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Cat. No.: HY-N21536

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Angustone A

Name: Angustone A
Brand: MedChemExpress
SKU: HY-N21536
Availability: PreOrder

(Synonyms: 2'-Hydroxylupalbigenin)

Angustone A (2'-Hydroxylupalbigenin) is a diisoprenylated isoflavone with insect feeding inhibitory activity and moderate antifungal activity. Angustone A can be converted into various phenolic metabolites by Aspergillus flavus through modification of the isoprenyl side chains at the C-6 and C-3' positions. Angustone A can be used in studies on antifungal properties of natural products, insect feeding behavior, fungal biotransformation, and anticancer activity.

For research use only. We do not sell to patients.

CAS No.: 90686-13-8
Formula: C₂₅H₂₆O₆
Molecular Weight:422.47

Storage:

Please store the product under the recommended conditions in the Certificate of Analysis.

Angustone A Chemical Structure

CAS No.: 90686-13-8

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Biological Activity
- Description
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
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References
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Biological Activity

Description

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	7.1 μM Compound: 19	Cytotoxicity against human A549 cells assessed as reduction in cell viability after 24 hrs by MTS assay Cytotoxicity against human A549 cells assessed as reduction in cell viability after 24 hrs by MTS assay	[PMID: 26841168]
HepG2	IC₅₀	1.1 μM Compound: 19	Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 24 hrs by MTS assay Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 24 hrs by MTS assay	[PMID: 26841168]
MCF7	IC₅₀	6 μM Compound: 19	Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 24 hrs by MTS assay Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 24 hrs by MTS assay	[PMID: 26841168]
SW480	IC₅₀	6.4 μM Compound: 19	Cytotoxicity against human SW480 cells assessed as reduction in cell viability after 24 hrs by MTS assay Cytotoxicity against human SW480 cells assessed as reduction in cell viability after 24 hrs by MTS assay	[PMID: 26841168]

In Vitro

OthersFungal InfectionAnti-cancer

Others

Angustone A (2'-Hydroxylupalbigenin) (50 μg/mL; 3 days) undergoes biotransformation by Aspergillus flavus AHU 7049 into 10 structurally distinct isoflavonoid metabolites, among which AF-d-1 (lupinisoflavone F) has the highest content (10.44 mg of product obtained from 50 mg of substrate)^[1].

Fungal Infection

Angustone A (compound Ⅵ) (40-100 μg/mL; 24 h) gradually inhibits the growth of Colletotrichum gloeosporioides spore juveniles, with an ED₉₅ of > 100 μg/mL against both C. gloeosporioides and Cladosporium cladosporioides^[2].

Anti-cancer

Others

Angustone A (200 μg/mL; 24 h) significantly reduces the feeding response of third-instar larvae of Costelytra zealandica and Heteronychus arator, with feeding responses of 35.9% and 56.8%, respectively^[2].

Anti-cancer

Angustone A exhibits an IC₅₀ of 1.1-7.1 μM and inhibits the growth of four cancer cell lines^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Angustone A (2'-Hydroxylupalbigenin) (2-200 μg/mL; incorporated into feeding disk; 24-hour exposure) significantly reduces the feeding behavior of third-instar larvae of Costelytra zealandica at the concentration of 200 μg/mL, with a 35.9% decrease in feeding response rate^[2].
Angustone A (200 μg/mL; mixed into feeding dishes; 24 h exposure) significantly reduces the feeding behavior of third-instar Heteronychus arator larvae, with a 56.8% decrease in feeding response rate at the concentration of 200 μg/mL^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Field-collected third-instar larvae^[2]
Dosage:

2 μg/mL; 20 μg/mL; 100 μg/mL; 200 μg/mL
Administration:

Incorporated into feeding disk; 24-hour exposure
Result:

Resulted in a 93.9% feeding response at 2 μg/mL.
Resulted in an 85.9% feeding response at 20 μg/mL.
Resulted in a 76.2% feeding response at 100 μg/mL.
Resulted in a 35.9% feeding response at 200 μg/mL, which represented a significant reduction in feeding.

Animal Model:

Field-collected third-instar larvae^[2]
Dosage:

200 μg/mL
Administration:

Incorporated into feeding disk; 24-hour exposure
Result:

Resulted in a 56.8% feeding response, which represented a significant reduction in feeding.

Chemical Information

CAS No. 90686-13-8
Molecular Weight 422.47
Formula C₂₅H₂₆O₆
SMILES

O=C1C(C2=C(O)C(C/C=C(C)\C)=C(O)C=C2)=COC3=CC(O)=C(C/C=C(C)\C)C(O)=C13
Synonyms

2'-Hydroxylupalbigenin
Structure Classification
- Flavonoids
- Flavones
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Nakahara S, Tahara S, Mizutani J, Ingham JL. Transformation of the Diprenylated Isoflavone 2'-Hydroxylupalbigenin by Aspergillus flavus. Agricultural and Biological Chemistry. 1986;50(4):863-873.

[2]. Lane GA, et al. Isoflavonoids as insect feeding deterrents and antifungal components from root ofLupinus angustifolius. Journal of chemical ecology. 1987 Apr;13(4):771-83. [Content Brief]

[3]. Fan H, Xuan J, Zhang K, Jiang J. Anticancer component identification from the extract of Dysosma versipellis and Glycyrrhiza uralensis based on support vector regression and mean impact value. Analytical Methods. 2018.

Calculators

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Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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100 mg

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