11079-53-1

11079-53-1 structure

Name: Hyperforin
Chemical Name: hyperforin
CAS Number: 11079-53-1
Molecular Formula: C₃₅H₅₂O₄
Molecular Weight: 536.785
Catalog: Biochemical Chinese herbal medicine ingredients
Create Date: 2018-07-21 09:57:09
Modify Date: 2024-01-02 11:50:39
Hyperforin is a transient receptor canonical 6 (TRPC6) channels activator. Hyperforin modulates Ca2+ levels by activating Ca2+-conducting non-selective canonical TRPC6 channels. Hyperforin also shows diverse pharmacological activities including anti-depression, anti-tumor, anti-dementia, anti-diabetes. Hyperforin modulates γδ T cells to secret IL-17α, improves Imiquimod (HY-B0180)-induced psoriasis-like mice model[1][2][3][4][5].

Name	hyperforin
Synonyms	(1R,5S,6R,7S)-4-Hydroxy-6-methyl-1,3,7-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-pentenyl)bicyclo[3.3.1]non-3-ene-2,9-dione (1R,5S,6R,7S)-4-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione Hyperforin (1R,5S,6R,7S)-4-Hydroxy-5-isobutyryl-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione (1R,5S,6R,7S)-4-Hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-enyl)-6-(4-methylpent-3-enyl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione Bicyclo[3.3.1]non-3-ene-2,9-dione, 4-hydroxy-6-methyl-1,3,7-tris(3-methyl-2-buten-1-yl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-penten-1-yl)-, (1R,5S,6R,7S)- MFCD01861497 (1R,5S,6R,7S)-4-Hydroxy-5-isobutyryl-6-methyl-1,3,7-tris(3-methyl-2-buten-1-yl)-6-(4-methyl-3-penten-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

Description	Hyperforin is a transient receptor canonical 6 (TRPC6) channels activator. Hyperforin modulates Ca2+ levels by activating Ca2+-conducting non-selective canonical TRPC6 channels. Hyperforin also shows diverse pharmacological activities including anti-depression, anti-tumor, anti-dementia, anti-diabetes. Hyperforin modulates γδ T cells to secret IL-17α, improves Imiquimod (HY-B0180)-induced psoriasis-like mice model[1][2][3][4][5].
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel Research Areas >> Inflammation/Immunology Research Areas >> Neurological Disease
Target	TRPC6[1]
In Vitro	Hyperforin 具有多向作用机制。它阻断配体门控 (GABA、NMDA 和 AMPA 受体) 和电压门控通道(Ca2+， K+， Na+) 的电导[2]。 Hyperforin (0.1, 1,10 μM; 2 h) 降低体外培养的小鼠脾 γδ T 细胞中 IL-17A 的表达和分泌[3]。 Hyperforin (0.1, 1,10 μM; 2 h) 抑制 TNF-α 刺激的 HaCaT 细胞中 MAPK 和 STAT3 通路的磷酸化[3]。 Hyperforin (IC50=3.7 μmol/L) 抑制 HDMEC 微血管管的形成和增殖，呈剂量依赖性，无毒性作用[4]。 Western Blot Analysis[3] Cell Line: HaCaT cells Concentration: 0.1, 1, 10 μM; with or without 10, 20 ng/mL TNF-α Incubation Time: 2 hours Result: Reduced the expressions of p-p38, p-ERK, p-JNK, and p-STAT3, especially at the dosage of 10 μM.
In Vivo	Hyperforin (5 mg/kg; 腹腔注射; 每天 1 次, 共 7 天) 能够改善 Imiquimod (HY-B0180) 诱导的小鼠银屑病皮损情况，抑制炎症细胞浸润和炎症因子释放[3]。 Animal Model: IMQ-induced psoriasis-like mice model[3] Dosage: 5 mg/kg Administration: Intraperitoneal injection; once daily for 7 days Result: Significantly ameliorated skin lesion throughout the treatment period, demonstrated by the reduced severity score of skin inflammation. Suppressed infiltration of CD3+ T cells and downregulated expression of Il1, Il6, Il23, Il17a, Il22, antimicrobial peptides (AMPs) in the skin lesion.
References	[1]. Heiser JH, et al. TRPC6 channel-mediated neurite outgrowth in PC12 cells and hippocampal neurons involves activation of RAS/MEK/ERK, PI3K, and CAMKIV signaling. J Neurochem. 2013 Nov;127(3):303-13. [2]. Pochwat B, et al. Hyperforin Potentiates Antidepressant-Like Activity of Lanicemine in Mice. Front Mol Neurosci. 2018 Dec 12;11:456. [3]. Zhang S, et al. Hyperforin Ameliorates Imiquimod-Induced Psoriasis-Like Murine Skin Inflammation by Modulating IL-17A-Producing γδ T Cells. Front Immunol. 2021 May 5;12:635076. [4]. Adam P, et al. Biosynthesis of hyperforin in Hypericum perforatum. J Med Chem. 2002 Oct 10;45(21):4786-93. [5]. Li XX, et al. Hyperforin: A natural lead compound with multiple pharmacological activities. Phytochemistry. 2023 Feb;206:113526.

Density	1.0±0.1 g/cm3
Boiling Point	616.8±55.0 °C at 760 mmHg
Melting Point	79-80ºC
Molecular Formula	C₃₅H₅₂O₄
Molecular Weight	536.785
Flash Point	340.9±28.0 °C
Exact Mass	536.386536
PSA	71.44000
LogP	12.30
Vapour Pressure	0.0±4.0 mmHg at 25°C
Index of Refraction	1.518

Symbol	GHS02, GHS06, GHS08
Signal Word	Danger
Hazard Statements	H225-H301 + H311 + H331-H370
Precautionary Statements	P210-P280-P302 + P352 + P312-P304 + P340 + P312-P370 + P378-P403 + P235
Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	F,T
Risk Phrases	11-23/24/25-39/23/24/25
Safety Phrases	7-16-36/37-45
RIDADR	UN1230 - class 3 - PG 2 - Methanol
WGK Germany	3
HS Code	29144000

11079-53-1	238074-03-8
612547-11-2	68324-06-1