Basic information Description Biochem/physiol Actions Biological Functions Synthesis of Amentoflavone References Safety Related Supplier
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Amentoflavone

Basic information Description Biochem/physiol Actions Biological Functions Synthesis of Amentoflavone References Safety Related Supplier
Amentoflavone Basic information
Amentoflavone Chemical Properties
  • Melting point:>300°C (dec.)
  • Boiling point:910.5±65.0 °C(Predicted)
  • Density 1.656±0.06 g/cm3(Predicted)
  • storage temp. 2-8°C
  • pka6.01±0.40(Predicted)
  • form neat
  • BRN 380244
  • InChIKeyYUSWMAULDXZHPY-UHFFFAOYSA-N
  • CAS DataBase Reference1617-53-4(CAS DataBase Reference)
Safety Information
  • Safety Statements 22-24/25
  • WGK Germany 3
  • 10
  • HS Code 29329990
MSDS
Amentoflavone Usage And Synthesis
  • DescriptionAmentoflavone , a bisapigenin , is one of the best inhibitors in the class of flavonoids , since its active dose is about 0.12uM.
    Amentoflavone (C30H18O10) is a well-known biflavonoid occurring in many natural plants. This polyphenolic compound has been discovered to have some important bioactivities, including anti-inflammation, anti-oxidation, anti-diabetes, and anti-senescence effects on many important reactions in the cardiovascular and central nervous system, etc. Over 120 plants have been found to contain this bioactive component, such as Selaginellaceae, Cupressaceae, Euphorbiaceae, Podocarpaceae, and Calophyllaceae plant families.
    Amentoflavone is a natural product with several associated biological effects.Its ability to block NF-xβ is the key for its anti-inflammatory potential. BETs were identified as NF-xβ promoters, with JQ-1 being highly effective in psoriasis models.
  • Biochem/physiol ActionsBiflavonoid with anti-inflammatory, anti-viral and cancer chemopreventive activity. It inhibits vascularization of tumors by blocking the activity of angiogenic VEGFs. Blocks the induction of COX-2 and up-regulates PPAR-γ. It is a negative modulator of the GABAA receptor at the benzodiazepine binding site.
  • Biological FunctionsAmentoflavone is a biflavonoid originally isolated from Selaginella. It has a wide variety of biological effects including antibacterial, antioxidant, antiviral, antidiabetic, and neuroprotective activities. Amentoflavone has antiviral activity against the influenza A subtypes H1N1 and H3N2, influenza B, and herpes simplex virus 1 (EC50s = 3.1 and 4.3, 0.56, and 17.9 µg/ml, respectively). It has antidiabetic effects such that it dose-dependently increases insulin receptor phosphorylation and activation and inhibits hydrolysis of p-nitrophenyl phosphate (p-NPP) catalyzed by protein tyrosine phosphatase 1B (PTP1B; IC50 = 7.3 µM). Amentoflavone reduces the time mice spend immobile in the forced swim test, a measure of antidepressant efficacy, in a dose-dependent manner.
  • Synthesis of AmentoflavoneAmentoflavone, a biflavanoid, is ubiquitously found in plants such as Calophyllum inophyllum, Eucommia ulmoides, Selaginella doederleinii, Paulownia tomentosa var. tomentosa, Ginkgo biloba, Juglans sigillata, Hypericum perforatum. A wide variety of bioactivities such as anti-viral, anti-inflammatory, anti-tumor, antidepressant, anti-oxidant, anti-microbial, analgesic, antiplasmodial, leishmanicidal, lowering blood lipid and hepatoprotective activities have been reported for amentoflavone and its derivatives. Due to the limited natural abundance, the massive production of amentoflavone is not possible from natural resources. Therefore, total synthesis of amentoflavone would be significant as it will be able to solve the availability issue of amentoflavone. Although the synthesis of amentoflavone through Suzuki-reaction was reported two decades ago, which was to link the flavonyl-8-boronic acid with the 3'-iodoflavone to produce amentoflavone, no synthetic effort has been made ever since to explore an alternative scheme such that the flavonyl3'-boronic acid ester can be linked to the 8-iodoflavone through Suzuki coupling. It would be highly beneficial to the scientific community if this alternative scheme is successful, as this will provide a similar but different route for the synthesis of amentoflavone and other similar biflavonoids, because the preparation of flavonylboronic acid, the key intermediate for the synthesis of biflavonoids, from the corresponding halogenated flavone is sometimes problematic due to steric hindrance or unfavorable electronic effects from neighboring substituting groups in the aromatic ring. Therefore, the goal of this work is to provide an alternative synthetic scheme for the production of amentoflavone and other similar biflavonoids utilizing the coupling of flavonyl-3'-boronic acid ester and 8-iodoflavone, instead of the reported method which was based on the coupling of two different intermediates, the flavonyl-8- boronic acid and the 3'-iodoflavone [10]. Here we describe an efficient synthetic pathway to generate amentoflavone.
    https://www.hilarispublisher.com/open-access/total-synthesis-of-amentoflavone-2161-0444-1000302.pdf
  • ReferencesAmentoflavone (C30H18O10) is a common biflavonoid chemically named as 8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one, which naturally occurs in many plants. It is also considered as an apigenin dimer linked by a C3′-C8′′ covalent bond. This compound was firstly isolated by Okigawa and his colleagues in 1971 from three plants of the Selaginella species (Selaginella tamariscina (Beauv.) Spring, Selaginella nipponica, and Selaginella pachystachys) .
    https://www.mdpi.com/1420-3049/22/2/299/htm
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