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Related Concept Videos

Antifungal Agents01:15

Antifungal Agents

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Amphotericin B is a broad-spectrum antifungal agent that exploits structural differences between fungal and mammalian cell membranes. Its amphipathic structure—featuring a hydrophobic polyene-lactone ring and a hydrophilic region containing mycosamine and carboxylic acid groups—enables selective binding to ergosterol, a sterol predominantly found in fungal plasma membranes. This selective interaction underlies the drug’s antifungal activity, although weak binding to...
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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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Bioactive Enmein-Type ent-Kaurane Diterpenoids from Isodon phyllostachys.

Jin Yang1,2, Wei-Guang Wang1, Hai-Yan Wu1,2

  • 1State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, People's Republic of China.

Journal of Natural Products
|January 13, 2016
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Summary

This study isolated 32 enmein-type ent-kaurane diterpenoids from Isodon phyllostachys, including 13 new compounds. Some compounds showed significant anticancer and anti-inflammatory activity.

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Area of Science:

  • Natural Products Chemistry
  • Medicinal Chemistry
  • Pharmacology

Background:

  • Isodon species are a rich source of bioactive ent-kaurane diterpenoids.
  • Enmein-type diterpenoids exhibit diverse biological activities.

Purpose of the Study:

  • To isolate and characterize new enmein-type ent-kaurane diterpenoids from Isodon phyllostachys.
  • To evaluate the cytotoxic and anti-inflammatory potential of these compounds.

Main Methods:

  • Isolation and purification of compounds using chromatographic techniques.
  • Structure elucidation via Nuclear Magnetic Resonance (NMR) and High-Resolution Electrospray Ionization Mass Spectrometry (HRESIMS).
  • Determination of absolute and relative configurations using single-crystal X-ray diffraction.

Main Results:

  • Thirty-two enmein-type ent-kaurane diterpenoids were identified, with 13 being novel.
  • Compounds 1 and 2 represent the first reported 3,20:6,20-diepoxyenmein-type ent-kauranoids.
  • Compounds 11, 15, 20, and 21 displayed potent cytotoxic activity against human cancer cell lines (IC50: 1.2–5.0 μM).
  • Compounds 3, 11, 15, 17, 20, 21, 25, and 29 exhibited strong inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 cells (IC50: 0.74–4.93 μM).

Conclusions:

  • The aerial parts of Isodon phyllostachys are a valuable source of structurally diverse enmein-type ent-kaurane diterpenoids.
  • The newly discovered and isolated compounds possess significant anticancer and anti-inflammatory properties, warranting further investigation.