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Sanguinarine

Sohrab A.E Hakim1, D Phil2
1 From the National Institute for Medical Research, Mill Hill, London, United Kingdom
2 The Sofa Hakim Medical Research Centre, 249 Dr. D. Naoroji Road, Bombay, India

Hakim SA, Phil D. Sanguinarine & hypothalamic glaucoma. Indian J Ophthalmol 1962;10:83-102


http://www.ijo.in/article.asp

http://www.ijo.in/text.asp?1962/10/4/83/39555

Sanguinarine is a benzphenanthridine alkaloid belonging to the iso-quinoline group. Over 114 iso-quinoline alkaloids are known and some of them like morphine, codeine and papaverine are amongst the most active and useful of drugs.  

Iso-quinoline alkaloids are usually found in plants belonging to two large botanical families, the poppies and fumarias, but they also occur sporadically in twelve other plant families (Manske, 1954). 

Sanguinarine was hitherto regarded as a rare and obscure alkaloid first isolated 133 years ago from Sanguinaria canadensis L., the 'blood-root' used by the North American Indians to paint themselves scarlet. During the last one and a half centuries, the "epoch of alkaloid detection", chemists found sanguinarine in only eight other poppy-fumaria plants. Working at the National Institute for Medical Research, London, under the guid­ance of Sir Robert Robinson and Dr. James Walker, we found that sanguinarine was present and abundant in most morphological parts of nearly fifty species of poppy-fumaria weeds we examined.

Sanguinarine was more or less invariably present in the leaves and stems, often in the roots, capsules and seeds, and was the commonest fluorescent alkaloid seen in these species. It seems to have been missed for so many years because of its unusual solubility and absence of adequate tests. The details of our methods of extraction, detection, identification and results have been published elsewhere. (Hakim et al., 1961a).

An example of how sanguinarine had hitherto escaped chemical detection is found in the 'opium' poppy Papaver somniferum L. No plant has been more thoroughly investigated in the annals of chemistry, and yet sanguinarine was missed in this plant. We found it in its roots, stems and leaves. The young plants are used as edible herbs in the middle East and like the 'fumitory' herb, deliberately fed to cattle.

Those of you who have seen the cornfields of Europe and North India will recollect the myriads of scarlet poppies (Papaver rhoeas L., P. hybridum L., and P. dubium L.) growing amongst the grain. Everyone of these poppies contain sanguinarine in either its roots, stems, leaves or seeds. 

The National Formulary (1960), the Dispensatory of the United States of America (1960) and the British Pharmaceutical Codex (1949) sponsor the use of Sanguinaria canadensis L., the 'blood-root' over­flowing with the scarlet alkaloid sanguinarine !

It became evident that sanguinarine was not a rare and obscure alkaloid, but a glaucoma­genetic toxin definitely found and abundant in most parts of at least sixty-two poppy-fumaria species. Since the alkaloid was present in so many species distributed in 14 representative genera, it seems very likely that it will be found in most or all of the nearly seven hundred species of this vast plant family. If you visualise rice fields in spring, teeming with thousands of yellow argemone, or vegetable gardens scattered with the purple fumaria in early winter, or fields of wheat amongst which thousands of scarlet poppies fill an autumn landscape, you will realise how densely just three out of these hundreds of species can grow and, therefore, what an abundant source of sanguinarine is available in the plant kingdom.



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Sanguinarine

Adapted from Wikipedia, the free encyclopedia


Sanguinarine
Systematic (IUPAC) name
13-Methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo
[4,5-i]phenanthridinium
Identifiers
CAS number 2447-54-3
PubChem CID 5154
ChemSpider 4970
Chemical data
Formula C20H14NO4 
Mol. mass 332.09


Sanguinarine is a quaternary ammonium salt from the group of benzylisoquinoline alkaloids. 

It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy (Argemone mexicana), Chelodine (Chelidonium majus), and Plume poppy (Macleaya cordata). It is also found in the root, stem and leaves of the opium poppy but not in the capsule.

Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Epidemic dropsy is a disease that results from ingesting (too much) sanguinarine.

If applied to the skin, sanguinarine kills cells and can destroy (diseased) tissue. In turn, the bleeding wound may produce a scab, called an Eschar. For this reason, sanguinarine is termed an escharotic.

In plants, sanguinarine is synthesized from dihydrosanguinarine through the action of Dihydrobenzophenanthridine oxidase (EC 1.5.3.12).[4]

* Berberine; a plant based compound with similar chemical classification as sanguinarine

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[edit] Notes

1. ^ Alfredo C. Santos, Pacifica Adkilen (July 1932). "The Alkaloids of Argemon Mexicana". Journal of the American Chemical Society 54, No. 7: 2923–2924. 
2. ^ Inhibition of Na+-K+-ATPase activity and ouabain binding by sanguinarine Barry J. R. Pitts, Laurence R. Meyerson, Ph. D, Drug Development Research, Volume 1, Issue 1.
3. ^ Das M, Khanna SK (May 1997). "Clinicoepidemiological, toxicological, and safety evaluation studies on argemone oil". Critical reviews in toxicology 27 (3): 273–97. doi:10.3109/10408449709089896. PMID 9189656. 
4. ^ Chelirubine, Macarpine, and Sanguinarine Biosynthesis International Union of Biochemistry and Molecular Biology, Recommendations on Biochemical & Organic Nomenclature, Symbols & Terminology etc., web interface

[edit] Additional references

* D. Walterova, J. Ulrichova, I. Valka, J. Vicar, C. Vavreckova, E. Taborska, R.J. Harjrader, D.L. Meyer, H. Cerna and V. Simanek(1996) Benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine: biological activities and dental care applications, Acta Univ. Palacky Olomouc Fac. Med. 139 (1995), pp. 7–16.
* Zdarilova et al., A. Zdarilova, J. Malikova, Z. Dvorak, J. Ulrichova and V. Simanek,2006, Quaternary isoquinoline alkaloids sanguinarine and chelerythrine. In vitro and in vivo effects, Chemicke Listy 100 (2006), pp. 30–41.
* Das M. and Khanna S.K.(1997) Clinicoepidemiological, toxicological, and safety evaluation studies on argemone oil, Crit. Rev. Toxicol. 27 pp. 273–297.
* Mukul Das, Kishore Babu, Naveen P. Reddy and Lalit M. Srivastava.(2005) Oxidative damage of plasma proteins and lipids in epidemic dropsy patients: Alterations in antioxidant status. Biochimica et Biophysica Acta- General Subjects, Vol 1722, Issue 2, Pg 209-217
* A. Zdařilová, R. Vrzal, M. Rypka, J. Ulrichová and Z. Dvořák(2006)Investigation of sanguinarine and chelerythrine effects on CYP1A1 expression and activity in human hepatoma cells Food and Chemical Toxicology, Vol 44(2) , Pg 242-249
* Manu Lopus and Dulal Panda (2006) The benzophenanthridine alkaloid sanguinarine perturbs microtubule assembly dynamics through tubulin binding. A possible mechanism for its antiproliferative activity. FEBS J. Vol 273, Issue 10, Pg 2139-2150.
* Differential Antiproliferative and Apoptotic Response of Sanguinarine for Cancer Cells versus Normal Cells Nihal Ahmad, Sanjay Gupta, Mirza M. Husain, Kaisa M. Heiskanen and Hasan Mukhtar, Clinical Cancer Research Vol. 6 (April 2000), pp. 1524-1528.

References Top

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9. Duke-Elder, S. (1940) Text-Book of Ophthalmology, 3, 3280-3429, Henry Kimpton, London. Back to cited text no. 9 
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11. Duke-Elder, S. (1952) The Phasic Variations in the Ocular Tension in Primary Glaucoma. Am. J. Ophthal. 35. 1. Back to cited text no. 11 
12. Duke-Elder, S, (1957) The Boman Lecture-The Aetiology of Simple Glau­coma, Trans. Ophthal. Soc. 1'. K. 77, 205. Back to cited text no. 12 
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21. Hakim, S. (1953) D, Phil. Thesis, University- of Oxford. Back to cited text no. 21 
22. Hakim, S. (1954) Argemone Oil, San­guinarine, & Epidemic-Dropsy Glaucoma. Brit. J. Ophthal. 38, 193. Back to cited text no. 22 
23. Hakim, S. (1957a) Extraction & Detec­tion of Poppy Alkaloids. J. Physiol. 138, 8 P. Back to cited text no. 23 
24. Hakim, S. (1057b) Poppy Alkaloids & Glaucoma. J. Physiol. 138, 40 P. Back to cited text no. 24 
25. Hakim, S. Mijovic, V. & Walker, J. (1961a) Poppy Alkaloids & Glaucoma Nature, 189, 198, Back to cited text no. 25 
26. Hakim, S. Mijovic, V. & ``Walker, J. (1961b) Transmission of Sanguinarine &, a Metabolic Product in Milk. Nature, 189, 201. Back to cited text no. 26 
27. Hamburger, (1924) bled. kl, 20, 274. Back to cited text no. 27 
28. Hamburger, (1925) D. med, W. 51, 186, Back to cited text no. 28 
29. Hartmann, E. (1952) Annales d'Oculisti­que. 185, 438. Back to cited text no. 29 
30. Hutchinson, J. (1921) Kew Bull. No. 3. P. 97. Back to cited text no. 30 
31. Indraji, T. J. (1910) Vanaspati Shastre (Gujerati) P. 23-27. Bombay. Back to cited text no. 31 
32. Jadavji, A. (1950) Dravya-Guna-Gnyan (Hindi) p. 86-87. Nirnaya Sagar, Bombay. Back to cited text no. 32 
33. Kanda, K, & So, K. (1933) Brit. J. Ophthal. 17, 354. Back to cited text no. 33 
34. Kirwan, E. (1936) Brit. J. Ophthal. 20, 321. Back to cited text no. 34 
35. Lacassagne. A. et. al., (1956) Advances in Cancer Research 4, 315. Back to cited text no. 35 
36. Lagrange, F. (1922) Du Glocome et de l'Hypotonie, Paris. Back to cited text no. 36 
37. Langham, M. &. Lee, P. (1957) Brit. J. Ophthal. 41, 65. Back to cited text no. 37 
38. Leib, W. & Scherf, H. (1956) Klin. Mbl. Augenheilk. 128, 686. Back to cited text no. 38 
39. Luco, J. & Lissak, K, (1938) Amer. J. Physiol. 124, 271. Back to cited text no. 39 
40. Majitot, A. (1949) Bull. Socs. d'Ophtal. 27, 1193, Back to cited text no. 40 
41. Manske, R, (1954) The Alkaloids. vol. 4. Academic Press Inc., New York. Back to cited text no. 41 
42. Radovici, (1955) Ann. ocul., 188, 881. Back to cited text no. 42 
43. Robinson, R. (1948) J. R. Soc. Arts. 96, 806. (and personal guidance). Back to cited text no. 43 
44. Robinson, R. (1955) The Structural Relations of Natural Products p. 89. Clarendon Press, Oxford. Back to cited text no. 44 
45. von Sallmann, L. & Lowenstein, O. (1955) Amer. J. Ophthal. 39, (suppl) II. Back to cited text no. 45 
46. Shevalev, A. (1957) Bengal Glaucoma. (Russian). L. Dancheva, Odessa. Back to cited text no. 46 
47. Sorsbv, A. (1950) Incidence & Causes of Blindness. Brit. J. Ophthal. (sup). xiv. Back to cited text no. 47 
48. Thiel, R. (1926) Klin. Mbl. Augenheilk. 77, 753. Back to cited text no. 48 
49. Thief, R. (1955) Auge and Zwischenhirn. Bucheri des Augenarztes 23, 166. Beihfte der Klin. Mbl. Augenheilk. Back to cited text no. 49 
50. Vogt, M. (1957) Brit. med. Bull. 13, 166 Back to cited text no. 50 
51. Glaucoma, A. Symposium on. Ed. Duke-Elder, S. (1955), 2nd ed. (1957) Black well, Oxford. Back to cited text no. 51 
52. Glaucoma, Trans. 1st Conference on. Ed. Newell, F. (1956) J. Macy, New York. Back to cited text no. 52 
53. Glaucoma, Symposium on. Ed. Clark, W. (1959) Mosby, St. Louis. Back to cited text no. 53 
54. Report. National Society for the Prevention of Blindness U.S.A. (1950). Back to cited text no. 54


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A few of the 60+ natural medicines we manufacture at BSI....

Traditional Bloodroot Salve
Compound A
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Compound B
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Compound BVC
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Compound C
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Compound G
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