Baicalin

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title: "Baicalin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["anxiolytics", "flavone-glycosides", "flavonoid-glucuronides", "gabaa-receptor-positive-allosteric-modulators"] topic_path: "general/anxiolytics" source: "https://en.wikipedia.org/wiki/Baicalin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 459514199 | ImageFile = Baicalin.svg | ImageSize = 220 | IUPACName = 5,6-Dihydroxy-4-oxoflav-2-en-7-yl β-D-glucopyranosiduronic acid | SystematicName = (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 | OtherNames = Baicalein 7-O-glucuronide; 5,6-Dihydroxy-4-oxygen-2-phenyl-4H-1-benzopyran-7-β-D-glucopyranose acid |Section1={{Chembox Identifiers | 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 | InChIKey = IKIIZLYTISPENI-ZFORQUDYBD | CASNo_Ref = | CASNo = 21967-41-9 | ChEBI_Ref = | ChEBI = 2981 | EC_number = 606-866-1 | KEGG = C10025 | Beilstein = 70480 | 3DMet = | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = IKIIZLYTISPENI-ZFORQUDYSA-N | PubChem = 64982 | ChemSpiderID_Ref = | ChemSpiderID = 58507 | ChEMBL_Ref = | ChEMBL = 485818 | UNII_Ref = | UNII = 347Q89U4M5 | SMILES = O=C3\C=C(/Oc2cc(O[C@@H]1OC@HC@@HC@H[C@H]1O)c(O)c(O)c23)c4ccccc4 |Section2={{Chembox Properties | C = 21 | H = 18 | O = 11 | Appearance = | Density = | MeltingPtC = 202 to 205 | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | GHSPictograms = | GHSSignalWord = Warning | HPhrases = | PPhrases = | MainHazards = | FlashPt = | AutoignitionPt = }} Baicalin is the glucuronide of the polyphenolic compound baicalein.

Natural occurrences

Baicalin is found in several species in the genus Scutellaria, including Scutellaria baicalensis, and Scutellaria lateriflora. There are 10 mg/g baicalin in Scutellaria galericulata leaves. It is also present in the bark isolate of the Oroxylum indicum tree.

Medical uses

Baicalin is one of the chemical ingredients of at least two herbal supplements: Shuanghuanglian and Sho-Saiko-To, which is a Chinese classic herbal formula, and listed in Japan as Kampo medicine.

Baicalin, along with its aglycone baicalein, is a positive allosteric modulator of the benzodiazepine site and/or a non-benzodiazepine site of the GABAA receptor. In mice, baicalin produces anxiolytic effects without sedative or myorelaxant effects. It is thought that baicalin, along with other flavonoids, may underlie the anxiolytic effects of S. baicalensis and S. lateriflora.

Baicalin is a known prolyl endopeptidase inhibitor. It induces apoptosis in pancreatic cancer cells.

References

References

  1. (2020). "Anti-SARS-CoV-2 activities in vitro of Shuanghuanglian preparations and bioactive ingredients". Acta Pharmacologica Sinica.
  2. P.H. and Horhammer, L., Hager's Handbuch der Pharmazeutischen Praxis, Vols. 2-6, Springer-Verlag, Berlin, 1969-1979
  3. (2002). "Two flavones from Scutellaria baicalensis Georgi and their binding affinities to the benzodiazepine site of the GABAA receptor complex". Pharmazie.
  4. (2000). "Interaction of flavones from the roots of Scutellaria baicalensis with the benzodiazepine site". Planta Med..
  5. (1 January 2004). "Complementary and Alternative Approaches to Biomedicine". Springer Science & Business Media.
  6. (2006). "Anxiolytic-Like Effect of baicalin and its additivity with other anxiolytics". Planta Med..
  7. (2003). "Anxiolytic-like effects of baicalein and baicalin in the Vogel conflict test in mice". Eur. J. Pharmacol..
  8. (2003). "Phytochemical and biological analysis of skullcap (Scutellaria lateriflora L.): a medicinal plant with anxiolytic properties". Phytomedicine.
  9. Stefanie Schwartz. (9 January 2008). "Psychoactive Herbs in Veterinary Behavior Medicine". John Wiley & Sons.
  10. (2008). "Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor". Bioorganic & Medicinal Chemistry.
  11. (2011). "Baicalein, a component of Scutellaria baicalensis, induces apoptosis by Mcl-1 down-regulation in human pancreatic cancer cells". Biochim Biophys Acta.

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anxiolyticsflavone-glycosidesflavonoid-glucuronidesgabaa-receptor-positive-allosteric-modulators