Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae)

• Published in: European journal of medicinal chemistry Vol. 93; pp. 93 - 100
• Main Authors: Mai, Linh H., Chabot, Guy G., Grellier, Philippe, Quentin, Lionel, Dumontet, Vincent, Poulain, Cyril, Espindola, Laila S., Michel, Sylvie, Vo, Hue T.B., Deguin, Brigitte, Grougnet, Raphaël
• Format: Journal Article
• Language: English
• Published: France Elsevier Masson SAS 26-03-2015; Elsevier
• Subjects: Angiogenesis Inhibitors - chemical synthesis; Angiogenesis Inhibitors - chemistry; Angiogenesis Inhibitors - isolation & purification; Angiogenesis Inhibitors - pharmacology; Animals; Antileishmanial; Antiparasitic Agents - chemical synthesis; Antiparasitic Agents - chemistry; Antiparasitic Agents - isolation & purification; Antiparasitic Agents - pharmacology; Antiplasmodial; Antivascular agents; Cancer; Cell Line, Tumor; Cell Survival - drug effects; Chemical Sciences; Drug Design; Endothelial cells; Flavonoids; Flavonoids - chemical synthesis; Flavonoids - chemistry; Flavonoids - isolation & purification; Flavonoids - pharmacology; Flowers - chemistry; Gardenia - chemistry; Humans; Leishmania - drug effects; Life Sciences; Molecular Structure; New Caledonia; Plant Extracts - chemistry; Plasmodium falciparum - drug effects; Structure-Activity Relationship; Trypanocidal; Trypanosoma brucei gambiense - drug effects; New Caledonia; Antiplasmodial; Flavonoids; Trypanocidal; Antileishmanial; Antivascular agents; Endothelial cells; IN-VITRO; VASCULAR DISRUPTING AGENTS; VIVO; MICROTUBULES; DOCKING; POLYMERIZATION; TRITERPENES; TUBULIN; BINDING; DERIVATIVES
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2015.01.012

A series of 16 flavonoids were isolated and prepared from bud exudate of Gardenia urvillei and Gardenia oudiepe, endemic to New Caledonia. Most of them are rare polymethoxylated flavones. Some of these compounds showed noticeable activity against Leishmania (Leishmania) amazonensis, Plasmodium falciparum and Trypanosoma brucei gambiense, in addition to tubulin polymerization inhibition at low micromolar concentration. We also provide a full set of NMR data as some of the flavones were incompletely described.
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•16 flavones were isolated and semi-synthetized from New Caledonian Gardenia.•They were evaluated for antiangiogenic/antivascular and antiparasitic activity.•Some of them demonstrated strong and specific activity.•They may be considered as model for future development and pharmacomodulation.