Gardenin A

Modify Date: 2024-01-04 10:57:32

Gardenin A Structure
Gardenin A structure
Common Name Gardenin A
CAS Number 21187-73-5 Molecular Weight 418.39400
Density 1.3g/cm3 Boiling Point 624.2ºC at 760 mmHg
Molecular Formula C21H22O9 Melting Point 162-163ºC
MSDS N/A Flash Point 218.5ºC

 Use of Gardenin A


Gardenin A is an orally active and synthetic PMF analogue with the neurotrophic effect for neurite outgrowth and neuronal differentiation. Gardenin A promotes neuritogenesis via activating MAPK/ERK, PKC, and PKA, but not TrkA, CREB signaling pathways. Gardenin A also has sedative, anxiolytic, antidepressant, and anticonvulsant effects[1][2].

 Names

Name 5-hydroxy-6,7,8-trimethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
Synonym More Synonyms

 Gardenin A Biological Activity

Description Gardenin A is an orally active and synthetic PMF analogue with the neurotrophic effect for neurite outgrowth and neuronal differentiation. Gardenin A promotes neuritogenesis via activating MAPK/ERK, PKC, and PKA, but not TrkA, CREB signaling pathways. Gardenin A also has sedative, anxiolytic, antidepressant, and anticonvulsant effects[1][2].
Related Catalog
In Vitro Gardenin A (10-20 μM; 48 h) 可诱导 PC12 细胞神经突生长,(10 μM; 24 小时和 48 小时) 还增加神经元分化和突触形成标记蛋白、生长相关蛋白-43 (GAP-43) 和突触素的表达[1]。 Gardenin A (10 μM; 30-120分钟) 显著诱导环 AMP 反应元件结合蛋白(CREB) 的磷酸化和 CRE 介导的转录,这是通过抑制剂 2-萘酚AS-E 磷酸盐 (KG-501) 或使用 CREB siRNA 来抑制的[1]。 Gardenin A (10 μM; 15-120分钟) 增加 ERK 磷酸化水平,提高 PKA 和 PKC 活性[1]。 Cell Viability Assay[1] Cell Line: PC12 cells Concentration: 2, 5, 10, 20 μM Incubation Time: 48 hours Result: showed cell growth supporting effect at higher concentrations (10-20 µM) and did not exert detectable 237 cytotoxicity on PC12 cells after 48 h incubation in low serum medium. Western Blot Analysis[1] Cell Line: PC12 cells Concentration: 10 μM Incubation Time: 0, 15, 30, 60, and 120 min Result: Significantly increased the phosphorylation of ERK1/2 (Thr202/Tyr204) at 15 min, subsequently reduced after 30 min. Increased PKC and PKA activity peaked at 15 min.Increased CREB phosphorylation.
In Vivo Gardenin A (0.1-25 mg/kg; 口服; 单剂量) 具有神经药理作用,包括镇静、抗焦虑、抗抑郁和抗惊厥作用的小鼠[2]。 栀子苷A (1-10 mg/kg; 口服; 单次剂量) 不影响小鼠的运动协调和延迟惊厥的发生[2]。 Animal Model: Male Balb/c mice (24-32 g)[2] Dosage: 1 mg/kg, 10 mg/kg, 25 mg/kg Administration: Oral gavage; single dose Result: Showed sedative effects at a dose of 25 mg/kg, which increased the duration of sleep but did not alter sleep onset.
References

[1]. Chiu SP, et al. Neurotrophic action of 5-hydroxylated polymethoxyflavones: 5-demethylnobiletin and gardenin A stimulate neuritogenesis in PC12 cells. J Agric Food Chem. 2013 Oct 2;61(39):9453-63.  

[2]. Alonso-Castro AJ, et al. Evaluation of the neuropharmacological effects of Gardenin A in mice. Drug Dev Res. 2020 Aug;81(5):600-608.  

 Chemical & Physical Properties

Density 1.3g/cm3
Boiling Point 624.2ºC at 760 mmHg
Melting Point 162-163ºC
Molecular Formula C21H22O9
Molecular Weight 418.39400
Flash Point 218.5ºC
Exact Mass 418.12600
PSA 105.82000
LogP 3.21720
Vapour Pressure 3.57E-16mmHg at 25°C
Index of Refraction 1.573
Storage condition -20°C

 Safety Information

Hazard Codes T+
HS Code 2914509090

 Synthetic Route

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Gardenin A Structure

Gardenin A

CAS#:21187-73-5

Literature: Banerji, J.; Das, B.; Chakrabarty, R.; Jha, H. C. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988 , vol. 27, # 1-12 p. 597 - 599

 Precursor & DownStream

Precursor  1

DownStream  1

 Customs

HS Code 2914509090
Summary HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

 Synonyms

Gardenin A
5OH3'4'5'6,7,8-hexMeO-Flavone
3',4',5',6,7,8-Hexamethoxy-5-hydroxyflavone
Gardenin
5-hydroxy-6,7,8,3',4',5'-hexamethoxyflavone
Flavone,5-hydroxy-3',4',5',6,7,8-hexamethoxy
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