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Vasicine glycoside hydrolysis?

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Elrik

Elrik

Rising Star
Has anyone any idea what pH and cooking time would be effective for the hydrolysis of vasicine glycoside?

With more pandemic on the horizon and 2,5 kilos of syrian rue in my basement I decided to isolate some vasicine as a potential bronchodilator [not to mention a parasiticide etc.].
I made tea from 250g rue, got it clear, based it, centrifuged an aliquot and confirmed that more base was not needed, isolated the solids, dissolved them in 1M acetic acid, centrifuged the crud out, mansked out the harmalas, based the supernatant, and... got a far lower yield than I should have.
Investigations of the literature showed that most of the vasicine in mature esfand is in the form of vasicine-O-glucopyranosylglucopyranoside. An alkaloid saponin. This could explain the persistent foamyness of the working solutions and the persistent milkiness that couldnt be centrifuged out.
I was always struck by Manskes use of a blatant, almost absurd excess of acetic acid in his original rue extraction method. Could this be to effect an acid hydrolysis of the alkaloid glycoside? I suspect so.

I am repeating the last test extraction but this time I will drop the pH much lower after clarifying the tea and then I'll cook the acid tea for some hours. I'm curious if anyone has tried something similar?
 
And it smells quite nice, like some sort of middle eastern spiced coffee.

I'm just hoping to make a MAOI-free 'breathe-easier' pill that could be easily used while sick and would last several hours.
If I get sick I'll be doing everything for myself or I'll be in the hospital, nothing between.
 
To me it seems smarter to focus on preventing an infection from getting serious, and whole extract rue is highly likely to be an effective agent for protecting from and/or clearing out covid-19 infection. I have personal experience healing my own covid-19 infection, aside from the research.
 
Ah, but unless it were tea a whole rue extract would be missing the majority of vasicine if that alkaloid were locked up as the glycoside. Even the tea would be missing the influence of that component if hydrolysis does not occur in the gut.

And, in any event, I like making pure things :p
 
It makes me wonder whether cellulase would have any activity in breaking down the glucosylglucoside to at least the simple glycoside. It would depend on the epimeric and isomeric form of the glucose-glucose bond (i.e. α or β, and 1→4 or 1→6 or whatever).
 
Before going to that level I think I'll just stick to acid hydrolysis for my initial attempt :lol:

I've decided to try pH < 3 for 3 hours at 80°C. Possibly with a few hours of decanting and filtering at pH < 3 if it makes crud precipitate. This should roughly replicate maskes several hours of simmering with strong vinegar water without risk to my better large stainless steel pot.

I've always felt strange about throwing away vasicine. It must have a use.
 
One particular "use" of vasicine is for allowing people to get it confused with viscine, thereby providing a strange etymological path between syrian rue and mistletoe - dithyramb? :lol:

We should look out for other nomenclatural coincidences. Now, if you'll allow me to conclude the tangent, I find it amazing, still, that phosphorus - the bearer of light - is essential as the energy carrier for ALL lifeforms on this planet, in the form of ATP. They did not know this at the time that it gained its name. And this, somehow, ties in with the recent harmala phosphate question. Maybe :?


Given that, for example, some cationic surfactants are potent biocides it seems to me to be likely that vasicine glycoside could afford some biocidal properties to harmel extracts.
 
Very interesting, Elrik!

I did some experiments with fermenting harmala tea. Actually those experiments are not yet concluded and have the potential to go much further (at least in my mind).

The point being that fungal (example: yeast) or bacterial (example: lactic acid bacteria) fermentation could also be the answer to your quest of freeing up the vasicine compound to make it bioavailable.
These microbes secrete various enzymes into their environment, therefore the reasoning is that it is possible to achieve this with enzymatic reactions.

I should point out that I am no expert in chemistry and only have a limited understanding on the various processes that are studied. Also I just learned this a new - previously I thought that vasicine is totally available and just floating around in the tea.

Links to harmala and fly agaric fermentation.
 
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