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Baicalin

From Wikipedia, the free encyclopedia

Not to be confused withbaicalein.
Baicalin
Names
IUPAC name
5,6-Dihydroxy-4-oxoflav-2-en-7-yl β-D-glucopyranosiduronic acid
Systematic IUPAC name
(2S,3S,4S,5R,6S)-6-[(5,6-Dihydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Other names
Baicalein 7-O-glucuronide; 5,6-Dihydroxy-4-oxygen-2-phenyl-4H-1-benzopyran-7-β-D-glucopyranose acid
Identifiers
3D model (JSmol)
70480
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.133.557Edit this at Wikidata
EC Number
  • 606-866-1
KEGG
UNII
  • InChI=1S/C21H18O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21,23-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1 checkY
    Key: IKIIZLYTISPENI-ZFORQUDYSA-N checkY
  • InChI=1/C21H18O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21,23-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1
    Key: IKIIZLYTISPENI-ZFORQUDYBD
  • O=C3\C=C(/Oc2cc(O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)c(O)c(O)c23)c4ccccc4
Properties
C21H18O11
Molar mass446.364 g·mol−1
Melting point202 to 205 °C (396 to 401 °F; 475 to 478 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315,H319,H335
P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P362,P403+P233,P405,P501
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Baicalin is theglucuronide of thepolyphenolic compoundbaicalein.

Natural occurrences

[edit]

Baicalin is found in several species in the genusScutellaria, includingScutellaria baicalensis,[1] andScutellaria lateriflora. There are 10 mg/g baicalin inScutellaria galericulata leaves.[2] It is also present in thebark isolate of theOroxylum indicum tree.

Medical uses

[edit]

Baicalin is one of the chemical ingredients of at least two herbal supplements:Shuanghuanglian[1] andSho-Saiko-To, which is aChinese classic herbal formula, and listed in Japan asKampo medicine.[citation needed]

Baicalin, along with itsaglycone baicalein, is apositive allosteric modulator of thebenzodiazepine site and/or a non-benzodiazepine site of theGABAA receptor.[3][4][5] In mice, baicalin producesanxiolytic effects withoutsedative ormyorelaxant effects.[6][7] It is thought that baicalin, along with other flavonoids, may underlie the anxiolytic effects ofS. baicalensis andS. lateriflora.[8][9]

Baicalin is a knownprolyl endopeptidase inhibitor.[10] It inducesapoptosis inpancreatic cancer cells.[11]

References

[edit]
  1. ^abSu Hx, Yao S, Zhao WF, Li Mj, Liu J, Shang WJ, Xie H, Ke CQ, Hu HC, Gao Mn, Yu KQ, Liu H, Shen JS, Tang W, Zhang Lk, Xiao Gf, Ni L, Wang Dw, Zuo JP, Jiang HL, Bai F, Wu Y, Ye Y, Xu YC (2020)."Anti-SARS-CoV-2 activities in vitro of Shuanghuanglian preparations and bioactive ingredients".Acta Pharmacologica Sinica.41 (9):1167–1177.doi:10.1038/s41401-020-0483-6.PMC 7393338.PMID 32737471.
  2. ^P.H. and Horhammer, L., Hager's Handbuch der Pharmazeutischen Praxis, Vols. 2-6, Springer-Verlag, Berlin, 1969-1979
  3. ^Wang H, Hui KM, Xu S, Chen Y, Wong JT, Xue H (2002). "Two flavones from Scutellaria baicalensis Georgi and their binding affinities to the benzodiazepine site of the GABAA receptor complex".Pharmazie.57 (12):857–8.PMID 12561253.
  4. ^Hui KM, Wang XH, Xue H (2000)."Interaction of flavones from the roots of Scutellaria baicalensis with the benzodiazepine site".Planta Med.66 (1):91–3.doi:10.1055/s-0029-1243121.PMID 10705749.S2CID 260249283.
  5. ^Edwin Lowell Cooper, Nobuo Yamaguchi (1 January 2004).Complementary and Alternative Approaches to Biomedicine. Springer Science & Business Media. pp. 188–.ISBN 978-0-306-48288-5.
  6. ^Xu Z, Wang F, Tsang SY, Ho KH, Zheng H, Yuen CT, Chow CY, Xue H (2006)."Anxiolytic-Like Effect of baicalin and its additivity with other anxiolytics".Planta Med.72 (2):189–92.doi:10.1055/s-2005-873193.PMID 16491459.S2CID 2398014.
  7. ^Liao JF, Hung WY, Chen CF (2003). "Anxiolytic-like effects of baicalein and baicalin in the Vogel conflict test in mice".Eur. J. Pharmacol.464 (2–3):141–6.doi:10.1016/s0014-2999(03)01422-5.PMID 12620506.
  8. ^Awad R, Arnason JT, Trudeau V, Bergeron C, Budzinski JW, Foster BC, Merali Z (2003). "Phytochemical and biological analysis of skullcap (Scutellaria lateriflora L.): a medicinal plant with anxiolytic properties".Phytomedicine.10 (8):640–9.doi:10.1078/0944-7113-00374.PMID 14692724.
  9. ^Stefanie Schwartz (9 January 2008).Psychoactive Herbs in Veterinary Behavior Medicine. John Wiley & Sons. pp. 139–.ISBN 978-0-470-34434-7.
  10. ^Tarragó T, Kichik N, Claasen B, Prades R, Teixidó M, Giralt E (2008). "Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor".Bioorganic & Medicinal Chemistry.16 (15):7516–24.doi:10.1016/j.bmc.2008.04.067.PMID 18650094.
  11. ^Takahashi H, Chen MC, Pham H, Angst E, King JC, Park J, Brovman EY, Ishiguro H, Harris DM, Reber HA, Hines OJ, Gukovskaya AS, Go VL, Eibl G (2011)."Baicalein, a component of Scutellaria baicalensis, induces apoptosis by Mcl-1 down-regulation in human pancreatic cancer cells".Biochim Biophys Acta.1813 (8):1465–1474.doi:10.1016/j.bbamcr.2011.05.003.PMC 3123440.PMID 21596068.
Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
O-methylated flavones
Glycosides
of apigenin
of baicalein
of hypolaetin
of luteolin
Acetylated
Sulfated glycosides
Polymers
Drugs
Alcohols
Barbiturates
Benzodiazepines
Carbamates
Flavonoids
Imidazoles
Kava constituents
Monoureides
Neuroactive steroids
Nonbenzodiazepines
Phenols
Piperidinediones
Pyrazolopyridines
Quinazolinones
Volatiles/gases
Others/unsorted
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