Triterpenoids: calendula

Among five triterpenoids isolated from Calendula officinalis flowers, P-amyrin (119), faradiol (232), i /-taraxasterol (238), taraxasterol (239), and lupeol (238), the diol 232 was the most active. It showed a dose-dependent effect with a potency that equals that of indomethacin (5) in the topical anti-inflammatory assay with croton oil [33]. Esterification at C-3 of 232 with a fatty acid reduced the activity by more than 50% [33] consistent with our observation in the TPA-induced assay described above. The anti-inflammatory properties, as determined by croton oil-induced edema of mouse ear, of faradiol-3-O-myristate (233) and its 3-O-palmitate (234), the main components of lipophilic extracts of C. officinalis flowers, were shown to be contribute significantly to the pronounced antiphlogistic activity of the lipophilic extracts of C. officinalis flowers [34]. 

Further work on the free and ester-bound triterpenoid alcohols in cellular subtractions of Calendula officinalis flowers has appeared. An investigation of the mass spectral fragmentation of pentacyclic hydrocarbons in petroleum has been published. ... 

As expected, lanosterol (70) but not cycloartenol (72) was converted in rats into cholesterol on the other hand both triterpenoids are utilized by Zea mays in the formation of C-24-alkylated sterols. Sterol formation has been demonstrated in the fern Polypodium vulgare, tobacco, and Calendula... 

Calendula officinalis (marigold) contains a variety of carotenoids, saponins, steroids, sesquiterpenoids, and triterpenoids. 

The hydroxylation of triterpenols to the corresponding diols in the flowers of Calendula officinalis apparently occurs exclusively in the chromoplasts, " and the triterpenol ester is substrate. The formation of triterpenoid analogues of carotenoids... 

New lupanes include heliantriol B2 (93) from the flowers of Helianthus annuus and also Calendula officinalis (Compositae) and the triol (94) from the bark of an unidentified Glochidion species (Euphorbiaceae). The (known) triterpenoids from several other species from Euphorbiaceae have been identified. ... 

Della Loggia, R., Tubaro, A., Sosa, S., Becker, H., Saar, St. and Isaac, O. 1994, The role of triterpenoids in the topical antiinflammatory activity of Calendula officinalis flowers , Planta Medica 60 516-520. 

Neukirch H, D Ambrosio M, Dalla Via J, Guerriero A (2004) Simultaneous quantitative determination of eight triterpenoid monoesters from Howcts of 10 varieties of Calendula officinalis L. and charactmsation of a new triterpenoid monoester. Phytochem Anal 15 30-35... 

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