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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-4
H -1-benzopyran-7-β-
D -glucopyranose acid
Identifiers
70480
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.133.557
EC Number
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
Y Key: IKIIZLYTISPENI-ZFORQUDYSA-N
Y 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
C 21 H 18 O 11
Molar mass
446.364 g·mol−1
Melting point
202 to 205 °C (396 to 401 °F; 475 to 478 K)
Hazards
GHS labelling :
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).
Chemical compound
As baicalin is a
flavone
glycoside , it is a
flavonoid . It is the
glucuronide of
baicalein .
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 .[
citation needed ]
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
^
a
b Su 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 .
^ P.H. and Horhammer, L., Hager's Handbuch der Pharmazeutischen Praxis, Vols. 2-6, Springer-Verlag, Berlin, 1969-1979
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ Stefanie Schwartz (9 January 2008).
Psychoactive Herbs in Veterinary Behavior Medicine . John Wiley & Sons. pp. 139–.
ISBN
978-0-470-34434-7 .
^ 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 .
^ 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 .
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
3-Hydroxybutanal
α-EMTBL
AA-29504
Alogabat
Avermectins (e.g.,
ivermectin )
Bromide compounds (e.g.,
lithium bromide ,
potassium bromide ,
sodium bromide )
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Darigabat
DEABL
Deuterated etifoxine
Dihydroergolines (e.g.,
dihydroergocryptine ,
dihydroergosine ,
dihydroergotamine ,
ergoloid (dihydroergotoxine) )
DS2
Efavirenz
Etazepine
Etifoxine
Fenamates (e.g.,
flufenamic acid ,
mefenamic acid ,
niflumic acid ,
tolfenamic acid )
Fluoxetine
Flupirtine
Hopantenic acid
KRM-II-81
Lanthanum
Lavender oil
Lignans (e.g.,
4-O-methylhonokiol ,
honokiol ,
magnolol ,
obovatol )
Loreclezole
Menthyl isovalerate (validolum)
Monastrol
Niacin
Niacinamide
Org 25,435
Phenytoin
Propanidid
Retigabine (ezogabine)
Safranal
Seproxetine
Stiripentol
Sulfonylalkanes (e.g.,
sulfonmethane (sulfonal) ,
tetronal ,
trional )
Terpenoids (e.g.,
borneol )
Topiramate
Valerian constituents (e.g.,
isovaleric acid ,
isovaleramide ,
valerenic acid ,
valerenol )