Shaagrockol B and C; two hexaprenylhydroquinone disulfates from the red sea sponge toxiclona toxius

Isaacs, S.; Kashman, Yoel

doi:10.1016/0040-4039(92)88184-7

Cited by 25 publications

(23 citation statements)

References 9 publications

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“…For 4 , protonation of the 6,7-epoxide would initiate the second cyclization event involving the 10,11-olefin ( Figure 6 (Ai)), while hydrolysis of the epoxide would lead to 3 ( Figure 6 (Aii)). The first cyclization event of shaagrockol C ( 22 ) would also produce a bicyclic system, though deprotonation would occur prior to any rearrangement, yielding a tetra-substituted alkene ( Figure 6 B) [ 28 ]. The second cyclization would be similar to that of 4.…”

Section: A Proposed Biosynthetic Route For Sponge Hydroquinone Mermentioning

confidence: 99%

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Biogenetic Relationships of Bioactive Sponge Merotriterpenoids

Smith

2017

Marine Drugs

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Hydroquinone meroterpenoids, especially those derived from marine sponges, display a wide range of biological activities. However, use of these compounds is limited by their inaccessibility; there is no sustainable supply of these compounds. Furthermore, our knowledge of their metabolic origin remains completely unstudied. In this review, an in depth structural analysis of sponge merotriterpenoids, including the adociasulfate family of kinesin motor protein inhibitors, provides insight into their biosynthesis. Several key structural features provide clues to the relationships between compounds. All adociasulfates appear to be derived from only four different hydroquinone hexaprenyl diphosphate precursors, each varying in the number and position of epoxidations. Proton-initiated cyclization of these precursors can lead to all carbon skeletons observed amongst sponge merotriterpenoids. Consideration of the enzymes involved in the proposed biosynthetic route suggests a bacterial source, and a hypothetical gene cluster was constructed that may facilitate discovery of the authentic pathway from the sponge metagenome. A similar rationale can be extended to other sponge meroterpenoids, for which no biosynthetic pathways have yet been identified.

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Section: A Proposed Biosynthetic Route For Sponge Hydroquinone Mermentioning

confidence: 99%

“…Finally, the C7 hydroxyl would initiate a final cyclization with the 2,3-alkene, forming a 7-membered terminal heterocycle. Shaagrockol B, isolated together with 22 , is the oxidation product of 22 about the 22,23-alkene and is likely not enzymatic in origin [ 28 ].…”

Section: A Proposed Biosynthetic Route For Sponge Hydroquinone Mermentioning

confidence: 99%

Biogenetic Relationships of Bioactive Sponge Merotriterpenoids

Smith

2017

Marine Drugs

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“…The sulfated compounds toxiusol ( 272 ), shaagrockol B ( 273 ), shaagrockol C ( 274 ), toxicol A ( 275 ), toxicol B ( 276 ), the p-hydroquinone derivative of compound 275 , and toxicol C ( 277 ), isolated from Toxiclona toxius [185,186], are of interest not only because of their structures but also because of their biological properties, which includes an important activity against human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT). The hydrolysis of compounds 272 and 274 yielded the corresponding hydroquinones designated as compounds 278 and 279 , and further oxidation of compound 276 afforded the corresponding p-quinone derivative.…”

Section: Meroterpenes From Spongesmentioning

confidence: 99%

Meroterpenes from Marine Invertebrates: Structures, Occurrence, and Ecological Implications

et al. 2013

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Meroterpenes are widely distributed among marine organisms; they are particularly abundant within brown algae, but other important sources include microorganisms and invertebrates. In the present review the structures and bioactivities of meroterpenes from marine invertebrates, mainly sponges and tunicates, are summarized. More than 300 molecules, often complex and with unique skeletons originating from intra- and inter-molecular cyclizations, and/or rearrangements, are illustrated. The reported syntheses are mentioned. The issue of a potential microbial link to their biosynthesis is also shortly outlined.

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“…Noteworthy, as already mentioned by Bowden and Coll,6 is the para dialkylation of the hydroquinone found in the soft corals compared to the meta dialkylation found in brown alga metabolites (e.g., Cystoseira sp. 3 ).…”

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confidence: 91%

“…These must include one carbon bearing two oxygens (C-4) (δ c 102.3 ppm), one of the five methyls (Me-19) (which because of its low-field proton resonance (δ H 1.58s), and the fact that it is not a vinyl methyl must be attached to an oxygenated carbon atom (C-7) (δ C 84.5s)), and an ethylene group (C-5 and - 6) [(δ C 23.5 t and 26.3 t, and δ H 1.44 m (1H) and 2.11 m (3H)]. Since sindurol (2) contains 10 degrees of unsaturation, of which eight were accounted for by partial structures A and B, vide supra, the remaining connecting portion has to be bicyclic.…”

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confidence: 99%

Sindurol and Nephthoside: New Tetraprenyltoluquinols from the Soft Coral Sinularia dura and Nephthea sp.

et al. 1996

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Four new tetraprenyltoluquinols (2−5) have been isolated from the Indo-Pacific soft corals Sinularia dura and Nephthea sp. Sindurol (2), isolated from the Sinularia, is a 1,3,5-trialkylated 2,8-dioxabicyclo[3.2.1]octane, and nephthoside (4), obtained from the Nephthea, is a new substituted hydroquinone d-arabinose glycoside. Compounds 3 and 5 are closely related to nephthoside (4). The structure determination of all new compounds was based mainly on 1D- and 2D-NMR spectroscopy and mass spectrometry, as well as some chemical transformations.

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Shaagrockol B and C; two hexaprenylhydroquinone disulfates from the red sea sponge toxiclona toxius

Cited by 25 publications

References 9 publications

Biogenetic Relationships of Bioactive Sponge Merotriterpenoids

Biogenetic Relationships of Bioactive Sponge Merotriterpenoids

Meroterpenes from Marine Invertebrates: Structures, Occurrence, and Ecological Implications

Sindurol and Nephthoside: New Tetraprenyltoluquinols from the Soft Coral Sinularia dura and Nephthea sp.

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