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MedKoo Cat#: 574114 | Name: Ligustroflavone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ligustroflavone is an apigenin triglycoside that increases parathyroid hormone (PTH) release and inhibits calcium influx. It increases serum PTH, as well as serum and bone calcium levels, in a streptozotocin-induced mouse model of diabetes with osteoporosis. It also reduces increases in the expression and levels of the extracellular calcium sensing receptor (CaSR) in the kidney of diabetic osteoporotic mice. Ligustroflavone decreases infarct volume in a rat model of ischemic stroke and decreases the levels of the necroptosis-associated proteins RIPK3 and MLKL.

Chemical Structure

Ligustroflavone
Ligustroflavone
CAS#260413-62-5

Theoretical Analysis

MedKoo Cat#: 574114

Name: Ligustroflavone

CAS#: 260413-62-5

Chemical Formula: C33H40O18

Exact Mass: 724.2215

Molecular Weight: 724.67

Elemental Analysis: C, 54.70; H, 5.56; O, 39.74

Price and Availability

Size Price Availability Quantity
5mg USD 285.00 2 Weeks
10mg USD 500.00 2 Weeks
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Related CAS #
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Synonym
Ligustroflavone
IUPAC/Chemical Name
7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
InChi Key
NULBHTHMVOCGOE-ZBCCAYPVSA-N
InChi Code
InChI=1S/C33H40O18/c1-11-22(37)25(40)28(43)31(46-11)45-10-20-24(39)27(42)30(51-32-29(44)26(41)23(38)12(2)47-32)33(50-20)48-15-7-16(35)21-17(36)9-18(49-19(21)8-15)13-3-5-14(34)6-4-13/h3-9,11-12,20,22-35,37-44H,10H2,1-2H3/t11-,12-,20+,22-,23-,24+,25+,26+,27-,28+,29+,30+,31+,32-,33+/m0/s1
SMILES Code
OC1=CC=C(C(OC2=C3C(O)=CC(O[C@H]4[C@H](O[C@]5([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]6[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O6)O4)=C2)=CC3=O)C=C1
Appearance
A crystalline solid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Ligustroflavone, extracted from Ligustrum lucidum, is a potential candidate as calcium-sensing receptor (CaSR) antagonist.
In vitro activity:
Moreover, immunohistochemical, immunofluorescent and Western blot results showed that LF reduced the expressions of hepatic stellate cells specific marker proteins, including collagen I and α-SMA in vivo and in vitro. In addition, LF markedly suppressed TGF-β1-upregulated protein expressions of TβR I, TβR II, P-Smad2, P-Smad3 and Smad4 in LX-2 cells. Reference: Chin J Nat Med. 2021 Mar;19(3):170-180. https://pubmed.ncbi.nlm.nih.gov/33781450/
In vivo activity:
A rat model of ischemic stroke was established by middle cerebral artery occlusion (MCAO), which showed ischemic injury (increase in neurological deficit score and infarct volume) and upregulation of necroptosis-associated proteins (RIPK1, RIPK3 and MLKL/p-MLKL). Administration of ligustroflavone (30 mg/kg, i.g.) 15 min before ischemia evidently improved neurological function, reduced infarct volume, and decreased the levels of necroptosis-associated proteins except the RIPK1. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2019 Sep;392(9):1085-1095. https://pubmed.ncbi.nlm.nih.gov/31055628/
Solvent mg/mL mM comments
Solubility
DMF 30.0 41.40
DMSO 77.5 106.95
DMSO:PBS (pH 7.2) (1:5) 0.2 0.22
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 724.67 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Kang R, Tian W, Cao W, Sun Y, Zhang HN, Feng YD, Li C, Li ZZ, Li XQ. Ligustroflavone ameliorates CCl4-induced liver fibrosis through down-regulating the TGF-β/Smad signaling pathway. Chin J Nat Med. 2021 Mar;19(3):170-180. doi: 10.1016/S1875-5364(21)60018-3. PMID: 33781450. 2. Zhang YY, Liu WN, Li YQ, Zhang XJ, Yang J, Luo XJ, Peng J. Ligustroflavone reduces necroptosis in rat brain after ischemic stroke through targeting RIPK1/RIPK3/MLKL pathway. Naunyn Schmiedebergs Arch Pharmacol. 2019 Sep;392(9):1085-1095. doi: 10.1007/s00210-019-01656-9. Epub 2019 May 5. PMID: 31055628. 3. Feng R, Ding F, Mi XH, Liu SF, Jiang AL, Liu BH, Lian Y, Shi Q, Wang YJ, Zhang Y. Protective Effects of Ligustroflavone, an Active Compound from Ligustrum lucidum, on Diabetes-Induced Osteoporosis in Mice: A Potential Candidate as Calcium-Sensing Receptor Antagonist. Am J Chin Med. 2019;47(2):457-476. doi: 10.1142/S0192415X1950023X. Epub 2019 Mar 5. PMID: 30834778.
In vitro protocol:
1. Kang R, Tian W, Cao W, Sun Y, Zhang HN, Feng YD, Li C, Li ZZ, Li XQ. Ligustroflavone ameliorates CCl4-induced liver fibrosis through down-regulating the TGF-β/Smad signaling pathway. Chin J Nat Med. 2021 Mar;19(3):170-180. doi: 10.1016/S1875-5364(21)60018-3. PMID: 33781450.
In vivo protocol:
1. Zhang YY, Liu WN, Li YQ, Zhang XJ, Yang J, Luo XJ, Peng J. Ligustroflavone reduces necroptosis in rat brain after ischemic stroke through targeting RIPK1/RIPK3/MLKL pathway. Naunyn Schmiedebergs Arch Pharmacol. 2019 Sep;392(9):1085-1095. doi: 10.1007/s00210-019-01656-9. Epub 2019 May 5. PMID: 31055628. 2. Feng R, Ding F, Mi XH, Liu SF, Jiang AL, Liu BH, Lian Y, Shi Q, Wang YJ, Zhang Y. Protective Effects of Ligustroflavone, an Active Compound from Ligustrum lucidum, on Diabetes-Induced Osteoporosis in Mice: A Potential Candidate as Calcium-Sensing Receptor Antagonist. Am J Chin Med. 2019;47(2):457-476. doi: 10.1142/S0192415X1950023X. Epub 2019 Mar 5. PMID: 30834778.
1. Pieroni, A., and Pachaly, P. Isolation and structure elucidation of ligustroflavone, a new apigenin triglycoside from the leaves of Ligustrum vulgare L. Pharmazie 55(1), 78-80 (2000). 2. Feng, R., Ding, F., Mi, X.-H., et al. Protective effects of ligustroflavone, an active compound from Ligustrum lucidum, on diabetes-induced osteoporosis in mice: A potential candidate as calcium-sensing receptor antagonist. Am. J. Chin. Med. 47(2), 457-476 (2019). 3. Zhang, Y.-Y., Liu, W.-N., Li, Y.-Q., et al. Ligustroflavone reduces necroptosis in rat brain after ischemic stroke through targeting RIPK1/RIPK3/MLKL pathway. Naunyn Schmiedebergs Arch. Pharmacol. 392(9), 1085-1095 (2019).