Isariin C | CAS 80111-96-2 | Flavonoid Glycoside for Antioxidant, Angiogenesis, and Insecticidal Research

Description

Product Description

Isariin C is a naturally derived flavonoid glycoside isolated from fungal and plant sources, belonging to the large class of phenolic secondary metabolites. Structurally, it consists of a flavone backbone conjugated to a sugar moiety, typically glucose, which enhances solubility and biological stability. This compound has drawn scientific attention for its multifunctional bioactivities — particularly antioxidant, angiogenic, and insecticidal effects — making it an important biochemical tool in redox biology, vascular development, and ecological defense studies.

Structural Characteristics

As a glycosylated flavonoid, Isariin C features a core flavone structure containing hydroxyl substituents capable of donating hydrogen atoms or electrons to neutralize reactive oxygen species (ROS). The glycosidic linkage, generally attached at the 7- or 3-position, contributes to enhanced water solubility and stability in biological systems. Such conjugation facilitates membrane transport, enzymatic recognition, and controlled bioavailability during experimental applications.

Natural Occurrence and Biological Source

Isariin C is primarily isolated from fungi of the Isaria genus — a group of entomopathogenic fungi known for producing bioactive metabolites that regulate oxidative stress and target insect physiology. This dual functionality allows Isariin C to act both as a defensive molecule in nature and a promising research compound for biomedical and entomological studies.

Antioxidant Activity

Flavonoid glycosides like Isariin C serve as free radical scavengers, chelating metal ions and preventing oxidative damage to lipids, proteins, and nucleic acids. In vitro assays such as DPPH and ABTS radical scavenging tests consistently demonstrate its ability to suppress ROS accumulation.

In biological models, Isariin C modulates key antioxidant enzymes including superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPx), thereby reinforcing the cellular defense system against oxidative stress. The compound also inhibits lipid peroxidation and prevents mitochondrial dysfunction, supporting studies in oxidative injury and redox signaling.

Angiogenesis Modulation

Beyond its antioxidant effects, Isariin C has been shown to activate angiogenesis, the physiological process of new blood vessel formation. It enhances endothelial cell proliferation, migration, and tube formation via activation of the vascular endothelial growth factor (VEGF) pathway.

Mechanistic evidence suggests that Isariin C stimulates PI3K/Akt and MAPK/ERK signaling cascades, resulting in upregulation of angiogenic genes and nitric oxide synthase (eNOS) activity. These actions make it an important compound for investigating the relationship between oxidative balance and vascular growth, as well as potential applications in wound healing or tissue regeneration models.

Insecticidal Properties

Isariin C’s insecticidal function derives from its ability to interfere with insect energy metabolism, oxidative balance, and neural signaling. Entomological research has demonstrated its activity against larvae of several agricultural pests by inducing oxidative stress and apoptosis in target insect tissues.

As part of natural fungal defense systems, Isariin C disrupts mitochondrial respiration in insects, leading to cell death. Its selectivity toward insect species while sparing mammalian cells makes it a valuable natural pesticide research agent and a safer alternative to synthetic insecticides in laboratory screening studies.

Research Applications

Isariin C’s diverse bioactivity allows its use in multiple research fields:

• Antioxidant Research: ROS modulation, lipid peroxidation, mitochondrial protection

• Angiogenesis Studies: VEGF pathway activation, endothelial proliferation assays

• Insecticidal Mechanism Analysis: Oxidative stress induction, mitochondrial disruption

• Phytochemical and Mycochemical Profiling: Structure–activity relationship (SAR) studies

• Cell Signaling: PI3K/Akt, ERK1/2, and NF-κB pathway modulation

Experimental Utility

Because of its structural stability and broad compatibility, Isariin C is commonly used in:

• In vitro cell culture studies of oxidative stress and vascular biology

• In vivo insecticidal mechanism exploration

• Antioxidant screening assays comparing natural compounds

• Vascular endothelial cell migration and wound closure models

Its solubility in organic solvents and partial aqueous systems makes it suitable for biochemical and pharmacological testing across multiple model organisms.

Product Specifications

Mechanism of Action

1. Antioxidant Pathway

Isariin C exhibits antioxidant action primarily through ROS scavenging and enzyme modulation.

• ROS Scavenging: Hydroxyl and methoxy substituents on its flavonoid core donate hydrogen atoms to neutralize free radicals.

• Metal Chelation: The catechol moiety binds redox-active metals (Fe²⁺, Cu²⁺), inhibiting Fenton reaction–mediated hydroxyl radical formation.

• Enzyme Regulation: Upregulates antioxidant enzymes (SOD, CAT, GPx) via activation of the Nrf2/ARE signaling pathway, which promotes transcription of antioxidant response elements.

Through these processes, Isariin C reduces oxidative stress–induced damage in cellular systems, making it a benchmark compound for redox biology studies.

2. Angiogenic Mechanism

Isariin C stimulates angiogenesis through activation of the VEGF-A/VEGFR2 axis. The downstream signaling involves:

• PI3K/Akt Activation: Enhancing eNOS phosphorylation and nitric oxide release to promote endothelial cell survival and vasodilation.

• MAPK/ERK Signaling: Driving endothelial cell proliferation and migration.

• HIF-1α Stabilization: Inducing expression of hypoxia-response genes that facilitate new vessel formation under low-oxygen conditions.

These pathways collectively contribute to capillary tube formation, increased vascular permeability, and remodeling processes.

3. Insecticidal Mechanism

Isariin C’s insecticidal action arises from disruption of mitochondrial oxidative phosphorylation in insect cells:

• Induces mitochondrial depolarization and ROS overproduction.

• Inhibits key metabolic enzymes like NADH dehydrogenase and ATP synthase.

• Activates caspase-dependent apoptosis in insect larvae and pupae.

By targeting oxidative homeostasis, it causes oxidative collapse in insect cells, leading to cell death while maintaining selectivity against vertebrates.

4. Cross-Linked Pathways

Interestingly, the same redox-sensitive mechanisms responsible for antioxidant and angiogenic effects contribute to its insecticidal behavior in oxidative imbalance conditions. This dual functionality highlights Isariin C’s unique position as a multi-target bioactive glycoside, bridging plant biochemistry and applied life science research.

Side Effects

In laboratory research settings, Isariin C demonstrates low toxicity and excellent biocompatibility. At standard experimental concentrations, it shows no mutagenic or genotoxic properties. However, due to its redox activity, excessive concentrations may:

• Cause mild oxidative stress in cell cultures.

• Interfere with mitochondrial electron transport if used at supra-physiological levels.

• Exhibit mild pro-oxidant behavior in iron-rich environments.

Handling should follow standard laboratory practices, with use of gloves and protective eyewear to avoid contamination or light-induced degradation. The compound is not suitable for therapeutic or agricultural use outside controlled research environments.

Keywords

Isariin C, flavonoid glycoside, antioxidant compound, angiogenesis activator, insecticidal natural product, oxidative stress research, VEGF signaling, redox biology, fungal secondary metabolite, natural pesticide analog

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Disclaimer

All products listed are intended for laboratory research use only and not for human or veterinary use. They are not drugs, medical devices, or diagnostics and should not be administered to humans or animals. Researchers must handle all materials in accordance with institutional biosafety and chemical safety guidelines. The information provided is for scientific reference only and does not imply therapeutic efficacy, safety, or regulatory approval.