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Jerry L. Mclaughlin - One of the best experts on this subject based on the ideXlab platform.
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isolation of new bioactive annonaceous acetogenins from Rollinia mucosa guided by liquid chromatography mass spectrometry
Bioorganic & Medicinal Chemistry, 1997Co-Authors: Dawei Zhou, Guoen Shi, Neil J Lewis, Jerry L. MclaughlinAbstract:Reversed-phase high-performance liquid chromatography (RP-HPLC) fractionation, monitored by liquid chromatography/electrospray mass spectrometry (LC/ESI-MS), led to the isolation of two new bioactive annonaceous acetogenins, rollidecin C (1) and rollidecin D (2), from the bioactive aqueous methanol fraction of the leaves of Rollinia mucosa (Annonaceae). The structures were confirmed by analyses of the 1H and 13C NMR data. In addition, a known adjacent bis-tetrahydrofuran (THF) acetogenin, desacetyluvaricin (3), was isolated from this plant for the first time utilizing the LC/ESI-MS monitoring approach. Compound 1 exhibited selective cytotoxicity toward the colon tumor cell line (HT-29), while 2 showed only borderline cytotoxicity in a panel of six human tumor cell lines.
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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
Natural Product Letters, 1997Co-Authors: Guoen Shi, John M. Macdougal, Xiao-xi Liu, Jerry L. MclaughlinAbstract:Abstract 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.
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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
Bioorganic & Medicinal Chemistry, 1996Co-Authors: Guoen Shi, John M. Macdougal, Karl V Wood, Lu Zeng, Jerry L. MclaughlinAbstract:Abstract 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.
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rollinecins a and b two new bioactive annonaceous acetogenins from Rollinia mucosa
Journal of Natural Products, 1996Co-Authors: Guoen Shi, Jerry L. Mclaughlin, John M. MacdougalAbstract: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.
Guoen Shi - One of the best experts on this subject based on the ideXlab platform.
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isolation of new bioactive annonaceous acetogenins from Rollinia mucosa guided by liquid chromatography mass spectrometry
Bioorganic & Medicinal Chemistry, 1997Co-Authors: Dawei Zhou, Guoen Shi, Neil J Lewis, Jerry L. MclaughlinAbstract:Reversed-phase high-performance liquid chromatography (RP-HPLC) fractionation, monitored by liquid chromatography/electrospray mass spectrometry (LC/ESI-MS), led to the isolation of two new bioactive annonaceous acetogenins, rollidecin C (1) and rollidecin D (2), from the bioactive aqueous methanol fraction of the leaves of Rollinia mucosa (Annonaceae). The structures were confirmed by analyses of the 1H and 13C NMR data. In addition, a known adjacent bis-tetrahydrofuran (THF) acetogenin, desacetyluvaricin (3), was isolated from this plant for the first time utilizing the LC/ESI-MS monitoring approach. Compound 1 exhibited selective cytotoxicity toward the colon tumor cell line (HT-29), while 2 showed only borderline cytotoxicity in a panel of six human tumor cell lines.
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Bioactive annonaceous acetogenins from Rollinia mucosa
Phytochemistry, 1997Co-Authors: Guoen Shi, John M. Macdougal, Jerry L. MclaughlintAbstract:Two new bioactive Annonaceous acetogenins, rollitacin (1) and rollinacin (2), along with one known acetogenin, javoricin, were isolated from the ethanolic extract of the leaves of Rollinia mucosa. Compounds 1 and 2 exhibited selective inhibitory effects among six human solid tumour cell lines. The structural elucidations of 1 and 2 were achieved by various spectroscopic analyses and chemical derivatizations.
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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
Natural Product Letters, 1997Co-Authors: Guoen Shi, John M. Macdougal, Xiao-xi Liu, Jerry L. MclaughlinAbstract:Abstract 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.
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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
Bioorganic & Medicinal Chemistry, 1996Co-Authors: Guoen Shi, John M. Macdougal, Karl V Wood, Lu Zeng, Jerry L. MclaughlinAbstract:Abstract 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.
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rollinecins a and b two new bioactive annonaceous acetogenins from Rollinia mucosa
Journal of Natural Products, 1996Co-Authors: Guoen Shi, Jerry L. Mclaughlin, John M. MacdougalAbstract: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.
Solange Faria Lua Figueiredo - One of the best experts on this subject based on the ideXlab platform.
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Micropropagation of Rollinia mucosa (JACQ.) baill
In Vitro Cellular & Developmental Biology - Plant, 2001Co-Authors: Solange Faria Lua Figueiredo, Norma Albarello, Vera Regina Campos VianaAbstract:A protocol for in vitro propagation of Rollinia mucosa , an important medicinal plant, was developed. The presence of 500 mg l^−1 polyvinylpyrrolidone (PVP) during explant excision was important to avoid browning. Axillary buds, adventitious buds, and shoot cluster proliferation were achieved from epicotyl and hypocotyl explants from nursery-grown seedlings. The highest direct organogenesis percentage from hypocotyl explants was obtained upon culture of explants on Murashige and Skoog medium supplemented with 2.2 μ M benzyladenine (BA) plus 2.32 μ M kinetin. Epicotyl explants display highest regeneration frequency on a medium containing 8.8 μ M BA and 0.54 μ M naphthaleneacetic acid. Gibberellic acid was necessary for shoot elongation. Root induction was observed when shoots were pretreated with activated charcoal for 7 d in the dark before culture on Woody Plant Medium supplemented with 49.21 μ M indolebutyric acid for 10 d. Root development was observed when 20 g l^−1 sucrose was used. Rooted plantlets were acclimatized and grown in the greenhouse.
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Rollinia mucosa cell suspension cultures: Establishment and growth conditions
Plant Cell Tissue and Organ Culture, 2000Co-Authors: Solange Faria Lua Figueiredo, Cláudia Simões, Norma Albarello, Vera Regina Campos VianaAbstract:Different types and concentrations of plant growth regulators were tested in order to obtain the best callus and cell suspension culture growth conditions of Rollinia mucosa (Jacq.) Baill. (Annonaceae). Picloram was shown to be the most efficient for induction and production of friable calluses, independent of the concentration used. Cellular morphology and viability, fresh and dry weights, pH and medium sugar concentration were determined for cell suspension cultures. Dissimilation curves were used for the characterization of the growth of cell suspension cultures. Picloram provided the most rapid growth and produced the highest biomass, with little variation in morphology (differentiated cells). It also provided the highest dissimilation, when compared with cell suspension cultures maintained in media with 2,4-D or NAA + BA + GA_3. Stable cell suspension cultures can be established in MS medium supplemented with 20.8 μM picloram.
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lignans from leaves seedlings and micropropagated plants of Rollinia mucosa jacq baill annonaceae
Plant Cell Tissue and Organ Culture, 1999Co-Authors: Solange Faria Lua Figueiredo, Cláudia Simões, Norma Albarello, Vera Regina Campos Viana, Luiz C Trugo, Maria Auxiliadora Coelho Kaplan, William Robert KrulAbstract:Rollinia mucosa produces furofuranic lignans (magnolin, epiyangambin, yangambin) that are antagonists of platelet-activating factor (PAF). The biosynthetic capacity and the potential for the accumulation of furofuranic lignans, including epieudesmin, of the plants cultured both in vivo and in vitro conditions were evaluated. The production and the pattern of lignans accumulated were dependent on the origin of the plant material and the plant organ. The major accumulation of lignans was observed in leaves. In the mature leaves of in vivo grown seedlings magnolin and yangambin predominated, in contrast to leaves from in vitro propagated plants that presented epiyangambin as the major lignan.
Fang Rong Chang - One of the best experts on this subject based on the ideXlab platform.
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a novel constituent from Rollinia mucosa rollicosin and a new approach to develop annonaceous acetogenins as potential antitumor agents
Journal of Natural Products, 2003Co-Authors: Chih Chuang Liaw, Fang Rong ChangAbstract:Rollicosin (1), a new Annonaceous acetogenin, was isolated from the unripe fruits of Rollinia mucosa. Rollicosin (1) is the first compound of this type to contain lactone moieties on both sides of the aliphatic chain and to lack either tetrahydrofuran or tetrahydropyran rings. Its structure was determined on the basis of spectroscopic analyses. This compound may serve as a new prototype molecule to develop Annonaceous acetogenins as potential antitumor agents.
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a new propentdyopent derivative rollipyrrole from Rollinia mucosa baill
ChemInform, 2002Co-Authors: Reen Yen Kuo, Fang Rong ChangAbstract:Abstract Rollipyrrole 1 , a novel pyrromethenone derivative was isolated from the leaves of Rollinia mucosa in the continuing research into Formosan annonaceous plants. This type of compound was isolated from plants for the first time and the structure of 1 was elucidated mainly on the basis of 1D and 2D NMR spectroscopic data.
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antiplatelet activity of n methoxycarbonyl aporphines from Rollinia mucosa
Phytochemistry, 2001Co-Authors: Reen Yen Kuo, Fang Rong Chang, Chung Yi Chen, Cheming Teng, Hsin Fu YenAbstract:Bioassay-directed fractionation of the stems of Rollinia mucosa led to the isolation of new N-methoxycarbonyl aporphine alkaloids, romucosine A (1), romucosine B (2), romucosine C (3), and romucosine D (4), along with the known alkaloid, N-methoxylcarbonyl-nornuciferine (5). Alkaloids 1 and 4 exhibited significant inhibition of collagen, arachidonic acid, and platelet activating factor-induced platelet aggregation, and alkaloid 3 also showed an inhibitory effect on arachidonic acid induced platelet aggregation.
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new annonaceous acetogenins from Rollinia mucosa
Journal of Natural Products, 1999Co-Authors: Chih Chuang Liaw, Fang Rong Chang, Yuan Yng Chen, Hui Fen ChiuAbstract:Four new compounds, a mixture of 20,23-cis-2,4-trans-bullatalicinone (1) and 20,23-cis-2,4-cis-bullatalicinone (2), rollimusin (3), and rolliacocin (4), along with eight known acetogenins, were isolated from an ethyl acetate extract of the unripe fruits of Rollinia mucosa. The structures and stereochemistry of 1-4 were determined on the basis of spectral data and chemical evidence.
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Isoquinoline alkaloids and lignans from Rollinia mucosa
Journal of Natural Products, 1996Co-Authors: Yuan Yng Chen, Fang Rong ChangAbstract: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.
Hsin Fu Yen - One of the best experts on this subject based on the ideXlab platform.
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antiplatelet activity of n methoxycarbonyl aporphines from Rollinia mucosa
Phytochemistry, 2001Co-Authors: Reen Yen Kuo, Fang Rong Chang, Chung Yi Chen, Cheming Teng, Hsin Fu YenAbstract:Bioassay-directed fractionation of the stems of Rollinia mucosa led to the isolation of new N-methoxycarbonyl aporphine alkaloids, romucosine A (1), romucosine B (2), romucosine C (3), and romucosine D (4), along with the known alkaloid, N-methoxylcarbonyl-nornuciferine (5). Alkaloids 1 and 4 exhibited significant inhibition of collagen, arachidonic acid, and platelet activating factor-induced platelet aggregation, and alkaloid 3 also showed an inhibitory effect on arachidonic acid induced platelet aggregation.
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Epomusenins A and B, two acetogenins from fruits of Rollinia mucosa☆
Phytochemistry, 1996Co-Authors: Yuan Yng Chen, Fang Rong Chang, Hsin Fu YenAbstract:Abstract 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 C37-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.
