메뉴 건너뛰기




Volumn 70, Issue 9, 2009, Pages 1182-1186

Four tetracyclic oxindole alkaloids and a taberpsychine derivative from a Malayan Tabernaemontana

Author keywords

NMR; Oxindole alkaloids; Plants; Tabernaemontana

Indexed keywords

INDOLE ALKALOID; INDOLE DERIVATIVE; N(4) DEMETHYLTABERPSYCHINE; N(4)-DEMETHYLTABERPSYCHINE; OXINDOLE;

EID: 68549085255     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2009.06.010     Document Type: Article
Times cited : (22)

References (40)
  • 1
    • 0002930061 scopus 로고
    • Catharinensine, an oxidole alkaloid from Peschiera catharinensis
    • Araujo A.R., Kascheres C., Fujiwara F., and Marsaioli A.J. Catharinensine, an oxidole alkaloid from Peschiera catharinensis. Phytochemistry 23 (1984) 2359-2363
    • (1984) Phytochemistry , vol.23 , pp. 2359-2363
    • Araujo, A.R.1    Kascheres, C.2    Fujiwara, F.3    Marsaioli, A.J.4
  • 3
    • 77957037558 scopus 로고
    • Oxindole alkaloids
    • Manske R.H.F. (Ed), Academic Press, New York (Chapter 2)
    • Bindra J.S. Oxindole alkaloids. In: Manske R.H.F. (Ed). The Alkaloids vol. 14 (1973), Academic Press, New York 83-121 (Chapter 2)
    • (1973) The Alkaloids , vol.14 , pp. 83-121
    • Bindra, J.S.1
  • 4
    • 0001305405 scopus 로고
    • Carbon-13 nuclear magnetic resonance in alkaloid chemistry
    • Broadbent T.A., and Paul E.G. Carbon-13 nuclear magnetic resonance in alkaloid chemistry. Heterocycles 20 (1983) 863-980
    • (1983) Heterocycles , vol.20 , pp. 863-980
    • Broadbent, T.A.1    Paul, E.G.2
  • 5
    • 84944387897 scopus 로고
    • Alkaloids from Tabernaemontana
    • Brossi A. (Ed), Academic Press, Orlando (Chapter 1)
    • Danieli B., and Palmisano G. Alkaloids from Tabernaemontana. In: Brossi A. (Ed). The Alkaloids vol. 27 (1986), Academic Press, Orlando 1-130 (Chapter 1)
    • (1986) The Alkaloids , vol.27 , pp. 1-130
    • Danieli, B.1    Palmisano, G.2
  • 6
    • 0019958311 scopus 로고
    • Monomeric indole alkaloids from Ervatamia hainannensis
    • Feng X.Z., Kan C., Potier P., Kan S.W., and Lounasmaa M. Monomeric indole alkaloids from Ervatamia hainannensis. Planta Med. 44 (1982) 212-214
    • (1982) Planta Med. , vol.44 , pp. 212-214
    • Feng, X.Z.1    Kan, C.2    Potier, P.3    Kan, S.W.4    Lounasmaa, M.5
  • 8
    • 77957043453 scopus 로고    scopus 로고
    • Alkaloids from Malaysian flora
    • Pelletier S.W. (Ed), Pergamon, Amsterdam (Chapter 2)
    • Kam T.S. Alkaloids from Malaysian flora. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives vol. 14 (1999), Pergamon, Amsterdam 285-435 (Chapter 2)
    • (1999) Alkaloids: Chemical and Biological Perspectives , vol.14 , pp. 285-435
    • Kam, T.S.1
  • 9
    • 33749387172 scopus 로고    scopus 로고
    • Bisindole alkaloids
    • Cordell G.A. (Ed), Academic Press, Amsterdam (Chapter 4)
    • Kam T.S., and Choo Y.M. Bisindole alkaloids. In: Cordell G.A. (Ed). The Alkaloids: Chemistry and Biology vol. 63 (2006), Academic Press, Amsterdam 181-337 (Chapter 4)
    • (2006) The Alkaloids: Chemistry and Biology , vol.63 , pp. 181-337
    • Kam, T.S.1    Choo, Y.M.2
  • 10
    • 54849431780 scopus 로고    scopus 로고
    • Alkaloids of Kopsia
    • Cordell G.A. (Ed), Academic Press, Amsterdam (Chapter 1)
    • Kam T.S., and Lim K.H. Alkaloids of Kopsia. In: Cordell G.A. (Ed). The Alkaloids: Chemistry and Biology vol. 66 (2008), Academic Press, Amsterdam 1-111 (Chapter 1)
    • (2008) The Alkaloids: Chemistry and Biology , vol.66 , pp. 1-111
    • Kam, T.S.1    Lim, K.H.2
  • 11
    • 0035691855 scopus 로고    scopus 로고
    • Dippinines A-D, new iboga-derived indole alkaloids from Tabernaemontana
    • Kam T.S., and Sim K.M. Dippinines A-D, new iboga-derived indole alkaloids from Tabernaemontana. Heterocycles 55 (2001) 2405-2412
    • (2001) Heterocycles , vol.55 , pp. 2405-2412
    • Kam, T.S.1    Sim, K.M.2
  • 12
    • 0036098824 scopus 로고    scopus 로고
    • Five new iboga alkaloids from Tabernaemontana corymbosa
    • Kam T.S., and Sim K.M. Five new iboga alkaloids from Tabernaemontana corymbosa. J. Nat. Prod. 65 (2002) 669-672
    • (2002) J. Nat. Prod. , vol.65 , pp. 669-672
    • Kam, T.S.1    Sim, K.M.2
  • 13
    • 0036233988 scopus 로고    scopus 로고
    • Vobasonidine and vobatrcine, novel bisindole alkaloids from a Malayan Tabernaemontana
    • Kam T.S., and Sim K.M. Vobasonidine and vobatrcine, novel bisindole alkaloids from a Malayan Tabernaemontana. Helv. Chim. Acta 85 (2002) 1027-1032
    • (2002) Helv. Chim. Acta , vol.85 , pp. 1027-1032
    • Kam, T.S.1    Sim, K.M.2
  • 14
    • 0036843336 scopus 로고    scopus 로고
    • New tabernamine derivatives from Tabernaemontana
    • Kam T.S., and Sim K.M. New tabernamine derivatives from Tabernaemontana. Heterocycles 57 (2002) 2137-2143
    • (2002) Heterocycles , vol.57 , pp. 2137-2143
    • Kam, T.S.1    Sim, K.M.2
  • 15
    • 0038340933 scopus 로고    scopus 로고
    • Conodurine, conoduramine, and ervahanine derivatives from Tabernaemontana corymbosa
    • Kam T.S., and Sim K.M. Conodurine, conoduramine, and ervahanine derivatives from Tabernaemontana corymbosa. Phytochemistry 63 (2003) 625-629
    • (2003) Phytochemistry , vol.63 , pp. 625-629
    • Kam, T.S.1    Sim, K.M.2
  • 16
    • 0037286761 scopus 로고    scopus 로고
    • Conodirinines A and B, novel vobasine-iboga bisindoles incorporating an additional tetrahydro-1,3-oxazine unit on the vobasinyl moiety
    • Kam T.S., and Sim K.M. Conodirinines A and B, novel vobasine-iboga bisindoles incorporating an additional tetrahydro-1,3-oxazine unit on the vobasinyl moiety. Helv. Chim. Acta 86 (2003) 122-126
    • (2003) Helv. Chim. Acta , vol.86 , pp. 122-126
    • Kam, T.S.1    Sim, K.M.2
  • 17
    • 0000371004 scopus 로고
    • Plumeran alkaloids from Kopsia profunda
    • Kam T.S., and Tan P.S. Plumeran alkaloids from Kopsia profunda. Phytochemistry 29 (1990) 2321-2322
    • (1990) Phytochemistry , vol.29 , pp. 2321-2322
    • Kam, T.S.1    Tan, P.S.2
  • 18
    • 0032493421 scopus 로고    scopus 로고
    • Conodiparines A-D, new bisindoles from Tabernaemontana. Reversal of vincristine-resistance with cultured cells
    • Kam T.S., Sim K.M., Koyano T., Toyoshima M., Hayashi M., and Komiyama K. Conodiparines A-D, new bisindoles from Tabernaemontana. Reversal of vincristine-resistance with cultured cells. Bioorg. Med. Chem. Lett. 8 (1998) 1693-1696
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1693-1696
    • Kam, T.S.1    Sim, K.M.2    Koyano, T.3    Toyoshima, M.4    Hayashi, M.5    Komiyama, K.6
  • 19
    • 0033575506 scopus 로고    scopus 로고
    • Tronoharine, a novel hexacyclic indole alkaloid from a Malayan Tabernaemontana
    • Kam T.S., Sim K.M., and Lim T.M. Tronoharine, a novel hexacyclic indole alkaloid from a Malayan Tabernaemontana. Tetrahedron Lett. 40 (1999) 5409-5412
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5409-5412
    • Kam, T.S.1    Sim, K.M.2    Lim, T.M.3
  • 20
    • 0034620931 scopus 로고    scopus 로고
    • Tronocarpine, a novel pentacyclic indole incorporating a seven-membered lactam moiety
    • Kam T.S., Sim K.M., and Lim T.M. Tronocarpine, a novel pentacyclic indole incorporating a seven-membered lactam moiety. Tetrahedron Lett. 41 (2000) 2733-2736
    • (2000) Tetrahedron Lett. , vol.41 , pp. 2733-2736
    • Kam, T.S.1    Sim, K.M.2    Lim, T.M.3
  • 21
    • 0035833076 scopus 로고    scopus 로고
    • Voastrictine, a novel pentacyclic quinolinic alkaloid from Tabernaemontana
    • Kam T.S., Sim K.M., and Lim T.M. Voastrictine, a novel pentacyclic quinolinic alkaloid from Tabernaemontana. Tetrahedron Lett. 42 (2001) 4721-4723
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4721-4723
    • Kam, T.S.1    Sim, K.M.2    Lim, T.M.3
  • 22
    • 0037250073 scopus 로고    scopus 로고
    • New bisindole alkaloids from Tabernaemontana corymbosa
    • Kam T.S., Sim K.M., and Pang H.S. New bisindole alkaloids from Tabernaemontana corymbosa. J. Nat. Prod. 66 (2003) 11-16
    • (2003) J. Nat. Prod. , vol.66 , pp. 11-16
    • Kam, T.S.1    Sim, K.M.2    Pang, H.S.3
  • 24
    • 58049149727 scopus 로고    scopus 로고
    • Conolutinine, a hexacyclic indole alkaloid with a novel ring system incorporating a diazaspiro center and fused oxadiazepine-tetrahydrofuran rings
    • Lim K.H., and Kam T.S. Conolutinine, a hexacyclic indole alkaloid with a novel ring system incorporating a diazaspiro center and fused oxadiazepine-tetrahydrofuran rings. Tetrahedron Lett. 50 (2009) 752-754
    • (2009) Tetrahedron Lett. , vol.50 , pp. 752-754
    • Lim, K.H.1    Kam, T.S.2
  • 25
    • 65549124010 scopus 로고    scopus 로고
    • Conoliferine and isoconoliferine, structurally novel alkaloid-lignan conjugates from Tabernaemontana corymbosa
    • Lim K.H., and Kam T.S. Conoliferine and isoconoliferine, structurally novel alkaloid-lignan conjugates from Tabernaemontana corymbosa. Tetrahedron Lett. 50 (2009) 3756-3759
    • (2009) Tetrahedron Lett. , vol.50 , pp. 3756-3759
    • Lim, K.H.1    Kam, T.S.2
  • 26
    • 54149100129 scopus 로고    scopus 로고
    • Jerantinines A-G, cytotoxic Aspidosperma alkaloids from Tabernaemontana corymbosa
    • Lim K.H., Hiraku O., Komiyama K., and Kam T.S. Jerantinines A-G, cytotoxic Aspidosperma alkaloids from Tabernaemontana corymbosa. J. Nat. Prod. 71 (2008) 1591-1594
    • (2008) J. Nat. Prod. , vol.71 , pp. 1591-1594
    • Lim, K.H.1    Hiraku, O.2    Komiyama, K.3    Kam, T.S.4
  • 27
    • 62349083313 scopus 로고    scopus 로고
    • Seco-tabersonine alkaloids from Tabernaemontana corymbosa
    • Lim K.H., Thomas N.F., Abdullah Z., and Kam T.S. Seco-tabersonine alkaloids from Tabernaemontana corymbosa. Phytochemistry 70 (2009) 424-429
    • (2009) Phytochemistry , vol.70 , pp. 424-429
    • Lim, K.H.1    Thomas, N.F.2    Abdullah, Z.3    Kam, T.S.4
  • 28
    • 0001465425 scopus 로고
    • Oxindole alkaloids from Uncaria sinensis
    • Liu H.M., and Feng X.Z. Oxindole alkaloids from Uncaria sinensis. Phytochemistry 33 (1993) 707-710
    • (1993) Phytochemistry , vol.33 , pp. 707-710
    • Liu, H.M.1    Feng, X.Z.2
  • 29
    • 0027965813 scopus 로고
    • Preparation and conformational study of Z- and E-isositsirikine epimers and model compounds. Determination of their C-16 configurations
    • Lounasmaa M., Jokela R., Hanhinen P., Miettinen J., and Salo J. Preparation and conformational study of Z- and E-isositsirikine epimers and model compounds. Determination of their C-16 configurations. Tetrahedron 50 (1994) 9207-9222
    • (1994) Tetrahedron , vol.50 , pp. 9207-9222
    • Lounasmaa, M.1    Jokela, R.2    Hanhinen, P.3    Miettinen, J.4    Salo, J.5
  • 30
    • 33748537057 scopus 로고    scopus 로고
    • Heteroyohimbinoid type oxindole alkaloids from Mitragyna parvifolia
    • Pandey R., Singh S.C., and Gupta M.M. Heteroyohimbinoid type oxindole alkaloids from Mitragyna parvifolia. Phytochemistry 67 (2006) 2164-2169
    • (2006) Phytochemistry , vol.67 , pp. 2164-2169
    • Pandey, R.1    Singh, S.C.2    Gupta, M.M.3
  • 31
    • 0002648333 scopus 로고
    • neoreserpate, an isomer of methyl reserpate. Part 4. Infrared spectra and configuration at C-3
    • neoreserpate, an isomer of methyl reserpate. Part 4. Infrared spectra and configuration at C-3. Tetrahedron Lett. 2 (1961) 481-484
    • (1961) Tetrahedron Lett. , vol.2 , pp. 481-484
    • Rosen, W.E.1
  • 33
    • 0027738610 scopus 로고
    • A nuclear magnetic resonance study on the eleven stereoisomers of heteroyohimbine-type oxindole alkaloids
    • Seki H., Takayama H., Aimi N., Sakai S.I., and Ponglux D. A nuclear magnetic resonance study on the eleven stereoisomers of heteroyohimbine-type oxindole alkaloids. Chem. Pharm. Bull. 41 (1993) 2077-2086
    • (1993) Chem. Pharm. Bull. , vol.41 , pp. 2077-2086
    • Seki, H.1    Takayama, H.2    Aimi, N.3    Sakai, S.I.4    Ponglux, D.5
  • 37
    • 33745418501 scopus 로고
    • Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. Alkaloids
    • Wenkert E., Bindra J.S., Chang C.J., Cochran D.W., and Schell F.M. Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. Alkaloids. Acc. Chem. Res. 7 (1974) 46-51
    • (1974) Acc. Chem. Res. , vol.7 , pp. 46-51
    • Wenkert, E.1    Bindra, J.S.2    Chang, C.J.3    Cochran, D.W.4    Schell, F.M.5
  • 38
    • 0024513739 scopus 로고
    • Preparation and H(3) isomerization of C(15)-substituted deplacheine derivatives. Synthesis of geissoschizol and geissoschizine
    • Wenkert E., Guo M., Pestchanker M.J., Shi Y.J., and Vankar Y.D. Preparation and H(3) isomerization of C(15)-substituted deplacheine derivatives. Synthesis of geissoschizol and geissoschizine. J. Org. Chem. 54 (1989) 1166-1174
    • (1989) J. Org. Chem. , vol.54 , pp. 1166-1174
    • Wenkert, E.1    Guo, M.2    Pestchanker, M.J.3    Shi, Y.J.4    Vankar, Y.D.5
  • 39
    • 0033466715 scopus 로고    scopus 로고
    • Two new oxindole alkaloids from Ervatamia yunnanensis
    • Yu Y., Gao J.M., and Liu J.K. Two new oxindole alkaloids from Ervatamia yunnanensis. Chin. Chem. Lett. 10 (1999) 575-578
    • (1999) Chin. Chem. Lett. , vol.10 , pp. 575-578
    • Yu, Y.1    Gao, J.M.2    Liu, J.K.3
  • 40
    • 49049114068 scopus 로고    scopus 로고
    • Alkaloids from the leaves of Uncaria rhynchophylla and their inhibitory activity on NO production in lipopolysaccharide-activated microglia
    • Yuan D., Ma B., Wu C., Yang J., Zhang L., Liu S., Wu L., and Kano Y. Alkaloids from the leaves of Uncaria rhynchophylla and their inhibitory activity on NO production in lipopolysaccharide-activated microglia. J. Nat. Prod. 71 (2008) 1271-1274
    • (2008) J. Nat. Prod. , vol.71 , pp. 1271-1274
    • Yuan, D.1    Ma, B.2    Wu, C.3    Yang, J.4    Zhang, L.5    Liu, S.6    Wu, L.7    Kano, Y.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.