Incensole

The resin of Boswellia carterii Birdw.

Distribution of the anti-inflammatory and anti-depressant compounds: Incensole and incensole acetate in genus Boswellia.[Pubmed:30802641]

Phytochemistry. 2019 May;161:28-40.

Incensole and its acetate have shown anti-inflammatory and anti-depression activities due to their ability to activate ion channels in the brain to alleviate anxiety or depression. The natural occurrence of these two structurally and medicinally fascinating 14-membered diterpenoids was reported mainly from the genus Boswellia. Incensole and Incensole acetate were detected in and isolated from both essential oils and resins of frankincense. One total synthesis was reported for Incensole. Both Incensole and its acetate served as precursors for several synthetic transformations. Given the fact that no specific enzymes were isolated from Boswellia trees, the major sources for Incensole and Incensole acetate, the biosynthetic pathway of these two compounds was only speculated. Recent studies on Incensole and Incensole acetate including ours have revealed another secret of the ancient drug. Understanding their mode of action will open a door in modern neurobiology and provides new insights on the mysterious diseases of the nervous system. This review interpretatively discusses the natural existence of Incensole and Incensole acetate, the variation of their percentages in different Boswellia species and other sources, their synthetic modifications, their biosynthesis and their therapeutic potential.

Incensole acetate prevents beta-amyloid-induced neurotoxicity in human olfactory bulb neural stem cells.[Pubmed:29913410]

Biomed Pharmacother. 2018 Sep;105:813-823.

beta-Amyloid peptide (Abeta) is a potent neurotoxic protein associated with Alzheimer's disease (AD) which causes oxidative damage to neurons. Incensole acetate (IA) is a major constituent of Boswellia carterii resin, which has anti-inflammatory and protective properties against damage of a large verity of neural subtypes. However, this neuroprotective effect was not studied on human olfactory bulb neural stem cells (hOBNSCs). Herein, we evaluated this effect and studied the underlying mechanisms. Exposure to Abeta25-35 (5 and 10muM for 24h) inhibited proliferation (revealed by downregulation of Nestin and Sox2 gene expression), and induced differentiation (marked by increased expression of the immature neuronal marker Map2 and the astrocyte marker Gfap) of hOBNSCs. However, pre-treatment with IA (100muM for 4h) stimulated proliferation and differentiation of neuronal, rather than astrocyte, markers. Moreover, IA pretreatment significantly decreased the Abeta25-35-induced viability loss, apoptotic rate (revealed by decreased caspase 3 activity and protein expression, downregulated expression of Bax, caspase 8, cyto c, caspase3, and upregulated expression of Bcl2 mRNAs and proteins, in addition to elevated mitochondrial membrane potential and lowered intracellular Ca(+2)). IA reduced Abeta-mediated ROS production (revealed by decreased intracellular ROS and MDA level, and increased SOD, CAT, and GPX contents), and inhibited Abeta-induced inflammation (marked by down-regulated expression of IL1b, TNFa, NfKb, and Cox2 genes). IA also significantly upregulated mRNA and protein expression of Erk1/2 and Nrf2. Notably, IA increased the antioxidant enzyme heme oxygenase-1 (HO-1) expression and this effect was reversed by HO-1 inhibitor zinc protoporphyrin (ZnPP) leading to reduction of the neuroprotective effect of IA against Abeta-induced neurotoxicity. These findings clearly show the ability of IA to initiate proliferation and differentiation of neuronal progenitors in hOBNSCs and induce HO-1 expression, thereby protecting the hOBNSCs cells from Abeta25-35-induced oxidative cell death. Thus, IA may be applicable as a potential preventive agent for AD by its effect on hOBNSCs and could also be used as an adjuvant to hOBNSCs in cellular therapy of neurodegenerative diseases.

Frankincense and myrrh essential oils and burn incense fume against micro-inhabitants of sacral ambients. Wisdom of the ancients?[Pubmed:29530608]

J Ethnopharmacol. 2018 Jun 12;219:1-14.

ETHNOPHARMACOLOGICAL RELEVANCE: Essential oils obtained from resins of Boswellia carteri Birdw. and Commiphora myrrha (Nees) Engl., commonly known as frankincense and true myrrh respectively, have been used extensively since 2800 BCE for the treatment of skin sores, wounds, teeth, inflammation, and urinary tract diseases in traditional medicine; for preparation of mummification balms and unguents; and also as incense and perfumes. Since ancient times, burning of frankincense and myrrh in places of worship for spiritual purposes and contemplation (a ubiquitous practice across various religions) had hygienic functions, to refine the smell and reduce contagion by purifying the indoor air. AIM OF THE STUDY: The general purpose of the study was to assess the in vitro antimicrobial potential of the liquid and vapour phases of B. carteri and C. myrrha essential oils and burn incense, as well as to test the effectiveness of their in situ application to cleanse microbially-contaminated air within the ambient of an investigated 17th-century church. MATERIALS AND METHODS: The chemical composition of B. carteri and C. myrrha essential oils, obtained by hydrodistillation of frankincense and true myrrh oleo gum resins was determined using GC/MS, and antimicrobial properties of their liquid and vapour phases were assessed by the broth microdilution and microatmosphere diffusion methods. Chemical analysis of burn incense fume obtained using bottle gas washing with dichloromethane as a solvent was performed by GC/MS, while its antimicrobial activity was evaluated using a modified microatmosphere diffusion method to evaluate germination inhibition for fungi and CFU count reduction for bacteria. The in situ antimicrobial activity of B. carteri burn incense and essential oil vapour phase was assessed in the sealed nave and diaconicon of the church, respectively. RESULTS: The dominant compounds of B. carteri EO were alpha-pinene (38.41%) and myrcene (15.21%), while C. myrrha EO was characterized by high content of furanoeudesma-1,3-diene (17.65%), followed by curzerene (12.97%), beta-elemene (12.70%), and germacrene B (12.15%). Burn incense fume and soot had alpha-pinene (68.6%) and Incensole (28.6%) as the most dominant compounds, respectively. In vitro antimicrobial assays demonstrated high bacterial and fungal sensitivity to the liquid and vapour phases of EOs, and burn incense fume. In situ application of B. carteri EO vapour and incense fume resulted in reduction of air-borne viable microbial counts by up to 45.39+/-2.83% for fungi and 67.56+/-3.12% for bacteria (EO); and by up to 80.43+/-2.07% for fungi and 91.43+/-1.26% for bacteria (incense fume). CONCLUSIONS: The antimicrobial properties of essential oil derived from frankincense, a compound with well-known traditional use, showed that it possesses a clear potential as a natural antimicrobial agent. Moreover, the results suggest possible application of B. carteri EO vapour and incense fume as occasional air purifiers in sacral ambients, apart from daily church rituals.

Conformational analysis of macrocyclic frankincense (Boswellia) diterpenoids.[Pubmed:29492734]

J Mol Model. 2018 Mar 1;24(3):74.

Frankincense oleoresin has been used in traditional medicine for more than 5000 years. The phytochemistry of frankincense (Boswellia spp.) resins includes triterpenoids (including boswellic acids and their derivatives), diterpenoids (cembrenoids and cneorubenoids), and essential oils. The macrocyclic cembrene diterpenoids may play a part in the biological activities of frankincense resin, but neither the biological targets nor the modes of interaction with the targets are currently known. How these macrocycles interact with biological macromolecules likely depends on what conformation(s) are energetically available to them. In this work, a conformational analysis of 15 Boswellia cembrene diterpenoids and 1 verticillane diterpenoid was carried out at the B3LYP/6-31G* and M06-2X/6-31G* levels of theory, including the SM8 aqueous solvation model. The lowest-energy conformations of boscartin B and Incensole oxide were the same as the previously reported X-ray crystal structures, while the lowest-energy conformations of boscartins A and C were very similar to the crystal structures. Boscartins D-H and isoIncensole oxide showed only one low-energy conformation for each compound and are predicted to be conformationally locked. Incensole, isoincensolol, and serratol are predicted to be conformationally mobile with several low-energy forms. The conformational mobility of Boswellia cembrenoid diterpenoids depends largely on the degree of epoxidation, either oxirane or tetrahydrofuran rings.

Quantification of Incensole in Three Boswellia Species by NIR Spectroscopy Coupled with PLSR and Cross-Validation by HPLC.[Pubmed:29314317]

Phytochem Anal. 2018 May;29(3):300-307.

INTRODUCTION: Incensole can be considered as a biomarker for Boswellia species which is a diterpene that has received remarkable pharmacological interest recently due to its potent anti-inflammatory and anti-depressant activity. OBJECTIVE: Near-infrared (NIR) spectroscopy coupled with PLSR (partial least squares regression) as a robust, rapid and alternative method was used to quantify the content of Incensole in three species namely B. papyrifera, B. sacra and B. serrata and cross-validated by high-performance liquid chromatography (HPLC). MATERIALS AND METHODS: NIR spectrophotometer was used for the quantification of Incensole standards and Boswellia species in absorption mode in the wavelength range between 700 and 2500 nm. A PLSR model was built from the obtained spectral data using 70% of the Incensole working standard solutions (training set), ranging from 0.5 to 100 ppm. The PLSR model obtained has a R(2) value of 98% with a correlationship of 0.99 and a good prediction with root mean square error for prediction (RMSEP) value of 3.2%. RESULTS: The results indicated that the methanol (MeOH) extract of B. papyrifera resin has the highest concentration of Incensole (18.4%) followed by n-hexane (13.5%) and ethyl acetate (3.6%) while trace amounts was detected in the fractions of B. sacra and no Incensole was detected in the fractions of B. serrata. CONCLUSION: The findings are in total agreement with the HPLC analysis suggesting that NIR spectroscopy coupled with PLSR is a robust, rapid and non-destructive alternate method for the quantification of Incensole in B. papyrifera. Copyright (c) 2018 John Wiley & Sons, Ltd.

Terpenoids from the Oleo-Gum-Resin of Boswellia serrata and Their Antiplasmodial Effects In Vitro.[Pubmed:28738439]

Planta Med. 2017 Oct;83(14-15):1214-1226.

In the course of our ongoing search for new natural products as leads against protozoal diseases, the dichloromethane extract of Indian frankincense, the oleo-gum-resin obtained from Boswellia serrata, showed in vitro activity against Plasmodium falciparum. Bioactivity-guided fractionation led to the isolation of eight diterpenes: (1S,3E,7E,11R)-verticilla-3,7,12(18)-triene (1), cembrene A (2), serratol (3), 1S,3E,7R,8R,11E-7,8-epoxy-cembra-3,11-dien-1-ol (4), Incensole oxide (5), rel (1S,3R,7E,11S,12R)-1,12-epoxy-4-methylenecembr-7-ene-3, 11-diol (6), isoIncensole oxide (7), and isodecaryiol (8). Furthermore, 10 triterpenes, namely, oleanolic acid (9), 11-keto-beta-boswellic acid (10), 3-epi-neoilexonol (11), uvaol (12), beta-boswellic aldehyde (13), 5alpha-tirucalla-8,24-dien-3alpha-ol (14), isoflindissone lactone (15), isoflindissol lactone (16), rel (8R,9S,20R)-tirucall-24-ene-3beta,20-diol (17), and rel (3alpha,8R, 9S,20R,24S)-20,24-epoxytirucalla-3,25-diol (18) as well as the sesquiterpene beta-bourbonene (19), the monoterpene carvacrol (20) and the phenyl propanoids methyleugenol (21), and p-methoxycinnamaldehyde (22) were isolated. All compounds were identified by mass spectrometry and nuclear magnetic resonance spectroscopic measurements. Compounds 6, 11, and 16-18 are described for the first time. Compounds 13 - 15 are isolated as natural products for the first time, compound 8 for the first time from a plant. Antiplasmodial IC50 values and cytotoxicity against L6 rat skeletal myoblasts were determined. Isoflindissone lactone (15) was the most active compound with an IC50 of 2.2 microM against P. falciparum and a selectivity index of 18.

Cembranoids from the Gum Resin of Boswellia carterii as Potential Antiulcerative Colitis Agents.[Pubmed:26457560]

J Nat Prod. 2015 Oct 23;78(10):2322-31.

Eight new cembranoids, boscartins A-H (1, 2, and 4-9), and the known Incensole oxide were isolated from the gum resin of Boswellia carterii. The absolute configurations of 1, 2, 4, and Incensole oxide were unequivocally resolved using single-crystal X-ray diffraction analysis with Cu Kalpha radiation, and the absolute configuration of 5 was resolved via electronic circular dichroism data. The antiulcerative colitis activities of the compounds were evaluated in an in vitro x-box-binding protein 1 (XBP 1) transcriptional activity assay using dual luciferase reporter detection. At 10 muM, compounds 1, 5, 6, and 7 significantly activated XBP 1 transcription with EC50 values of 0.34, 1.14, 0.88, and 0.42 muM, respectively, compared with the pGL3-basic vector control.

Identification of dehydroabietc acid from Boswellia thurifera resin as a positive GABAA receptor modulator.[Pubmed:25200370]

Fitoterapia. 2014 Dec;99:28-34.

In a two-microelectrode voltage clamp assay with Xenopus laevis oocytes, a petroleum ether extract (100 mug/mL) of the resin of Boswellia thurifera (Burseraceae) potentiated GABA-induced chloride currents (IGABA) through receptors of the subtype alpha(1)beta(2)gamma(2)s by 319.8% +/- 79.8%. With the aid of HPLC-based activity profiling, three known terpenoids, dehydroabietic acid (1), Incensole (2), and AKBA (3), were identified in the active fractions of the extract. Structure elucidation was achieved by means of HR-MS and microprobe 1D/2D NMR spectroscopy. Compound 1 induced significant receptor modulation in the oocyte assay, with a maximal potentiation of IGABA of 397.5% +/- 34.0%, and EC(5)(0) of 8.7 muM +/- 1.3 muM. This is the first report of dehydroabietic acid as a positive GABAA receptor modulator.

Major constituents of Boswellia carteri resin exhibit cyclooxygenase enzyme inhibition and antiproliferative activity.[Pubmed:24354175]

Nat Prod Commun. 2013 Oct;8(10):1365-6.

Aromatic gum from Boswellia carteri (olibanum oleogum) has long been used in Egyptian traditional medicine. Cyclooxygenase-1 (COX-1) enzyme inhibitory assay guided purification of the extracts of this resin resulted in five bioactive compounds, 3alpha-O-acetyl-8,24-dien-tirucallic acid (1), verticilla-4(20),7,11-triene (2), cembrene A (3), Incensole acetate (4), and Incensole (5). The pure isolates were investigated for their inhibitory effects on COX-1 and -2 enzymes and human tumor cell lines Hep-G2, MCF-7 and RAW 264.7. Compounds 1-5 inhibited COX-2 enzyme by 39.0, 32.7, 60.0, 46.3, and 49.8%, respectively. Furthermore, compound 2 showed an inhibitory concentration of 50% (IC50) at 9 microg/mL against Hep-G2 tumor cell line. This is the first report of COX-1 and -2 enzyme and tumor cell proliferation inhibitory effects of compounds 1 and 2.

Incensole acetate reduces depressive-like behavior and modulates hippocampal BDNF and CRF expression of submissive animals.[Pubmed:23015543]

J Psychopharmacol. 2012 Dec;26(12):1584-93.

Incensole acetate (IA), a constituent of Boswellia resin ('frankincense'), was previously demonstrated to exhibit an antidepressive-like effect in the Forced Swim Test (FST) in mice following single dose administration (50 mg/kg). Here, we show that acute administration of considerably lower dose (10 mg/kg) IA to selectively bred mice, showing prominent submissive behavior, exerted significant antidepressant-like effects in the FST. Furthermore, chronic administration of 1 or 5 mg/kg per day of IA for three consecutive weeks dose- and time-dependently reduced the submissiveness of the mice in the Dominant-Submissive Relationship test, developed to screen the chronic effect of antidepressants. This behavioral effect was concomitant to reduced serum corticosterone levels, dose-dependent down-regulation of corticotropin releasing factor and up-regulation of brain derived neurotrophic factor transcripts IV and VI expression in the hippocampus. These data suggest that IA modulates the hypothalamic-pituitary-adrenal (HPA) axis and influences hippocampal gene expression, leading to beneficial behavioral effects supporting its potential as a novel treatment of depressive-like disorders.

Efficient preparation of incensole and incensole acetate, and quantification of these bioactive diterpenes in Boswellia papyrifera by a RP-DAD-HPLC method.[Pubmed:22545396]

Nat Prod Commun. 2012 Mar;7(3):283-8.

Incensole and Incensole acetate, found in incense, are encouraging potent bioactive diterpenic cembrenoids, inhibiting Nuclear Factor-kappaB activation. Furthermore, Incensole acetate elicits psycho-activity in mice by activating the TRPV3 channels in the brain. Starting from crude extracts of the incense species Boswellia papyrifera Hochst., a convenient procedure for the efficient large-scale synthesis of Incensole and its acetate is presented. Additionally, a reversed-phase, diode-array-detection, high-performance liquid chromatography (RP-DAD-HPLC) method for the quantification of Incensole and Incensole acetate is reported, indicating that these two compounds are typical biomarkers for B. papyrifera.

Protective effects of incensole acetate on cerebral ischemic injury.[Pubmed:22284622]

Brain Res. 2012 Mar 14;1443:89-97.

The resin of Boswellia species is a major anti-inflammatory agent that has been used for centuries to treat various conditions including injuries and inflammatory conditions. Incensole acetate (IA), a major constituent of this resin, has been shown to inhibit NF-kappaB activation and concomitant inflammation, as well as the neurological deficit following head trauma. Here, we show that IA protects against ischemic neuronal damage and reperfusion injury in mice, attenuating the inflammatory nature of ischemic damage. IA given post-ischemia, reduced infarct volumes and improved neurological activities in the mouse model of ischemic injury in a dose dependent fashion. The protection from damage was accompanied by inhibition of TNF-alpha, IL-1beta and TGF-beta expression, as well as NF-kappaB activation following injury. In addition, IA is shown to have a therapeutic window of treatment up to 6h after ischemic injury. Finally, the protective effects of IA were partially mediated by TRPV3 channels as determined by the TRPV3 deficient mice and channel blocker studies. This study suggests that the anti-inflammatory and neuroprotective activities of IA may serve as a novel therapeutic treatment for ischemic and reperfusion injury, and as a tool in the ongoing research of mechanisms for neurological damage.

A thin-layer chromatography method for the identification of three different olibanum resins (Boswellia serrata, Boswellia papyrifera and Boswellia carterii, respectively, Boswellia sacra).[Pubmed:21858880]

Phytochem Anal. 2012 Mar-Apr;23(2):184-9.

INTRODUCTION: Resins of the genus Boswellia are currently an interesting topic for pharmaceutical research since several pharmacological activities (e.g. anti-inflammatory, anti-microbial, anti-tumour) are reported for extracts and compounds isolated from them. Unambiguous identification of these resins, by simple and convenient analytical methods, has so far not clearly been verified. OBJECTIVE: For differentiation and identification of three important Boswellia species (Boswellia serrata Roxb., Boswellia papyrifera Hochst. and Boswellia carterii Birdw., respectively Boswellia sacra Flueck.), possible even for minimally equipped laboratories, a thin-layer chromatography (TLC) method was developed, allowing unambiguous identification of the three species. METHODOLOGY: Crude resin samples (commercial samples and a voucher specimen) were extracted with methanol or diethyl ether and subjected to TLC analysis (normal phase). A pentane and diethyl ether (2:1) with 1% acetic acid eluent was used. Chromatograms were analysed by UV detection (254 nm) and dyeing with anisaldehyde dyeing reagent. Significant spots were isolated and structures were assigned (mass spectrometry; nuclear magnetic resonance spectroscopy). RESULTS: Incensole and Incensole acetate are specific biomarkers for Boswellia papyrifera. Boswellia carterii/Boswellia sacra reveal ss-caryophyllene oxide as a significant marker compound. Boswellia serrata shows neither Incensole acetate nor ss-caryophyllene oxide spots, but can be identified by a strong serratol and a sharp 3-oxo-8,24-dien-tirucallic acid spot. CONCLUSION: The TLC method developed allows unambiguous identification of three different olibanum samples (Boswellia papyrifera, Boswellia serrata, Boswellia carterii/Boswellia sacra). Evidence on the specific biosynthesis routes of these Boswellia species is reported.

Incensole, a 14-membered diterpenoid, is isolated from both essential oils and resins of frankincense. Incensole has shown anti-inflammatory and anti-depression activities due to their ability to activate ion channels in the brain to alleviate anxiety or depression.

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