Apparicine
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IUPAC name
(19E)-2,7,16,17,19,20-Hexadehydro-3,7-seco-6-norcuran
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Systematic IUPAC name
(2R,4E,5S)-4-Ethylidene-6-methylidene-1,3,4,5,6,7-hexahydro-2,5-ethanoazocino[4,3-b]indole | |
Identifiers | |
3D model (
JSmol ) |
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3DMet | |
ChEBI | |
ChEMBL | |
ChemSpider | |
KEGG | |
PubChem CID
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Properties | |
C18H20N2 | |
Molar mass | 264.372 g·mol−1 |
Density | 0.945875 |
log P | 3.404 |
Acidity (pKa) | 8.37 |
Refractive index (nD)
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1.665 |
0.552121 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Apparicine is a
Biochemistry
Research on Aspidosperma pyricollum has led to the discovery that apparicine is biosynthesised from tryptophan by "loss of C-2 and retention of C-3".[10] The biosynthesis of apparicine requires alteration of the usual tryptamine side chain with loss of C-1.[1]
Structure determination
Its structure was established through the methods of chemical decomposition, and the nascent field of nuclear magnetic resonance (NMR) decoupling using the 1H isotope of hydrogen.[11] Ultraviolet–visible spectroscopy showed that apparicine has a similar UV absorption to uleine,[12] and their chromophores were found to be identical.[11]
NMR decoupling experiments revealed that apparicine lacks an N-methyl signal and has one methylenic carbon atom between the nitrogen atom and the indole rings, allowing researchers to distinguish it from uleine.[12] This was a notable early use of NMR decoupling to determine a chemical structure.[12] Its carbon skeleton was found to be related but different from that of uleine, and the structures of vallesamine and O-acetyl-vallesamine to be related to apparicine.[13]
Applications
Apparicine may have several potential applications. In
See also
Notes
- ^ a b Herbert 1983, p. 13.
- ^ Elia 2008, p. 594.
- ^ a b Joule 1983, p. 286.
- ^ Joule et al. 1965, p. 4773.
- ^ Gilbert 1968, p. 273.
- ^ Monteiro 1966, p. 39.
- ^ Verpoorte et al. 1989, p. 139.
- ^ Elia 2008, p. 593.
- ^ Elia 2008, p. 596.
- ^ Shamma 1970, p. 324.
- ^ a b Joule et al. 1980, p. 230.
- ^ a b c Joule 1983, p. 287.
- ^ Biemann 1966, p. 40.
- ^ Joule 1983, p. 288.
- ^ a b c Schmelzer 2008, p. 592.
- ^ a b Mairura & Schmelzer 2008, p. 590.
- ^ Ingkaninan et al. 1999, p. 1441.
- S2CID 196613130.
References
- Biemann, Klaus (1966). "Mass spectrometry of selected natural products". In Zechmeister, L. (ed.). Fortschritte der Chemie organischer Naturstoffe. Vol. 24. PMID 5958065.
- Elia, J. (2008). "Tabernaemontana pachysiphon Stapf". In Schmelzer, G. H.; Gurib-Fakim, A. (eds.). Medicinal Plants 1. ISBN 978-90-5782-204-9.
- Gilbert, B. (1968). "The alkaloids of Aspidosperma, Ochrosia, Pleiocarpa, Melodinus, and related genera". In Manske, R. H. F. (ed.). The Alkaloids: Chemistry and Physiology. Vol. 11. ISBN 978-0-12-469511-5.
- Herbert, Richard B. (1983). "Structural and biosynthetic relationships". In Saxton, J. Edwin (ed.). Indoles: Part Four: The Monoterpenoid Indole Alkaloids. The Chemistry of Heterocyclic Compounds. Vol. 25. ISBN 0-471-89748-5.
- Ingkaninan, K.; Ijzerman, A. P.; Taesotikul, T.; Verpoorte, R. (1999). "Isolation of opioid-active compounds from Tabernaemontana pachysiphon leaves". S2CID 45544097.
- Joule, John A. (1983). "The uleine–ellipticine–vallesamine group". In Saxton, J. Edwin (ed.). Indoles: Part Four: The Monoterpenoid Indole Alkaloids. The Chemistry of Heterocyclic Compounds. Vol. 25. John Wiley & Sons. pp. 265–292. ISBN 0-471-89748-5.
- Joule, J. A.; Allen, M. S.; Bishop, D. I.; Harris, M.; et al. (1980). "Approaches to the synthesis of apparicine". In Phillipson, John David; Zenk, M. H. (eds.). Indole and Biogenetically Related Alkaloids. Annual Proceedings of the Phytochemical Society of Europe. Vol. 17. Academic Press. pp. 229–248. ISBN 0-12-554450-2.
- Joule, J. A.; Monteiro, H.; Durham, L. J.; Gilbert, B.; et al. (1965). "Alkaloid studies. Part XLVIII. The structure of apparicine, a novel Aspidosperma alkaloid". PMID 5891947.
- Mairura, F. S.; Schmelzer, G. H. (2008). "Tabernaemontana crassa Benth.". In Schmelzer, G. H.; Gurib-Fakim, A. (eds.). Medicinal Plants 1. Plant Resources of Tropical Africa. Vol. 11. PROTA Foundation; Backhuys Publishers; CTA. pp. 589–592. ISBN 978-90-5782-204-9.
- Monteiro, Hugo Jorge (1966). Studies on some indole alkaloids: the structure of vallesiachotamine. apparicine, an indole alkaloid of novel structure. the structure and chemistry of nervobscurine. tubulosine and its chemical correlation with deoxytubulosine, Parts 1–4.
- Schmelzer, G. H. (2008). "Tabernaemontana elegans Stapf". In Schmelzer, G. H.; Gurib-Fakim, A. (eds.). Medicinal Plants 1. Plant Resources of Tropical Africa. Vol. 11. PROTA Foundation; Backhuys Publishers; CTA. pp. 592–593. ISBN 978-90-5782-204-9.
- Shamma, Maurice (1970). "Alkaloids". In Cain, Cornelius K.; et al. (eds.). Annual Reports in Medicinal Chemistry, 1969. Academic Press. pp. 323–332. ISBN 978-0-12-040505-3.
- Verpoorte, R.; van der Heijden, R.; Schripsema, J.; Sierra, M.; et al. (1989). "Secondary metabolites in cell cultures of Teabernaemontana species". In Kurz, Wolfgang G. W. (ed.). Primary and Secondary Metabolism of Plant Cell Cultures II. Springer-Verlag. pp. 138–148. ISBN 978-3-642-74553-9.
External links
- (-)-Apparicine in the United States Environmental Protection Agency's CompTox Database
- (-)-Apparicine at KNApSAck