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Jerry L Mclaughlin – One of the best experts on this subject based on the ideXlab platform.

  • asimitrin and 4 hydroxytrilobin new bioactive annonaceous acetogenins from the seeds of Asimina triloba possessing a bis tetrahydrofuran ring
    Journal of Natural Products, 2005
    Co-Authors: Eun Joo Jung, Jerry L Mclaughlin

    Abstract:

    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, 2005
    Co-Authors: Eun Jung Kim, Eun Joo Jung, Mi-hee Woo, Kyung Mi Suh, Dal Hwan Kim, Chang Seob Seo, Jong Keun Son, Jerry L Mclaughlin

    Abstract:

    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, 1997
    Co-Authors: Kan He, Gengxian Zhao, Jinfeng Chao, Lu Zeng, Jerry L Mclaughlin

    Abstract:

    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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Paul Feeny – One of the best experts on this subject based on the ideXlab platform.

  • oviposition stimulant for the zebra swallowtail butterfly eurytides marcellus from the foliage of pawpaw Asimina triloba
    Chemoecology, 1998
    Co-Authors: Meena Haribal, Paul Feeny

    Abstract:

    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, 1998
    Co-Authors: Meena Haribal, Paul Feeny

    Abstract:

    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, 1998
    Co-Authors: Meena Haribal, Paul Feeny, Cathy C Lester

    Abstract:

    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.

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Meena Haribal – One of the best experts on this subject based on the ideXlab platform.

  • oviposition stimulant for the zebra swallowtail butterfly eurytides marcellus from the foliage of pawpaw Asimina triloba
    Chemoecology, 1998
    Co-Authors: Meena Haribal, Paul Feeny

    Abstract:

    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, 1998
    Co-Authors: Meena Haribal, Paul Feeny

    Abstract:

    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, 1998
    Co-Authors: Meena Haribal, Paul Feeny, Cathy C Lester

    Abstract:

    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.

    Free Register to Access Article