Visnagin Explained

Visnagin is an organic chemical compound with the molecular formula C13H10O4 It is a furanochromone, a compound derivative of chromone (1,4-benzopyrone) and furan.

History

Visnaga daucoides, the main source for visnagin, has been used in traditional medicine in the Middle East to ease urinary tract pain associated with kidney stones and to promote stone passage.[1]

Occurrences

Visnagin naturally occurs in Visnaga daucoides, a species of flowering plant in the carrot family known by many common names, including bisnaga, toothpickweed, and khella. Visnagin-containing khella seeds are usually found mainly in Middle East countries such as Egypt and Turkey and also in Northern African countries such as Morocco. Visnagin can be extracted directly from khella seeds.

Synthesis

Modified synthesis of the naturally occurring visnagin is reported. Starting from phloroghrcin aldehyde, and building on the 2-methyl-y-pyrone, 2-methyl-5,7-dihydroxy-dfo-yl-chromone was obtained. Construction of the furan moiety was realized by a conventional method through the 7-carboxymethoxy ether giving S-norvisnagin which can be methylated to visnagin.[2]

Reactions

Condensation

Visnagin analogs can be synthesized through the condensation of visnagone with esters and sodium. This leads to the product of 2-ethyl, 2-(3'-pyridyl) visnagin analog (50c).[3]

Oligomerization

Visnagin molecules can go over an oligomerization to form a chain of visnagin molecules.[4]

Animal study

Visnagin has biological activity in animal models as a vasodilator and reduces blood pressure by inhibiting calcium influx into the cell.[5] In rats, visnagin prevents the formation of kidney stones by prolonging the induction time of nucleation of crystals.[6] On December 8, 2014, it was reported that "visnagin protects against doxorubicin-induced cardiomyopathy through modulation of mitochondrial malate dehydrogenase."[7] In another scientific study, it was reported that visnagin treatment reduced ischemia-reperfusion associated testicular injury in urological interventions. [8]

Notes and References

  1. 10.1016/j.ejps.2011.10.023 . Nonlinear pharmacokinetics of visnagin in rats after intravenous bolus administration . 2012 . Haug . Karin G. . Weber . Benjamin . Hochhaus . Guenther . Butterweck . Veronika . European Journal of Pharmaceutical Sciences . 45 . 79–89 . 22085634 . 1–2. Ammi visnaga L. (syn. Khella, Apiaceae) fruit preparations, such as tea prepared from crushed or powdered seeds, have traditionally been used in the Middle East to ease urinary tract pain associated with kidney stones and to promote stone passage (Gunaydin and Beyazit, 2004)..
  2. 10.1016/S0040-4020(01)98378-4 . Natural chromones—I . 1965 . Badawi . M.M. . Fayez . M.B.E. . Tetrahedron . 21 . 10 . 2925.
  3. Book: The Chemistry of Heterocyclic Compounds, Furopyrans and Furopyrones . 9780470188354 . Mustafa . Ahmed . 2009-09-15. John Wiley & Sons .
  4. 10.1016/S0040-4020(98)00913-2 . Novel cyclobutane fused furochromone oligomers from the seeds of Pimpinella monoica Dalz . 1998 . Pradhan . Padmanava . Banerji . Asoke . Tetrahedron . 54 . 48 . 14541.
  5. 10.1007/s12272-010-1117-1 . Anti-inflammatory effect of visnagin in lipopolysaccharide-stimulated BV-2 microglial cells . 2010 . Lee . Jin-Koo . Jung . Jun-Sub . Park . Sang-Hee . Park . Soo-Hyun . Sim . Yun-Beom . Kim . Seon-Mi . Ha . Tal-Soo . Suh . Hong-Won . Archives of Pharmacal Research . 33 . 11 . 1843–50 . 21116788. 22168754 .
  6. 10.1016/j.jcrysgro.2009.02.027 . Effect of supersaturation ratio and Khella extract on nucleation and morphology of kidney stones . 2009 . Abdel-Aal . E.A. . Daosukho . S. . El-Shall . H. . Journal of Crystal Growth . 311 . 9 . 2673. 2009JCrGr.311.2673A .
  7. Liu. Y.. Asnani. A.. Zou. L.. Bentley. V. L.. Yu. M.. Wang. Y.. Dellaire. G.. Sarkar. K. S.. Dai. M.. Chen. H. H.. Sosnovik. D. E.. Shin. J. T.. Haber. D. A.. Berman. J. N.. Chao. W.. Peterson. R. T.. Visnagin protects against doxorubicin-induced cardiomyopathy through modulation of mitochondrial malate dehydrogenase. Science Translational Medicine. 10 December 2014. 6. 266. 266ra170. 10.1126/scitranslmed.3010189. 25504881. 4360984.
  8. Sağır, S., Şeker, U., Pekince Özener, M., Yüksel, M., & Demir, M. (2023). "Oxidative stress, apoptosis, inflammation, and proliferation modulator function of visnagin provide gonadoprotective activity in testicular ischemia-reperfusion injury". European Review for Medical and Pharmacological Sciences. 27 (20): 9968-9977| doi:10.26355/eurrev_202310_34176

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