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    The Etymology And Drugs Of Parsley
    By Enrico Uva | June 9th 2011 06:14 PM | 14 comments | Print | E-mail | Track Comments
    About Enrico

    I majored in chemistry, worked briefly in the food industry and at Fisheries and Oceans. I then obtained a degree in education. Since then I have...

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    My first language is a rough southern Italian dialect, scorned by many Northerners. But what I like about my mother tongue is the connection between some of its vocabulary and Linnaean taxonomy.

    Parsley for instance is known as  prezzemolo in standard Italian, but I grew up calling it petrosino. Interestingly parsley's genus, derived from Latin, is Petroselinum. The modern Italian word also originates from Petroselinum, but obviously the dialect-version of parsley is closer to its roots, pardon the pun. The English word seems to have been influenced by the Old French peresil and by the old English petersilie, which in turn is an offshoot of the Latin.

    The Greeks once referred to the herb as petroselinon, which meant "rock celery", but the modern Greek word is based on the Turkish word maydanoz.

    Petroselinum latifolium  photo by Forest and Kim Starr

    Petroselinum latifolium; credit Forest&Kim Starr


    Now that we know parsley's etymology, we can investigate its chemistry. Simple distillation equipment may be fine for creating moonshine, but it will not do much to separate the compounds of parsley or of any plant for that matter. What's needed is the Likens Nickerson Method. The parsley-water mixture is placed in one flask, and a separate flask holds an organic solvent. Both are boiled while being connected to a shared set of columns and condenser. Using dry ice, water is removed from the fractions, and eventually the compounds are separated and identified through good-old gas chromatography-mass spectrometry.

    The main volatile component of oils in parsley is apiole (also spelled apiol), C12H14O4 .

    All sorts of medicinal properties have been attributed to apiole since the mid-19th century, but in concentrated form it can do a number on your kidneys and liver.
    The apiole molecule bears a strong resemblance to another substance found in small quantities in parsley: myristicin.



    Myristicin is the notorious alkaloid drug which is also found in nutmeg. In the latter, it is found in a greater percentage and coexists with other natural drugs. In the 1970's pursuit of altered states inspired many inmates to ingest spoonfuls of the spice. Possible side-reactions include chemotherapy-like vomiting and possibly death, a somewhat high price for hallucinations.


    As we compare the structure of parsley's non-psychoactive apiole to that of myristicin, we notice that one of the methoxy(O-CH3)groups is also replaced with hydrogen.


    As is often pointed out in the literature, myrisiticin, although not an alkaloid, is structurally very similar to peyote's hallucinogen, mescaline. Rather than being part of separate methoxy groups, the oxygens in myristicin form a heterocyclic ring, and in mescaline, the allylic group is in a reduced state and the tail-end carbon is replaced with an amino group.

    The similarities in natural products are not coincidences. In their bio-synthesis, they share a common pathway. Side-reactions then occur for various reasons, and they are subject to natural selection.


    Molecules, like words, often have common roots, but they are in a constant state of flux.



    Sources
    • http://www.uni-graz.at/~katzer/engl/Petr_cri.html
    • The Merck Index. Twelfth Edition
    • Pol. J. Food Nutr. Sci. 2005, Vol. 14/55,No 1, pp. 63–66

    Comments

    vongehr
    Nutmeg is extremely seldom taken at the high dosages needed for hallucinations, and if so, mostly puked out before it can do harm. At common dosages (1/4 nut) it is a fine anti-depressant. The only "problem" is that it should be ingested very early in the morning because it needs a few hours to start acting and then stays for ~12h. Your pointing out death and mayhem belongs to the usual scare mongering that feeds irrational fears and misunderstanding. Science2.0 should aim instead for education that balances such.
    The myristicin-mescaline connection is interesting. If there are common pathways, lets genetically engineer the nutmeg plant to make mescaline; peyote buttons grow too slowly. More citizen science projects to add to the ephedra-methamphetamine project, he he.
    On the Likens Nickerson Method: Maybe you can explain to us why it is such a complicated setup. Why the organic solvent has to boil, too?
     
    UvaE
    Your pointing out death and mayhem belongs to the usual scare mongering that feeds irrational fears and misunderstanding.
    The prisoner story is documented, but unfortunately it's from memory of a journal I read in university about 30 years ago! Your complaint is justified.
    On the Likens Nickerson Method: Maybe you can explain to us why it is such a complicated setup. Why the organic solvent has to boil, too?
    Many plant constituents are not water soluble, so they are extracted with a non-polar solvent (the "organic" solvent.) Unfortunately although I have plenty of hands-on experience with coventional distillation apparatus, i have none with the far more interesting Likens Nickerson apparatus. But it's on my must-do list--- if i can get back into university...there might be room for a young mind within an old body!
    rholley
    southern Italian dialect
    When I was reading Dante in the early nineties, there was in our university library a title that was, as I remember it,

    La Cummegia nel dialogo Barese.


    Alas, it seems to have gone now, so I can’t check how accurate my memory is.
    Robert H. Olley / Quondam Physics Department / University of Reading / England
    UvaE
    Barese is an interesting dialect--- my dad's neighbours were Barese, and it was at times challenging for me to pick up what they were saying . One of my 14 uncles decided to talk to me about Dante but only after his larynx was lost to cancer. Unfortunately i had a very hard time understanding-- not his dialect-- but the sound of his prosthetic device.
    rholley
    Barese is an interesting dialect
    At the other end of Italy, have you ever come across Triestin?  I encountered it when visiting Elettra (The Elettra Experience).
    Robert H. Olley / Quondam Physics Department / University of Reading / England
    UvaE
    Yes I have heard people speak it; in fact, many years ago I was surprised by the various dialects of the North...by the way, my memory played tricks on me: Alda's roots were in Abruzzi, not Bari, but my dad's nighbour was definitely Barese!
    Bonny Bonobo alias Brat
    That's funny, I also had one of many uncles who often wanted to talk to me about Dante and who also gave me an extremely valuable limited edition Dante book. I feel terrible looking back, I just humoured him and even pretended I knew what he was talking about and I still haven't read the book. Yet another thing to put on the 'to do' list.
    My latest forum article 'Australian Researchers Discover Potential Blue Green Algae Cause & Treatment of Motor Neuron Disease (MND)&(ALS)' Parkinsons's and Alzheimer's can be found at http://www.science20.com/forums/medicine
    UvaE
    To uncles (and parents!) out there: get teenagers books by Stephen Jay Gould, James Watson, Jacob Bronowski, Steven Weinberg, Penny LeCouteur, Paul Davies, David Bodanis, P.W. Atkins.... and kids, don't get a guilty complex like Helen did. Actually read them! :)
    rholley
    Quick aside:

    Have you seen this?  Murder Mystery Grows: Viruses Attack Healthy Bees, Too about Colony Collapse Disorder.

    I’ve updated my Bees and Bugs picture gallery, also.
    Robert H. Olley / Quondam Physics Department / University of Reading / England
    Bonny Bonobo alias Brat
    Yes, very interesting Robert.
    My latest forum article 'Australian Researchers Discover Potential Blue Green Algae Cause & Treatment of Motor Neuron Disease (MND)&(ALS)' Parkinsons's and Alzheimer's can be found at http://www.science20.com/forums/medicine
    rholley
    Science reading for teenagers!

    I was one of that species between 1958 and 1965.  In those days, my access was largely limited to what  was available in the local libraries, some of it pre-WW2.  So you might consider me to be like a creature that still retains some features from the Jurassic.

    However, what I did read gave me an insight that I did not get from doing science at School.  One of these books was Fred Hoyle’s Frontiers of Astronomy, which presented his new, and basically correct, theory of the formation of red giant stars.  This was absent from my 1952 edition of Norton’s Star Atlas.  Nevertheless, I did learn a lot from the latter, such as the use of bolometry to measure planetary temperatures.

    Another book was a textbook of chemistry by Linus Pauling.  That really bolstered my interest and understanding of chemistry.

    The third I will mention is a book of home experiments.  One positive was the use of manganese dioxide extracted from an old battery, and hydrogen peroxide, to make a propellant. Memory of that enabled me to develop one of the reactions on which a large part of my career depended.  The negative was an experiment involving an egg and strong saline solution, with a title like ‘Osmosis helps life to carry on’.  Nothing wrong with the thing itself, but it left me with that feeling of mystification which has always been in hindrance to my understanding later on.

    The thing that really put a block on my wider science reading was, alas, too much science fiction!



    One question, though: some of those authors you mention are unfamiliar to me.  Why those in particular?
    Robert H. Olley / Quondam Physics Department / University of Reading / England
    UvaE
    One positive was the use of manganese dioxide extracted from an old battery, and hydrogen peroxide, to make a propellant.
    I recall extracting MnO2 from a battery in my parents' garage, adding peroxide and then using a lit broom straw to test for oxygen. The latter was not the best material for a glowing splint test!
    One question, though: some of those authors you mention are unfamiliar to me. Why those in particular?
    They all write well, and their works are available in most Jurassic public libraries.
    As we compare the structure of parsley's non-psychoactive apiole to that of myristicin, we notice that the allylic group is in a different position on the aromatic ring. One of the methoxy(O-CH3)groups is also replaced with hydrogen.

    No, it isn't. You've just turned the drawing upside down. The two positions are equivalent in apiole. The only difference - to my eye - between apiole and myristicine is the removal of the methoxygroup.

    UvaE
    You're right. The error has been fixed in both the text and structure.
    And it also makes more sense now from a biosynthetic point of view. thanks