Twilight Zone Sponges from Guam Yield Theonellin Isocyanate and Psammaplysins I and J (original) (raw)
Related papers
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).
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.
Cytotoxic Compounds Derived from Marine Sponges. A Review (2010–2012)
Molecules, 2017
This extensive review covers research published between 2010 and 2012 regarding new compounds derived from marine sponges, including 62 species from 60 genera belonging to 33 families and 13 orders of the Demospongia class (Porifera). The emphasis is on the cytotoxic activity that bioactive metabolites from sponges may have on cancer cell lines. At least 197 novel chemical structures from 337 compounds isolated have been found to support this work. Details on the source and taxonomy of the sponges, their geographical occurrence, and a range of chemical structures are presented. The compounds discovered from the reviewed marine sponges fall into mainly four chemical classes: terpenoids (41.9%), alkaloids (26.2%), macrolides (8.9%) and peptides (6.3%) which, along with polyketides, sterols, and others show a range of biological activities. The key sponge orders studied in the reviewed research were Dictyoceratida, Haplosclerida, Tetractinellida, Poecilosclerida, and Agelasida. Petrosia, Haliclona (Haplosclerida), Rhabdastrella (Tetractinellida), Coscinoderma and Hyppospongia (Dictyioceratida), were found to be the most promising genera because of their capacity for producing new bioactive compounds. Several of the new compounds and their synthetic analogues have shown in vitro cytotoxic and pro-apoptotic activities against various tumor/cancer cell lines, and some of them will undergo further in vivo evaluation.
Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa
Química Nova, 2012
Nine bromotyrosine-derived compounds were isolated from the Caribbean marine sponge Verongula rigida. Two of them, aeroplysinin-1 (1) and dihydroxyaerothionin (2), are known compounds for this species, and the other seven are unknown compounds for this species, namely: 3,5-dibromo-N,N,N-trimethyltyraminium (3), 3,5-dibromo-N,N,N, O-tetramethyltyraminium (4), purealidin R (5), 19-deoxyfistularin 3 (6), purealidin B , 11-hydroxyaerothionin (8) and fistularin-3 (9). Structural determination of the isolated compounds was performed using one-and two-dimensional NMR, MS and other spectroscopy data. All isolated compounds were screened for their in vitro activity against three parasitic protozoa: Leishmania panamensis, Plasmodium falciparum and Trypanosoma cruzi. Compounds 7 and 8 showed selective antiparasitic activity at 10 and 5 µM against Leishmania and Plasmodium parasites, respectively. Cytotoxicity of these compounds on a human promonocytic cell line was also assessed.
Marine Drugs, 2019
So far, the Futuna Islands located in the Central Indo-Pacific Ocean have not been inventoried for their diversity in marine sponges and associated chemical diversity. As part of the Tara Pacific expedition, the first chemical investigation of the sponge Narrabeena nigra collected around the Futuna Islands yielded 18 brominated alkaloids: seven new bromotryptamine derivatives 1-7 and one new bromotyramine derivative 8 together with 10 known metabolites of both families 9-18. Their structures were deduced from extensive analyses of nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) data. In silico metabolite anticipation using the online tool MetWork revealed the presence of a key and minor biosynthetic intermediates. These 18 compounds showed almost no cytotoxic effect up to 10 µM on human neuroblastoma SH-SY5Y and microglia BV2 cells, and some of them exhibited an interesting neuroprotective activity by reducing oxidative damage.
Structure–Activity Relationship of Cytotoxic Natural Products from Indonesian Marine Sponges
Revista Brasileira de Farmacognosia
Indonesian marine natural products have been one of the most promising sources in the race to obtain potential drugs for cancer treatment. One of the primary producers of cytotoxic compounds is sponges. However, there are still limited sources of comprehensive reviews related to the relationship between the structure of isolated compounds and their cytotoxic activity. This review remarks the attempt to provide a preliminary guidance from the perspective of structure-activity relationship and its participation on marine natural products research. This guidance is segregated by the compound's classes and their cytotoxic targets to obtain and organized a reliable summary of inter-study of the isolated compounds and their cytotoxicity. Structure-activity relationship is well-known for its ability to tune the bioactivity of a specific compound, especially on synthetic organic chemistry and in silico study but rarely used on natural product chemistry. The present review is intended to narrow down the endless possibilities of cytotoxicity by giving a predictable structure-activity relationship for active compounds. In addition, bioactive framework leads were selected by uncovering a noticeable structure-activity relationship with the intervention of cytotoxic agents from natural sources, especially Indonesian marine sponge.
Bioactive Metabolites from the Caribbean Sponge Aka coralliphagum
Journal of Natural Products, 2007
The chemistry of the burrowing sponge Aka coralliphagum was investigated to identify chemically labile secondary metabolites. The HPLC-MS analysis of the two growth forms typica and incrustans revealed different metabolites. The previously unknown sulfated compounds siphonodictyals B1 to B3 (6-8), corallidictyals C (9) and D (10), and siphonodictyal G (11) were isolated, and their structures were elucidated by NMR and MS experiments. The compounds were tested in a DPPH assay, in antimicrobial assays against bacteria, yeasts, and fungi, and in antiproliferation assays using cultures of mouse fibroblasts. The biological activity was linked to the presence of the ortho-hydroquinone moiety.
Chemical examination of the Sponge Phycopsis sp.
Chemical & pharmaceutical bulletin 57, 990–2 (2009)
Two new compounds 7a a,8a a-epoxy theonellin isothiocyanate (1) and 5a a,8a a-epidioxyergosta-6Z,22Z,25-trien-3b b-ol (2) along with two known compounds, theonellin isothiocyanate (3) and theonellin formamide (4) have been isolated from the sponge Phycopsis sp. Compound 2 showed cytotoxic activity against HL-60 and U937 human cancer cell lines with IC 50 values of 5.96؎0.02 and 31.72؎0.55 m mg/ml, respectively. Key words 7a,8a-epoxy theonellin isothiocyanate; cytotoxic activity; Phycopsis sp.; 5a,8a-epidioxyergosta-6Z,22Z,25-trien-3b-ol Chem. Pharm. Bull. 57(9) 990-992 (2009)