trans-crocetin - novel NMDA antagonist from saffron, and it's preparation

[tantric]

Saffron extract and trans-crocetin inhibit glutamatergic synaptic transmission in rat cortical brain slices

In conclusion, this is, to our knowledge, the first report toprovide evidence of the inhibition of postsynaptically lo-cated NMDA and kainate receptors by a hydro-ethanolicCrocus sativusL. extract, which is partly mediated bytrans-crocetin.

Effective isolation protocol for secondary metabolites from saffron: semi-preparative scale preparation of crocin-1 and trans-crocetin

The following protocol describes effective methods to obtain both compounds from an EtOH-water extract (2:8) in good yields (about 43% related to the starting material). Crocin-1 (purity>90%) can be obtained from the extract by means of partition chromatography (FCPC) in a single run without fractionation of the mobile phase by using only the stationary phase and in yields of about 48%, related to the saffron extract. Trans-crocetin can be obtained from the EtOH-water extract by enzymatic deglycosylation of crocins using commercially available cheap glycosidase mixtures as e.g. Röhm Enzyme® or RohamentCL®. Further polishing can be achieved by flash chromatography on MCI® stationary phase with yields between 6 and 11%. The protocols described provide effective isolation of crocin-1 and trans-crocetin reference compounds for further preclinical and analytical studies with saffron extracts.

 

[sekio]

Too bad saffron/crocus is one of the most expensive botanical substances in the world by mass.

 

[tantric]

true - but it shouldn't be hard to synthesize....

not sure about the trans part - it's been a long time since i had o-chem

 

[sekio]

Actually, with all those double bonds, it would be pretty difficult to make it in high yield through total synthesis, I'm afraid. There are synthetic methods for making molecules with double bonds, but I dunno about 10 conjugated ones in a row. In addition, having so many double bonds would probably make it reactive towards ozone, halogens, oxygen and/or UV light etc. meaning you'd need to store it in the dark under N2.

Maybe it could be manufactured from carotene or the like, or bio-synthetically made via enzymes? It's scary how expensive stuff like lycopene is from places like Sigma though ... so even partial synthesis would be a money sinking endeavor.

 

[asecin]

i was reading those metabolites are easily absorbed when mixed with oil, or fat and heated. do you really need to extract them specifically when you can consume the whole herb as it is, heated in oil/fat

 

[sekio]

thats right asecin, in fact thats what I would recommend most people try rather than attempting to do anything fancy with partiton chromatography or weird solvents.

also, i did a quick google on the words "saffron price" and an article from 2006 says this

Saffron, the most expensive spice, is usually sold by the gram - just a small cluster of slender red threads in a tiny glass bottle. At [some spice store] in Chicago, [the owners] sell a gram of superior grade saffron for $6.79, and an even finer version, known as coupé grade, for $8.29

I don't know how much crocetin is actually in saffron but I can't imagine that it would be a lot by weight... are you willing to spend upwards of $70 on herbal material just to get a mild buzz???

 

[Limpet_Chicken]

Hm, interesting.

Its a little old now, been stored in an opened, although rolled up plastic bag for a few years. But I do happen to have a fair sized bag if the stuff hanging around, brought it back when I went on holiday to turkey, where it was remarkably cheap, at least, compared to the few scraps one usually sees.

Anyone care to hazard a guess as to active human threshold levels? pretty sure I recall seeing other posts regarding saffron around on BL in the distant past. Time to go do some digging.

 

[asecin]

im curious as to what exactly IS that "mild buzz" as sekio describes it.

about its inhibition of glutamate, sekio would you think thats a good thing for use in alcohol withdrawal?

 

[tantric]

if a reasonable starting dose of the herb can be found, i'm game.

then again, no...

Re: Recreational use of Saffron?
I have experienced mild psychoactive effects from sublingual use of high quality Saffron.

I experimented, after coming across a website stating that Saffron has a similar pharmacological profile to MDMA, only weaker. * Not claiming to be true.

The effects obtained were a definitive mood lift and a feeling of warmth.

I experimented with several brands of Saffron before having any success. Store bought is generally no good. I eventually imported some Saffron from a producer in India. Pale yellow strands are worthless.

This stuff will stain your teeth yellow.

People have overdosed from Saffron in the past. Be aware that some of the constituents are carcinogenic in higher doses (not that much higher).

Do your research first.

Although the LD50 of Saffron is around 20g/KG, there have been deaths at much lower doses as a result of other overdose symptoms.

After having taken 1.5 grams, one woman bled to death (Looking for definitive source).

Interestingly, there are studies into the anti-carcinogenic and anti-mutagenic properties of Saffron.

Saffrons anti-depressant qualities alone are quite widely recognised.

EDIT: Recreational dose, will depend entirely on the quality of your product. Aim for the best possible quality, but anything less will be a waste of time.

Of course, start with a tiny amount to gauge for allergic reactions etc.. (Which Saffron can cause). Carefully build the size of your doses to gauge reaction, allowing a few days in between.

I have used up to around 300-400 mgs in the past at one time.

-post on another forum

 

[Weltmeister]

Youll probably safe a lot of money by just growing the saffron yourself. Its easy to do and grows almost anywhere. The high price is only due to the amount of manual labor involved in producing the strings.

 

[asecin]

it doesnt grow everywhere lol and yes the labour costs a bit too much but also the fact you need to grow hundreds of flowers for few stigmas. just to make a gram you will need like 100 flowers

 

[Weltmeister]

I was thinking more along the lines of using the whole plant and not just the stigmas. Im guessing that if the stigmas contain it than the rest of the plant contains it aswell. Unfortunately i cant seem to find any infos about concentrations in other parts of the plant.

I might have exaggerated the part about it growing anywhere a bit but it certainly isnt hard to grow

 

[Limpet_Chicken]

I'd very much wish to know if that report about the woman bleeding out can be validated.

And also if she made a huge and awful mistake, taking instead not Crocus sativus, but meadow saffron, Colchicum autumnale, the natural source of the highly toxic compound (although in-vitro, extremely useful) colchicine. Which really would present no surprise f it caused such a fate.

 

[sekio]

Saffron is technoically only the styles, I believe that the remainder of the plant lacks the trans-crocetin you'd want, and may indeed have harmful alkaloids.

 

[asecin]

I'd very much wish to know if that report about the woman bleeding out can be validated.

And also if she made a huge and awful mistake, taking instead not Crocus sativus, but meadow saffron, Colchicum autumnale, the natural source of the highly toxic compound (although in-vitro, extremely useful) colchicine. Which really would present no surprise f it caused such a fate.

in literature there is a lot of whats referred to as "bastard saffron" because of its high price a lot of substitutes were distributed and from what i gather its mostly safflower but also various other plants so im not surprised about someone poisoning themselves on crap