Sponge isolates

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

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}}

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}}

Aplyzanzine A

|Aplysina sp.

|

Avarol

|Dysidea avara

| style="text-align: center;" |antitumor, antimicrobialAsian Journal of Chemistry; Vol. 26, No. 23 (2014), 8255-8256 and antiviralSagar, S.; Kaur, M.; Minneman, K. P. Antiviral Lead Compounds from Marine Sponges. Marine Drugs 2010, 8 (10), 2619–2638 effects

Aciculitin

| Aciculites ciliate

| style="text-align: center;" | antifungal cyclic peptide

Discodermin

| Discodermia kiiensis

| style="text-align: center;" | antimicrobial tetradecapeptide

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}}

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 }}

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}}

Halicylindramide

| Halichondria

| style="text-align: center;" | antifungal peptide

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 }}

Hymenistatin

| Phakellia fusca

| style="text-align: center;" | bio-active proline-containing cyclopeptide

Hyrtinadine A

| Hyrtios

| style="text-align: center;" | bio-active bis-indole alkaloid

Manzamines

| various sponge species

| style="text-align: center;" | bio-active β-carbolines

Mirabamide

| Siliquariaspongia mirabilis

| style="text-align: center;" | antiviral depsipeptide

Neamphamide A

| Neamphius huxleyi

| style="text-align: center;" | antiviral depsipeptide

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}}

Peloruside A

| Mycale sp. (New Zealand)

| style="text-align: center;" | cytotoxic / structurally similar to bryostatin

Phakellistatins

| Phakellia fusca

| style="text-align: center;" | proline-containing cyclopeptides

Phoriospongin

| Phoriospongia and Callyspongia bilamellata

| style="text-align: center;" | nematocidal compound

Plakevulin A

| Plakortis

| style="text-align: center;" | DNA polymerase inhibitor

Plakoridine A

| Plakortis

| style="text-align: center;" |

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 }}

Ptilomycalin A

| Monanchora arbuscula

| style="text-align: center;" | antifungal spirocyclic guanidine alkaloid / laccase and melanization inhibitor

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}}

Suberedamine

|Suberea

|

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 }}

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 }}

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 }}

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