Triterpenes from Protium Hebetatum Resin

Abstract

Three olean (β-amyrenone, β-amyrin and maniladiol), three ursane (α-amyrinone, α-amyrin and breine) and four tirucallane (3-oxotirucalla-8,24-dien-21-óic acid, 3α-hydroxytirucalla-8,24-dien-21-oic acid, 3α-acetoxytirucalla-8,24-dien-21-oic acid and 3α-hydroxytirucalla-7,24-dien-21-oic acid) triterpenes were isolated from the oleoresin of Protium hebetatum Daly. The structures were established mainly by 13 C, 1D and 2D NMR spectroscopic analysis. The isolation of 3α-hydroxytirucalla-8,24dien-21-oic acid permitted correction of the chemical shift assignments of some of its carbon atoms.

Chemical Composition of South American Burseraceae Non‐volatile Oleoresins and Preliminary Solubility Assessment of their Commercial Blend

“… References: (a) Mathe et al , ; (b) Budziekiewicz et al , 1963; (c) Stacey et al , ; (d) Papageorgiou et al , ; (e) Assimopoulou and Papageorgiou, ; (f) Tessier et al , ; (g) Sawadogo et al , 1985; (h) Usubillaga et al , ; (i) Marques, ; (j) Marques et al , ; (k) Van der Doelen et al , ; (l) Dietemann et al , ; (m) Colombini et al , ; (n) Djerassi et al , ; (o) Ogunkoya, 1985; (p) Dietemann et al , .…”

“…Isolation of minor and less frequent compounds of the lupane, taraxane, friedelane and hopane has been reported (Susunaga et al, 2001, Usubillaga et al, 2004. Tetracyclic triterpenes have also been isolated and characterised from oleoresins of Protium and Trattinnickia species (Maia et al, 2000;Lima et al, 2004;Usubillaga et al, 2004;Marques et al, 2010).…”

Antimicrobial, Cytotoxic, and α-Glucosidase Inhibitory Activities of Ethanol Extract and Chemical Constituents Isolated from Homotrigona apicalis Propolis—In Vitro and Molecular Docking Studies

“…From a propolis sample collected in Binh Dinh province, a total of nine constituents were isolated (Figure 1), including four sesquiterpenes: spathulenol (1), 1αH,5βH-aromandendrane-4β,10α-diol (2), 1β,6α-dihydroxy-4(15)-eudesmene (3), and 1βH,5βH-aromandendrane-4α,10β-diol (4); three triterpenes: acetyl oleanolic acid (5), 3α-hydroxytirucalla-8,24-dien-21-oic acid (6), and ursolic acid (7); and two xanthones: cochinchinone A (8) and α-mangostin (9). The chemical structures of the isolated compounds were elucidated by NMR and by the comparison of the data (SI) with those in the literature [5,[30][31][32][33][34][35][36][37][38]. Xanthones 8 and 9 were previously isolated from Lisotrigona spp.…”

Volatile Constituents of Two Species of Protium from the Atlantic Rainforest in the State of Pernambuco, Brazil

“…However, Protium species are also found in fragments of the Atlantic rainforest in northeastern Brazil and are locally known as "almeçaga" or "breu branco". These species produce triterpenenes, essential oils and oil resin [2,3], which are responsible for the prominence of Burseraceae species in ethnobotany and their use in folk medicine for the treatment of wounds and ulcers. Pharmacological studies, carried out to determine the antimicrobial, antioxidant and antinociceptive [4,5] properties of oil resin of various Protium species, demonstrated the potential of these oils as antiinflammatory, antinociceptive and gastro-protective agents [6].…”