Ipomoea tricolor tricolorins

Two trisaccharide macrolactones have been characterized from the aerial parts of Ipomoea tricolor Cav. (syn. Ipomoea violacea L.) (heavenly blue), namely, tricolorins... 

Pereda-Miranda R, Mata R, Anaya AL, Wickramaratne DBM, Pezzuto JM, Kinghom AD (1993) Tricolorin A, Major Phytogrowth Inhibitor from Ipomoea tricolor. J Nat Prod 56 571... 

Bah M, Pereda-Miranda R (1996) Detailed FAB-Mass Spectrometry and High Resolution NMR Investigations of Tricolorins A-E, Individual Oligosaccharides from the Resins of Ipomoea tricolor (Convolvulaceae). Tetrahedron 52 13063... 

Ohno, T., Doolan, K., Zibilske, L.M., Liebman, M., Gallandt, E., Berube, C. Phytotoxic effects of red clover amended soils on wild mustard seedling growth. Agricult Ecosyst Environm 2000 78 187-192. Pereda-Miranda, R., R. Mata, A.L. Anaya, J.M. Pezzuto, D.B.M. Wickramaratne, A.D. Kinghorn. Tricolorin A, major phytogrowth-inhibitor from Ipomoea tricolor. J Natural Products 1993 56 571-582. 

Tricolorin A (46) and G (47) are prototype members of this class of amphiphilic glycoconjugates (24). They constitute the allelochemical principles of Ipomoea tricolor Cav., a plant used in traditional agriculture in Mexico as a cover crop to protect sugar cane against invasive weeds. Their molecular mechanism of action likely involves the inhibition of the FT-ATPase of the plasma membrane, an enzyme that plays a crucial role in plant cell physiology. Moreover, 46 acts as a natural uncoupler of photophosphorylation in spinach chloroplasts. This compound also displays general cytotoxicity against several... 

Epimer Tricolorin E C50H86O21 1023.217 Constit. of Ipomoea tricolor. 

Deacyl, 4 -0-(3-hydroxy-2-methylbu-tanqyl)(2R,3R-) Tricolorin C C50H86O22 1039.216 Constit. of Ipomoea tricolor. 

Fig. 8.3 Resin glycosides from the whole plant of Ipomoea tricolor and the leaves of I. squamosa, two neotropical vines The structures of tricolorin C and of ipomoeassin E differ remarkably with regard to (i) the hydroxy fatty acid moieties, (ii) the position of their linkage to the oligosaccharide components, (iii) the number and - in part - the types of monosaccharides involved, and (iv) the other acyl residues. Tricolorin H represents a heterodimer of two trisaccharides, tricoloric acid C (highlighted in grey) and an acylated (mba) derivative of the monomeric macrolactone tricolorin G (right), linked to each other by esterification of the jalapinolic add moiety of tricoloric acid C at position C-3" (glu) of the macrolactone part...

Moderate in vitro activities against Mycobacterium tuberculosis (MIC 16-32 tg/ ml) were also documented in a study with tricolorins A-E providing the rationale for the traditional use of Ipomoea tricolor in the treatment of tuberculosis (Rivero-Cruz et al. 2005). 

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