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Sponge isolates

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).

IsolateSourceResearched activity / Chemical description
3-Alkylpyridinium (3-AP)Haploscleridahemolytic and cytotoxic
Agosterol Aanticancer
Aplyzanzine AAplysina sp.
AvarolDysidea avaraantitumor, antimicrobial and antiviral effects
AciculitinAciculites ciliateantifungal cyclic peptide
DiscoderminDiscodermia kiiensisantimicrobial tetradecapeptide
DysideninLamellodysidea herbaceaHighly toxic
GirollineGirollineinhibits protein synthesis
Halichondrin BHalichondria okadai Kadota (Miura Peninsula)precursor to eribulin (Halaven)[1]
HalicylindramideHalichondriaantifungal peptide
HymenamidesPhakellia fuscaproline-containing cyclopeptide
HymenistatinPhakellia fuscabio-active proline-containing cyclopeptide
Hyrtinadine AHyrtiosbio-active bis-indole alkaloid
Manzaminesvarious sponge speciesbio-active β-carbolines
MirabamideSiliquariaspongia mirabilisantiviral depsipeptide
Neamphamide ANeamphius huxleyiantiviral depsipeptide
Onnamide ATheonella swinhoeicytotoxic, inhibits protein synthesis
Peloruside AMycale sp. (New Zealand)cytotoxic / structurally similar to bryostatin
PhakellistatinsPhakellia fuscaproline-containing cyclopeptides
PhoriosponginPhoriospongia and Callyspongia bilamellatanematocidal compound
Plakevulin APlakortisDNA polymerase inhibitor
Plakoridine APlakortis
Polydiscamide BIrciniathe first example of a nonendogenous human SNSR (human sensory neuron-specific G protein couple receptor) agonist
Ptilomycalin AMonanchora arbusculaantifungal spirocyclic guanidine alkaloid / laccase and melanization inhibitor
SceptrinAgelas coniferaAntibiotic
SuberedamineSuberea
Theonellamide FTheonellaantimicrobial/antifungal cytotoxic bicyclic dodecapeptide
TopsentolidesTopsentiacytotoxic oxylipins
XestoquinoneXestospongiaAntimalarial, antifungal, and cytotoxic

Semisynthetic analogs of the sponge isolate jasplakinolide, were submitted to National Cancer Institute’s Biological Evaluation Committee in 2011.

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Other marine isolates

Trabectedin, aplidine, didemnin, were isolated from sea squirts. Monomethyl auristatin E is a derivative of a dolastatin 10, a compound made by Dolabella auricularia. Bryostatins were first isolated from Bryozoa.

Salinosporamides are derived from Salinispora tropica. Ziconotide is derived from the sea snail Conus magus.

See also

  • Marine life portal

References

  1. SepčIć, Kristina; Guella, Graziano; Mancini, Ines; Pietra, Francesco; Serra, Mauro Dalla; Menestrina, Gianfranco; Tubbs, Kemmons; MačEk, Peter; Turk, Tom (1997). "Characterization of Anticholinesterase-Active 3-Alkylpyridinium Polymers from the Marine Sponge Reniera saraiin Aqueous Solutions". Journal of Natural Products. 60 (10): 991–996. doi:10.1021/np970292q. PMID 9358641. /wiki/Doi_(identifier) ↩

  2. Chen, Zhe-Sheng; Aoki, Shunji; Komatsu, Masaharu; Ueda, Kazumitsu; Sumizawa, Tomoyuki; Furukawa, Tatsuhiko; Okumura, Hiroshi; Ren, Xiao-Qin; Belinsky, Martin G.; Lee, Kun; Kruh, Gary D.; Kobayashi, Motomasa; Akiyama, Shin-ichi (2001). "Reversal of drug resistance mediated by multidrug resistance protein (MRP) 1 by dual effects of agosterol a on MRP1 function". International Journal of Cancer. 93 (1): 107–113. doi:10.1002/ijc.1290. ISSN 0020-7136. PMID 11391629. https://doi.org/10.1002%2Fijc.1290 ↩

  3. Aoki, Shunji; Chen, Zhe-Sheng; Higasiyama, Kimihiko; Setiawan, I; Akiyama, Shin-ichi; Kobayashi, Motomasa (2001). "Reversing Effect of Agosterol A, a Spongean Sterol Acetate, on Multidrug Resistance in Human Carcinoma Cells". Japanese Journal of Cancer Research. 92 (8): 886–895. doi:10.1111/j.1349-7006.2001.tb01177.x. ISSN 0910-5050. PMC 5926837. PMID 11509122. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5926837 ↩

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  6. Van Sande, J; Deneubourg, F; Beauwens, R; Braekman, JC; Daloze, D; Dumont, JE (April 1990). "Inhibition of iodide transport in thyroid cells by dysidenin, a marine toxin, and some of its analogs". Molecular Pharmacology. 37 (4): 583–9. PMID 2157965. /wiki/PMID_(identifier) ↩

  7. Kottakota, SK; Evangelopoulos, D; Alnimr, A; Bhakta, S; McHugh, TD; Gray, M; Groundwater, PW; Marrs, EC; Perry, JD; Spilling, CD; Harburn, JJ (2012). "Synthesis and biological evaluation of purpurealidin E-derived marine sponge metabolites: aplysamine-2, aplyzanzine A, and suberedamines A and B". J Nat Prod. 75 (6): 1090–101. doi:10.1021/np300102z. PMID 22620987. /wiki/Doi_(identifier) ↩

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  9. Zhang HJ, Yi YH, Yang GJ, Hu MY, Cao GD, Yang F, et al. (2010). "Proline-containing cyclopeptides from the marine sponge Phakellia fusca". J Nat Prod. 73 (4): 650–5. doi:10.1021/np9008267. PMID 20345147. https://pubmed.ncbi.nlm.nih.gov/20345147 ↩

  10. Shigeki Matsunaga; Nobuhiro Fusetani; Youichi Nakao (1992). "Eight New Cytotoxic Metabolites Closely Related to Onnamide A from Two Marine Sponges of the Genus Theonella". Tetrahedron. 48 (39): 8369–8376. doi:10.1016/S0040-4020(01)86585-6. /wiki/Doi_(identifier) ↩

  11. Zhang HJ, Yi YH, Yang GJ, Hu MY, Cao GD, Yang F, et al. (2010). "Proline-containing cyclopeptides from the marine sponge Phakellia fusca". J Nat Prod. 73 (4): 650–5. doi:10.1021/np9008267. PMID 20345147. https://pubmed.ncbi.nlm.nih.gov/20345147 ↩

  12. Feng Y, Carroll AR, Pass DM, Archbold JK, Avery VM, Quinn RJ (2008). "Polydiscamides B-D from a marine sponge Ircinia sp. as potent human sensory neuron-specific G protein coupled receptor agonists". J Nat Prod. 71 (1): 8–11. doi:10.1021/np070094r. PMID 18163586. https://pubmed.ncbi.nlm.nih.gov/18163586 ↩

  13. Rodriguez, AD; Lear, MJ; La Clair, JJ (2008). "Identification of the binding of sceptrin to MreB via a bidirectional affinity protocol". J Am Chem Soc. 130 (23): 7256–7258. doi:10.1021/ja7114019. PMID 18479102. /wiki/Doi_(identifier) ↩

  14. Otero-González AJ, Magalhães BS, Garcia-Villarino M, López-Abarrategui C, Sousa DA, Dias SC, et al. (2010). "Antimicrobial peptides from marine invertebrates as a new frontier for microbial infection control". FASEB J. 24 (5): 1320–34. doi:10.1096/fj.09-143388. PMID 20065108. https://doi.org/10.1096%2Ffj.09-143388 ↩

  15. Espiritu RA, Matsumori N, Murata M, Nishimura S, Kakeya H, Matsunaga S, et al. (2013). "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". Biochemistry. 52 (14): 2410–8. doi:10.1021/bi4000854. PMID 23477347. https://pubmed.ncbi.nlm.nih.gov/23477347 ↩

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  17. Laurent, Dominique; Jullian, Valérie; Parenty, Arnaud; Knibiehler, Martine; Dorin, Dominique; Schmitt, Sophie; Lozach, Olivier; Lebouvier, Nicolas; Frostin, Maryvonne; Alby, Frédéric; Maurel, Séverine; Doerig, Christian; Meijer, Laurent; Sauvain, Michel (1 July 2006). "Antimalarial potential of xestoquinone, a protein kinase inhibitor isolated from a Vanuatu marine sponge Xestospongia sp". Bioorganic & Medicinal Chemistry. 14 (13): 4477–4482. doi:10.1016/j.bmc.2006.02.026. ISSN 0968-0896. PMID 16513357. https://www.ncbi.nlm.nih.gov/pubmed/16513357 ↩

  18. Nakamura, Mitsuhiro; Kakuda, Takahiko; Qi, Jianhua; Hirata, Masayuki; Shintani, Tomoaki; Yoshioka, Yukio; Okamoto, Tetsuji; Oba, Yuichi; Nakamura, Hideshi; Ojika, Makoto (September 2005). "Novel relationship between the antifungal activity and cytotoxicity of marine-derived metabolite xestoquinone and its family". Bioscience, Biotechnology, and Biochemistry. 69 (9): 1749–1752. doi:10.1271/bbb.69.1749. ISSN 0916-8451. PMID 16195594. S2CID 11599803. https://doi.org/10.1271%2Fbbb.69.1749 ↩