Marine Alkaloids

Alkaloids built the chemical reputation of the sea long before the word “blue economy” existed. When manzamine A was pulled from an Okinawan sponge in 1986, its five interlocked rings told chemists that marine invertebrates were playing an entirely different structural game from land plants. Four decades on, the count of manzamine-family members alone has passed two hundred, and every major phylum in the reef — sponges, bryozoans, ascidians, molluscs, cyanobacteria — has contributed its own nitrogen-bearing architectures: β-carbolines, brominated indoles, pyrroloiminoquinones, pyrrole-2-carboxylates, macrolide-peptide hybrids.

Eata Marisource supplies this chemistry to the laboratories that study it. Our portfolio spans crude marine extracts for discovery screening, pre-fractionated libraries organised by chromatographic behaviour, and isolated alkaloids purified to analytical grade for use as reference standards, screening probes and starting points for synthetic programmes. Every lot ships with the spectral record a chemist needs to pick up exactly where the literature left off.

Where the nitrogen comes from: a source matrix

No single organism group owns marine alkaloid chemistry. Each source phylum tends to imprint its own structural signature, which is why sourcing strategy and chemistry strategy are the same conversation.

Dried filamentous marine cyanobacteria, one of the richest microbial sources of nitrogen-bearing secondary metabolites

Sponge alkaloids: the polycyclic heavyweights

Sponges dominate the marine alkaloid literature for good reason. The manzamine family — built around a β-carboline core fused to 6-, 8- and 13-membered rings — now numbers more than two hundred members isolated from over sixteen sponge species across five families. Fascaplysin, a planar 12H-pyrido[1,2-a:3,4-b′]diindole first obtained from a Fijian sponge, has accumulated its own synthetic literature of several decades, with kilogram-scalable routes published. Aaptamines (benzo[de][1,6]naphthyridines from Aaptos species) and the pyrroloiminoquinone makaluvamines round out the catalogue.

These molecules are produced by the organisms in vanishingly small quantities — the total yield of several celebrated manzamine total syntheses combined amounted to barely twelve milligrams before modern routes matured. That is precisely why a reliable extraction-and-fractionation partner matters: we supply the natural material where the biology lives, and purified isolates where the chemistry needs it.

• Manzamine-type alkaloids — β-carboline macrocyclics; available as hydrochloride salts on request.
• Fascaplysin — planar fused diindole; supplied as free base or salts for kinase-related screening.
• Aaptamines — naphthyridine alkaloids from Aaptos sponges, high-purity isolates.
• Pyrroloiminoquinones — makaluvamine and discorhabdin fractions from Latrunculia-type sponges.

Brominated indoles and pyrrole alkaloids

The North Sea bryozoan Flustra foliacea has yielded, since 1979, a running series of brominated and prenylated indole alkaloids — flustramines, deformylflustrabromines and 6-bromoindole-3-carbaldehyde among them — that have become standard tools in nicotinic acetylcholine receptor pharmacology and bacterial quorum-sensing research. On the pyrrole side, the lamellarin family (more than fifty members isolated from molluscs, tunicates and sponges since 1985) provides densely oxygenated 3,4-diarylpyrrole architectures, many reported as topoisomerase I and kinase inhibitors; several members circulate as water-soluble sulfate esters.

Both families illustrate what our customers usually need: not grams of a drug candidate, but milligrams of structurally faithful reference material, plus the neighbouring analogues that make structure–activity work possible. We organise supply around that reality.

Cyanobacterial alkaloids and alkaloidal peptides

Filamentous marine cyanobacteria — historically grouped as Lyngbya majuscula and now split across Moorena, Microcoleus and allied genera — manufacture an extraordinary range of amine-headed metabolites. The malyngamide family alone exceeds thirty members, all sharing a methoxylated fatty acid (lyngbic acid) condensed with a structurally variable amine head; their cyanobacterial origin is confirmed by the fact that sea hares carry them only through diet. Larger cyclic depsipeptides — apratoxins, lyngbyabellins, dolastatin-family peptides — blur the alkaloid/peptide boundary but are tracked by the same discovery pipelines.

We supply the dried biomass, the partitioned organic extracts and the chromatographic fractions, letting each laboratory decide where to place the purification cut.

Extraction and isolation: how we handle the material

Alkaloid work rewards patience at the front end. Our default workflow runs from freeze-dried biomass through sequential organic extraction, acid–base partitioning, and normal-phase or reversed-phase chromatography, with solvent removed under reduced pressure between stages. Basic fractions are tracked by thin-layer chromatography with colour reagents; purified isolates are confirmed by 1D/2D NMR and high-resolution mass spectrometry before release.

Continuous glass Soxhlet extraction, the workhorse first step for recovering alkaloid-rich lipophilic fractions from dried biomass

Open-column silica chromatography resolving a dark crude fraction into discrete coloured bands during alkaloid isolation

Partition chemistry is where crude extract becomes library. Alkaloids shift between aqueous and organic phases as a function of protonation state, so a short sequence of pH-stepped partitions can sort a gram of crude material into families that would otherwise overlap on every column. We run that sequence in-house and deliver the resulting fractions barcoded by phase, pH step and eluent.

Rotary evaporation under reduced pressure recovering solvent between extraction and chromatography stages

Purity verification and batch documentation

Reference chemistry lives and dies on documentation. Each purified lot is characterised before release, and the analytical package travels with the vial rather than on request.

A developed thin-layer chromatography plate showing separated sample spots, the fastest fingerprint check during fraction screening

Supply formats

Marine alkaloids reach customers in the physical form their downstream work dictates, from whole crude extracts to single compounds sealed under inert gas.

• Crude extracts — whole-organism or selective solvent extracts, shipped frozen or dried.
• Pre-fractionated libraries — plate-ready aliquots grouped by chromatographic behaviour.
• Purified isolates — milligram to multi-hundred-milligram quantities at ≥95% HPLC purity, with full spectral packages.
• Salts and derivatives — hydrochloride and other salt forms prepared for compounds that require stable crystalline handling.

Sealed amber glass ampoules of purified alkaloid solutions, the standard format for air-sensitive reference materials

Custom isolation and contract work

If the compound you need is not on the current list, the fastest route is a short conversation about source material and target structure. Our custom service covers organism sourcing and authentication, literature-directed isolation, analogue isolation around a lead scaffold, and scale-up of separation routes once a compound graduates from screening to process study. Tell us the molecule, the matrix it comes from, and the purity target — we will come back with a practical route and a transparent scope of work.

For Research or Industrial Raw Materials, Not For Personal Medical Use!