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Alkaloid Profiles of Mimosa tenuiflora and Associated Methods of Analysis Options
 
Shaolin
Moderator
#1 Posted : 1/21/2012 2:27:13 PM
Alkaloid profiles of Mimosa tenuiflora and associated methods of analysis
Gardner, D. R. Riet-Correa, F. Panter, K. E., 2011

The alkaloid contents of the leaves and seeds of M. tenuiflora collected from northeastern Brazil were studied. Alkaloids were isolated by classical acid/base extraction procedures and by cation exchange solid phase extraction. The crude alkaloid fractions were then analysed by thin layer chromatography (TLC), gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-mass spectrometry (LC-MS).

In the initial analysis by GC-MS, two major alkaloids were detected and were identified as N,N-dimethyltryptamine (DMT) and 2-methylcarboline. A third alkaloid was only detected when extraction by method A was conducted. TLC analysis of the extracts also showed the presence of two major alkaloids. DMT and 2-methylcarboline were detected following GC-MS analysis. LC/UV/MS detected five alkaloids with UV and MS data consistent with tryptamine type alkaloids. These included DMT and 2-methylcarboline, and three unknown alkaloids. At least three possible minor alkaloids were detected, but their UV spectra was not consistent with the tryptamine type alkaloids. The presence of a possible artifact alkaloid was observed by LC-UV-MS analysis when extracts were prepared using extraction method A.

Seed and leaf samples collected at different years were extracted and analysed by TLC and LC-MS. Significant differences were observed in the alkaloid profiles between seed and leaves in that the two major spots in the TLC chromatograms were absent in seed samples. The best method of analysis appeared to be solid phase extraction followed by LC/UV/MS.
Got GVG ? Mhm. Got DMT ?

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justine
#2 Posted : 1/21/2012 3:04:11 PM
Great find shaolin! Very happy

Too bad they don't mention how much DMT was detected in these seeds.
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Dozuki
Chemical expertSenior Member
#3 Posted : 1/21/2012 3:50:33 PM
Very interesting read, thanks for posting!!!
 
nen888
Acacia expert | Skills: Acacia, Botany, Tryptamines, CounsellingExtraordinary knowledge | Skills: Acacia, Botany, Tryptamines, CounsellingSenior Member | Skills: Acacia, Botany, Tryptamines, Counselling
#4 Posted : 1/21/2012 3:56:09 PM
..yeah thank you Shaolin, just finished reading..
i think there may be more than one species of mimosa presented as M. hostilis (tenuiflora) by suppliers..we seem to be seeing evidence emerging of slight chemical variability within the species..
 
endlessness
Moderator
#5 Posted : 1/21/2012 6:35:35 PM
Excellent finding.. Funny they also get this same compound me and dozuki been getting in TLC, with a higher Rf.. They say it might be 2MTHBC but that they cant know without a standard.. I've found a supplier for a standard but its around 350e for a gram, pretty steep price...

They do not find any NMT, but they are extracting from seeds and leafs, neither bark nor rootbark.. Also they do not find yuremamine, and while there are several minor peaks, they do not try to hypothesize what they could be..

I also found interesting how in the GC-MS chromatogram of leafs, you can see 2MTHBC has even higher amounts than DMT!
 
Dozuki
Chemical expertSenior Member
#6 Posted : 1/21/2012 7:08:56 PM
endlessness wrote:
they do not try to hypothesize what they could be..


Other than the peaks with MH+ of 175, 201, and 205 they say are consistent with tryptamine type alkaloids based on their UV and MS data [my paraphrasing]. And that the other 3 peaks of MH+ of 122, 136, and 166 are not consistent with tryptamines. Alkaloid MH+ 247 is an artifact of the A/B extraction process.

Note that the MH+ 201 *may be* the same compound that shows up in your MS @ 200. DMT in your MS shows a similar pattern, showing up @ M+ 188 and theirs @ MH+ 189.

Alk 247 is shown in their TLC plate #1, Lane #3, and seems to be similar to spot #1 with the high rF in the last plate I posted (Plate #20) in the Jungle Spice analysis thread. This is the spot that disappears in the extraction after 4 days and I am of the opinion that it is a yuremamine degradation product (YDP). This would make sense, as they shouldn't show yuremamine in A/B because of the basic condition as stated in the original yurmamine isolation paper. They also use heat in their procedures, again, the yurmamine paper shows this to break the compound down as well.

It would have been interesting to see the rest of the MS data. I.E: what other prominent peaks there were.
 
endlessness
Moderator
#7 Posted : 1/22/2012 12:38:07 AM
Yeah, I would bet their alkaloid 201 is the same as what I've found, the probable 1,2-dimethyl-THBC, considering on the GC-MS it also appears just after 2MTHBC...


And yeah, good point about why yuremamine didnt show up in their product even if its present in leaf/seeds, because they used acidic/basic conditions that would break it down.

By the way as for alk 247, dont you mean plate 1 late 3? because plate 1 lane 1 theres only dmt and an unknown alkaloid that they at no point say it 247, but suggest it might be 2MTHBC, right?


I was wondering if it would seem suspicious in any way if I emailed this D. Gardner at ARS USDA, told him what I thought was potential identification for alk 201 and ask if he could share the mass spectra of the different peaks....
 
Dozuki
Chemical expertSenior Member
#8 Posted : 1/22/2012 1:39:02 AM
endlessness wrote:
By the way as for alk 247, dont you mean plate 1 late 3?


Yes, you are correct, It's a typo on my part. I fixed it above.

You could email Mr. Gardner, and possibly get an answer if done professionally. Which, I would totally image that you would do.

However, in some ways it still seems like comparing apples to oranges as they were studying leaf material and not root bark. If we can find references for the MS specs of these alkaloids, surely they could as well. It seems that they didn't really find it much of any significance. But, I may be totally off base in this assumption as well.
 
nen888
Acacia expert | Skills: Acacia, Botany, Tryptamines, CounsellingExtraordinary knowledge | Skills: Acacia, Botany, Tryptamines, CounsellingSenior Member | Skills: Acacia, Botany, Tryptamines, Counselling
#9 Posted : 2/10/2012 3:36:02 AM
..thought i'd post this here for the general interest of Mimosa phytochemical analysis..
nen888 attached the following image(s):
The Occurrence of Tryptamine and N-Methyltryptamine in Mimosa Somnians.jpg (289kb) downloaded 172 time(s).
 
 
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