Publish with Nova Science Publishers
We publish over 800 titles annually by leading researchers from around the world. Submit a Book Proposal Now!
Silky Sethy1, Neha Minocha2 and Rohini Agrawal3
1SGT College of Pharmacy, SGT University, Gurugram, Haryana, India
2School of Pharmacy, Chitkara University, Himachal Pradesh, India
3College of Pharmacy, JSS Academy of Technical Education, Noida, India
Part of the book: The Essential Guide to Alkaloids
Tropane alkaloids (TA) are treasured secondary plant metabolites that are frequently determined in high concentrations from Solanaceae and Erythroxylaceae family. The TAs, which can be characterized by their particular bicyclic tropane ring device, may be divided into 3 essential categories: hyoscyamine and scopolamine, cocaine and calystegines. Even though all TAs have the identical primary structure, they range immensely in their biological, chemical and pharmacological properties. Scopolamine, also known as hyoscine, has the most important significant marketplace as a pharmacological agent due to its role in treatment of nausea, vomiting, motion sickness, as well as smooth muscle spasms while cocaine is the second maximum regularly consumed illicit drug globally. This assessment presents a comprehensive review of TAs, highlighting their structural variations, use in pharmaceutical therapy from each ancient and modern perspective, herbal biosynthesis in plants and increasing production opportunities using tissue and microbial biosynthesis of those compounds.
Keywords: tropane alkaloids, solanaceae, cocaine, scopolamine, microbial biosynthesis
Barnes PJ (2000). The pharmacological properties of tiotropium. Chest, 117, 63S–66S.
Bencharit S, Morton CL, Xue Y, Potter PM, Redinbo MR (2003). Structural basis of heroin
and cocaine metabolism by a promiscuous human drug-processing enzyme. Nat Struct
Biol, 10, 349–356.
Camps P, Munoz-Torrero D: Cholinergic drugs in pharmacotherapy of Alzheimer’s
disease. Mini Rev Med Chem, 2002, 2, 11–25.
Carroll ME, Howell LL, Kuhar MJ (1999). Pharmacotherapies for treatment of cocaine
abuse: preclinical aspects. J Med Chem, 42, 2721–2736.
Casale JF (1987). A practical synthesis of cocaine’s enantiomers. Forensic Sci Int, 33, 275–298.
Caulfield MP, Birdsall NJ (1998). Classification of muscarinic acetylcholine receptors.
Pharmacol Rev, 50, 279–290.
Chen H, Chen Y, Wang H, Du P, Han F, Zhang H (2005). Analysis of scopolamine and its
eighteen metabolites in rat urine by liquid chromatography – tandem mass
spectrometry. Talanta, 67, 984–991.
Chin YW, Kinghorn AD, Patil PN (2007). Evaluation of the cholinergic and adrenergic
effects of two tropane alkaloids from Erythroxylumpervillei. Phytother Res, 21, 1002–1005.
Christen P (2000). Tropane alkaloids: old drugs used in modern medicine. In: Studies in
Natural Products Chemistry, Bioactive Natural Products, Part C. Ed. Rahman A,
Elsevier Science and Technology, Amsterdam, 22, 717–749.
Christen P, Bieri S, Veuthey JL (2007). Analysis of tropane alkaloids in biological matrices.
In: Modern Alkaloids. Structure, Isolation, Synthesis and Biology. Ed. Fatorusso E,
Taglialatela-Scafati O, Wiley-VCH, Weinheim, New York, 339–367.
Dickerson TJ, Janda KD (2005). Recent advances for the treatment of cocaine abuse:
central nervous system immunopharmacotherapy. AAPS J, 7, E579–E586.
Dräger B (2004). Chemistry and biology of calystegines. Nat Prod Rep, 21, 211–223.
Eglen RM, Choppin A, Dillon MP, Hegde S (1999). Muscarinic receptor ligands and their
therapeutic potential. CurrOpin Chem Biol, 3, 426–432.
Fierz G, Chidgey R, Hoffmann HMR (1974). A new tropinone synthesis. Angew Chem Int
Ed Engl, 1974, 13, 410–411.
Fodor G (1971). The tropane alkaloids. In: The Alkaloids; Chemistry and Physiology, vol.
XIII. Ed. Manske RHF, Academic Press, New York, 351–396.
Frey KA, Ehrenkaufer RL, Agranoff BW (1985). Quantitative in vivo receptor binding.
Autoradiographic imaging of muscarinic cholinergic receptors. J Neurosci, 5, 2407–2414.
Ghelardini C, Galeotti N, Romanelli MN, Gualtieri F, Bartolini A (2000). Pharmacological
characterization of the novel ACh releaser -tropanyl 2(4-bromophenyl)propionate.
CNS Drug Rev, 6, 63–78.
Gomeza J, Yamada M, Duttaroy A, Zhang W, Makita R, Miyakawa T, Crawley J, Zhang
L, Shannon H, Bymaster FP, Felder CC, Deng C, Wess J (2002). Muscarinic
acetylcholine receptor knockout mice: phenotypical analysis and clinical implications.
In: Trends in Drug Research III. Ed. van der Goot H, Elsevier Science BV,
Amsterdam, pp. 97–113.
Griffin WJ, Lin GD (2000). Chemotaxonomy and geographical distribution of tropane
alkaloids. Phytochemistry 53, 623–637.
Gualtieri F (2000). Cholinergic receptors and neurodegenerative diseases. Pharm Acta
Helv, 74, 85–89.
Gyermek L (1997). Tropane alkaloids. In: Pharmacology of Antimuscarinic Agents. Ed.
Gyermek L, CRC Press, Boca Raton, pp. 47–160.
Gyermek L (2002). Structure-activity relationships among derivatives of dicarboxylic acid
esters of tropine. Pharmacol Ther, 96, 1–21.
Henry TA (1949). The tropane alkaloids. In: The Plant Alkaloids. Ed. Henry TA, JA
Churchill Ltd, London, pp. 69–118.
Holzman RS (1998) The legacy of Atropos, the fate who cut the thread of life.
Anesthesiology, 89, 241–249.
Humphrey AJ, O’Hagan D (2001). Tropane alkaloid biosynthesis. A century old problem
unresolved. Nat Prod Rep, 18, 494–502.
Husband A, Worsley A (2007). Nausea and vomiting – pharmacological management.
Hospital Pharmacist, 14, 189–192.
Jaber-Vazdekis NE, Gutierrez-Nicolas F, Ravelo AG, Zarate R (2006). Studies on tropane
alkaloid extraction by volatile organic solvents: dichloromethane. Phytochem Anal,
Jung D, Song J, Lee D, Kim Y, Lee Y, Hahn J (2006). Synthesis of 2-substituted 8-
azabicyclo[3.2.1]octan-3-ones in aqueous NaOH solution at low concentration. Bull
Korean Chem Soc, 27, 1493–1496.
Kreek MJ, Bart G, Lilly C, Laforge KS, Nielsen DA (2005). Pharmacogenetics and human
molecular genetics of opiate and cocaine addictions and their treatments. Pharmacol
Rev, 57, 1–26.
Leake CD, Pelikan EW (1976). An historical account of pharmacology to the 20th century
(Book review). J Clin Pharmacol, 16, 669–671.
Lever JR, Zou MF, Parnas ML, Duval RA, Wirtz SE, Justice JB, Vaughan RA, Newman
AH (2005). Radioiodinatedazide and isocyanate derivatives of cocaine for irreversible
labeling of dopamine transporters: synthesis and co-valent binding studies. Bioconjug
Chem, 16, 644–649.
Lounasmaa M, Tamminen T (1993). The tropane alkaloids. In: The Alkaloids. Ed. Brossi
A, Academic Press, New York, 44, 1–114.
Mahagamasekera MGP, Doran PM (1997). Intergeneric coculture of genetically
transformed organs for the production of scopolamine. Phytochemistry, 47, 17–25.
Maksay G, Nemes P, Biro T (2004). Synthesis of tropeines and allosteric modulation of
ionotropic glycine receptors. J Med Chem, 47, 6384–6391.
Norby FL, Ren J (2002). Anisodamine inhibits cardiac contraction and intracellular Ca
transients in isolated adult rat ventricular myocytes. Eur J Pharmacol, 439, 21–25.
Oksman-Caldentey KM (2007). Tropane and nicotine alkaloid biosynthesis – novel
approach towards biotechnological production of plant derived pharmaceuticals. Curr
Pharm Biotechnol, 8, 2003–2010.
Patterson S, O’Hagan D (2002). Biosynthetic studies on tropane alkaloid hyoscyamine in
Datura stramonium; hyoscyamine is stable to in vivo oxidation and is not derived from
littorine via a vicinal interchange process. Phytochemistry, 61, 323–329.
Pleuvry PJ: Physiology and pharmacology of nausea and vomiting. AnesthInte Care Med,
2006, 7, 473–477.
Renner UD, Oertel R, Kirch W (2005). Pharmacokinetics and pharmacodynamics in
clinical use of scopolamine: Ther Drug Monit, 27, 655–665.
Robins R, Walton N (1993). The biosynthesis of tropane alkaloids. In: The Alkaloids. Ed.
Brossi A, Academic Press, New York, 44, 115–187.
Romanelli MN, Gratteri P, Guandalini L, Martini E, Bonacini C, Gualtieri F (2007). Central
nicotinic receptors: structure, function, ligands and therapeutic potential. Chem Med
Chem, 2, 746–767.
Simpson K, Spencer CM, McClellan KJ (2000). Tropisetron; an update of its use in the
prevention of chemotherapy induced nausea and vomiting. Drugs, 2000, 59, 1297–1315.
Sneader W (2005). Plant products analogues and compounds derived from them. In: Drug
Discovery; A History. Ed. Sneader W, Wiley & Sons, Ltd, Chichester, 2005, 115–150.
Somand H, Remington TL (2005). Tiotropium: a bronchodilator for chronic obstructive
pulmonary disease. Ann Pharmacother, 39, 1467–1475.
Sora I, Hall FS, Andrews AM, Itokawa M, Li XF, Wei HB, Wichems C, Lesch KP, Murphy
DL, Uhl GR (2001). Molecular mechanism of cocaine reward: combined dopamine
and serotonin transporter knockouts eliminate cocaine place preference. Proc Natl
Acad Sci USA, 98, 5300–5305.
Virmani OP, Sharma A, Kumar A (1982). Cultivation of Duboisia as a commercial source
of hyoscine and hyoscyamine – a review. Curr Res Med Arom Plants, 4, 47–56.
Wess J (1993). Molecular basis of muscarinic acetylcholine receptor functions. Trends
Pharmacol Sci, 14, 308–313.
Xiu RJ, Hammerschmidt DE, Coppo PA, Jacob HS (1982). Anisodamine inhibits
thromboxane synthesis, granulocyte aggregation, and platelet aggregation. A possible
mechanism for its efficacy in bacteremic shock. JAMA, 247, 1458–1460.
Yamada Y, Tabata M (1997). Plant biotechnology of tropane alkaloids. Plant Biotechnol,
Zarate R, Jaber-Vazdekis NE, Medina B, Ravelo AG (2006). Tailoring tropane alkaloid
accumulation in transgenic hairy roots with gene encoding hyoscyamine 6–
hydroxylase. Biotechnol Lett, 28, 1271–1277.