Abstract
According to their alkaloidal products species of the “new” genusTabernaemontana can be partly differentiated. This differentiation is in agreement with the “old” genera classification. From the chemotaxonomic point of view a subdivision of subfam.Plumerioideae of theApocynaceae is proposed.
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Abaul, J., Bourgeois, P., Philogène, É., Damak, M., Ahond, A., Poupat, C., Potier, P., 1984: Contribution á l'étude des Tabernaemontanées Américaines. 4. La déhydro-14 tétrastachyne, nouvel alcaloïde bis-indolique isolé deTabernaemontana citrifolia et dePeschiera echinata (Apocynacées). — Compt. Rend. Acad. Sci. Paris, ser. 2,298: 627–629.
Achenbach, H., Raffelsberger, B., 1980a: 19-Ethoxy-coronaridine, a novel alkaloid fromTabernaemontana glandulosa. — Phytochemistry19: 716–717.
—, —, 1980b: Alkaloide inTabernaemontana-Arten; 12. Untersuchung der Alkaloide vonTabernaemontana olivaceae. — Condylocarpin-N-oxid, ein neues Alkaloid ausT. olivacea. — Z. Naturforsch.35b: 885–891.
—, 1975: Accedin and N(a)-Methyl-epi-affinin, zwei neue Alkaloide ausTabernaemontana accedens. — Chem. Ber.108: 3842–3854.
—, —, 1976a: N-Demethyl-16-epi-accedin, ein neues Alkaloid ausTabernaemontana accedens. — Tetrahedron Lett.1976: 351–352.
—, —, 1976b: Über einige Bisindolalkaloide ausTabernaemontana accedens. — Chem. Ber.109: 3527–3536.
—, 1980: 19-Hydroxycoronaridin und 19-Hydroxyibogamin, zwei antibiotisch wirksame Alkaloide vom Ibogamin-Typ. — Phytochemistry19: 2185–2188.
—, —, —, 1982: Tabernulosin und 12-Demethoxytabernusolin, zwei neue Alkaloide vom Picrinin-Typ ausTabernaemontana glandulosa. — Liebigs Ann. Chem.1982: 830–844.
Aguilar-Santos, G., Santos, A. C., Joson, L. M., 1964: Alkaloids ofTabernaemontana pandacaqui Poir. Isolation of coronaridine. — J. Philippine Pharm. Assoc.50: 321–323.
Agwada, V. C., Morita, Y., Renner, U., Hesse, M., Schmid, H., 1975: Die Alkaloide vonGabunia eglandulosa Stapf. — Helv. Chim. Acta58: 1001–1016.
Andriantsiferana, M., Besselièvre, R., Riche, C., Husson, H.-P., 1977: Structure de l'ervitsine alcaloïdeα-acylidolique d'un type nouveau. — Tetrahedron Lett.30: 2587–2590.
—, 1979: Alcaloïdes dePandaca boiteaui (Apocynaceae). — Phytochemistry18: 911–912.
Araujo, A. R., Kascheres, C., Fujiwara, F., Marsaioli, A. J., 1984: Catharinensine, an oxindole alkaloid fromPeschiera catharinensis. — Phytochemistry23: 2359–2663.
Atta-ur-Rahman, Daulatabadi, N., 1983: The isolation and structure of hyderabadine, a new indole alkaloid fromErvatamia coronaria. — Z. Naturforsch.38b: 1310–1312.
—, —, —, 1984: The isolation and structure of lahoricine, a new indolenine alkaloid fromErvatamia coronaria. — Z. Naturforsch.39b: 1289–1291.
—, 1983: The isolation and structure of mehranine, a new indoline alkaloid fromErvatamia coronaria. — Z. Naturforsch.38b: 1700–1701.
—, —, —, 1985: Ervatinine, an indole alkaloid fromErvatamia coronaria. — Phytochemistry24: 2473–2474.
Bakana, P., Dommisse, R., Esmans, E., Fokkens, R. H., Pieters, L., Nibbering, N. M. M., Vlietinck, A. J., 1984: 2-Acylindole alkaloids from leaves ofPterotaberna inconspicua. — Planta Medica50: 331–334.
Beek, T. A. van, Lankhorst, P. P., Verpoorte, R., Svendsen, A. B., 1982: Tacamine, the first example of a new class of indole alkaloids. — Tetrahedron Lett.23: 4827–4830.
—, 1984a: Antimicrobially active alkaloids fromTabernaemontana pachysiphon. — Phytochemistry23: 1771–1778.
—, 1984b: Isolation and synthesis of vobparicine, a novel type dimeric indole alkaloid. — Tetrahedron Lett.25: 2057–2060.
—, —, —, 1984c: Alkaloids ofTabernaemontana eglandulosa. — Tetrahedron40: 737–748.
—, —, —, —, —, 1984d:Tabernaemontana L. (Apocynaceae): a review of its taxonomy, phytochemistry, ethnobotany and pharmacology. — J. Ethnopharmacology10: 1–156.
—, 1985a: Monogagaine, a novel dimeric indole alkaloid fromTabernaemontana chippii andTabernaemontana dichotoma. — Z. Naturforsch.40B: 693–701.
—, 1985b: Pseudovobparicine, a new dimeric indole alkaloid fromTabernaemontana divaricata. — Planta Medica51: 277–279.
—, —, —, 1985c: Antimicrobially active alkaloids fromTabernaemontana chippii. — J. Nat. Prod.48: 400–423.
Bellefon, M. de, Debray, M.-M., Le Men-Oliver, L., Le Men, J., 1975: Alcaloïdes duPandaca mocquerysii var.pendula. — Phytochemistry14: 1649–1652.
Bert, M., Baudouin, G., Tillequin, F., Koch, M., 1985: Pagicerine—a new indole alkaloid fromPagiantha cerifera (Pancher & Sébert)Markgraf (Apocynaceae). — Heterocycles23: 2505–2508.
Biswas, R. C., 1973: Alkaloids of apocynaceous plants. 3.Ervatamia sphaerocarpa (Tabernaemontana sphaerocarpa). — Sci. Cult.39: 259–262.
Bombardelli, E., Bonati, A., Gabetta, B., Martinelli, E. M., Mustich, G., Danieli, B., 1976: Structures of tabernaelegantines A—D and tabernaelegantinines A and B, new indole alkaloids fromTabernaemontana elegans. — J. Chem. Soc. Perkin1: 1432–1438.
Bruneton, J., Cavé, A., Moretti, C., 1979: Etude de deux espèces deTabernaemontana de la Guyane. — Fitoterapia3: 123–126.
—, —, —, —, —, 1976: The carbon-20 stereochemistry of pandoline and epipandoline. — Tetrahedron Lett.39: 3567–3570.
Bui, A.-M., Das, B. C., Potier, P., 1980: Étude chimiotaxonomique deHazunta modesta. — Phytochemistry19: 1473–1475.
—, 1977: Étude chimiotaxonomique de quelques espèces deHazunta. — Phytochemistry16: 703–706.
Burnell, R. H., Medina, J. D., 1971: Alkaloids ofTabernaemontana psychotrifolia H. B. K. — Canad. J. Chem.49: 307–316.
Cava, M. P., Mowdood, S. K., Beal, J. L., 1965a: Isovoacristine: a new iboga-type alkaloid fromTabernaemontana laurifolia. — Chem. Ind. (London)1965: 2064
—, 1965b: Gabunine: a natural dimeric indole derived from perivine. — Tetrahedron Lett.1965: 931–935.
—, 1968a: The alkaloids ofTabernaemontana riedelii andT. rigida. — J. Org. Chem.33: 1055–1059.
—, 1968b: The alkaloids ofTabernaemontana crassa. Crassanine, a new oxindole alkaloid. — J. Org. Chem.33: 3350–3352.
Chardon-Loriaux, I., Husson, H.-P., 1975: Alcaloïdes monomères et “dimére” dérivés de la (−)cleavamine isolés deCapuronetta elegans (Apocynacées). — Tetrahedron Lett.1975: 1845–1848.
—, 1978: Alcaloïdes minoritaires deCapuronetta elegans (Apocynaceae). — Phytochemistry17: 1605–1608.
Chaverri, C., Ciccio, J. F., 1980: Seed alkaloids ofTabernaemontana arborea (Apocynaceae). — Rev. Latinoamer. Quim.11: 64.
Cordell, G. A., Saxon, J. E., 1981: Bisindole alkaloids. — InManske, R. H. F., Rodrigo, R. G. A., (Eds.): The alkaloids, chemistry and physiology 20, pp. 1–295. — London, New York: Academic Press.
Damak, M., Ahond, A., Potier, P., 1980: Bonafousine et isobonafousine, alcaloïdes dimères deBonafousia tetrastachya (Humbolt, Bonpland & Kunth)Markgraf (Apocynacées). — Bull. Soc. Chim. France2: 490–495.
—, —, —, 1981: Contribution à l'étude des tabernaemontanées américaines. 2. Nouveaux alcaloïdes deBonafousia tetrastachya (Humboldt, Bonpland & Kunth)Markgraf (Apocynacées). — Bull. Soc. Chim. France2: 213–216.
—, 1976: Bis[hydroxy-11-coranaridinyl]-12, nouvel alcaloïde dimere de type ibogane: elucidation de la structure par RM13C. — Tetrahedron Lett.39: 3531–3534.
Das, B. C., Fellion, E., Plat, M., 1967: Alcaloïdes des graines duConopharyngia durissima Stapf. Isolement de coronaridine, tabersonine et hydroxyindolénine de la coronaridine. — Compt. Rend. Acad. Sci. Paris, sér. C,264: 1765–1767.
Dugan, J. J., Hesse, M., Renner, U., Schmid, H., 1969a: Indolalkaloide ausConopharyngia durissima Stapf. — Helv. Chim. Acta52: 701–707.
—, —, —, 1969b: Conoflorin. — Helv. Chim. Acta50: 60–67.
Fallen, M. E., 1986: Floral structure in theApocynaceae: Morphological, functional, and evolutionary aspects. — Bot. Jahrb. Syst.106: 245–286.
Feng, X.-Z, Kan, C., Husson, H.-P., Potier, P., 1981: Nouveaux alcaloïdes indoliques dimeres de type voacamine extraits d'Ervatamia hainanensis. — J. Nat. Prod.44: 670–675.
—, —, —, —, —, 1982: Monomeric indole alkaloids fromErvatamia hainanensis. — Planta Medica44: 212–214.
Ganzinger, D., Hesse, M., 1976: A chemotaxonomic study of the subfamilyPlumerioideae of theApocynaceae. — Lloydia39: 326–349.
Garnier, J., Croquelois, G., Kaminski, P., Lewin, G., Miet, C., Poisson, J., 1984a: Alkaloïdes deBonafousia macrocalyx. — J. Nat. Prod.47: 1055–1056.
—, 1984b: Terpenoides et alcaloïdes d'Anacampta angulata. — J. Nat. Prod.47: 191.
Ghorbel, N., Damak, M., Ahond, Philogène, E., Poupat, C., Potier, P., Jacquemin, H., 1981: Contribution à l'étude des tabernaemontanées Américaines. 4. Alcaloïdes dePeschiera echinata. — J. Nat. Prod.44: 717–721.
Gorman, M., Neuss, N., Cone, N. J., Deyrup, J. A., 1960: Alkaloids fromApocynaceae. 3. Alkaloids ofTabernaemontana andErvatamia. The structure of coronaridine, a new alkaloid related to ibogamine. — J. Amer. Chem. Soc.82: 1142–1145.
Govindachari, T. R., Joshi, B. S., Saksena, A. K., Sathe, S. S., Viswanathan, N., 1965: The structure of heyneanine. — Tetrahedron Lett.1965: 3873–3878.
Guise, G. B., Ritchie, E., Taylor, W. C., 1965: The structure and formation of voaluteine. — Austral. J. Chem.18: 1279–1286.
Gunasekara, S. P., Cordell, G. A., Farnsworth, N. R., 1980: Anticancer indole alkaloids ofErvatamia heyneana. — Phytochemistry19: 1213–1218.
Harmouche, A., Mehri, H., Koch, M., Rabaron, A., Plat, M., Sevenet, T., 1976: Plantes de Nouvelle-Calédonie 39. Alcaloïdes des feuilles dePagiantha cerifera Mgf. (Apocynacées). — Ann. Pharm. Franç.34: 31–35.
Henriques, A., Kan, S.-K., Lounasmaa, M., 1979: A 400 MHz1H NMR study of the dimeric indole alkaloid ervafoline. — Acta Chem. Scand.B 33: 775–776.
—, 1980: Determination of structures by1H NMR at 400 MHz: alkaloids ofStenosolen heterophyllus. — Acta Chem. Scand.B 34: 509–512.
—, 1982: New dimeric indole alkaloids fromStenosolen heterophyllus: structure determinations and synthetic approach. — J. Org. Chem.47: 803–811.
Hesse, M., 1968: Indolalkaloide in Tabellen, Ergänzungswerk Monographie. — Berlin, Heidelberg, New York: Springer.
Hoizey, M. J., Debray, M.-M., Le Men-Oliver, L., Le Men, J., 1974: Alcaloïdes duPandaca calcarea etPandaca debrayi. — Phytochemistry13: 1995–1996.
—, 1970: Chimiotaxonomie du genreTabernaemontana: étude des alcaloïdes de cinq espèces originaires de Madagascar. — Ann. Pharm. Franç.28: 127–133.
Hootele, C., Pecher, J., 1968: Indole alkaloids. 19-Oxoconopharyngine fromConopharyngia jollyana. — Chimia22: 245–246.
—, 1967: Indole alkaloids 3. The structure of jollyanine. — Bull. Soc. Chim. Belges76: 300–307.
Hwang, B., Weisbach, J. A., Douglas, B., Raffauf, R., Cava, M. P., Bessho, K., 1969: The alkaloids ofPeschiera lundii (DC.)Miers. Isolation and structure elucidation of voacristine pseudoindoxyl and iboxygaine hydroxyindolenine. — J. Org. Chem.34: 412–415.
Iglesias, R., Diatta, L., 1975: Apodine, a new alkaloid ofTabernaemontana species. — Rev. CENIC, Cienc. Fis.6: 141–146.
Kan, C., Husson, H.-P., Jacquemin, H., Kan, S.-K., Lounasmaa, M., 1980a: Determination de structures par RMN du1H à 400 MHz: alcaloïdes deTabernaemontana albiflora. — Tetrahedron Lett.21: 55–58.
—, —, —, —, 1980b: Determination de structures par RMN du1H a 400 MHz: quatre nouveaux alcaloïdes deTabernaemontana albiflora. — Tetrahedron Lett.21: 3363–3366.
—, —, —, —, 1981: Détermination de structures par RMN du1H à 400 MHz: albifloranine, un nouvel alcaloïde deTabernaemontana albiflora. — Planta Medica47: 72–74.
—, 1984: Alcaloïdes indoliques deStenosolen heterophyllus. Tabernamine et isotabernamine. — J. Nat. Prod.47: 478–481.
Kan-Fan, C., Massiot, G., Das, B. C., Potier, P., 1981: Structure analysis by carbon-13 nuclear magnetic resonance spectroscopy of pandicine, a novel bisindole alkaloid fromPandacastrum saccharatum Pichon. — J. Org. Chem.46: 1481–1483.
Kingston, D. G. I., Li, B. T., Ionescu, F., 1977: Plant anticancer agents. 3. Isolation of indole and bisindole alkaloids fromTabernaemontana holstii roots. — J. Pharm. Sci.66: 1135–1138.
—, 1978: Plant anticancer agents 5: new bisindole alkaloids fromTabernaemontana johnstonii stem bark. — J. Pharm. Sci.67: 249–251.
Kisakürek, M. V., Leeuwenberg, A. J. M., Hesse, M., 1983: A chemotaxonomic investigation of the plant families ofApocynaceae, Loganiaceae, andRubiaceae by their indole alkaloid content. — InPelletier, S. W., (Ed.): Alkaloids: chemical and biological perspectives 1, pp. 211–376. — New York: Wiley.
Knox, J. R., Slobbe, J., 1975: Indole alkaloids fromErvatamia orientalis. 1. Isolation of alkaloids and structural identification of two dimers. — Austral. J. Chem.28: 1813–1823.
Kutney, J. P., Perez, H., 1982: Studies on natural products from Cuban plants. Alkaloids fromTabernaemontana citrifolia. — Helv. Chim. Acta65: 2242–2250.
Kyburz, R., Schöpp, E., Hesse, M., 1984: Peduncularistin, Triabunnin und Aristolarin, drei neue Indolalkaloide ausAristotelia peduncularis (Labill.)Hook. F. — Helv. Chim. Acta67: 804–814.
Ladhar, F., Damak, M., Ahond, A., Poupat, C., Potier, P., Moretti, C., 1981: Contribution à l'étude des tabernaemontanées Américaines. 3. Alcaloïdes deAnartia cf.meyeri. — J. Nat. Prod.44: 459–465.
Lathuillière, P., Olivier, L., Lévy, J., Le Men, J., 1970: Sur les alcaloïdes d'Ervatamia pandacaqui Pichon (Tabernaemontana pandacaqui Poir.), Apocynacées. — Ann. Pharm. Franç.28: 57–62.
Le Men, J., Potier, P., Le Men-Oliver, L., Panas, J. M., Richard, B., Potron, C., 1974: Alcaloïdes duGabunia eglandulosa: eglandine et eglanduiosine. — Bull. Soc. Chim. France2: 1369–1372.
Le Men-Oliver, L., Richard, B., Le Men, J., 1974: Alcaloïdes des graines duPandaca retusa. — Phytochemistry13: 280–281.
Leeuwenberg, A. J. M., 1976: TheApocynaceae of Africa. 1:Tabernaemontana L. 1. Introductory remarks to a revision of the species represented in Africa. — Adansonia2: 383–392.
Lévy, M. C., Debray, M.-M., Le Men-Oliver, L., Le Men, J., 1975: Alcaloïdes duPandaca speciosa. — Phytochemistry14: 579–580.
Matos, F. J. A., Braz, F. R., Gottlieb, O. R., Machado, F. W. L., Madruga, M. I. L. M., 1976: 20-Epiheyneanine, an iboga alkaloid fromPeschiera affinis. — Phytochemistry15: 551–553.
Meyer, W. E., Coppola, J. A., Goldman, L., 1973: Alkaloid studies 8: isolation and characterization of alkaloids ofTabernaemontana heyneana Wall and antifertility properties of coronaridine. — J. Pharm. Sci.62: 1199–1201.
Miet, C., Poisson, J., 1977: Alkaloids of the seeds ofPagiantha macrocarpa. — Phytochemistry16: 153.
Morfaux, A. M., Mulamba, T., Richard, B., Delaude, C., Massiot, G., Le Men-Olivier, L., 1982: Alkaloids ofPterotaberna inconspicua. — Phytochemistry21: 1767–1769.
Niemann, C., Kessel, J. W., 1966: The isolation of rupicoline and montanine, two pseudoindoxyl alkaloids ofTabernaemontana rupicola Benth. — J. Org. Chem.31: 2265–2269.
Panas, J. M., Richard, B., Sigaut, C., Debray, M.-M., Le Men-Oliver, L., 1974: Alcaloïdes duPandaca ochrascens. — Phytochemistry13: 1969–1974.
—, —, —, —, —, —, —, —, —, 1975: Alcaloïdes duMuntafara sessilifolia. — Phytochemistry14: 1120–1122.
Patel, M. B., Miet, C., Poisson, J., 1967: Alcaloïdes de quelquesTabernaemontana africains. — Ann. Pharm. Franç.25: 379–384.
—, 1973: Alcaloïdes deTabernaemontana brachyantha. — Phytochemistry12: 451–456.
Perera, P., Beek, T. A. van, Verpoorte, R., 1983a: Dichomine, a novel type of iboga alkaloid. — Planta Medica49: 232–235.
—, —, —, —, —, 1983b: Tertiary indole alkaloids ofTabernaemontana dichotoma seeds. — Planta Medica49: 28–31.
—, 1984a: 16(S)-Hydroxy-16,22-dihydroapparicine, a new alkaloid from the leaves ofTabernaemontana dichotoma. — J. Nat. Prod.47: 835–838.
—, 1984b: Tertiary indole alkaloids from fruits ofTabernaemontana dichotoma. — Planta Medica50: 251–253.
—, —, —, —, 1985: Alkaloids of stem and rootbark ofTabernaemontana dichotoma. — Phytochemistry24: 2097–2104.
Petitfrere, N., Morfaux, A. M., Debray, M. M., Le Men-Oliver, L., Le Men, J., 1975: Alcaloïdes des feuilles duPandaca minutiflora. — Phytochemistry14: 1648–1649.
Potier, P., Bui, A.-M., Das, B. C., Le Men, J., Boiteau, P., 1968: Plantes malgaches. 2. — Étude des alcaloïdes deHazunta velutina Pichon (Apocynacées). — Ann. Pharm. Franç.26: 621–629.
Quirin, F., Debray, M.-M., Sigaut, C., Thepenier, P., Le Men-Oliver, L., Le Men, J., 1975: Alcaloïdes duPandaca eusepala. — Phytochemistry14: 812–813.
Raj, K., Shoeb, A., Kapil, R. S., Popli, S. P., 1974: Alkaloids ofTabernaemontana divaricata. — Phytochemistry13: 1621–1622.
Rao, P. G., Singri, B. P., 1979: A rare alkaloid fromTabernaemontana heyneana Wall. — Indian J. Chem.17B: 414–415.
Rastogi, K., Kapil, R. S., Popli, S. P., 1980: New alkaloids fromTabernaemontana divaricata. — Phytochemistry19: 1209–1212.
Renner, U., Fritz, H., 1964: Isomere des Voacamins: Voacamidin, Conodurin und Conoduramin. — Tetrahedron Lett.1964: 283–287.
Ros, H.-P., Schöpp, E., Hesse, M., 1978: Indolalkaloide aus den Blättern vonPagiantha cerifera Markgraf. — Z. Naturforsch.33c: 290.
Schnoes, H. K., Thomas, D. W., Aksornvitaya, R., Schleigh, W. R., Kupchan, S. M., 1968: The isolation and structural elucidation of voacristine hydroxyindolenine. — J. Org. Chem.33: 1225–1227.
Talapatra, B., Patra, A., Talapatra, S. K., 1975: Terpenoids and alkaloids of the leaves ofTabernaemontana coronaria. — Phytochemistry14: 1652–1653.
Urrea, M., Ahond, A., Bui, A.-M., Potier, P., 1981: Nouveaux alcaloïdes indoliques dimères isolés deHazunta (Apocynacées). — Bull. Soc. Chim. France2: 147–149.
Vecchietti, V., Ferrari, G., Orsini, F., Pelizzoni, F., Zajotti, A., 1978: Alkaloids ofHazunta modesta. — Phytochemistry17: 835–836.
Voticky, Z., Jahodar, L., Cava, M. P., 1977: Alkaloids fromPeschiera laeta Mart. — Coll. Czech. Chem. Commun.42: 1403–1406.
Weisbach, J. A., Raffauf, R. F., Ribeiro, O., Macko, E., Douglas, B., 1963: Problems in chemotaxonomy 1: alkaloids ofPeschiera affinis. — J. Pharm. Sci.52: 350–353.
Yuldashev, P. K., Ubaev, U., Kuchenkova, M. A., Yunusov, S. Y., 1965: Structure of vincanidine and vinervine. — Khim. Prir. Soedin.1: 34–42.
Zeches, M., Debray, M.-M., Ledouble, G., Le Men-Olivier, L., Le Men, J., 1975: Alcaloïdes duPandaca caducifolia. — Phytochemistry14: 1122–1124.
Zhu, J., 1988: Chemie von Sperminalkaloiden — Chemotaxonomie der Indolalkaloide. — Thesis, Universität Zürich.
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Zhu, J.P., Guggisberg, A., Kalt-Hadamowsky, M. et al. Chemotaxonomic study of the genusTabernaemontana (Apocynaceae) based on their indole alkaloid content. Pl Syst Evol 172, 13–34 (1990). https://doi.org/10.1007/BF00937795
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DOI: https://doi.org/10.1007/BF00937795