Baicalin

As baicalin is a flavone glycoside, it is a flavonoid. It is the glucuronide of baicalein.

Not to be confused with baicalein.
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 InfoCard 100.133.557
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 mass 446.364 g·mol−1
Melting point 202 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 their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Natural occurrences

Baicalin is found in several species in the genus Scutellaria, including Scutellaria baicalensis,[1] and Scutellaria lateriflora. There are 10 mg/g baicalin in Scutellaria galericulata leaves.[2] 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[1] 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.[3][4][5] In mice, baicalin produces anxiolytic effects without sedative or myorelaxant effects.[6][7] It is thought that baicalin, along with other flavonoids, may underlie the anxiolytic effects of S. baicalensis and S. lateriflora.[8][9]

Baicalin is a known prolyl endopeptidase inhibitor.[10] It induces apoptosis in pancreatic cancer cells.[11]

References
  1. Su, Hai-xia; Yao, Sheng; Zhao, Wen-Feng; Li, Min-jun; Liu, Jia; Shang, Wei-Juan; Xie, Hang; Ke, Chang-Qiang; Hu, Hang-Chen; Gao, Mei-na; Yu, Kun-Qian; Liu, Hong; Shen, Jing-Shan; Tang, Wei; Zhang, Lei-ke; Xiao, Geng-fu; Ni, Li; Wang, Dao-wen; Zuo, Jian-Ping; Jiang, Hua-Liang; Bai, Fang; Wu, Yan; Ye, Yang; Xu, Ye-Chun (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.
  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.
  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.
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