“Marine sponges are known to produce a variety of compounds with activity on the serotonin receptors 5-HT2A and 5-HT2c, similar to other psychedelics. Many of the compounds from the sea with this activity are tryptamines, like those from psychedelic plants and fungi, with a tendency to possess the element bromine.”
Biography
Zak grew up in Marin County, California with a passion for chemistry which blossomed through a course in medical ethnobotany at UC Berkeley and the friendship of Sasha and Ann Shulgin and others at the Friday Night Dinners. After his father passed away of cancer he took some time to reflect. With an invitation to study coral reef monitoring and seamanship aboard the RV Heraclitus in the South Pacific (Tokelau/Kiribati/Tuvalu/Fiji), his interest in neurochemistry progressed. Remembering an anticancer drug named halichondrin B from a marine sponge, he approached its discoverer, Yoshito Kishi, for advise about studying marine natural product chemistry in the South Pacific and was turned to Marine Natural Product Review, published by several chemists in New Zealand.
After finishing his undergraduate degree in Marine Toxicology on study abroad in Singapore, a New Zealand researcher steered him to work with Dutch sponge taxonomists in Indonesia. There he stayed for a total of 6 years, collecting marine sponges, taking extracts, and testing them for bioactivity. He managed a pearl farm in the most biodiverse dive spot on the planet and experimented with growing sponges. After developing a project with a chemistry lab in Bali, he accepted an offer from a PhD program in Okinawa, Japan where he performed more analytical chemistry and molecular biology techniques. He left the PhD program to work explicitly with a marine natural product chemist at another university and develop a sponge farming trial on a pearl farm in southern Okinawa. There he practiced feeding sponges chemicals to theoretically increase their production of psychoactive compounds and other medicinal alkaloids.
He is now working on returning to farm sponges on pearl farms across Indonesia to build chemical libraries and as part of an ecological restoration program. A questions he likes to ponder is what role neurotransmitters played before the evolution of neural consciousness..
Farming tryptamine medicines from marine sponges: yield enhancing lessons from directed biotransformation.
“Beyond psychedelic activity, many of these and similar compounds show anticancer and antiviral activity, clearly indicating the importance of the marine environment for creative solutions to human health.”
Transcript Abstract
In 1988 Jochen Gartz published research showing that the yield of the psychedelic psilocin from fruiting mycelia of Psilocybe cubensis increased from 0.01-0.15 % weight to up to 3.3% weight by exposing the mycelia to high concentrations of tryptamine, going on to show that the mycelia also convert added N,N-diethyl-tryptamine into additional psychedelics. This process, called biotransformation, was applied to marine sponges in an attempt to increase production of psychedelic and other compounds.
Marine sponges are known to produce a variety of compounds with activity on the serotonin receptors 5-HT2A and 5-HT2c, similar to other psychedelics. Many of the compounds from the sea with this activity are tryptamines, like those from psychedelic plants and fungi, with a tendency to possess the element bromine.
A variety of compounds, many of which are brominated, called aplysinopsins (named after the sponge Thorecta aplysinopsis) are produced by sponges such as Verongia spengelii, Dercitus, Hyrtios erecta, Smenospongia aurea, Thorectandra, Smenospongia and Verongula species. These compounds show various affinities for the serotonin receptors 5-HT2A and 5-HT2C, reflecting psychedelic activity.
The marine sponge Geodia barretti produces the brominated tryptamines barettin and 8,9-dihydrobarettin, which showed activity on serotonin receptors 5-HT2A and 5-HT2C, and only 5-HT2C receptor activity, respectively.
Alexander Shulgin wrote in Tryptamines I Have Known And Loved (TIHKAL) about many psychedelic tryptamines, including a variety containing the element bromine (5-Bromo-DMT, 5,6-dibromo-DMT, 5,6-dibromo-tryptamine, 5,6-dibromo-N-methyl-tryptamine) which were known to be produced by marine sponges (Smenospongia auria, S. echin, Polyfibrospongia maynardii). He went on to write “I had the fantasy of trying to scotch the rumor I’m about to start, that all the hippies of the San Francisco Bay Area were heading to the Caribbean with packets of Zig-Zag papers, to hit the sponge trade with a psychedelic fervor.”
Beyond psychedelic activity, many of these and similar compounds show anticancer and antiviral activity, clearly indicating the importance of the marine environment for creative solutions to human health.
Here, research is presented on biotransformations using marine sponges, tryptamine, and bromine. Owing to the fluorescent character of tryptamines, simple proof in the form of thin layer chromatography (TLC) clearly indicates some degree of biotransformation products. Cultivation and testing of 81 sponge samples on an Indonesian pearl farm and nearly 400 sponge cultures on a Japanese pearl farm are presented. This research precludes the current invitation to grow sponges for medicinal compounds on a dozen or more pearl farm sites in Indonesia.