Hypocrellin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-04093 |
| CAS | 77029-83-5 |
| Molecular Weight | 546.52 |
| Molecular Formula | C30H26O10 |
| Purity | 95% |
Online Inquiry
Description
Hypocrellin A is a natural perylene quinine photosensitizer isolated from Hypocrella bambusae. It is a potent PKC inhibitor.
Specification
| Synonyms | 7,19-dione; Isohypocrelin |
| Storage | Store at -20°C |
| IUPAC Name | 12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylhexacyclo[13.8.0.02,11.03,8.04,22.018,23]tricosa-1(15),2(11),3(8),4(22),5,9,16,18(23),20-nonaene-7,19-dione |
| Canonical SMILES | CC(=O)C1C2=C(C(=C3C(=O)C=C(C4=C5C(=CC(=O)C6=C(C(=C(CC1(C)O)C(=C56)C2=C43)OC)O)OC)OC)O)OC |
| InChI | InChI=1S/C30H26O10/c1-10(31)25-24-22-16-11(9-30(25,2)36)28(39-5)26(34)17-12(32)7-14(37-3)19(21(16)17)20-15(38-4)8-13(33)18(23(20)22)27(35)29(24)40-6/h7-8,25,34-36H,9H2,1-6H3 |
| InChI Key | VANSZAOQCMTTPB-UHFFFAOYSA-N |
Properties
| Appearance | Red Powder |
| Application | Antiviral Agents |
| Boiling Point | 894°C at 760 mmHg |
| Melting Point | 245-250°C |
| Density | 1.55 g/cm3 |
| Solubility | Soluble in ethanol, DMF, DMSO |
Reference Reading
1.High-efficiency biosynthesis of hypocrellin A in Shiraia sp. using gamma-ray mutagenesis.
Liu XY1, Shen XY2, Fan L1, Gao J3, Hou CL4. Appl Microbiol Biotechnol. 2016 Jan 15. [Epub ahead of print]
Hypocrellin A (HA), well known as one of the best natural pigments and bioactive agent to treat skin diseases, is further anticipated to play a vital role in photodynamic therapy (PDT) in anticancer and antiviral treatments. In this study, an HA-producing strain ZZZ816 (Shiraia sp.) was isolated from the moso bamboo (Phyllostachys edulis) seeds, and gamma irradiation was used to mutagenize spores of the original strain. After treatment with cobalt-60 gamma (60Coγ) with different doses (20, 50, 80, 100, 150, 180, 300, and 500 Gy), the 100 Gy was selected as the optimal condition, which led to 77.2 % lethality of spores and 35 % positive mutant frequency. The extracted compound of the most excellent HA-producing strain (H-4-2) was precisely analyzed by a combination of seven detection methods, and the maximum HA content was shown to reach 2018.3 mg/L. HA production in H-4-2 increased by 414.9 % compared to that of original strain ZZZ816 (392 mg/L) and was significantly higher than all the other industrial HA-producing strains in published reports.
2.Reference genes selection and relative expression analysis from Shiraia sp. SUPER-H168 productive of hypocrellin.
Deng H1, Gao R1, Liao X2, Cai Y3. Gene. 2016 Apr 10;580(1):67-72. doi: 10.1016/j.gene.2016.01.019. Epub 2016 Jan 15.
Shiraia bambusicola is an essential pharmaceutical fungus due to its production of hypocrellin with antiviral, antidepressant, and antiretroviral properties. Based on suitable reference gene (RG) normalization, gene expression analysis enables the exploitation of significant genes relative to hypocrellin biosynthesis by quantitative real-time polymerase chain reaction. We selected and assessed nine candidate RGs in the presence and absence of hypocrellin biosynthesis using GeNorm and NormFinder algorithms. After stepwise exclusion of unstable genes, GeNorm analysis identified glyceraldehyde-3-phosphate dehydrogenase (GAPDH) and cytochrome oxidase (CyO) as the most stable expression, while NormFinder determined 18S ribosomal RNA (18S rRNA) as the most appropriate candidate gene for normalization. Tubulin (Tub) was observed to be the least stable gene and should be avoided for relative expression analysis. We further analyzed relative expression levels of essential proteins correlative with hypocrellin biosynthesis, including polyketide synthase (PKS), O-methyltransferase (Omef), FAD/FMN-dependent oxidoreductase (FAD), and monooxygenase (Mono).
3.Rational assembly of a biointerfaced core@shell nanocomplex towards selective and highly efficient synergistic photothermal/photodynamic therapy.
Qin C1, Fei J, Wang A, Yang Y, Li J. Nanoscale. 2015 Dec 21;7(47):20197-210. doi: 10.1039/c5nr06501a. Epub 2015 Nov 17.
To optimize synergistic cancer therapy, we rationally assemble an inorganic-organic nanocomplex using a folate-modified lipid bilayer spread on photosensitizer-entrapped mesoporous silica nanoparticle (MSN) coated gold nanorods (AuNRs). In this hybrid bioconjugate, the large specific surface area and pore size of AuNR@MSN guarantee a high loading capacity of small photosensitive molecules. The modification with selective mixed liposomes on the surface of AuNR@MSN enables faster cellular internalization and enhancement of endocytosis. Under one-time NIR two-photon illumination, AuNR-mediated hyperthermia can kill cancer cells directly. Meanwhile, the loaded photosensitizer, hypocrellin B, generates two kinds of reactive oxygen species (ROS) to induce cell apoptosis. Remarkably, hyperthermia can improve the yield of ROS. After intravenous injection of this bioconjugate into female BALB/c nude mice followed by laser irradiation (808 nm, 1.3 W cm(-2), 6 min), the tumor growth is suppressed completely.
4.De Novo Transcriptome Assembly in Shiraia bambusicola to Investigate Putative Genes Involved in the Biosynthesis of Hypocrellin A.
Zhao N1, Lin X2, Qi SS3, Luo ZM4, Chen SL5, Yan SZ6. Int J Mol Sci. 2016 Feb 27;17(3). pii: E311. doi: 10.3390/ijms17030311.
Shiraia bambusicola is a species of the monotypic genus Shiraia in the phylum Ascomycota. In China, it is known for its pharmacological properties that are used to treat rheumatic arthritis, sciatica, pertussis, tracheitis and so forth. Its major medicinal active metabolite is hypocrellin A, which exhibits excellent antiviral and antitumor properties. However, the genes involved in the hypocrellin A anabolic pathways were still unknown due to the lack of genomic information for this species. To investigate putative genes that are involved in the biosynthesis of hypocrellin A and determine the pathway, we performed transcriptome sequencing for Shiraia bambusicola S4201-W and the mutant S4201-D1 for the first time. S4201-W has excellent hypocrellin A production, while the mutant S4201-D1 does not. Then, we obtained 38,056,034 and 39,086,896 clean reads from S4201-W and S4201-D1, respectively. In all, 17,923 unigenes were de novo assembled, and the N50 length was 1970 bp.
Recommended Products
| BBF-05862 | Epirubicin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
