gibberellin + jasmonic acid = more trichomes?

[Sir D]

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[PerroVerde]

I used the Jaz plant strengthener at two weeks into bloom then the Jaz rose spray at 300ppm around four and a half weeks of bloom. I'm very impressed with the Jaz product line and the results they have delivered. No "Nuked" plants here, just super sticky, crystal covered, smelly herd...

 

[omera1]

Hedione is usually one specific stereoisomer of methyl hihydrojasmonate. i understand stereoisomerism very poorly have no idea how this would effect the efficacy of the product. Put simply, all methyl dihydrojasmonate is not the same and this is a form that could potentially be useless for us. Im currently waiting for a response from a chemistry major on the likely phytoactivity of commericial hedione products. There's very little experimentation done on MDHJ, ive only seen 3 studies that have used any form of MDHJ, 2 studies on tobacco and nicotine biosynthesis, and one study on the california poppy and alkaloid biosynthesis. so this puts us in a bit of a scientific blind spot.

Methyl Jasmonate is being used extensively in cancer studies as a potential cure for cancer. It often causes cancer cell apoptosis without having any effect on healthy cells.

so pure MeJa would be best ?

 

[aus2canibasiva]

Bump for an awesome thread!
Have you seen this SHAGGY??

Any input on the subject shaggy?


Has anyone had any experience with this combo, if so how much did you use?
What were the results?

Peace.

 

[BayBHuey]

Try this https://shop.perfumersapprentice.com/p-6100-hedione-methyl-dihydrojasmonate.aspx

BayBHuey

 

[BayBHuey]

How is ebay cheaper???????

I see at ebay Northwest Biotech sells 100ml for 30 bucks and like 3 bucks shipping

at perfumersapprentice . com they sell 80ml fo 10 bucks and 3 for shipping as well

now please help me understand how ebay is cheaper


BayBHuey

 

[BayBHuey]

Ahhhh mr windrock now how did the price go from 30 bucks to 13 bucks...hmmmm if I didnt know better Id say your affiliated with Northwest Biotech and trying to advertise on IC mag...that is a big nono here

BayBHuey

 

[merkaba]

Stereoisomers are sort of like your hand in the mirror, same thing but different configuration. They have the same atoms, same bonds but a different arrangement. A great example is the drug ibuprofen and the (S) and (R) isomers of it. The letters (S and R) have to do with the location of the atoms in 3-D space, the (S) isomer is pharmacologically active (has the desired effect) however the (R) is less effective - some say not at all. That is why Advil brand ibuprofen is actually more effective per dosage than "Brand X" knock off - it has a higher concentration of the active molecule. Sooooo....Hedione has 4 different configurations and from what I have seen on retail sights it tends to be an equal blend of all for isomers.

 

[Only Ornamental]

This thread has been brought to my attention by Shaggy... as I'm sometimes a bit lazy, I'll more or less copy-past two emails I wrote regarding the subject including a few modification (in blue, so that Shaggy knows what he missed ).

Email 1:
Hedione, patented in 1959 by Firmenich, is the racemic mixture of methyl dihydrojasmonate (aka (+/-)-methyl dihydrojasmonate) containing roughly equal parts of all four stereoisomers.
Someone might have come to the wrong conclusion because the compound is often listed as (-)-epimer, although being a mixture, because the natural form, jasmonic acid, is usually depicted as (-)-epimer (see comment at the end). The newer 'version' from 1993 is called Hedione HC and contains only the cis-isomers; the latest 'member' of the family, synthesised in 1996, is termed Paradisone and is the enantiopure form of the 1R,2S-(+)-methyl epidihydrojasmonate (the active highly fragrant cis-isomer).
As said, the 'normal' form of jasmonic acid is mostly 1R,2R-(-)-Z-jasmonic acid which has a weak jasmine odour and a moderate bioactivity. Paradisone on the other hand corresponds to the intensely aromatic and highly bioactive form (notably, it's the dihydro-derivative which is somewhat less active but more stable than natural JA) and is obviously the most expensive one too. This very active form corresponds also to the real natural isomer which, due its sterical hindrance and keto-enol tautomerism, tends to epimerise during isolation and storage to the usually described derivative 1R,2R-(-)-methyl dihydrojasmonate or in short (-)-methyl dihydrojasmonate (in case of essential oils and plant extracts, it would be (-)-jasmonic acid). In fact, many older studies on jasmonic acid and/or methyl jasmonate used a racemic mixture comprising mainly of the stable two trans-isomers; one of the reasons why Firmenich got so famous for Hedione and more so the newer versions which are the ones way more difficult to synthesise. The favoured form under common conditions is a roughly 5:95 ratio favouring the less or even inactive form. This means that many commercial products, although synthesised at a given ratio will be converted once in contact with water; Hedione is therefore often a mix of 10:90 (+/-)-cis- to (+/-)-trans-isomers.
Why the most active isomer in plants is also the one with the strongest odour, I do not know... maybe because it's the natural one?
Remains to be said that all isomers show some activities in certain tests, most of all the two naturally occurring 1R-enantiomers, usually have the same net effect, and will produce the same results just to varying degrees but the 1R,2R-epimer (may that be jasmonic acid or Paradisone) shows always the strongest activity. Notably, the methyl ester renders the molecule more active than the free acid but the lack the double bond in the pentyl side-chain greatly reduces it. Unfortunately, there is neither much data on dihydro-derivatives nor on the used enantiomers. Hence, different publications show, depending on the enantiopurity of the dihydro-derivative as much as that of the reference jasmonic acid (which are both usually not known nor cared about!), an activity of 10 to 50% or zero activity. Comparing the commonly used concentration of (-)-jasmonic acid (the less active enantiomer usually used) with that of JAZ Rose Spray (likely the 'degraded' racemate of methyl dihydrojasmonate) implies an activity of 0.1 to 1% of the latter.

(And here I cut some stuff out)

Email 2:
Forgot to mention:
1R,2S-(+)-epijasmonate is also termed 3R,7S-(+)-iso-jasmonate, depending on the used nomenclature .
As mentioned (and I'm sure you don't really remember, although this is the important part) the epijasmonates (resp. iso-jasmonates) transform into the trans-enantiomers. As the former are more active than the latter (though you find some publications which state the opposite but that's based on a mistake and has been copied several times...he even copied the mistake from himself and stated the opposite a page later...such an idiot... ) this means the following for the price/activity calculation:

1R,2S-(+)-Methyl dihydroepijasmonate (1) has full bioactivity and a very strong odour
1R,2R-(-)-Methyl dihydrojasmonate (2) has still some bioactivity and a moderate odour
1S,2R-(-)-Methyl dihydroepijasmonate (3) has a very weak activity but no odour
1S,2S-(+)-Methyl dihydrojasmonate (4) is usually bare of any activity and odour

It looks like if many results prior to 2007 are flawed as they assumed (-)-jasmonic acid to be the active form due the non-availability of (+)-iso-jasmonic acid and also traces of that on in the former (especially in tests using the really-really active isoleucine-adduct). That means, we don't know how active the four above substances really are ;( .
For the sake of simplicity (relative simplicity), I base bioactivity on odour intensity; in fact, it could well be that only compound 1 has an activity at all and the 10% of compound 2 are just the few percent which epimerised. Also, I ignore the 95:5 epimerisation ratio, feel free to calculate yourself :
1: 100% active
2: 10% active
3: 1% active
4: 0% active
That means, Hedione, the equal parts mix, has an activity or 27.5% (just after synthesis)
Hedione HC, the mix of 1 and 3 has about 50% activity
Paradisone (compound 1) has 100% activity

Now you buy that stuff, put it into solution, and get hit by the train called Murphy's Law... epimerisation occurs (the more water and the more pH deviates from 7, the faster) and product 1 slowly turns into product 2 and product 3 into 4.
Hedione becomes a mixture of 2 and 4, which has a total activity of 5%.
Hedione HC first turns into something like Hedione and then obviously into the same 5% mix as above.
Paradisone on the other hand slowly turns into a mix of 1 and 2 and finally becomes 2, or 10% activity.
Do the maths and you will see that with Hedione, you spend less and lose only 5 times whereas with Heidone HC you spend more and lose 10 times only to find yourself with the same stuff as if you had bought standard Hedione.
With Paradisone, you spend a lot of money only to lose 10 times but at least ending with something having 10% activity.

The logic conclusion is: buy compound 2 if it's not too expensive because that way you buy 10% activity and keep the 10% no matter what. Consistency or spraying every time the exact same thing is most important. Alternatively, go for Hedione as that one only loses 5 times, certainly contains an active ingredient (1) and isn't expensive .
But again, the % activity are a rough estimate and the pure compound 2 may not be active at all but only Paradisone!! Without proper testing (which hasn't been done), we'll never know...

(Again, I cut some stuff out)

Hope that helps and wasn't too much confusion... If so, don't worry, you aren't the only ones; so far, I found three papers (one done by Firmenich itself, one sponsored by Firmenich, and one written by one of the 'gods' of jasmonic acid chemistry and signalling, imagine that!) wherein they used the wrong stereochemical nomenclature, drew the wrong enantiomer, or mixed the biological activity up.

 

[shaggyballs]

Well said OO !
And what timing, weird.
When this guy speaks, ya'll listen up.
But good luck keeping up, he is Quick!
shag

 

[plastochron]

This thread has been brought to my attention by Shaggy... as I'm sometimes a bit lazy, I'll more or less copy-past two emails I wrote regarding the subject including a few modification (in blue, so that Shaggy knows what he missed ).

Email 1:
Hedione, patented in 1959 by Firmenich, is the racemic mixture of methyl dihydrojasmonate (aka (+/-)-methyl dihydrojasmonate) containing roughly equal parts of all four stereoisomers.
Someone might have come to the wrong conclusion because the compound is often listed as (-)-epimer, although being a mixture, because the natural form, jasmonic acid, is usually depicted as (-)-epimer (see comment at the end). The newer 'version' from 1993 is called Hedione HC and contains only the cis-isomers; the latest 'member' of the family, synthesised in 1996, is termed Paradisone and is the enantiopure form of the 1R,2S-(+)-methyl epidihydrojasmonate (the active highly fragrant cis-isomer).
As said, the 'normal' form of jasmonic acid is mostly 1R,2R-(-)-Z-jasmonic acid which has a weak jasmine odour and a moderate bioactivity. Paradisone on the other hand corresponds to the intensely aromatic and highly bioactive form (notably, it's the dihydro-derivative which is somewhat less active but more stable than natural JA) and is obviously the most expensive one too. This very active form corresponds also to the real natural isomer which, due its sterical hindrance and keto-enol tautomerism, tends to epimerise during isolation and storage to the usually described derivative 1R,2R-(-)-methyl dihydrojasmonate or in short (-)-methyl dihydrojasmonate (in case of essential oils and plant extracts, it would be (-)-jasmonic acid). In fact, many older studies on jasmonic acid and/or methyl jasmonate used a racemic mixture comprising mainly of the stable two trans-isomers; one of the reasons why Firmenich got so famous for Hedione and more so the newer versions which are the ones way more difficult to synthesise. The favoured form under common conditions is a roughly 5:95 ratio favouring the less or even inactive form. This means that many commercial products, although synthesised at a given ratio will be converted once in contact with water; Hedione is therefore often a mix of 10:90 (+/-)-cis- to (+/-)-trans-isomers.
Why the most active isomer in plants is also the one with the strongest odour, I do not know... maybe because it's the natural one?
Remains to be said that all isomers show some activities in certain tests, most of all the two naturally occurring 1R-enantiomers, usually have the same net effect, and will produce the same results just to varying degrees but the 1R,2R-epimer (may that be jasmonic acid or Paradisone) shows always the strongest activity. Notably, the methyl ester renders the molecule more active than the free acid but the lack the double bond in the pentyl side-chain greatly reduces it. Unfortunately, there is neither much data on dihydro-derivatives nor on the used enantiomers. Hence, different publications show, depending on the enantiopurity of the dihydro-derivative as much as that of the reference jasmonic acid (which are both usually not known nor cared about!), an activity of 10 to 50% or zero activity. Comparing the commonly used concentration of (-)-jasmonic acid (the less active enantiomer usually used) with that of JAZ Rose Spray (likely the 'degraded' racemate of methyl dihydrojasmonate) implies an activity of 0.1 to 1% of the latter.

(And here I cut some stuff out)

Email 2:
Forgot to mention:
1R,2S-(+)-epijasmonate is also termed 3R,7S-(+)-iso-jasmonate, depending on the used nomenclature .
As mentioned (and I'm sure you don't really remember, although this is the important part) the epijasmonates (resp. iso-jasmonates) transform into the trans-enantiomers. As the former are more active than the latter (though you find some publications which state the opposite but that's based on a mistake and has been copied several times...he even copied the mistake from himself and stated the opposite a page later...such an idiot... ) this means the following for the price/activity calculation:

1R,2S-(+)-Methyl dihydroepijasmonate (1) has full bioactivity and a very strong odour
1R,2R-(-)-Methyl dihydrojasmonate (2) has still some bioactivity and a moderate odour
1S,2R-(-)-Methyl dihydroepijasmonate (3) has a very weak activity but no odour
1S,2S-(+)-Methyl dihydrojasmonate (4) is usually bare of any activity and odour

It looks like if many results prior to 2007 are flawed as they assumed (-)-jasmonic acid to be the active form due the non-availability of (+)-iso-jasmonic acid and also traces of that on in the former (especially in tests using the really-really active isoleucine-adduct). That means, we don't know how active the four above substances really are ;( .
For the sake of simplicity (relative simplicity), I base bioactivity on odour intensity; in fact, it could well be that only compound 1 has an activity at all and the 10% of compound 2 are just the few percent which epimerised. Also, I ignore the 95:5 epimerisation ratio, feel free to calculate yourself :
1: 100% active
2: 10% active
3: 1% active
4: 0% active
That means, Hedione, the equal parts mix, has an activity or 27.5% (just after synthesis)
Hedione HC, the mix of 1 and 3 has about 50% activity
Paradisone (compound 1) has 100% activity

Now you buy that stuff, put it into solution, and get hit by the train called Murphy's Law... epimerisation occurs (the more water and the more pH deviates from 7, the faster) and product 1 slowly turns into product 2 and product 3 into 4.
Hedione becomes a mixture of 2 and 4, which has a total activity of 5%.
Hedione HC first turns into something like Hedione and then obviously into the same 5% mix as above.
Paradisone on the other hand slowly turns into a mix of 1 and 2 and finally becomes 2, or 10% activity.
Do the maths and you will see that with Hedione, you spend less and lose only 5 times whereas with Heidone HC you spend more and lose 10 times only to find yourself with the same stuff as if you had bought standard Hedione.
With Paradisone, you spend a lot of money only to lose 10 times but at least ending with something having 10% activity.

The logic conclusion is: buy compound 2 if it's not too expensive because that way you buy 10% activity and keep the 10% no matter what. Consistency or spraying every time the exact same thing is most important. Alternatively, go for Hedione as that one only loses 5 times, certainly contains an active ingredient (1) and isn't expensive .
But again, the % activity are a rough estimate and the pure compound 2 may not be active at all but only Paradisone!! Without proper testing (which hasn't been done), we'll never know...

(Again, I cut some stuff out)

Hope that helps and wasn't too much confusion... If so, don't worry, you aren't the only ones; so far, I found three papers (one done by Firmenich itself, one sponsored by Firmenich, and one written by one of the 'gods' of jasmonic acid chemistry and signalling, imagine that!) wherein they used the wrong stereochemical nomenclature, drew the wrong enantiomer, or mixed the biological activity up.

Thank you for the informative post. Is there anyway you could post attachments of those three papers? Thanks again.

 

[Only Ornamental]

... Is there anyway you could post attachments of those three papers?...

Why these three? As said, they're flawed... if you perceive reading such papers as funny, then you're an even worse science nerd than I am .
And no, I won't attach any papers as I'm not sure that they're open access. Besides, there are more recent ones regarding jasmonic acid (search pubmed or sciencedirect for review articles for example by Wasternack) and you'll easily find enough on Hedione and chirality yourself (for example first hit on google).
It's weird, but nearly every article states different ratios for the enantiomers and often enough, it's not referenced from where they got the results... maybe epimerisation occurred during storage, sample preparation, or analysis?

 

[plastochron]

Why these three? As said, they're flawed... if you perceive reading such papers as funny, then you're an even worse science nerd than I am .
And no, I won't attach any papers as I'm not sure that they're open access. Besides, there are more recent ones regarding jasmonic acid (search pubmed or sciencedirect for review articles for example by Wasternack) and you'll easily find enough on Hedione and chirality yourself (for example first hit on google).
It's weird, but nearly every article states different ratios for the enantiomers and often enough, it's not referenced from where they got the results... maybe epimerisation occurred during storage, sample preparation, or analysis?

I want to go through the exercise of picking out the mistakes in these publications using your logic. I find this method extremely helpful for improving/internalizing the understanding of highly technical information.

And you won't post the non-open access articles?!? where's the fun in that... if they were open access I could download them myself!

Anyways, my sincere gratitude for making a significant contribution to this discussion. Best explanation I have heard on the topic of bioactivity of jasmonates.

 

[Only Ornamental]

Ah, OK .
If I wanted to up- or download copyright protected material in order to aggravate my guilt over illegally growing certain things, I'd do that with torrents and not on my favourite cannabis forum where, astonishing as this may sound, such sort of behaviour is not tolerated and can result in banning. You of all people should know; if you have forgotten, check your visitor messages .

Now to the useful part:
- "The firmenich approach to aroma chemicals production" by Robert Weinstein, might be open access
- THIS one is likely not open access but you might find ways to get it anyway
- Can't find the third one though... wasn't worth keeping/remembering it.

 

[ghostmade]

I don't know If this has been discussed. But I've seen products make trichomes larger, producing more trichomes, will just say I take attorney try to come and make it big does it have the same thc content? Just say I turn 1 gram of resin glands in 2.dose the am I just building more wax on the resin gland or am I actually increase in the amount of THC in the overall product. Another words is making more or bigger resin glands dilute the potency of the THC present NSAID glands

 

[Only Ornamental]

As the gland heads contain mostly THC, having either more 'normal' looking or else bigger trichomes usually means you also have more THC.
The finding that JA increases trichomes is based on Arabidopsis thaliana (thale cress) where it mostly leads to stronger branching of the trichomes and a higher density of 'non-secretory' trichomes. In principle, this has nothing to do with cannabis trichomes...
But JA also increases the expression of several enzymes of the mevalonate and the MEP/DOXP pathways in different species. Both contribute to THCA synthesis and where there's more THC, there are bigger trichome heads.

 

[OldGuyInOregon]

Thanks to the authors for this info!

 

[little-soldier]

Just finished reading all 15 pages and I gotta say...thx for all the usefull information. Planning on eventually testing jaz rose spray from 350ppm all the way down to 25 ppm. Also from what I have understood i need to add GA3 too but in very low dosage if I dont want to get the foxtail on my plants. probably start at 1 ppm and work my way down to 0.25 ppm. Because the perfect ratio of MDHJ and GA3 = Even more cristals than just the MDHJ. Now combine all of these with some UVB in your growroom and KOOMBAYA.U got yourself a strain at its full potential. Oh and I read an article too about weed grown in colorado having a higher THC ratio.It is believed that weed grown in higher altitudes gets you higher

Now my question is wheres Spurr the tester? Its been 3 years since his last post.

 

[Sunfire]

I don't know If this has been discussed. But I've seen products make trichomes larger, producing more trichomes, will just say I take attorney try to come and make it big does it have the same thc content? Just say I turn 1 gram of resin glands in 2.dose the am I just building more wax on the resin gland or am I actually increase in the amount of THC in the overall product. Another words is making more or bigger resin glands dilute the potency of the THC present NSAID glands

I'm skeptical as well.

just assuming that the trich heads are mostly full of oleo Resins is silly. Ghost might be looking at this from a perspective that extractions has given him, as well as myself.

the trich heads could just have a thicker coating of wax. I believe it's actually the wax that's keeps bugs off and the thc that keeps larger animals from eating the plant and getting intoxicated. I have heard for over a decade people's different methods of purposely stressing plants for better results. This could be explained with JA. I also think y here might be something to people big leafing their outdoor on the stalks 2 weeks before harvest. As far as I know this method was to save time, but now people, even indoor, are saying de-foliation 2 weeks before harvest produces a higher grade smoke. Could that be a reaction of increased thc production from stimulating animals eating it??? I've always noticed my volunteers around the property that I usually do nothing but water every now and then, are great smoke! They get munched on by deer and rabbits and bugs, never get to be more than 2 pounds or so and doesn't look too frosty but it tastes great and gets you high as all mighty!

Anyways, I think analytical testing it's need to be done on the control plants and the test subjects. If thc is the same on the Jaz spray plant and the control, then the more and larger trichs is just more wax. I also think of I at as fruit trees can only produce so much brix. More fruit means they are less sweeter. More trichs might mean they are less thc filled.

anyways, I havnt read y he whole thread yet, just wanted to tag it and come back later when I have a few hours to go through all the links. I found this by starting at looking into aspirin for plants and someone said JA is natural and works better to stimulate deffense. This might have already been answered so please forgive me if so...can JA be sprayed In veg. To increase immunity and self deffense? Will it cone at a cost of the growth?

I can't help but feel that the plant has evolved for a long time. I think they can do their best if we don't try to play god with them. "The more you fuck with them the better they don't get"? I still want to try this stuff out though, especially for immune boosting of sickly plants. Anyone help me on that thought? I'll come back and read y he whole thing later.

 

[Bongstar420]

I want to increase trichome production on my buds. To this end I read several studies available on the internet. From a study entitled “Interactive effects of jasmonic acid, salicylic acid, and gibberellin on induction of trichomes in Arabidopsis” by Traw and Bergelson, I learned that that, “…gibberellin and jasmonic acid had a synergistic effect on the induction of trichomes, suggesting important interactions between these two compounds.”
http://www.citeulike.org/group/2438/article/853395

From this PGRs thread, I leaned that a good economical source of jasmonic acid was Jaz Rose Spray (thank you Spurr). I already had some gibberellic acid that I bought a while back. Now I had everything to start my experiment.

The strain I used were six Bubblicious from Nirvana in their fourth week of flower, all in the same cabinet. I broke them into three groups. With two, I did nothing, Two others I removed from the cabinet and administered a spraying of Jaz Rose Spray (jasmonic acid). And the last two I removed from the cabinet and administered a dose of Jaz Rose Spray and gibberellic acid, as described by Traw and Bergelson. After the four plants had dried, I returned them to the cabinet.

Ten days later this is what I see:

The plants that received no treatment are progressing as Bubblicious always does, with light visible trichs on the buds, but very little frosting on the sugar leaves.

The plants that received jasmonic acid treatment only, show heavy visible trichs on the buds, as well as a light frosting of trichomes on the sugar leaves.

The plants that received the mix of jasmonic acid and gibberellic acid also show heavy visible trichs on the buds, a light frosting of trichomes on the sugar leaves AND a great deal of FOXTAILING. Foxtailing is considered a disagreeable trait by most gardeners.

Because of my strong attachment to my freedom, and a lack of technical prowess, I will not be posting any pics.

I hope this provides fodder for people more expert than me to examine more carefully the effect of jasmonic acid on trichome production.

You are on the right path, but be forewarned. Jasomonic acid is supposed to reduce biomass yield and the last time I looked you don't get a 60% higher price to make up for the 30% reduction in total weight (also no point to sprays that don't add profits).