19900730606
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  • 9
    Electronic Resource
    Electronic Resource
    Conformational Analysis of Marine Polyhalogenated β-Chamigrenes Through Temperature-Dependent NMR SpectraPresented in part by G.G. at both CISCI 90, S. Benedetto del Tronto, 30 September-5 October 1990, and the Congresso Nazionale di Risonanze Magnetiche, Pisa, 22-24 October 1990. (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 774-786 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Temperature-dependent 1H- and 13C-NMR spectra reveal that polyhalogenated marine β-chamigrenes or synthetic derivatives thereof which are trans-diequatorially, substituted at C(8) and C(9), such as rogiolol ((-)-2), obtusol ((+)-3), and their acetates (+)-1 and (-)-4, undergo slow ring-A chair-chair inversion. Conformational equilibria and kinetics are investigated with the aid of synthetic model compounds and molecular-mechanics calculations. Thus, steric repulsions between Brax-C(2) and Heq-C(7) are seen to disfavour thermodynamically conformers 1b, 2b, 3b, and 4b, which can only be detected through cross-saturation transfer, while additional steric repulsions between Meax-C(1) and OHax-C(3) make conformer 8b of obtusol epimer so scarcely populated that it can not be detected. In agreement, with (+)-9 and (+)-10, which have a trigonal C(2), two conformers can be directly observed by NMR. The kinetic barriers, which are seen to arise mainly from steric repulsions between Hax-C(14) and the axial H or halogen atoms at C(8) and C(10), are calculated and discussed with respect to well documented exocycliemethylidene-substituted cyclohexane(ene) systems. This helps to rationalize why in rogiolol acetate ((+)-1) ring B is unusually inert towards Zn/Et2O/AcOH which causes bromohydrine-group elimination from ring A.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740411
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  • 10
    Electronic Resource
    Electronic Resource
    Conformational Studies of Marine Polyhalogenated α-Chamigrenes Using Temperature-dependent NMR spectra inverted-chair and twist-boat cyclohexane moieties in the presence of an axial halogen atom at C(8)We use the chamigrene numbering for the structural formulae and spectroscopic data (see(+)-1); for IUPAC nomenclature and numbering for retrieval purposes, see Exper. Part. (1992)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 75 (1992), S. 2026-2040 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: α-Chamigren-3-one (+)-8 bearing an axial CI-atom at C(8) exists as a largely dominant conformer with Me - C(5) at the envelope-shaped enone ring pointing away from CIax-C(8) at the cyclohexane ring (= B) in the ‘normal’ chair conformation, as shown by 1H-NMR. In contrast, the α-chamigren-3-ols (+)-9 and (+)-10, obtained from hydride reduction of (+)-8, show a temperature-dependent equilibrium of conformers where the major conformers have ring B in the inverted-chair (and twist-boat for (+)-9) conformation to avoid repulsions between Me-C(5) and CIax-C(8) (Scheme 1). This is in agreement with the conformation of the epoxidation product (+)-12 of (+)-9 where Me-C(5) is pushed away from CIax-C(8) in a ring-B chair similar to that of (+)-8 (Scheme 2). Introduction of a pseudoequatorial Br-atom at C(2) of (+)-8, as in enone (+)-15 (Scheme 3), does not affect the conformation; but a pseudoaxial Br—C(2) experiences repulsive interactions with Heq-C(7), as shown by the 1H-NMR data of the isomeric enone (+)-16 where the ‘normal’-chair conformer Cβ-16 is in an equilibrium with the inverted chair conformer ICβ-16 (Scheme 3). These results and the accompanying paper allow a unifying view on the conformational behavior of marine polyhalogenated α-chamigrenes. This view is supported by the acid-induced isomerization of α-chamigrene (+)-9 (inverted chair) to β-chamigrene (+)-17 (‘normal’ chair; Scheme 4), the driving force being the lesser space requirement of CH2=C(5) than of Me-C(5). This explains why β-chamigrenes are so common in nature.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19920750627
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