Non-isoprenoid

Kozubek, A., Tyman, J. Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biological activity. Chemical Reviews, Vol.99, No.l. Qanuary 1999), pp. 1-31, ISSN 0009-2665... 

Non-isoprenoid Tryptamines.—Tryptamine and Nb-methyltryptamine have been shown to be present in the inflorescences of Tachigalia paniculata (Family... 

Si4.6 whereas a silicon-based approach proved to be successful and gave the required exocyclic double bond in (3-Gorgonene, a non-isoprenoid sesquiterpene isolated from Pseudopteragorgia americana. The success of the a-silyl carbanion here is attributed to the lengthy carbon-silicon bond which makes the carbanion sterically less demanding. 

The syntheses described above and the individual reaction steps, respectively, are the historical basis for the development of the synthesis of isoprenoid juvenile hormones. In addition to the latter, a great number of naturally occurring or synthetic analogous substances as well as non-isoprenoid compounds with juvenile hormone activity can also be obtained via Wittig reaction. However, since these syntheses do not offer basically new aspects with respect to the olefination step, they are not further discussed here. 

Non-isoprenoid Tryptamines.—The structures (21) and (22) have been deduced for donaxarine and donaxaridine, the alkaloids of Arundo donax 14 the relationship between the two is confirmed by the formation of donaxarine by condensation of... 

Dimethylethylcydohexanes.—Two new halogenated monoterpenoids are violacene (150) from Plocamium violaceum,250 a 1,4-dimethyl-1-ethylcyclohexane which can be rationalized biosynthetically from the cyclization of an acyclic precursor via a bromonium ion, and plocamene B (151), again from Plocamium violaceum, which may be the first member of a series of non-isoprenoid monoterpenoids from this species.251... 

J.H.P. Tyman, Non-isoprenoid Phenolic Lipids, in Studies in Natural Products Chemistry, Ed. Atta-ur-Rahman, Elsevier, Amsterdam, Vol.9, p.313. 

Non-isoprenoid Tryptamines.—The tryptamide (6) of an aminoethylthiazole carboxylic acid has been isolated from a Thermoactinomyces species (strain TM-64). 

Carotenoids.—number of excellent reviews on carotenoids have appeared, based on the main lectures given at the 4th International Symposium on Carotenoids, at Basle, Switzerland. They include reviews on new carotenoid structures, syntheses of carotenoids and related polyenes (including new routes to tunaxanthin and lutein, and various industrial syntheses of vitamin A and related carotenoids. Wittig reactions have been used in the synthesis of a non-isoprenoid ether pigment, including condensations with the phosphonium salts (77) and (78). 

Non-Isoprenoid Monoterpenoids.—There has been activity in the field of monoterpenoids formally related to chrysanthemic acid (43) and belonging to the odd artemesyl (44), santolenyl (45), and lavandulyl (46) groups where the customary head-to-tail linkage of isoprene units is not followed. Yomogi alcohol (47), the allylically rearranged artemisia alcohol (51), has been isolated from Artemisia feddei. The santolinyl class now includes two alcohols. 

This chapter focuses on the use of different methods for isolation of alkylresorcinols. Alkylresorcinols are members of a lipid group called non-isoprenoid phenolic lipids. Different aspects of the extraction by classical methods and supercritical CO2 are discussed. Supercritical CO2 extraction of alkylresorcinols from rye bran is discussed for the first time. As compared to the classical extraction methods, supercritical CO2 gives higher yields and it allows the separation of the crude extrac into long- and short-chain alkylresorcinol homologues. 

For resorcinolic lipids, particularly those with long saturated side-chains, the use of polar solvents is important due to their amphiphilicity. The crude extracts in many cases are subjected to preliminary fractionation/purification either by solvent fractionation/partition or by application of chromatography. For prepurification of the material and its separation from polymerized phenolics, gel filtration on hydrophobic Sephadex or TSK gel is sometimes used. Silica gel is most frequently employed for the separation and/or purification of resorcinolic lipids, notably in some studies with Ononis species (12-14). The array of compounds reported appears partly attributable to methylation or acetylation reactions occurring during column chromatographic separation. An interesting approach for I the pre-purification and selective separation of resorcinolic lipid from phenolic lipids or resorcinolic lipids from impurities has recently been reported. A selective partitioning of different non-isoprenoid phenolic lipids... 

ABSTRACT This review is concerned with non-isoprenoid phenolic lipids typified by compounds biosynthesised by the polyketide pathway. Botanical, biological and entomological sources of such phenolic lipids are described which contain monohydric phenols, notably cardanol and relatives, dihydric phenols such as cardols, alk(en)ylresorcinols,urushiols and phenolic acids, particularly anacardic acids. Some recently investigated mixed types of dihydric phenolic lipids are included. Separatory methods are briefly reviewed. Synthetic methods for the saturated and unsaturated members of the three main classes of interest in structure/activity studies are summarised. Biological properties of members of the three main classes are given and discussed. 

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