Amentoflavone (Didemethyl-ginkgetin) | GABA(A) Modulator

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CAS No. :	1617-53-4
Formula :	C₃₀H₁₈O₁₀
M.W :	538.46
SMILES Code :	O=C1C=C(C2=CC=C(O)C=C2)OC3=C(C4=CC(C5=CC(C6=C(O)C=C(O)C=C6O5)=O)=CC=C4O)C(O)=CC(O)=C13
Synonyms :	Didemethyl-ginkgetin; NSC 295677; 38Biapigenin
MDL No. :	MFCD00017470
InChI Key :	YUSWMAULDXZHPY-UHFFFAOYSA-N
Pubchem ID :	5281600

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

3T3-L1 pre-adipocytes	1-10 µg/ml	0-8, 0-2, 2-4, 4-8 days	AMF inhibited 3T3-L1 adipocyte differentiation, reduced oil droplet accumulation, and suppressed the expression of C/EBPβ, PPARγ, and C/EBPα.	PMC5117752
BV2 microglial cells	10 μM	1 hour	Amentoflavone inhibited LPS-induced microglial activation, migration, and inflammatory response by regulating the TLR4/MyD88/NF-κB pathway and enhanced Nrf2/HO-1 levels	PMC9747320
A549 cells	30 μg/mL	1 hour, 2 hours, 4 hours, and 6 hours	To evaluate the cellular uptake of AMF and AMF-loaded TPGS/soluplus mixed micelles in A549 cells. The results showed that the cellular uptake of AMF monomer increased significantly with time, while that of AMF-loaded mixed micelles increased in 1-4 hours and remained almost unchanged in 4-6 hours. The cellular uptake of AMF-loaded mixed micelles was significantly lower than that of AMF monomer (p<0.05).	PMC6968485
A549 cells	0.5-4 µg/mL	2 hours	To evaluate the protective effect of AMF against AerA-mediated cytotoxicity, results showed that AMF significantly reduced AerA-mediated cell death.	PMC11900166
A549 cells	2000 μg/mL to 15.6 μg/mL	24 hours	To evaluate the cytotoxicity of AMF and AMF-loaded TPGS/soluplus mixed micelles on A549 cells. The results showed that the IC50 value of AMF-loaded mixed micelles (6.11 ± 0.74 μg/mL) was significantly lower than that of AMF monomer (83.09 ± 0.65 μg/mL), indicating that the mixed micelles had stronger toxicity to A549 cells.	PMC6968485
A549 cells	0, 10, 25, 50 µM	24 hours	Evaluate the inhibitory effect of AF on influenza virus infection, results showed AF dose-dependently inhibited GFP expression.	PMC11595079
RAW 264.7 cells	0, 10, 25, 50 µM	24 hours	Evaluate the inhibitory effect of AF on influenza virus infection, results showed AF dose-dependently inhibited GFP expression.	PMC11595079
Human umbilical vein endothelial cells (HUVECs)	18.587 μM	24 hours	To evaluate the cytoprotective effects of Amentoflavone on LPS-induced injury in HUVECs. Results showed that Amentoflavone significantly reduced NO and MDA levels and increased SOD activity, indicating its protective effects against inflammation and oxidative damage.	PMC5037791
HK-2 cells	1 or 2 μM	24 hours	AME significantly suppressed the cytotoxic effects of cisplatin on HK-2 cells and protected cells from oxidative stress by activating the Nrf2 antioxidant pathway.	PMC11919867
MHCCLM3 cells	100, 200, 300 μM	24 hours	Amentoflavone inhibits the migratory and invasive capabilities of HCC cells in a dose-dependent manner	PMC11154840
MHCC97H cells	100, 200, 300 μM	24 hours	Amentoflavone inhibits the migratory and invasive capabilities of HCC cells in a dose-dependent manner	PMC11154840
Immortalized astrocytes	2, 10 µM	3 hours	To evaluate the effect of Amentoflavone on the cellular uptake of Aβ1-40 in astrocytes, results showed that Amentoflavone significantly increased the intracellular accumulation of Aβ1-40.	PMC9180170
HepG2 cells	9.30 μM, 13.94 μM, 18.59 μM	36 hours	To explore the mechanism by which AME improves insulin resistance in HepG2 cells. Results showed that AME significantly increased glucose consumption, upregulated the expression of PI3K, Akt, and pAkt, enhanced the activities of PFK-1, GCK, and PK, and reduced the activities of GSK-3, PEPCK, and G-6-Pase as well as the levels of IL-6, IL-8, TNF-α, and CRP.	PMC6274486
Endometrial carcinoma cells (KLE)	50, 75, 100 μM	48 hours	AF inhibited the viability and proliferation of KLE cells but promoted apoptosis and ferroptosis.	PMC9275900
BV2 microglial cells	10 μM	5.5 hours	Amentoflavone alleviates LPS-induced inflammatory response by inhibiting NLRP3 inflammasome	PMC6682693
Human epithelial colorectal adenocarcinoma (Caco2) cells	2-16 mg/ml	6 hours	Evaluate the protective effect of Amentoflavone on CPA and PFO-mediated cytotoxicity, results showed significant protection against cell injury	PMC7059699
Human epithelial colorectal adenocarcinoma (Caco2) cells	0 -64 mg/ml	6 hours	Evaluate the cytotoxicity of Amentoflavone on Caco-2 cells, results showed no cytotoxicity	PMC7059699
MDCK cells	0, 10, 50 µM	72 hours	Evaluate the inhibitory effect of AF on influenza virus plaque formation, results showed AF significantly inhibited plaque formation.	PMC11595079
BALB/c mouse peritoneal macrophages	0–22.3 µM	72 hours	Evaluate the cytotoxicity of Amentoflavone, no cytotoxicity was observed, and the selectivity index was greater than 10	PMC7950538
BALB/c mouse peritoneal macrophages	0–11.14 µM	72 hours	Evaluate the antileishmanial activity of Amentoflavone on intracellular amastigotes, IC50 was 2.3 ± 0.93 µM	PMC7950538

Wistar rats	High-fat diet-induced metabolic dysfunction model	Intraperitoneal injection	10 or 50 mg/kg	Once daily for 4 months	AMF attenuated high-fat diet-induced metabolic dysfunction in a dose-dependent manner, including reductions in fasting blood glucose, fasting insulin levels, HOMA-IR index, body weight, perirenal adipose tissue weight, and serum triglyceride content.	PMC5117752
Kunming mice	Epilepsy model	Intragastric administration	25 mg/kg	Once a day for 3 consecutive days	Amentoflavone effectively prevented pilocarpine-induced epilepsy in a Mice kindling model, suppressed nuclear factor-κB activation and expression, inhibited excessive discharge of hippocampal neurons resulting in a reduction in epileptic seizures, shortened attack time, and diminished loss and apoptosis of hippocampal neurons.	PMC4541246
BALB/c mice	Leishmaniasis model	Intralesional injection	0.05 mg/kgose	Every 4 days, total of 5 doses	Evaluate the therapeutic effect of Amentoflavone on leishmaniasis, intralesional treatment significantly reduced lesion size and parasite load	PMC7950538
Channel catfish	Aeromonas hydrophila infection model	Intraperitoneal injection	20 mg/kg	Every 12 hours for 3 days	To evaluate the protective effect of AMF against A. hydrophila infection, results showed that the mortality rate in the AMF-treated group was reduced by 35% compared to the positive control group.	PMC11900166
C57BL/6 mice	PTZ-induced chronic epilepsy model	Oral	25 mg/kg	Once every other day for a total of 15 injections (29 days)	Amentoflavone reduces seizure susceptibility, minimizes cognitive dysfunction, and blocks neuronal apoptosis by inhibiting NLRP3 inflammasome	PMC6682693
C57BL/6 mice	Cisplatin-induced acute kidney injury model	Intraperitoneal injection	5 or 10 mg/kg	Daily administration for 72 hours	AME significantly improved cisplatin-induced acute kidney injury by activating the Nrf2 antioxidant pathway and regulating ferroptosis and PANoptosis.	PMC11919867
BALB/c mice	Gas gangrene model	Subcutaneous injection	50 mg/kg	Three doses at 8-hour intervals	Evaluate the therapeutic effect of Amentoflavone on gas gangrene, results showed significant increase in survival rate, reduction in bacterial burden in tissues, and alleviation of histological damage	PMC7059699
Mice	Carrageenan-induced pleurisy and lung injury model	Intragastric administration	30 mg/kg or 50 mg/kg	Administered at 12-hour intervals for 4 hours	AMF ameliorated carrageenan-induced pleurisy and lung injury by activating Nrf2 and inhibiting the NF-κB and STAT3 pathways	PMC8883043
Mice	Diabetic mice induced by high fat diet and streptozotocin	Intragastric administration	20 mg/kg and 40 mg/kg	8 weeks	AME exerted anti-diabetic effects by regulating glucose and lipid metabolism, perhaps via anti-oxidant effects and activating the PI3K/Akt pathway	PMC6600559

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CAS No.: 1617-53-4

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CAS No.: 1617-53-4

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed