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Author: Subject: Please Assist the Noob... Attempting to extract compounds from Plants.
PickledPackratParalysis
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[*] posted on 11-6-2013 at 05:34
Please Assist the Noob... Attempting to extract compounds from Plants.


Hey guys,

I'm kind of new to chemistry, but I have been into wild edible plants for a while. I knew some poisonous plants that I wanted to test the toxicity of in a controlled experiment.

I grew some brine shrimp to use as 'lab rats', so hopefully they hatch this time! (they didn't last time, so that about sums up my ability to make a simple salt water solution!)

The first compound I wanted to extract was Solanine, and I have some plants it naturally occurs in, Horsenettle, Solanum carolinense, that I'm drying out to crush up in my mortar & pestle.

How would I get the Solanine out? I don't have the 'professional' solvents like Diethyl ether, but I was wondering what I would have to mix the crushed up plants with.

I have a centrifuge, some test tubes, two microscopes (my personal one is a Air Force surgical surplus one that has a max magnification of 75X... the other one goes to like 1500X and can see the cell organelles.) I was going to use the 75X one to watch what happens to the brine shrimp when I apply the Solanine to their petri dish.

What should I do to get the Solanine out? Are there other chemicals I have to make to use as solvents, catalysts, etc?

[Edited on 11-6-2013 by PickledPackratParalysis]
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[*] posted on 11-6-2013 at 05:37


acid base extraction might work for those

solvent could be toluene

[Edited on 11-6-2013 by Random]
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[*] posted on 11-6-2013 at 06:10


About the strongest acid I have is white vinegar, and the strongest base is household ammonia solution.

Is toluene something I could synthesize with household materials, or does it have to be bought at a chemical supplier?
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[*] posted on 11-6-2013 at 07:38


You need to first search for the literature examples of solanine isolation. But you might start with something easier, given that you don't have proper solvents, skills and equipment. Caffeine from tea is a good practice for a beginner. Try that first.

PS: Please open new threads without any references only in the Beginners section. Read the forum guidelines for more info on how to open new topics.
Quote: Originally posted by Random  
acid base extraction might work for those

solvent could be toluene

Is it so? Could you please cite us your references?




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[*] posted on 11-6-2013 at 07:45


Toluene is usually located in paint stores. Xylene could be used too.

Maybe you could even have results by chopping the plant material and then violently shaking it with vinegar, filtering and adding ammonia to precipitate the free base alkaloid. But using solvent would be I guess more efficient.

Anyway whatever you do take care, toxic alkaloids are not something to play with if you are not experienced. More toxic than cyanide.
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[*] posted on 11-6-2013 at 07:50


Quote: Originally posted by Nicodem  

Is it so? Could you please cite us your references?


http://www.u-picardie.fr/PCP/data/pub/2012-Attoumbre%20et%20...



Methanol and acetic acid are used as solvents in this case.

[Edited on 11-6-2013 by Random]
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[*] posted on 11-6-2013 at 07:53


If toluene happens to be what you're looking for:

Toluene is sometimes available at your hardware store. Synthesis is tricky, to say the least.
It can be distilled from some paint related products. (Help me out here.)
Random, why is it so?

Chloroform is relatively easy to make and dissolves most alkaloids. However solanine is a glycoalkaloid ([sugar]-O-[Alkaloid]) so I'm not sure if that changes it.




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[*] posted on 11-6-2013 at 07:58


Quote: Originally posted by Finnnicus  
If toluene happens to be what you're looking for:

Toluene is sometimes available at your hardware store. Synthesis is tricky, to say the least.
It can be distilled from some paint related products. (Help me out here.)
Random, why is it so?

Chloroform is relatively easy to make and dissolves most alkaloids. However solanine is a glycoalkaloid ([sugar]-O-[Alkaloid]) so I'm not sure if that changes it.


I thought it was one of easier to obtain solvents for amateur chemists. But as you can see, methanol can be used too, maybe even more efficient because of it's water miscibility.

I think I read somewhere that strong acids damage it's structure, but then again solanine hydrochloride was used as pesticide?
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[*] posted on 11-6-2013 at 08:28


Quote: Originally posted by Random  
I thought it was one of easier to obtain solvents for amateur chemists. But as you can see, methanol can be used too, maybe even more efficient because of it's water miscibility.

Please stop spreading misinformation. The article you cited never mentions the isolation of solanine solely by using methanol or any other solvent or extraction based methodology. They used centrifugal partition chromatography, because they found solanine could not be isolated in any easy way, not even preparative HPLC (at least not pure). I doubt PickledPackratParalysis has access to this kind of equipment. The methanol and acetic acid was only used to remove the soluble glycosidal components from the complex organic matter. What they obtained at this stage was barely any closer to solanine that potatoes themselves. The hard part only comes later.

Any simple extraction of solanine is more likely to be found in the older literature. I would guess it is less than efficient as old chemists only had recrystallizations and similar techniques to separate similar compounds. Anyway, some literature review is given in that J. Chromatogr. B article. But why would a beginner want to isolate a secondary metabolite that is commonly present only at ppm levels in some plant species? Even one such that is a pain to separate from its analogues. As if there are no other more reasonable practicing targets.




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[*] posted on 11-6-2013 at 08:36


Quote: Originally posted by Nicodem  
Quote: Originally posted by Random  
I thought it was one of easier to obtain solvents for amateur chemists. But as you can see, methanol can be used too, maybe even more efficient because of it's water miscibility.

Please stop spreading misinformation. The article you cited never mentions the isolation of solanine solely by using methanol or any other solvent or extraction based methodology. They used centrifugal partition chromatography, because they found solanine could not be isolated in any easy way, not even preparative HPLC (at least not pure). I doubt PickledPackratParalysis has access to this kind of equipment. The methanol and acetic acid was only used to remove the soluble glycosidal components from the complex organic matter. What they obtained at this stage was barely any closer to solanine that potatoes themselves. The hard part only comes later.

Any simple extraction of solanine is more likely to be found in the older literature. I would guess it is less than efficient as old chemists only had recrystallizations and similar techniques to separate similar compounds. Anyway, some literature review is given in that J. Chromatogr. B article. But why would a beginner want to isolate a secondary metabolite that is commonly present only at ppm levels in some plant species? Even one such that is a pain to separate from its analogues. As if there are no other more reasonable practicing targets.


I go by the fact that he actually doesn't need the pure alkaloid for some fine applications but only to examine the toxicity on his "lab rats". Of course leaves would be hard to use in a petri dish under a microscope, but an extract of these components, even if it still have had solanine in only miniscule amounts, would work perfectly.

To get pure solanine, perhaps black nightshade berries would work better, but he doesn't even need that. Solution of those 2.8g from 50g of leaves will contain more than enough solanine to examine it's toxic properties.

[Edited on 11-6-2013 by Random]
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[*] posted on 11-6-2013 at 09:08


Quote: Originally posted by Random  
Toluene is usually located in paint stores. Xylene could be used too.

Maybe you could even have results by chopping the plant material and then violently shaking it with vinegar, filtering and adding ammonia to precipitate the free base alkaloid. But using solvent would be I guess more efficient.

Anyway whatever you do take care, toxic alkaloids are not something to play with if you are not experienced. More toxic than cyanide.


Thanks!

Would centrifuging the plant in the vinegar work ? Or is violent shaking the preferred method? Could I pour off the 'green' vinegar so as to not get plant bits in it, and then precipitate the solanine out of the green vinegar?
Also baking soda is enough to cause a somewhat explosive reaction with vinegar... would ammonia do the same thing, or should it be safe?

Solanum tuberosum is the common potato plant, and I noticed in the article Random linked that the 50 grams were 'fresh' therefore, I assume not dry weight.
I think the solanine content of Solanum carolinense (horsenettle) is higher than that of the potato to begin with, and I have dried my horsenettle leaves. Does drying destroy the solanine or something?

Also as a side note, the black nightshade (Solanum nigrum) was widely believed to be highly toxic in days of yore, but the ripe berries contain almost no solanine, and I have in fact eaten several of them with no ill effects. If you meant the unripe green berries though, they do contain solanine, just like unripe tomatoes!
Another plant sometimes called black nightshade, (Atropa belladonna) contains atropine instead of solanine, and though highly toxic even when ripe, would not be the same as using real solanine in my experiment. Also it does not grow where I live.

http://foragersharvest.com/black-nightshade-2/

I don't really know what the chemicals in the article are, but I like the idea of Random's post about precipitating the alkaloid with ammonia. I have the materials for that.

I think using toluene as a solvent would invalidate my experiment... as I think it's more toxic than the solanine itself!
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[*] posted on 11-6-2013 at 09:16


what? toluene is not more toxic, Im sure. I work with toluene and benzene daily...



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[*] posted on 11-6-2013 at 09:41


Toluene can have serious affects on the body after long-term, continuous exposure, but it is certainly not more toxic than solanine. I have used it many times, and quite like it's odour. Benzene, however, very toxic and known to be carcinogenic, but I'm still not convinced that it is as toxic as solanine.

Wiki states that "a life-threatening dose for a regular-weight adult ranges about 400 mg solanine", which is 0.4 g, and significantly less than that of the aforementioned solvents.




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[*] posted on 11-6-2013 at 10:14


KK... LOL. Like I said I'm a total noob at chemistry. I typically considered it dangerous just because it's labelled as a 'solvent', but I guess some solvents are bad, and some are only slightly malicious. As far as solanine goes... Yeah, it's dangerous, but there's plants out there that are so dangerous that I don't even dare handle them. I don't have a scale, but it seems like about 8 grams of potato shoots could be life threatening? Just one single tiny leaf of Water Hemlock (Cicuta maculata) can kill you... I doubt there's more than 0.01 gram of cicutoxin in that.
Even people touching the plant apparently got poisoned enough to die!

http://en.wikipedia.org/wiki/Cicuta#Toxicity
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[*] posted on 11-6-2013 at 13:20


I have always struggled with plant extractions. They require patience, good technique, and above all proper materials or all you end up with is concentrated plant funk!
There are piles of info on A/B extractions around the net. Try one of the DMT ones, they are easy to understand step-by-step.
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[*] posted on 11-6-2013 at 15:41


Still no one's said if drying will destroy the solanine... Before I do the experiment, I need to know if my dried horsenettle will work, or if I need to go collect it fresh.
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[*] posted on 1-9-2013 at 18:54


in regards to your questions about decomposition/evaporation, solanine melts at 76 C and decomposes at over 200 C so the solanine should still be in the leaves after crushing.

after reading other mad scientists posts it appears this would be a hard extraction for the amateur. if you are interested in other poisons a list of more than 250 poisons/useful chemicals that can be found in mushrooms has been compiled.
http://www.sciencemadness.org/talk/viewthread.php?tid=18256#...




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[*] posted on 10-9-2013 at 11:02


I'd agree that most of these glycosides are hard to extract. Due to the polar nature of the glycoside (look at all those hydroxyl groups), I'd expect the substance to be soluble in methanol to an extent. Unfortunately, there is also a large steroid-like component, which makes it hard for me to say that a wash with hexane or chloroform won't remove the goods.

I'd suggest smaller MW alkaloids. DMT has been suggested, but beta-carboline alkaloids are also interesting (i.e from Syrian Rue). Gramine can be found in many aquatic grasses. These alkaloids are easily extracted by A/B pulls. In some cases, you may be able to wash the raw material with naphtha, toluene or hexane to remove lipids from the pulverized material in slightly acidic water (i.e with acetic acid) and then use aq. NaOH and the same solvent to extract free-amine alkaloids.
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