Cardiovascular, antimicrobial, anti-inflammatory and antibiotic agents of marine origin

Content

• Cardiovascular, antimicrobial, anti-inflammatory and antibiotic agents of marine origin

Objective

At the end of this lecture, students will be able to:

• Discuss the different sources of Cardiovascular, antimicrobial, anti- inflammatory and antibiotic agents of marine origin

Marine Cardiovascular drugs

• Cardiotonics

• Marine peptides

• Marine glycosides

Laminin

• Obtained from marine algae Laminaria angustata

• Belongs  to  the  family  heterotrimeric  glycopoteins  composed  of heavy chain, designated as alpha and 2 light chains, designated as beta and gamma which are linked by disulphide bonds to form and symmetrical cross shaped structure

• Shows hypotensive effect

Octapamine

• Found in the salivary glands of Octapus vulgaris, O. macropus and Eledone moschata

• Produces cardiovascular adrenergic response

• As neurotransmitter in invertebrates

Saxitoxin (Mussel poison, Clam poison, Paralytic shellfish poison, STX)

• Obtained from the dinoflagellates, Gonyaulax catenella or G. tamarensis

• Exhibits hypotensive effect

Autonomium chloride

• Obtained from Verongia fistularis

• Exerts both α and β adrenergic effects

• Also exhibits cholinergic action

• Shows CNS stimulant activity

• Polypeptides obtained from marine sources (Sea anemones) includes a polypeptide with 147 aminoacids from Actinia equine exhibiting bradycardia, rapid hypotension and respiratory arrest

• Other polypeptides are obtained from Condylactis gigantean, Parasicyonis action stoloides exhibiting haemolytic and neurotoxic Action

Marine glycosdies – Holothurins and astrosaponins

Holothurins

• Obtained from the family, Holothuroidae and phylum Echinodermata possessing steroidal moiety resembling digitalis

Astrosaponins

• From fishes of family Asteroidae

Eledoisin

• Obtained from the posterior salivary glands of Eledone moschata

• Stimulates extravascular smooth muscle, lacrimal secretion

• Potent vasodilator, hypotensive agent

Hypotensive compounds

Spongosine

• Nucleoside and a methoxy derivative of adenosine

• Obtained from Caribbean sponge, Cryptotetheia crypta

• Exhibits various coronary vasodilation and negative inotropy

• Acts as hypotensive agent

• Reduces force and rate of contraction of heart

Doridosine

• Obtained from nudibranch Anisodoris nobilis

• Most potent hypotensive marine nucleoside

• Exerts hypothermic activity

Hypotensive peptides and other compounds

Aaptamine

• Obtained from Aaptos asptos

• Used as α adrenergic blocking agent

• Causes hypotension

Hymenin

• Obtained from Hymeniacidon aldis

• Used as α adrenergic blocking agent

• Causes hypotension

Urotensins I and II

• Obtained from specific caudal neurosecretory system of Giltichthys miralilis and from Catostomus commersoni

• Exerts vasodilation and hence hypotension

Antimicrobial agents

Chemical compound	Organism	Uses
Istamycins	Streptomyces tenimariensis	Effective against gram +ve and – ve organisms
Bromopyrones Fimbrolides Laurene	Ptilonia austrulasica Delisea fimbriata Laurencia	Have halogen in particular bromine, hence toxic
Holotoxin A, B, C (Steroidal glycoside)	Sea cucumber, Stichopus japonicas	Antifungal
Zonarol and isozonarol	Dictyopteris zonaroides (Brown algae)	Antimicrobial
Tetrabromoheptanone	Bonnemaisonia hemifera (Red algae)	Antimicrobial
Aeropolysnin	Verongia aerophola (Sponge)	Antimicrobial
Prepacifenol	Laurencia pacifia, L. filiformis (Red algae)	Antimicrobial
Thelphin	Thelepsus setosul (Annelida)	Antimicrobial
Eunicin	Eucinia mammosa (Gorgonian corals)	Antimicrobial
Acanthelin	Acanthella acuta	Against mycobacterium

Anti-inflammatory compounds

• A novel bi indoles was isolated from the marine cyanobacterium, Rivularia firma

• The major compound was (+)-7’-mtheoxy -2,3,5,5’ tetrabromo-3, 4’-bi-1H indole; Active against carrageenan & kaolin induced paw edema

• Palaulol, a sesqueterpene from the sponge, Fascaplysinopsis species

• A sesqueterpene furan form the coelenterate, Sinularia species

Other anti-inflammatory compound includes

• Dendalone-3-hydroxybutyrate from the sponge, Phyllospongia dendyi

• Flustramine A and B from the Swedish marine moss Flustra foliaceae

• Tetradotoxin form the globe fish Spheroides rubripes

• 6-n-tridecyl salicylic acid from the brown algae Caulocystis cephalornithos

• Flexibilide from the soft coral, Sinularia flexibilis

• Monalide from the sponge Luffariella variabilis

Antibiotic agents

The naturally occurring antibiotics includes

Okadaic acid (Halochondrine A)

• Obtained from Halichondria sps (Marine black sponge)

• First ionophoric polyether identified in marine organism

Acanthifolicin

• Obtained from the sponge, Pandoras acanthifolium

• Possess antibacterial activity and cytotoxic activity

The other antibiotic agents include

• 2,4 dibromo-6-(3,4,5  tribromo  pyrrole-2-yl)-phenol obtained from the Marine bacterium, Pseudomonas bromutilis

• Cycloeudesmol obtained from the red algae Chondria oppsiticlada

• Variablin and ircinin obtained from the sponge Ircinia strobilina & I. oros

• 3,5 dibromo 4 hydroxy benzene-1 acetamide obtained form the sponge, Verongia archeri

Summary

• Compounds used in cardiovascular system - laminin, octapamine, saxitoxin, autonomium chloride, astrosaponins, eledoisin, spongosine, doridosine, aaptamine, hymenin, urotensins etc

• Antimicorbial compounds - Istamycins, Bromopyrones, Fimbrolides, Laurene, Holotoxin A, B, C (Steroidal glycoside), Zonarol and isozonarol, Tetrabromoheptanone, Aeropolysnin, Prepacifenol, Thelphin, Eunicin, Acanthelin

• Anti-inflammatory drugs include novel bi indoles, (+)-7’-mtheoxy - 2,3,5,5’ tetrabromo-3, 4’-bi-1H indole etc

• The various antibiotics compounds are okadaic acid, acanthifolicin, 2,4  dibromo-6-(3,4,5  tribromo pyrrole-2-yl)-phenol, Cycloeudesmol, Variablin and ircinin, 3,5 dibromo 4 hydroxy benzene-1 acetamide etc