Triterpenes from the exudate of Gardenia urvillei

• Published in: Phytochemistry (Oxford) Vol. 122; pp. 193 - 202
• Main Authors: Mai, Hoang Linh, Grellier, Philippe, Prost, Elise, Lemoine, Pascale, Poullain, Cyril, Dumontet, Vincent, Deguin, Brigitte, Vo, Thi Bach Hue, Michel, Sylvie, Grougnet, Raphaël
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.02.2016; Elsevier
• Subjects: Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Biochemistry & Molecular Biology; Chemical Sciences; Cycloartane; Cytotoxicity; Dammarane; Dammaranes; Drug Screening Assays, Antitumor; Gardenia - chemistry; Gardenia urvillei; Life Sciences; Life Sciences & Biomedicine; Microbiology and Parasitology; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Exudates - chemistry; Plant Exudates - isolation & purification; Plant Exudates - pharmacology; Plant Sciences; Plasmodium; Rubiaceae; Science & Technology; Seco-cycloartane; Structure-Activity Relationship; Triterpenes - chemistry; Triterpenes - isolation & purification; Triterpenes - pharmacology; Trypanosoma; Plasmodium; Gardenia urvillei; Trypanosoma; Rubiaceae; Cycloartane; Seco-cycloartane; Dammarane; Cytotoxicity; GLYCOSIDES; MANAGEMENT; LEAVES; CYCLOARTANE TRITERPENES; AUBRYI; TUBIFERA; ANTI-HIV-1 CONSTITUENTS; GUM RESIN; CYTOTOXIC 3,4-SECO-CYCLOARTANE TRITERPENES; MEDICINAL-PLANTS
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2015.11.001

Cycloartanes, secocycloartanes and dammaranes have been isolated from the bud exudate of Gardenia urvillei. Some of these triterpenes have shown cytotoxicity and anti-parasite activity. [Display omitted] •Nineteen triterpenes isolated from the bud exudate of Gardenia urvillei.•Seven original compounds, including cycloartanes, seco-cycloartanes and dammaranes.•Structures determined by NMR, MS, IR, chemical correlation and X-ray diffraction.•Evaluation of cytotoxicity and anti-parasite activity (Plasmodium, Trypanosoma). A cycloartane gardurvilleic acid, three 3,4-seco-cycloartanes securvienol, secodienurvilleic acid, securvitriol, a 3,4;9,10-seco-cycloartane gardheptlactone, two dammaranes urvilone, urvilol, along with eight known cycloartanes and 3,4-seco-cycloartanes and four known dammaranes have been isolated from the bud exudate of Gardenia urvillei, an endemic tree to the New Caledonian dry forest. Two other dammarane derivatives have been obtained by semisynthesis. The structures of the original compounds were determined by spectroscopic methods and chemical correlations. In association with previously published data, the description of oxidized side-chains in position 17 are now available for two couples of diastereoisomers. Evaluation of anti-parasite activity and cytotoxicity has shown noticeable results for some of the isolated triterpenes.