Myristicin structure

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... 

Acid-catalyzed hydrolysis of echitoserpidine gave an indolenine (22) and an aromatic acid identical with myristicinic acid (38). Reduction of the indolenine with sodium borohydride gave an indole derivative identified as 39. Methanolysis of echitoserpidine gave an anilinoacrylate derivative showing a molecular ion at 354 mu and a base peak at m/e 140. This compound was identical to (—)-minovincinine (13). Echitoserpidine therefore has structure 35 (25). 

Myristicin is found in nutmeg and mace—Myristica fragrans (Myristicaceae). It also occurs in black pepper, carrot, parsley and dill. Myristicin is structurally related to safrol and is toxic in high doses. Nutmeg itself exhibits narcotic and intoxicating properties, though it does have medicinal uses in lower doses (Hall 1973). 

Other groups of substances have been noted, but further investigation is needed to ascertain their identification among the surest ones, we would mention plastoquinones with a structure close to that of vitamin Ki, detected in chloroplasts (Kegel, 1962) and in olive oil (Therrault, 1963) a group of phenolic substances, whose presence has been observed in at least two oils [in parsley oil, the myristicin (Privett et al., 1963), and in olive oil, the oleoeuropein (Vazquez Romero et al., 1961)] and the vinylic esters and esters of diols (propane-1,2- and 1,3-diol, butane-1,3- and 1,4-diol) these last are found in corn seeds and consequently in the oil also (Bergelson et al., 1966). 

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