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Template:Peganum harmala alkaloids: Difference between revisions

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>David Hedlund
ttps://www.cdfa.ca.gov/plant/ipc/encycloweedia/weedinfo/peganum.htm
>David Hedlund
Added 42 beta-carbolines
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{| class="wikitable sortable" style="text-align: center"
{| class="wikitable sortable" style="text-align: center"
|-
|-
! Alkaloid
! Beta-carboline<ref>{{cite journal |title=Table 4 {{!}} Peganum spp.: A Comprehensive Review on Bioactivities and Health-Enhancing Effects and Their Potential for the Formulation of Functional Foods and Pharmaceutical Drugs |journal=www.hindawi.com |url=https://www.hindawi.com/journals/omcl/2021/5900422/tab4/}}</ref>
! Content
! Content
! Type
|-
|-
! [[Desoxypeganine]]<ref>https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3841998/</ref>
! 1-hydroxy-7-methoxy-β-carboline
|  
|  
| MAO-A<ref>{{cite journal |last1=Algorta |first1=J |last2=Pena |first2=MA |last3=Maraschiello |first3=C |last4=Alvarez-González |first4=A |last5=Maruhn |first5=D |last6=Windisch |first6=M |last7=Mucke |first7=HA |title=Phase I clinical trial with desoxypeganine, a new cholinesterase and selective MAO-A inhibitor: tolerance and pharmacokinetics study of escalating single oral doses. |journal=Methods and findings in experimental and clinical pharmacology |date=March 2008 |volume=30 |issue=2 |pages=141-7 |doi=10.1358/mf.2008.30.2.1159649 |pmid=18560630}}</ref>
|-
|-
! [[Harmalicidine]]<ref>{{cite journal |last1=Lamchouri |first1=F |last2=Zemzami |first2=M |last3=Jossang |first3=A |last4=Abdellatif |first4=A |last5=Israili |first5=ZH |last6=Lyoussi |first6=B |title=Cytotoxicity of alkaloids isolated from Peganum harmala seeds. |journal=Pakistan journal of pharmaceutical sciences |date=July 2013 |volume=26 |issue=4 |pages=699-706 |pmid=23811445}}</ref>
! 2-aldehyde-tetrahydroharmine
|  
|  
|-
! 3-hydroxylated harmine
|
|-
! 6-methoxytetrahydro-1-norharmanone
|
|-
! 8-hydroxy-harmine
|
|-
! Acetylnorharmine
|
|-
! Dihydroruine
|
|-
! Dipegene
|
|-
! Harmalacidine (HMC)
|
|-
! Harmalacinine
|
|-
! Harmalanine
|  
|  
|-
|-
! [[Harmaline]] (harmidine)
! Harmalicine
|
|-
! Harmalidine
|
|-
! [[Harmaline]] (dihydroharmine, DHH, harmidine)
| 0.25%<ref name=partial/>–0.79%<ref name=chroma/>–5.6%<ref name=new1/>
| 0.25%<ref name=partial/>–0.79%<ref name=chroma/>–5.6%<ref name=new1/>
| [[Reversible inhibitor of monoamine oxidase A]] (RIMA)
|-
|-
! [[Harmalol]]
! Harmalol
| 0.6%<ref name=new1/>–3.90%<ref name=partial/>
| 0.6%<ref name=new1/>–3.90%<ref name=partial/>
|-
! Harmane (harman)
| 0.16%<ref name=partial>{{cite journal |vauthors=Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR |title=Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts |journal=Anal. Chim. Acta |volume=575 |issue=2 |pages=290–9 |date=August 2006 |pmid=17723604 |doi=10.1016/j.aca.2006.05.093}}</ref> | MAO-A and MAO B<ref>{{cite journal |last1=Herraiz |first1=T |last2=Chaparro |first2=C |title=Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee. |journal=Life sciences |date=18 January 2006 |volume=78 |issue=8 |pages=795-802 |doi=10.1016/j.lfs.2005.05.074 |pmid=16139309}}</ref>
|-
! Harmic acid
|  
|  
|-
|-
! [[Harmane]] (harman)
! Harmic acid methyl ester
| 0.16%<ref name=partial>{{cite journal |vauthors=Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR |title=Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts |journal=Anal. Chim. Acta |volume=575 |issue=2 |pages=290–9 |date=August 2006 |pmid=17723604 |doi=10.1016/j.aca.2006.05.093}}</ref>
|  
| MAO-A and MAO B<ref>{{cite journal |last1=Herraiz |first1=T |last2=Chaparro |first2=C |title=Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee. |journal=Life sciences |date=18 January 2006 |volume=78 |issue=8 |pages=795-802 |doi=10.1016/j.lfs.2005.05.074 |pmid=16139309}}</ref>
|-
|-
! [[Harmine]] (banisterine, telepathine)
! [[Harmine]] (banisterine, telepathinec, yageine)
| 0.44%<ref name=chroma>{{cite journal |vauthors=Pulpati H, Biradar YS, Rajani M |title=High-performance thin-layer chromatography densitometric method for the quantification of harmine, harmaline, vasicine, and vasicinone in Peganum harmala |journal=J AOAC Int |volume=91 |issue=5 |pages=1179–85 |year=2008 |doi=10.1093/jaoac/91.5.1179 |pmid=18980138|doi-access=free }}</ref>–1.84%<ref name=partial/>–4.3%<ref name=new1>{{cite journal |vauthors=Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H |title=beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO) |journal=Food Chem. Toxicol. |volume=48 |issue=3 |pages=839–45 |date=March 2010 |pmid=20036304 |doi=10.1016/j.fct.2009.12.019}}</ref> – The coatings of the seeds are said to contain large amounts of harmine.<ref name=cdfa>{{cite web|url= https://www.cdfa.ca.gov/plant/ipc/encycloweedia/weedinfo/peganum.htm |title=''African rue or Harmel'' |access-date=17 February 2021 |publisher=cdfa.ca.gov |archive-url=https://web.archive.org/web/20151022101427/https://www.cdfa.ca.gov/plant/ipc/encycloweedia/weedinfo/peganum.htm |archive-date=22 October 2015 }}</ref>
| 0.44%<ref name=chroma>{{cite journal |vauthors=Pulpati H, Biradar YS, Rajani M |title=High-performance thin-layer chromatography densitometric method for the quantification of harmine, harmaline, vasicine, and vasicinone in Peganum harmala |journal=J AOAC Int |volume=91 |issue=5 |pages=1179–85 |year=2008 |doi=10.1093/jaoac/91.5.1179 |pmid=18980138|doi-access=free }}</ref>–1.84%<ref name=partial/>–4.3%<ref name=new1>{{cite journal |vauthors=Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H |title=beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO) |journal=Food Chem. Toxicol. |volume=48 |issue=3 |pages=839–45 |date=March 2010 |pmid=20036304 |doi=10.1016/j.fct.2009.12.019}}</ref> – The coatings of the seeds are said to contain large amounts of harmine.<ref name=cdfa>{{cite web|url= https://www.cdfa.ca.gov/plant/ipc/encycloweedia/weedinfo/peganum.htm |title=''African rue or Harmel'' |access-date=17 February 2021 |publisher=cdfa.ca.gov |archive-url=https://web.archive.org/web/20151022101427/https://www.cdfa.ca.gov/plant/ipc/encycloweedia/weedinfo/peganum.htm |archive-date=22 October 2015 }}</ref>
| [[Reversible inhibitor of monoamine oxidase A]] (RIMA)
|-
|-
! [[Tetrahydroharmine]] (THH)
! Harmine N-oxide
|
|-
! Harmol
|
|-
! Isoharmine
|
|-
! Isopeganine
|
|-
! Norharman
|
|-
! Norharmine (tetrahydro-beta-carboline)
|
|-
! Pegaharmine A
|
|-
! Pegaharmine B
|
|-
! Pegaharmine C
|
|-
! Pegaharmine D
|
|-
! Pegaharmine E
|
|-
! Pegaharmine F
|
|-
! Pegaharmine G
|
|-
! Pegaharmine H
|
|-
! Pegaharmine I
|
|-
! Pegaharmine J
|
|-
! Pegaharmine K
|
|-
! Peganine A
|
|-
! Peganine B
|
|-
! Peganumal A
|
|-
! Peganumal A
|
|-
! Peganumal B
|
|-
! Peganumal B
|
|-
! Peganumine A
|
|-
! Peganumine B
|
|-
! Ruine
|
|-
! Tetrahydroharman
|
|-
! [[Tetrahydroharmine]] (THH, leptaflorine)
| 0.1%<ref name=new1/>
| 0.1%<ref name=new1/>
| [[Serotonine reuptake inhibitor]]<ref name="pmid10404423">{{cite journal |last=Callaway |first=James C. |last2=McKenna |first2=Dennis |author-link2=Dennis McKenna |last3=Grob |first3=Charles S. |title=Pharmacokinetics of hoasca alkaloids in healthy humans |journal=[[Journal of Ethnopharmacology]] |volume=65 |issue=3 |pages=243–56 |date=June 1999 |pmid=10404423 |issn=0279-1072 |doi=10.1016/S0378-8741(98)00168-8|display-authors=etal}}</ref>
|-
|-
! [[Vasicine]] (peganine)<ref name=nook/>
! Tetrahydroharmol
| 0.25%<ref name=chroma/>
|  
|  
|-
|-
! [[Vasicinone]]<ref name=nook/>
! Tetrahydronorharman
| 0.0007%<ref name=chroma/>
|  
|  
|}
|}

Revision as of 04:41, 20 July 2021

Beta-carboline[1] Content
1-hydroxy-7-methoxy-β-carboline
2-aldehyde-tetrahydroharmine
3-hydroxylated harmine
6-methoxytetrahydro-1-norharmanone
8-hydroxy-harmine
Acetylnorharmine
Dihydroruine
Dipegene
Harmalacidine (HMC)
Harmalacinine
Harmalanine
Harmalicine
Harmalidine
Harmaline (dihydroharmine, DHH, harmidine) 0.25%[2]–0.79%[3]–5.6%[4]
Harmalol 0.6%[4]–3.90%[2]
Harmane (harman) MAO-A and MAO B[5]
Harmic acid
Harmic acid methyl ester
Harmine (banisterine, telepathinec, yageine) 0.44%[3]–1.84%[2]–4.3%[4] – The coatings of the seeds are said to contain large amounts of harmine.[6]
Harmine N-oxide
Harmol
Isoharmine
Isopeganine
Norharman
Norharmine (tetrahydro-beta-carboline)
Pegaharmine A
Pegaharmine B
Pegaharmine C
Pegaharmine D
Pegaharmine E
Pegaharmine F
Pegaharmine G
Pegaharmine H
Pegaharmine I
Pegaharmine J
Pegaharmine K
Peganine A
Peganine B
Peganumal A
Peganumal A
Peganumal B
Peganumal B
Peganumine A
Peganumine B
Ruine
Tetrahydroharman
Tetrahydroharmine (THH, leptaflorine) 0.1%[4]
Tetrahydroharmol
Tetrahydronorharman
  1. ↑ "Table 4 | Peganum spp.: A Comprehensive Review on Bioactivities and Health-Enhancing Effects and Their Potential for the Formulation of Functional Foods and Pharmaceutical Drugs". www.hindawi.com. 
  2. ↑ 2.0 2.1 2.2 2.3 Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR (August 2006). "Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts". Anal. Chim. Acta. 575 (2): 290–9. doi:10.1016/j.aca.2006.05.093. PMID 17723604. 
  3. ↑ 3.0 3.1 Pulpati H, Biradar YS, Rajani M (2008). "High-performance thin-layer chromatography densitometric method for the quantification of harmine, harmaline, vasicine, and vasicinone in Peganum harmala". J AOAC Int. 91 (5): 1179–85. doi:10.1093/jaoac/91.5.1179 Freely accessible. PMID 18980138. 
  4. ↑ 4.0 4.1 4.2 4.3 Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H (March 2010). "beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO)". Food Chem. Toxicol. 48 (3): 839–45. doi:10.1016/j.fct.2009.12.019. PMID 20036304. 
  5. ↑ Herraiz, T; Chaparro, C (18 January 2006). "Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee". Life sciences. 78 (8): 795–802. doi:10.1016/j.lfs.2005.05.074. PMID 16139309. 
  6. ↑ "African rue or Harmel". cdfa.ca.gov. Archived from the original on 22 October 2015. Retrieved 17 February 2021. 
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