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Mar. Drugs, Volume 10, Issue 2 (February 2012), Pages 258-520

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Research

Jump to: Review

Open AccessArticle Recruitment of Glycosyl Hydrolase Proteins in a Cone Snail Venomous Arsenal: Further Insights into Biomolecular Features of Conus Venoms
Mar. Drugs 2012, 10(2), 258-280; doi:10.3390/md10020258
Received: 25 November 2011 / Revised: 13 January 2012 / Accepted: 14 January 2012 / Published: 31 January 2012
Cited by 20 | PDF Full-text (2787 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Cone snail venoms are considered an untapped reservoir of extremely diverse peptides, named conopeptides, displaying a wide array of pharmacological activities. We report here for the first time, the presence of high molecular weight compounds that participate in the envenomation cocktail used [...] Read more.
Cone snail venoms are considered an untapped reservoir of extremely diverse peptides, named conopeptides, displaying a wide array of pharmacological activities. We report here for the first time, the presence of high molecular weight compounds that participate in the envenomation cocktail used by these marine snails. Using a combination of proteomic and transcriptomic approaches, we identified glycosyl hydrolase proteins, of the hyaluronidase type (Hyal), from the dissected and injectable venoms (“injectable venom” stands for the venom variety obtained by milking of the snails. This is in contrast to the “dissected venom”, which was obtained from dissected snails by extraction of the venom glands) of a fish-hunting cone snail, Conus consors (Pionoconus clade). The major Hyal isoform, Conohyal-Cn1, is expressed as a mixture of numerous glycosylated proteins in the 50 kDa molecular mass range, as observed in 2D gel and mass spectrometry analyses. Further proteomic analysis and venom duct mRNA sequencing allowed full sequence determination. Additionally, unambiguous segment location of at least three glycosylation sites could be determined, with glycans corresponding to multiple hexose (Hex) and N-acetylhexosamine (HexNAc) moieties. With respect to other known Hyals, Conohyal-Cn1 clearly belongs to the hydrolase-type of Hyals, with strictly conserved consensus catalytic donor and positioning residues. Potent biological activity of the native Conohyals could be confirmed in degrading hyaluronic acid. A similar Hyal sequence was also found in the venom duct transcriptome of C. adamsonii (Textilia clade), implying a possible widespread recruitment of this enzyme family in fish-hunting cone snail venoms. These results provide the first detailed Hyal sequence characterized from a cone snail venom, and to a larger extent in the Mollusca phylum, thus extending our knowledge on this protein family and its evolutionary selection in marine snail venoms. Full article
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Open AccessArticle New Cytotoxic Cembranolides from the Soft Coral Lobophytum michaelae
Mar. Drugs 2012, 10(2), 306-318; doi:10.3390/md10020306
Received: 23 December 2011 / Revised: 20 January 2012 / Accepted: 20 January 2012 / Published: 31 January 2012
Cited by 13 | PDF Full-text (874 KB) | HTML Full-text | XML Full-text
Abstract
Six new cembranolides, michaolides L–Q (16), and a known cembranolide, lobomichaolide (7) were isolated from the CH2Cl2 extract of the soft coral Lobophytum michaelae. Their structures were established by extensive spectral analysis. [...] Read more.
Six new cembranolides, michaolides L–Q (16), and a known cembranolide, lobomichaolide (7) were isolated from the CH2Cl2 extract of the soft coral Lobophytum michaelae. Their structures were established by extensive spectral analysis. The anti-HCMV (human cytomegalovirus) activity of 17 and their cytotoxicity against selected cell lines were evaluated. Full article
Open AccessArticle Five New Amicoumacins Isolated from a Marine-Derived Bacterium Bacillus subtilis
Mar. Drugs 2012, 10(2), 319-328; doi:10.3390/md10020319
Received: 20 December 2011 / Revised: 29 January 2012 / Accepted: 30 January 2012 / Published: 3 February 2012
Cited by 19 | PDF Full-text (263 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Four novel amicoumacins, namely lipoamicoumacins A–D (14), and one new bacilosarcin analog (5) were isolated from culture broth of a marine-derived bacterium Bacillus subtilis, together with six known amicoumacins. Their structures were elucidated on the [...] Read more.
Four novel amicoumacins, namely lipoamicoumacins A–D (14), and one new bacilosarcin analog (5) were isolated from culture broth of a marine-derived bacterium Bacillus subtilis, together with six known amicoumacins. Their structures were elucidated on the basis of extensive spectroscopic (2D NNR, IR, CD and MS) analysis and in comparison with data in literature. Full article
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Open AccessArticle Toxicity of Cultured Bullseye Puffer Fish Sphoeroides annulatus
Mar. Drugs 2012, 10(2), 329-339; doi:10.3390/md10020329
Received: 19 December 2011 / Revised: 14 January 2012 / Accepted: 18 January 2012 / Published: 3 February 2012
Cited by 4 | PDF Full-text (1033 KB) | HTML Full-text | XML Full-text
Abstract
The toxin content in various life cycle stages of tank-cultivated bullseye puffer (Sphoeroides annulatus) were analyzed by mouse bioassay and ESI-MS spectrometry analysis. The presence of toxin content was determined in extracts of sperm, eggs, embryo, larvae, post-larvae, juvenile, pre-adult, and adult fish, as well as in food items used during the cultivation of the species. Our findings show that only the muscle of juveniles, the viscera of pre-adults, and muscle, liver, and gonad of adult specimens were slightly toxic ( < 1 mouse unit). Thus, cultivated S. annulatus, as occurs with other cultivated puffer fish species, does not represent a food safety risk to consumers. This is the first report of toxin analysis covering the complete life stages of a puffer fish under controlled conditions. Full article
(This article belongs to the Special Issue Tetrodotoxin)
Open AccessArticle Four Eremophilane Sesquiterpenes from the Mangrove Endophytic Fungus Xylaria sp. BL321
Mar. Drugs 2012, 10(2), 340-348; doi:10.3390/md10020340
Received: 2 December 2011 / Revised: 17 January 2012 / Accepted: 17 January 2012 / Published: 6 February 2012
Cited by 16 | PDF Full-text (281 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Three new eremophilane sesquiterpenes (13) were isolated from the mangrove endophytic fungus Xylaria sp. BL321 together with 07H239-A (4), a known analogue of the new compounds. The structures of these compounds were elucidated by analysis of [...] Read more.
Three new eremophilane sesquiterpenes (13) were isolated from the mangrove endophytic fungus Xylaria sp. BL321 together with 07H239-A (4), a known analogue of the new compounds. The structures of these compounds were elucidated by analysis of their MS, 1D and 2D NMR spectroscopic data. Compound 4 showed activation activity on α-glucosidase at 0.15 μM (146%), and then, 4 gradually produced inhibitory activity on α-glucosidase with increasing concentration, and the IC50 value is 6.54 μM. Full article
Open AccessArticle Two New Tryptamine Derivatives, Leptoclinidamide and (-)-Leptoclinidamine B, from an Indonesian Ascidian Leptoclinides dubius
Mar. Drugs 2012, 10(2), 349-357; doi:10.3390/md10020349
Received: 27 December 2011 / Revised: 23 January 2012 / Accepted: 7 February 2012 / Published: 10 February 2012
Cited by 3 | PDF Full-text (237 KB) | HTML Full-text | XML Full-text
Abstract
Two new tryptamine-derived alkaloids, named as leptoclinidamide (1) and (-)-leptoclinidamine B (2), were isolated from an Indonesian ascidian Leptoclinides dubius together with C2-α-D-mannosylpyranosyl-L-tryptophan (3). The structure of 1 was assigned on the basis of [...] Read more.
Two new tryptamine-derived alkaloids, named as leptoclinidamide (1) and (-)-leptoclinidamine B (2), were isolated from an Indonesian ascidian Leptoclinides dubius together with C2-α-D-mannosylpyranosyl-L-tryptophan (3). The structure of 1 was assigned on the basis of spectroscopic data for 1 and its N-acetyl derivative (4). Compound 1 was an amide of tryptamine with two β-alanine units. Although the planar structure of 2 is identical to that of the known compound (+)-leptoclinidamine B (5), compound 2 was determined to be the enantiomer of 5 based on amino acid analysis using HPLC methods. Compounds 1 to 4 were evaluated for cytotoxicity against two human cancer cell lines, HCT-15 (colon) and Jurkat (T-cell lymphoma) cells, but none of the compounds showed activity. Full article
(This article belongs to the Special Issue Alkaloid Analogs)
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Open AccessArticle Antioxidant Activity of Hawaiian Marine Algae
Mar. Drugs 2012, 10(2), 403-416; doi:10.3390/md10020403
Received: 5 December 2011 / Revised: 6 February 2012 / Accepted: 6 February 2012 / Published: 15 February 2012
Cited by 33 | PDF Full-text (683 KB) | HTML Full-text | XML Full-text
Abstract
Marine algae are known to contain a wide variety of bioactive compounds, many of which have commercial applications in pharmaceutical, medical, cosmetic, nutraceutical, food and agricultural industries. Natural antioxidants, found in many algae, are important bioactive compounds that play an important role [...] Read more.
Marine algae are known to contain a wide variety of bioactive compounds, many of which have commercial applications in pharmaceutical, medical, cosmetic, nutraceutical, food and agricultural industries. Natural antioxidants, found in many algae, are important bioactive compounds that play an important role against various diseases and ageing processes through protection of cells from oxidative damage. In this respect, relatively little is known about the bioactivity of Hawaiian algae that could be a potential natural source of such antioxidants. The total antioxidant activity of organic extracts of 37 algal samples, comprising of 30 species of Hawaiian algae from 27 different genera was determined. The activity was determined by employing the FRAP (Ferric Reducing Antioxidant Power) assays. Of the algae tested, the extract of Turbinaria ornata was found to be the most active. Bioassay-guided fractionation of this extract led to the isolation of a variety of different carotenoids as the active principles. The major bioactive antioxidant compound was identified as the carotenoid fucoxanthin. These results show, for the first time, that numerous Hawaiian algae exhibit significant antioxidant activity, a property that could lead to their application in one of many useful healthcare or related products as well as in chemoprevention of a variety of diseases including cancer. Full article
(This article belongs to the Special Issue Marine Carotenoids and Oxidative Stress)
Open AccessCommunication Antihypertensive Effect of Long-Term Oral Administration of Jellyfish (Rhopilema esculentum) Collagen Peptides on Renovascular Hypertension
Mar. Drugs 2012, 10(2), 417-426; doi:10.3390/md10020417
Received: 25 December 2011 / Revised: 31 January 2012 / Accepted: 6 February 2012 / Published: 15 February 2012
Cited by 12 | PDF Full-text (160 KB) | HTML Full-text | XML Full-text
Abstract
Antihypertensive effect of long-term oral administration of jellyfish (Rhopilema esculentum) collagen peptides (JCP) on renovascular hypertension rats (RVHs) was evaluated. The systolic blood pressure and diastolic blood pressure of the RVHs were significantly reduced with administration of JCP (p < 0.05), compared with model control group. However, the arterial blood pressure of normal rats showed no significant changes during long-term oral treatment with high dose JCP (p > 0.05). Furthermore, effect of JCP on angiotensin II (Ang II) concentration of plasma had no significance (p > 0.05), but JCP significantly inhibited the Ang II concentration in RVHs’ kidney (p < 0.05). The kidney should be the target site of JCP. Full article
Open AccessArticle Terpenoids from the Octocorals Menella sp. (Plexauridae) and Lobophytum crassum (Alcyonacea)
Mar. Drugs 2012, 10(2), 427-438; doi:10.3390/md10020427
Received: 8 December 2011 / Revised: 6 February 2012 / Accepted: 9 February 2012 / Published: 15 February 2012
Cited by 12 | PDF Full-text (933 KB) | HTML Full-text | XML Full-text
Abstract
A new germacrane-type sesquiterpenoid, menelloide E (1), and a new cembrane-type diterpenoid, lobocrassin F (2), were isolated from the octocorals Menella sp. and Lobophytum crassum, respectively. The structures of terpenoids 1 and 2 were determined by spectroscopic [...] Read more.
A new germacrane-type sesquiterpenoid, menelloide E (1), and a new cembrane-type diterpenoid, lobocrassin F (2), were isolated from the octocorals Menella sp. and Lobophytum crassum, respectively. The structures of terpenoids 1 and 2 were determined by spectroscopic and chemical methods and compound 2 was found to display a significant inhibitory effect on the release of elastase by human neutrophils. Full article
Open AccessArticle Steroids from the Soft Coral Sinularia crassa
Mar. Drugs 2012, 10(2), 439-450; doi:10.3390/md10020439
Received: 9 January 2012 / Revised: 7 February 2012 / Accepted: 9 February 2012 / Published: 16 February 2012
Cited by 14 | PDF Full-text (591 KB) | HTML Full-text | XML Full-text
Abstract
One new sterol, crassarosterol A (1), and four new steroidal glycosides, crassarosterosides A–D (25) were isolated from the Formosan soft coral Sinularia crassa. The absolute configuration of 1 was determined using the Mosher’s method. The [...] Read more.
One new sterol, crassarosterol A (1), and four new steroidal glycosides, crassarosterosides A–D (25) were isolated from the Formosan soft coral Sinularia crassa. The absolute configuration of 1 was determined using the Mosher’s method. The absolute configurations for the sugar moieties of 25 were determined by HPLC analysis on the o-tolylthiocarbamates derived from the liberated sugar after acid hydrolysis. Compounds 2 and 4 could significantly inhibit the expression of pro-inflammatory iNOS protein at 10 µM. In contrast, 13 were found to stimulate the expression of COX-2 protein at this concentration. Steroids 1 and 4 also showed cytotoxicity toward the selected human liver cancer cells. Full article
Open AccessArticle Novel Marine Phenazines as Potential Cancer Chemopreventive and Anti-Inflammatory Agents
Mar. Drugs 2012, 10(2), 451-464; doi:10.3390/md10020451
Received: 27 December 2011 / Revised: 8 February 2012 / Accepted: 13 February 2012 / Published: 16 February 2012
Cited by 34 | PDF Full-text (407 KB) | HTML Full-text | XML Full-text
Abstract
Two new (1 and 2) and one known phenazine derivative (lavanducyanin, 3) were isolated and identified from the fermentation broth of a marine-derived Streptomyces sp. (strain CNS284). In mammalian cell culture studies, compounds 1, 2 and 3 inhibited [...] Read more.
Two new (1 and 2) and one known phenazine derivative (lavanducyanin, 3) were isolated and identified from the fermentation broth of a marine-derived Streptomyces sp. (strain CNS284). In mammalian cell culture studies, compounds 1, 2 and 3 inhibited TNF-α-induced NFκB activity (IC50 values of 4.1, 24.2, and 16.3 μM, respectively) and LPS-induced nitric oxide production (IC50 values of >48.6, 15.1, and 8.0 μM, respectively). PGE2 production was blocked with greater efficacy (IC50 values of 7.5, 0.89, and 0.63 μM, respectively), possibly due to inhibition of cyclooxygenases in addition to the expression of COX-2. Treatment of cultured HL-60 cells led to dose-dependent accumulation in the subG1 compartment of the cell cycle, as a result of apoptosis. These data provide greater insight on the biological potential of phenazine derivatives, and some guidance on how various substituents may alter potential anti-inflammatory and anti-cancer effects. Full article
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Open AccessArticle Anti-Melanogenic Property of Geoditin A in Murine B16 Melanoma Cells
Mar. Drugs 2012, 10(2), 465-476; doi:10.3390/md10020465
Received: 23 November 2011 / Revised: 29 December 2011 / Accepted: 3 February 2012 / Published: 16 February 2012
Cited by 8 | PDF Full-text (1240 KB) | HTML Full-text | XML Full-text
Abstract
Geoditin A, an isomalabaricane triterpene isolated from marine sponge Geodia japonica, has been demonstrated to induce apoptosis in leukemia HL60 cells and human colon HT29 cancer cells through an oxidative stress, a process also interfering with normal melanogenesis in pigment cells. [...] Read more.
Geoditin A, an isomalabaricane triterpene isolated from marine sponge Geodia japonica, has been demonstrated to induce apoptosis in leukemia HL60 cells and human colon HT29 cancer cells through an oxidative stress, a process also interfering with normal melanogenesis in pigment cells. Treatment of murine melanoma B16 cells with geoditin A decreased expression of melanogenic proteins and cell melanogenesis which was aggravated with adenylate cyclase inhibitor SQ22536, indicating melanogenic inhibition was mediated through a cAMP-dependent signaling pathway. Immunofluorescence microscopy and glycosylation studies revealed abnormal glycosylation patterns of melanogenic proteins (tyrosinase and tyrosinase-related protein 1), and a co-localization of tyrosinase with calnexin (CNX) and lysosome-associated membrane protein 1 (LAMP-1), implicating a post-translational modification in the ER and a degradation of tyrosinase in the lysosome. Taken together, potent anti-melanogenic property and the relatively low cytotoxicity of geoditin A have demonstrated its therapeutic potential as a skin lightening agent. Full article
Open AccessArticle Ovatoxin-a and Palytoxin Accumulation in Seafood in Relation to Ostreopsis cf. ovata Blooms on the French Mediterranean Coast
Mar. Drugs 2012, 10(2), 477-496; doi:10.3390/md10020477
Received: 8 December 2011 / Revised: 6 February 2012 / Accepted: 8 February 2012 / Published: 17 February 2012
Cited by 40 | PDF Full-text (1069 KB) | HTML Full-text | XML Full-text
Abstract
Dinoflagellates of the genus Ostreopsis are known to cause (often fatal) food poisoning in tropical coastal areas following the accumulation of palytoxin (PLTX) and/or its analogues (PLTX group) in crabs, sea urchins or fish. Ostreopsis spp. occurrence is presently increasing in [...] Read more.
Dinoflagellates of the genus Ostreopsis are known to cause (often fatal) food poisoning in tropical coastal areas following the accumulation of palytoxin (PLTX) and/or its analogues (PLTX group) in crabs, sea urchins or fish. Ostreopsis spp. occurrence is presently increasing in the northern to north western Mediterranean Sea (Italy, Spain, Greece and France), probably in response to climate change. In France, Ostreopsis. cf. ovata has been associated with toxic events during summer 2006, at Morgiret, off the coast of Marseille, and a specific monitoring has been designed and implemented since 2007. Results from 2008 and 2009 showed that there is a real danger of human poisoning, as these demonstrated bioaccumulation of the PLTX group (PLTX and ovatoxin-a) in both filter-feeding bivalve molluscs (mussels) and herbivorous echinoderms (sea urchins). The total content accumulated in urchins reached 450 µg PLTX eq/kg total flesh (summer 2008). In mussels, the maximum was 230 µg eq PLTX/kg (summer 2009) compared with a maximum of 360 µg found in sea urchins during the same period at the same site. This publication brings together scientific knowledge obtained about the summer development of Ostreopsis spp. in France during 2007, 2008 and 2009. Full article
Open AccessArticle A Sterol and Spiroditerpenoids from a Penicillium sp. Isolated from a Deep Sea Sediment Sample
Mar. Drugs 2012, 10(2), 497-508; doi:10.3390/md10020497
Received: 31 December 2011 / Revised: 1 February 2012 / Accepted: 13 February 2012 / Published: 20 February 2012
Cited by 13 | PDF Full-text (369 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new polyoxygenated sterol, sterolic acid (1), three new breviane spiroditerpenoids, breviones I–K (24), and the known breviones (58), were isolated from the crude extract of a Penicillium sp. obtained from a [...] Read more.
A new polyoxygenated sterol, sterolic acid (1), three new breviane spiroditerpenoids, breviones I–K (24), and the known breviones (58), were isolated from the crude extract of a Penicillium sp. obtained from a deep sea sediment sample that was collected at a depth of 5115 m. The structures of 14 were elucidated primarily by NMR experiments, and 1 was further confirmed by X-ray crystallography. The absolute configurations of 2 and 3 were deduced by comparison of their CD spectra with those of the model compounds. Compounds 2 and 5 showed significant cytotoxicity against MCF-7 cells, which is comparable to the positive control cisplatin. Full article
Open AccessArticle Cyanobacterial Neurotoxin β-N-Methylamino-L-alanine (BMAA) in Shark Fins
Mar. Drugs 2012, 10(2), 509-520; doi:10.3390/md10020509
Received: 19 January 2012 / Revised: 10 February 2012 / Accepted: 15 February 2012 / Published: 21 February 2012
Cited by 38 | PDF Full-text (823 KB) | HTML Full-text | XML Full-text
Abstract
Sharks are among the most threatened groups of marine species. Populations are declining globally to support the growing demand for shark fin soup. Sharks are known to bioaccumulate toxins that may pose health risks to consumers of shark products. The feeding habits [...] Read more.
Sharks are among the most threatened groups of marine species. Populations are declining globally to support the growing demand for shark fin soup. Sharks are known to bioaccumulate toxins that may pose health risks to consumers of shark products. The feeding habits of sharks are varied, including fish, mammals, crustaceans and plankton. The cyanobacterial neurotoxin β-N-methylamino-L-alanine (BMAA) has been detected in species of free-living marine cyanobacteria and may bioaccumulate in the marine food web. In this study, we sampled fin clips from seven different species of sharks in South Florida to survey the occurrence of BMAA using HPLC-FD and Triple Quadrupole LC/MS/MS methods. BMAA was detected in the fins of all species examined with concentrations ranging from 144 to 1836 ng/mg wet weight. Since BMAA has been linked to neurodegenerative diseases, these results may have important relevance to human health. We suggest that consumption of shark fins may increase the risk for human exposure to the cyanobacterial neurotoxin BMAA. Full article

Review

Jump to: Research

Open AccessReview Tetrodotoxin (TTX) as a Therapeutic Agent for Pain
Mar. Drugs 2012, 10(2), 281-305; doi:10.3390/md10020281
Received: 30 December 2011 / Revised: 19 January 2012 / Accepted: 19 January 2012 / Published: 31 January 2012
Cited by 37 | PDF Full-text (1168 KB) | HTML Full-text | XML Full-text
Abstract
Tetrodotoxin (TTX) is a potent neurotoxin that blocks voltage-gated sodium channels (VGSCs). VGSCs play a critical role in neuronal function under both physiological and pathological conditions. TTX has been extensively used to functionally characterize VGSCs, which can be classified as TTX-sensitive or [...] Read more.
Tetrodotoxin (TTX) is a potent neurotoxin that blocks voltage-gated sodium channels (VGSCs). VGSCs play a critical role in neuronal function under both physiological and pathological conditions. TTX has been extensively used to functionally characterize VGSCs, which can be classified as TTX-sensitive or TTX-resistant channels according to their sensitivity to this toxin. Alterations in the expression and/or function of some specific TTX-sensitive VGSCs have been implicated in a number of chronic pain conditions. The administration of TTX at doses below those that interfere with the generation and conduction of action potentials in normal (non-injured) nerves has been used in humans and experimental animals under different pain conditions. These data indicate a role for TTX as a potential therapeutic agent for pain. This review focuses on the preclinical and clinical evidence supporting a potential analgesic role for TTX. In addition, the contribution of specific TTX-sensitive VGSCs to pain is reviewed. Full article
(This article belongs to the Special Issue Tetrodotoxin)
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Open AccessReview Synthetic Strategies to Terpene Quinones/Hydroquinones
Mar. Drugs 2012, 10(2), 358-402; doi:10.3390/md10020358
Received: 26 December 2011 / Revised: 3 February 2012 / Accepted: 3 February 2012 / Published: 14 February 2012
Cited by 10 | PDF Full-text (632 KB) | HTML Full-text | XML Full-text
Abstract
The cytotoxic and antiproliferative properties of many natural sesquiterpene-quinones and -hydroquinones from sponges offer promising opportunities for the development of new drugs. A review dealing with different strategies for obtaining bioactive terpenyl quinones/hydroquinones is presented. The different synthetic approches for the preparation [...] Read more.
The cytotoxic and antiproliferative properties of many natural sesquiterpene-quinones and -hydroquinones from sponges offer promising opportunities for the development of new drugs. A review dealing with different strategies for obtaining bioactive terpenyl quinones/hydroquinones is presented. The different synthetic approches for the preparation of the most relevant quinones/hydroquinones are described. Full article
(This article belongs to the Special Issue Synthesis around Marine Natural Products)
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