Naturally occurring dimeric triterpenoids: Occurrence, chemistry and bioactivities

Chemical Constituents from Uapaca guineensis (Phyllanthaceae), and the Computational Validation of Their Antileishmanial and Anti-inflammatory Potencies

“…During the chemical investigations of the root bark of Uapaca guineensis, nine compounds have been isolated and characterized as lupeol (1), betulin (2), betulinic acid (3), β-amyryl acetate (4), physcion (5), quercetin (6), rutin (7), β-sitosterol (8), and β-sitosterol-3-O-β-D-glucopyranoside (9), respectively. Although all the compounds are reported for the first time from the species U. guineensis, the lupane-type triterpenoids 1-3 have been obtained from U. paludosa, while compounds 4 and 9 have been reported from U. togoensis, and some structurally close flavonoids to 6 and 7 have been obtained from U. heudelotti.…”

“…Although in vitro and in vivo studies are important to support the in silico results, the current results are important in supporting the use of the plant in traditional medicine for the treatment of skin diseases, leishmaniasis, and inflammatory diseases as well as giving further insights into the development of new potent drugs. spectrum of β-sitosterol (8). Figure 20S: 1 H NMR spectrum of daucosterol (9) in CD3OD + CDCl3.…”

Biogenetic and biomimetic synthesis of natural bisditerpenoids: hypothesis and practices

“…24 The example labdane dimers, ent-13 0nor-13 0 -oxomethylisoozate dimer (9) and ent-methylisoozate dimer (10), were isolated from the stem bark of Xylopia aromatica. 25 Cunlanceloic acids B-D (11)(12)(13) are asymmetric labdane DA adducts isolated from the cones of Cunninghamia lanceolata. 26…”

“…9,10 Among the many types of natural oligomers, oligomeric terpenoids are famous for their structural complexity and diversity; accordingly, studies have reported the discovery of oligomeric terpenoids, such as dimers, trimers, and tetramers of sesquiterpenes. 4 So far, for higher terpenoids, only dimeric diterpenoids and triterpenoids have been discovered, 2,11 partly because of the challenges of isolation and identication posed by the greater structural complexity. Unsurprisingly, bisditerpenoids and bistriterpenoids have been shown to have signicant and diverse biological activities, such as the bisditerpenoid eupractenoid A, which has an inhibitory effect on a-glucosidase, and the bistripenoid krishnadimer A, which has cytotoxic effects in tumor cells.…”

Chemistry and pharmacological aspects of Aridanin, a lead compound from <i>Tetrapleura tetraptera</i> (Fabaceae)

“…It is well known that medicinal plants are largely used around the world in healthcare system as alternative treatments for several diseases due to their important chemical constituents that constitute an important reservoir of potential leads in the new drug development (Happi et al, 2021;Happi, Nangmo, et al, 2022;Happi, Ntabo, et al, 2022). Our recent report on naturally occuring dimeric triterpenoids outlined that triterpenoids are one of the most distributed class of compounds throughout natural sources (plants, animals, microorganisms) with more than 20,000 known structures sorted to more than 100 different scaffolds (Happi, Ntabo, et al, 2022). Triterpenoids are formed from cyclization of squalene via the intermediate 2,3-oxidosqualene produced in a reaction catalysed by squalene epoxidase.…”