“Apparicine”的意思、由来-开放百科全书

词条

Apparicine

释义

Biochemistry
Structure determination
Applications
Notes
References
External links

{{Chembox
| ImageFile = Apparicine.svg
| ImageSize = 200px
| ImageAlt =
| IUPACName = (13S,14E)-14-Ethylidene-12-methylene-1,10-diazatetracyclo[11.2.2.03,11.04,9]heptadeca-3(11),4,6,8-tetraene
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 3463-93-2
| 3DMet = B02701
| ChEBI = 78
| ChemSpiderID = 4444718
| ChEMBL = 285671
| InChI = 1S/C18H20N2/c1-3-13-10-20-9-8-14(13)12(2)18-16(11-20)15-6-4-5-7-17(15)19-18/h3-7,14,19H,2,8-11H2,1H3/b13-3-/t14-/m1/s1
| InChIKey = LCVACABZTLIWCE-CRAFIKPXSA-N
| KEGG = C09036
| PubChem = 5320486
| SMILES = C\\C=C1\\C[N@]2CC[C@@H]1C(=C)c1[nH]c3ccccc3c1C2
| Section2 = {{Chembox Properties
|C=18|H=20|N=2
| Appearance =
| Density = 0.945875
| MeltingPt =
| BoilingPt =
| Solubility =
| pKa = 8.37
| LogP = 3.404
| Dipole = 0.552121
| RefractIndex = 1.665
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

Apparicine is a monoterpenoid indole alkaloid.{{sfn|Saxton|1983|p=13}} It is named after Apparicio Duarte, a Brazilian botanist who studied the Aspidosperma species from which apparicine was first isolated.{{sfn|Schmelzer|Gurib-Fakim|2008|p=594}}{{sfn|Saxton|1983|p=286}} It was the first member of the vallesamine group of alkaloids to be isolated and have its structure established,{{sfn|Saxton|1983|p=286}} which was first published in 1965.{{sfn|Joule|Monteiro|Durham|Gilbert|1965|p=4773}} It has also been known by the synonyms gomezine, pericalline, and tabernoschizine.{{sfn|Helmuth|Manske|Holmes|1968|p=273}}

Biochemistry

The alkaloid has been isolated from seven species of Aspidosperma.{{sfn|Monteiro|1966|p=39}} It is the principal alkaloid found in the callus of Tabernaemontana elegans, and has also been identified in other Tabernaemontana species, including T. africana, T. divaricata, T. orientalis, and T. pachysiphon.{{sfn|Kurz|2012|p=139}}{{sfn|Schmelzer|Gurib-Fakim|2008|p=593}} In studies of T. pachysiphon, it was found that alkaloid content including that of apparicine was greatest in young leaves and leaves receiving greater shade, and varied with leaf age, plant age, and provenance.{{sfn|Schmelzer|Gurib-Fakim|2008|p=596}}

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".{{sfn|Cain|1970|p=324}} The biosynthesis of apparicine requires alteration of the usual tryptamine side chain with loss of C-1.{{sfn|Saxton|1983|p=13}}

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.{{sfn|Phillipson|Zenk|1980|p=230}} Ultraviolet–visible spectroscopy showed that apparicine has a similar UV absorption to uleine,{{sfn|Saxton|1983|p=287}} and their chromophores were found to be identical.{{sfn|Phillipson|Zenk|1980|p=230}}

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.{{sfn|Saxton|1983|p=287}} This was a notable early use of NMR decoupling to determine a chemical structure.{{sfn|Saxton|1983|p=287}} 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.{{sfn|Biemann|Erdtman|Fraenkel-Conrat|Hoffmann-Ostenhof|2012|p=40}}

Dehydrogenation of apparicine followed by oxidation with permanganate allowed location of the two piperidine ring carbon substituents.{{sfn|Saxton|1983|p=288}}

Applications

Apparicine may have several potential applications. In cell cultures, it has shown cytotoxicity against the experimental lymphocytic leukemia P388 cell line.{{sfn|Schmelzer|Gurib-Fakim|2008|p=592}} It exhibits strong activity against poliovirus type 3 (PV3),{{sfn|Schmelzer|Gurib-Fakim|2008|p=592}} and has moderate to strong activity against some human pathogens.{{sfn|Schmelzer|Gurib-Fakim|2008|p=590}} It is also active at opioid receptors{{sfn|Schmelzer|Gurib-Fakim|2008|p=592}} and has micromolar affinity for adenosine receptors.{{sfn|Ingkaninan|Ijzerman|Taesotikul|Verpoorte|1999|p=1441}} Apparicine has local analgesic properties.{{sfn|Schmelzer|Gurib-Fakim|2008|p=590}}

Notes

References

{{cite book|title=Progress in the Chemistry of Organic Natural Products|series=Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products|volume=24|last1=Biemann|first1=K.|last2=Erdtman|first2=H.|last3=Fraenkel-Conrat|first3=H.|last4=Hoffmann-Ostenhof|first4=O.|last5=Kindl|first5=H.|last6=Norin|first6=T.|last7=Tschesche|first7=R.|last8=Turner|first8=A.B.|last9=Warren|first9=F.L.|publisher=Springer Science & Business Media|date=2012|isbn=978-3-7091-8143-0|ref=harv}}
{{cite book|title=Annual Reports in Medicinal Chemistry, 1969|series=Annual Reports in Medicinal Chemistry|editor-last=Cain|editor-first=Cornelius K.|volume=5|publisher=Academic Press|date=1970|isbn=978-0-08-058349-5|ref=harv}}
{{cite encyclopedia|encyclopedia=The Alkaloids: Chemistry and Physiology|title=|editor-last1=Helmuth|editor-first1=Richard|editor-last2=Manske|editor-first2=Fred|editor-last3=Holmes|editor-first3=Henry Lavergne|volume=11|publisher=Academic Press|year=1968|isbn=|ref=harv}}
{{cite journal|journal=Journal of Pharmacy and Pharmacology|title=Isolation of Opioid-active Compounds from Tabernaemontana pachysiphon leaves|last1=Ingkaninan|first1=K.|last2=Ijzerman|first2=A.P.|last3=Taesotikul|first3=T.|last4=Verpoorte|first4=R.|volume=51|issue=12|date=1999|pages=1441–1446|doi=10.1211/0022357991777092|pmid=10678501|issn=2042-7158|ref=harv}}
{{cite journal|journal=Journal of the Chemical Society|title=Alkaloid studies. Part XLVIII. The structure of apparicine, a novel aspidosperma alkaloid|last1=Joule|first1=J. A.|last2=Monteiro|first2=H.|last3=Durham|first3=L.J.|last4=Gilbert|first4=B.|last5=Djerassi|first5=Carl|date=1965|pages=4773–4780|doi=10.1039/JR9650004773|ref=harv}}
{{cite encyclopedia|encyclopedia=Primary and Secondary Metabolism of Plant Cell Cultures II|last=Kurz|first=Wolfgang G.W.|publisher=Springer-Verlag|year=2012|isbn=978-3-642-74551-5|doi=10.1007/978-3-642-74551-5_16|ref=harv|chapter=Secondary Metabolites in Cell Cultures of Tabernaemontana Species|title=Primary and Secondary Metabolism of Plant Cell Cultures II|pages=138–148}}
{{cite book|title=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|last=Monteiro|first=Hugo Jorge|publisher=|year=1966|isbn=|oclc=|ref=harv}}
{{cite book|title=Indole and Biogenetically Related Alkaloids|editor-last1=Phillipson|editor-first1=John David|editor-last2=Zenk|editor-first2=M.H.|others=Phytochemical Society of Europe|volume=17|series=Annual proceedings of the Phytochemical Society of Europe|publisher=Academic Press|year=1980|isbn=978-0-12-554450-4|issn=0309-9393|ref=harv}}
{{cite encyclopedia|encyclopedia=The Chemistry of Heterocyclic Compound|title=Indoles: Part Four: The Monoterpenoid Indole Alkaloids|editor-last=Saxton|editor-first=J. Edwin|volume=25|publisher=John Wiley & Sons|year=1983|isbn=978-0-470-18844-6|ref=harv}}
{{cite book|title=Medicinal Plants|volume=1|editor-last1=Schmelzer|editor-first1=G.H.|editor-last2=Gurib-Fakim|editor-first2=A.|publisher=PROTA Foundation, Backhuys Publishers|date=2008|isbn=9789057822049|issn=1877-430X|ref=harv}}

External links

[https://comptox.epa.gov/dashboard/dsstoxdb/results?search=DTXSID30415108 (-)-Apparicine] at the United States Environmental Protection Agency
(-)-Apparicine at KNApSAck
[https://chem.nlm.nih.gov/chemidplus/name/apparicine Pericalline] at ChemIDplus

1 : Indole alkaloids

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