A lupane triterpene from frankincense (Boswellia sp., Burseraceae)

Université d´Avignon et des Pays du Vaucluse, Avinyó, Provence-Alpes-Côte d'Azur, France
Phytochemistry (Impact Factor: 2.55). 03/2003; 62(4):537-41. DOI: 10.1016/S0031-9422(02)00538-1
Source: PubMed


A new lupane-type triterpene, 3alpha-hydroxy-lup-20(29)-en-24-oic acid, was isolated from the methanolic extract of "Erytrean-type" resin of commercial frankincense together with the known 3alpha-hydroxy-olean-12-en-24-oic acid (alpha-boswellic acid) and 3alpha-hydroxy-urs-12-en-24-oic acid (beta-boswellic acid). Their structures were characterized on the basis of chemical and spectral evidence including two dimensional NMR experiments and mass spectrometric techniques.

Download full-text


Available from: Gérald Culioli, Sep 02, 2014
78 Reads
  • Source
    • "Standard molecules were used for their identifi cation in molecular composition of archaeological resins: α-amyrin, β-amyrin, lupeol, and lupenone were purchased from Extrasynthèse (Genay, France), while α-amyrone and β-amyrone were purchased from BCP instruments (Irigny, France), 3-epi -lupeol, 3-epi -α-amyrin, 3-epi -β-amyrin were isolated by our team from commercial resin samples (Culioli et al , 2003). "
    [Show abstract] [Hide abstract]
    ABSTRACT: During archaeological excavations at "Templo Mayon" site, between 2006 and 2008 in Mexico City, thirteen Aztec offerings were found. Among the materials of these offerings the most abundant was a resinous substance used as adhesive, molding material for figures or as a spiritual offering. Two archaeological samples from two Aztec artifacts were analyzed by HPLC. Their global molecular profile was compared to that of fresh botanically certified copal resins from six species of Mexican Bursera (Burseraceae family). This study aims to complete a previous research based on GC-MS results that focused only on triterpenic molecular resin composition. The molecular profile of archaeological samples suggests a botanical copal origin related to B. bipinnata or maybe B. stenophylla species which triterpenic profile composition is identical to.
    ArchéoSciences / Journal of Archaeometry 01/2014;
  • Source
    • "In addition an interesting anti-inflammatory activity of this plant has been recently reported (Carretero et al., 2008; Noguera et al., 2004; Abad et al., 1996; Sosa et al., 2002). Many species belonging to the genus Bursera have been reported to contain essential oils, triterpenes, steroids, bilignans, podophyllotoxin-like lignans and flavonoids found in particular in their resins (Culioli et al., 2003; Syamasundar and Mallavarapu, 1995), being the genus Bursera characterized by the presence of resins. Also for B. simaruba studies on the chemical composition of the resin extract are present in literature (Peraza-Sànchez and Peň a-Rodrìguez, 1992; Peraza-Sànchez et al., 1995; Borges-Argaez et al., 2000). "
    [Show abstract] [Hide abstract]
    ABSTRACT: Phytochemical investigation of the methanolic extract of Bursera simaruba bark led to the isolation of 11 compounds, including lignans yatein, beta-peltatin-O-beta-D-glucopyranoside, hinokinin and bursehernin, and three natural compounds namely 3,4-dimetoxyphenyl-1-O-beta-D-(6-sulpho)-glucopyranoside, 3,4,5-trimetoxyphenyl 1-O-beta-D-(6-sulpho)-glucopyranoside and 3,4-diidroxyphenylethanol-1-O-beta-D-(6-sulpho)-glucopyranoside. Their structures were established by NMR and ESI/MS experiments. Additionally, an LC-ESI/MS qualitative study on the phenolic compounds and an LC-ESI/MS/MS quantitative study on the lignans found in the methanolic extract of B. simaruba bark were performed to give value to the plant as source of these biological active compounds. Quantitative analyses results confirmed that compounds yatein, beta-peltatin-O-beta-D-glucopyranoside, hinokinin and bursehernin are major compounds in the bark and, in particular, beta-peltatin-O-beta-D-glucopyranoside appears to be the most abundant.
    Phytochemistry 04/2009; 70(5):641-9. DOI:10.1016/j.phytochem.2009.02.009 · 2.55 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: This review covers the isolation and structure determination of triterpenoids including squalene derivatives, protostanes, lanostanes, holostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, lupanes, oleananes, friedelanes, ursanes, hopanes, isomalabaricanes and saponins; 574 references are cited.
    Natural Product Reports 02/1994; 11(1):91-117. DOI:10.1039/b808530g · 10.11 Impact Factor
Show more