Iridoid glucosides derivatives

Mouries C, Rakotondramasy VC, Libot F, Kock M, Tillequin F, Deguin B (2005) Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin. Chem Biodivers 2 695-703... 

Contin, A. et al.. The iridoid glucoside secologanin is derived from the novel triose phosphate/pyruvate pathway in a Catharantus roseus cell culture, FEES Lett., 434, 413, 1998. 

Contin A, Van der Heijden R, Lefeber AWM, Verpoorte R. The Iridoid Glucoside Se-cologanin is Derived from the Novel Triose Phosphate/Pymvate Pathway in a Ca-tharmthus roseus Cell Culture. FEBS Letters 1998 434 413-416. 

Strictosidine synthetase catalyzes the stereospecific condensation of trypt-amine and the iridoid glucoside secologanin to form strictosidine. The product is the precursor of the monoterpenoid-derived indole and quinoline alkaloids. 

Tissue Cultures, Microbial Transformations.—Little success has rewarded the search for cell cultures that effectively biosynthesize monoterpenes de novo. The most impressive studies utilize cultures from a variety of Mentha spp. yields of oil were some 60 % (w/v) of those in the parent plants, but the monoterpene products were generally more oxidized (i.e. ketones extra C=C bonds predominated). In vitro, oxidation at C-3 of the menthane skeleton was also restricted, apparently owing to an inhibition of the enzymic reduction of the 4(8) double bond in the intermediates formed.925 926 Colchicine stimulated synthesis of essential oil by Mentha cultures.927 Iridoid glucosides have been produced by cultured cells of Gardenia spp.673 Menthone was biotransformed to neomenthol by Mentha suspension cultures,928 and Nicotiana lines oxidized linalool and its derivatives at C-10 to aldehydes and alcohols,929 and also foreign substrates such as a-terpineol (at C-6 and C-7) and /raw.s-/ -menthan-9-en-l-ol (at C-4 and C-10).930... 

H. Unnatural Alkaloid Derivatives from Iridoid Glucosides. 341... 

The basic structure of TIAs includes an indole nucleus derived from tryptamine, the decarboxylation product of the aminoacid tryptophan, and a versatile C9 or CIO terpenoid unit arising from the iridoid glucoside secologanin, Fig. (4). 

M. and its derivatives occur in all Ericaceae where the bitter taste of the iridoid glucoside protects the plants from predators. M. was flrst isolated from genuine pinesap (Monotropa hypopitys, Monotropaceae). M. 

Chaudhury, R. K., F. U. Afifi-Yazar, and O. Sticher, C NMR spectroscopy of naturally occurring iridoid glucosides and their acylated derivatives. Tetrahedron, 36, 2317-2326 (1980). 

Recent researches led to isolation and characterization of two new iridoid glucosides loganin derivatives logmalieids A and B as well as to the first report of loganic acid and secoxyloganin in Cornus officinalis fruits [Ma et al., 2014],... 

Loganin is an iridoid glucoside which occupies a central position in the biosynthesis of Corynanthe, Aspidosperma, Iboga, Ipecacuanha, Cinchona, and structurally simpler monoterpene alkaloids. For a review of the extensive researches that led to confirmation of the key role of loganin in alkaloid biosynthesis, see A. R. Battersby, Biochem. Soc. Symp., 29, 157 (1970) A. R. Battersby, Chem. Soc. Spec. Period. Rep., 1, 31 (1971) A. I. Scott, Accts. Chem. Res., 3, 151 (1970). For a useful account of the chemistry of iridoid glucosides see, J. M. Bobbitt and K. -P. Segebarth in Cyclopentanoid terpene Derivatives, Eds., W. I. Taylor and A. R. Battersby, Marcel Dekker, New York, 1969, p 1. 

Thirty-three known iridoid and secoiridoid glucosides have been analysed by gas chromatography of their trimethylsilyl derivatives. G.c.-m.s. analysis of several representative compounds e.g. 4-CO2H, 4-C02Me, 4-unsubstituted) demonstrated the feasibility of iridoid-containing plant extract analysis and resulted in the identification of secologanoside 11-methyl ester (99 R = H, X = CH2) from Lonicera morrowii the sixth paper in a series of chemotaxonomic studies on iridoids illustrates the need for accurate analysis of minor components. ... 

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