Bioactive Compounds from Sponges (Phylum Porifera) Diversity of Sponge-Derived Compounds Manoalide: A Phospholipase A2 Inhibitor Bioactive Compounds from Cnidarians Introduction to the Cnidaria Pseudoptersin: An Inhibitor of Eicosanoid Releas Overview
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Bioactive Compounds from Sponges (Phylum Porifera) Diversity of Sponge-Derived Compounds Manoalide: A Phospholipase A2 Inhibitor Bioactive Compounds from.
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Bioactive Compounds from Sponges (Phylum Porifera)
Diversity of Sponge-Derived Compounds
Manoalide: A Phospholipase A2 Inhibitor
Bioactive Compounds from Cnidarians
Introduction to the Cnidaria
Pseudoptersin: An Inhibitor of Eicosanoid Release
Overview
OO
OH
HO
OH O NH2
O
Discodermolide
Inhibits cell-division by stabilizing microtubules (i.e. inhibiting depolymerization)
Anticancer drug (Clinical Phase II)
Discodermia dissolute
Drugs from the Sea: SpongesDrugs from the Sea: Sponges
Okadaic Acid
OA inhibits PP1 and PP2A sub-type of Ser/Thr Protein Phosphatases
Biomedical Research Tool
Halichondria okadai
HO
O
O O
O
O O
O
O
CH3
CH3H
CH3
H
HOH
OH
H
OH
H3C OH
H3C
HO
O
HO
HO
OO
O
O
O
O
O
OO
O
O
O
OOO
H
H
H
H
H
H
H
H
Halichondrin B
Drugs from the Sea: SpongesDrugs from the Sea: Sponges
Other Bioactive Compounds from Other Bioactive Compounds from Marine SpongesMarine Sponges
More than 5,300 sponge derived compounds (2000)
…hundreds more discovered each year.
Other Bioactive Compounds from Other Bioactive Compounds from Marine SpongesMarine Sponges
Azothymidine (AZT), or Zidovudine
Retrovir®Cytosine
Arabinoside(Ara-C)
O
N
HN
O
OH
O
R
HO
OH
Arabinose
O
N
N
O
OH
NH2
HO
OH
R = CH3, SpongothymidineR = H, Spongouracil
(from Cryptotethya crypta)
O
N
HN
O
N
O
CH3
HO
N+
N-
Other Bioactive Compounds from Other Bioactive Compounds from Marine Sponges: Marine Sponges: AntiviralAntiviral
Antiviral Compounds from Sponges
Compound Class ActivityDragmacidin F Indole Alkaloid AntiviralPapuamides C, D Cyclic Peptides HIV-1Mololipids Tyramine Lipids HIV-1Haplosamates A, B Sulfamated Steroid HIV-1 Integrase InhibitorHamigeran B Phenolic Macrolide Antiviral - Herpes, PolioWeinbersterols A, B Sulfated Sterols Antiviral - Feline LeukemiaVariolin B Alkaloid AntiviralAvarol Hydroquinone/ UAG Suppressor
Other Bioactive Compounds from Other Bioactive Compounds from Marine Sponges: Marine Sponges: AntimicrobialAntimicrobial
Compound Class ActivityDiscodermins B, C, D Cyclic Peptide AntibacterialTopsentiasterolSulfates Sulfated Sterol Antibacterial/AntifungalArenosclerins A, B , C Alkylpiperidine AntibacterialAxinellamines B-D Imidazo-azolo- Antibacterial
-imidazole alkaloidAcanthosterol I and J Sulfated Sterol AntifungalOceanapiside Biasminohydroxylipid Antifungal
LactoneLeucascandrolide A Oxazole-Containing Antifungal
Polyether Macrolide
Other Bioactive Compounds from Other Bioactive Compounds from Marine Sponges: Marine Sponges: “Antifouling”“Antifouling”
Compound ClassKalihinene X IsocyanoterpenoidKalihipyran B Isocyanoterpenoid10 -Formarnidokalihinol IsocyanoterpenoidPseudoeratidine 2 Dibromopyrrole-Containing
Spermidine DerivativeCeratinamide A and B Bromotyrosine DerivativeC22 Ceramide CeramideFormoside Triterpene Glycoside,
Look, Fenical, Jacobs and Clardy (1986) Proc. Natl. Acad. Sci., 83: 6238-40
O
OH
OOH
HO
HO
Pseudopterosin A
Pseudopterosin A Inhibits Inflammation Pseudopterosin A Inhibits Inflammation Response in Mouse ModelResponse in Mouse Model
Look, Fenical, Jacobs and Clardy (1986) Proc. Natl. Acad. Sci., 83: 6238-40
OH
O
O
OH
OH
OH
O
OH
O
OH
HO
HO
Pseudopterosin A
Pseudopterosin E
Pseudopterosin A and E (PsA and PsE): Pseudopterosin A and E (PsA and PsE): Antiinflammatory Mechanism(s)Antiinflammatory Mechanism(s)
Mayer et al. (1998) Life Sci., 62: 401-407
PsA and PsE Inhibit Mouse Ear EdemaPsA and PsE Inhibit Mouse Ear Edema
Mayer et al. (1998) Life Sci., 62: 401-407
PsA and PsE Inhibit PBQ- and Zymosan-PsA and PsE Inhibit PBQ- and Zymosan-Induced WrithingInduced Writhing
Mayer et al. (1998) Life Sci., 62: 401-407
PsE Inhibits Zymosan-Induced Peritoneal PsE Inhibits Zymosan-Induced Peritoneal Prostaglandin and Leukotriene ExudateProstaglandin and Leukotriene Exudate
Mayer et al. (1998) Life Sci., 62: 401-407
PsA and PsE Inhibit Zymosan-Induced PsA and PsE Inhibit Zymosan-Induced Release of Prostaglandin and Release of Prostaglandin and
Leukotriene from Murine Peritoneal Leukotriene from Murine Peritoneal MacrophagesMacrophages
Mayer et al. (1998) Life Sci., 62: 401-407
Commerical Potential of PseudopterosinsCommerical Potential of Pseudopterosins
Licensed to OsteoArthritis Sciences, Inc.
Synthetic Derivative (Methopterosin)Completed Pre-Clinical Trials; Expected to
Enter Phase-1 Clinical Trials as Topical Anti-Inflammatory for Dermatitis