Myristicin

MYRISTICIN In moderate amounts in dill, carrot, celery, fennel, mace and nutmeg (no more than 10% tops). Makes up about 40% of the oil of parsnip and can reach up to 50-60% of the oil of parsley leaves and seeds. Give nutmeg a rest folks It just don t have it when compared to parsley and parsnip. 

The synthesis of MMDA in Pihkal is one of the longest and most tedious in the book. If one is going the route via myristicin, the Sisifos work of isolating the tiny amount of essential oil present in nutmeg, followed by fractional distillation to purify the myristicin fraction is also added to the labor of the poor chemist. Therefore I propose a new route to this "essential amphetamine". 

The synthesis of meconin has been referred to already (p. 201). Cotarnine has been synthesised by Salway from myristicin (I) as a starting-point. This was transformed into jS-3-methoxy-4 5-methylenedioxy-phenylpropionic acid (II), the amide of which was converted by Hofmann s reaction into )S-3-methoxy-4 5-methylenedioxyphenylethylamine, and the phenylacetyl derivative (HI) of this condensed, by heating it in xylene solution with phosphoric oxide, giving rise to the two possible dihydroiso-quinoline derivatives. The first of these substances, 8-methoxy-6 7-methylenedipxy-1-benzyl-3 4-dihydroiioquinoline (IV), on conversion into the methochloride and reduction with tin and hydrochloric acid, gave... 

Myristicin, CjjHjgOg, is 4-allyl-6-methoxy-l. 2-methylenedioxybenzene. It is found in oil of nutmeg and in parsley oil. It is a fragrant compound having the following characters —... 

Myristicin and isomyristicin are distinguished by their reactions with bromine. Myristicin, when treated with two atoms of bromine, yields an oily liquid, whilst isomyristicin yields a crystalline body melting at 109°. If the isomers are dissolved in acetic acid, and treated with bromine until no more is absorbed, the mixture being kept cold all the time, the following compounds are obtained —... 

The edible parts of parsnips contain a chemical of insecticidal and strong synergistic nature. This chemical, present in a concentration of about 200 p.p.m., was isolated and identified as 5-allyl-l-methoxy -2, 3-methylene-dioxybenzene or myristicin. Its toxicity to various insects (fruit flies, etc.) was established and compared with pyrethrum and aldrin. A second chemical, identified as 2-phenylethyl isothiocyanate, was found in the edible parts of turnips and rutabaga, which also have been consumed for centuries by humans without obvious harm. 

Insecticide Fliesa None Myristicin Piperonyl butoxide ... 

Tenerife and La Palma, revealed the existence of luteolin and an array of simple phenolic derivatives as well as three known phytosterols, B-amyrin, sitosterol, and stigmasterol. The phenols identified comprised a set of phenylpropanoids myristicin [566] (see Fig. 6.16 for structures 566-573), methyleugenol [567], todadiol [568], todatriol [569], crocatone [570], elemicin [571], apiole [572], and the coumarin scopoletin [573]. The occurrence of these compounds is recorded in Table 6.5. The differences between the two profiles were taken by Gonzalez and his co-workers... 

Nutmeg Myristica fragrans Tree Myristicin Elemicin... 

This is the most efficient way to get myristicin from nutmeg. 

Increased Concentration of Myristicin and 6-Methoxymellein in Carrot Root upon Irradiation... 

Myristicin has not been reported to possess antifungal activity, and therefore is not a phytoalexin according to the standard interpretation of this term (1 ). It does, however, potentiate the activity of the insecticide, paraoxon, in flies by inhibiting its degradation (2), and may in similar manner potentiate the action of phytoalexins of carrot root (falcarinol, falcarindiol,... 

Results of Wulf et al (7) show that carrot roots obtained from a supermarket contain myristicin Imperator variety carrots contain an average of 15 parts per million (ppm). Recently harvested, unprocessed carrots only rarely contain myristicin (8). The presence of myristicin in supermarket carrots and its absence in recently harvested ones indicate that its increased concentration may have been induced by some elicitor following harvest. Solar radiation after harvest, or fluorescent lighting during display, may function as such an elicitor. Light is known to produce ethylene and is an activator of phenylalanine ammonia-lyase, one of the regulatory enzymes responsible for phenylpropanoid biosynthesis in plants (9). 

In the following experiments carrot roots were exposed to various sources of ultraviolet light in the laboratory and set aside to allow time for enzyme synthesis. Following this period, changes in myristicin and phytoalexin levels were measured. All of these components of carrot root are measured in one assay. Myristicin and 6-methoxymellein concentrations increased in some samples after irradiation with ultraviolet light falcarinol and falcarindiol concentration changes did not appear to be related to the ultraviolet light used in this study. 

A four-year study of field-grown commercial carrot roots revealed that recently harvested, unprocessed carrot roots contained 24 ppm falcarinol and 65 ppm falcarindiol (8). 6-Methoxymellein (6-MM) had not been identified by Yates al (8) at that time, and was not measured in that study. Reexamination of data revealed that 6-MM was absent from most samples, but present in a few at concentrations of 2 to 8 ppm. Myristicin, 1 ppm, was detected in only one sample. Wulf et 1978, reported that myristicin was present in supermarket carrots. Other studies have shown that certain brands of supermarket carrots contain myristicin while others do not (Yates, unpub.). The presence of myristicin in some samples from the supermarket and its absence in unprocessed carrots analyzed as soon after harvest as possible suggests that myristicin formation is induced during some stage of processing. Since light is known to be an elicitor of a plant system that results in the synthesis of phenylpropanoid compounds, a study of the effect of light on harvested carrot roots was undertaken. 

Preliminary experiments, using a container with reflective surfaces, employed light from eight fluorescent bulbs that produced a preponderance of radiation at 310 nm. Myristicin increased in samples that were irradiated 1 h and then kept for a 24-h induction period. However, heat produced by this system and the resulting dehydration of carrot roots may have affected results. Later experiments, employing a Chromato-Vue box used for ultraviolet examination of TLC plates, avoided these problems. One-hour light... 

Table I. ( Changes in Carrot Root Myristicin Irradiated One Hour with Ultraviolet Light and 6-Methoxymellein ...

Brand or Variety Beginning (mg) 3 Myristicin Concentration 3 6-Methoxymellein Concentration ... 

Myristicin content of some carrot samples was increased two-to five-fold over nonirradiated controls (Table I). The increase in concentration of myristicin is presumed to be via the phenylpropanoid pathway phenylalanine ammonia-lyase, an enzyme of that system, is activated by light (9). Failure of some samples exposed to UV light to synthesize myristicin may be due to the absence or inhibition of a key enzyme needed for myristicin synthesis. 

Falcarinol and falcarindiol concentration changes are small compared to those in myristicin and 6-MM content, and do not appear related to radiation (Table II). These polyacetylenes are present in fresh carrots. Immediately upon wounding, they are translocated to the surface through oil ducts (3 ) > and, therefore, their function as phytoalexins apparently does not depend upon novo synthesis. 

Although myristicin is not considered to be an antifungal agent, an increase in myristicin concentration in some carrot roots upon exposure to UV radiation indicates that it may have some protective function. 

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