Hyperforin

Names

[ Name ]:
Hyperforin

[Synonym ]:
(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

Biological Activity

[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.

Chemical & Physical Properties

[ 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

Safety Information

[ 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

Articles

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J. Nutr. Biochem. 25(9) , 923-33, (2014)

Isorhamnetin is an O-methylated flavonol present in fruit and vegetables. We recently reported the identification of isorhamnetin as an activator of the human pregnane X receptor (PXR), a known target...

Phytochemical analysis and in vitro biological activity of three Hypericum species from the Canary Islands (Hypericum reflexum, Hypericum canariense and Hypericum grandifolium).

Fitoterapia 100 , 95-109, (2015)

In the present work we carried out a phytochemical and biological investigation on three Hypericum species, i.e. Hypericum reflexum, Hypericum canariense and Hypericum grandifolium, from the Canary Is...

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Endocrinology 155(6) , 2052-63, (2014)

25-Hydroxyvitamin D3 (25OHD3) is used as a clinical biomarker for assessment of vitamin D status. Blood levels of 25OHD3 represent a balance between its formation rate and clearance by several oxidati...