Marine Sponge Derived Natural Products between 2001 and 2010: Trends and Opportunities for Discovery of Bioactives
Abstract
:1. Introduction
2. New Compounds and Their Distribution 2001–2010
2.1. Yearly Distribution of Phyla that Produce Natural Products Discovered from 2001 to 2010
2.2. Sponges (Porifera) as a Source of New Natural Products and Drugs for the Future
2.3. The Distribution of New Marine Natural Products from Sponges
Order | Number of Families | Number of Genera | Number of Species | Number of References |
---|---|---|---|---|
Agelasida | 9 | 9 | 21 | 24 |
Astrophorida | 26 | 58 | 63 | 62 |
Axinellida | 2 | 2 | 2 | 2 |
Chondrosida | 1 | 1 | 1 | 1 |
Choristida | 3 | 3 | 3 | 3 |
Clathrinida | 5 | 5 | 7 | 7 |
Dendroceratida | 7 | 10 | 11 | 13 |
Dictyoceratida | 40 | 117 | 145 | 161 |
Hadromerida | 24 | 31 | 32 | 33 |
Halichondrida | 31 | 69 | 86 | 84 |
Haplosclerida | 52 | 80 | 100 | 120 |
Homosclerophorida | 10 | 20 | 39 | 50 |
Leucosolenida | 1 | 1 | 1 | 1 |
Lithistida | 14 | 20 | 23 | 32 |
Lyssacinosida | 2 | 2 | 2 | 2 |
Ocilosclerida | 1 | 1 | 1 | 2 |
Poecilosclerida | 67 | 68 | 81 | 83 |
Spirophorida | 4 | 4 | 4 | 5 |
Unknown | 8 | 12 | 12 | 10 |
Verongida | 27 | 29 | 37 | 46 |
Total | 334 | 542 | 671 | 741 |
2.4. Distribution of New Compounds per Species from Different Orders
2.5. Symbiotic Relationships: Sponge Associated Microorganisms
2.6. The Distribution of Chemical Classes
2.7. The Distribution of Bioactive Compounds
Orders of Sponges | Anti-Alzheimer’s | Antibacterial | Antituberculosis | Anticancer/Cytotoxicity | Antifungal | Anti-inflammatory | Antimalarial | Anti-HIV | Antiviral | Miscellaneous | Total |
---|---|---|---|---|---|---|---|---|---|---|---|
Agelasida | 0 | 17 | 0 | 11 | 6 | 0 | 6 | 0 | 0 | 14 | 54 |
Astrophorida | 0 | 8 | 6 | 97 | 7 | 0 | 1 | 5 | 3 | 22 | 149 |
Axinellida | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 8 | 8 |
Chondrosida | 0 | 0 | 0 | 3 | 3 | 0 | 0 | 0 | 0 | 0 | 6 |
Choristida | 0 | 0 | 0 | 12 | 0 | 0 | 0 | 0 | 0 | 12 | 24 |
Clathrinida | 0 | 4 | 3 | 3 | 2 | 0 | 0 | 0 | 0 | 0 | 12 |
Dendroceratida | 0 | 4 | 0 | 14 | 3 | 3 | 0 | 0 | 0 | 14 | 38 |
Dictyoceratida | 0 | 38 | 3 | 182 | 11 | 2 | 1 | 5 | 0 | 90 | 332 |
Hadromerida | 0 | 2 | 3 | 45 | 1 | 0 | 0 | 5 | 0 | 18 | 74 |
Halichondrida | 1 | 18 | 4 | 99 | 16 | 1 | 2 | 1 | 0 | 31 | 173 |
Haplosclerida | 8 | 15 | 2 | 100 | 20 | 0 | 7 | 4 | 0 | 73 | 229 |
Homosclerophorida | 0 | 2 | 3 | 55 | 10 | 0 | 9 | 1 | 0 | 34 | 114 |
Leucosolenida | 0 | 1 | 0 | 2 | 0 | 0 | 0 | 0 | 0 | 0 | 3 |
Lithistida | 0 | 5 | 2 | 38 | 9 | 2 | 0 | 16 | 0 | 16 | 88 |
Lyssacinosida | 0 | 0 | 0 | 1 | 0 | 0 | 0 | 0 | 0 | 0 | 1 |
Ocilosclerida | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
Poecilosclerida | 0 | 17 | 5 | 143 | 21 | 1 | 1 | 4 | 1 | 34 | 227 |
Spirophorida | 0 | 0 | 0 | 4 | 0 | 0 | 0 | 0 | 0 | 0 | 4 |
Unknown | 0 | 0 | 0 | 2 | 0 | 0 | 0 | 0 | 0 | 7 | 9 |
Verongida | 0 | 14 | 0 | 17 | 5 | 0 | 0 | 0 | 0 | 34 | 70 |
Total | 9 | 145 | 31 | 828 | 114 | 9 | 27 | 41 | 4 | 407 | 1615 |
Organism | Order | Compound Name | Chemical Class | Special Feature/Activity | Source, Country, Year,/Depth | Reference |
---|---|---|---|---|---|---|
Sarcotragus sp. | Dictyoceratida | Sarcotragin A, & B | Trisnorsesterterpenoid lactam | Showed moderate cytotoxicity (LC50 207 μg/mL) toward the leukemia cell-line K562 | Seoguipo, Jaeju Island, Korea, 2001 | [146] |
Polymastia tenax | Hadromerida | 5α,6α-epoxy-24R*-ethylcholest-8(14)-en-3β,7α-diol and 5α,6α-epoxy-24R*-ethylcholest-8-en-3β,7α-diol | Sterol | Exhibited significant cytotoxic activity vs. human lung carcinoma (A-549), human colon carcinomas (HT-29 and H-116), and human prostate carcinoma (PC-3) cell lines with the LC50 (μg/mL) value of 5–10, 1–5, 1–5, 0.5–1 and 1–5 | Punta de Betín, Bahía de Santa Marta, in the Colombian Caribbean, Colombia, 2002 | [147] |
Crella spinulata | Poecilosclerida | Benzylthiocrellidone | Bis-dimedone thioether | First report of a natural product containing a dimedone moiety. No activity reported | Davies and Bowden Reefs Australia, 2002 | [148] |
Ectyoplasia ferox | Poecilosclerida | Ectyoceramide | Galactofuranosylceramide (GSL) | The first example of a monohexofuranosylceramide and the first natural GSL with its first sugar in the furanose form. No activity reported | Island of Rum Cay, Bahamas, 2000 | [149] |
Cribrochalina olemda | Haplosclerida | Kapakahine E | Peptide (cyclic) | Kapakahine E showed moderate cytotoxicity against P388 murine leukemia cells at IC50 of 5.0 μg/mL | Pohnpei, Micronesia, 2003 | [150] |
Haliclona Viscosa | Haplosclerida | Viscosamine | Trimeric 3-alkyl pyridinium alkaloid | First trimeric 3-alkyl pyridinium compound from a marine environment. No activity reported | Coast of Blomstrandhalvøya, near Hansneset, Kongsfjorden, Arctic Ocean, 2003 | [151] |
Phakellia fusca | Axinellida | Compound 1, 2, 3 | 5-Fluorouracil alkaloid | First report of fluorine containing natural products from a marine source. No activity reported | Yongxiong Island of the Xisha Islands, South China Sea, China 2003 | [152] |
Agelas clathrodes | Agelasida | Clarhamnoside | Rhamnosylated R-Galactosylceramide | The first Rhamnosylated R-Galactosylceramide, a glycolipid containing an unusual l-rhamnose unit. No activity reported | Grand Bahamas Island (Sweetings Cay), Bahamas, 2004 | [153] |
Psammocinia sp. | Dictyoceratida | Psymberin | Cytotoxin (distantly related to the Pederin family) | Several melanoma, breast, and colon cancer cell lines demonstrated high sensitivity (LC50 < 2.5 × 10−9 M) to psymberin, and all six leukemia cell lines proved comparably insensitive | Papua New Guinea, 2004 | [154] |
Callyspongia abnormis | Haploscerida | Callynormine A | Cyclic Peptide | Represents a new class of heterodetic cyclic peptides (designated endiamino peptides). This compound possessing an α-amido-β-aminoacrylamide cyclization functionality | Shimoni reef, Kenya, 2004 | [155] |
Axinella infundibula | Halichondrida | Axinelloside A | Lipopolysaccharide (Sulfated) | Axinelloside A, a complex polysulfated glycolipid, which strongly inhibited the activity of human telomerase with an IC50 value of 0.4 μM | Shikine-jima Island, the Izu Islands, Japan, 2005 | [156] |
Theonella swinhoei | Lithistida | Plytheonamide A, B | Polypeptide | Showed cytotoxicity against P388 murine leukemia cells with IC50 values of 78 and 68 pg/mL, respectively. Linear polypeptides with unprecedented structural features | Hachijo-jima Island, Japan, 2005 | [157] |
Neopetrosia sp. | Haplosclerida | Neopetrosiamide A, B | Peptide (diastereomeric tricyclic) | Active in inhibiting the amoeboid invasion by human tumor cells | Near Milne Bay, Papua New Guinea, 2005 | [158] |
Prianos osiros | Haplosclerida | (3 R,3′R,5S)-3,3′,5,19′-tetrahydroxy-7′,8′-didehydro-γ,ε-carotene-8-one | Acetylenic carotenoid | Contains an unusual cytotoxic carotenoid | Pohnpei, Micronesia, 2005 | [159] |
Ircinia sp. | Dictyoceratida | Irciniasulfonic acid B | Fatty acid derivative (taurine conjugated) | Reversed the multi-drug resistance to vincristine in KB/VJ300 cells at the concentration of 100 μM | Tsuzumi Island, Fukuoka Prefecture, Japan, 2006 | [160] |
Suberites japonicus | Hadromerida | Seragamide A–F | Depsipeptide (actin targeting) | Caused multinuclei formation in cells at 0.01–0.02 μg/mL | Seragaki, Okinawa, Japan, 2006 | [161] |
Theonella swinhoei | Lithistida | Hurghadolide A | Macrolide | Caused disruption of the actin cytoskeleton at concentrations of 7.3 nM. Active against Candida albicans (MIC 31.3 μg/mL) | Red Sea, Egypt, 2006 | [89] |
Theonella swinhoei | Lithistida | Swinholide I | Macrolide | as above | Red Sea, Egypt, 2006 | [89] |
Coelocarteria cfr. singaporensis | Poecilosclerida | Coelodiol and Coelic acid | Diterpene (ent-isocopalane) | Inhibit the in vitro growth of MKN-45 cell line (human gastric adenocarcinoma) at 20 and 40 μg/mL respectively | Bunaken, Marine Park (North Sulawesi), Indonesia, 2006 | [162] |
Lendenfeldia sp. | Dictyoceratida | ( S)-2,2′-Dimethoxy-1,1′-binaphthyl-5,5′,6,6′-tetraol | Naphthalene dimer | Significantly inhibited both hypoxia-induced (IC50 values 4.3 µM) and iron chelator (1, 10-phenanthroline)-induced HIF-1 activation in T47D breast tumor cells. This compound inhibited HIF-1 activation at concentrations that were significantly lower than those that suppressed tumor cell viability | Collected at 2 m depth on May 22, 1993 (sample C011337), from a sea grass bed, Indonesia, 2007 | [163] |
Erylus formosus | Astrophorida | Eryloside F1–F4 | Triterpene glycoside | At a concentration of 100 μg/mL were found to activate Ca2 influx into mouse spleenocytes. biosides having aglycons related to penasterol with additional oxidation patterns in their side chains | Puerto Morelos (the Caribbean Sea), Mexico 2007 | [164] |
Erylus formosus | Astrophorida | Eryloside M–Q | Triterpene glycoside | As above, contain new variants of carbohydrate chains with three, four and six sugar units. Contain 14-carboxy-24-methylenelanost-8(9)-en-3β-ol | Puerto Morelos (the Caribbean Sea), Mexico, 2007 | [164] |
Cacospongia mycofijiensis | Dictyoceratida | CTP-431 | Thiopyrone | Showed only mild cytotoxicity (IC50: 18 μM) against human colon carcinoma HCT-116. This compound has no previous precedent in natural products chemistry. Its structure including absolute configuration as 8R,9R,10S,13S | Beqa Lagoon, Fiji, 2008 | [165] |
Homophymia sp. | Lithistida | Homophymine A | Cyclodepsipeptide | Exhibited cytoprotective activity against HIV-1 infection with a IC50 of 75 nM | Coast of New Caledonia, 2008 | [166] |
Ianthella sp. | Verongida | Petrosterol-3,6-dione and 5α,6α-epoxy-petrosterol | C29 sterol | Showed growth-inhibitory effects with IC50 values of 8.4, 19.9, 17.8, 16.2 and 22.1 μM against lung (A549), colon (HT-29), breast (MCF-7), ovary (SK-OV-3), and two types of leukemia (HL-60 and U937) human cancer cell lines | Namyet Island, Khanh Hoa province, Vietnam, 2009 | [167] |
Topsentia sp. | Halichondrida | Geodisterol-3- O-sulfite and 29-demethylgeodisterol-3-O-sulfite | Sterol (sulphated) | Reverses efflux pump mediated fluconazole resistance. Also enhances fluconazole activity in a Saccharomyces cerevisiae strain overexpressing the Candida albicans efflux pump MDR1, as well as in a fluconazole-resistant Candida albicans clinical isolate known to overexpress MDR1 | Chuuk, Micronesia, 2009 | [168] |
Spongia (Heterofibria) sp. | Dictyoceratida | Heterofibrin A1–A3 and B1–B3 | Fatty acid | Possess a diyne-ene moiety, while the monolactyl and dilactyl moiety featured in selected heterofibrins is unprecedented in the natural products literature. Inhibited lipid droplet formation in A431 fibroblast cells (up to 60% at 10 μM) | Great Australian Bight, Australia, 2010 | [169] |
Xestospongia sp. | Haplosclerida | Xestosaprol F–M | Xestosaprol (pentacyclic compound) | Showed moderate inhibition of the aspartic protease BACE1 (memapsin-2), which has a central role in the etiology of Alzheimer’s disease with the IC50 value of 135 ± 11 μM. First examples of a monooxygenated A-ring | Coral reef at Sangalaki, Indonesia, 2010 | [170] |
Theonella swinhoei | Lithistida | Paltolides A–C | Peptides (Anabaenopeptin like) | Closely related to a group of anabaenopeptins that are submicromolar inhibitors of carboxypeptidase U with greater than 50 fold selectivity over other carboxypeptidases | Uchelbeluu Reef, Palau, 2010 | [171] |
Neopetrosia proxima | Haplosclerida | Neopetrosiamine A | Alkaloid (tetracyclic bis-piperidine) | Exhibited strong inhibitory activity against MALME-3M melanoma cancer, CCRF-CEM leukemia, and MCF7 breast cancer with IC50 values of 1.5, 2.0, and 3.5 μM, respectively. In vitro activity vs. pathogenic strain of Mycobacterium tuberculosis (H37Rv) and Plasmodium falciparum | Mona Island, Puerto Rico, 2010 | [172] |
Iotrochota baculifera | Poecilosclerida | Baculiferins A–O | O-sulfated pyrrole alkaloids | Baculiferins C, E–H, and K–N (4, 6–9, 12–15) are potent inhibitors of HIV-1 IIIB virus in both MT4 and MAGI cells. Additionally could bind to the HIV-1 target proteins Vif, APOBEC3G, and gp41 | Inner coral reef, Hainan Island, China, 2010 | [173] |
2.8. Distribution of New Compounds Based on Country/Geographical Area
3. Conclusions
Supplementary Files
Supplementary File 1Acknowledgments
Author Contribution
Conflicts of Interest
References
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Mehbub, M.F.; Lei, J.; Franco, C.; Zhang, W. Marine Sponge Derived Natural Products between 2001 and 2010: Trends and Opportunities for Discovery of Bioactives. Mar. Drugs 2014, 12, 4539-4577. https://doi.org/10.3390/md12084539
Mehbub MF, Lei J, Franco C, Zhang W. Marine Sponge Derived Natural Products between 2001 and 2010: Trends and Opportunities for Discovery of Bioactives. Marine Drugs. 2014; 12(8):4539-4577. https://doi.org/10.3390/md12084539
Chicago/Turabian StyleMehbub, Mohammad Ferdous, Jie Lei, Christopher Franco, and Wei Zhang. 2014. "Marine Sponge Derived Natural Products between 2001 and 2010: Trends and Opportunities for Discovery of Bioactives" Marine Drugs 12, no. 8: 4539-4577. https://doi.org/10.3390/md12084539