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Citizen Plant Science - Exploring the Aizoaceae

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I feel the succulent dimension holds an interesting element in potentially having more therapeutically useful "in the real world" dimensions than more commonly touted plant medicines for their often more gentle but occasionally empathogenic edge. Also, the combination of often pro-cognitive (PDE4 inhibition seen with mesembrine-type alkaloids) with potent antidepressant effects meets an unmet demand.

Part 1: Background and 'citizen analysis' using readily available materials 

 

461817869_mesembrymesembrinetest.thumb.jpg.f1b16f90d6ca0d5b2257f453710a0419.jpg

 

Some Aizoaceae have been analysed [1]:

2135791567_mesembrymesembrine.thumb.png.f423fb1df872f7eca80cffdbdfdceaae.png

I wanted to see if it was feasible to get some rough idea of the phytochemistry of a plant using only readily available materials eg. making it suitable for citizen science. I've been curious about simple TLC and paper chromatography as tools, particularly how feasible 'citizen TLC analysis' of plants is using a suitable paper, readily available solvent systems and simple visualisation techniques, compared to more conventional TLC.

Can simple maceration of a medicinal plant in a readily available benignish solvent, concentration, spotting on
common craft materials, developing the plate and OTC visualisation give some rough idea of the phytochemistry of a medicinal plant?

 

Sceletium has in the past been analysed via conventional TLC [2, 3] and more advanced techniques [4]

 

TLC.thumb.jpg.87846ee50b60a31a3c26a6fedb2f9a5c.jpg

 

1956669912_sceletsolventsystems.thumb.png.643725159cd51e033b1d94dc3b3db1a2.png

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It took about 30 trials to find a readily available solvent system and semi-suitable paper - after many failed attempts, I found an 'etch art paper' that seemed the best I could find. I'm still to follow up with confirmation on silica TLC plates but it seems to give *a very rough idea*

 

Sceletium tortuosum (unfermented) was used as a reference. This gives a main compound Rf = 0.5-0.54 on the craft paper.

 

I particularly wanted to research D. bosseranum and Trichodiadema stellatum

Method:

 

Sample preparation: Samples were dehydrated at 70 deg. C and powdered. The samples were macerated in isopropanol. If no phenolic constituents were expected, NaOH q.s. was used to basify, otherwise basified with ammonia solution. The isopropanol solutions were concentrated to a small sample.
 

Samples were spotted onto a plate, either a suitable craft paper, or silica gel plates. Acetone was used to elute the plate and I2 vapour (from OTC tincture) used as a visualisation technique.

Crude technique - Craft Paper

 

May be an image of indoor

 

Note: this technique is limited in effectiveness and I suggest if you're that keen to play around with something like this, I'd suggest you just stick with silica gel plates to save A LOT of hassle.

Delosperma bosseranum

 

bosseranum.thumb.jpg.cc64cec7d8ab510968193cbde8e9b7c1.jpg


image.thumb.png.fbcbf21d77ec1a8f27e90b5958f0a2a7.png

Sceletium tortuosum (unfermented) was compared to D. bosseranum. A compound with the same Rf as Sceletium was noted along with other constituents.

 

Trichodiadema stellatum (syn. barbatum)


May be an image of outdoors

image.thumb.png.5a939fb9a848e84e698a02eee189afaa.png

Sceletium tortuosum (unfermented) was compared to D. bosseranum. A compound with the same Rf as Sceletium was noted along with other constituents.

Mesembryanthemum cordifolium (syn. Aptenia cordifolia)


253714349_apteniafinal.thumb.jpg.021cef9d533de933091a319bb0ab5ff8.jpg

This has been studied and seems to contain 4,5-dihydro-4’-O-methylsceletenone  and 4’-O-methylsceletenone along with flavanoids, tannins, phenols, saponins, and cinnamic acid derivatives (and esters)

The characteristic Sceletium constituent was absent in these but other different compounds were present.

Will follow up with more conventional silica TLC which will hopefully have more easily reproducible results


 

461817869_mesembrymesembrinetest.thumb.jpg.f1b16f90d6ca0d5b2257f453710a0419.jpg

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bosseranum.thumb.jpg.cc64cec7d8ab510968193cbde8e9b7c1.jpg

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Edited by Alchemica
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Citizen Plant Science - Exploring the Aizoaceae

 

Despite a long history of traditional use as medicines, the Aizoaceae remain an under-studied family of plants [1]. They often contain phytocompounds such as alkaloids, flavonoids, steroids, and their related intermediary compounds, one of the commonly found alkaloids is the mesembrine-type alkaloids [2,3]. These plants are well known in traditional medicine systems for antidepressant, anxiolytic, antimicrobial, anti-inflammatory, and antioxidant effects.

 

Sceletium tortuosum (Figure 1.) contains mesembrine and derivatives (Figure 2.), an alkaloid not typically found in the emarcidum-type Sceletium spp. Other plants such as Delosperma pruinosum, and Delosperma pottsii [2] appeared to have some level of mesembrine but while Mesembryanthemum cordifolium syn. Aptenia cordifolia was initially thought to contain some levels of mesembrine, it seems instead to contain derivatives such as mesembrane sceletenone derivatives [4] which have in initial studies shown antidepressant activity superior to imipramine [5].  

 

937904725_Stortuosum.thumb.jpg.012179fc09a8f0f409f56fe1fb8cbc18.jpg

Figure 1. S. tortuosum

 

2138230592_mesembrinealks.thumb.png.131333a57119cd1c2b904cebc2527f11.png

Figure 2. Mesembrine and derivatives.

 

Other Sceletium spp. have been traditionally used, S. emarcidum "was valued as highly as S. tortuosum in Southern Africa by different tribes and makes a very good Kougoed product". While apparently devoid of mesembrine, it seems to contain 4'-O-demethylated mesembrine-type alkaloids [6]. Mesembrine has been found in Amaryllidaceae such as Narcissus pallidulus and Narcissus triandrus. Other Mesembryanthemums such as M. crystallinum and M. nodiflorum have been suggested to contain some levels of mesembrine.

 

More recently, Lampranthus spp. (Figure 3.) have been specifically marketed as Sceletium substitutes 'Chinese Kanna', or used as adulterants. These seem to contain mesembrenol and low levels of mesembrenone.

 

1866705325_lampranthusspectabilis.thumb.jpg.8cf2dcbfd85b453836b62fe7e4317f51.jpg

Figure 3. Lampranthus and mesembrenol

 

One early explorer called S. tortuosum  ‘the greatest Clearer of the Spirits, and the noblest Restorative in the World’. Traditional use of Sceletium in South Africa often involves the collection and fermentation of the plant material, which has been studied and lead to greater levels of mesembrine and changes to levels of mesembrenone [7] and reduce oxalate levels. 

 

Mesembrine is a potent serotonin reuptake inhibitor (Ki = 1.4 nM) and to a lesser extent PDE4 inhibitor. Other notable mesembrine-type alkaloids include mesembrenone (also a potent serotonin reuptake inhibitor [Ki = 27 nM] and a more potent PDE4 inhibitor than mesembrine itself), and mesembranol. Another assay found that Sceletium tortuosum comprising of > 70% (w/w) stabilized mesembrine was a monoamine releasing agent [8].

 

The pharmacological properties of mesembrine and it's derivatives are quite diverse, showing anti-inflammatory, cytoprotective, VMAT-2 upregulation, mild inhibition of AChE,  mild MAO inhibition, limited reuptake of NE and DA at high concentrations. Mesembrenol and mesembrenone seem to also share the SERT inhibitory and PDE4 inhibitory activitty.

 

Clinically, the Sceletium spp. have shown antidepressant, anxiolytic and cognitive enhancement effects, case studies demonstrating increased attention, focus, and motivation while a patient with “a baseline mood of depression alternating with anxiety”  felt “more focused, more engaged, and not so socially distant” after ten days [9].

 

Species such as Delosperma bosseranum (Figure 4) have been suggested by members of the ethnobotanical community to offer similar effects to Sceletium spp. but remain uncharacterised phytochemically and pharmacologically. Others such as Trichodiadema spp. (Figure 4), traditionally used as beer making roots known as 'Karee Moer' (T. barbartum syn. stellatum) as suggested to contain mesembrine but a detailed analysis is lacking (limited to positive alkaloid tests).

 

1907339565_mesembrymesembrinetest.thumb.jpg.cdf1865fbb2b4876264e13eef43f6057.jpg

 

Figure 4. The prototypical mesembrine containing plant, Sceletium and D. bosseranum and T. barbatum

 

The purpose of this citizen science was to explore a diverse range of Aizoaceae for mesembrine-type alkaloids, including uncharacterised ones such as Delosperma bosseranum and Trichodiadema barbatum and screen diverse Mesembryanthemums for possible mesembrine-type alkaloids.

 

[1] https://doi.org/10.1016/j.jep.2022.115988

[2] https://doi.org/10.1016/j.phytochem.2019.112061
[3] https://doi.org/10.1076%2Fphbi.36.3.173.6350
[4] https://def-sa.com/wp-content/uploads/2020/08/Gaffney_Candice_D_2006_0.pdf
[5] https://doi.org/10.1080/14786419.2020.1788019
[6] https://doi.org/10.3389%2Ffnut.2022.819753
[7] https://doi.org/10.1016/j.sajb.2018.10.011
[8] https://patents.google.com/patent/US20160038551A1/en
[9] https://www.researchgate.net/publication/328942189_Kabbo's_Kwain_The_Past_Present_and_Possible_Future_of_Kanna



A range of Aizoaceae (Silica, I2 visualisation) gave diverse phytochemical profiles

 

Trichodiadema stellatum (root) TS

806848014_tsplant.thumb.jpg.fcf6e194827508ce3d5d86010c9e5635.jpg

Trichodiadema bulbosum (leaf/stem) TB

Trichodiadema-bulbosum.thumb.jpg.4dd2e588d5c6ad4283109a6f6ea61a96.jpg
Sceletium tortuosum (root) ST

289878184_Stortuosum.thumb.jpg.b99fde525d0473627f4abaeca887d6ed.jpg
Sceletium emarcidum (leaf/stem) SE

1087692995_IMG_20230401_0918221.thumb.jpg.e3a1b0b48c539c5f0fab70b50ca5d36f.jpg 
Aptenia cordifolia AC

463408673_IMG_20230401_0918381.thumb.jpg.1fa07ad0ea767601b8e713045c8718c9.jpg
? Unknown Mesemb.

2010400956_IMG_20230401_0916211.thumb.jpg.1f0ded007528b8a02346deba6db0aeb8.jpg

Drosanthemum floribundum Dros.

1390647365_IMG_20230401_0919301.thumb.jpg.049af9fe69c4e292f76c2d2ebbb506ae.jpg
Mesembryanthemum (Red) [?Lampranthus] MR

2073362713_IMG_20230401_0916291.thumb.jpg.abd383943f98aefa24d945246678e62e.jpg
Mesembryanthemum (Gold) MG

1971714930_IMG_20230401_0917051.thumb.jpg.1f5c45cc9d57b415bfac5476f07b8a3c.jpg
Mesembryanthemum (Yellow, squarish stems) MY

267613657_IMG_20230401_0919161.thumb.jpg.8396dc4600c7c975739cf4d3c2277f0c.jpg
Mesembryanthemum (White) MW

41568320_IMG_20230401_0918571.thumb.jpg.57a728e6ab76d8f8d847f6f657dc8df4.jpg
D. bosseranum DB
D. floribundum DF


438056762_Azac.thumb.jpg.d59bb098efe4f5e3279cd7e541df0e0c.jpg

1. acetone elution

 

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2. acetone:white spirits:1:1 elution

 

To TLC soon

Tetragonia tetragonioides

warrigal.thumb.jpg.0beb582d4318e15660db9e2bb4f70918.jpg

Mesembryanthemum crystallinum

531020746_mcrystallinum.thumb.jpg.320ef905230dc1c85615681355362de6.jpg

Lampranthus spectabilis (Red)

719502141_lampranthusspectabilisgood.thumb.jpg.aed9509bf3e276acf461150989c1f277.jpg

D. echinatum

682652480_IMG_20230401_1836331.thumb.jpg.c3cffc2c04d63627a8f47f989797ae67.jpg

438056762_Azac.thumb.jpg.d59bb098efe4f5e3279cd7e541df0e0c.jpg

1402371526_Azmixedsol.thumb.jpg.0497a57c349cd070610b05807f3b0438.jpg

1087692995_IMG_20230401_0918221.thumb.jpg.e3a1b0b48c539c5f0fab70b50ca5d36f.jpg

463408673_IMG_20230401_0918381.thumb.jpg.1fa07ad0ea767601b8e713045c8718c9.jpg

2010400956_IMG_20230401_0916211.thumb.jpg.1f0ded007528b8a02346deba6db0aeb8.jpg

2073362713_IMG_20230401_0916291.thumb.jpg.abd383943f98aefa24d945246678e62e.jpg

1971714930_IMG_20230401_0917051.thumb.jpg.1f5c45cc9d57b415bfac5476f07b8a3c.jpg

267613657_IMG_20230401_0919161.thumb.jpg.8396dc4600c7c975739cf4d3c2277f0c.jpg

41568320_IMG_20230401_0918571.thumb.jpg.57a728e6ab76d8f8d847f6f657dc8df4.jpg

806848014_tsplant.thumb.jpg.fcf6e194827508ce3d5d86010c9e5635.jpg

Trichodiadema-bulbosum.thumb.jpg.4dd2e588d5c6ad4283109a6f6ea61a96.jpg

289878184_Stortuosum.thumb.jpg.b99fde525d0473627f4abaeca887d6ed.jpg

1390647365_IMG_20230401_0919301.thumb.jpg.049af9fe69c4e292f76c2d2ebbb506ae.jpg

warrigal.thumb.jpg.0beb582d4318e15660db9e2bb4f70918.jpg

531020746_mcrystallinum.thumb.jpg.320ef905230dc1c85615681355362de6.jpg

719502141_lampranthusspectabilisgood.thumb.jpg.aed9509bf3e276acf461150989c1f277.jpg

682652480_IMG_20230401_1836331.thumb.jpg.c3cffc2c04d63627a8f47f989797ae67.jpg

937904725_Stortuosum.thumb.jpg.012179fc09a8f0f409f56fe1fb8cbc18.jpg

2138230592_mesembrinealks.thumb.png.131333a57119cd1c2b904cebc2527f11.png

1866705325_lampranthusspectabilis.thumb.jpg.8cf2dcbfd85b453836b62fe7e4317f51.jpg

1907339565_mesembrymesembrinetest.thumb.jpg.cdf1865fbb2b4876264e13eef43f6057.jpg

Edited by Alchemica
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Morning lovely human. @Alchemica I so admire your work, you're a champion mate  and that's an understatement

 

Beautiful work, thank you for posting it here

 

Would it be possible to get reference compounds for molecules of interest? I know they're hell exxy, but is it possible? Or can you get reliability via the rf without them?

 

 

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i really think there is a lot to learn with these plants. thanks for putting in the effort for us 

 

the Trichodiadema that resides at my place is really starting to crank, i look forward to distributing it around to the local plant people 

 

 

 

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On 11/04/2023 at 12:23 PM, Alchemica said:

After some peer scrutiny on the initial attempt and revisions, here is a rough draft.

 

mesemb paper V2.pdf

 

How awesome this is makes me really happy

 

Lovely work my friend. So much happiness for its beauty

 

If youse haven't already read it, can definitely recommend

 

Thank you for sharing

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On 01/04/2023 at 10:07 AM, El Presidente Hillbillios said:

i really think there is a lot to learn with these plants. thanks for putting in the effort for us 

 

the Trichodiadema that resides at my place is really starting to crank, i look forward to distributing it around to the local plant people 

 

 

 

 

Yeah mine is taking off too, given how soggy and mouldy the local climate can be here I thought it would be doomed

 

Na, it's loving life, third set of new leaves I think

 

Hillbilly, be good to do side by side TLCs to compare climate, season and propagation mix differences over time to complement Alchemica's work, what do you reckon?

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Nice to see a mention of one of our native species; Tetragonum tetragonioides. I was very surprised to see it growing in almost every vegie garden I spotted in France a few years ago. It seems a lot more popular there than here, although always exclusively for edible qualities. I've never heard of any antidepressant effects from it previously.

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16 hours ago, Freakosystem said:

It seems a lot more popular there than here

Like a lot of these plants, T. tetragonioides makes an excellent ground cover. I don't know why it's such an uphill battle persuading people to cook it and eat it. I think people are (literally) sold on supermarket varieties of fresh food. As for "weeds," even if they are superfoods ... forget it. Definitely needs cooking but, and I wonder if that has an effect on medicinal value?

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Thanks for the input, feedback and for reading

Just random bits of non-Aizoaceae TLC info whilst experimenting

Tabernaemontana undulata (root bark) and T. orientalis (stem)

Samples were macerated in basified isopropanol (aq. ammonia), decanted and concentrated.

 

TLC (silica, glass backed, 0.2mm, I2 visualisation) with acetone elution gave significant trailing and poor separation of the constituents for both. Elution with acetone:white spirits 1:1 gave some separations of compounds from T. undulata (Rf =  0.13, 0.35, 0.56, 0.89) but poor separation of constituents in the T. orientalis.(one potential constituent Rf = 0.75). White spirits elution alone gave a band of constituents ~ Rf = 0.24 for both

 

Heimia


Contains  biphenylquinolizidine lactone alkaloids [1].  Plant material (leaf/stem) was soaked in basified isopropanol (aq. ammonia) and concentrated. Initial elution with acetone gave poor results but TLC (silica, 0.2mm, acetone:white spirits 1:1) gave distinct separation of compounds Rf = 0.43, 0.48, 0.55, 0.63, 0.95 Two (Rf = 0.43 and 0.95) were green-yellow/ yellow and fluorescent, the others plain visible pigments (green, blue-grey)

 

[1] https://www.shaman-australis.com/~auxin/heimia.html

 

hemia_mixed.thumb.jpg.5f2b51393b060b2be23b3a7a8bfff7ce.jpg

 

Lobelias

 

TLC with these posed issues in finding an adequate solvent system.

 

image.thumb.png.d20287530ffc39a36f3630ef975544fa.png1759806281_lobeliatupa.thumb.jpg.edf0a443451a67f24af0ce64a0daf0aa.jpg

 

L. cardinalis: Lobinaline as the major alkaloidal constituent (below)

 

image.thumb.png.7c75149f705b6b68b2c7255ea71cf3b4.png

 
L. tupa: lobelanidine, lobeline and pentylsedinine etc (below)

 

1-Figure1-1.thumb.png.6f24673edf6ecec4de5b153437341446.png

Dried aerial plant material was allowed to sit overnight in basified isopropanol (aq. ammonia), decanted and concentrated.


TLC (silica, glass backed 0.2mm, acetone elution, I2 visualisation) gave a distinct compound Rf = 0.65 for the L. cardinalis but did not give any notable visible constituents for the L. tupa.


TLC (silica, glass backed 0.2mm, acetone:white spirits 1:1, I2 visualisation) gave a distinct compound Rf = 0.40 for L. cardinalis and hints of a potential compound Rf = 0.31 for the L. tupa.

 

Ashwagandha leaf withanolides

 

Leaf withanolide constituents mainly include withaferin A and withanone

 

1527356075_withanonewithaferina.thumb.png.6290263182e9d714e843ab8f37211ade.png

 

Crushed dried leaf was macerated in isopropanol and the sample concentrated. TLC (silica, glass backed, 0.2 mm, I2 visualisation) gave poor results eluted with acetone but with mixed solvent (acetone:white spirits 1:1) gave at least four constituents Rf = 0.23, 0.33, 0.48 and 0.55

 

 

Exploring a relatively uncharacterised Leguminosae - Senegalia rugata 


Senegalia rugata syn. A. concinna - Sompoi or Shikakai - seen in Fig. 1 and 2. belongs to the Leguminosae family and is a medicinal plant widely grown in Southern Asia including India, Myanmar and Thailand. It is commonly known as shikakai and soap pod as it is used for cleansing of hair as a natural shampoo. 
 
 Acacia_concinna_Blanco2.374-cropped.thumb.png.84612802dd6eccde0d19a5f84eb512a8.pngShikakai_(Senegalia_rugata)_seed_pods.thumb.jpg.d352560ddfe821c4ebf17b63c633c25c.jpg


The phytochemistry has been explored only to a limited extent [1,2]. There is also suggestion of internal use and the calyctomine (Fig. 3) has been used in the supplement industry [3]. 

 

2.thumb.jpg.8025250108a90c8996d94fec830fd69f.jpg

 


Initial phytochemical study

 

cal.thumb.jpg.83da12c4b807a5e3be3dd5f663275d4a.jpg

 
Figure 3. calyctomine


Alkaloids, flavonoids, saponins, and phenolics were found in all extracts while phytosterols was found only in the ethanol extract. It yields lupeol, spinasterol, acacic acid, lactone, and the natural sugars glucose, arabinose and rhamnose. It also contains hexacosanol, spinasterone, oxalic acid, tartaric acid, citric acid, succinic acid, ascorbic acid, and the alkaloids calyctomine, a tetrahydroisoquinoline, and nicotine.
 

Various other compounds have been isolated and characterised from the pods of this plant such as epigallocatechin, acacic acid lactone, machaerinic acid and its lactone, sapogenin-B, acacidiol, acacigenin-B, and kinmoonosides
 

Experimental:
Plant material was macerated in basified isopropanol (NaOH) and concentrated.


Initial TLC (Silica, glass backed, 0.2mm, acetone elution, I2 visualisation) gave two main constituents, Rf = 0.14 and 0.59 but there was significant trailing of the compounds. Elution with mixed solvent (acetone:white spirits 1:1) gave a major constituent Rf = 0.65.

 

[1] Screening of Secondary Metabolites and Antibacterial Activity of Acacia concinna
http://dx.doi.org/10.3923/jm.2010.974.979
[2] Isolation and Evaluation of Anti-inflammatory activity of Epigallocatechin from Senegalia rugata along with PUFAs
https://rjptonline.org/AbstractView.aspx?PID=2021-14-11-23
[3] Calyctomine HCL?
https://anabolicminds.com/community/threads/calyctomine-hcl.282282/

hemia_mixed.thumb.jpg.5f2b51393b060b2be23b3a7a8bfff7ce.jpg

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1527356075_withanonewithaferina.thumb.png.6290263182e9d714e843ab8f37211ade.png

Acacia_concinna_Blanco2.374-cropped.thumb.png.84612802dd6eccde0d19a5f84eb512a8.png

Shikakai_(Senegalia_rugata)_seed_pods.thumb.jpg.d352560ddfe821c4ebf17b63c633c25c.jpg

2.thumb.jpg.8025250108a90c8996d94fec830fd69f.jpg

cal.thumb.jpg.83da12c4b807a5e3be3dd5f663275d4a.jpg

Edited by Alchemica
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I can't keep up with you mate, I'll have to digest this later.

 

Still going through your lovely Azo paper and looking at replicating it alongside some new variables here nom...nom nom :D

 

Such lovely work, thank you

 

Definitely needs cooking but, and I wonder if that has an effect on medicinal value?

 

Yeah I've been wondering the same.

 

If there are easily made anni-d extracts that bypass the oxalates that'd be cool tho. I'd still like to know the difference between cooked and raw for potential supplementation to the same effect tho- I'd rather cook a feed occasionally than harvest a bunch to extract

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I've been busy expanding on this research, hopefully it's of interest/inspiration to others:

So far the research extends to:

Citizen TLC Phytochemical Screening of Diverse Mesembryanthemums
https://pdfhost.io/v/gugGrtnCj_

Phytochemistry of Aptenia
https://pdfhost.io/v/dq6SpR9nM_aptenia

Citizen TLC analysis of marketed commercial Sceletium tortuosum products: https://pdfhost.io/v/SVvI3PQwb_TLC_commercial_sceletium_produc

Using TLC to guide discovery of hypothetical new Kanna substitutes
https://pdfhost.io/v/A4u.08qVQ_kanna_substitutes_TLC

Utilising yeasts to encourage the bioconversion of mesembrine-type alkaloids

yeasts to encourage bioconversi | PDF Host

 

Initial TLC study of an uncharacterised Sceletium ('Little Karoo')

 https://pdfhost.io/v/.ASjnTMdo_Initial_TLC_study_of_an_unchara

 

Sceletium Chemotypes - Characterisation of a 'Superior Quality' Sceletium product

sceletium chemotypes | PDF Host

 

Reagent analysis of phytochemicals - application to Sceletium spp and Mesembryanthemums.
Reagent analysis of phytochemicals - application to Sceletium spp and Mesembryanthemums. | PDF Host

Edited by Alchemica
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