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.

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Available from: Gérald Culioli, Sep 02, 2014
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    • "enhancing, antibacterial, antifungal, antiviral, antiseptic wound healing, anti-inflammatory, and anti-cancer properties (Crow, 2006). It has a long history of use and is considered as one of the oldest fragrant and medicinal resins known throughout the world (Culioli et al., 2003). Frankincense (Boswellia sacra) trees are found in Oman, Somalia, Ethiopia, Yemen, the Southern Arabian Peninsula, and India (Hamm et al., 2005; Crow, 2006; Marshall, 2003; Baser et al., 2003). "
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    ABSTRACT: Frankincense considered as holy plant in Oman and its resin commonly used for fragrance purposes. In addition, frankincense resin has many ailments curing history and it is observed by local people. Essential oil extracted from frankincense resin either by hydro-distillation (HD) or microwave assisted hydro-distillation (MHD) method has numerous biological activities such as antimicrobial, antioxidant, anti-cancer, anti-analgesic etc. Gas chromatography coupled with mass spectrometry (GC-MS) chemical profiling of this essential oil revealed that the major component is α-pinene and it is associated with other triterpenes. HD and MHD widely used to extract the essential oil from frankincense but it requires sophisticated set up to achieve efficient extraction. It is well known that soxhlet extraction procedure is very common to obtain high yield of phytochemicals from the plant or microbial sources and it is very simple, feasible and efficient extraction method. In this study for the first time we define the soxhlet extraction based protocol to extract heavy triterpenes from frankincense and we tested them for antimicrobial activity against different pathogens (E.coli, klebsiella, staphylococcus and bacillus). In addition chemical profiling of heavy oil done by GC-MS. Heavy oil extracted from frankincense exhibited considerable antimicrobial activity against the organism tested. Our data revealed that α-pinene is major content of this heavy oil about 61.5% followed by α-amyrin (20.6%), β-amyrin (8.1%), β-phellandrene (1.47%) and camphene (1.04%). Adapting simple and efficient extraction method is always warranted to obtain high yield of phytochemicals. To the best of our knowledge this is the first report on heavy oil extraction from Oman’s frankincense by soxhlet extraction method.
    Full-text · Article · May 2015
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    • "This is probably due to the analgesic effects of frankincense [2] [3] . In Oman, B. sacra gum extracts are utilized traditionally in various folk medicines for strengthening the teeth and gum, for stimulating the digestion process, to combat halitosis and in many more health problems, including inflammatory disorders and cancer [4] [5] . In Dhofar (Southern Oman), the frankincense resin is soaked in water overnight and taken A R T I C L E I N F O A B S T R A C T Objective: To investigate the analgesic effect of Boswellia sacra (B. "
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    ABSTRACT: Objective: To investigate the analgesic effect of Boswellia sacra (B. sacra), which could support the Omani traditional uses of frankincense for muscle, stomach, and arthritis pain. Methods: The crude extract, the essential oils and various sub-fractions of the crude methanol extract (each 300 mg/kg of the body weight of the animal) obtained from the resin of B. sacra were administered orally, and were evaluated for their analgesic activities by using two well known models of pain in mice, viz. acetic acid induced writhing test and formalin induced pain test in mice. Results: Of 13 samples, almost all of them were effective at an orally administered dose of 300 mg/kg of the body weight. The acetic acid induced writhes were inhibited in all the three phases with comparable values to the standard drug aspirin (300 mg/kg of body weight) with inhibition of 67.6% in phase I, 66.8% in phase II, and 37.9% in phase III. At the same time, all the tested samples were found effective in both the early and the late phases of formalin test. In formalin test, most of the tested samples showed more inhibitory effects as compared to the standard drug aspirin (300 mg/kg of body weight), which showed 36.2% and 29.6% inhibition in early and late phases respectively. Among the tested samples, the most significant inhibition was produced by Shabi frankincense oil (57.5% in early phase, and 55.6% in late phase). Interestingly, the extracts showed comparable percentage of inhibition to the oil and found in the following order: 60% chloroform/n-hexane sub-fraction (55.3% in early phase, and 66.7% in late phase), and 70% chloroform/n-hexane sub-fraction (59.6% in early phase, and 63.0% in late phase). Conclusions: The present study provided the scientific justification about the analgesic properties of the essential oils, extract, and various sub-fractions obtained from the resin of B. sacra, thus validating its use in traditional folk medicines and other products; and hence supporting the development in the analgesic properties of bioactive natural substances.
    Full-text · Article · Sep 2014 · Asian Pacific Journal of Tropical Biomedicine
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    • "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). "
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    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.
    Full-text · Article · Jan 2014 · ArchéoSciences / Journal of Archaeometry
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