51419-48-8

Usage

Uses

Used in Pharmaceutical Applications:
Hydnocarpin is used as an antibacterial agent for its historical use in the treatment of leprosy, demonstrating its effectiveness against certain bacterial strains.
Used in Cancer Therapy Development:
Hydnocarpin is used as a multidrug resistance modulator for its potential role in the development of cancer therapies, enhancing the efficacy of existing treatments and overcoming resistance in cancer cells.
Used in Antimicrobial Applications:
Hydnocarpin is used as an antimicrobial agent for its broad-spectrum activity against various bacteria, offering a natural alternative for combating bacterial infections.
Used in Drug Delivery Systems:
Hydnocarpin is used as a component in drug delivery systems to improve the bioavailability and therapeutic outcomes of other drugs, particularly in the context of cancer treatment, by modulating multidrug resistance.

InChI:InChI=1/C25H20O9/c1-31-20-7-13(2-4-15(20)28)25-23(11-26)33-21-6-12(3-5-18(21)34-25)19-10-17(30)24-16(29)8-14(27)9-22(24)32-19/h2-10,23,25-29H,11H2,1H3

Upstream product

• 871249-25-1 23-O-acetylsilibinin 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 458-35-5 coniferal alcohol 
• 802918-57-6 silybin 

Relevant academic research and scientific papers

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

Various Mitsunobu conditions were investigated for a series of flavonolignans (silybin A, silybin B, isosilybin A, and silychristin A) to achieve either selective esterification in position C-23 or dehydration in a one-pot reaction yielding the biological

Hydnocarpin-Type Flavonolignans: Semisynthesis and Inhibitory Effects on Staphylococcus aureus Biofilm Formation

A new, efficient, and general semisynthesis of hydnocarpin-type flavonolignans was developed and optimized, enabling gram-scale production of hydnocarpin D (2). Moreover, the syntheses of optically pure hydnocarpin isomers [(10R,11R)-hydnocarpin (1a), (10R,11R)-hydnocarpin D (2a), and (10S,11S)-hydnocarpin D (2b)], as well as the synthesis of isohydnocarpin (8), were achieved for the first time utilizing this new method. The synthesis is based on the two-step transformation of the readily available flavonolignans from milk thistle (Silybum marianum), accessible by isolation from the commercial extract silymarin. The first step relies on the regioselective formylation of the C-3 hydroxy group of the dihydroflavonol-type precursor using the Vilsmeier-Haack reagent, followed by formic acid elimination by triethylamine in the second step. The synthesized compounds were effective inhibitors of Staphylococcus aureus biofilm formation, with (10S,11S)-hydnocarpin D (2b) being the most potent inhibitor. Furthermore, the effect of glucose on biofilm formation was tested, and glucose decreased the biofilm inhibitory activity of 2b. Moreover, 2b increased the susceptibility of Staph. aureus to enrofloxacin. (Chemical Equation Presented).

Synthesis and structures of regioisomeric hydnocarpin-type flavonolignans

Flavonolignans represent natural compounds whose biosynthesis presumes a radical coupling of a ring B catecholic flavonoid with a molecule of coniferyl alcohol or an analogue. Many natural flavonolignans can exist as regioisomers, depending on how the coupled coniferyl alcohol moiety orients to the flavonoid. These regioisomers are often difficult to separate and have virtually identical NMR spectra. Structural assignments for some have changed with time or have been given without proof. We here report syntheses of both regioisomers of the flavonolignan hydnocarpin and one isomer of a plant isolate previously known as 5'-methoxyhydnocarpin. This isomer, here renamed 5'-methoxyhydnocarpin-D, was recently shown to be a potent inhibitor of a Staphylococcus aureus multidrug resistant efflux pump.