Andirolides H–P from the flower of andiroba (Carapa guianensis, Meliaceae)

• Published in: Tetrahedron Vol. 68; no. 18; pp. 3669 - 3677
• Main Authors: Tanaka, Yuji, Sakamoto, Asami, Inoue, Takanobu, Yamada, Takeshi, Kikuchi, Takashi, Kajimoto, Tetsuya, Muraoka, Osamu, Sato, Akira, Wataya, Yusuke, Kim, Hye-Sook, Tanaka, Reiko
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 06.05.2012; Elsevier
• Subjects: Alicyclic compounds, terpenoids, prostaglandins, steroids; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antiparasitic agents; Biological and medical sciences; Carapa guianensis; Chemistry; Chemistry, Organic; Dichroism; Exact sciences and technology; Flowers; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; In vitro testing; Limonoids; Medical sciences; Meliaceae; Nuclear magnetic resonance; Organic chemistry; Pharmacology. Drug treatments; Physical Sciences; Plasmodium falciparum; Preparations and properties; Science & Technology; Spectra; Steroids; Terpenoids; Tetrahedrons; ANTIMALARIAL ACTIVITY; LIMONOIDS; WEST-AFRICAN TIMBERS; EXTRACTIVES; Steroid; Protozoa; Antimalarial; Terpenoid; Apicomplexa; Flower; Molecular structure; Lactone; NMR spectrometry; Oxygen heterocycle; In vitro; Meliaceae; Plasmodium falciparum; Oil; Dicotyledones; Circular dichroism spectrometry; Angiospermae; Absolute configuration; Plant origin; Triterpene; Isolation; Spermatophyta
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.12.076

Three new gedunins, an andirobin, three mexicanolides, and two phragmalin-type limonoids named andirolides H (1), I (2), J (3), K (4), L (5), M (6), N (7), O (8), and P (9) were isolated from an oil of the flower of Carapa guianensis Aublet (Meliaceae). Their structures including the absolute configurations were determined by means of the NMR and CD spectra as well as FABMS. Andirolide H (1) showed antimalarial activity against Plasmodium falciparum in vitro. [Display omitted]