Rollinia Mucosa Research Articles

A Novel Application of Mosher's Method to Epimeric Carbinols in Acetogenins; Absolute Configurations of 12-Hydroxy-Bullatacins A and B, New Acetogenins from Rollinia Mucosa

A novel application of Mosher's method to epimeric carbinols is described and demonstrated in eight known Annonaceous acetogenins. The procedure requires the preparation and analysis of either the R or S Mosher esters. As an example, the absolute stereochemistries of 12-hydroxy-bullatacins A and B, two new epimeric acetogenins from Rollinia mucosa, were determined by this new procedure.

Screening for Annonaceous acetogenins in bioactive plant extracts by liquid chromatography/mass spectrometry.

The Annonaceous acetogenins are amenable to analysis by liquid chromatography/mass spectrometry (LC/MS) using the electrospray positive-ion mode. Under conditions of atmospheric pressure in-source collision-induced dissociation (APICID), the acetogenins reproducibly provided characteristic ion patterns and fragment ions. Accordingly, the presence of these biologically interesting acetogenins and other derivatives in plant extracts and chromatographic fractions can be readily detected by analyzing selected ion chromatograms. LC/MS screening of a bioactive crude methanol-soluble fraction of Rollinia mucosa detected the presence of some 40 known acetogenins in this plant extract, in addition to four new acetogenins of diverse structure. This rapid and relatively uncomplicated selected ionization procedure should also prove suitable for the screening of many other structural families of natural products.

Applying Mosher's method to acetogenins bearing vicinal diols. The absolute configurations of muricatetrocin C and rollidecins A and B, new bioactive acetogenins from Rollinia mucosa

Muricatetrocin C (1), rollidecin A (2), and rollidecin B (3), three new bioactive annonaceous acetogenins bearing vicinal diols, were isolated from the leaves of Rollinia mucosa (Annonaceae) using activity-directed fractionation. The total structural elucidations of 1–3, including the absolute stereochemistries of the vicinal diols, were achieved by analyzing their per-Mosher ester derivatives. All three compounds showed potent and selective inhibitory effects against several human cancer cell lines.

Epomusenins A and B, two acetogenins from fruits of Rollinia mucosa

Chromatography of an ethyl acetate extract of the fruits of Rollinia mucosa led to the isolation of two new γ-lactone acetogenins, epomusenins A and B, which are the first examples of the rare C 37-type annonaceous acetogenins having an epoxide and a double bond along the aliphatic chain in place of the usual tetrahydrofuran moeity. The three known acetogenins, rolliniastatin-1, rolliniastatin-2 and squamocin were also isolated. The structures were established by means of one and two dimensional NMR experiments.

Isoquinoline Alkaloids and Lignans from Rollinia mucosa

Romucosine (1), a novel aporphinoid alkaloid possessing a N-(methoxycarbonyl) group, along with 12 known compounds including eight isoquinoline alkaloids, anonaine (2), glaucine, purpureine, liriodenine, oxoglaucine, oxopurpureine, berberine, and tetrahydroberberine, and four lignans, yangambin, magnolin, eudesmin, and membrin, have been isolated and characterized from the fresh unripe fruits of Rollinia mucosa (Annonaceae). The structure of 1 was established by chemical and spectroscopic means.

Rollinecins A and B: two new bioactive annonaceous acetogenins from Rollinia mucosa.

Two new mono-THF ring acetogenins, rollinecins A (1) and B (2), were isolated from the partitioned ethanolic extracts of the leaves of Rollinia mucosa (Annonaceae) by activity-directed fractionation. 1 and 2 are epimeric at the C-14 carbinol stereocenter. Their absolute stereochemical structures were solved by preparing their respective per-Mosher ester derivatives. 1 and 2 showed equivalent and selective in vitro activities against several human solid tumor cell lines.

Isoltion and Structure of Rollinisation 2: A New Cell Growth Inhibitory Acetogenin from Rollinia mucosa

A new cell growth inhibitory acetogenin, designated rolliniastatin 2, has been isolated from seeds of the South American Rollinia mucosa (Annonaceae) and its structure determined. A diastereomeric relationship for rolliniastatin 1, rolliniastatin 2, and asimicin was proposed. The Rollinia genus (Annonaceae) is composed of some 65 species occurring principally from Central America to Argentina. Rollinia, and Uvaria genera have been found to contain members of a new class of biologically active bis- tetrahydrofurans. Our crystal smcture determination of rolliniastatin 12 provided the first definitive smcture in this new series.3-10 By x-ray crystallography, the relative stereochemistry of rolliniastatin 1 was established as 4S*, 15S*, 16S*, 19R*, 20R*, 23S*, 24R*, and 36R*.2 Asimicin, recently isolated from Asimina triloba,8 apparently differs from rolliniastatin 1 in its configuration at one or more of the chiral centers associated with the bis-tetrahydrofuran system. Further detailed fractionation of a hexane extract of Rolliniu mucosa seeds' has led us to uncover companions of rolliniastatin 1, including asimicin and a new diastereomer of rolliniastatin 1, named rolliniastatin 2. Isolation of rolliniastatin 2 flash chromatography on silica gel, high-speed countercurrent distribution (J!ISCCD)11 with a multilayer coil planet centrifuge,lz column chromatography (LiChrom Sia), and finally hplc (semipreparative with Partisil 10 silica gel followed by analytical with Partisil 5 silica gel) with the solvent system hexane - ethyl ether - methanol. With a hplc flow rate of 1.5 m asimicin, 6.57; rolliniastatin 2,

Pallidine and Aporphinoid Alkaloids from Rollinia mucosa

Pallidine and Aporphinoid Alkaloids from Rollinia mucosa

A influência de dois tipos de consórcios de fruteiras na incidência de broca do tronco (Cratosomus sp) na graviola (Annona muricata L.) (*)

O objetivo principal deste trabalho foi estudar a incidência e intensidade de ataque da praga "Broca do tronco" (Cratosomus sp.) na graviola (Annona muricataL.) em um sistema de dois tipos de consórcio de fruteiras. 0 estudo foi realizado na área do projeto "Sistema de Produção Comerciado de Fruteiras", instalado em /977 e se encontra localizado na E.E.S.T. do INPA, Km 41 da BR - 774 no Município de Manaus, foram utiliza das 6 espécies de fruteiras: graviola (Annona muricataL.), côco (Cocos nucíferaL.), pupunha (Bactris gasipaesH.B.K.), caju (Anacardium ocidentaleL.) birlbá (Rollinia mu cosa (Jacq.) Baill e o mapati (Pouroma cecropiazfoliaMart.). Os sistemas comerciados empregados são: Consórcio simples constituído pelas 6 espécies de fruteiras com 16 plantas cada subparcela e o Consórcio misto as 6 espécies de fruteiras foram plantadas al-ternadamente usando o mapati para separar as demais: neste consórcio contém o seguinte número de plantas: 8 graviolas, 8 biribás, 8 cajus, 14 cocos, 14 pupunhas e 98 mapati. 0 delineamento empregado é bloco casualizados com 20 repetições. Avaliaram-se o grau de infestação pelo inseto (Cratosomussp.) e número de plantas atacadas em cada tipo de consórcio, na qual uma planta foi considerada atacada apenas quando apresentou um ata -que ativo, ataques velhos não foram considerados. Os dados sobre o ataque foram coleta dos nos meses de junho/79 a julho/80. Concluiu-se que, apesar da hipótese de que plantas comerciadas sofreriam menor incidência de ataque em plantas de graviola nas parcelas heterogêneas nos primeiros anos do desenvolvimento da plantação. Entretanto, reconhece-se a necessidade de estudos mais especializados sobre o ciclo biológico desta pra ga e sobre diferentes tipos de comércios para fornecer recomendações mais seguras sobre quais são os sistemas de plantio economicamente mais viáveis.