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Marine Indole Alkaloids

Migrated topic.


Rising Star

Lot of interesting indole alkaloids here, some tryptamines, found in marine algaes and sponges.

For instance:
Examination of the organic extract of the broth of an unidentified algicolous fungus collected from the surface of the marine red alga Gracilaria verrucosa led to the isolation of Nb-acetyltryptamine
Psychedelic tryptamine?

You can get this algae powdered on eBay under the listing title:
Aga Agar powder HOANG YEN - Gracilaria Verrucosa - Nutrient Agar
sold as a food ingredient.

Listing says "it's very suitable for people who are losing weight". 5-HTP (5-hydroxytryptamine) is an appetite suppressant. Nb-acetyltryptamine than could be responsible for their claimed weight-loss, suggesting perhaps their is active levels in the algae.


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ABSTRACT: Marine fungi are known to produce structurally unique secondary metabolites, and more than 1000 marine fungal-derived metabolites have already been reported. Despite the absence of marine fungal-derived metabolites in the current clinical pipeline, dozens of them have been classified as potential chemotherapy candidates because of their anticancer activity. Over the last decade, several comprehensive reviews have covered the potential anticancer activity of marine fungal-derived metabolites. However, these reviews consider the term “cytotoxicity” to be synonymous with “anticancer agent”, which is not actually true. Indeed, a cytotoxic compound is by definition a poisonous compound. To become a potential anticancer agent, a cytotoxic compound must at least display (i) selectivity between normal and cancer cells (ii) activity against multidrug-resistant (MDR) cancer cells; and (iii) a preferentially non-apoptotic cell death mechanism, as it is now well known that a high proportion of cancer cells that resist chemotherapy are in fact apoptosis-resistant cancer cells against which pro-apoptotic drugs have more than limited efficacy. The present review thus focuses on the cytotoxic marine fungal-derived metabolites whose ability to kill cancer cells has been reported in the literature. Particular attention is paid to the compounds that kill cancer cells through non-apoptotic cell death mechanisms.

Did you see this!
Ergosinine (490), which was isolated from the marine mollusc Pleurobranchus forskalii, is the first ergot peptide alkaloid (ergopeptine) found in marine life. The authors propose that ergot alkaloids may play a defensive or protective role in mollusks and other marine organisms

Among the prenylated indole alkaloids, ergot alkaloids are a well-established group of natural products, known for their potent and manifold biological activities. Ergot alkaloids have been isolated from terrestrial sources exclusively until Pibocin A (483), the first representative of marine ergoline alkaloids, was obtained from extracts of the Far-Eastern ascidian Eudistoma sp. (Figure 78 ) [205]. Pibocins A (483) and B (484) [206] were found to show antimicrobial and cytotoxic effects against mouse Ehrlich carcinoma cells [205,206]. 2-(3,3-Dimethylprop-1-ene)-costaclavine (485) and 2-(3,3-dimethylprop-1-ene)-epi-costaclavine (486) were isolated from the marine-derived fungus Aspergillus fumigatus, together with known clavine-type alkaloids costaclavine (487) and fumigaclavines A (488 ) [207] and C (489) [208]. Except of fumigaclavine A, all of them were found to show weak cytotoxicity against the mouse leukemia cell line P388 [209]. Additionally, fumigaclavine C (489) was found to induce apoptosis in MCF-7 breast cancer cells [210]. Ergosinine (490), which was isolated from the marine mollusc Pleurobranchus forskalii, is the first ergot peptide alkaloid (ergopeptine) found in marine life. The authors propose that ergot alkaloids may play a defensive or protective role in mollusks and other marine organisms

Ergot alkaloids in marine organisms, this is truly intriguing!

Other parts of that article were great as well,

The structure of 1,2-Di(1H-indol-3-yl)ethane particularly interested me, though not as a psychoactive...

The Indole-3-glyoxylates and indole-3-carboxylates were interesting as well...

I've only skimmed through for now, I'll have to post after I have really read the article.



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Wow! I wonder than if LSD has cytotoxic effects against cancer cell lines.
I've read that CBD is anti-cancer because the endocannabinoid system regulates cancer in the body. Perhaps the serotonin and dopamine systems have similar benefits.
Look at ergosinine in comparison to ergotamine...

Ergosinine may have similar medical applications to ergotamine tartrate (ET), The medical application of ET in regards to migraine are mediated by the compound's pharmacological action, which involves constriction of the intracranial extracerebral blood vessels (which is mediated tgrough the 5-HT1B receptor), it also employs anti-migraine effects by inhibiting trigeminal neurotransmission by 5-HT1D receptors.

I would be willing to bet that ergosinine could serve a similar role to ET in the manufacture of lysergic acid diethylamide, but I'll discuss that another time.

Below the potential pharmacological actions of Ergosine and ergosinine are discussed:
Ergosine and its D-isolysergic acid derivative ergosinine were investigated on canine saphenous veins both in vivo and in vitro. Following local i.v. infusion in vivo, about 5 times higher doses of ergosinine were necessary to produce the same venoconstrictor response as induced by ergosine. When administered orally, however, both ergot alkaloids were equi-effective. In vitro methiothepin, a 5-HT receptor blocker with high affinity for 5-HT1 receptors, antagonized venoconstrictor responses to 5-HT and ergosine within the same concentration range, being significantly less potent when tested against norepinephrine. The reverse was true for the α2-selective adrenoceptor blocker yohimbine, which was significantly more potent against norepinephrine and ergosine than against 5-HT, suggesting that ergosine has affinity to both 5-HT1-like receptors and α2-adrenoceptors. Concentration-response curves to norepinephrine were shifted to the right in a parallel fashion when ergosine or ergosinine were present in the organ baths, suggesting competitive antagonism. The blocking potency of ergosinine increased with increasing incubation times in Krebs-Henseleit solution becoming similar to that of ergosine when an incubation time of 2 hr was applied. It is suggested that the pharmacological activity of ergosinine is the consequence of an isomerization into its natural stereoisomer ergosine, which may occur both in vivo and in vitro.

PsilocybeChild said:

Wow! I wonder than if LSD has cytotoxic effects against cancer cell lines.
I've read that CBD is anti-cancer because the endocannabinoid system regulates cancer in the body. Perhaps the serotonin and dopamine systems have similar benefits.

Another possible mechanism has been raised by recent meta-analyses showing that serotonin signaling could prevent the type I IFN-mediated depressive behavior of HCV patients (86, 87). The signaling behind this phenomenon has not been uncovered yet; however, it is possible that chronic 5-HTR stimulation may block either the PRR-IRF3/7 or type I IFN receptor pathways. Since both NF-κB and type I IFN signaling contribute to the transcriptional regulation of genes that are involved in cellular proliferation and survival, and many psychedelics exhibit in vitro anti-cancer potential through 5-HTRs, these compounds could be promising candidates in novel therapies of cancer

DMT is likely the endogenous ligand for the sigma one receptor, as shown here

Harmala alkaloids, found in banisteriopsis caapi vine and peganum harmala seeds also show great potential for anti-cancer research:
Ethanol and chloroform extracts of P. harmala showed protective effects against thiourea-induced carcinogenicity by normalization of neuron-specific enolase and thyroglobulin levels in animal models.[64] Other effects of the plant extract such as anti-proliferative effect on Leukemic cell lines,[65] inhibitory action on the metastasis of melanoma cells, inducing apoptosis in melanoma cells,[66] tumor angiogenesis inhibition,[13] and binding to RNA[61] have also been reported by various authors. In some cases, P. harmala showed a higher selectivity towards malignant cells than common anticancer drugs like doxorubicin.[57] All of these data suggest that P. harmala and its alkaloids possess the potential to be used as novel antioxidant and anti-tumor agents in anti-cancer therapy.

Related to ayahuasca:
The possible anti-cancer activity of the decoction makes it a promising candidate for further researches in novel pharmacotherapies (Schenberg, 2013). Furthermore, DMT may also be an adaptogen increasing the survival rate of neurons or other cell types during acute hypoxia or under chronic oxidative stress.

These harmala alkaloids also have been shown to induce neurogenesis:

For a long time, a dogma has persisted that no new neurons are born in the brains of adults. Since the late 1990’s, this dated paradigm has been challenged by experimental evidence. The birth of new neurons, known as neurogenesis, occurs in two brain areas: around the ventricles and in a region of the hippocampus. The hippocampus plays a key role in important cognitive tasks such as learning and memory. Its function declines with the normal aging process, but does so much more dramatically in the presence of certain devastating neurodegenerative disorders such as Alzheimer’s disease and other dementias.

This is the first study ever conducted that demonstrates that components of the Ayahuasca brew have potent neurogenic properties.

However, all of this is fairly unrelated to marine indole alkaloids.

In This thread 2,4,6-tribromo-1,7-dimethoxy-N,N-dimethyltryptamine is looked into for anti-cancer potential.

...This post is getting "all over the place", this is a fairly large area of research that has spanned a good deal of time and several threads on this site, I apologize for the disorganization.


As for cannabinoids, while this is fascinating research, it's unrelated to indole marine alkaloids, (cannabinoids are actually unrelated to alkaloids all-together as they contain no nitrogen) I focus only on tryptamine and phenethylamine molecules, don't get me wrong, I stay currant with cannabinoid research, but ultimately it's a simple fascination rather than a serious research topic, but I figured I would provide some brief information regarding that area as well.

It is well-established that cannabinoids exert palliative effects on some cancer-associated symptoms. In addition evidences obtained during the last fifteen years support that these compounds can reduce tumor growth in animal models of cancer. Cannabinoids have been shown to activate an ER-stress related pathway that leads to the stimulation of autophagy-mediated cancer cell death. In addition, cannabinoids inhibit tumor angiogenesis and decrease cancer cell migration. The mechanisms of resistance to cannabinoid anticancer action as well as the possible strategies to develop cannabinoid-based combinational therapies to fight cancer have also started to be explored. In this review we will summarize these observations (that have already helped to set the bases for the development of the first clinical studies to investigate the potential clinical benefit of using cannabinoids in anticancer therapies) and will discuss the possible future avenues of research in this area.

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