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Chemical Structure| 77029-83-5 Chemical Structure| 77029-83-5

Structure of Hypocrellin A
CAS No.: 77029-83-5

Chemical Structure| 77029-83-5

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Hypocrellin A is a natural product isolated and purified from the Hypocrella bambusae, with light-induced antitumor, antifungal and antiviral activities, showing photodynamic activity towards microorganisms.

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Product Citations

Product Citations

Greatens, Nicholas ; Murithi, Harun M ; Coyne, Danny ; Clough, Steven J ; Sulyok, Michael ; Okunowo, Wahab Oluwanisola , et al.

Abstract: The Dothideomycete pathogen Coniothyrium glycines causes red leaf blotch of soybean, a major disease in Africa. It is one of two fungal plant pathogens on the USDA PPQ Select Agents and Toxins list of pathogens important to the biosecurity of the United States, reflective of its potential to be highly destructive if introduced. Despite its importance, there are no published reports regarding the molecular basis of host infection. Examination of the C. glycines genome revealed a secondary metabolite gene cluster that is similar in gene content and organization to clusters that synthesize light-activated perylenequinone toxins, such as . Perylenequinones are non-host specific toxins that, upon exposure to light, generate reactive oxygen species, which have near-universal toxicity to plant hosts. Coniothyrium glycines isolates from eastern and southern Africa were cultured axenically under light and dark conditions. Light-grown cultures produced red-pink pigmentation typical of perylenequinones. Differential gene expression analysis showed that six of the eight genes in the biosynthetic gene cluster, including the polyketide synthase gene, were significantly upregulated in light. Liquid chromatography-mass spectrometry confirmed production of the perylenequinone elsinochrome A, a known virulence factor in other fungal pathogens. On leaves incubated in the dark, significantly fewer lesions formed and symptoms were delayed, compared to leaves incubated in the light. In addition, we identified orthologous gene clusters in more distantly related Dothideomycete plant pathogens where their presence was previously unknown, indicating a broader importance of these toxins to agriculture and fungal ecology. This work provides the first evidence that elsinochrome A may contribute to the virulence of C. glycines.

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Product Details of Hypocrellin A

CAS No. :77029-83-5
Formula : C30H26O10
M.W : 546.52
SMILES Code : COC(C1=O)=C2C3=C(C4=C5C(OC)=CC(O)=C6C5=C3C(CC(O)(C2C(C)=O)C)=C(C6=O)OC)C1=C(O)C=C4OC
MDL No. :MFCD00467740

Safety of Hypocrellin A

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Related Pathways of Hypocrellin A

epigenetics

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
A549 cells 0.08 μmol/L 4 hours To evaluate the anti-proliferative and apoptosis-inducing effects of HA-mediated photodynamic therapy on A549 cells. Results showed that HA significantly inhibited A549 cell proliferation under light irradiation, induced apoptosis accompanied by increased ROS generation, mitochondrial dysfunction, and caspase activation. Acta Pharm Sin B. 2019 Mar;9(2):279-293
A549 human lung cancer cells 10 µM 8 hours Evaluate the toxicity of Hypocrellin A on A549 cells and its inhibitory effect on the cytotoxicity of C. albicans SC5314, results showed that Hypocrellin A significantly inhibited the cytotoxicity of C. albicans SC5314 at 10 µM concentration. Microb Biotechnol. 2021 Mar;14(2):430-443
Candida albicans SC5314 10 µM 6 hours Evaluate the inhibitory effect of Hypocrellin A on mycelium formation of C. albicans SC5314, results showed that Hypocrellin A significantly inhibited mycelium formation at 10 µM concentration. Microb Biotechnol. 2021 Mar;14(2):430-443
NIH-3T3 cells 0.01, 0.02, 0.03, 0.04, 0.05 µM 8 hours To evaluate the cytotoxicity of TF-HA-CMC-PLGA NPs on TFR-negative NIH-3T3 cells. Results showed no significant difference in cytotoxicity between TF-HA-CMC-PLGA NPs and HA-CMC-PLGA NPs under light irradiation. Front Pharmacol. 2017 Nov 10;8:815
A549 cells 0.01, 0.02, 0.03, 0.04, 0.05 µM 8 hours To evaluate the cytotoxicity of TF-HA-CMC-PLGA NPs on TFR-positive A549 cells. Results showed that TF-HA-CMC-PLGA NPs significantly reduced the survival rate of A549 cells under light irradiation, with better efficacy than HA-CMC-PLGA NPs. Front Pharmacol. 2017 Nov 10;8:815
A549 cells 0.08 μmol/L 15 minutes To evaluate the anti-proliferative and apoptosis-inducing effects of HA-mediated photodynamic therapy on A549 cells. Results showed that HA significantly inhibited A549 cell proliferation and induced apoptosis under light irradiation, accompanied by increased intracellular reactive oxygen species (ROS) generation. Acta Pharm Sin B. 2019 Mar;9(2):279-293

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
BALB/C mice Systemic infection model and oral mucosal infection model Tail vein injection 10 µM Once daily for two weeks Evaluate the inhibitory effect of Hypocrellin A on the pathogenicity of C. albicans SC5314 in mouse infection models, results showed that Hypocrellin A significantly reduced mortality and pathogen numbers in the tongue. Microb Biotechnol. 2021 Mar;14(2):430-443
Male athymic nude mice A549 tumor model Tail vein injection 0.05 mM HA/20g Single dose, lasting for 15 days To evaluate the antitumor efficacy of TF-HA-CMC-PLGA NPs in A549 tumor model. Results showed that TF-HA-CMC-PLGA NPs significantly inhibited tumor growth with a tumor inhibition rate of 63%. Front Pharmacol. 2017 Nov 10;8:815

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

1.83mL

0.37mL

0.18mL

9.15mL

1.83mL

0.91mL

18.30mL

3.66mL

1.83mL

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