image:Halichondria and Eribulin.jpg (Halaven) precursor halichondrin B]]
Lacking an immune system, protective shell, or mobility, sponges have developed an ability to synthesize a variety of unusual compounds for survival. C-nucleosides isolated from Caribbean Cryptotethya crypta, were the basis for the synthesis of zidovudine (AZT), aciclovir (Cyclovir), cytarabine (Depocyt), and cytarabine derivative gemcitabine (Gemzar).
class="wikitable" style="width: 60%; float: center; font-size: 90%; margin-left: 25px;" |
scope="col" style="width: 70px;" | Isolate
! scope="col" width="100px" | Source
! scope="col" width="160px" | Researched activity / Chemical description |
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3-Alkylpyridinium (3-AP)
|Haplosclerida
| style="text-align: center;" |hemolytic and cytotoxic[{{cite journal |last1=SepčIć |first1=Kristina |last2=Guella |first2=Graziano |last3=Mancini |first3=Ines |last4=Pietra |first4=Francesco |last5=Serra |first5=Mauro Dalla |last6=Menestrina |first6=Gianfranco |last7=Tubbs |first7=Kemmons |last8=MačEk |first8=Peter |last9=Turk |first9=Tom |year=1997 |title=Characterization of Anticholinesterase-Active 3-Alkylpyridinium Polymers from the Marine Sponge Reniera saraiin Aqueous Solutions |journal=Journal of Natural Products |volume=60 |issue=10 |pages=991–996 |doi=10.1021/np970292q |pmid=9358641}}] |
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Agosterol A
|
| style="text-align: center;" |anticancer[{{cite journal |last1=Chen |first1=Zhe-Sheng |last2=Aoki |first2=Shunji |last3=Komatsu |first3=Masaharu |last4=Ueda |first4=Kazumitsu |last5=Sumizawa |first5=Tomoyuki |last6=Furukawa |first6=Tatsuhiko |last7=Okumura |first7=Hiroshi |last8=Ren |first8=Xiao-Qin |last9=Belinsky |first9=Martin G. |last10=Lee |first10=Kun |last11=Kruh |first11=Gary D. |year=2001 |title=Reversal of drug resistance mediated by multidrug resistance protein (MRP) 1 by dual effects of agosterol a on MRP1 function |journal=International Journal of Cancer |volume=93 |issue=1 |pages=107–113 |doi=10.1002/ijc.1290 |issn=0020-7136 |doi-access=free |last13=Akiyama |first13=Shin-ichi |first12=Motomasa |last12=Kobayashi|pmid=11391629 }}][{{cite journal |last1=Aoki |first1=Shunji |last2=Chen |first2=Zhe-Sheng |last3=Higasiyama |first3=Kimihiko |last4=Setiawan |first4=I |last5=Akiyama |first5=Shin-ichi |last6=Kobayashi |first6=Motomasa |year=2001 |title=Reversing Effect of Agosterol A, a Spongean Sterol Acetate, on Multidrug Resistance in Human Carcinoma Cells |journal=Japanese Journal of Cancer Research |volume=92 |issue=8 |pages=886–895 |doi=10.1111/j.1349-7006.2001.tb01177.x |pmid=11509122 |issn=0910-5050 |pmc=5926837}}] |
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Aplyzanzine A
|Aplysina sp.
| |
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Avarol
|Dysidea avara
| style="text-align: center;" |antitumor, antimicrobial[Asian Journal of Chemistry; Vol. 26, No. 23 (2014), 8255-8256] and antiviral[Sagar, S.; Kaur, M.; Minneman, K. P. Antiviral Lead Compounds from Marine Sponges. Marine Drugs 2010, 8 (10), 2619–2638] effects |
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Aciculitin
| Aciculites ciliate
| style="text-align: center;" | antifungal cyclic peptide |
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Discodermin
| Discodermia kiiensis
| style="text-align: center;" | antimicrobial tetradecapeptide |
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Dysidenin
|Lamellodysidea herbacea
| style="text-align: center;" |Highly toxic[{{cite journal |last1=Van Sande |first1=J |last2=Deneubourg |first2=F |last3=Beauwens |first3=R |last4=Braekman |first4=JC |last5=Daloze |first5=D |last6=Dumont |first6=JE |date=April 1990 |title=Inhibition of iodide transport in thyroid cells by dysidenin, a marine toxin, and some of its analogs. |journal=Molecular Pharmacology |volume=37 |issue=4 |pages=583–9 |pmid=2157965}}] |
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Girolline
| Girolline
| style="text-align: center;" | inhibits protein synthesis[{{cite journal| pmid=22620987 | doi=10.1021/np300102z | volume=75 | title=Synthesis and biological evaluation of purpurealidin E-derived marine sponge metabolites: aplysamine-2, aplyzanzine A, and suberedamines A and B | year=2012 | journal=J Nat Prod | pages=1090–101 | last1 = Kottakota | first1 = SK | last2 = Evangelopoulos | first2 = D | last3 = Alnimr | first3 = A | last4 = Bhakta | first4 = S | last5 = McHugh | first5 = TD | last6 = Gray | first6 = M | last7 = Groundwater | first7 = PW | last8 = Marrs | first8 = EC | last9 = Perry | first9 = JD | last10 = Spilling | first10 = CD | last11 = Harburn | first11 = JJ| issue=6 }}] |
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Halichondrin B
| Halichondria okadai Kadota (Miura Peninsula)
| style="text-align: center;" | precursor to eribulin (Halaven)[{{cite journal |vauthors=Towle MJ, Salvato KA, Budrow J, Wels BF, Kuznetsov G, Aalfs KK, etal | title=In vitro and in vivo anticancer activities of synthetic macrocyclic ketone analogues of halichondrin B. | journal=Cancer Res | year= 2001 | volume= 61 | issue= 3 | pages= 1013–21 | pmid=11221827 | url=https://pubmed.ncbi.nlm.nih.gov/11221827 }}][https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm233863.htm]{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}} |
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Halicylindramide
| Halichondria
| style="text-align: center;" | antifungal peptide |
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Hymenamides
| Phakellia fusca
| style="text-align: center;" | proline-containing cyclopeptide[{{cite journal |vauthors=Zhang HJ, Yi YH, Yang GJ, Hu MY, Cao GD, Yang F, etal | title=Proline-containing cyclopeptides from the marine sponge Phakellia fusca. | journal=J Nat Prod | year= 2010 | volume= 73 | issue= 4 | pages= 650–5 | pmid=20345147 | doi=10.1021/np9008267 | url=https://pubmed.ncbi.nlm.nih.gov/20345147 }}] |
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Hymenistatin
| Phakellia fusca
| style="text-align: center;" | bio-active proline-containing cyclopeptide |
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Hyrtinadine A
| Hyrtios
| style="text-align: center;" | bio-active bis-indole alkaloid |
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Manzamines
| various sponge species
| style="text-align: center;" | bio-active β-carbolines |
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Mirabamide
| Siliquariaspongia mirabilis
| style="text-align: center;" | antiviral depsipeptide |
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Neamphamide A
| Neamphius huxleyi
| style="text-align: center;" | antiviral depsipeptide |
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Onnamide A
|Theonella swinhoei
| style="text-align: center;" |cytotoxic, inhibits protein synthesis[{{cite journal |author1=Shigeki Matsunaga |author2=Nobuhiro Fusetani |author3=Youichi Nakao |year=1992 |title=Eight New Cytotoxic Metabolites Closely Related to Onnamide A from Two Marine Sponges of the Genus Theonella |journal=Tetrahedron |volume=48 |issue=39 |pages=8369–8376 |doi=10.1016/S0040-4020(01)86585-6}}] |
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Peloruside A
| Mycale sp. (New Zealand)
| style="text-align: center;" | cytotoxic / structurally similar to bryostatin |
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Phakellistatins
| Phakellia fusca
| style="text-align: center;" | proline-containing cyclopeptides |
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Phoriospongin
| Phoriospongia and Callyspongia bilamellata
| style="text-align: center;" | nematocidal compound |
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Plakevulin A
| Plakortis
| style="text-align: center;" | DNA polymerase inhibitor |
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Plakoridine A
| Plakortis
| style="text-align: center;" | |
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Polydiscamide B
| Ircinia
| style="text-align: center;" | the first example of a nonendogenous human SNSR (human sensory neuron-specific G protein couple receptor) agonist[{{cite journal|vauthors=Feng Y, Carroll AR, Pass DM, Archbold JK, Avery VM, Quinn RJ | title=Polydiscamides B-D from a marine sponge Ircinia sp. as potent human sensory neuron-specific G protein coupled receptor agonists. | journal=J Nat Prod | year= 2008 | volume= 71 | issue= 1 | pages= 8–11 | pmid=18163586 | doi=10.1021/np070094r | url=https://pubmed.ncbi.nlm.nih.gov/18163586 }}] |
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Ptilomycalin A
| Monanchora arbuscula
| style="text-align: center;" | antifungal spirocyclic guanidine alkaloid / laccase and melanization inhibitor |
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Sceptrin
|Agelas conifera
| style="text-align: center;" |Antibiotic[{{cite journal |last1=Rodriguez |first1=AD |last2=Lear |first2=MJ |last3=La Clair |first3=JJ |year=2008 |title=Identification of the binding of sceptrin to MreB via a bidirectional affinity protocol |journal=J Am Chem Soc |volume=130 |issue=23 |pages=7256–7258 |doi=10.1021/ja7114019 |pmid=18479102}}] |
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Suberedamine
|Suberea
| |
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Theonellamide F
| Theonella
| style="text-align: center;" | antimicrobial/antifungal cytotoxic bicyclic dodecapeptide[{{cite journal |vauthors=Otero-González AJ, Magalhães BS, Garcia-Villarino M, López-Abarrategui C, Sousa DA, Dias SC, etal | title=Antimicrobial peptides from marine invertebrates as a new frontier for microbial infection control. | journal=FASEB J | year= 2010 | volume= 24 | issue= 5 | pages= 1320–34 | pmid=20065108 | doi=10.1096/fj.09-143388 | doi-access=free }}][{{cite journal |vauthors=Espiritu RA, Matsumori N, Murata M, Nishimura S, Kakeya H, Matsunaga S, etal | title=Interaction between the marine sponge cyclic peptide theonellamide A and sterols in lipid bilayers as viewed by surface plasmon resonance and solid-state (2)H nuclear magnetic resonance. | journal=Biochemistry | year= 2013 | volume= 52 | issue= 14 | pages= 2410–8 | pmid=23477347 | doi=10.1021/bi4000854 | url=https://pubmed.ncbi.nlm.nih.gov/23477347 }}] |
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Topsentolides
| Topsentia
| style="text-align: center;" | cytotoxic oxylipins[{{cite journal |vauthors=Luo X, Li F, Hong J, Lee CO, Sim CJ, Im KS, etal | title=Cytotoxic oxylipins from a marine sponge Topsentia sp. | journal=J Nat Prod | year= 2006 | volume= 69 | issue= 4 | pages= 567–71 | pmid=16643027 | doi=10.1021/np0503552 | url=https://pubmed.ncbi.nlm.nih.gov/16643027 }}] |
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Xestoquinone
|Xestospongia
| style="text-align: center;" |Antimalarial,[{{cite journal |last1=Laurent |first1=Dominique |last2=Jullian |first2=Valérie |last3=Parenty |first3=Arnaud |last4=Knibiehler |first4=Martine |last5=Dorin |first5=Dominique |last6=Schmitt |first6=Sophie |last7=Lozach |first7=Olivier |last8=Lebouvier |first8=Nicolas |last9=Frostin |first9=Maryvonne |last10=Alby |first10=Frédéric |last11=Maurel |first11=Séverine |date=1 July 2006 |title=Antimalarial potential of xestoquinone, a protein kinase inhibitor isolated from a Vanuatu marine sponge Xestospongia sp |url=https://www.ncbi.nlm.nih.gov/pubmed/16513357 |journal=Bioorganic & Medicinal Chemistry |volume=14 |issue=13 |pages=4477–4482 |doi=10.1016/j.bmc.2006.02.026 |issn=0968-0896 |pmid=16513357 |last14=Sauvain |first14=Michel |first13=Laurent |last13=Meijer |first12=Christian |last12=Doerig}}] antifungal, and cytotoxic[{{cite journal |last1=Nakamura |first1=Mitsuhiro |last2=Kakuda |first2=Takahiko |last3=Qi |first3=Jianhua |last4=Hirata |first4=Masayuki |last5=Shintani |first5=Tomoaki |last6=Yoshioka |first6=Yukio |last7=Okamoto |first7=Tetsuji |last8=Oba |first8=Yuichi |last9=Nakamura |first9=Hideshi |last10=Ojika |first10=Makoto |date=September 2005 |title=Novel relationship between the antifungal activity and cytotoxicity of marine-derived metabolite xestoquinone and its family |journal=Bioscience, Biotechnology, and Biochemistry |volume=69 |issue=9 |pages=1749–1752 |doi=10.1271/bbb.69.1749 |issn=0916-8451 |pmid=16195594 |s2cid=11599803|doi-access=free }}] |
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Semisynthetic analogs of the sponge isolate jasplakinolide, were submitted to National Cancer Institute’s Biological Evaluation Committee in 2011.