Incensole: Difference between revisions
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=== Biosynthetic Pathway === |
=== Biosynthetic Pathway === |
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It has been proposed that Incensole is produced in ''[[Boswellia]]'' plants via Serratol from [[Geranylgeranyl pyrophosphate|Geranylgeranyl Pyrophosphate]] (GGPP)<ref name=": |
It has been proposed that Incensole is produced in ''[[Boswellia]]'' plants via Serratol from [[Geranylgeranyl pyrophosphate|Geranylgeranyl Pyrophosphate]] (GGPP)<ref name=":7" />, a C<sub>20</sub> precursor for many metabolic branches such as the [[Chlorophyll]], [[Carotenoid]], and [[Gibberellin]] biosynthetic pathways<ref>{{Cite journal |last=Zhou |first=Fei |last2=Wang |first2=Cheng-Yuan |last3=Gutensohn |first3=Michael |last4=Jiang |first4=Ling |last5=Zhang |first5=Peng |last6=Zhang |first6=Dabing |last7=Dudareva |first7=Natalia |last8=Lu |first8=Shan |date=2017-06-27 |title=A recruiting protein of geranylgeranyl diphosphate synthase controls metabolic flux toward chlorophyll biosynthesis in rice |url=https://pnas.org/doi/full/10.1073/pnas.1705689114 |journal=Proceedings of the National Academy of Sciences |language=en |volume=114 |issue=26 |pages=6866–6871 |doi=10.1073/pnas.1705689114 |issn=0027-8424 |pmc=PMC5495272 |pmid=28607067}}</ref>. To begin, GGPP loses its pyrophosphate group enabling it to be 1,14-cyclized to form Cembrene after the loss of a proton. Cembrene is then hydrolyzed to form Serratol which in turn undergoes epoxidation and intramolecular cyclization to form Incensole<ref name=":7" />. Though this makes sense chemically, and has been used synthetically to make Incensole<ref name=":6" />, the incongruent abundances of Incensole, Serratol, Incensole Acetate, and Iso-serratol in the ''Boswellia'' species which are known to produce Incensole indicates that this pathway is somewhat improbable to occur<ref name=":7" />. |
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== Biological Sources == |
== Biological Sources == |
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[[File:Incenso-1.jpg|alt=Frankincense resin seeping out of B. sacra trunk|thumb|Frankincense resin seeping out of ''B. sacra'' trunk]] |
[[File:Incenso-1.jpg|alt=Frankincense resin seeping out of B. sacra trunk|thumb|Frankincense resin seeping out of ''B. sacra'' trunk]] |
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Incensole is mainly found in the resin of ''[[Boswellia]]'' trees which grow in a region across Northern Africa from [[Ethiopia]] to [[Nigeria]]<ref name=":2">{{Cite web |title=African Plant Database |url=https://africanplantdatabase.ch/en/nomen/7737 |access-date=2023-05-01 |website=africanplantdatabase.ch}}</ref>. ''[[Boswellia]]'' trees prefer to grow in arid, stony regions<ref name=":2" />, and cuts to the body of the trees seep [[frankincense]] resin which hardens and darkens when exposed to the air<ref name=":3">R Michael Buch and Joseph A von Fraunhofer. “The Systemic and Brain Health Benefits of Frankincense”. EC Psychology and Psychiatry 9.5 (2020): 50-53.</ref>. Incensole is a biomarker of frankincense from certain ''Boswellia'' species; these species are ''[[Boswellia papyrifera|B. papyrifera]]'', ''B. occulta, B. carteri,'' ''[[Boswellia sacra|B. sacra]]''<ref>{{Cite web |title=Extraction of Frankincense Resins - Bangor University |url=https://research.bangor.ac.uk/portal/en/theses/extraction-of-frankincense-resins(6fb57404-e388-4d12-a9f5-7603dd1ab6ba).html |access-date=2023-05-01 |website=research.bangor.ac.uk |language=en}}</ref><ref name=":4">{{Cite journal |last=Al-Yasiry |first=Ali Ridha Mustafa |last2=Kiczorowska |first2=Bożena |date=2016-01-04 |title=Frankincense – therapeutic properties |url=https://publisherspanel.com/icid/1200553 |journal=Postępy Higieny i Medycyny Doświadczalnej |volume=70 |pages=380–391 |doi=10.5604/17322693.1200553 |issn=1732-2693}}</ref><ref name=":5">{{Cite journal |last=Michie |first=C A |last2=Cooper |first2=E |date=1991-10 |title=Frankincense and Myrrh as Remedies in Children |url=http://journals.sagepub.com/doi/10.1177/014107689108401011 |journal=Journal of the Royal Society of Medicine |language=en |volume=84 |issue=10 |pages=602–605 |doi=10.1177/014107689108401011 |issn=0141-0768 |pmc=PMC1295557 |pmid=1744842 |
Incensole is mainly found in the resin of ''[[Boswellia]]'' trees which grow in a region across Northern Africa from [[Ethiopia]] to [[Nigeria]]<ref name=":2">{{Cite web |title=African Plant Database |url=https://africanplantdatabase.ch/en/nomen/7737 |access-date=2023-05-01 |website=africanplantdatabase.ch}}</ref>. ''[[Boswellia]]'' trees prefer to grow in arid, stony regions<ref name=":2" />, and cuts to the body of the trees seep [[frankincense]] resin which hardens and darkens when exposed to the air<ref name=":3">R Michael Buch and Joseph A von Fraunhofer. “The Systemic and Brain Health Benefits of Frankincense”. EC Psychology and Psychiatry 9.5 (2020): 50-53.</ref>. Incensole is a biomarker of frankincense from certain ''Boswellia'' species; these species are ''[[Boswellia papyrifera|B. papyrifera]]'', ''B. occulta, B. carteri,'' ''[[Boswellia sacra|B. sacra]]''<ref name=":9" /><ref>{{Cite web |title=Extraction of Frankincense Resins - Bangor University |url=https://research.bangor.ac.uk/portal/en/theses/extraction-of-frankincense-resins(6fb57404-e388-4d12-a9f5-7603dd1ab6ba).html |access-date=2023-05-01 |website=research.bangor.ac.uk |language=en}}</ref><ref name=":4">{{Cite journal |last=Al-Yasiry |first=Ali Ridha Mustafa |last2=Kiczorowska |first2=Bożena |date=2016-01-04 |title=Frankincense – therapeutic properties |url=https://publisherspanel.com/icid/1200553 |journal=Postępy Higieny i Medycyny Doświadczalnej |volume=70 |pages=380–391 |doi=10.5604/17322693.1200553 |issn=1732-2693}}</ref><ref name=":5">{{Cite journal |last=Michie |first=C A |last2=Cooper |first2=E |date=1991-10 |title=Frankincense and Myrrh as Remedies in Children |url=http://journals.sagepub.com/doi/10.1177/014107689108401011 |journal=Journal of the Royal Society of Medicine |language=en |volume=84 |issue=10 |pages=602–605 |doi=10.1177/014107689108401011 |issn=0141-0768 |pmc=PMC1295557 |pmid=1744842}}</ref>'','' and possibly ''B. serrata'' though there are conflicting results as to whether it really produces incensole<ref name=":7" />. It should be noted that ''B. carteri'' and ''[[Boswellia sacra|B. sacra]]'' have been determined to actually be the same species, except that ''B. carteri'' is native to Africa while ''B. sacra'' is native to South Arabia.<ref name=":7" /> |
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It has also been proposed that Incensole and Incensole Acetate can be derived from other sources such as these<ref name=": |
It has also been proposed that Incensole and Incensole Acetate can be derived from other sources such as these<ref name=":7" />: |
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* [[Coriander]] (''Coriandrum savitum'') |
* [[Coriander]] (''Coriandrum savitum'') |
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* Doum Palm (''[[Hyphaene thebaica]])'' |
* Doum Palm (''[[Hyphaene thebaica]])'' |
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But no isolation or structural identification tests were run to identify Incensole in these specimen than [[Gas chromatography–mass spectrometry|gas chromatography and mass spectrometry]]. Thus incensole/incensole acetate has not been conclusively identified in any of these species<ref name=": |
But no isolation or structural identification tests were run to identify Incensole in these specimen than [[Gas chromatography–mass spectrometry|gas chromatography and mass spectrometry]]. Thus incensole/incensole acetate has not been conclusively identified in any of these species<ref name=":7" />. |
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== Derivation and Characterization == |
== Derivation and Characterization == |
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[[File:Mass_Spectrum_of_Incensole.png|thumb|257x257px|Deconvoluted mass spectrum of Incensole from Incensole and Serratol total ion count peak. RT of 24.02 min. (Baeten ''et al.'' 2014)]] |
[[File:Mass_Spectrum_of_Incensole.png|thumb|257x257px|Deconvoluted mass spectrum of Incensole from Incensole and Serratol total ion count peak. RT of 24.02 min. (Baeten ''et al.'' 2014)]] |
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Incensole was originally isolated in 1966 by S. Corsano and R. Nicoletti using several ether extractions and vacuum separations, and then characterized using [[Ultraviolet–visible spectroscopy|UV-Vis]], [[Infrared spectroscopy|IR]], and [[Proton nuclear magnetic resonance|H-NMR]] spectroscopy. They found Incensole to have no UV-Vis absorption above 210 mμ<ref name=": |
Incensole was originally isolated in 1966 by S. Corsano and R. Nicoletti using several ether extractions and vacuum separations, and then characterized using [[Ultraviolet–visible spectroscopy|UV-Vis]], [[Infrared spectroscopy|IR]], and [[Proton nuclear magnetic resonance|H-NMR]] spectroscopy. They found Incensole to have no UV-Vis absorption above 210 mμ<ref name=":8" />. The distinguishing IR and H-NMR peaks of Incensole are reported in the tables below<ref name=":8" />, and the observed mass spectrogram of Incensole from a study done in 2014 on frankincense in incense pots is pictured to the right<ref name=":10">{{Cite journal |last=Baeten |first=Jan |last2=Deforce |first2=Koen |last3=Challe |first3=Sophie |last4=Vos |first4=Dirk De |last5=Degryse |first5=Patrick |date=2014-11-12 |title=Holy Smoke in Medieval Funerary Rites: Chemical Fingerprints of Frankincense in Southern Belgian Incense Burners |url=https://journals.plos.org/plosone/article?id=10.1371/journal.pone.0113142 |journal=PLOS ONE |language=en |volume=9 |issue=11 |pages=e113142 |doi=10.1371/journal.pone.0113142 |issn=1932-6203 |pmc=PMC4229304 |pmid=25391130}}</ref>. |
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{| class="wikitable" |
{| class="wikitable" |
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|+IR Peaks of Incensole |
|+IR Peaks of Incensole<ref name=":8" /> |
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!Wave Number (cm<sup>-1</sup>) |
!Wave Number (cm<sup>-1</sup>) |
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!Peak Identity |
!Peak Identity |
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|} |
|} |
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{| class="wikitable" |
{| class="wikitable" |
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|+NMR Peaks of Incensole in CCl<sub>4</sub> at 60 Mc<ref name=": |
|+NMR Peaks of Incensole in CCl<sub>4</sub> at 60 Mc<ref name=":8" /> |
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!Chemical Shift (ppm) |
!Chemical Shift (ppm) |
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!Protons<ref>{{Cite web |date=December 2013 |title=NMR Guidelines for ACS Journals |url=https://pubsapp.acs.org/paragonplus/submission/acs_nmr_guidelines.pdf |url-status=live |access-date=23 May 2023 |website=American Chemical Society}}</ref> |
!Protons<ref>{{Cite web |date=December 2013 |title=NMR Guidelines for ACS Journals |url=https://pubsapp.acs.org/paragonplus/submission/acs_nmr_guidelines.pdf |url-status=live |access-date=23 May 2023 |website=American Chemical Society}}</ref> |
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| Line 106: | Line 106: | ||
|CH<sub>3</sub>CH=C(CH<sub>3</sub>)<sub>2</sub> |
|CH<sub>3</sub>CH=C(CH<sub>3</sub>)<sub>2</sub> |
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|} |
|} |
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Incensole is most often extracted by chromatographic extractions and [[Steam distillation|hydrodistillations]], which produce a frankincense essential oil. Characterization usually occurs by [[Gas chromatography–mass spectrometry|GC/MS]] although [[Thin-layer chromatography|TLC]] has also been used and [[Near-infrared spectroscopy|NIR]] spectroscopy<ref>{{Cite journal |last=Al-Shidhani |first=Sulaiman |last2=Rehman |first2=Najeeb Ur |last3=Mabood |first3=Fazal |last4=Al-Broumi |first4=Muhammed |last5=Hussain |first5=Hidayat |last6=Hussain |first6=Javid |last7=Csuk |first7=Rene |last8=Al-Harrasi |first8=Ahmed |date=2018-05 |title=Quantification of Incensole in Three Boswellia Species by NIR Spectroscopy Coupled with PLSR and Cross-Validation by HPLC: Quantification of incensole in Boswellia species by NIRS and HPLC |url=https://onlinelibrary.wiley.com/doi/10.1002/pca.2743 |journal=Phytochemical Analysis |language=en |volume=29 |issue=3 |pages=300–307 |doi=10.1002/pca.2743}}</ref> is being optimized to provide fast and accurate characterization.<ref name=": |
Incensole is most often extracted by chromatographic extractions and [[Steam distillation|hydrodistillations]], which produce a frankincense essential oil. Characterization usually occurs by [[Gas chromatography–mass spectrometry|GC/MS]] although [[Thin-layer chromatography|TLC]] has also been used and [[Near-infrared spectroscopy|NIR]] spectroscopy<ref>{{Cite journal |last=Al-Shidhani |first=Sulaiman |last2=Rehman |first2=Najeeb Ur |last3=Mabood |first3=Fazal |last4=Al-Broumi |first4=Muhammed |last5=Hussain |first5=Hidayat |last6=Hussain |first6=Javid |last7=Csuk |first7=Rene |last8=Al-Harrasi |first8=Ahmed |date=2018-05 |title=Quantification of Incensole in Three Boswellia Species by NIR Spectroscopy Coupled with PLSR and Cross-Validation by HPLC: Quantification of incensole in Boswellia species by NIRS and HPLC |url=https://onlinelibrary.wiley.com/doi/10.1002/pca.2743 |journal=Phytochemical Analysis |language=en |volume=29 |issue=3 |pages=300–307 |doi=10.1002/pca.2743}}</ref> is being optimized to provide fast and accurate characterization.<ref name=":7" /> |
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Unfortunately, within some of the earlier literature, frankincense biomarker compositions have been misattributed to different ''Boswellia'' species, as was seen in the mistaken attribution of Incensole being first extracted from a ''B. carteri'' specimen when it likely came from a ''B. papyrifera'' specimen. This likely comes from the use of faulty or absent taxonomic certifications when determining the specimen identities of frankincense purchased from market as opposed to collected straight from the tree.<ref name=": |
Unfortunately, within some of the earlier literature, frankincense biomarker compositions have been misattributed to different ''Boswellia'' species, as was seen in the mistaken attribution of Incensole being first extracted from a ''B. carteri'' specimen when it likely came from a ''B. papyrifera'' specimen. This likely comes from the use of faulty or absent taxonomic certifications when determining the specimen identities of frankincense purchased from market as opposed to collected straight from the tree.<ref name=":7" /> |
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== Incensole in Archaeology == |
== Incensole in Archaeology == |
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Frankincense has been used for thousands of years in religious ceremonies and for medicinal purposes<ref name=": |
Frankincense has been used for thousands of years in religious ceremonies and for medicinal purposes<ref name=":0" />. In fact, by tracing incensole's degraded products, historians have been able to use it to understand the historical use of incense in religion. In one such case, the examination of incensole as a biomarker led to the confirmation of certain porous pots buried in Medieval, Belgian, Christian graves as incense burners. Further study indicated that though frankincense was a main component of funerary incense at the time, other, cheaper local resins were mixed into the incense, possibly to reduce cost<ref name=":10" />. |
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Additionally, frankincense has been used for thousands of years as a medicine. It is listed in texts such as the [[Ebers Papyrus|Papyrus Ebers]] and the Syriac book of medicine and was prescribed by the practitioners [[Celsus]] and [[Nicholas Culpeper|Culpepper]] as a remedy for a variety of ailments from stomach ulcers and gastrointestinal hemorrhages to [[gout]] and open wounds<ref name=": |
Additionally, frankincense has been used for thousands of years as a medicine. It is listed in texts such as the [[Ebers Papyrus|Papyrus Ebers]] and the Syriac book of medicine and was prescribed by the practitioners [[Celsus]] and [[Nicholas Culpeper|Culpepper]] as a remedy for a variety of ailments from stomach ulcers and gastrointestinal hemorrhages to [[gout]] and open wounds<ref name=":5" />. Modern analysis on the medical efficacy of frankincense has elucidated Incensole and Incensole Acetate along with [[Boswellic acid|Boswellic Acids]] as being the main active ingredients in frankincense<ref name=":0" />. |
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Due to its religious and medicinal significance, frankincense and its biomarker components, like Incensole, can be found all over the world in Europe, Asia, the Mediterranean, and the Middle East<ref name=": |
Due to its religious and medicinal significance, frankincense and its biomarker components, like Incensole, can be found all over the world in Europe, Asia, the Mediterranean, and the Middle East<ref name=":0" /><ref name=":5" /><ref>{{Cite journal |last=Gebrehiwot |first=K. |last2=Muys |first2=B. |last3=Haile |first3=M. |last4=Mitloehner |first4=R. |date=2003-12 |title=Introducing Boswellia papyrifera (Del.) Hochst and its non-timber forest product, frankincense |url=http://dx.doi.org/10.1505/ifor.5.4.348.22661 |journal=International Forestry Review |volume=5 |issue=4 |pages=348–353 |doi=10.1505/ifor.5.4.348.22661 |issn=1465-5489}}</ref> as a result of global trade. |
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== Medicinal Properties == |
== Medicinal Properties == |
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Previously, the therapeutic properties of frankincense had been attributed to [[Boswellic acid|Boswellic acids]] within the resin, but research from 2019 and 2020 has found Incensole and its acetate ether to be major contributors to frankincense's therapeutic efficacy<ref name=": |
Previously, the therapeutic properties of frankincense had been attributed to [[Boswellic acid|Boswellic acids]] within the resin, but research from 2019 and 2020 has found Incensole and its acetate ether to be major contributors to frankincense's therapeutic efficacy<ref name=":0" />. This research has found Incensole to act as an anti-inflammatory and neuroprotective compound after murine head-trauma on top of exhibiting [[anxiolytic]], anti-depressive, and sedative effects in mice<ref name=":0" />. |
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It is proposed that Incensole works as an anti-inflammatory through the inhibition of the [[NF-κB]] pathway which is responsible for the increased production of proinflammatory proteins. Insensitivity in the NF-κB pathway is correlated to arthritis, asthma, [[inflammatory bowel disease]], [[Ataxia–telangiectasia|ataxia telangiectasia]], cancers, and neurodegenerative diseases<ref name=": |
It is proposed that Incensole works as an anti-inflammatory through the inhibition of the [[NF-κB]] pathway which is responsible for the increased production of proinflammatory proteins. Insensitivity in the NF-κB pathway is correlated to arthritis, asthma, [[inflammatory bowel disease]], [[Ataxia–telangiectasia|ataxia telangiectasia]], cancers, and neurodegenerative diseases<ref name=":0" /><ref name=":4" /><ref>{{Cite journal |last=Moussaieff |first=Arieh |last2=Shohami |first2=Esther |last3=Kashman |first3=Yoel |last4=Fride |first4=Ester |last5=Schmitz |first5=M. Lienhard |last6=Renner |first6=Florian |last7=Fiebich |first7=Bernd L. |last8=Munoz |first8=Eduardo |last9=Ben-Neriah |first9=Yinon |last10=Mechoulam |first10=Raphael |date=2007-12-01 |title=Incensole Acetate, a Novel Anti-Inflammatory Compound Isolated from Boswellia Resin, Inhibits Nuclear Factor-κB Activation |url=https://molpharm.aspetjournals.org/content/72/6/1657 |journal=Molecular Pharmacology |language=en |volume=72 |issue=6 |pages=1657–1664 |doi=10.1124/mol.107.038810 |issn=0026-895X |pmid=17895408}}</ref>. |
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It has also been found that Incensole Acetate activates the [[TRPV3]] channel<ref name=": |
It has also been found that Incensole Acetate activates the [[TRPV3]] channel<ref name=":0" /> which, among other things, is responsible for regulating wound healing and the perception of pain and itching<ref>{{Citation |last=Yang |first=Pu |title=TRPV3 |date=2014 |url=https://doi.org/10.1007/978-3-642-54215-2_11 |work=Mammalian Transient Receptor Potential (TRP) Cation Channels: Volume I |pages=273–291 |editor-last=Nilius |editor-first=Bernd |access-date=2023-05-01 |place=Berlin, Heidelberg |publisher=Springer |language=en |doi=10.1007/978-3-642-54215-2_11#abs1 |isbn=978-3-642-54215-2 |last2=Zhu |first2=Michael X. |editor2-last=Flockerzi |editor2-first=Veit}}</ref>. It has been thought that this is another key component of Incensole's role as an anti-inflammatory. |
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Incensole has also been cited as a potential antibacterial against [[Bacillus]]<ref name=": |
Incensole has also been cited as a potential antibacterial against [[Bacillus]]<ref name=":4" />. |
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== References == |
== References == |
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Revision as of 05:02, 24 May 2023
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| Names | |
|---|---|
| IUPAC name
(1R,2R,5E,9Z)-1,5,9-trimethyl-12-propan-2-yl-15-oxabicyclo[10.2.1]pentadeca-5,9-dien-2-ol
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C20H34O2 | |
| Molar mass | 306.490 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Incensole is a C20 diterpene alcohol and biomarker for some plants of the Boswellia genus. It, along with its acetate ester Incensole Acetate, is an abundant component of frankincense, the resin collected from Boswellia trees[1]. Incensole is used archaeologically to assist in identifying trade routes and distinguishing the identity of frankincense from other resins which may have been used together in incense and other salves. Incensole has also been deemed to be an active component in medicinal frankincense[1].
Background
Incensole was first isolated in 1966 at the Institute of Organic Chemistry at the University of Rome by S. Corsano and R. Nicoletti while investigating the neutral components of Boswellia carteri resin[2], though it is believed that the sample was likely actually from an "Eritrea" type B. papyrifera specimen[3]. In 2005 Incensole was used as a biomarker for frankincense (or olibanum) in order to determine the composition of Ancient Egyptian mummification balms and unguents[4], speaking to its role in studying the history religion.
Frankincense roots its historical significance in its global medicinal use and it's religious and ceremonial use as a component of incense. It's been used for thousands of years in religious ceremonies of all kinds and is notably one of the three gifts the magi presented to the baby Jesus in the Bible.
Chemistry
Oily in appearance, incensole has a low volatility. It can be synthetically prepared from Cembrene[5], a terpenoid, and Cembrenol (Serratol), its biologic precursor[5]. Diterpenes and terpenoids are classes of biomarkers which are synthesized in plants and have been found in insects[6], possibly because of accumulation of terpenoids within their diets[7]. Terpenoids have gained special interest due to their potential as anti-inflammatories, anti-carcinogens, and antiparasitics[6].
Biosynthetic Pathway
It has been proposed that Incensole is produced in Boswellia plants via Serratol from Geranylgeranyl Pyrophosphate (GGPP)[3], a C20 precursor for many metabolic branches such as the Chlorophyll, Carotenoid, and Gibberellin biosynthetic pathways[8]. To begin, GGPP loses its pyrophosphate group enabling it to be 1,14-cyclized to form Cembrene after the loss of a proton. Cembrene is then hydrolyzed to form Serratol which in turn undergoes epoxidation and intramolecular cyclization to form Incensole[3]. Though this makes sense chemically, and has been used synthetically to make Incensole[5], the incongruent abundances of Incensole, Serratol, Incensole Acetate, and Iso-serratol in the Boswellia species which are known to produce Incensole indicates that this pathway is somewhat improbable to occur[3].
Biological Sources
Incensole is mainly found in the resin of Boswellia trees which grow in a region across Northern Africa from Ethiopia to Nigeria[9]. Boswellia trees prefer to grow in arid, stony regions[9], and cuts to the body of the trees seep frankincense resin which hardens and darkens when exposed to the air[10]. Incensole is a biomarker of frankincense from certain Boswellia species; these species are B. papyrifera, B. occulta, B. carteri, B. sacra[4][11][12][13], and possibly B. serrata though there are conflicting results as to whether it really produces incensole[3]. It should be noted that B. carteri and B. sacra have been determined to actually be the same species, except that B. carteri is native to Africa while B. sacra is native to South Arabia.[3]
It has also been proposed that Incensole and Incensole Acetate can be derived from other sources such as these[3]:
- Coriander (Coriandrum savitum)
- Water Dropwort (Oenanthe javanica)
- Kacip Fatimah (Labisia pumila)
- Mandarin Orange (Citrus reticulata)
- Curry Flowers (Helichrysum italicum)
- Sage Leaves (Salvia officinalis, Salvia oligophylla)
- Pink Rock-Rose (Cistus creticus)
- Desert Horse-Purslane (Trianthema portulacastrum)
- Alder Buckthorn (Frangula alnus)
- Doum Palm (Hyphaene thebaica)
But no isolation or structural identification tests were run to identify Incensole in these specimen than gas chromatography and mass spectrometry. Thus incensole/incensole acetate has not been conclusively identified in any of these species[3].
Derivation and Characterization
Incensole was originally isolated in 1966 by S. Corsano and R. Nicoletti using several ether extractions and vacuum separations, and then characterized using UV-Vis, IR, and H-NMR spectroscopy. They found Incensole to have no UV-Vis absorption above 210 mμ[2]. The distinguishing IR and H-NMR peaks of Incensole are reported in the tables below[2], and the observed mass spectrogram of Incensole from a study done in 2014 on frankincense in incense pots is pictured to the right[14].
| Wave Number (cm-1) | Peak Identity |
|---|---|
| 3620 | -OH |
| 1670 | C=C |
| 1375, 1390 | CH3-C-CH3 |
| 1050 | C-O |
| Chemical Shift (ppm) | Protons[15] | Group Identity |
|---|---|---|
| 0.90 | (d, 6H, J = 6.5 c/s) | isopropyl |
| 1.02 | (s, 3H) | CH3-C-O |
| 1.48, 1.61 | (s, 3H) | CH3-C= |
| 3.18 | (d, 1H, J = 10 c/s) | HC-OH |
| 5.06 | (2H, broad signal) | CH3CH=C(CH3)2 |
Incensole is most often extracted by chromatographic extractions and hydrodistillations, which produce a frankincense essential oil. Characterization usually occurs by GC/MS although TLC has also been used and NIR spectroscopy[16] is being optimized to provide fast and accurate characterization.[3]
Unfortunately, within some of the earlier literature, frankincense biomarker compositions have been misattributed to different Boswellia species, as was seen in the mistaken attribution of Incensole being first extracted from a B. carteri specimen when it likely came from a B. papyrifera specimen. This likely comes from the use of faulty or absent taxonomic certifications when determining the specimen identities of frankincense purchased from market as opposed to collected straight from the tree.[3]
Incensole in Archaeology
Frankincense has been used for thousands of years in religious ceremonies and for medicinal purposes[1]. In fact, by tracing incensole's degraded products, historians have been able to use it to understand the historical use of incense in religion. In one such case, the examination of incensole as a biomarker led to the confirmation of certain porous pots buried in Medieval, Belgian, Christian graves as incense burners. Further study indicated that though frankincense was a main component of funerary incense at the time, other, cheaper local resins were mixed into the incense, possibly to reduce cost[14].
Additionally, frankincense has been used for thousands of years as a medicine. It is listed in texts such as the Papyrus Ebers and the Syriac book of medicine and was prescribed by the practitioners Celsus and Culpepper as a remedy for a variety of ailments from stomach ulcers and gastrointestinal hemorrhages to gout and open wounds[13]. Modern analysis on the medical efficacy of frankincense has elucidated Incensole and Incensole Acetate along with Boswellic Acids as being the main active ingredients in frankincense[1].
Due to its religious and medicinal significance, frankincense and its biomarker components, like Incensole, can be found all over the world in Europe, Asia, the Mediterranean, and the Middle East[1][13][17] as a result of global trade.
Medicinal Properties
Previously, the therapeutic properties of frankincense had been attributed to Boswellic acids within the resin, but research from 2019 and 2020 has found Incensole and its acetate ether to be major contributors to frankincense's therapeutic efficacy[1]. This research has found Incensole to act as an anti-inflammatory and neuroprotective compound after murine head-trauma on top of exhibiting anxiolytic, anti-depressive, and sedative effects in mice[1].
It is proposed that Incensole works as an anti-inflammatory through the inhibition of the NF-κB pathway which is responsible for the increased production of proinflammatory proteins. Insensitivity in the NF-κB pathway is correlated to arthritis, asthma, inflammatory bowel disease, ataxia telangiectasia, cancers, and neurodegenerative diseases[1][12][18].
It has also been found that Incensole Acetate activates the TRPV3 channel[1] which, among other things, is responsible for regulating wound healing and the perception of pain and itching[19]. It has been thought that this is another key component of Incensole's role as an anti-inflammatory.
Incensole has also been cited as a potential antibacterial against Bacillus[12].
References
- ^ a b c d e f g h i Moussaieff, Arieh; Mechoulam, Raphael (2009-10). "Boswellia resin: from religious ceremonies to medical uses; a review of in-vitro, in-vivo and clinical trials". Journal of Pharmacy and Pharmacology. 61 (10): 1281–1293. doi:10.1211/jpp.61.10.0003. ISSN 0022-3573.
{{cite journal}}: Check date values in:|date=(help) - ^ a b c d e Corsano, S.; Nicoletti, R. (1967-01-01). "The structure of incensole". Tetrahedron. 23 (4): 1977–1984. doi:10.1016/S0040-4020(01)82601-6. ISSN 0040-4020.
- ^ a b c d e f g h i j Al-Harrasi, Ahmed; Csuk, Rene; Khan, Ajmal; Hussain, Javid (2019-05-01). "Distribution of the anti-inflammatory and anti-depressant compounds: Incensole and incensole acetate in genus Boswellia". Phytochemistry. 161: 28–40. doi:10.1016/j.phytochem.2019.01.007. ISSN 0031-9422.
- ^ a b Hamm, Sandrine; Bleton, Jean; Connan, Jacques; Tchapla, Alain (2005-06-01). "A chemical investigation by headspace SPME and GC–MS of volatile and semi-volatile terpenes in various olibanum samples". Phytochemistry. 66 (12): 1499–1514. doi:10.1016/j.phytochem.2005.04.025. ISSN 0031-9422.
- ^ a b c Strappaghetti, G.; Proietti, G.; Corsano, S.; Grgurina, I. (1982-03). "Synthesis of incensole". Bioorganic Chemistry. 11 (1): 1–3. doi:10.1016/0045-2068(82)90042-6.
{{cite journal}}: Check date values in:|date=(help) - ^ a b Majhi, Sasadhar (2020-10-29). "Diterpenoids: Natural Distribution, Semisynthesis at Room Temperature and Pharmacological Aspects‐A Decade Update". ChemistrySelect. 5 (40): 12450–12464. doi:10.1002/slct.202002836. ISSN 2365-6549.
- ^ author., Peters, Kenneth E. (Kenneth Eric), 1950-. The biomarker guide. ISBN 978-1-107-32604-0. OCLC 1030120220.
{{cite book}}:|last=has generic name (help)CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link) - ^ Zhou, Fei; Wang, Cheng-Yuan; Gutensohn, Michael; Jiang, Ling; Zhang, Peng; Zhang, Dabing; Dudareva, Natalia; Lu, Shan (2017-06-27). "A recruiting protein of geranylgeranyl diphosphate synthase controls metabolic flux toward chlorophyll biosynthesis in rice". Proceedings of the National Academy of Sciences. 114 (26): 6866–6871. doi:10.1073/pnas.1705689114. ISSN 0027-8424. PMC 5495272. PMID 28607067.
{{cite journal}}: CS1 maint: PMC format (link) - ^ a b "African Plant Database". africanplantdatabase.ch. Retrieved 2023-05-01.
- ^ R Michael Buch and Joseph A von Fraunhofer. “The Systemic and Brain Health Benefits of Frankincense”. EC Psychology and Psychiatry 9.5 (2020): 50-53.
- ^ "Extraction of Frankincense Resins - Bangor University". research.bangor.ac.uk. Retrieved 2023-05-01.
- ^ a b c Al-Yasiry, Ali Ridha Mustafa; Kiczorowska, Bożena (2016-01-04). "Frankincense – therapeutic properties". Postępy Higieny i Medycyny Doświadczalnej. 70: 380–391. doi:10.5604/17322693.1200553. ISSN 1732-2693.
- ^ a b c Michie, C A; Cooper, E (1991-10). "Frankincense and Myrrh as Remedies in Children". Journal of the Royal Society of Medicine. 84 (10): 602–605. doi:10.1177/014107689108401011. ISSN 0141-0768. PMC 1295557. PMID 1744842.
{{cite journal}}: Check date values in:|date=(help)CS1 maint: PMC format (link) - ^ a b Baeten, Jan; Deforce, Koen; Challe, Sophie; Vos, Dirk De; Degryse, Patrick (2014-11-12). "Holy Smoke in Medieval Funerary Rites: Chemical Fingerprints of Frankincense in Southern Belgian Incense Burners". PLOS ONE. 9 (11): e113142. doi:10.1371/journal.pone.0113142. ISSN 1932-6203. PMC 4229304. PMID 25391130.
{{cite journal}}: CS1 maint: PMC format (link) CS1 maint: unflagged free DOI (link) - ^ "NMR Guidelines for ACS Journals" (PDF). American Chemical Society. December 2013. Retrieved 23 May 2023.
{{cite web}}: CS1 maint: url-status (link) - ^ Al-Shidhani, Sulaiman; Rehman, Najeeb Ur; Mabood, Fazal; Al-Broumi, Muhammed; Hussain, Hidayat; Hussain, Javid; Csuk, Rene; Al-Harrasi, Ahmed (2018-05). "Quantification of Incensole in Three Boswellia Species by NIR Spectroscopy Coupled with PLSR and Cross-Validation by HPLC: Quantification of incensole in Boswellia species by NIRS and HPLC". Phytochemical Analysis. 29 (3): 300–307. doi:10.1002/pca.2743.
{{cite journal}}: Check date values in:|date=(help) - ^ Gebrehiwot, K.; Muys, B.; Haile, M.; Mitloehner, R. (2003-12). "Introducing Boswellia papyrifera (Del.) Hochst and its non-timber forest product, frankincense". International Forestry Review. 5 (4): 348–353. doi:10.1505/ifor.5.4.348.22661. ISSN 1465-5489.
{{cite journal}}: Check date values in:|date=(help) - ^ Moussaieff, Arieh; Shohami, Esther; Kashman, Yoel; Fride, Ester; Schmitz, M. Lienhard; Renner, Florian; Fiebich, Bernd L.; Munoz, Eduardo; Ben-Neriah, Yinon; Mechoulam, Raphael (2007-12-01). "Incensole Acetate, a Novel Anti-Inflammatory Compound Isolated from Boswellia Resin, Inhibits Nuclear Factor-κB Activation". Molecular Pharmacology. 72 (6): 1657–1664. doi:10.1124/mol.107.038810. ISSN 0026-895X. PMID 17895408.
- ^ Yang, Pu; Zhu, Michael X. (2014), Nilius, Bernd; Flockerzi, Veit (eds.), "TRPV3", Mammalian Transient Receptor Potential (TRP) Cation Channels: Volume I, Berlin, Heidelberg: Springer, pp. 273–291, doi:10.1007/978-3-642-54215-2_11#abs1, ISBN 978-3-642-54215-2, retrieved 2023-05-01
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