Distribution of alkaloids in woody plants
DOI:
https://doi.org/10.14719/pst.2017.4.3.320Keywords:
Alkaloid, plant secondary metabolism, woody plant, natural products, trees, shrubs, specialized metabolitesAbstract
Alkaloids are nitrogen-containing compounds found in plants. Most are highly valued for their role in wide array of ailments such as anti-malarial, anti-cancerous, analgesics, and many more. In lights of tremendous interest in recent years on the chemistry and pharmacological properties of alkaloids, comprehensive data have been collected. Forest industries have recently started to develop sustainable ways to increase the value of its residues including the extraction and commercialization of high-valued plant natural compounds such as alkaloids. This review presents the distribution of alkaloids among woody plants (trees and shrubs).
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References
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2. Wink M. Biochemistry of plant secondary metabolism. Annual plant reviews. 2010;40.
3. Dewick PM. Medicinal natural products: a biosynthetic approach. 3rd ed: John Wiley and Sons Ltd; 2009. 539 p. https://doi.org/10.1002/9780470742761
4. Desgagne-Penix I, Farrow SC, Cram D, Nowak J, Facchini PJ. Integration of deep transcript and targeted metabolite profiles for eight cultivars of opium poppy. Plant Mol Biol. 2012;79(3):295-313. https://doi.org/10.1007/s11103-012-9913-2
5. Isah T. Anticancer Alkaloids from Trees: Development into Drugs. Pharmacogn Rev. 2016;10(20):90-9. https://doi.org/10.4103/0973-7847.194047
6. Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. Journal of the American Chemical Society. 1971;93(9):2325-7. https://doi.org/10.1021/ja00738a045
7. Ashihara H, Sano H, Crozier A. Caffeine and related purine alkaloids: Biosynthesis, catabolism, function and genetic engineering. Phytochemistry. 2008;69(4):841-56. https://doi.org/10.1016/j.phytochem.2007.10.029
8. Koyama Y, Tomoda Y, Kato M, Ashihara H. Metabolism of purine bases, nucleosides and alkaloids in theobromine-forming Theobroma cacao leaves. Plant Physiology and Biochemistry. 2003;41(11–12):977-84. https://doi.org/10.1016/j.plaphy.2003.07.002
9. Niemenak N, Onomo PE, Fotso, Lieberei R, Ndoumou DO. Purine alkaloids and phenolic compounds in three Cola species and Garcinia kola grown in Cameroon. South African Journal of Botany. 2008;74(4):629-38. https://doi.org/10.1016/j.sajb.2008.03.003
10. Epifano F, Fiorito S, Genovese S. Phytochemistry and pharmacognosy of the genus Acronychia. Phytochemistry. 2013;95:12-8. https://doi.org/10.1016/j.phytochem.2013.07.013
11. Tillequin F. Alkaloids in the genus Sarcomelicope. Recent Research Develop Phytochemistry. 1997;1:675–87.
12. Moore JM, Moore JF, Fodor G, Jones AB. Detection and Characterization of Cocaine and Related Tropane Alkaloids in Coca Leaf, Cocaine, and Biological Specimens. Forensic science review. 1995;7(2):77-101.
13. Asano N, Yamashita T, Yasuda K, Ikeda K, Kizu H, Kameda Y, et al. Polyhydroxylated alkaloids isolated from mulberry trees (Morusalba L.) and silkworms (Bombyx mori L.). J Agric Food Chem. 2001;49(9):4208-13. https://doi.org/10.1021/jf010567e
14. Hirayama C, Konno K, Wasano N, Nakamura M. Differential effects of sugar-mimic alkaloids in mulberry latex on sugar metabolism and disaccharidases of Eri and domesticated silkworms: Enzymatic adaptation of Bombyx mori to mulberry defense. Insect Biochemistry and Molecular Biology. 2007;37(12):1348-58. https://doi.org/10.1016/j.ibmb.2007.09.001
15. Wahba Khalil SK, Elkheir YM. Dimethyltryptamine from the leaves of certain Acacia species of northern Sudan. Lloydia. 1975;38(2):176-7.
16. Duke D. Phytochemical and Ethnobotanical Databases. [Online Database] 2015
17. Clement BA, Goff CM, Forbes TDA. Toxic amines and alkaloids from Acacia rigidula. Phytochemistry. 1998;49(5):1377-80. https://doi.org/10.1016/S0031-9422(97)01022-4
18. Patcher IJ, Zacharias DE, Ribeiroi O. Indole Alkaloids of Acer saccharinum (the Silver Maple), Dictyoloma incanescens, Piptadenia colubrina, and Mimosa hostilis. Journal of Organic Chemistry. 1959;24(9):1285-7. https://doi.org/10.1021/jo01091a032
19. Rivero-Cruz JF, Lezutekong R, Lobo-Echeverri T, Ito A, Mi Q, Chai HB, et al. Cytotoxic constituents of the twigs of Simarouba glauca collected from a plot in Southern Florida. Phytotherapy research : PTR. 2005;19(2):136-40. https://doi.org/10.1002/ptr.1642
20. Cebrian-Torrejon G, Kahn SA, Ferreira ME, Thirant C, Rojas de Arias A, Figadere B, et al. Alkaloids from Rutaceae: activities of canthin-6-one alkaloids and synthetic analogues on glioblastoma stems cells. MedChemComm. 2012;3(7):771-4. https://doi.org/10.1039/c2md20047c
21. Takayama H. Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa. Chemical & pharmaceutical bulletin. 2004;52(8):916-28. https://doi.org/10.1248/cpb.52.916
22. Avula B, Sagi S, Wang YH, Wang M, Ali Z, Smillie TJ, et al. Identification and Characterization of Indole and Oxindole Alkaloids from Leaves of Mitragyna speciosa Korth Using Liquid Chromatography-Accurate QToF Mass Spectrometry. Journal of AOAC International. 2015;98(1):13-21. https://doi.org/10.5740/jaoacint.14-110
23. Zanolari B, Ndjoko K, Ioset JR, Marston A, Hostettmann K. Qualitative and quantitative determination of yohimbine in authentic yohimbe bark and in commercial aphrodisiacs by HPLC-UV-API/ MS methods. Phytochemical analysis : PCA. 2003;14(4):193-201. https://doi.org/10.1002/pca.699
24. Authority EFS. Scientific Opinion on the evaluation of the safety in use of Yohimbe (Pausinystalia yohimbe (K. Schum.) Pierre ex Beille). EFSA Journal. 2013;11(7):3302. https://doi.org/10.2903/j.efsa.2013.3302
25. Jonville M-C, Dive G, Angenot L, Bero J, Tits M, Ollivier E, et al. Dimeric bisindole alkaloids from the stem bark of Strychnos nux-vomica L. Phytochemistry. 2013;87:157-63. https://doi.org/10.1016/j.phytochem.2012.11.002
26. Schmidt A, Mordhorst T, Nieger M. Investigation of a betainic alkaloid from Punica granatum. Natural product research. 2005;19(5):541-6. https://doi.org/10.1080/14786410500034949
27. Zyryanova OA, Terazawa M, Koike T, Zyryanov VI. White Birch Trees as Resource Species of Russia: Their Distribution, Ecophysiological Features, Multiple Utilizations. Eurasian Journal of Forest Research. 2010;13(1):25-40.
28. Liu H-L, Luo R, Chen X-Q, Ba Y-Y, Zheng L, Guo W-W, et al. Identification and simultaneous quantification of five alkaloids in Piper longum L. by HPLC–ESI-MSn and UFLC–ESI-MS/MS and their application to Piper nigrum L. Food Chemistry. 2015;177:191-6. https://doi.org/10.1016/j.foodchem.2015.01.033
29. Tawara JN, Blokhin A, Foderaro TA, Stermitz FR, Hope H. Toxic piperidine alkaloids from pine (Pinus) and spruce (Picea) trees. New structures and a biosynthetic hypothesis. The Journal of Organic Chemistry. 1993;58(18):4813-8. https://doi.org/10.1021/jo00070a014
30. Gerson E, Kelsey R. Variation of Piperidine Alkaloids in Ponderosa (Pinus poderosa) and Lodgepole Pine (P. contorta) Foliage from Central Oregon. Journal of chemical ecology. 1998;24(5):815-27. https://doi.org/10.1023/A:1022369416745
31. Virjamo V, Julkunen-Tiitto R. Shoot development of Norway spruce (Picea abies) involves changes in piperidine alkaloids and condensed tannins. Trees. 2014;28(2):427-37. https://doi.org/10.1007/s00468-013-0960-3
32. Gerson EA, Kelsey RG, St Clair JB. Genetic variation of piperidine alkaloids in Pinus ponderosa: a common garden study. Annals of botany. 2009;103(3):447-57. https://doi.org/10.1093/aob/mcn228
33. Custodio DL, Florencio da Veiga Junior V. Lauraceae alkaloids. RSC Advances. 2014;4(42):21864-90. https://doi.org/10.1039/C4RA01904K
34. Silva JRdA, CarmoI DFMd, Reis ÉM, Machado GMC, Leon LL, Silva BOd, et al. Chemical and biological evaluation of essential oils with economic value from Lauraceae species. J Braz Chem Soc. 2009;20(6):1071-6. https://doi.org/10.1590/S0103-50532009000600011
35. Chowdhury BK, Sethi ML, Lloyd HA, Kapadia GJ. Aporphine and Tetrahydrobenzylisoquinoline Alkaloids in Sassafras albidum. Phytochemistry. 1976;15:1803-4. https://doi.org/10.1016/S0031-9422(00)97502-2
36. Masnon FF, Hassan NP, Ahmad F. Aporphine alkaloids of Cinnamomum mollissimum and their bioactivities. Natural product communications. 2014;9(1):31-2.
37. Rowe J, Conner A. Extractives in eastern hardwoods: a review. Gen Tech Rep. 1979;FPL-18:1-67.
38. Devappa RK, Rakshit SK, Dekker RFH. Forest biorefinery: Potential of poplar phytochemicals as value-added co-products. Biotechnology Advances. (0).
39. Barbosa P, Gross P, Provan GJ, Pacheco DY, Stermitz FR. Allelochemicals in foliage of unfavored tree hosts of the gypsy moth, Lymantria dispar L.: 1. Alkaloids and other components of Liriodendron tulipifera L. (Magnoliaceae), Acer rubrum L. (Aceraceae), and Cornus florida L. (Cornaceae). Journal of Chemical Ecology. 1990;16(5):1719-30. https://doi.org/10.1007/BF01014103
40. Cleaver L, Nimgirawath S, Ritchie E, Taylor W. The alkaloids of Elmerrillia papuana (Magnoliaceae): Structure and synthesis of elmerrillicine. Australian Journal of Chemistry. 1976;29(9):2003-21. https://doi.org/10.1071/CH9762003
41. Pretzsch H, Grote R, Reineking B, Rotzer T, Seifert S. Models for forest ecosystem management: a European perspective. Annals of botany. 2008;101(8):1065-87. https://doi.org/10.1093/aob/mcm246
42. Garcia-Perez ME, Royer M, Herbette G, Desjardins Y, Pouliot R, Stevanovic T. Picea mariana bark: a new source of trans-resveratrol and other bioactive polyphenols. Food Chem. 2012;135(3):1173-82. https://doi.org/10.1016/j.foodchem.2012.05.050
43. Mulat DG, Latva-Maenpaa H, Koskela H, Saranpaa P, Wahala K. Rapid chemical characterisation of stilbenes in the root bark of Norway spruce by off-line HPLC/DAD-NMR. Phytochemical analysis : PCA. 2014;25(6):529-36. https://doi.org/10.1002/pca.2523
44. Roberts MF, Strack D, Wink M. Biosynthesis of Alkaloids and Betalains. Annual Plant Reviews Volume 40: Biochemistry of Plant Secondary Metabolism: Wiley-Blackwell; 2010. p. 20-91. https://doi.org/10.1002/9781444320503.ch2
45. Harmon AD, Weiss U, Silverton JV. The structure of rohitukine, the main alkaloid of Amoora rohituka (syn. Aphanamixis polystachya) (Meliaceae) [leaves and stems]. Tetrahedron. 1979;20:721-4. https://doi.org/10.1016/S0040-4039(01)93556-7
46. Powell RG, Weisleder D, Smith CR, Wolff IA. Structure of cephalotaxine and related alkaloids. Tetrahedron Letters. 1969;10(46):4081-4. https://doi.org/10.1016/S0040-4039(01)88620-2
47. Lopez-Meyer M, Nessler CL, McKnight TD. Sites of accumulation of the antitumor alkaloid camptothecin in Camptotheca acuminata. Planta medica. 1994;60(6):558-60. https://doi.org/10.1055/s-2006-959571
48. Cordell GA. Fifty years of alkaloid biosynthesis in Phytochemistry. Phytochemistry. 2013;91(0):29-51. https://doi.org/10.1016/j.phytochem.2012.05.012
49. Saidou Balde el H, Megalizzi V, Cao M, Angenot L, Kiss R, Van Damme M, et al. Isostrychnopentamine, an indolomonoterpenic alkaloid from Strychnos usambarensis, with potential anti-tumor activity against apoptosis-resistant cancer cells. Int J Oncol. 2010;36(4):961-5.
50. Goodwin S, Smith A, Horning E. Alkaloids of Ochrosia elliptica. Journal of the American Chemical Society. 1959;81:1903-8. https://doi.org/10.1021/ja01517a031
2. Wink M. Biochemistry of plant secondary metabolism. Annual plant reviews. 2010;40.
3. Dewick PM. Medicinal natural products: a biosynthetic approach. 3rd ed: John Wiley and Sons Ltd; 2009. 539 p. https://doi.org/10.1002/9780470742761
4. Desgagne-Penix I, Farrow SC, Cram D, Nowak J, Facchini PJ. Integration of deep transcript and targeted metabolite profiles for eight cultivars of opium poppy. Plant Mol Biol. 2012;79(3):295-313. https://doi.org/10.1007/s11103-012-9913-2
5. Isah T. Anticancer Alkaloids from Trees: Development into Drugs. Pharmacogn Rev. 2016;10(20):90-9. https://doi.org/10.4103/0973-7847.194047
6. Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. Journal of the American Chemical Society. 1971;93(9):2325-7. https://doi.org/10.1021/ja00738a045
7. Ashihara H, Sano H, Crozier A. Caffeine and related purine alkaloids: Biosynthesis, catabolism, function and genetic engineering. Phytochemistry. 2008;69(4):841-56. https://doi.org/10.1016/j.phytochem.2007.10.029
8. Koyama Y, Tomoda Y, Kato M, Ashihara H. Metabolism of purine bases, nucleosides and alkaloids in theobromine-forming Theobroma cacao leaves. Plant Physiology and Biochemistry. 2003;41(11–12):977-84. https://doi.org/10.1016/j.plaphy.2003.07.002
9. Niemenak N, Onomo PE, Fotso, Lieberei R, Ndoumou DO. Purine alkaloids and phenolic compounds in three Cola species and Garcinia kola grown in Cameroon. South African Journal of Botany. 2008;74(4):629-38. https://doi.org/10.1016/j.sajb.2008.03.003
10. Epifano F, Fiorito S, Genovese S. Phytochemistry and pharmacognosy of the genus Acronychia. Phytochemistry. 2013;95:12-8. https://doi.org/10.1016/j.phytochem.2013.07.013
11. Tillequin F. Alkaloids in the genus Sarcomelicope. Recent Research Develop Phytochemistry. 1997;1:675–87.
12. Moore JM, Moore JF, Fodor G, Jones AB. Detection and Characterization of Cocaine and Related Tropane Alkaloids in Coca Leaf, Cocaine, and Biological Specimens. Forensic science review. 1995;7(2):77-101.
13. Asano N, Yamashita T, Yasuda K, Ikeda K, Kizu H, Kameda Y, et al. Polyhydroxylated alkaloids isolated from mulberry trees (Morusalba L.) and silkworms (Bombyx mori L.). J Agric Food Chem. 2001;49(9):4208-13. https://doi.org/10.1021/jf010567e
14. Hirayama C, Konno K, Wasano N, Nakamura M. Differential effects of sugar-mimic alkaloids in mulberry latex on sugar metabolism and disaccharidases of Eri and domesticated silkworms: Enzymatic adaptation of Bombyx mori to mulberry defense. Insect Biochemistry and Molecular Biology. 2007;37(12):1348-58. https://doi.org/10.1016/j.ibmb.2007.09.001
15. Wahba Khalil SK, Elkheir YM. Dimethyltryptamine from the leaves of certain Acacia species of northern Sudan. Lloydia. 1975;38(2):176-7.
16. Duke D. Phytochemical and Ethnobotanical Databases. [Online Database] 2015
17. Clement BA, Goff CM, Forbes TDA. Toxic amines and alkaloids from Acacia rigidula. Phytochemistry. 1998;49(5):1377-80. https://doi.org/10.1016/S0031-9422(97)01022-4
18. Patcher IJ, Zacharias DE, Ribeiroi O. Indole Alkaloids of Acer saccharinum (the Silver Maple), Dictyoloma incanescens, Piptadenia colubrina, and Mimosa hostilis. Journal of Organic Chemistry. 1959;24(9):1285-7. https://doi.org/10.1021/jo01091a032
19. Rivero-Cruz JF, Lezutekong R, Lobo-Echeverri T, Ito A, Mi Q, Chai HB, et al. Cytotoxic constituents of the twigs of Simarouba glauca collected from a plot in Southern Florida. Phytotherapy research : PTR. 2005;19(2):136-40. https://doi.org/10.1002/ptr.1642
20. Cebrian-Torrejon G, Kahn SA, Ferreira ME, Thirant C, Rojas de Arias A, Figadere B, et al. Alkaloids from Rutaceae: activities of canthin-6-one alkaloids and synthetic analogues on glioblastoma stems cells. MedChemComm. 2012;3(7):771-4. https://doi.org/10.1039/c2md20047c
21. Takayama H. Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa. Chemical & pharmaceutical bulletin. 2004;52(8):916-28. https://doi.org/10.1248/cpb.52.916
22. Avula B, Sagi S, Wang YH, Wang M, Ali Z, Smillie TJ, et al. Identification and Characterization of Indole and Oxindole Alkaloids from Leaves of Mitragyna speciosa Korth Using Liquid Chromatography-Accurate QToF Mass Spectrometry. Journal of AOAC International. 2015;98(1):13-21. https://doi.org/10.5740/jaoacint.14-110
23. Zanolari B, Ndjoko K, Ioset JR, Marston A, Hostettmann K. Qualitative and quantitative determination of yohimbine in authentic yohimbe bark and in commercial aphrodisiacs by HPLC-UV-API/ MS methods. Phytochemical analysis : PCA. 2003;14(4):193-201. https://doi.org/10.1002/pca.699
24. Authority EFS. Scientific Opinion on the evaluation of the safety in use of Yohimbe (Pausinystalia yohimbe (K. Schum.) Pierre ex Beille). EFSA Journal. 2013;11(7):3302. https://doi.org/10.2903/j.efsa.2013.3302
25. Jonville M-C, Dive G, Angenot L, Bero J, Tits M, Ollivier E, et al. Dimeric bisindole alkaloids from the stem bark of Strychnos nux-vomica L. Phytochemistry. 2013;87:157-63. https://doi.org/10.1016/j.phytochem.2012.11.002
26. Schmidt A, Mordhorst T, Nieger M. Investigation of a betainic alkaloid from Punica granatum. Natural product research. 2005;19(5):541-6. https://doi.org/10.1080/14786410500034949
27. Zyryanova OA, Terazawa M, Koike T, Zyryanov VI. White Birch Trees as Resource Species of Russia: Their Distribution, Ecophysiological Features, Multiple Utilizations. Eurasian Journal of Forest Research. 2010;13(1):25-40.
28. Liu H-L, Luo R, Chen X-Q, Ba Y-Y, Zheng L, Guo W-W, et al. Identification and simultaneous quantification of five alkaloids in Piper longum L. by HPLC–ESI-MSn and UFLC–ESI-MS/MS and their application to Piper nigrum L. Food Chemistry. 2015;177:191-6. https://doi.org/10.1016/j.foodchem.2015.01.033
29. Tawara JN, Blokhin A, Foderaro TA, Stermitz FR, Hope H. Toxic piperidine alkaloids from pine (Pinus) and spruce (Picea) trees. New structures and a biosynthetic hypothesis. The Journal of Organic Chemistry. 1993;58(18):4813-8. https://doi.org/10.1021/jo00070a014
30. Gerson E, Kelsey R. Variation of Piperidine Alkaloids in Ponderosa (Pinus poderosa) and Lodgepole Pine (P. contorta) Foliage from Central Oregon. Journal of chemical ecology. 1998;24(5):815-27. https://doi.org/10.1023/A:1022369416745
31. Virjamo V, Julkunen-Tiitto R. Shoot development of Norway spruce (Picea abies) involves changes in piperidine alkaloids and condensed tannins. Trees. 2014;28(2):427-37. https://doi.org/10.1007/s00468-013-0960-3
32. Gerson EA, Kelsey RG, St Clair JB. Genetic variation of piperidine alkaloids in Pinus ponderosa: a common garden study. Annals of botany. 2009;103(3):447-57. https://doi.org/10.1093/aob/mcn228
33. Custodio DL, Florencio da Veiga Junior V. Lauraceae alkaloids. RSC Advances. 2014;4(42):21864-90. https://doi.org/10.1039/C4RA01904K
34. Silva JRdA, CarmoI DFMd, Reis ÉM, Machado GMC, Leon LL, Silva BOd, et al. Chemical and biological evaluation of essential oils with economic value from Lauraceae species. J Braz Chem Soc. 2009;20(6):1071-6. https://doi.org/10.1590/S0103-50532009000600011
35. Chowdhury BK, Sethi ML, Lloyd HA, Kapadia GJ. Aporphine and Tetrahydrobenzylisoquinoline Alkaloids in Sassafras albidum. Phytochemistry. 1976;15:1803-4. https://doi.org/10.1016/S0031-9422(00)97502-2
36. Masnon FF, Hassan NP, Ahmad F. Aporphine alkaloids of Cinnamomum mollissimum and their bioactivities. Natural product communications. 2014;9(1):31-2.
37. Rowe J, Conner A. Extractives in eastern hardwoods: a review. Gen Tech Rep. 1979;FPL-18:1-67.
38. Devappa RK, Rakshit SK, Dekker RFH. Forest biorefinery: Potential of poplar phytochemicals as value-added co-products. Biotechnology Advances. (0).
39. Barbosa P, Gross P, Provan GJ, Pacheco DY, Stermitz FR. Allelochemicals in foliage of unfavored tree hosts of the gypsy moth, Lymantria dispar L.: 1. Alkaloids and other components of Liriodendron tulipifera L. (Magnoliaceae), Acer rubrum L. (Aceraceae), and Cornus florida L. (Cornaceae). Journal of Chemical Ecology. 1990;16(5):1719-30. https://doi.org/10.1007/BF01014103
40. Cleaver L, Nimgirawath S, Ritchie E, Taylor W. The alkaloids of Elmerrillia papuana (Magnoliaceae): Structure and synthesis of elmerrillicine. Australian Journal of Chemistry. 1976;29(9):2003-21. https://doi.org/10.1071/CH9762003
41. Pretzsch H, Grote R, Reineking B, Rotzer T, Seifert S. Models for forest ecosystem management: a European perspective. Annals of botany. 2008;101(8):1065-87. https://doi.org/10.1093/aob/mcm246
42. Garcia-Perez ME, Royer M, Herbette G, Desjardins Y, Pouliot R, Stevanovic T. Picea mariana bark: a new source of trans-resveratrol and other bioactive polyphenols. Food Chem. 2012;135(3):1173-82. https://doi.org/10.1016/j.foodchem.2012.05.050
43. Mulat DG, Latva-Maenpaa H, Koskela H, Saranpaa P, Wahala K. Rapid chemical characterisation of stilbenes in the root bark of Norway spruce by off-line HPLC/DAD-NMR. Phytochemical analysis : PCA. 2014;25(6):529-36. https://doi.org/10.1002/pca.2523
44. Roberts MF, Strack D, Wink M. Biosynthesis of Alkaloids and Betalains. Annual Plant Reviews Volume 40: Biochemistry of Plant Secondary Metabolism: Wiley-Blackwell; 2010. p. 20-91. https://doi.org/10.1002/9781444320503.ch2
45. Harmon AD, Weiss U, Silverton JV. The structure of rohitukine, the main alkaloid of Amoora rohituka (syn. Aphanamixis polystachya) (Meliaceae) [leaves and stems]. Tetrahedron. 1979;20:721-4. https://doi.org/10.1016/S0040-4039(01)93556-7
46. Powell RG, Weisleder D, Smith CR, Wolff IA. Structure of cephalotaxine and related alkaloids. Tetrahedron Letters. 1969;10(46):4081-4. https://doi.org/10.1016/S0040-4039(01)88620-2
47. Lopez-Meyer M, Nessler CL, McKnight TD. Sites of accumulation of the antitumor alkaloid camptothecin in Camptotheca acuminata. Planta medica. 1994;60(6):558-60. https://doi.org/10.1055/s-2006-959571
48. Cordell GA. Fifty years of alkaloid biosynthesis in Phytochemistry. Phytochemistry. 2013;91(0):29-51. https://doi.org/10.1016/j.phytochem.2012.05.012
49. Saidou Balde el H, Megalizzi V, Cao M, Angenot L, Kiss R, Van Damme M, et al. Isostrychnopentamine, an indolomonoterpenic alkaloid from Strychnos usambarensis, with potential anti-tumor activity against apoptosis-resistant cancer cells. Int J Oncol. 2010;36(4):961-5.
50. Goodwin S, Smith A, Horning E. Alkaloids of Ochrosia elliptica. Journal of the American Chemical Society. 1959;81:1903-8. https://doi.org/10.1021/ja01517a031
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Desgagné-Penix I. Distribution of alkaloids in woody plants. Plant Sci. Today [Internet]. 2017 Sep. 5 [cited 2024 Nov. 23];4(3):137-42. Available from: https://horizonepublishing.com/journals/index.php/PST/article/view/320
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