555-55-5 Usage
Description
HISPIDIN is a polyphenol originally isolated from P. hispidus, a medicinal mushroom, Phellinus linteus. It is a phenolic compound that serves as a naturally occurring precursor to fungal luciferin, responsible for luminosity in mushrooms. HISPIDIN possesses diverse biological activities, including antioxidant, anti-inflammatory, and cytoprotective properties.
Uses
Used in Pharmaceutical Applications:
HISPIDIN is used as an antioxidant agent for its ability to scavenge radicals at 14.47 equivalents of trolox in a trolox equivalent antioxidant capacity (TEAC) assay. It also exhibits anti-inflammatory properties by inhibiting the transcriptional activity of NF-κB, decreasing inducible nitric oxide synthase (iNOS) expression, and reducing the generation of reactive oxygen species (ROS) in LPS-induced macrophage RAW 264.7 cells.
Used in Cytoprotection:
HISPIDIN is used as a cytoprotective agent for its ability to inhibit apoptosis and increase insulin secretion in hydrogen peroxide-treated RINm5F pancreatic β-cells.
Used in Enzyme Inhibition:
HISPIDIN is used as an enzyme inhibitor for its ability to inhibit protein kinase C β (PKCβ; IC50 = 2 μM), β-secretase (BACE1; IC50 = 4.9 μM), and prolyl endopeptidase (PE; IC50 = 16 μM) with no activity against alkaline phosphatase.
Used in Bioluminescence Research:
HISPIDIN is used as a bioluminescence precursor in the study of fungal luciferin, which is responsible for the luminosity in mushrooms, providing insights into the bioluminescent properties of various fungi.
Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, HISPIDIN's antioxidant, anti-inflammatory, and cytoprotective properties may suggest potential applications in cancer research and treatment, warranting further investigation.
Biochem/physiol Actions
Hispidin exhibits robust antioxidant, anticancer and antidiabetic properties. It has the ability to guard against peroxynitrite-mediated cytotoxicity, DNA damage and the development of hydroxyl radicals.
in vitro
in previous study hispidin was found to reduce cell viability in both mouse and human colon cancer cells, and the apoptotic cell morphological changes were also observed. these results showed accumulation of the sub-g1 cell population and increase in early apoptosis dose-dependently. moreover, hispidin could induce apoptosis via up-regulation of both intrinsic and extrinsic apoptotic pathways. although the molecular mechanism underlying hispidin-induced apoptosis was known to involve the generation of ros, however hispidin was not able to display any apoptosis in the pre-treatment with n-acetyl-l-cysteine, a ros scavenger [1].
in vivo
previous animal study found that the treatment with pkc-activating agent phorbol-12-myristate-13-acetate could attenuate exendin-4-induced relaxations and reduced glp-1r expression in wistar-kyoto rat arteries, which were reversed by hispidin [2].
references
[1] lim jh, lee ym, park sr, kim dh, lim bo. anticancer activity of hispidin via reactive oxygen species-mediated apoptosis in colon cancer cells. anticancer res. 2014 aug;34(8):4087-93.[2] liu l, liu j, gao y, ng cf, yu x, dou d, huang y. protein kinase cβ mediates downregulated expression of glucagon-like peptide-1 receptor in hypertensive rat renal arteries. j hypertens. 2015 apr;33(4):784-90; discussion 790.
Check Digit Verification of cas no
The CAS Registry Mumber 555-55-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 5 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 555-55:
(5*5)+(4*5)+(3*5)+(2*5)+(1*5)=75
75 % 10 = 5
So 555-55-5 is a valid CAS Registry Number.
InChI:InChI=1/C13H10O5/c14-9-6-10(18-13(17)7-9)3-1-8-2-4-11(15)12(16)5-8/h1-7,15-17H/b3-1+
555-55-5Relevant articles and documents
A β-secretase (BACE1) inhibitor hispidin from the mycelial cultures of Phellinus linteus
Park, In-Hye,Jeon, So-Young,Lee, Hee-Ju,Kim, Sang-In,Song, Kyung-Sik
, p. 143 - 146 (2004)
In the course of screening for anti-dementia agents from natural products, a β-secretase (BACE1) inhibitor was isolated from the culture broth of Phellinus linteus and identified as hispidin. It showed an IC50 value of 4.9 × 10-6 M and a Ki value of 8.4 × 10 -6 M. The compound was a non-competitive inhibitor. Hispidin also inhibited a prolyl endopeptidase (IC50 = 1.6 × 10-5 M, Ki = 2.4 × 10-5 M), but it was less inhibitory to α-secretase (TACE) and other serine proteases such as chymotrypsin, trypsin, and elastase.
Anti-obesity effects of hispidin and alpinia zerumbet bioactives in 3t3-l1 adipocytes
Tu, Pham Thi Be,Tawata, Shinkichi
, p. 16656 - 16671 (2015/02/19)
Obesity and its related disorders have become leading metabolic diseases. In the present study, we used 3T3-L1 adipocytes to investigate the anti-obesity activity of hispidin and two related compounds that were isolated from Alpinia zerumbet (alpinia) rhizomes. The results showed that hispidin, dihydro-5,6-dehydrokawain (DDK), and 5,6-dehydrokawain (DK) have promising anti-obesity properties. In particular, all three compounds significantly increased intracellular cyclic adenosine monophosphate (cAMP) concentrations by 81.2% ± 0.06%, 67.0% ± 1.62%, and 56.9% ± 0.19%, respectively. Hispidin also stimulated glycerol release by 276.4% ± 0.8% and inhibited lipid accumulation by 47.8% ± 0.16%. Hispidin and DDK decreased intracellular triglyceride content by 79.5% ± 1.37% and 70.2% ± 1.4%, respectively, and all three compounds inhibited glycerol-3-phosphate dehydrogenase (GPDH) and pancreatic lipase, with hispidin and DDK being the most potent inhibitors. Finally, none of the three compounds reduced 3T3-L1 adipocyte viability. These results highlight the potential for developing hispidin and its derivatives as anti-obesity compounds.
