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Jerry L Mclaughlin - One of the best experts on this subject based on the ideXlab platform.
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asimitrin and 4 hydroxytrilobin new bioactive annonaceous acetogenins from the seeds of Asimina triloba possessing a bis tetrahydrofuran ring
Journal of Natural Products, 2005Co-Authors: Eun Joo Jung, Jerry L MclaughlinAbstract:Bioactivity-directed fractionation of the seeds of Asimina triloba resulted in the isolation of asimitrin (1) and 4-hydroxytrilobin (2). Compound 1 represents an adjacent ring-hydroxylated bis-tetrahydrofuran (THF) acetogenin. Compound 2 has an adjacent bis-THF ring with two flanking hydroxyl groups and a α,β-unsaturated γ-lactone with a 4-hydroxyl group. Compounds 1 and 2 showed cytotoxic selectivity, with 100−10 000 times the potency of adriamycin against prostate adenocarcinoma (PC-3) and colon adenocarcinoma (HT-29) cell lines.
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Asimitrin and 4-hydroxytrilobin, new bioactive annonaceous acetogenins from the seeds of Asimina triloba possessing a bis-tetrahydrofuran ring.
Journal of Natural Products, 2005Co-Authors: Eun Jung Kim, Eun Joo Jung, Mi-hee Woo, Kyung Mi Suh, Dal Hwan Kim, Chang Seob Seo, Jong Keun Son, Jerry L MclaughlinAbstract:Bioactivity-directed fractionation of the seeds of Asimina triloba resulted in the isolation of asimitrin (1) and 4-hydroxytrilobin (2). Compound 1 represents an adjacent ring-hydroxylated bis-tetrahydrofuran (THF) acetogenin. Compound 2 has an adjacent bis-THF ring with two flanking hydroxyl groups and a alpha,beta-unsaturated gamma-lactone with a 4-hydroxyl group. Compounds 1 and 2 showed cytotoxic selectivity, with 100-10 000 times the potency of adriamycin against prostate adenocarcinoma (PC-3) and colon adenocarcinoma (HT-29) cell lines.
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additional bioactive annonaceous acetogenins from Asimina triloba annonaceae
Bioorganic & Medicinal Chemistry, 1997Co-Authors: Kan He, Jinfeng Chao, Gengxian Zhao, Lu Zeng, Jerry L MclaughlinAbstract:Abstract trilobalicin ( 1 ), a new nonadjacent bis-THF ring annonaceous acetogenin, 2,4- cis - ( 2 ) and 2,4- trans -trilobacinone ( 3 ), the ketolactones of trilobacin, an adjacent bis-THF ring acetogenin, were isolated from the stem bark of Asimina triloba (L.) Dunal (Annonaceae). Their structures were established based on chemical and spectral evidence. The relative stereochemistry of 1 was determined as trans/threo/threo/trans/erythro from C-10 to C-22 by comparisons of NMR data with those of model compounds. Compound 1 is the first example of a nonadjacent bis-THF acetogenin being isolated from the title species and represents a new type of these compounds. Bioactivities of these new structures against brine shrimp larvae and six human solid tumor cell lines were determined, and cytotoxic selectivities were shown for the lung (A-549) and breast (MCF-7) cell lines with up to a million times the potency of adriamycin.
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three new adjacent bis tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba
Journal of Natural Products, 1996Co-Authors: Kan He, Gengxian Zhao, Jon T Schwedler, Karl V Wood, Qing Ye, Lu Zeng, Jerry L MclaughlinAbstract:Three new adjacent bis-tetrahydrofuran ring Annonaceous acetogenins with four hydroxy groups, bullatetrocin (1), 10-hydroxyasimicin (2), and 10-hydroxytrilobacin (3), were isolated by activity-directed fractionation from the stem bark of Asimina triloba. Their structures were established on the basis of chemical and spectral evidence. The absolute stereochemistry at the C-10 hydroxy position was determined by converting 2 and 3 to their ketolactone isomers, 2,4-cis/trans 10-hydroxyasimicinones and 2,4-cis/trans 10-hydroxytrilobacinones, respectively. The bioactivities of the new compounds against brine shrimp larvae and six human solid-tumor cell lines are reported, and structure−activity relationships between trihydroxylated and tetrahydroxylated acetogenins are discussed. In addition to 1−3, gigantetrocin A, 2,4-cis/trans-gigantetrocin A-ones, annonacin, and annonacin A were also isolated for the first time from this species.
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2 4 cis asimicinone and 2 4 trans asimicinone two novel bioactive ketolactone acetogenins from Asimina triloba annonaceae
Natural Toxins, 1996Co-Authors: Gengxian Zhao, Jinfeng Chao, Lu Zeng, Jerry L MclaughlinAbstract:: Two novel bioactive ketolactone Annonaceous acetogenins, (2,4-cis)-asimicinone (1) and (2,4-trans)-asimicinone (2), have been isolated from Asimina triloba (Annonaceae) by bioactivity directed fractionation. The separation of these two epimeric compounds was achieved by HPLC methods using a Si gel normal phase column eluted with acetone in hexane gradients. The assignments of cis or trans stereochemistry of the ketolactone moieties were made on the bases of 1H-1H COSY and NOESY experiments. 1 and 2 showed selective cytotoxicities against A-549 (human lung cancer) and MCF-7 (human breast cancer) cell lines with ED50 values as low as < 10(-7) micrograms/ml with 2 being the more active isomer.
Paul Feeny - One of the best experts on this subject based on the ideXlab platform.
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oviposition stimulant for the zebra swallowtail butterfly eurytides marcellus from the foliage of pawpaw Asimina triloba
Chemoecology, 1998Co-Authors: Meena Haribal, Paul FeenyAbstract:We have isolated a caffeoylcyclohexane-1-carboxylic acid derivative, 3-caffeoyl-muco-quinic acid (3-CmQA), as a contact oviposition stimulant for the zebra swallowtail butterfly, Eruytides marcellus (Papilionidae), from the foliage of its primary host plant, Asimina triloba (Annonaceae). This compound alone was as active in stimulating oviposition by females as were the parent ethanolic plant extract and the host plant itself. Other tested isomers of 3-CmQA, including 5-caffeoylquinic acid (5-CQA or trans-chlorogenic acid), were inactive. We found, however, that experienced female butterflies responded strongly to host volatiles, which enhanced landing rates and hence oviposition.¶ This is the first report of an oviposition stimulant for a swallowtail butterfly of the tribe Graphiini. We found 3-CmQA to be the major caffeoylcyclohexane-1-carboxylic acid isomer in plants of the genus Asimina. These plants lack appreciable amounts of 5-CQA, which has been shown previously to be one of the oviposition stimulants for certain Rutaceae- or Apiaceae-feeding swallowtails of the related tribe Papilionini.¶ Our findings, along with earlier results from the tribes Troidini and Papilionini, suggest that responses by swallowtails to hydroxycinnamic acid derivatives as oviposition cues date back at least to the ancestor of the subfamily Papilioninae.
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oviposition stimulant for the zebra swallowtail butterfly eurytides marcellus from the foliage of pawpaw Asimina triloba
Chemoecology, 1998Co-Authors: Meena Haribal, Paul FeenyAbstract:We have isolated a caffeoylcyclohexane-1-carboxylic acid derivative, 3-caffeoyl-muco-quinic acid (3-CmQA), as a contact oviposition stimulant for the zebra swallowtail butterfly, Eruytides marcellus (Papilionidae), from the foliage of its primary host plant, Asimina triloba (Annonaceae). This compound alone was as active in stimulating oviposition by females as were the parent ethanolic plant extract and the host plant itself. Other tested isomers of 3-CmQA, including 5-caffeoylquinic acid (5-CQA or trans-chlorogenic acid), were inactive. We found, however, that experienced female butterflies responded strongly to host volatiles, which enhanced landing rates and hence oviposition.¶ This is the first report of an oviposition stimulant for a swallowtail butterfly of the tribe Graphiini. We found 3-CmQA to be the major caffeoylcyclohexane-1-carboxylic acid isomer in plants of the genus Asimina. These plants lack appreciable amounts of 5-CQA, which has been shown previously to be one of the oviposition stimulants for certain Rutaceae- or Apiaceae-feeding swallowtails of the related tribe Papilionini.¶ Our findings, along with earlier results from the tribes Troidini and Papilionini, suggest that responses by swallowtails to hydroxycinnamic acid derivatives as oviposition cues date back at least to the ancestor of the subfamily Papilioninae.
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a caffeoylcyclohexane 1 carboxylic acid derivative from Asimina triloba
Phytochemistry, 1998Co-Authors: Meena Haribal, Paul Feeny, Cathy C LesterAbstract:Abstract Three caffeoyl derivatives of 1,3,4,5-tetrahydroxycyclohexane 1-carboxylic acid, one of them an oviposition stimulant for the zebra swallowtail butterfly, Eurytides marcellus , were isolated from Asimina triloba . The structure of the active isomer, 3-caffeoyl- muco -quinic acid, was determined by extensive NMR studies.
Meena Haribal - One of the best experts on this subject based on the ideXlab platform.
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oviposition stimulant for the zebra swallowtail butterfly eurytides marcellus from the foliage of pawpaw Asimina triloba
Chemoecology, 1998Co-Authors: Meena Haribal, Paul FeenyAbstract:We have isolated a caffeoylcyclohexane-1-carboxylic acid derivative, 3-caffeoyl-muco-quinic acid (3-CmQA), as a contact oviposition stimulant for the zebra swallowtail butterfly, Eruytides marcellus (Papilionidae), from the foliage of its primary host plant, Asimina triloba (Annonaceae). This compound alone was as active in stimulating oviposition by females as were the parent ethanolic plant extract and the host plant itself. Other tested isomers of 3-CmQA, including 5-caffeoylquinic acid (5-CQA or trans-chlorogenic acid), were inactive. We found, however, that experienced female butterflies responded strongly to host volatiles, which enhanced landing rates and hence oviposition.¶ This is the first report of an oviposition stimulant for a swallowtail butterfly of the tribe Graphiini. We found 3-CmQA to be the major caffeoylcyclohexane-1-carboxylic acid isomer in plants of the genus Asimina. These plants lack appreciable amounts of 5-CQA, which has been shown previously to be one of the oviposition stimulants for certain Rutaceae- or Apiaceae-feeding swallowtails of the related tribe Papilionini.¶ Our findings, along with earlier results from the tribes Troidini and Papilionini, suggest that responses by swallowtails to hydroxycinnamic acid derivatives as oviposition cues date back at least to the ancestor of the subfamily Papilioninae.
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oviposition stimulant for the zebra swallowtail butterfly eurytides marcellus from the foliage of pawpaw Asimina triloba
Chemoecology, 1998Co-Authors: Meena Haribal, Paul FeenyAbstract:We have isolated a caffeoylcyclohexane-1-carboxylic acid derivative, 3-caffeoyl-muco-quinic acid (3-CmQA), as a contact oviposition stimulant for the zebra swallowtail butterfly, Eruytides marcellus (Papilionidae), from the foliage of its primary host plant, Asimina triloba (Annonaceae). This compound alone was as active in stimulating oviposition by females as were the parent ethanolic plant extract and the host plant itself. Other tested isomers of 3-CmQA, including 5-caffeoylquinic acid (5-CQA or trans-chlorogenic acid), were inactive. We found, however, that experienced female butterflies responded strongly to host volatiles, which enhanced landing rates and hence oviposition.¶ This is the first report of an oviposition stimulant for a swallowtail butterfly of the tribe Graphiini. We found 3-CmQA to be the major caffeoylcyclohexane-1-carboxylic acid isomer in plants of the genus Asimina. These plants lack appreciable amounts of 5-CQA, which has been shown previously to be one of the oviposition stimulants for certain Rutaceae- or Apiaceae-feeding swallowtails of the related tribe Papilionini.¶ Our findings, along with earlier results from the tribes Troidini and Papilionini, suggest that responses by swallowtails to hydroxycinnamic acid derivatives as oviposition cues date back at least to the ancestor of the subfamily Papilioninae.
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a caffeoylcyclohexane 1 carboxylic acid derivative from Asimina triloba
Phytochemistry, 1998Co-Authors: Meena Haribal, Paul Feeny, Cathy C LesterAbstract:Abstract Three caffeoyl derivatives of 1,3,4,5-tetrahydroxycyclohexane 1-carboxylic acid, one of them an oviposition stimulant for the zebra swallowtail butterfly, Eurytides marcellus , were isolated from Asimina triloba . The structure of the active isomer, 3-caffeoyl- muco -quinic acid, was determined by extensive NMR studies.
Gengxian Zhao - One of the best experts on this subject based on the ideXlab platform.
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additional bioactive annonaceous acetogenins from Asimina triloba annonaceae
Bioorganic & Medicinal Chemistry, 1997Co-Authors: Kan He, Jinfeng Chao, Gengxian Zhao, Lu Zeng, Jerry L MclaughlinAbstract:Abstract trilobalicin ( 1 ), a new nonadjacent bis-THF ring annonaceous acetogenin, 2,4- cis - ( 2 ) and 2,4- trans -trilobacinone ( 3 ), the ketolactones of trilobacin, an adjacent bis-THF ring acetogenin, were isolated from the stem bark of Asimina triloba (L.) Dunal (Annonaceae). Their structures were established based on chemical and spectral evidence. The relative stereochemistry of 1 was determined as trans/threo/threo/trans/erythro from C-10 to C-22 by comparisons of NMR data with those of model compounds. Compound 1 is the first example of a nonadjacent bis-THF acetogenin being isolated from the title species and represents a new type of these compounds. Bioactivities of these new structures against brine shrimp larvae and six human solid tumor cell lines were determined, and cytotoxic selectivities were shown for the lung (A-549) and breast (MCF-7) cell lines with up to a million times the potency of adriamycin.
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three new adjacent bis tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba
Journal of Natural Products, 1996Co-Authors: Kan He, Gengxian Zhao, Jon T Schwedler, Karl V Wood, Qing Ye, Lu Zeng, Jerry L MclaughlinAbstract:Three new adjacent bis-tetrahydrofuran ring Annonaceous acetogenins with four hydroxy groups, bullatetrocin (1), 10-hydroxyasimicin (2), and 10-hydroxytrilobacin (3), were isolated by activity-directed fractionation from the stem bark of Asimina triloba. Their structures were established on the basis of chemical and spectral evidence. The absolute stereochemistry at the C-10 hydroxy position was determined by converting 2 and 3 to their ketolactone isomers, 2,4-cis/trans 10-hydroxyasimicinones and 2,4-cis/trans 10-hydroxytrilobacinones, respectively. The bioactivities of the new compounds against brine shrimp larvae and six human solid-tumor cell lines are reported, and structure−activity relationships between trihydroxylated and tetrahydroxylated acetogenins are discussed. In addition to 1−3, gigantetrocin A, 2,4-cis/trans-gigantetrocin A-ones, annonacin, and annonacin A were also isolated for the first time from this species.
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2 4 cis asimicinone and 2 4 trans asimicinone two novel bioactive ketolactone acetogenins from Asimina triloba annonaceae
Natural Toxins, 1996Co-Authors: Gengxian Zhao, Jinfeng Chao, Lu Zeng, Jerry L MclaughlinAbstract:: Two novel bioactive ketolactone Annonaceous acetogenins, (2,4-cis)-asimicinone (1) and (2,4-trans)-asimicinone (2), have been isolated from Asimina triloba (Annonaceae) by bioactivity directed fractionation. The separation of these two epimeric compounds was achieved by HPLC methods using a Si gel normal phase column eluted with acetone in hexane gradients. The assignments of cis or trans stereochemistry of the ketolactone moieties were made on the bases of 1H-1H COSY and NOESY experiments. 1 and 2 showed selective cytotoxicities against A-549 (human lung cancer) and MCF-7 (human breast cancer) cell lines with ED50 values as low as < 10(-7) micrograms/ml with 2 being the more active isomer.
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the absolute configuration of adjacent bis thf acetogenins and asiminocin a novel highly potent asimicin isomer from Asimina triloba
Bioorganic & Medicinal Chemistry, 1996Co-Authors: Gengxian Zhao, Jinfeng Chao, Matthew J Rieser, Lu Zeng, Jerry L MclaughlinAbstract:Abstract A novel acetogenin, asiminocin (1), was isolated by activity-directed fractionation from the stem bark of the paw paw tree, Asimina triloba . By spectral and chemical methods, 1 was identified as (30 S )-hydroxy-4-deoxyasimicin. The absolute configuration of 1, along with those of previously reported acetogenins asimin, Asiminacin, bullatin, (30 S )-bullanin, and (30 R ) bullanin, was determined by Mosher ester methodology. Compound 1 was highly inhibitory to three human solid tumor cell lines with over a billion times the potency of adriamycin.
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the absolute configuration of trilobacin and trilobin a novel highly potent acetogenin from the stem bark of Asimina triloba annonaceae
Tetrahedron, 1995Co-Authors: Gengxian Zhao, Zhe-ming Gu, Jinfeng Chao, John F Kozlowski, Karl V Wood, Lu Zeng, J L MclaughlinAbstract:Abstract trilobacin ( 1 ) is the only previously reported Annonaceous acetogenin with the erythro relative configuration between the adjacent bis-tetrahydrofuran (THF) rings. The relative configuration in the adjacent bis-THF moiety of 1 was corrected to threo/trans/erythro/cis/threo from C-15 to C-24, and the absolute configuration was determined as 4 R , 15 R , 16 R , 19 R , 20 S , 23 R , 24 R and 36 S by advanced Mosher ester methodology and the COSY and NOESY spectral analyses of its 4,24-diacetate ( 1a ). Further investigation of the EtOH extract of the stem bark of the paw paw tree, Asimina triloba , monitoring for bioactivity by brine shrimp lethality, led to a novel acetogenin, trilobin ( 2 ). Spectral and chemical methods identified 2 as a 4-deoxy-10-hydroxy isomer of 1 . The absolute configuration of 2 was determined as 10 R , 15 R , 16 R , 19 R , 20 S , 23 R , 24 R , and 36 S by analyses of its Mosher ester derivatives. 2 was selectively cytotoxic among three human solid tumor cell lines with over a billion times the potency of adriamycin.
J L Mclaughlin - One of the best experts on this subject based on the ideXlab platform.
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asitrilobins a and b cytotoxic mono thf annonaceous acetogenins from the seeds of Asimina triloba
Phytochemistry, 1999Co-Authors: J L MclaughlinAbstract:Abstract The seeds of Asimina triloba have yielded two novel cytotoxic mono-tetrahydrofuran (THF) Annonaceous acetogenins, asitrilobins A (1) and B (2). In addition, annonacin, asimin and Asiminacin, which are known, and annomontacin and xylomaticin, which are known but are new in this species, were obtained. Compounds 1 and 2 have a relative stereochemical relationship of erythro/cis/threo across the mono-THF ring with its two flanking hydroxyls and they, thus, represent a new type of acetogenin. Their structures were established on the basis of chemical and spectral evidence. 1 and 2 showed potent bioactivities in the brine shrimp lethality test (BST) and among six human solid tumor cell lines with notable selectivity for the pancreatic cell line (MIA PaCa-2) at ten to one-hundred times the potency of adriamycin.
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the absolute configuration of trilobacin and trilobin a novel highly potent acetogenin from the stem bark of Asimina triloba annonaceae
Tetrahedron, 1995Co-Authors: Gengxian Zhao, Zhe-ming Gu, Jinfeng Chao, John F Kozlowski, Karl V Wood, Lu Zeng, J L MclaughlinAbstract:Abstract trilobacin ( 1 ) is the only previously reported Annonaceous acetogenin with the erythro relative configuration between the adjacent bis-tetrahydrofuran (THF) rings. The relative configuration in the adjacent bis-THF moiety of 1 was corrected to threo/trans/erythro/cis/threo from C-15 to C-24, and the absolute configuration was determined as 4 R , 15 R , 16 R , 19 R , 20 S , 23 R , 24 R and 36 S by advanced Mosher ester methodology and the COSY and NOESY spectral analyses of its 4,24-diacetate ( 1a ). Further investigation of the EtOH extract of the stem bark of the paw paw tree, Asimina triloba , monitoring for bioactivity by brine shrimp lethality, led to a novel acetogenin, trilobin ( 2 ). Spectral and chemical methods identified 2 as a 4-deoxy-10-hydroxy isomer of 1 . The absolute configuration of 2 was determined as 10 R , 15 R , 16 R , 19 R , 20 S , 23 R , 24 R , and 36 S by analyses of its Mosher ester derivatives. 2 was selectively cytotoxic among three human solid tumor cell lines with over a billion times the potency of adriamycin.
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biologically active acetogenins from stem bark of Asimina triloba
Phytochemistry, 1993Co-Authors: Gengxian Zhao, Matthew J Rieser, Laura R Miesbauer, David L. Smith, J L MclaughlinAbstract:Abstract In continuing our research with cytotoxic and pesticidal components from the stem bark of the North American paw paw, Asimina triloba , the novel cytotoxic monotetrahydrofuran Annonaceous acetogenins, cis - and trans -annonacin-A-one, cis - and trans -gigantetrocinone and cis -isoannonacin, in addition to the known compounds, trans -isoannonacin and squamolone, have been identified. Brine shrimp lethality testing was used to direct the fractionation. The structures were elucidated by spectral analysis and/or chemical synthesis. These acetogenins have potent cytotoxicities against the human tumour cell lines of A-549 (lung carcinoma), MCF-7 (breast carcinoma) and HT-29 (colon adenocarcinoma).
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inhibition of respiration at site i by asimicin an insecticidal acetogenin of the pawpaw Asimina triloba annonaceae
Pesticide Biochemistry and Physiology, 1993Co-Authors: M.a. Lewis, Bernard J. R. Philogène, J K Rupprecht, John T. Arnason, J L MclaughlinAbstract:Abstract The insecticidal mode of action of the acetogenin asimicin and a standardized acetogenin extract, FO20, isolated from Asimina triloba Dunal was investigated. Dietary FO20 reduced the rate of oxygen consumption by fourth instar Ostrinia nubilalis as measured with a constant volume manometer. Further examination of the respiratory effect of both FO20 and asimicin was carried out on mitochondria isolated from the midguts of fifth instar O. nubilalis and in which O 2 was measured polarographically. The results of these studies indicate a significant reduction in state 3 respiration using malate and pyruvate as substrate, caused by asimicin (concentration for 50% inhibition = 0.55 nmol/mg protein) or FO20 (I 50 = 1.69 μg/mg protein). No reductions of ADP:O or respiratory control ratios were observed in partially inhibited mitochondria. Oxygen uptake was restored and state 3 respiration was not inhibited when succinate was the substrate. These results are evidence of a site of inhibition between NADH and ubiquinone (site 1) within the electron transport chain.
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additional bioactive compounds and trilobacin a novel highly cytotoxic acetogenin from the bark of Asimina triloba
Journal of Natural Products, 1992Co-Authors: Gengxian Zhao, J L Mclaughlin, J K Rupprecht, Karl V WoodAbstract:: Fractionation of the EtOH extract of the bark of Asimina triloba, monitoring by brine shrimp lethality, has led to the isolation and structural elucidation of a novel highly cytotoxic Annonaceous acetogenin, trilobacin [1], in addition to six known compounds: asimicin 2], bullatacin [3], bullatacinone [4], N-p-coumaroyltyramine [5], N-trans-feruloyltyramine [6], and (+)-syringaresinol [7]. Acetogenin 1 was identified as a diastereomer of asimicin [2] by spectral and chemical methods, and both 1 and 2 showed potent and selective cytotoxicities in the NCI human tumor cell line screen.
