+86-28-82633987
Product name: hypocrellin A
Synonym name:
Catalogue No.: BP0754
Cas No.: 77029-83-5
Formula: C30H26O10
Mol Weight: 546.528
Botanical Source: Hypocrella bambusae (Berk. et Br.) Sacc
Physical Description:
Type of Compound: Anthraquinones
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
Description:
Hypocrellin A, an a natural perylene quinine photosensitizers (PSs), can chelate with heavy metal ions, including Au(III) and Pt(IV), to form a 1:2 complex. Hypocrellin A has light-induced antitumor,antifungal and antiviral activities, it also exerts immunomodulatory effects on MHC-restricted presentation of antigen.
References:
Bioorg Med Chem Lett. 2013 Oct 1;23(19):5317-24.
Internal heavy atom effect of Au(III) and Pt(IV) on hypocrellin A for enhanced in vitro photodynamic therapy of cancer.
METHODS AND RESULTS:
Hypocrellin A (HA), an a natural perylene quinine photosensitizers (PSs), can chelate with heavy metal ions, including Au(III) and Pt(IV), to form a 1:2 complex, which exhibits enhanced (1)O2 generation quantum yield through the increased intersystem crossing efficiency mediated by internal heavy atom effect. Besides, the chelate process greatly improved the water solubility of HA.
CONCLUSIONS:
Comparative studies with HA and complexes have demonstrated that the heavy-atom effect on HA molecules enhances the efficiency of in vitro photodynamic (PDT) efficacy.
Nanoscale. 2013 Dec 7;5(23):11910-8.
A new near infrared photosensitizing nanoplatform containing blue-emitting up-conversion nanoparticles and hypocrellin A for photodynamic therapy of cancer cells.
The utilization of up-conversion nanoparticles (UCNPs) for photodynamic therapy (PDT) has gained significant interest due to their unique ability to convert near infrared light to UV/visible light. Previous work mainly focused on the fabrication of green and red emitting UCNPs to load photosensitizers (PSs) for PDT.
METHODS AND RESULTS:
In this work, we firstly developed a new multifunctional nanoplatform combining blue-emitting UCNPs with blue-light excited PS (Hypocrellin A, HA) as a NIR photosensitizing nanoplatform for PDT of cancer cells. Tween 20 coated NaYbF4:Tm, Gd@NaGdF4 UCNPs (Tween 20-UCNPs) with strong blue up-conversion luminescence and good water dispersibility were prepared for use as PS carriers. The blue emission band matched well with the efficient absorption band of HA, thereby facilitating the resonance energy transfer from UCNPs to HA and then activating HA to produce singlet oxygen ((1)O2).
CONCLUSIONS:
The in vitro study showed that these Tween 20-UCNPs@HA complexes could efficiently produce (1)O2 to kill cancer cells under 980 nm NIR excitation. Moreover, these Gd(3+) and Yb(3+) containing nanoparticles also exhibited positive contrast effects in both T1 weighted magnetic resonance imaging (MRI) and computed tomography (CT) imaging, making them become a multifunctional platform for simultaneous PDT and bio-imaging.
Immune Netw. 2011 Dec;11(6):412-5.
Immunomodulatory Effects of Hypocrellin A on MHC-restricted Antigen Processing.
Hypocrellin A has gained much attention in recent years due to its light-induced antitumor, antifungal and antiviral activities.
METHODS AND RESULTS:
Here we report that Hypocrellin A exerts immunomodulatory effects on MHC-restricted presentation of antigen. Hypocrellin A inhibited class II-MHC restricted presentation of exogenous antigen, but not class I MHC-restricted presentation of exogenous antigen, in dendritic cells. Hypocrellin A also inhibited the cytosolic pathway of endogenous antigen presentation. However, Hypocrellin Adid not inhibit the expression of class I and class II MHC molecules on dendritic cells (DCs), the phagocytic activity of DCs, or the H-2K(b)-restricted presentation of a synthetic peptide, SIINFEKL.
CONCLUSIONS:
These results show that Hypocrellin A differentially modulates the MHC-restricted antigen presentation pathways.
HPLC of hypocrellin A
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
148.8200
3.0339
1.8267
.0018
2.0487
2.6921
Low
88.1588
4.3174
No
No
Yes
No
Yes
No
0.9
Yes
No
Yes
No
Hypocrellin A (CAS No.: 77029-83-5) is a natural product derived from fungi of the genus Hypocrellin, attracting attention for its unique photosensitizing activity and multiple pharmacological effects. As a typical photosensitizer for Photodynamic Therapy (PDT), Bakored Mycobacterium methyl has demonstrated significant biological activity in anti-cancer, antibacterial, and antiviral (especially targeting human immunodeficiency virus, HIV). Additionally, recent studies have found its potential to regulate glucose metabolism and fight diabetes, mainly by inhibiting protein kinase C (PKC) and reversing the expression of endothelin (ET-1) induced by high glycemia. Bamboocycinoma methylin also demonstrated strong inhibitory activity against Leishmania (IC50=0.27 μg/ml), indicating its potential application value against parasitic infections. This paper will systematically review the chemical structure and physicochemical properties, sources and extraction methods, pharmacological activity and mechanism of action of Bamboo-red fungus methyl extraction, druggability evaluation, and clinical application prospects, aiming to provide a theoretical foundation and research direction for further drug development and clinical translation.
Bamboo-red fungal methyl compound is a natural product of naphthoquinone, with a molecular formula of C30H22O10 and a molecular weight of 546.5280. Its chemical structure consists of two naphthoquinone units connected by divalent oxygen bridges, forming a polycyclic naphthoquinone derivative backbone with abundant hydroxyl and ketone functional groups. This structure endows Bamboo Red fungus with strong photosensitive properties, enabling monolinear oxygen and other reactive oxygen species to be produced under specific wavelength irradiation, leading to oxidative damage to cells.
In terms of physicochemical properties, the LogP value of Bamboo Red Myces methyl hormone was 3.0339, indicating moderate lipid solubility that facilitates cell membrane penetration, but poor water solubility (about 0.0018 mg/mL), limiting its solubility and bioavailability in the aqueous phase. Its topological pole surface area (TPSA) is 148.82 Ų, suggesting high molecular polarity that may affect transmembrane absorption. The blood-brain barrier has low permeability, suggesting its limited distribution in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiac toxicity in Methyl Cyperus xylomycosis. The Ames test result was 0.9, indicating a low genotoxicity risk and meeting safety requirements.
Bamboo Red Fungus Methyl mainly comes from fungi of the genus Bamboo-red Fungus, especially species such as Hypocrella bambusae and Shiraia bambusicola. These fungi grow on the dead branches or leaves of bamboo plants and are parasitic or saprophytic fungi. The natural yield of Bamboo Red Mycetes methyl is relatively low, limiting its large-scale application, making the development of efficient extraction and purification methods crucial.
Traditional extraction methods usually use organic solvent extraction methods, such as ethanol, methanol, or ethyl acetate, combined with ultrasound-assisted extraction or Soxhlet extraction techniques to improve extraction efficiency. The extract was purified through multiple steps such as silica gel column chromatography and reversed-phase high-performance liquid chromatography (RP-HPLC) to obtain high-purity bamboo-red mycetes methyl extract. In recent years, microbial fermentation technology and genetic engineering methods have been introduced to improve the yield and production stability of Bamboo Red Myces methyl Methyl. In addition, chemical synthesis and semi-synthesis methods are also being explored, but due to complex structures, longer synthesis routes, and higher costs, industrial production has not yet been achieved.
Bamboo Red Fungus methylin, as a protein kinase C (PKC) inhibitor, has shown potential value in the prevention and treatment of diabetes and its complications. Under high-sugar conditions, the expression of endothelin (ET-1) is abnormally elevated, leading to vasoconstriction, inflammatory responses, and endothelial dysfunction. Bamboo Red Mycete methyl inhibits PKC activity, reverses high-sugar induced ET-1 expression, improves endothelial function, alleviates diabetes-related vascular lesions, and demonstrates good antidiabetic activity.
Bamboo Red Acetomycetes Methyl has shown significant anticancer effects across various tumor models, especially in the field of breast cancer. Its anti-cancer mechanism involves multiple signaling pathways and molecular targets, including:
Additionally, bamboo red fungus methyl extract acts as a photosensitizer, generating reactive oxygen species in photodynamic therapy through light stimulation, inducing oxidative damage and apoptosis in tumor cells, thereby enhancing treatment outcomes.
Bamboo Red Myces methyl hormone exhibits inhibitory effects on various bacteria, especially effective against Gram-positive bacteria and some Gram-negative bacteria. Its antibacterial mechanism mainly relies on reactive oxygen species generated by photodynamic therapy that damage bacterial cell membranes and nucleic acids.
In terms of antiviral activity, Baoximycetes methyl hormone demonstrates significant phototoxic activity against human immunodeficiency virus (HIV). Through PDT, Bamboo-red Myceta's methyl can disrupt the viral envelope and inhibit viral replication, demonstrating its potential as an anti-HIV photosensitizer.
Leishmania infection is a major parasitic disease worldwide. Bamboo-red mycelium methyl hormone exhibits strong inhibitory effects on Leishmania parasite, with an IC50 of only 0.27 μg/ml. This activity offers new ideas for developing novel antiparasitic drugs, especially in the context of increasingly severe drug resistance.
The multiple pharmacological activities of Bamboo Red Mycete methyl are attributed to its complex mechanism of action and multi-target regulatory capability. Its core mechanisms include:
PKC inhibition: By directly inhibiting protein kinase C (PKC) activity, it regulates cellular signaling, reverses pathological states induced by high glucose, and improves endothelial function and diabetes-related complications.
Photosensitive activity: Under specific wavelength light irradiation, Bamboo-red fungus methyl hormone excites the production of singlet oxygen and free radicals, inducing cellular oxidative stress and destroying the structure and function of tumor cells and pathogenic microorganisms.
Signaling pathway regulation: Regulates key molecules such as AMPK, STAT3, and BCL2, affecting cell metabolism, proliferation, and apoptosis, and inhibiting tumor growth and drug resistance.
Multidrug resistance protein inhibition: Inhibits the functions of ABCB1 and ABCG2, reverses multidrug resistance in tumor cells, and improves the efficacy of chemotherapy drugs.
Matrix degrading enzyme inhibition: inhibits MMP2 activity, reducing tumor cell invasion and metastasis.
Immune regulation: By modulating immune-related kinases such as LCK, it influences the function of immune cells in the tumor microenvironment, enhancing anti-tumor immune responses.
The drug-producing properties of Bamboo-red fungus methyl extract are challenging, mainly reflected in its extremely low water solubility (0.0018 mg/mL), which limits the bioavailability of oral and intravenous administration. Its LogP value was 3.0339, indicating good lipid solubility and facilitating membrane penetration, but high polarity (TPSA=148.82 Ų) may affect its transmembrane absorption and distribution.
The low permeability of the blood-brain barrier suggests limited efficacy in the central nervous system, but this also reduces the risk of CNS toxicity. hERG channel inhibition is negative, indicating a low risk of cardiotoxicity and good safety. The Ames test results are close to negative, with a low risk of genotoxicity.
Pharmacokinetics, the metabolic pathway of Bamboo-red Myceta's methyl in vivo is not yet fully elucidated, but its phenolic hydroxyl and quinone groups may undergo redox reactions and binding metabolism through hepatic enzyme systems. Due to poor water solubility, drug carrier systems (such as liposomes and nanoparticles) have been extensively studied to improve their distribution and stability in vivo.
As a versatile natural product, Bamboo Red Mycetes methyl acid has broad clinical application potential:
Applications in photodynamic therapy: As a photosensitizer, Bamboo-red Myscopium methyl Methyl Acid demonstrates excellent results in tumor treatment (such as breast cancer and skin cancer) and viral infection therapy. In the future, targeted delivery systems and new light source technologies can be combined to enhance treatment selectivity and safety.
Development of antidiabetic drugs: By regulating PKC and ET-1 expression, Bamboo Erythromycetes methyl is expected to become a novel therapeutic agent for diabetes and its vascular complications. Further in vivo pharmacodynamic evaluation and preclinical safety studies are needed.
Antiparasitic drugs: The highly effective inhibitory activity against Leishmania offers new approaches for treating parasitic diseases, especially as resistance becomes increasingly severe.
Antibacterial and antiviral drugs: The photosensitive bactericidal and antiviral properties of Bamboohongmycetes methyl provide new strategies for treating infectious diseases, especially for refractory viruses such as HIV.
Future research should focus on solving drug delivery and bioavailability issues of Bamboo-red Mycobacterium methylin, optimizing dosage formulation design, conducting systematic pharmacokinetic and toxicological evaluations, and conducting multicenter clinical trials to verify its safety and efficacy. Moreover, combining modern molecular biology and medicinal chemistry techniques to explore its structural modification and derivative development will help enhance its clinical application value.
Bamboo Red Fungus methyl acid, as a natural product with multiple pharmacological activities, shows broad application prospects in multiple fields such as anti-cancer, anti-diabetes, antibacterial, antiviral, and antiparasitic properties, thanks to its unique chemical structure and photosensitive properties. Although there are certain limitations in druggability, modern drug formulation technologies and molecular modification methods are expected to overcome these obstacles and achieve clinical translation. Future in-depth exploration of its mechanism of action, optimization of drug delivery systems, and clinical research will promote Bamboo-Red Mycobacterium methyl Methyl to become an important model for natural product drug development, providing new solutions for the treatment of related diseases.
Shenshuai
Wenjing
Hedandan
