Swinhoeiamide A, a New Highly Active Calyculin Derivative from the Marine Sponge Theonella s winhoei (original) (raw)
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In our search for bioactive metabolites from marine organisms, we have investigated the polar fraction of the organic extract of the Red Sea sponge Theonella swinhoei. Successive chromatographic separations and final HPLC purification of the potent antifungal fraction afforded a new bicyclic glycopeptide, theonellamide G (1). The structure of the peptide was determined using extensive 1D and 2D NMR and high-resolution mass spectral determinations. The absolute configuration of theonellamide G was determined by chemical degradation and 2D NMR spectroscopy. Theonellamide G showed potent antifungal activity towards wild and amphotericin B-resistant strains of
Bioactive Compounds from Marine Sponges: Fundamentals and Applications
Marine Drugs
Marine sponges are sessile invertebrates that can be found in temperate, polar and tropical regions. They are known to be major contributors of bioactive compounds, which are discovered in and extracted from the marine environment. The compounds extracted from these sponges are known to exhibit various bioactivities, such as antimicrobial, antitumor and general cytotoxicity. For example, various compounds isolated from Theonella swinhoei have showcased various bioactivities, such as those that are antibacterial, antiviral and antifungal. In this review, we discuss bioactive compounds that have been identified from marine sponges that showcase the ability to act as antibacterial, antiviral, anti-malarial and antifungal agents against human pathogens and fish pathogens in the aquaculture industry. Moreover, the application of such compounds as antimicrobial agents in other veterinary commodities, such as poultry, cattle farming and domesticated cats, is discussed, along with a brief d...
Journal of the Marine Biological Association of India, 2016
A variety of biologically active compounds with unique structures and pharmacological properties have been reported to occur in marine organisms. Demospongiae, an important class of marine sponge is known for producing the largest number and diversity of secondary metabolites isolated till recent times. The review covers the diverse class of bioactive compounds isolated for therapeutic drug applications from different marine organisms. It is an attempt to update the marine research community with results of our ongoing search for bioactive secondary metabolites from marine sponge Spongosorites halichondriodes which has exhibited antibacterial, antifungal, cytotoxic, anti-inflammatory and immunomodulatory activity in our studies. Spongosorites halichondriodes (order Halichondrida, family Halichondriidae) is a predominant marine sponge collected from west coast of Mumbai, India. The sponge S. halichondriodes has shown presence of Octadecadienoic acid (Linoleic acid), ergostan tetraen-ol, dihydroxy cholanoic-methyl esters,C 28 saturated and unsaturated esters like 3β, 4β, 7α, 12α-tetrahydroxy-5β-cholan-24-oic acid methyl ester, 7α, 12β-dihydroxy-5β-cholan24-oic acid methyl ester, novel isocoumarin citrinolactone A, a triterpenoid glycyrrhetinic acid as well as other unknown compounds such as nucleoside inosine.
Bioactive compounds from coral reef invertebrates
Pure and Applied Chemistry, 2001
Manzamine A (1) known as a cytotoxin exhibited potent antimalarial activity with 40% recovery 60 days after single intraperitoneal (i.p.) injection against mice infected with the malaria parasite Plasmodium berghei. Pachastrisamine (6), a simple derivative of a sphingosine, isolated from a sponge, Pachastrissa sp. showed a high level of cytotoxicity. New sesquiterpene carbonimidic dichlorides and related aldehydes (812) have been isolated as cytotoxic constituents of the sponge Stylotella aurantium and shown to have moderate cytotoxicity. Cyclic undecapeptides, barangamides AD (1316), have been isolated from the sponge Theonella swinhoei. Their structures were established by spectroscopic analysis and chemical reaction.
Inhibitory Activity of Marine Sponge-Derived Natural Products against Parasitic Protozoa
Marine Drugs, 2010
In this study, thirteen sponge-derived terpenoids, including five linear furanoterpenes: furospinulosin-1 (1), furospinulosin-2 (2), furospongin-1 (3), furospongin-4 (4), and demethylfurospongin-4 (5); four linear meroterpenes: 2-(hexaprenylmethyl)-2methylchromenol (6), 4-hydroxy-3-octaprenylbenzoic acid (7), 4-hydroxy-3-tetraprenylphenylacetic acid (8), and heptaprenyl-p-quinol (9); a linear triterpene, squalene (10); two spongian-type diterpenes dorisenone D (11) and 11β-acetoxyspongi-12-en-16-one (12); a scalarane-type sesterterpene; 12-epi-deoxoscalarin (13), as well as an indole alkaloid, tryptophol were screened for their in vitro activity against four parasitic protozoa; Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Leishmania donovani and Plasmodium falciparum. Cytotoxic potential of the compounds on mammalian cells was also assessed. All compounds were active against T. brucei rhodesiense, with compound 8 being the most potent (IC 50 0.60 μg/mL), whereas 9 and 12 were the most active compounds against T. cruzi, with IC 50 values around 4 μg/mL. Compound 12 showed the strongest leishmanicidal activity (IC 50 0.75 μg/mL), which was comparable to that of miltefosine (IC 50 0.20 μg/mL). The best antiplasmodial effect was exerted by compound 11 (IC 50 0.43 μg/mL), followed by compounds 7, 10, and 12 with IC 50 values around 1 μg/mL. Compounds 9, 11 and 12 exhibited, besides their antiprotozoal activity, also some cytotoxicity, whereas all other compounds had low or no cytotoxicity towards the
Bioactive compounds from marine sponges
Several marine sponges from Okinawan waters have been examined for bioactive compounds. Further investigation with Polyfibrospongia sp. which have already yielded novel metabolites gave new hennoxazoles (6-9), of which 7 was moderately cytotoxic. Echinocluthn'a sp. furnished new pyridine alkaloids (1 0-1 2), two of which showed immunosuppressive activity. A sponge identified to be Dysidea herbacea afforded cytotoxic 20,24-dimethyldeoxoscalarin-3-one ( 1 4) along with known diterpenes. Two cytotoxic dimers (15,16) of a sesquiterpene have been isolated from Halichondria sp. Mytiloxanthin derivatives (1 8,19) were the major pigments of Phakellia stellidem. A new species of the family Niphatidae gave highly cytotoxic polyacetylenes (2 0-2 6).
Isolation and Structure Elucidation of Bioactive Secondary Metabolites from Marine Sponges
docserv.uni-duesseldorf.de
Cytotoxic cyclic peptide……………………………………………………..….170 Biosynthesis of peptides………………………………………………………...171 Relationship between structures and cytotoxic activities of callyaerins …….....174 4.2. Metabolites isolated from the sponge Diacarnus megaspinorhabdosa…...…174 Cytotoxic norterpene peroxides…………………………………………………174 Proposed biosynthesis of terpene peroxides……………………..…………...…175 Mechanism of the antimalarial activity of cyclic peroxides…………………….177 Structure activity relationship of norterpene cyclic peroxides…………….……178 Indole, phenolic and nucleoside derivatives.………………………………...…179 Mechanism of action of nucleoside analogs.
New Luffariellolide Derivatives from the Indonesian Sponge Acanthodendrilla sp
Journal of Natural Products, 2004
Investigation of the Indonesian sponge Acanthodendrilla sp. afforded five new luffariellolide-related sesterterpenes, acantholides A-E (1-5), in addition to luffariellolide and its 25-O-methyl and 25-Oethyl derivatives. All structures were unambiguously established by 1D and 2D NMR and MS spectroscopy. Acantholide D and E are derivatives comprising the 1-acetylcyclopentan-5-ol moiety, which are new variants of the C 14 -C 20 segment for this type of linear sesterterpenes. Luffariellolide and its 25-O-methyl congener as well as acantholide E (5) were cytotoxic against the mouse lymphoma L5187Y cell line. Acantholide B (2), luffariellolide, and its 25-O-methyl congener were active against the Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis, the Gram-negative bacterium Escherichia coli, the yeast Candida albicans, and the plant pathogenic fungus Cladosporium herbarum.