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commiphora_erythraea_ehrenb._engl [2016/07/03 21:11] andreas |
commiphora_erythraea_ehrenb._engl [2021/03/05 14:14] andreas |
Commiphora erythraea (Ehrenb.) Engl. - Burseraceae - agarsu, opopanax | Commiphora erythraea (Ehrenb.) Engl. - Burseraceae - agarsu, bisabol myrrh, opopanax, **Bisabol-Myrrhe**, Bisabol-Opopanax, |
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Tree, native to Somalia. | Small tree, native to Somalia. |
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| "A number of oleo-gum-resins called bdelliums are produced in Arabia and Somalia from various species of |
| Commiphora and resemble myrrh; these were probably counted as myrrh in classical times and are probably used for adulteration today. The 'perfumed bdellium' (opopanax or bisabol myrrh) is from C. erythraea... \\ |
| C.erythraea and C. kataf, the main sources of opopanax, are abundant in many parts of southern Arabia, Somalia, eastern Ethiopia and Kenya." \\ |
| Opopanax resin oil has been found to contain α-bisabolene, β-bisabolene, and γ-bisabolene, α-bergamotene, γ-cadinene, δ-cadinene, ar-curcumene and α-santalene, but the results are not consistent. (Z)-α-bisabolene remotely recalls the typical odour of opopanax. \\ |
| [Myrrh-commiphora chemistry., Hanuš, L.O., Řezanka, T., Dembitsky, V.M., Moussaieff, A., Biomedical papers, 149(1), 2005, 3-28; and literature cited therein] [[http://jonnsaromatherapy.com/pdf/GC-MS_Commiphora_various_2005.pdf]] |
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| "Opopanax oil and opopanax resinoid are obtained from the resin of Commiphora erythraea Engl. var. glabrescens Engl., a tree growing in Somalia (Burseraceae). The resinoid is prepared by solvent extraction, and steam distillation of the resin gives the essential oil, which is a yellow to greenish-yellow liquid with a warm, sweet, balsamic odor... Opopanax oil and resinoid are used in perfume compositions with oriental characteristics, the resinoid also for its fixative properties." \\ |
| [H. Surburg und J. Panten: Common Fragrance and Flavor Materials: preparation, properties, and uses. Wiley-VCH, Weinheim 2006, 221] |
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| |{{:bisabolene_Zalpha.jpg| (Z)-α-bisabolene }} \\ (Z)-α-bisabolene |{{:furanodien-6-one.jpg| 1(10),4-furanodien-6-one }} \\ 1(10),4-furanodien-6-one |{{:dihydropyrocurzerenone.jpg|dihydropyrocurzerenone}} \\ dihydropyrocurzerenone \\ //(resinous, myrrh-like)// | |
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The resin essential oil of C. erythraea obtained by steam distillation contained two furanosesquiterpenoids as dominant constituents, 1(10),4-furanodien-6-one (21.5%), and 1,10(15)-furanogermacradien-6-one (14.3%), together with rel-3R-methoxy-4S-furanogermacra-1E,10(15)-dien-6-one (7.4%) and rel-2R-methoxy-4R-furanogermacra-1(10)E-en-6-one (3.9%). Minor components were eg. aromadendrene (4.4%), α-gurjunene (3.8%) and α-copaene (3.4%). "In our oil, we could not identify either ocimene, although this was the most abundant monoterpene of the opopanax oil studied by Ikeda, or α- and β-bisabolenes." \\ | The resin essential oil of C. erythraea obtained by steam distillation contained two furanosesquiterpenoids as dominant constituents, 1(10),4-furanodien-6-one (21.5%), and 1,10(15)-furanogermacradien-6-one (14.3%), together with rel-3R-methoxy-4S-furanogermacra-1E,10(15)-dien-6-one (7.4%) and rel-2R-methoxy-4R-furanogermacra-1(10)E-en-6-one (3.9%). Minor components were eg. aromadendrene (4.4%), α-gurjunene (3.8%) and α-copaene (3.4%). "In our oil, we could not identify either ocimene, although this was the most abundant monoterpene of the opopanax oil studied by Ikeda, or α- and β-bisabolenes." \\ |
[Chemical composition of the essential oil of Commiphora erythraea., Marcotullio, M.C., Santi, C., Mwankie, G., Curini, M., Natural product communications, 4(12), 2009, 1751-4] | [Chemical composition of the essential oil of Commiphora erythraea., Marcotullio, M.C., Santi, C., Mwankie, G., Curini, M., Natural product communications, 4(12), 2009, 1751-4] |
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| „In all the oils and extracts, furanodienone [1(10),4-furanogermacradien-6-one] resulted the most abundant compound along with 1,10(15)-furanogermacra-dien-6-one, 3-methoxy-furanogermacra-1E,10(15)-dien-6-one, 2- methoxy-furanogermacra-1(10)E-en-6-one, 1,2-epoxy- furanogermacr-10(15)-en-6-one, dihydropyrocurzerenone, agarsenone, myrrhone, curzerenone, furanoeudesma-1,4-dien-6-one and alismol. Agarsenone showed to be unstable in chlorinated solvents, giving rise in short time, to mirrhone, and, by autoxidation, to agarsenolides…“ \\ |
| [Marcotullio, Maria Carla, Ornelio Rosati, and Daniela Lanari. "Phytochemistry of Commiphora erythraea: A Review." Natural Product Communications 13.9 (2018): 1934578X1801300925] \\ |
| [[https://journals.sagepub.com/doi/pdf/10.1177/1934578X1801300925]] |
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The hexan extract of Commiphora erythraea (Ehrenb.) Engl. resin showed topical anti-inflammatory, free radical scavenging, antifungal activities and antioxidant activities. Bioguided separation of the extract led to furanosesquiterpenoids as active constituents. \\ | The hexan extract of Commiphora erythraea (Ehrenb.) Engl. resin showed topical anti-inflammatory, free radical scavenging, antifungal activities and antioxidant activities. Bioguided separation of the extract led to furanosesquiterpenoids as active constituents. \\ |
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"Furanodienone and 1,10(15)-furanogermacra-dien-6-ones showed to be potent inhibitors of lipid peroxidation (IC 50 of ~0.087 μM), being more active than the methoxylated analogues. Furthermore, using BV2 microglial cells, we found that furanodienone from C. erythraea is able to counteract LPS-induced cell death and decrease LPS-induced NO generation thus protecting microglial cells from LPS-induced cytotoxicity." \\ [Protective effects of Commiphora erythraea resin constituents against cellular oxidative damage., Marcotullio, M.C., Messina, F., Curini, M., Macchiarulo, A., Cellanetti, M., Ricci, D., Bellezza, I., Molecules, 16(12), 2011, 10357-10369] | "Furanodienone and 1,10(15)-furanogermacra-dien-6-ones showed to be potent inhibitors of lipid peroxidation (IC 50 of ~0.087 μM), being more active than the methoxylated analogues. Furthermore, using BV2 microglial cells, we found that furanodienone from C. erythraea is able to counteract LPS-induced cell death and decrease LPS-induced NO generation thus protecting microglial cells from LPS-induced cytotoxicity." \\ [Protective effects of Commiphora erythraea resin constituents against cellular oxidative damage., Marcotullio, M.C., Messina, F., Curini, M., Macchiarulo, A., Cellanetti, M., Ricci, D., Bellezza, I., Molecules, 16(12), 2011, 10357-10369] |
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{{:furanodien-6-one.jpg| 1(10),4-furanodien-6-one }} 1(10),4-furanodien-6-one | |
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The vitro anti-inflammatory activity of 1(10),4-furanodien-6-one was shown by exposing microglial BV-2 cells to lipopolysaccharide. Pre-treatement with this furanodien-6-one restored cell viability and ROS to control levels while halving NO generation; production of pro-inflammatory IL-6, IL-23, IL-17, TGF-β, and INF-γ, significantly induced by LPS, was also markedly reduced. 1(10),4-furanodien-6-one protected primary neuronal cultures against the inflammatory/toxic insults of LPS-treated BV-2 conditioned media, indicating anti-inflammatory/cytoprotective effects in neuronal cells. In adult mice ip-injected with LPS, 1(10),4-furanodien-6-one had strong cerebral anti-inflammatory properties by inhibiting liver and brain TNFα as well as IL-1β expression. The results provide strong evidence that 1(10),4-furanodien-6-one could be exploited to counteract degenerative pathologies based on neuroinflammation. \\ | The vitro anti-inflammatory activity of 1(10),4-furanodien-6-one was shown by exposing microglial BV-2 cells to lipopolysaccharide. Pre-treatement with this furanodien-6-one restored cell viability and ROS to control levels while halving NO generation; production of pro-inflammatory IL-6, IL-23, IL-17, TGF-β, and INF-γ, significantly induced by LPS, was also markedly reduced. 1(10),4-furanodien-6-one protected primary neuronal cultures against the inflammatory/toxic insults of LPS-treated BV-2 conditioned media, indicating anti-inflammatory/cytoprotective effects in neuronal cells. In adult mice ip-injected with LPS, 1(10),4-furanodien-6-one had strong cerebral anti-inflammatory properties by inhibiting liver and brain TNFα as well as IL-1β expression. The results provide strong evidence that 1(10),4-furanodien-6-one could be exploited to counteract degenerative pathologies based on neuroinflammation. \\ |