Visnagin

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.

Visnagin
Names
IUPAC name
4-Methoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one[1]
Other names
Visnacorin; Khella; Desmethoxykhellin; 5-Methoxy-2-methylfuranochromone; 5-Methoxy-2-methyl-6,7-furanochrome
Identifiers
3D model (JSmol)
5-19-06-00030
ChEBI
ChemSpider
ECHA InfoCard 100.001.301
EC Number
  • 201-430-3
234955
KEGG
RTECS number
  • LV1420000
UNII
Properties
C13H10O4
Molar mass 230.219 g·mol−1
Appearance Solid
Melting point 144 to 145 °C (291 to 293 °F; 417 to 418 K)
soluble
Solubility ethanol
Hazards
Main hazards Harmful by ingestion
Safety data sheet
GHS pictograms
GHS Signal word Warning
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Lethal dose or concentration (LD, LC):
832 mg/kg (oral, rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

History

Ammi visnaga, 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.[2]

Occurrences

Visnagin naturally occurs in Ammi visnaga, 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.[3]

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).[4] [4]

Oligomerization

Visnagin molecules can go over an oligomerization to form a chain of visnagin molecules.[5]

Visnagin olygomerization reaction

Animal study

Visnagin has biological activity in animal models as a vasodilator and reduces blood pressure by inhibiting calcium influx into the cell.[6] In rats, visnagin prevents the formation of kidney stones by prolonging the induction time of nucleation of crystals.[7][8]

On December 8, 2014 it was reported that "visnagin protects against doxorubicin-induced cardiomyopathy through modulation of mitochondrial malate dehydrogenase."[9]

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References
  1. Visnacorin, ChemSpider
  2. Haug, Karin G.; Weber, Benjamin; Hochhaus, Guenther; Butterweck, Veronika (2012). "Nonlinear pharmacokinetics of visnagin in rats after intravenous bolus administration". European Journal of Pharmaceutical Sciences. 45 (1–2): 79–89. doi:10.1016/j.ejps.2011.10.023. PMID 22085634.
  3. Badawi, M.M.; Fayez, M.B.E. (1965). "Natural chromones—I". Tetrahedron. 21 (10): 2925. doi:10.1016/S0040-4020(01)98378-4.
  4. Mustafa, Ahmed (2009-09-15). "The Chemistry of Heterocyclic Compounds, Furopyrans and Furopyrones". ISBN 9780470188354. Cite journal requires |journal= (help)
  5. Pradhan, Padmanava; Banerji, Asoke (1998). "Novel cyclobutane fused furochromone oligomers from the seeds of Pimpinella monoica Dalz". Tetrahedron. 54 (48): 14541. doi:10.1016/S0040-4020(98)00913-2.
  6. Lee, Jin-Koo; Jung, Jun-Sub; Park, Sang-Hee; Park, Soo-Hyun; Sim, Yun-Beom; Kim, Seon-Mi; Ha, Tal-Soo; Suh, Hong-Won (2010). "Anti-inflammatory effect of visnagin in lipopolysaccharide-stimulated BV-2 microglial cells". Archives of Pharmacal Research. 33 (11): 1843–50. doi:10.1007/s12272-010-1117-1. PMID 21116788.
  7. http://ull.chemistry.uakron.edu/erd/Chemicals/14000/12765.html
  8. Abdel-Aal, E.A.; Daosukho, S.; El-Shall, H. (2009). "Effect of supersaturation ratio and Khella extract on nucleation and morphology of kidney stones". Journal of Crystal Growth. 311 (9): 2673. doi:10.1016/j.jcrysgro.2009.02.027.
  9. 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. (10 December 2014). "Visnagin protects against doxorubicin-induced cardiomyopathy through modulation of mitochondrial malate dehydrogenase". Science Translational Medicine. 6 (266): 266ra170–266ra170. doi:10.1126/scitranslmed.3010189. PMC 4360984. PMID 25504881.
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