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Flavonoids from Andrographis viscosula.

Yerra Koteswara Rao1, Amooru Gangaiah Damu, Alahari Janardhan Rao

  • 1Natural Products Division, Department of Chemistry, Sri Venkateswara University, Tirupati, India.

Chemical & Pharmaceutical Bulletin
|December 4, 2003
PubMed
Summary
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Researchers identified new and known flavones from Andrographis viscosula. These 2'-oxygenated flavonoids are unique to the Andrographis genus, serving as key chemotaxonomic markers in the Acanthaceae family.

Area of Science:

  • Phytochemistry
  • Natural Product Chemistry
  • Chemotaxonomy

Background:

  • The Andrographis genus, part of the Acanthaceae family, is known for its diverse phytochemical constituents.
  • Flavonoids are a significant class of secondary metabolites with various biological activities.
  • Understanding the chemical diversity within plant species is crucial for chemotaxonomic studies.

Purpose of the Study:

  • To conduct a comprehensive phytochemical investigation of the whole plant of Andrographis viscosula.
  • To isolate and characterize new and known flavonoid compounds.
  • To evaluate the chemotaxonomic significance of 2 extquotesingle-oxygenated flavonoids within the Andrographis genus.

Main Methods:

  • Phytochemical analysis of Andrographis viscosula using various extraction and isolation techniques.

Related Experiment Videos

  • Structure elucidation of isolated compounds employing extensive physical and spectral methods, including 2D Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Comparative analysis of isolated flavonoids with known compounds to identify novel structures.

    • Main Results:

    • Isolation of three new 2 extquotesingle-oxygenated flavonoids: (2R)-5-hydroxy-7,2 extquotesingle,3 extquotesingle-trimethoxyflavanone (1), 7,2 extquotesingle,5 extquotesingle-trimethoxyflavone (2), and 5,7,2 extquotesingle,3 extquotesingle-tetramethoxyflavone (3).
    • Identification of eight known flavones: 5,7,2 extquotesingle-trimethoxyflavone (4), 5,7,2 extquotesingle,4 extquotesingle,5 extquotesingle-pentamethoxyflavone (5), echioidinin (6), 5,2 extquotesingle,6 extquotesingle-trihydroxy-7-methoxyflavone (7), 5-hydroxy-7,2 extquotesingle-dimethoxyflavone (8), echioidin (9), echioidinin 5-O-glucoside (10), and 5,2 extquotesingle,6 extquotesingle-trihydroxy-7-methoxyflavone 2 extquotesingle-O-glucoside (11).
    • Confirmation of structures through detailed spectroscopic analyses, including 2D NMR.

    Conclusions:

    • The phytochemical investigation of Andrographis viscosula yielded a total of eleven compounds, including three novel 2 extquotesingle-oxygenated flavonoids.
    • The exclusive presence of 2 extquotesingle-oxygenated flavonoids in Andrographis species suggests their potential as specific chemotaxonomic markers for this genus within the Acanthaceae family.
    • This study contributes to the understanding of flavonoid diversity and chemotaxonomic relationships in the Acanthaceae.