Tobacco Extractions: A Gardener's Guide

[givemeaname]

Hi. I enjoy gardening as a hobby, mainly nicotiana (ornamental tobacco) and medicinal uses of plants. I am not a professional chemist.

Recently I have learned that uncured tobacco contains compounds called cembranoids and that these may have profound medical uses.

http://www.ulm.edu/universityrelations/news/july11/anticancer.html
http://www.iupac.org/publications/pac/pdf/1990/pdf/6207x1353.pdf

What I am curious about is how to isolate these compounds, in as practical way as possible, without extracting nicotine. I have heard that most of the nicotine is contained inside the leaf especially the upper leaves, so the flower calyxes are desired to avoid nicotine and are also the most resinous parts of the plant (and thus contain more terpenoids). Since nicotine is water soluble I imagine that soaking the material in water for a time to remove nicotine and then doing an extraction would work. I don't think that would be enough though and I know full well the dangers of nicotine. Shocked

Also in the resin exudate of tobacco would probably be N-Hydroxyacylnornicotine (a selective toxin to hornworm larvae), which interests me but also would need to be removed. I doubt that it is very toxic or carcinogenic to humans, since nicotine metabolites like nornicotine are much less potent (tobacco field workers get covered in the resins regularly). But I would like to know more information.

N-Hydroxyacylnornicotine: http://www.plantphysiol.org/content/82/2/479.full.pdf

 

[chemisttree]

Coming up with a workable scheme for the isolation and purification of natural products is not an armchair activity! The patent has the following information.

The extraction and isolation of compounds 1 and 21 was carried out in the following manner. 27.2 kg of fresh tobacco leaf powder (Custom Blends, NY, 27.2 Kg) was extracted with hexane (130 L) in percolators three times at room temperature. The hexane extract was concentrated under vacuum and dried extract (1050 g) was vacuum liquid chromatographed on silica gel (200-300 mesh, 2 Kg, Natland International Corporation) using gradient n-hexane/EtOAc to yield a crude cembranoid-containing fraction (64.0 g) which was further chromatographed on normal phase and finally on reversed phase silica gel (MeOH--H2O, 2:3, isocratic) to give compound 1 (1, 3.6 g) and compound 21 (17.9 g).

That's just how I'd do it!

 

[turbo]

Wow! That would be some hobby. I'd need access to the pulp mill's research lab, and some additional supplies and equipment to pull that off.

 

[gravenewworld]

Yeah, it's virtually impossible without industrial quality lab equipment to extract the material, purify it, and perform spec on it.

 

[givemeaname]

What about just extracting and separating the resins from the alkaloids? Would that be something a layman like me could handle without dying?

 

[turbo]

What about just extracting and separating the resins from the alkaloids? Would that be something a layman like me could handle without dying?

I don't think so! That's a long, hard (expensive) uphill slog.

 

[givemeaname]

Thanks for your input everyone

 

[chemisttree]

It actually isn't too difficult to separate the terpenes from the alkaloids if you have the proper equipment. An alcohol extraction followed by a few extractions using hexanes and water with some acid and then with some base should do it.

 

[givemeaname]

chemisttree, do you think it would be cheaper and easier to hire a chemist?

 

[chemisttree]

Easier, safer and probably purer but not cheaper. You might try to have a chemistry professor at a local university or community college do that for you. This type of alkaloid extraction is performed as an undergraduate laboratory excercise using tea/caffeine instead of tobacco/nicotine.

 

[givemeaname]

That helps a lot, thanks. Do you know about how much it would cost in total? I'm assuming chemist's are paid by the hour.