CATALPOL AND METHYLCATALPOL: NATURALLY OCCURRING GLYCOSIDES IN PLANTAGO AND BUDDLEIA SPECIES

Arbuscular mycorrhizal fungal species suppress inducible plant responses and alter defensive strategies following herbivory

“…Only one of these three species, S. calospora, has been reported to associate with Plantago lanceolata in its European native range (Oehl et al 2003). P. lanceolata contains carbonbased secondary compounds, iridoid glycosides (Bobbitt and Segebarth 1969;Duff et al 1965), primarily aucubin and catalpol (Bowers and Stamp 1992), compounds shown to be toxic or deterrent to generalist, but not specialist, herbivores (Bowers 1991 and references therein), that are sequestered by Junonia coenia larvae (Bowers and Collinge 1992;Bowers and Puttick 1986) as defenses against enemies. Aucubin and catalpol vary in their degree of toxicity and cost of production.…”

“…Plants associated with Glomus white increased overall proportions of catalpol and reduced overall proportions of aucubin (Fig. 1b), a shift likely due to both the movement of compounds to damaged tissues and the conversion of aucubin into catalpol (Duff et al 1965). Increasing the proportion of catalpol, but not the total concentration of iridoid glycosides, may be a strategy employable only by plants with greater resources (Bennett and Bever 2007).…”

Studies in iridoid chemistry and spruce budworm (Choristoneurafumiferana) antifeedants

“…It is present to the extent of -1% of fresh plant weight in Aucuba japonica (8,9) and can be extracted and purified in large quantities (9).' In fact, aucubin has been used as starting material for the synthesis of optically active prostaglandinoids (9, 10).…”

Studies on Monoterpene Glucosides and Related Natural Products. XV. Confirmation of the Absolute Configuration of Catalpol

“…Recently, Yosioka and his co-workers isolated a new glucoside, picroside I, from the rhizomes and roots of Picrorhiza kurooa ROYLE, and concluded that it was 6'-O-trans-cinnamoylcatalpol (5). Then they noticed that the basis of the assignment of the configuration at C-6 in compound (3) by Bobbitt, et at.…”

“…fractions No. [2][3][4][5][6][7][8][9] was rechromatographed on silica gel (5g) with CH2Cl2 as eluent and 5ml fractions were collected.…”