Deoxyspongiaquinones: New Sesquiterpene Quinones and Hydroquinones From a Southern Australian Marine Sponge Euryspongia sp.
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Abstract:
Chemical investigation of a marine sponge, Euryspongia sp., collected from the Great Australian Bight, Australia, resulted in the isolation of two new sesquiterpene quinones , deoxyspongiaquinone (4) and (E)-chlorodeoxyspongiaquinone (5), as well as two sesquiterpene hydroquinones, deoxyspongiaquinol (6) and (E)-chlorodeoxyspongiaquinol (7). The structures for (4)-(7) were determined by detailed spectroscopic analysis, as well as chemical interconversion and degradation.Keywords:
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Three new tetracyclic sesquiterpene hemiketals possessing the very rare allo-cedrane carbon skeleton, debenzoyl-7-deoxo-1α,7α-dihydroxytashironin, debenzoyl-7-deoxo-7α-hydroxytashironin, and debenzoyl-7-deoxo-7α-hydroxy-3-oxotashironin (1−3), were isolated from the fruits of Illicium floridanum ELLIS (American Star Anise, Star bush). Their structures were elucidated by mass and NMR spectroscopic analyses. The molecular structure of 1, including absolute stereochemistry, was determined by single-crystal X-ray diffraction of its monohydrate. Only one compound of this type, tashironin, has previously been isolated from Illicium tashiroi. Furthermore, a new sesquiterpene lactone of the seco-prezizaane type, 3,4-anhydro-13,14-dihydroxyfloridanolide (4), and the known anislactone B (5) were isolated. The occurrence of further allo-cedrane sesquiterpenes in another Illicium species confirms the hypothesis of previous authors that this type of compound is a biogenetic precursor of the typical seco-prezizaane sesquiterpene lactones found in this genus. Moreover, regarding their co-occurrence with anislactone B as reported here, they may also be considered precursors for the anislactone skeletal type.
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A new sesquiterpene isothiocyanate, ( – )-9-isothiocyanatopupukeanane (4), has been isolated along with the known sesquiterpene metabolites ( – )-9-isocyanopupukeanane (1), ( – )-2-thiocyanatoneopupukeanane (2) and ( – )-epipolasin-A (3) from the sponge Axinyssa sp. nov. Metabolites (1), (2) and (4) showed modest in vitro antimalarial activity.
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From the dichloromethane solubles of the tropical marine sponge Dactylospongia elegans, a new aromatic substituted sesquiterpene, pelorol (1), and the known sesquiterpene, ilimaquinone (2), were isolated. The structures of 1 and 2 were deduced from their spectroscopic data. The biological activities of compounds 1 and 2 were assessed in a variety of bioassays, and both compounds were found to have weak antitrypanosomal and antiplasmodial effects.
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Four new sesquiterpenes, lamellodysidines A and B, O,O-dimethyllingshuiolide A, and 11-epi-O,O-dimethyllingshuiolide A (1–4), were obtained from the marine sponge, Lamellodysidea herbacea, collected in Indonesia. Their planar structures were elucidated by analysis of spectroscopic data. The absolute configurations of the new compounds were determined by the calculated ECD spectra. Compound 1 has a unique carbon framework, and 2 is a new nitrogenous sesquiterpene.
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Two new sesquiterpene hydroquinones, polyfibrospongols A (1) and B (2), were isolated from the Taiwanese marine sponge Polyfibrospongia australis Lendenfeld (Spongiidae) in addition to the known metabolites, dictyoceratin A (3), ilimaquinone (4), and 5-epi-ilimaquinone (9). The structures of these compounds have been determined mainly on the basis of spectral and chemical methods. Biological testing revealed that compounds 1 and 2 exhibited significant cytotoxicity against human KB-16, A-549, and murine P-388 tumor cell lines.
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Six new meroterpenoids (1-6), along with arenarol (7), a known rearranged drimane sesquiterpene hydroquinone, were isolated from a Dysidea sp. sponge collected from the Federated States of Micronesia. On the basis of the results of combined spectroscopic analysis, compound 1 was determined to be the cyclic ether derivative of 7, whereas 2 and 3 were assigned as the corresponding sesquiterpene quinones containing taurine-derived substituents. Compounds 4-6 possess a novel tetracyclic skeleton formed by a direct linkage between the quinone and sesquiterpene moieties. The configurations of these new compounds were assigned on the basis of combined NOESY and ECD analysis. These compounds exhibited cytotoxic and antimicrobial activities and weak inhibition against Na(+)/K(+)-ATPase.
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Abstract Two isonitrile sesquiterpenes 2 and 3 have been isolated from the toxic dichloromethane extract of the marine sponge Acanthella acuta . Compound 2 was found to be identical with axisonitrile‐3. compound 3, 1‐isocyanoaromadendrane, is a novel sesquiterpene whose structure has been determined on the basis of its spectral properties and by chemical correlation with palustrol.
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