Sciencemadness Discussion Board

Amygdalin from Apple Seeds [ EXPERIMENTS AND RESULTS]

Backyard Chemist - 2-1-2015 at 20:29

Yesterday I conducted an experiment involving the extraction of amygdalin from apple seeds.

The seeds were ground up into a fine powder and mixed with maple syrop. I wanted to see if I truly had amygdalin so I got myself test subjects- ants. Amygdalin is converted into hydrogen cyanide when it makes contact with stomach acids. I had a control setup and an experimental setup. The control setup consisted of one ant with a drop of maple syrop- no finely powdered apple seeds added. The experimental setup consisted of one ant with a drop of syrop mixed with finely powdered apple seeds. Long story short- The ant in the experimental setup had died while the any in the control setup did not. I need verification! Was amygdalin in the apple seeds truly responsible for the death of the ant? Can someone give me a detailed description as to what happened? Thanks!

[Edited on 3-1-2015 by Backyard Chemist]

j_sum1 - 3-1-2015 at 02:45

You had two ants and one died. I am not sure that it is possible to draw too strong a conclusion from that.

CHRIS25 - 3-1-2015 at 03:00

Not that I would ever touch anything like this - but to avoid chemicals and experimentation with such things I would take 8 ants. 3 in one bottle with the crushed seeds, then 1 each in seperate bottle with crushed seeds, and 1 ant in the harmless environment and one with uncrushed apple seeds. If 6 died then I am pretty sure this would be conclusive.

[Edited on 3-1-2015 by CHRIS25]

Bert - 3-1-2015 at 07:04

Quote:
Yesterday I conducted an experiment involving the extraction of amygdalin from apple seeds.

The seeds were ground up into a fine powder and mixed with maple syrop. I wanted to see if I truly had amygdalin so I got myself test subjects- ants. Amygdalin is converted into hydrogen cyanide when it makes contact with stomach acids.


Where did you "extract amygdalin". You describe grinding apple seeds and mixing the whole lot with maple SYRUP, not performing an extraction.

You seem confused about how cyanide might be released from amygdalin. It's released by an enzyme in the small intestine, in the case of humans.

Do your test animals even have a similarly active enzymes in their digestive systems?

Did you have a large enough number of test animals to draw a conclusion with a high degree of confidence?



aga - 3-1-2015 at 11:50

Wiki refers to amygdalin being extracted from apricot seeds or almonds using hot ethanol and precipitating crystals using diethyl ether.

Sounds like a job for a Soxhlet.

Backyard Chemist - 3-1-2015 at 12:25

What's the name of the enzyme in the small intestine responsible for converting amygdalin into HCN?

aga - 3-1-2015 at 12:32

β-glucosidase in Hampsters.

Dunno about humans.

http://www.sciencedirect.com/science/article/pii/02786915869...

HgDinis25 - 3-1-2015 at 12:37

The acid in animal's stomach is Hydrochloric Acid (unless ants are special). Amygdalin reacts with HCl to produce Mandelic Acid, D-Glucose and Ammonia, according to wikipedia.

The Wikipedia page also has a good explanation on how Amygdalin breaks down in our bodies and the enzymes responsable.

And why on earth did you add the seeds to maple syrop?

Wikipedia page: http://en.wikipedia.org/wiki/Amygdalin

Backyard Chemist - 3-1-2015 at 12:50

So the ants would consume the sugar along with the crushed seeds..
I needed something to lure them.



[Edited on 3-1-2015 by Backyard Chemist]

aga - 3-1-2015 at 13:32

I think i'll try the extraction using almonds this summer (plenty of almond trees hereabouts).

Can't imagine testing it on Ants though.

I like ants.

Bert - 3-1-2015 at 17:39

Apparently, enzymes released by physical damage to cells of the plants that store these glycosides (insect damage!) can split the CN group off of the stored cyanogenic glycosides, producing an insecticidal effect... Go ahead and eat the apple's fruit, worms. But leave the seeds alone!

http://en.m.wikipedia.org/wiki/Glycoside
Quote:

Cyanogenic glycosides

Amygdalin

In this case, the aglycone contains a cyanide group. All of these plants have these glycosides stored in the vacuole, but, if the plant is attacked, they are released and become activated by enzymes in the cytoplasm. These remove the sugar part of the molecule and release toxic hydrogen cyanide. Storing them in inactive forms in the vacuole prevents them from damaging the plant under normal conditions. An example of these is amygdalin from almonds. They can also be found in the fruits (and wilting leaves) of the rose family (including cherries, apples, plums, almonds, peaches, apricots, raspberries, and crabapples). Cassava, an important food plant in Africa and South America, contains cyanogenic glycosides and, therefore, has to be washed and ground under running water prior to consumption. Sorghum (Sorghum bicolor) expresses cyanogenic glycosides in its roots, and thus is resistant to pests such as rootworms (Diabrotica spp.) that plague its cousin maize (Zea mays L.). It was once thought that cyanogenic glycosides might have anti-cancer properties, but this idea was disproven (see Amygdalin). A recent study may also show that increasing CO 2 levels may result in much higher levels of cyanogenic glycoside production in sorghum and cassava plants, making them highly toxic and inconsumable. A doubling of CO 2 concentration was found to double the concentration of cyanogenic glycosides in the leaves.[5][6] Dhurrin, linamarin, lotaustralin, and prunasin are also classified as cyanogenic glycosides.



[Edited on 4-1-2015 by Bert]

Random - 3-1-2015 at 18:09

It's not a big amount anyway. Hard to judge crushed apple seeds. Purified stuff is potent as is HCN itself.

Backyard Chemist - 3-1-2015 at 20:09

Is amygdalin better to extract from apple seeds or bitter almonds? Does it even matter?

MrHomeScientist - 5-1-2015 at 10:12

Bert's points are all very valid, and applicable for all basic science. One test subject doesn't really tell you anything. Maybe that ant was about to die anyway from disease or old age. With any experiment, you need a large enough sample size to make claims with any validity. I see this mistake made all the time when judging school science fairs!

Brain&Force - 5-1-2015 at 10:17

Quote: Originally posted by MrHomeScientist  
I see this mistake made all the time when judging school science fairs!


You judge science fairs?

Crap, I should have asked you for more advice when starting my project...

MrHomeScientist - 5-1-2015 at 11:47

Yep, usually middle school and occasionally high school. After doing it for several years I've noticed people seem to think that if their project involves a liquid, it must be chemistry!

Based on the quality of your posts and very interesting projects, I'd say you're already well ahead of the curve. But I'd be happy to answer any questions you might have (as long as you don't mind the answers coming from experience judging a younger crowd).

Amygdalin fun

Yugen - 6-1-2015 at 08:52

Quote: Originally posted by Backyard Chemist  
Is amygdalin better to extract from apple seeds or bitter almonds? Does it even matter?


It totally matters, Check this source out for example.

If you want to have some fun with amygdalin you should play with almond enzymes (aka Emulsin). You will be able to smell your results rather than watch animals die. :D Check out page 509 of this book that I've uploaded (the Salicin experiment works for amygdalin too).

Attachment: Practical Organic Chemistry 1979.pdf (9.1MB)
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