Sponge isolates

Halichondria produces the eribulin (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).

Isolate Source Researched activity / Chemical description
Aciculitin Aciculites ciliate antifungal cyclic peptide
Discodermin Discodermia kiiensis antimicrobial tetradecapeptide
Halichondrin B Halichondria okadai Kadota (Miura Peninsula) precursor to eribulin (Halaven)[1]
Halicylindramide Halichondria antifungal peptide
Hymenamides Phakellia fusca proline-containing cyclopeptide[2]
Hymenistatin Phakellia fusca bio-active proline-containing cyclopeptide
Hyrtinadine A Hyrtios bio-active bis-indole alkaloid
Manzamines various sponge species bio-active β-carbolines
Mirabamide Siliquariaspongia mirabilis antiviral depsipeptide
Neamphamide A Neamphius huxleyi antiviral depsipeptide
Peloruside A Mycale sp. (New Zealand) cytotoxic / structurally similar to bryostatin
Phakellistatins Phakellia fusca proline-containing cyclopeptides[2]
Phoriospongin Phoriospongia and Callyspongia bilamellata nematocidal compound
Plakevulin A Plakortis DNA polymerase inhibitor
Plakoridine A Plakortis
Polydiscamide B Ircinia the first example of a nonendogenous human SNSR (human sensory neuron-specific G protein couple receptor) agonist[3]
Ptilomycalin A Monanchora arbuscula antifungal spirocyclic guanidine alkaloid / laccase and melanization inhibitor
Theonellamide F Theonella antimicrobial/antifungal cytotoxic bicyclic dodecapeptide[4][5]
Topsentolides Topsentia cytotoxic oxylipins[6]

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

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

References

  1. ↑ Towle MJ, Salvato KA, Budrow J, Wels BF, Kuznetsov G, Aalfs KK, et al. (2001). "In vitro and in vivo anticancer activities of synthetic macrocyclic ketone analogues of halichondrin B.". Cancer Res. 61 (3): 1013–21. PMID 11221827.
  2. 1 2 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. PMID 20345147. doi:10.1021/np9008267.
  3. ↑ 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. PMID 18163586. doi:10.1021/np070094r.
  4. ↑ 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. PMID 20065108. doi:10.1096/fj.09-143388.
  5. ↑ 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. PMID 23477347. doi:10.1021/bi4000854.
  6. ↑ Luo X, Li F, Hong J, Lee CO, Sim CJ, Im KS, et al. (2006). "Cytotoxic oxylipins from a marine sponge Topsentia sp.". J Nat Prod. 69 (4): 567–71. PMID 16643027. doi:10.1021/np0503552.
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