메뉴 건너뛰기




Volumn 76, Issue 13, 2010, Pages 1390-1404

Historic perspectives on Annonaceous acetogenins from the chemical bench to preclinical trials

Author keywords

acetogenin mimics; acetogenins; Annonaceae; anticancer activity; apoptosis; mitochondria complex I inhibitor; pesticidal activity

Indexed keywords

10 HYDROXYASIMICIN; 9 HYDROXYASIMICINONE; AA 005; ACETOGENIN; ALAC ACETOGENIN; ANNONA MURICATA EXTRACT; ANNONACIN; ASIMICIN; BULLATACIN; BULLATALICIN; CHERIMOLINE; DIEPOMURICANIN; GIGANTECIN; ISOANNORETICUIN; JIMENEZIN; LAHERRADURINE; LONGICIN; MEMBRANACIN; MURICATACIN; MURICIN A; MURICIN B; MURISOLIN; PLANT EXTRACT; ROLLICOSIN; ROLLIMEMBRIN; ROTENONE; SQUAMOSTOLIDE; SQUAMOXINONE; SYLVATICIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; UVARICIN; WYC AA 07;

EID: 77956658444     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0030-1250006     Document Type: Review
Times cited : (115)

References (156)
  • 1
    • 0031028432 scopus 로고    scopus 로고
    • Natural products in drug discovery and development
    • Cragg G M., Newman D J., Snader K M. Natural products in drug discovery and development. J Nat Prod 1997 60 52-60
    • (1997) J Nat Prod , vol.60 , pp. 52-60
    • Cragg, G.M.1    Newman, D.J.2    Snader, K.M.3
  • 2
    • 0015211527 scopus 로고
    • Plant antitumor agents. VI. Isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia
    • Wani M C., Taylor H L., Wall M E., Coggon P, McPhail A T. Plant antitumor agents. VI. Isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 1971 93 2325-2327
    • (1971) J Am Chem Soc , vol.93 , pp. 2325-2327
    • Wani, M.C.1    Taylor, H.L.2    Wall, M.E.3    Coggon, P.4    McPhail, A.T.5
  • 3
    • 7144248725 scopus 로고
    • Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata
    • Wall M E., Wani M C., Cook C E., Palmer K H., McPhail A T., Sim G A. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata. J Am Chem Soc 1966 88 3888-3890
    • (1966) J Am Chem Soc , vol.88 , pp. 3888-3890
    • Wall, M.E.1    Wani, M.C.2    Cook, C.E.3    Palmer, K.H.4    McPhail, A.T.5    Sim, G.A.6
  • 4
    • 0001595402 scopus 로고
    • Components of podophyllin. V. The constitution of podophyllotoxin
    • Hartwell J L., Schrecker A W. Components of podophyllin. V. The constitution of podophyllotoxin. J Am Chem Soc 1951 73 2909-2916
    • (1951) J Am Chem Soc , vol.73 , pp. 2909-2916
    • Hartwell, J.L.1    Schrecker, A.W.2
  • 5
    • 33947483339 scopus 로고
    • Vinca alkaloids. XXI. The structures of the oncolytic alkaloids vinblastine (VLB) and vincristine (VCR)
    • Neuss N, Gorman M, Hargrove W, Cone N J., Biemann K, Buechi G, Manning R E. Vinca alkaloids. XXI. The structures of the oncolytic alkaloids vinblastine (VLB) and vincristine (VCR). J Am Chem Soc 1964 86 1440-1442
    • (1964) J Am Chem Soc , vol.86 , pp. 1440-1442
    • Neuss, N.1    Gorman, M.2    Hargrove, W.3    Cone, N.J.4    Biemann, K.5    Buechi, G.6    Manning, R.E.7
  • 6
    • 0014490968 scopus 로고
    • Adriamycin (14-hydroxydaunomycin), a novel antitumor antibiotic
    • Arcamone F, Franceschi G, Penco S, Selva A. Adriamycin (14-hydroxydaunomycin), a novel antitumor antibiotic. Tetrahedron Lett 1969 13 1007-1010
    • (1969) Tetrahedron Lett , vol.13 , pp. 1007-1010
    • Arcamone, F.1    Franceschi, G.2    Penco, S.3    Selva, A.4
  • 12
    • 38949092645 scopus 로고    scopus 로고
    • New research and development on the Formosan annonaceous plants. Atta-ur-Rahman Amsterdam Elsevier B.V.
    • Wu Y C. New research and development on the Formosan annonaceous plants. Atta-ur-Rahman Studies in natural products chemistry, vol. 33. Amsterdam Elsevier B.V. 2006 957-1024
    • (2006) Studies in Natural Products Chemistry, Vol. 33. , pp. 957-1024
    • Wu, Y.C.1
  • 13
    • 0037480025 scopus 로고    scopus 로고
    • Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line
    • Nakanishi Y, Chang F R., Liaw C C., Wu Y C., Bastow K F., Lee K H. Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line. J Med Chem 2003 46 3185-3188
    • (2003) J Med Chem , vol.46 , pp. 3185-3188
    • Nakanishi, Y.1    Chang, F.R.2    Liaw, C.C.3    Wu, Y.C.4    Bastow, K.F.5    Lee, K.H.6
  • 14
    • 0019982429 scopus 로고
    • Uvaricin, a new antitumor agent from Uvaria accuminata (Annonaceae)
    • Jolad S D., Hoffmann J J., Schram K H., Cole J R. Uvaricin, a new antitumor agent from Uvaria accuminata (Annonaceae). J Org Chem 1982 47 3151-3153
    • (1982) J Org Chem , vol.47 , pp. 3151-3153
    • Jolad, S.D.1    Hoffmann, J.J.2    Schram, K.H.3    Cole, J.R.4
  • 15
    • 0023251002 scopus 로고
    • Annonacin, a novel, biologically active polyketide from Annona densicoma
    • McCloud T G., Smith D L., Chang C-J, Cassady J M. Annonacin, a novel, biologically active polyketide from Annona densicoma. Experientia 1987 43 947-949
    • (1987) Experientia , vol.43 , pp. 947-949
    • McCloud, T.G.1    Smith, D.L.2    Chang, C.-J.3    Cassady, J.M.4
  • 16
    • 0024209581 scopus 로고
    • Squamocin, a new cytotoxic bis-tetrahydrofuran containing acetogenin from Annona squamosa
    • Fujimoto Y, Eguchi T, Kakinuma K, Ikekawa N, Sahai M, Gupta Y K. Squamocin, a new cytotoxic bis-tetrahydrofuran containing acetogenin from Annona squamosa. Chem Pharm Bull 1988 36 4802-4806
    • (1988) Chem Pharm Bull , vol.36 , pp. 4802-4806
    • Fujimoto, Y.1    Eguchi, T.2    Kakinuma, K.3    Ikekawa, N.4    Sahai, M.5    Gupta, Y.K.6
  • 18
    • 0021280905 scopus 로고
    • Cherimoline et dihydrocherimoline: deux nouvelles -lactones bis-tetrahydrofuranniques possedant une activite antimicrobienne
    • Cortes D, Rios J L., Villar A, Valverde S. Cherimoline et dihydrocherimoline: deux nouvelles -lactones bis-tetrahydrofuranniques possedant une activite antimicrobienne. Tetrahedron Lett 1984 25 3199-3202
    • (1984) Tetrahedron Lett , vol.25 , pp. 3199-3202
    • Cortes, D.1    Rios, J.L.2    Villar, A.3    Valverde, S.4
  • 19
    • 0000042644 scopus 로고
    • Acetogenins of the Annonaceae. Part 20. Bioactive acetogenins from seeds of Annona cherimolia
    • Cortes D, Myint S H., Dupont B, Davoust D. Acetogenins of the Annonaceae. Part 20. Bioactive acetogenins from seeds of Annona cherimolia. Phytochemistry 1993 32 1475-1482
    • (1993) Phytochemistry , vol.32 , pp. 1475-1482
    • Cortes, D.1    Myint, S.H.2    Dupont, B.3    Davoust, D.4
  • 20
    • 0010348122 scopus 로고
    • Acetogenins, aporphinoids, and azaanthraquinone from Annona cherimolia seeds
    • Rios J L., Cortes D, Valverde S. Acetogenins, aporphinoids, and azaanthraquinone from Annona cherimolia seeds. Planta Med 1989 55 321-323
    • (1989) Planta Med , vol.55 , pp. 321-323
    • Rios, J.L.1    Cortes, D.2    Valverde, S.3
  • 21
    • 2542602806 scopus 로고
    • On the stereochemistry of the bistetrahydrofuranyl moiety of uvaricin. Proton chemical shifts can play a crucial role in complex structure determination
    • Hoye T R., Suhadolnik J C. On the stereochemistry of the bistetrahydrofuranyl moiety of uvaricin. Proton chemical shifts can play a crucial role in complex structure determination. J Am Chem Soc 1987 109 4402-4403
    • (1987) J Am Chem Soc , vol.109 , pp. 4402-4403
    • Hoye, T.R.1    Suhadolnik, J.C.2
  • 22
    • 0023757314 scopus 로고
    • Validation of the proton NMR chemical shift method for determination of stereochemistry in the bistetrahydrofuranyl moiety of uvaricin-related acetogenins from Annonaceae: Rolliniastatin 1 (and asimicin)
    • Hoye T R., Zhuang Z P. Validation of the proton NMR chemical shift method for determination of stereochemistry in the bistetrahydrofuranyl moiety of uvaricin-related acetogenins from Annonaceae: rolliniastatin 1 (and asimicin). J Org Chem 1988 53 5578-5580
    • (1988) J Org Chem , vol.53 , pp. 5578-5580
    • Hoye, T.R.1    Zhuang, Z.P.2
  • 25
    • 0033473481 scopus 로고    scopus 로고
    • A note on the determination of absolute configuration of acetogenins by circular dichroism
    • Gawronski J, Wu Y C. A note on the determination of absolute configuration of acetogenins by circular dichroism. Polish J Chem 1999 73 241-243
    • (1999) Polish J Chem , vol.73 , pp. 241-243
    • Gawronski, J.1    Wu, Y.C.2
  • 26
    • 0025295765 scopus 로고
    • The relative configuration of acetogenins isolated from Annona squamosa: Annonin i (squamocin) and annonin VI
    • Born L, Lieb F, Lorentzen J P., Moeschler H, Nonfon M, Soellner R, Wendisch D. The relative configuration of acetogenins isolated from Annona squamosa: annonin I (squamocin) and annonin VI. Planta Med 1990 56 312-316
    • (1990) Planta Med , vol.56 , pp. 312-316
    • Born, L.1    Lieb, F.2    Lorentzen, J.P.3    Moeschler, H.4    Nonfon, M.5    Soellner, R.6    Wendisch, D.7
  • 27
    • 0000909231 scopus 로고
    • Symmetry-assisted synthesis of triepoxide stereoisomers of E,Z,E -dodeca-2,6,10-trien-1,12-diol and their cascade reactions to 2, 5-linked bistetrahydrofurans
    • Hoye T R., Suhadolnik J C. Symmetry-assisted synthesis of triepoxide stereoisomers of E,Z,E -dodeca-2,6,10-trien-1,12-diol and their cascade reactions to 2, 5-linked bistetrahydrofurans. J Am Chem Soc 1985 107 5312-5313
    • (1985) J Am Chem Soc , vol.107 , pp. 5312-5313
    • Hoye, T.R.1    Suhadolnik, J.C.2
  • 28
    • 77956663638 scopus 로고    scopus 로고
    • Taipei Lungwei Printing Co. Ltd.
    • Huang T S. Flora of Taiwan, vol. 2. Taipei Lungwei Printing Co. Ltd. 1996 415-419
    • (1996) Flora of Taiwan , vol.2 , pp. 415-419
    • Huang, T.S.1
  • 30
    • 0028986928 scopus 로고
    • Bioactive constituents from the stems of Annona montana
    • Wu Y C., Chang G Y., Ko F N., Teng C M. Bioactive constituents from the stems of Annona montana. Planta Med 1995 61 146-149
    • (1995) Planta Med , vol.61 , pp. 146-149
    • Wu, Y.C.1    Chang, G.Y.2    Ko, F.N.3    Teng, C.M.4
  • 31
    • 0030013646 scopus 로고    scopus 로고
    • Antiplatelet and vasorelaxing actions of some aporphinoids
    • Chen K S., Ko F N., Teng C M., Wu Y C. Antiplatelet and vasorelaxing actions of some aporphinoids. Planta Med 1996 62 133-136
    • (1996) Planta Med , vol.62 , pp. 133-136
    • Chen, K.S.1    Ko, F.N.2    Teng, C.M.3    Wu, Y.C.4
  • 32
    • 0028148846 scopus 로고
    • Antimuscarinic action of liriodenine, isolated form Fissistigma glaucescens, in canine tracheal smooth muscle
    • Lin C H., Yang C M., Ko F N., Wu Y C., Teng C M. Antimuscarinic action of liriodenine, isolated form Fissistigma glaucescens, in canine tracheal smooth muscle. Br J Pharmacol 1994 113 1464-1470
    • (1994) Br J Pharmacol , vol.113 , pp. 1464-1470
    • Lin, C.H.1    Yang, C.M.2    Ko, F.N.3    Wu, Y.C.4    Teng, C.M.5
  • 33
    • 0030010878 scopus 로고    scopus 로고
    • Electrophysiological mechanisms for antiarrhythmic efficacy and positive inotropy of liriodenine, a natural aporphine alkaloid from Fissistigma glaucescens
    • Chang G J., Wu M H., Wu Y C., Su M J. Electrophysiological mechanisms for antiarrhythmic efficacy and positive inotropy of liriodenine, a natural aporphine alkaloid from Fissistigma glaucescens. Br J Pharmacol 1996 118 1571-1583
    • (1996) Br J Pharmacol , vol.118 , pp. 1571-1583
    • Chang, G.J.1    Wu, M.H.2    Wu, Y.C.3    Su, M.J.4
  • 34
    • 0027198082 scopus 로고
    • Pharmacological activity of ()-discretamine, a novel vascular -adrenoceptor and 5-hydroxytryptamine receptor antagonist, isolated from Fissistigma glaucescens
    • Ko F N., Yu S M., Su M J., Wu Y C., Teng C M. Pharmacological activity of ()-discretamine, a novel vascular -adrenoceptor and 5-hydroxytryptamine receptor antagonist, isolated from Fissistigma glaucescens. Br J Pharmacol 1993 110 882-888
    • (1993) Br J Pharmacol , vol.110 , pp. 882-888
    • Ko, F.N.1    Yu, S.M.2    Su, M.J.3    Wu, Y.C.4    Teng, C.M.5
  • 37
    • 0001305129 scopus 로고
    • Studies on acetogenins from Formosan Annonaceous plants. 3. Diepoxymontin, a novel acetogenin from Annona montana
    • Wu Y C., Chang F R., Chen K S., Liang S C., Lee M R. Studies on acetogenins from Formosan Annonaceous plants. 3. Diepoxymontin, a novel acetogenin from Annona montana. Heterocycles 1994 38 1475-1478
    • (1994) Heterocycles , vol.38 , pp. 1475-1478
    • Wu, Y.C.1    Chang, F.R.2    Chen, K.S.3    Liang, S.C.4    Lee, M.R.5
  • 38
    • 0001589633 scopus 로고
    • Annoreticuin and isoannoreticuin: Two new cytotoxic acetogenins from Annona reticulata
    • Wu Y C., Chang F R., Duh C Y., Wang S K. Annoreticuin and isoannoreticuin: two new cytotoxic acetogenins from Annona reticulata. Heterocycles 1992 34 667-674
    • (1992) Heterocycles , vol.34 , pp. 667-674
    • Wu, Y.C.1    Chang, F.R.2    Duh, C.Y.3    Wang, S.K.4
  • 39
    • 0027484450 scopus 로고
    • Studies on the acetogenins of Formosan Annonaceous plants, II. Cytotoxic acetogenins from Annona reticulata
    • Chang F R., Wu Y C., Duh C Y., Wang S K. Studies on the acetogenins of Formosan Annonaceous plants, II. Cytotoxic acetogenins from Annona reticulata. J Nat Prod 1993 56 1688-1694
    • (1993) J Nat Prod , vol.56 , pp. 1688-1694
    • Chang, F.R.1    Wu, Y.C.2    Duh, C.Y.3    Wang, S.K.4
  • 40
    • 0006001324 scopus 로고
    • Chemical compositions of Goniothalamus howii (I)
    • Zhang L, Yang R, Wu X. Chemical compositions of Goniothalamus howii (I). Zhiwu Xuebao 1993 35 390-396
    • (1993) Zhiwu Xuebao , vol.35 , pp. 390-396
    • Zhang, L.1    Yang, R.2    Wu, X.3
  • 41
    • 21144477228 scopus 로고
    • Squamostatin-B, a new polyketide from Annona squamosa (Annonaceae)
    • Yu J, Luo X, Sun L, Liu C, Hong S, Ma L. Squamostatin-B, a new polyketide from Annona squamosa (Annonaceae). Chin Chem Lett 1993 4 423-426
    • (1993) Chin Chem Lett , vol.4 , pp. 423-426
    • Yu, J.1    Luo, X.2    Sun, L.3    Liu, C.4    Hong, S.5    Ma, L.6
  • 42
    • 21844494102 scopus 로고
    • Three new bioactive Annonaceous acetogeninins from Annona muricata
    • Li C M., Mu Q, Hao X J., Sun H D., Zheng H L., Wu Y C. Three new bioactive Annonaceous acetogeninins from Annona muricata. Chin Chem Lett 1994 5 747-750
    • (1994) Chin Chem Lett , vol.5 , pp. 747-750
    • Li, C.M.1    Mu, Q.2    Hao, X.J.3    Sun, H.D.4    Zheng, H.L.5    Wu, Y.C.6
  • 44
    • 0027315726 scopus 로고
    • 30-, 31-, and 32-hydroxybullatacinones: Bioactive terminally hydroxylated Annonaceous acetogenins from Annona bullata
    • Gu Z M., Fang X P., Miesbauer L R., Smith D L., McLaughlin J L. 30-, 31-, and 32-hydroxybullatacinones: bioactive terminally hydroxylated Annonaceous acetogenins from Annona bullata. J Nat Prod 1993 56 870-876
    • (1993) J Nat Prod , vol.56 , pp. 870-876
    • Gu, Z.M.1    Fang, X.P.2    Miesbauer, L.R.3    Smith, D.L.4    McLaughlin, J.L.5
  • 45
    • 0027398489 scopus 로고
    • New cytotoxic Annonaceous acetogenins: Bullatanocin and cis - And trans -bullatanocinone, from Annona bullata (Annonaceae)
    • Gu Z M., Fang X P., Rieser M J., Hui Y H., Miesbauer L R., Smith D L., Wood K V., McLaughlin J L. New cytotoxic Annonaceous acetogenins: bullatanocin and cis - and trans -bullatanocinone, from Annona bullata (Annonaceae). Tetrahedron 1993 49 747-754
    • (1993) Tetrahedron , vol.49 , pp. 747-754
    • Gu, Z.M.1    Fang, X.P.2    Rieser, M.J.3    Hui, Y.H.4    Miesbauer, L.R.5    Smith, D.L.6    Wood, K.V.7    McLaughlin, J.L.8
  • 46
    • 0001126537 scopus 로고
    • Bullacin: A new cytotoxic Annonaceous acetogenin from Annona bullata
    • Gu Z M., Fang X P., Zeng L, Wood K V., McLaughlin J L. Bullacin: a new cytotoxic Annonaceous acetogenin from Annona bullata. Heterocycles 1993 36 2221-2228
    • (1993) Heterocycles , vol.36 , pp. 2221-2228
    • Gu, Z.M.1    Fang, X.P.2    Zeng, L.3    Wood, K.V.4    McLaughlin, J.L.5
  • 48
    • 0026099671 scopus 로고
    • Muricatacin: A simple biologically active acetogenin derivative from the seeds of Annona muricata (Annonaceae)
    • Rieser M J., Kozlowski J F., Wood K V., McLaughlin J L. Muricatacin: a simple biologically active acetogenin derivative from the seeds of Annona muricata (Annonaceae). Tetrahedron Lett 1991 32 1137-1140
    • (1991) Tetrahedron Lett , vol.32 , pp. 1137-1140
    • Rieser, M.J.1    Kozlowski, J.F.2    Wood, K.V.3    McLaughlin, J.L.4
  • 49
    • 0027054720 scopus 로고
    • Determination of absolute configuration of stereogenic carbinol centers in Annonaceous acetogenins by proton and fluorine-19 NMR analysis of Mosher ester derivatives
    • Rieser M J., Hui Y H., Rupprecht J K., Kozlowski J F., Wood K V., McLaughlin J L., Hanson P R., Zhuang Z, Hoye T R. Determination of absolute configuration of stereogenic carbinol centers in Annonaceous acetogenins by proton and fluorine-19 NMR analysis of Mosher ester derivatives. J Am Chem Soc 1992 114 10203-10213
    • (1992) J Am Chem Soc , vol.114 , pp. 10203-10213
    • Rieser, M.J.1    Hui, Y.H.2    Rupprecht, J.K.3    Kozlowski, J.F.4    Wood, K.V.5    McLaughlin, J.L.6    Hanson, P.R.7    Zhuang, Z.8    Hoye, T.R.9
  • 52
    • 0000115810 scopus 로고
    • Acetogenins of Annonaceae. 34. Isoacetogenins, artifacts issued from translacationization from annonaceous acetogenins
    • Duret P, Laurens A, Hocquemiller R, Cortex D, Cave A. Acetogenins of Annonaceae. 34. Isoacetogenins, artifacts issued from translacationization from annonaceous acetogenins. Heterocycles 1994 39 741-749
    • (1994) Heterocycles , vol.39 , pp. 741-749
    • Duret, P.1    Laurens, A.2    Hocquemiller, R.3    Cortex, D.4    Cave, A.5
  • 53
    • 0343632337 scopus 로고    scopus 로고
    • Epimerization of Annonaceous acetogenins under basic conditions
    • Duret P, Figadere B, Hocquemiller R, Cave A. Epimerization of Annonaceous acetogenins under basic conditions. Tetrahedron Lett 1997 38 8849-8852
    • (1997) Tetrahedron Lett , vol.38 , pp. 8849-8852
    • Duret, P.1    Figadere, B.2    Hocquemiller, R.3    Cave, A.4
  • 54
    • 0032726430 scopus 로고    scopus 로고
    • Using countercurrent chromatography to assist in the purification of new Annonaceous acetogenins from Annona squamosa
    • Hopp D C., Conway W D., McLaughlin J L. Using countercurrent chromatography to assist in the purification of new Annonaceous acetogenins from Annona squamosa. Phytochem Anal 1999 10 339-347
    • (1999) Phytochem Anal , vol.10 , pp. 339-347
    • Hopp, D.C.1    Conway, W.D.2    McLaughlin, J.L.3
  • 56
    • 0032504011 scopus 로고    scopus 로고
    • Determination of absolute configurations of carbinols of Annonaceous acetogenins with 2-naphthylmethoxyacetic acid esters
    • Duret P, Waechter A-I, Figadere B, Hocquemiller R, Cave A. Determination of absolute configurations of carbinols of Annonaceous acetogenins with 2-naphthylmethoxyacetic acid esters. J Org Chem 1998 63 4717-4720
    • (1998) J Org Chem , vol.63 , pp. 4717-4720
    • Duret, P.1    Waechter, A.-I.2    Figadere, B.3    Hocquemiller, R.4    Cave, A.5
  • 57
    • 84989152271 scopus 로고
    • Structural studies of polyhydroxybis(tetrahydrofuran) acetogenins from Annona squamosa using the combination of chemical derivatization and precursor-ion scanning mass spectrometry
    • Hirayama K, Akashi S, Yuji R, Niitsu U, Fujimoto Y. Structural studies of polyhydroxybis(tetrahydrofuran) acetogenins from Annona squamosa using the combination of chemical derivatization and precursor-ion scanning mass spectrometry. Org Mass Spectrom 1993 28 1516-1524
    • (1993) Org Mass Spectrom , vol.28 , pp. 1516-1524
    • Hirayama, K.1    Akashi, S.2    Yuji, R.3    Niitsu, U.4    Fujimoto, Y.5
  • 58
    • 0030959559 scopus 로고    scopus 로고
    • Screening for annonaceous acetogenins in bioactive plant extracts by liquid chromatography/mass spectrometry
    • DOI 10.1021/np960487i
    • Gu Z M., Zhou D, Wu J, Shi G, Zeng L, McLaughlin J L. Screening for Annonaceous acetogenins in bioactive plant extracts by liquid chromatography/mass spectrometry. J Nat Prod 1997 60 242-248 (Pubitemid 27146457)
    • (1997) Journal of Natural Products , vol.60 , Issue.3 , pp. 242-248
    • Gu, Z.-M.1    Zhou, D.2    Wu, J.3    Shi, G.4    Zeng, L.5    McLaughlin, J.L.6
  • 59
    • 0034910949 scopus 로고    scopus 로고
    • Novel cytotoxic Annonaceous acetogenins from Annona muricata
    • Chang F R., Wu Y C. Novel cytotoxic Annonaceous acetogenins from Annona muricata. J Nat Prod 2001 64 925-931
    • (2001) J Nat Prod , vol.64 , pp. 925-931
    • Chang, F.R.1    Wu, Y.C.2
  • 60
    • 0037362061 scopus 로고    scopus 로고
    • New adjacent bis-tetrahydrofuran Annonaceous acetogenins from Annona muricata
    • Chang F R., Liaw C C., Lin C Y., Chou C J., Chiu H F., Wu Y C. New adjacent bis-tetrahydrofuran Annonaceous acetogenins from Annona muricata. Planta Med 2003 69 241-246
    • (2003) Planta Med , vol.69 , pp. 241-246
    • Chang, F.R.1    Liaw, C.C.2    Lin, C.Y.3    Chou, C.J.4    Chiu, H.F.5    Wu, Y.C.6
  • 62
    • 0037331724 scopus 로고    scopus 로고
    • A novel constituent from Rollinia mucosa, rollicosin, and a new approach to develop Annonaceous acetogenins as potential antitumor agents
    • Liaw C C., Chang F R., Wu M J., Wu Y C. A novel constituent from Rollinia mucosa, rollicosin, and a new approach to develop Annonaceous acetogenins as potential antitumor agents. J Nat Prod 2003 66 279-281
    • (2003) J Nat Prod , vol.66 , pp. 279-281
    • Liaw, C.C.1    Chang, F.R.2    Wu, M.J.3    Wu, Y.C.4
  • 63
    • 0038297954 scopus 로고    scopus 로고
    • A new cytotoxic acetogenin from the seeds of Annona squamosa
    • Xie H H., Wei X Y., Wang J D., Liu M F., Yang R Z. A new cytotoxic acetogenin from the seeds of Annona squamosa. Chin Chem Lett 2003 14 588-590
    • (2003) Chin Chem Lett , vol.14 , pp. 588-590
    • Xie, H.H.1    Wei, X.Y.2    Wang, J.D.3    Liu, M.F.4    Yang, R.Z.5
  • 65
    • 0035800417 scopus 로고    scopus 로고
    • Bullatacin, a potent antitumor Annonaceous acetogenin, inhibits proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction
    • Chih H W., Chiu H F., Tang K S., Chang F R., Wu Y C. Bullatacin, a potent antitumor Annonaceous acetogenin, inhibits proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction. Life Sci 2001 69 1321-1331
    • (2001) Life Sci , vol.69 , pp. 1321-1331
    • Chih, H.W.1    Chiu, H.F.2    Tang, K.S.3    Chang, F.R.4    Wu, Y.C.5
  • 66
    • 33846081978 scopus 로고    scopus 로고
    • Effects of plant lactones on the production of biofilm of Pseudomonas aeruginosa
    • Cartagena E, Colom O A., Neske A, Valdez J C., Bardon A. Effects of plant lactones on the production of biofilm of Pseudomonas aeruginosa. Chem Pharm Bull 2007 55 22-25
    • (2007) Chem Pharm Bull , vol.55 , pp. 22-25
    • Cartagena, E.1    Colom, O.A.2    Neske, A.3    Valdez, J.C.4    Bardon, A.5
  • 68
    • 0028318990 scopus 로고
    • Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial NADH dehydrogenase (complex I)
    • Degli Esposti M, Ghelli A, Ratta M, Cortes D, Estornell E. Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial NADH dehydrogenase (complex I). Biochem J 1994 301 161-167
    • (1994) Biochem J , vol.301 , pp. 161-167
    • Degli Esposti, M.1    Ghelli, A.2    Ratta, M.3    Cortes, D.4    Estornell, E.5
  • 69
    • 0029129524 scopus 로고
    • Tumor cell growth inhibition by several Anonaceous acetogenins in an in vitro disk diffusion assay
    • Oberlies N H., Jones J L., Corbett T H., Fotopoulos S S., McLaughlin J L. Tumor cell growth inhibition by several Anonaceous acetogenins in an in vitro disk diffusion assay. Cancer Lett 1995 96 55-62
    • (1995) Cancer Lett , vol.96 , pp. 55-62
    • Oberlies, N.H.1    Jones, J.L.2    Corbett, T.H.3    Fotopoulos, S.S.4    McLaughlin, J.L.5
  • 70
    • 0031149817 scopus 로고    scopus 로고
    • The Anonaceous acetogenin bullatacin is cytotoxic against multidrug-resistant human mammary adenocarcinoma cells
    • Oberlies N H., Croy V L., Harrison M L., McLaughlin J L. The Anonaceous acetogenin bullatacin is cytotoxic against multidrug-resistant human mammary adenocarcinoma cells. Cancer Lett 1997 115 73-79
    • (1997) Cancer Lett , vol.115 , pp. 73-79
    • Oberlies, N.H.1    Croy, V.L.2    Harrison, M.L.3    McLaughlin, J.L.4
  • 71
    • 0032548446 scopus 로고    scopus 로고
    • Membrane conformations and their relation to cytotoxicity of asimicin and its analogs
    • Shimada H, Grutzner J B., Kozlowski J F., McLaughlin J L. Membrane conformations and their relation to cytotoxicity of asimicin and its analogs. Biochemistry 1998 37 854-866
    • (1998) Biochemistry , vol.37 , pp. 854-866
    • Shimada, H.1    Grutzner, J.B.2    Kozlowski, J.F.3    McLaughlin, J.L.4
  • 73
    • 0344838548 scopus 로고    scopus 로고
    • Annonacin, a mono-tetrahydrofuran acetogenin, arrests cancer cells at the G1 phase and causes cytotoxicity in a Bax- and caspase-3-related pathway
    • Yuan S S. F., Chang H L., Chen H W., Yeh Y T., Kao Y H., Lin K H., Wu Y C., Su J H. Annonacin, a mono-tetrahydrofuran acetogenin, arrests cancer cells at the G1 phase and causes cytotoxicity in a Bax- and caspase-3-related pathway. Life Sci 2003 72 2853-2861
    • (2003) Life Sci , vol.72 , pp. 2853-2861
    • Yuan, S.S.F.1    Chang, H.L.2    Chen, H.W.3    Yeh, Y.T.4    Kao, Y.H.5    Lin, K.H.6    Wu, Y.C.7    Su, J.H.8
  • 74
    • 30544451660 scopus 로고    scopus 로고
    • Selective cytotoxicity of squamocin on T24 bladder cancer cells at the S-phase via a Bax-, Bad-, and caspase-3-related pathways
    • Yuan S S. F., Chang H L., Chen H W., Kuo F C., Liaw C C., Su J H., Wu Y C. Selective cytotoxicity of squamocin on T24 bladder cancer cells at the S-phase via a Bax-, Bad-, and caspase-3-related pathways. Life Sci 2006 78 869-874
    • (2006) Life Sci , vol.78 , pp. 869-874
    • Yuan, S.S.F.1    Chang, H.L.2    Chen, H.W.3    Kuo, F.C.4    Liaw, C.C.5    Su, J.H.6    Wu, Y.C.7
  • 75
    • 33645381493 scopus 로고    scopus 로고
    • Induction of G2/M phase arrest by squamocin in chronic myeloid leukemia (K562) cells
    • Lu M C., Yang S H., Hwang S L., Lu Y J., Lin Y H., Wang S R., Wu Y C., Lin S R. Induction of G2/M phase arrest by squamocin in chronic myeloid leukemia (K562) cells. Life Sci 2006 78 2378-2383
    • (2006) Life Sci , vol.78 , pp. 2378-2383
    • Lu, M.C.1    Yang, S.H.2    Hwang, S.L.3    Lu, Y.J.4    Lin, Y.H.5    Wang, S.R.6    Wu, Y.C.7    Lin, S.R.8
  • 77
    • 0027032595 scopus 로고
    • Evaluation of various parts of the paw paw tree, Asimina triloba (Annonaceae), as commercial sources of the pesticidal Anonaceous acetogenins
    • Ratnayake S, Rupprecht J K., Potter W M., McLaughlin J L. Evaluation of various parts of the paw paw tree, Asimina triloba (Annonaceae), as commercial sources of the pesticidal Anonaceous acetogenins. J Econ Entomol 1992 85 2353-2356
    • (1992) J Econ Entomol , vol.85 , pp. 2353-2356
    • Ratnayake, S.1    Rupprecht, J.K.2    Potter, W.M.3    McLaughlin, J.L.4
  • 78
    • 0030940044 scopus 로고    scopus 로고
    • Comparative structure-activity relationship evaluations of Anonaceous acetogenins for pesticidal activity
    • He K, Zeng L, Ye Q, Shi G, Oberlies N H., Zhao G X., Njoku C J., McLaughlin J L. Comparative structure-activity relationship evaluations of Anonaceous acetogenins for pesticidal activity. Pestic Sci 1997 49 372-378
    • (1997) Pestic Sci , vol.49 , pp. 372-378
    • He, K.1    Zeng, L.2    Ye, Q.3    Shi, G.4    Oberlies, N.H.5    Zhao, G.X.6    Njoku, C.J.7    McLaughlin, J.L.8
  • 79
    • 0032085319 scopus 로고    scopus 로고
    • Annonaceous acetogenins as natural pesticides: Potent toxicity against insecticide-susceptible and -resistant German cockroaches (Dictyoptera: Blattellidae)
    • Alali F Q., Kaakeh W, Bennett G W., McLaughlin J L. Annonaceous acetogenins as natural pesticides: potent toxicity against insecticide- susceptible and -resistant German cockroaches (Dictyoptera: Blattellidae). J Econ Entomol 1998 91 641-649
    • (1998) J Econ Entomol , vol.91 , pp. 641-649
    • Alali, F.Q.1    Kaakeh, W.2    Bennett, G.W.3    McLaughlin, J.L.4
  • 80
    • 85008114486 scopus 로고
    • Isolation and insecticidal activity of three acetogenins from seeds of pond apple, Annona glabra L
    • Ohsawa K, Atsuzawa S, Mitsui T, Yamamoto I. Isolation and insecticidal activity of three acetogenins from seeds of pond apple, Annona glabra L. Nippon Noyaku Gakkaishi 1991 16 93-96
    • (1991) Nippon Noyaku Gakkaishi , vol.16 , pp. 93-96
    • Ohsawa, K.1    Atsuzawa, S.2    Mitsui, T.3    Yamamoto, I.4
  • 82
    • 29344474961 scopus 로고
    • Inhibition of respiration at site i by asimicin, an insecticidal acetogenin of the pawpaw, Asimina triloba (Annonaceae)
    • Lewis M A., Arnason J T., Philogene B J. R., Rupprecht J K., McLaughlin J L. Inhibition of respiration at site I by asimicin, an insecticidal acetogenin of the pawpaw, Asimina triloba (Annonaceae). Pestic Biochem Physiol 1993 45 15-23
    • (1993) Pestic Biochem Physiol , vol.45 , pp. 15-23
    • Lewis, M.A.1    Arnason, J.T.2    Philogene, B.J.R.3    Rupprecht, J.K.4    McLaughlin, J.L.5
  • 84
    • 0028326253 scopus 로고
    • New inhibitors of complex i of the mitochondrial electron transport chain with activity as pesticides
    • Hollingworth R M., Ahammadsahib K I., Gadelhak G, McLaughlin J L. New inhibitors of complex I of the mitochondrial electron transport chain with activity as pesticides. Biochem Soc Trans 1994 22 230-233
    • (1994) Biochem Soc Trans , vol.22 , pp. 230-233
    • Hollingworth, R.M.1    Ahammadsahib, K.I.2    Gadelhak, G.3    McLaughlin, J.L.4
  • 85
    • 0032551770 scopus 로고    scopus 로고
    • Essential structural factors of Annonaceous acetogenins as potent inhibitors of mitochondrial complex I
    • Miyoshi H, Ohshima M, Shimada H, Akagi T, Iwamura H, McLaughlin J L. Essential structural factors of Annonaceous acetogenins as potent inhibitors of mitochondrial complex I. Biochim Biophys Acta 1998 1365 443-452
    • (1998) Biochim Biophys Acta , vol.1365 , pp. 443-452
    • Miyoshi, H.1    Ohshima, M.2    Shimada, H.3    Akagi, T.4    Iwamura, H.5    McLaughlin, J.L.6
  • 86
    • 22944438058 scopus 로고    scopus 로고
    • Inhibitors of mitochondrial respiratory enzymes
    • Miyoshi H. Inhibitors of mitochondrial respiratory enzymes. J Pestic Sci 2005 30 120-121
    • (2005) J Pestic Sci , vol.30 , pp. 120-121
    • Miyoshi, H.1
  • 87
    • 0034693817 scopus 로고    scopus 로고
    • Definition of crucial structural factors of acetogenins, potent inhibitors of mitochondrial complex I
    • Takada M, Kuwabara K, Nakato H, Tanaka A, Iwamura H, Miyoshi H. Definition of crucial structural factors of acetogenins, potent inhibitors of mitochondrial complex I. Biochim Biophys Acta 2000 1460 302-310
    • (2000) Biochim Biophys Acta , vol.1460 , pp. 302-310
    • Takada, M.1    Kuwabara, K.2    Nakato, H.3    Tanaka, A.4    Iwamura, H.5    Miyoshi, H.6
  • 88
    • 33744455508 scopus 로고    scopus 로고
    • Synthesis of photolabile lac-acetogenin for photoaffinity labeling of mitochondrial complex I
    • Murai M, Ichimaru N, Abe M, Nishioka T, Miyoshi H. Synthesis of photolabile lac-acetogenin for photoaffinity labeling of mitochondrial complex I. J Pestic Sci 2006 31 156-158
    • (2006) J Pestic Sci , vol.31 , pp. 156-158
    • Murai, M.1    Ichimaru, N.2    Abe, M.3    Nishioka, T.4    Miyoshi, H.5
  • 89
    • 33845683451 scopus 로고    scopus 로고
    • Effect of stereochemistry of lac-acetogenins on the inhibition of mitochondrial complex i (NADH-ubiquinone oxidoreductase)
    • Ichimaru N, Yoshinaga N, Nishioka T, Miyoshi H. Effect of stereochemistry of lac-acetogenins on the inhibition of mitochondrial complex I (NADH-ubiquinone oxidoreductase). Tetrahedron 2007 63 1127-1139
    • (2007) Tetrahedron , vol.63 , pp. 1127-1139
    • Ichimaru, N.1    Yoshinaga, N.2    Nishioka, T.3    Miyoshi, H.4
  • 91
    • 33845922401 scopus 로고    scopus 로고
    • Synthesis of murisolin, (15 R,16 R,19 R,20 S)-murisolin A, and (15 R,16 R,19 S,20 S)-16,19- cis -murisolin and their inhibitory action with bovine heart mitochondrial complex I
    • Hattori Y, Kimura Y, Moroda A, Konno H, Abe M, Miyoshi H, Goto T, Makabe H. Synthesis of murisolin, (15 R,16 R,19 R,20 S)-murisolin A, and (15 R,16 R,19 S,20 S)-16,19- cis -murisolin and their inhibitory action with bovine heart mitochondrial complex I. Chem Asian J 2006 1 894-904
    • (2006) Chem Asian J , vol.1 , pp. 894-904
    • Hattori, Y.1    Kimura, Y.2    Moroda, A.3    Konno, H.4    Abe, M.5    Miyoshi, H.6    Goto, T.7    Makabe, H.8
  • 92
    • 0028806971 scopus 로고
    • Longicin and goniothalamicinone: Novel bioactive monotetrahydrofuran acetogenins from Asimina longifolia
    • Ye Q, Zeng L, Zhang Y, Zhao G X., McLaughlin J L., Woo M H., Evert D R. Longicin and goniothalamicinone: novel bioactive monotetrahydrofuran acetogenins from Asimina longifolia. J Nat Prod 1995 58 1398-1406
    • (1995) J Nat Prod , vol.58 , pp. 1398-1406
    • Ye, Q.1    Zeng, L.2    Zhang, Y.3    Zhao, G.X.4    McLaughlin, J.L.5    Woo, M.H.6    Evert, D.R.7
  • 93
    • 24944584564 scopus 로고    scopus 로고
    • Total synthesis and structural confirmation of (+)-longicin
    • Hanessian S, Giroux S, Buffat M. Total synthesis and structural confirmation of (+)-longicin. Org Lett 2005 7 3989-3992
    • (2005) Org Lett , vol.7 , pp. 3989-3992
    • Hanessian, S.1    Giroux, S.2    Buffat, M.3
  • 94
    • 0031776480 scopus 로고    scopus 로고
    • Cis -Monotetrahydrofuran acetogenins from the roots of Annona muricata
    • Gleye C, Duret P, Laurens A, Hocquemiller R, Cave A. cis -Monotetrahydrofuran acetogenins from the roots of Annona muricata. J Nat Prod 1998 61 576-579
    • (1998) J Nat Prod , vol.61 , pp. 576-579
    • Gleye, C.1    Duret, P.2    Laurens, A.3    Hocquemiller, R.4    Cave, A.5
  • 95
    • 33747291925 scopus 로고    scopus 로고
    • 4-catalyzed oxidative cyclization of dienes
    • 4-catalyzed oxidative cyclization of dienes. Org Lett 2006 8 3433-3436
    • (2006) Org Lett , vol.8 , pp. 3433-3436
    • Goksel, H.1    Stark, C.B.W.2
  • 96
    • 33749020526 scopus 로고    scopus 로고
    • Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin
    • Zhao H, Gorman J S. T., Pagenkopf B L. Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin. Org Lett 2006 8 4379-4382
    • (2006) Org Lett , vol.8 , pp. 4379-4382
    • Zhao, H.1    Gorman, J.S.T.2    Pagenkopf, B.L.3
  • 97
    • 22944477099 scopus 로고    scopus 로고
    • Stereoselective syntheses of rolliniastatin 1, rollimembrin, and membranacin
    • Keum G, Hwang C H., Kang S B., Kim Y, Lee E. Stereoselective syntheses of rolliniastatin 1, rollimembrin, and membranacin. J Am Chem Soc 2005 127 10396-10399
    • (2005) J Am Chem Soc , vol.127 , pp. 10396-10399
    • Keum, G.1    Hwang, C.H.2    Kang, S.B.3    Kim, Y.4    Lee, E.5
  • 99
    • 0029908909 scopus 로고    scopus 로고
    • Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba
    • He K, Shi G, Zhao G X., Ye Q, Schwedler J T., Wood K V., McLaughlin J L. Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba. J Nat Prod 1996 59 1029-1034
    • (1996) J Nat Prod , vol.59 , pp. 1029-1034
    • He, K.1    Shi, G.2    Zhao, G.X.3    Ye, Q.4    Schwedler, J.T.5    Wood, K.V.6    McLaughlin, J.L.7
  • 101
    • 0027411367 scopus 로고
    • Acetogenins of the Annonaceae. 18. Rioclarin and membranacin, two new bis-tetrahydrofuran acetogenins of the seeds of Rollinia membranacea
    • Saez J, Sahpaz S, Villaescusa L, Hocquemiller R, Cave A, Cortes D. Acetogenins of the Annonaceae. 18. Rioclarin and membranacin, two new bis-tetrahydrofuran acetogenins of the seeds of Rollinia membranacea. J Nat Prod 1993 56 351-356
    • (1993) J Nat Prod , vol.56 , pp. 351-356
    • Saez, J.1    Sahpaz, S.2    Villaescusa, L.3    Hocquemiller, R.4    Cave, A.5    Cortes, D.6
  • 102
    • 33747221235 scopus 로고    scopus 로고
    • 2 core symmetry. Total synthesis of asimicin and a C32 analogue
    • 2 core symmetry. Total synthesis of asimicin and a C32 analogue. Org Lett 2006 8 3557-3560
    • (2006) Org Lett , vol.8 , pp. 3557-3560
    • Marshall, J.A.1    Sabatini, J.J.2
  • 103
    • 0030007523 scopus 로고    scopus 로고
    • Longimicins A D: Novel bioactive acetogenins from Asimina longifolia (Annonaceae) and structure-activity relationships of asimicin type of annonaceous acetogenins
    • Ye Q, He K, Oberlies N H., Zeng L, Shi G, Evert D, McLaughlin J L. Longimicins A D: novel bioactive acetogenins from Asimina longifolia (Annonaceae) and structure-activity relationships of asimicin type of annonaceous acetogenins. J Med Chem 1996 39 1790-1796
    • (1996) J Med Chem , vol.39 , pp. 1790-1796
    • Ye, Q.1    He, K.2    Oberlies, N.H.3    Zeng, L.4    Shi, G.5    Evert, D.6    McLaughlin, J.L.7
  • 106
    • 33644560625 scopus 로고    scopus 로고
    • Synthesis of the proposed structure of mucoxin via regio- and stereoselective tetrahydrofuran ring-forming strategies
    • Narayan R S., Borhan B. Synthesis of the proposed structure of mucoxin via regio- and stereoselective tetrahydrofuran ring-forming strategies. J Org Chem 2006 71 1416-1429
    • (2006) J Org Chem , vol.71 , pp. 1416-1429
    • Narayan, R.S.1    Borhan, B.2
  • 107
    • 0000160963 scopus 로고
    • Absolute stereochemistries of sylvaticin and 12,15- cis -sylvaticin, bioactive C-20,23- cis nonadjacent bistetrahydrofuran Annonaceous acetogenins, from Rollinia mucosa
    • Shi G, Zheng L, Gu Z-M, MacDougal J M., McLaughlin J L. Absolute stereochemistries of sylvaticin and 12,15- cis -sylvaticin, bioactive C-20,23- cis nonadjacent bistetrahydrofuran Annonaceous acetogenins, from Rollinia mucosa. Heterocycles 1995 41 1785-1796
    • (1995) Heterocycles , vol.41 , pp. 1785-1796
    • Shi, G.1    Zheng, L.2    Gu, Z.-M.3    MacDougal, J.M.4    McLaughlin, J.L.5
  • 108
    • 33750295898 scopus 로고    scopus 로고
    • Total synthesis of (+)- cis -sylvaticin: Double oxidative cyclization reactions catalyzed by osmium
    • Donohoe T J., Harris R M., Burrows J, Parker J. Total synthesis of (+)- cis -sylvaticin: double oxidative cyclization reactions catalyzed by osmium. J Am Chem Soc 2006 128 13704-13705
    • (2006) J Am Chem Soc , vol.128 , pp. 13704-13705
    • Donohoe, T.J.1    Harris, R.M.2    Burrows, J.3    Parker, J.4
  • 109
    • 0025335437 scopus 로고
    • Gigantecin: A novel antimitotic and cytotoxic acetogenin, with nonadjacent tetrahydrofuran rings, from Goniothalamus giganteus (Annonaceae)
    • Alkofahi A, Rupprecht J K., Liu Y M., Chang C J., Smith D L., McLaughlin J L. Gigantecin: a novel antimitotic and cytotoxic acetogenin, with nonadjacent tetrahydrofuran rings, from Goniothalamus giganteus (Annonaceae). Experientia 1990 46 539-541
    • (1990) Experientia , vol.46 , pp. 539-541
    • Alkofahi, A.1    Rupprecht, J.K.2    Liu, Y.M.3    Chang, C.J.4    Smith, D.L.5    McLaughlin, J.L.6
  • 110
    • 33746918324 scopus 로고    scopus 로고
    • Sequencing of three-component olefin metatheses: Total synthesis of either (+)-gigantecin or (+)-14-deoxy-9-oxygigantecin
    • Hoye T R., Eklov B M., Jeon J, Khoroosi M. Sequencing of three-component olefin metatheses: total synthesis of either (+)-gigantecin or (+)-14-deoxy-9-oxygigantecin. Org Lett 2006 8 3383-3386
    • (2006) Org Lett , vol.8 , pp. 3383-3386
    • Hoye, T.R.1    Eklov, B.M.2    Jeon, J.3    Khoroosi, M.4
  • 111
    • 0031976790 scopus 로고    scopus 로고
    • Jimenezin, a novel Annonaceous acetogenin from the seeds of Rollinia mucosa containing adjacent tetrahydrofuran-tetrahydropyran ring systems
    • Chavez D, Acevedo L A., Mata R. Jimenezin, a novel Annonaceous acetogenin from the seeds of Rollinia mucosa containing adjacent tetrahydrofuran- tetrahydropyran ring systems. J Nat Prod 1998 61 419-421
    • (1998) J Nat Prod , vol.61 , pp. 419-421
    • Chavez, D.1    Acevedo, L.A.2    Mata, R.3
  • 112
    • 33748618972 scopus 로고    scopus 로고
    • Total synthesis of jimenezin via an intramolecular allylboration
    • Bandur N G., Bruckner D, Hoffmann R W., Koert U. Total synthesis of jimenezin via an intramolecular allylboration. Org Lett 2006 8 3829-3831
    • (2006) Org Lett , vol.8 , pp. 3829-3831
    • Bandur, N.G.1    Bruckner, D.2    Hoffmann, R.W.3    Koert, U.4
  • 114
  • 115
    • 0032575217 scopus 로고    scopus 로고
    • Unusual bioactive Annonaceous acetogenins from Goniothalamus giganteus
    • Alali F Q., Rogers L, Zhang Y, McLaughlin J L. Unusual bioactive Annonaceous acetogenins from Goniothalamus giganteus. Tetrahedron 1998 54 5833-5844
    • (1998) Tetrahedron , vol.54 , pp. 5833-5844
    • Alali, F.Q.1    Rogers, L.2    Zhang, Y.3    McLaughlin, J.L.4
  • 116
    • 13444249837 scopus 로고    scopus 로고
    • Total synthesis of pyranicin
    • Strand D, Rein T. Total synthesis of pyranicin. Org Lett 2004 7 199-202
    • (2004) Org Lett , vol.7 , pp. 199-202
    • Strand, D.1    Rein, T.2
  • 117
    • 29844439833 scopus 로고    scopus 로고
    • Synthesis of pyragonicin
    • Strand D, Rein T. Synthesis of pyragonicin. Org Lett 2005 7 2779-2781
    • (2005) Org Lett , vol.7 , pp. 2779-2781
    • Strand, D.1    Rein, T.2
  • 118
    • 29844435482 scopus 로고    scopus 로고
    • Total synthesis of the proposed structure for pyragonicin
    • Takahashi S, Ogawa N, Koshino H, Nakata T. Total synthesis of the proposed structure for pyragonicin. Org Lett 2005 7 2783-2786
    • (2005) Org Lett , vol.7 , pp. 2783-2786
    • Takahashi, S.1    Ogawa, N.2    Koshino, H.3    Nakata, T.4
  • 120
    • 33644974479 scopus 로고    scopus 로고
    • Synthesis of (4 R,15 R,16 R,21 S)- and (4 R,15 S,16 S,21 S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I
    • Makabe H, Kimura Y, Higuchi M, Konno H, Murai M, Miyoshi H. Synthesis of (4 R,15 R,16 R,21 S)- and (4 R,15 S,16 S,21 S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I. Bioorg Med Chem 2006 14 3119-3130
    • (2006) Bioorg Med Chem , vol.14 , pp. 3119-3130
    • Makabe, H.1    Kimura, Y.2    Higuchi, M.3    Konno, H.4    Murai, M.5    Miyoshi, H.6
  • 121
    • 0034674356 scopus 로고    scopus 로고
    • Natural-product hybrids: Design, synthesis, and biological evaluation of quinone-Annonaceous acetogenins
    • Hoppen S, Emde U, Friedrich T, Grubert L, Koert U. Natural-product hybrids: design, synthesis, and biological evaluation of quinone-Annonaceous acetogenins. Angew Chem Int Ed Engl 2000 39 2099-2102
    • (2000) Angew Chem Int Ed Engl , vol.39 , pp. 2099-2102
    • Hoppen, S.1    Emde, U.2    Friedrich, T.3    Grubert, L.4    Koert, U.5
  • 122
    • 0035793850 scopus 로고    scopus 로고
    • Quinone-Annonaceous acetogenins: Synthesis and complex i inhibition studies of a new class of natural product hybrids
    • Arndt S, Emde U, Baurle S, Friedrich T, Grubert L, Koert U. Quinone-Annonaceous acetogenins: synthesis and complex I inhibition studies of a new class of natural product hybrids. Chem Eur J 2001 7 993-1005
    • (2001) Chem Eur J , vol.7 , pp. 993-1005
    • Arndt, S.1    Emde, U.2    Baurle, S.3    Friedrich, T.4    Grubert, L.5    Koert, U.6
  • 123
    • 0038487844 scopus 로고    scopus 로고
    • Semisynthesis of heterocyclic analogues of squamocin, a cytotoxic annonaceous acetogenin, by an unusual oxidative decarboxylation reaction
    • Duval R, Lewin G, Hocquemiller R. Semisynthesis of heterocyclic analogues of squamocin, a cytotoxic annonaceous acetogenin, by an unusual oxidative decarboxylation reaction. Bioorg Med Chem 2003 11 3439-3446
    • (2003) Bioorg Med Chem , vol.11 , pp. 3439-3446
    • Duval, R.1    Lewin, G.2    Hocquemiller, R.3
  • 124
    • 33644507467 scopus 로고    scopus 로고
    • Heterocyclic analogues of squamocin as inhibitors of mitochondrial complex I. On the role of the terminal lactone of Annonaceous acetogenins
    • Duval R A., Lewin G, Peris E, Chahboune N, Garofano A, Droese S, Cortes D, Brandt U, Hocquemiller R. Heterocyclic analogues of squamocin as inhibitors of mitochondrial complex I. On the role of the terminal lactone of Annonaceous acetogenins. Biochemistry 2006 45 2721-2728
    • (2006) Biochemistry , vol.45 , pp. 2721-2728
    • Duval, R.A.1    Lewin, G.2    Peris, E.3    Chahboune, N.4    Garofano, A.5    Droese, S.6    Cortes, D.7    Brandt, U.8    Hocquemiller, R.9
  • 125
    • 33646817110 scopus 로고    scopus 로고
    • Analogues of cytotoxic squamocin using reliable reactions: New insights into the reactivity and role of the , -unsaturated lactone of the Annonaceous acetogenins
    • Duval R A., Poupon E, Romero V, Peris E, Lewin G, Cortes D, Brandt U, Hocquemiller R. Analogues of cytotoxic squamocin using reliable reactions: new insights into the reactivity and role of the, -unsaturated lactone of the Annonaceous acetogenins. Tetrahedron 2006 62 6248-6257
    • (2006) Tetrahedron , vol.62 , pp. 6248-6257
    • Duval, R.A.1    Poupon, E.2    Romero, V.3    Peris, E.4    Lewin, G.5    Cortes, D.6    Brandt, U.7    Hocquemiller, R.8
  • 126
    • 39849093730 scopus 로고    scopus 로고
    • Synthesis of hybrid acetogenins, , -unsaturated- -lactone-free nitrogen-containing heterocyclic analogues, and their cytotoxicity against human cancer cell lines
    • Kojima N, Fushimi T, Maezaki N, Tanaka T, Yamori T. Synthesis of hybrid acetogenins,, -unsaturated- -lactone-free nitrogen-containing heterocyclic analogues, and their cytotoxicity against human cancer cell lines. Bioorg Med Chem Lett 2008 18 1637-1641
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 1637-1641
    • Kojima, N.1    Fushimi, T.2    Maezaki, N.3    Tanaka, T.4    Yamori, T.5
  • 127
    • 0034596013 scopus 로고    scopus 로고
    • Enantiopure simple analogues of Annonaceous acetogenins with remarkable selective cytotoxicity towards tumor cell lines
    • Zeng B B., Wu Y, Yu Q, Wu Y L., Li Y, Chen X G. Enantiopure simple analogues of Annonaceous acetogenins with remarkable selective cytotoxicity towards tumor cell lines. Angew Chem Int Ed 2000 39 1934-1937
    • (2000) Angew Chem Int Ed , vol.39 , pp. 1934-1937
    • Zeng, B.B.1    Wu, Y.2    Yu, Q.3    Wu, Y.L.4    Li, Y.5    Chen, X.G.6
  • 129
    • 0033932923 scopus 로고    scopus 로고
    • Polyether mimics of naturally occurring cytotoxic Annonaceous acetogenins
    • Yao Z J., Wu H P., Wu Y L. Polyether mimics of naturally occurring cytotoxic Annonaceous acetogenins. J Med Chem 2000 43 2484-2487
    • (2000) J Med Chem , vol.43 , pp. 2484-2487
    • Yao, Z.J.1    Wu, H.P.2    Wu, Y.L.3
  • 130
    • 0037123425 scopus 로고    scopus 로고
    • Mimicry of Annonaceous acetogenins: Enantioselective synthesis of a (4 R)-hydroxy analogue having potent antitumor activity
    • Jiang S, Liu Z H., Sheng G, Zeng B B., Cheng X G., Wu Y L., Yao Z J. Mimicry of Annonaceous acetogenins: enantioselective synthesis of a (4 R)-hydroxy analogue having potent antitumor activity. J Org Chem 2002 67 3404-3408
    • (2002) J Org Chem , vol.67 , pp. 3404-3408
    • Jiang, S.1    Liu, Z.H.2    Sheng, G.3    Zeng, B.B.4    Cheng, X.G.5    Wu, Y.L.6    Yao, Z.J.7
  • 131
    • 0037415097 scopus 로고    scopus 로고
    • Studies on mimicry of naturally occurring Annonaceous acetogenins: Non-THF analogues leading to remarkable selective cytotoxicity against human tumor cells
    • Zeng B B., Wu Y, Jiang S, Yu Q, Yao Z J., Liu Z H., Li H Y., Li Y, Chen X G., Wu Y L. Studies on mimicry of naturally occurring Annonaceous acetogenins: non-THF analogues leading to remarkable selective cytotoxicity against human tumor cells. Chem Eur J 2003 9 282-290
    • (2003) Chem Eur J , vol.9 , pp. 282-290
    • Zeng, B.B.1    Wu, Y.2    Jiang, S.3    Yu, Q.4    Yao, Z.J.5    Liu, Z.H.6    Li, H.Y.7    Li, Y.8    Chen, X.G.9    Wu, Y.L.10
  • 134
    • 34249289008 scopus 로고    scopus 로고
    • Annonaceous acetogenin mimics bearing a terminal lactam and their cytotoxicity against cancer cells
    • Liu H X., Huang G R., Zhang H M., Wu J R., Yao Z J. Annonaceous acetogenin mimics bearing a terminal lactam and their cytotoxicity against cancer cells. Bioorg Med Chem Lett 2007 17 3426-3430
    • (2007) Bioorg Med Chem Lett , vol.17 , pp. 3426-3430
    • Liu, H.X.1    Huang, G.R.2    Zhang, H.M.3    Wu, J.R.4    Yao, Z.J.5
  • 135
    • 53849120600 scopus 로고    scopus 로고
    • Tuning the acyclic ether moiety of anticancer agent AA005 with conformationally constrained fragments
    • Liu H X., Shao F, Li G Q., Xun G L., Yao Z J. Tuning the acyclic ether moiety of anticancer agent AA005 with conformationally constrained fragments. Chem Eur J 2008 14 8632-8639
    • (2008) Chem Eur J , vol.14 , pp. 8632-8639
    • Liu, H.X.1    Shao, F.2    Li, G.Q.3    Xun, G.L.4    Yao, Z.J.5
  • 136
    • 0029956428 scopus 로고    scopus 로고
    • Chlorinated Annonaceous acetogenins and their bioactivities
    • Ye Q, Shi G, He K, McLaughlin J L. Chlorinated Annonaceous acetogenins and their bioactivities. J Nat Prod 1996 59 994-996
    • (1996) J Nat Prod , vol.59 , pp. 994-996
    • Ye, Q.1    Shi, G.2    He, K.3    McLaughlin, J.L.4
  • 137
    • 56249092057 scopus 로고    scopus 로고
    • Synthesis of C4-fluorinated solamins and their growth inhibitory activity against human cancer cell lines
    • Kojima N, Hayashi H, Suzuki S, Tominaga H, Maezaki N, Tanaka T, Yamori T. Synthesis of C4-fluorinated solamins and their growth inhibitory activity against human cancer cell lines. Bioorg Med Chem Lett 2008 18 6451-6453
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 6451-6453
    • Kojima, N.1    Hayashi, H.2    Suzuki, S.3    Tominaga, H.4    Maezaki, N.5    Tanaka, T.6    Yamori, T.7
  • 138
    • 0031720358 scopus 로고    scopus 로고
    • 10-Oximeguanacone, the first nitrogenated acetogenin derivative found to be a potent inhibitor of mitochondrial complex I
    • Gallardo T, Saez J, Granados H, Tormo J R., Velez I D., Brun N, Torres B, Cortes D. 10-Oximeguanacone, the first nitrogenated acetogenin derivative found to be a potent inhibitor of mitochondrial complex I. J Nat Prod 1998 61 1001-1005
    • (1998) J Nat Prod , vol.61 , pp. 1001-1005
    • Gallardo, T.1    Saez, J.2    Granados, H.3    Tormo, J.R.4    Velez, I.D.5    Brun, N.6    Torres, B.7    Cortes, D.8
  • 139
    • 0032836893 scopus 로고    scopus 로고
    • Semisynthesis and cytotoxicity of amino acetogenins and derivatives
    • Duret P, Hocquemiller R, Gantier J C., Figadere B. Semisynthesis and cytotoxicity of amino acetogenins and derivatives. Bioorg Med Chem 1999 7 1821-1826
    • (1999) Bioorg Med Chem , vol.7 , pp. 1821-1826
    • Duret, P.1    Hocquemiller, R.2    Gantier, J.C.3    Figadere, B.4
  • 140
    • 20444448544 scopus 로고    scopus 로고
    • Annonaceous acetogenins: The hydroxyl groups and THF rings are crucial structural elements for targeting the mitochondria, demonstration with the synthesis of fluorescent squamocin analogues
    • Derbre S, Roue G, Poupon E, Susin Santos A, Hocquemiller R. Annonaceous acetogenins: the hydroxyl groups and THF rings are crucial structural elements for targeting the mitochondria, demonstration with the synthesis of fluorescent squamocin analogues. Chembiochem 2005 6 979-982
    • (2005) Chembiochem , vol.6 , pp. 979-982
    • Derbre, S.1    Roue, G.2    Poupon, E.3    Susin Santos, A.4    Hocquemiller, R.5
  • 144
    • 33846908306 scopus 로고    scopus 로고
    • A structure-activity guided strategy for fluorescent labeling of Annonaceous acetogenin mimetics and their application in cell biology
    • Liu H X., Huang G R., Zhang H M., Jiang S, Wu J R., Yao Z J. A structure-activity guided strategy for fluorescent labeling of Annonaceous acetogenin mimetics and their application in cell biology. Chembiochem 2007 8 172-177
    • (2007) Chembiochem , vol.8 , pp. 172-177
    • Liu, H.X.1    Huang, G.R.2    Zhang, H.M.3    Jiang, S.4    Wu, J.R.5    Yao, Z.J.6
  • 146
    • 0028302733 scopus 로고
    • Novel calcium ionophores: Supramolecular complexation by the hydroxylated-bistetrahydrofuran skeleton of potent antitumor annocnaceous acetogenins
    • Sasaki S, Naito H, Maruta K, Kawahara E, Maeda M. Novel calcium ionophores: supramolecular complexation by the hydroxylated-bistetrahydrofuran skeleton of potent antitumor annocnaceous acetogenins. Tetrahedron Lett 1994 35 3337-3340
    • (1994) Tetrahedron Lett , vol.35 , pp. 3337-3340
    • Sasaki, S.1    Naito, H.2    Maruta, K.3    Kawahara, E.4    Maeda, M.5
  • 147
    • 0000028244 scopus 로고
    • Structural elucidation of tetrahydrofuranic acetogenins by means of precursor-ion scanning method
    • Araya H, Fujimoto Y, Hirayama K. Structural elucidation of tetrahydrofuranic acetogenins by means of precursor-ion scanning method. Yuki Gosei Kagaku Kyokaishi 1994 52 765-777
    • (1994) Yuki Gosei Kagaku Kyokaishi , vol.52 , pp. 765-777
    • Araya, H.1    Fujimoto, Y.2    Hirayama, K.3
  • 148
    • 85047674144 scopus 로고
    • New calcium-selective electrodes based on Annonaceous acetogenins and their analogs with neighboring bistetrahydrofuran
    • Sasaki S, Maruta K, Naito H, Sugihara H, Hiratani K, Maeda M. New calcium-selective electrodes based on Annonaceous acetogenins and their analogs with neighboring bistetrahydrofuran. Tetrahedron Lett 1995 36 5571-5574
    • (1995) Tetrahedron Lett , vol.36 , pp. 5571-5574
    • Sasaki, S.1    Maruta, K.2    Naito, H.3    Sugihara, H.4    Hiratani, K.5    Maeda, M.6
  • 149
    • 0032510264 scopus 로고    scopus 로고
    • Novel acyclic ligands for metal cations based on the adjacent bistetrahydrofuran as analogs of natural Annonaceous acetogenins
    • Sasaki S, Maruta K, Naito H, Maemura R, Kawahara E, Maeda M. Novel acyclic ligands for metal cations based on the adjacent bistetrahydrofuran as analogs of natural Annonaceous acetogenins. Tetrahedron 1998 54 2401-2410
    • (1998) Tetrahedron , vol.54 , pp. 2401-2410
    • Sasaki, S.1    Maruta, K.2    Naito, H.3    Maemura, R.4    Kawahara, E.5    Maeda, M.6
  • 152
    • 45249110232 scopus 로고    scopus 로고
    • Mono-tetrahydrofuran Annonaceous acetogenins from Annona squamosa as cytotoxic agents and calcium ion chelators
    • Liaw C C., Yang Y L., Chen M, Chang F R., Chen S L., Wu S H., Wu Y C. Mono-tetrahydrofuran Annonaceous acetogenins from Annona squamosa as cytotoxic agents and calcium ion chelators. J Nat Prod 2008 71 764-771
    • (2008) J Nat Prod , vol.71 , pp. 764-771
    • Liaw, C.C.1    Yang, Y.L.2    Chen, M.3    Chang, F.R.4    Chen, S.L.5    Wu, S.H.6    Wu, Y.C.7
  • 153
    • 0032904575 scopus 로고    scopus 로고
    • Quantitative evaluation of Annonaceous acetogenins in monthly samples of paw paw (Asimina triloba) twigs by liquid chromatography/electrospray ionization/tandem mass spectrometry
    • Gu Z M., Zhou D, Lewis N J., Wu J, Johnson H A., McLaughlin J L., Gordon J. Quantitative evaluation of Annonaceous acetogenins in monthly samples of paw paw (Asimina triloba) twigs by liquid chromatography/electrospray ionization/tandem mass spectrometry. Phytochem Anal 1999 10 32-38
    • (1999) Phytochem Anal , vol.10 , pp. 32-38
    • Gu, Z.M.1    Zhou, D.2    Lewis, N.J.3    Wu, J.4    Johnson, H.A.5    McLaughlin, J.L.6    Gordon, J.7
  • 154
    • 49049098686 scopus 로고    scopus 로고
    • Paw paw and cancer: Annonaceous acetogenins from discovery to commercial products
    • McLaughlin J L. Paw paw and cancer: Annonaceous acetogenins from discovery to commercial products. J Nat Prod 2008 71 1311-1321
    • (2008) J Nat Prod , vol.71 , pp. 1311-1321
    • McLaughlin, J.L.1
  • 155
    • 38849200278 scopus 로고    scopus 로고
    • Dietary administration of Asimina triloba (Paw Paw) extract increases tumor latency in N -methyl- N -nitrosourea-treated rats
    • Cuendet M, Oteham C P., Moon R C., Keller W J., Peaden P A., Pezzuto J M. Dietary administration of Asimina triloba (Paw Paw) extract increases tumor latency in N -methyl- N -nitrosourea-treated rats. Pharm Biol 2008 46 3-7
    • (2008) Pharm Biol , vol.46 , pp. 3-7
    • Cuendet, M.1    Oteham, C.P.2    Moon, R.C.3    Keller, W.J.4    Peaden, P.A.5    Pezzuto, J.M.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.