Isolation and structure of rolliniastatin 1 from the South American tree Rolliniamucosa

Abstract

in primitive medical practices of Indonesia and the West Indies as a treatment for tumors, has been investigated employing the seeds from a South American variety and the murine P388 lymphocytic leukemia (PS) for bioassay. The principal antineoplastic constituent (PS, 28% life extension, at 0.25 mg/kg and EDso4.5 X kg/mL) was found to be a new bis-tetrahydrofuran designated rolliniastatin 1. Structural elucidation of rolliniastatin 1 was accomplished by a combination of high resolution nuclear magnetic resonance (300 MHz), mass spectral, and X-ray crystal structure techniques. 1433 (1987).Utilisant les graines d'une variCtC sud-amiricaine de la plante et la murine P388 de IeucCmie lymphocitaire (PS) pour des bioessais, on a CtudiC les propriCtCs de la Rollinin tnucosa (Annonaceae), qui est connue dans les pratiques mCdicales primitives de l'lndonksie et des Antilles pour le traitement des tumeurs. On a trouvC que le principal constituant actif (PS, augmentation de vie de 28%, i 0,25 mg/kg et EDs0 de 4,s X lop5 kg/mL) est un nouveau bis-tktrahydrofuranne que I'on a appelC rolliniastatine 1. On a dCtermink la structure de la rolliniastatine 1 en combinant les techniques de la rCsonance magnkt~que nucICaire i haute rCsolution (300 MHz), du spectre de masse et de la diffraction des rayons-)< par des cristaux uniques.[Traduit par la revue]The Annonaceae (ca. 2,100 species) is composed of shrubs and trees found mainly in tropical regions. The genus Rollinia generally occurs in Central and South America, and R. mucosa (Jacq.) Vaill, also known as Annona mucosa (Jacq.), has been used for the primitive medical treatment of tumors in the West Indies and in Indonesia (2). To assess the potential of this plant in respect to potentially useful antineoplastic components, seeds of Rollirzia mucosa were collected in French Guiana in 1979. The lipophilic extract of these seeds showed activity in the P388 lymphocytic leukemia system, and fractionation of this extract was guided by bioassay using the murine P388 system in vitro.Extraction of Rollinla mucosa seed (600g) with hexane afforded 136 g of oily extract from which rolliniastatin 1 was isolated by a series of chromatographic steps. Steric exclusion chromatography was followed by gradient elution chromatography on silica gel with hexane -ethyl acetate.

Anxiolytic-like and sedative actions ofRollinia mucosa: Possible involvement of the GABA/benzodiazepine receptor complex

“…The fruit is regarded as a refrigerant, analeptic, and anti-scorbutic, while the powdered seeds are said to be a remedy for enterocolitis (Morton, 1987). Chemical investigations of this species reported the presence of acetogenins with antineoplastic and cytotoxic activities in seeds and leaves (Pettit et al, 1987;Shi et al, 1997). In addition, we reported that the furafuranic lignans, (+)-epieudesmine and (+)-epimagnolin, and the linear C 31 -ketone palmitone (16-hentriacontanone), were the principal constituents of the hexane extract of leaves of R. mucosa (Estrada-Reyes et al, 2002).…”

Recent Advancements in Stereoselective Olefin Metathesis Using Ruthenium Catalysts

“…Grubbs and coworkers utilized 9 in this transformation, as 9 is highly Z-selective and promotes the formation of anti-diols [173]. Many stereodefined anti-diols containing various functionalities could be prepared using this method (Table 22) Tetrahydrofuran (THF) diols are found in a wide variety of natural products [174][175][176][177]. A convenient method for the formation of THF diols is through the oxidative cyclization of 1,5-dienes to form 2,5-disubstituted THF diols.…”

“…Tetrahydrofuran (THF) diols are found in a wide variety of natural products [174][175][176][177]. A convenient method for the formation of THF diols is through the oxidative cyclization of 1,5-dienes to form 2,5-disubstituted THF diols.…”

Efeito de diferentes meios nutritivos e fitorreguladores visando à otimização da calogênese de Annona mucosa (Jacq.)

“…(Waechter et al, 1999), larvicida contra Aedes aegypti (Dominguez-Martinez et al, 2003), atividade moduladora da resistência bacteriana (Costa et al, 2008), bactericida e antifúngica (Wiart, 2007). Entretanto, destaca-se o potencial antineoplásico dessas substâncias, sendo promissoras no tratamento de cânceres devido aos efeitos citotóxicos observados em linhagens tumorais e carcinomas diversos (Pettit et al, 1988;Shi et al, 1996;Shi et al, 1997;Gu et al, 1997, Kim & Park, 2002.…”