Peganum harmala
| Peganum harmala | |
|---|---|
 P. harmala in the nature. |
|
| Taxonomical nomenclature | |
| Kingdom | Plantae |
| Unranked | Angiosperms |
| Unranked | Eudicots |
| Unranked | Rosids |
| Order | Sapindales |
| Family | Nitrariaceae |
| Genus | Peganum |
| Species | P. harmala |
| Common nomenclature | |
| Common names | Espand, Esfand, Syrian rue |
| Constituents | |
| Active constituents | Harmala alkaloid |
Peganum harmala, commonly called Syrian rue, harmel, espand, esfand, wild rue, African rue, or aspand, is a plant native to the eastern Iranian region west to India. It has also spread invasively throughout Arizona, California, Montana, Nevada, Oregon, Texas and Washington.[1] The plant itself produces seeds which contain harmala alkaloids and is easily accessible and legal to purchase online.
Chemistry
Powdered syrian rue seeds act as a RIMA at doses of 2-5g. Syrian rue seeds contain several different harmala alkaloids at slightly varying percentages. Only some are monoamine oxidase A inhibitors. In one study, total harmala alkaloids were at least 5.9% of dried weight.[2][3][4] Seed extracts were potent reversible and competitive inhibitors of MAO-A but poor inhibitors of MAO-B.[5]
Total harmala alkaloids were at least 5.9% of dried weight, in one study.[4]
| Beta-carboline[6] | Content |
|---|---|
| 1-hydroxy-7-methoxy-β-carboline | |
| 2-aldehyde-tetrahydroharmine | |
| 3-hydroxylated harmine | |
| 6-methoxytetrahydro-1-norharmanone | |
| 8-hydroxy-harmine | |
| Acetylnorharmine | |
| Desoxypeganine[7] | |
| Dihydroruine | |
| Dipegene | |
| Harmalacidine (HMC) | |
| Harmalacinine | |
| Harmalanine | |
| Harmalicine | |
| Harmalidine | |
| Harmaline (dihydroharmine, DHH, harmidine) | 0.25%[4]–0.79%[8]–5.6%[5] |
| Harmalol | 0.6%[5]–3.90%[4] |
| Harmane (harman) | 0.16%[4] |
| Harmic acid | |
| Harmic acid methyl ester | |
| Harmine (banisterine, telepathinec, yageine) | 0.44%[8]–1.84%[4]–4.3%[5] – The coatings of the seeds are said to contain large amounts of harmine.[9] |
| 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 B | |
| Peganumine A | |
| Peganumine B | |
| Ruine | |
| Tetrahydroharman | |
| Tetrahydroharmine (THH, leptaflorine) | 0.1%[5] |
| Tetrahydroharmol | |
| Tetrahydronorharman |
Toxicity and harm potential
Dangerous interactions
See the MAOI page for substances that may cause dangerous interaction.
Cholinergics
Cholinergic substances combined with Peganum harmala can cause a cholinergic crisis because the plant contains several acetylcholinesterase inhibitors (AChEIs):
Drug use in pregnancy
Peganum harmala can induce miscarriage. It has traditionally been used as an abortifacient agent in Morocco, North Africa, and the Middle East.[13] It is believed that quinazoline alkaloids such as vasicine and vasicinone are responsible for the abortifacient activity of the plant.[14]
See also
External links
References
- ↑ USDA Plants Database
- ↑ Moloudizargari, M., Mikaili, P., Aghajanshakeri, S., Asghari, M., Shayegh, J. (2013). "Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids". Pharmacognosy Reviews. 7 (14): 199. doi:10.4103/0973-7847.120524. ISSN 0973-7847.
- ↑ Yuruktumen, A., Karaduman, S., Bengi, F., Fowler, J. (1 January 2008). "Syrian rue tea: A recipe for disaster". Clinical Toxicology. 46 (8): 749–752. doi:10.1080/15563650701323205. ISSN 1556-3650.
- ↑ 4.0 4.1 4.2 4.3 4.4 4.5 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.
- ↑ 5.0 5.1 5.2 5.3 5.4 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.
- ↑ "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.
- ↑ Algorta, J; Pena, MA; Maraschiello, C; Alvarez-González, A; Maruhn, D; Windisch, M; Mucke, HA (March 2008). "Phase I clinical trial with desoxypeganine, a new cholinesterase and selective MAO-A inhibitor: tolerance and pharmacokinetics study of escalating single oral doses". Methods and findings in experimental and clinical pharmacology. 30 (2): 141–7. doi:10.1358/mf.2008.30.2.1159649. PMID 18560630.
- ↑ 8.0 8.1 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
. PMID 18980138.
- ↑ "African rue or Harmel". cdfa.ca.gov. Archived from the original on 22 October 2015. Retrieved 17 February 2021.
- ↑ Kubo, M., Esumi, T., Imagawa, H., Fukuyama, Y. (2014). "Studies in Natural Products Chemistry". Chemical Diversity of Vibsane-Type Diterpenoids and Neurotrophic Activity and Synthesis of Neovibsanin. 43. Elsevier. pp. 41–78. doi:10.1016/B978-0-444-63430-6.00002-3. ISBN 9780444634306.
- ↑ 11.0 11.1 11.2 Zheng, X., Zhang, Z., Chou, G., Wu, T., Cheng, X., Wang, C., Wang, Z. (September 2009). "Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of Peganum nigellastrum Bunge by an in vitro TLC- bioautographic assay". Archives of Pharmacal Research. 32 (9): 1245–1251. doi:10.1007/s12272-009-1910-x. ISSN 0253-6269.
- ↑ Liu, W., Shi, X., Yang, Y., Cheng, X., Liu, Q., Han, H., Yang, B., He, C., Wang, Y., Jiang, B., Wang, Z., Wang, C. (7 April 2015). "In Vitro and In Vivo Metabolism and Inhibitory Activities of Vasicine, a Potent Acetylcholinesterase and Butyrylcholinesterase Inhibitor". PLOS ONE. 10 (4): e0122366. doi:10.1371/journal.pone.0122366. ISSN 1932-6203.
- ↑ Berdai, M. A., Labib, S., Harandou, M. (14 May 2014). "Peganum harmala L. Intoxication in a Pregnant Woman". Case Reports in Emergency Medicine. 2014: e783236. doi:10.1155/2014/783236. ISSN 2090-648X.
- ↑ Zygophyllaceae - an overview, ScienceDirect Topics