Terpenoids, chemical nature

Dev, S. (1989). Terpenoids. In Natural Products of Woody Plants II Chemicals Extraneous to the Lignocellulosic Cell Wall, ed. Rowe, J.W., Springer-Verlag, Berlin, pp. 691 807. 

Major volatile oils have been divided into two groups. Those oils containing principally chemicals which are terpenoid in nature and which are derived by the deoxyxylulose phosphate pathway are given in Table 5.1 below. Oils which are composed predominantly of aromatic compounds which are derived via the shikimate pathway are listed in Table 4.1 on page 139. The introductory remarks to Table 4.1 are also applicable to Table 5.1. 

In the early tobacco and tobacco smoke studies, the chemical nature of one or two components was defined by means of classical chemical procedures and described in an appropriate publication, for example, the identification of the previously discussed terpenoid alcohol solanesol in flue-cured tobacco (3359), the phenols eugenol and isoeugenol identified in the mainstream smoke (MSS) from Oriental tobacco (3280), and... 

Using a simple five carbon building block, nature creates an array of terpenoid chemicals with an infinite variety of structural variation and vast range of biological functions. Such a cornucopia cannot but leave the terpene chemist feeling as Newton did. 

Implicit ia the base names are the absolute configurations at carbons 8 and 12 and the iadicated numbering systems. Derivatives of these parent stmctures are named according to terpene and steroid nomenclature rules (see Steroids Terpenoids). The lengthy and awkward nature of the chemical abstract systematic nomenclature (12) for these compounds has resulted ia the development (13) and use of simplified nomenclature based on common names. 

Isoprenoids or terpenoids are a large class of naturally occurring organic compounds with tremendous chemical and structural diversity. They are organic materials produced in the HMG-CoA (3-hydroxy-3-methyl-glutaryl-CoA) reductase pathway... 

Figure 12.4 The molecular structure of a taxane [114]. Taxotere is the semi-synthetic congener of Taxol. (Reproduced by permission from Macmillan Publishers Ltd Susan C. Roberts. Production and engineering of terpenoids in plant cell culture. Nature Chemical Biology 3 (7) 387-395. London Nature Publishing Group. 2007 Macmillan)...

Roberts, S. C. (2007) Production and engineering of terpenoids in plant cell culture. Nature Chemical Biology, 3,... 

Chang, M.C.Y., Eachus, R.A., Trieu, W. et al. (2007) Engineering Escherichia coli for production of functionalized terpenoids using plant P450s. Nature Chemical Biology, 3, 274—277. 

A recent example demonstrates that corals rely on induced biosynthesis of terpenes as a dynamic defense strategy as well. The induction of terpenoid secondary metabolites was observed in the sea whip Pseudopterogorgia elisabethae [162]. Levels of pseudopterosins 89-92, a group of diterpene glycosides with anti-inflammatory and analgesic properties (Scheme 23) [163-165], are increased in response predation by the mollusk Cyphoma gibbosum. First bioassays indicate that these natural products are involved in the chemical defense. 

From a chemical point of view, vegetable resins are a complex mixture of mono-, sesqui-, di- and triterpenes, which have, respectively, 10, 15, 20 and 30 carbon atoms per molecule. The mono- and sesquiterpenes are both present in most resins. The di- and triterpenes are rarely found together in the same resin, which means that terpenic resins can be divided into two main classes. Table 1.5 lists the botanical origin and the kind of terpenoid compounds of some natural resins. 

P-parinaric acid, physical properties, 5 33t P-pentenoic acid, physical properties, 5 3 It P-peroxylactones, 18 484 Beta phase titanium, 24 838 in alloys, 24 854-856 properties of, 24 840, 941 P-phellandrene, 24 493 P-picoline, 21 110 from acrolein, 1 276 uses for, 21 120 P-pinene, 3 230 24 496-497 major products from, 24 478 /-menthol from, 24 522 as natural precursor for aroma chemicals, 3 232 terpenoids from, 24 478-479 P-propiolactone, polymerization of, 14 259 P-quartz solid solution, 12 637—638 Beta ratio, in filtration, 11 329—330 Beta (P) rays, 21 285 P-scission reactions, 14 280-281 P-skytanthine, 2 101 P-spodumene solid solution, 12 638-639 P-sulfur trioxide, 23 756 P-sultones, 23 527 P-tocopherol, 25 793 P-tocotrienol, 25 793 P-vinylacrylic acid, physical properties, 5 33t... 

With the advent of modern techniques, instrumentation and automation in isolation and structural characterization, numerous antidiabetic compounds have been isolated, purified and identified from different natural sources, especially medicinal plants. This part summarizes promising natural chemical entities with diverse structures reported for their therapeutic activities against diabetes. These compounds are broadly categorized into alkaloids, terpenoids, flavonoids, and phenolics, including compounds from other groups. 

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