Taxine alkaloids

Taxine A
Skeletal formula of Taxine A
Taxine A
Names
IUPAC name
2α,13α-Diacetoxy-7β,10β-dihydroxy-9-oxo-2(3→20)-abeotaxa-4(20),11-dien-5α-yl (2R,3S)-3-(dimethylamino)-2-hydroxy-3-phenylpropanoate
Other names
(1R,2S,3E,5S,7S,8S,10R,13S)-2,13-Diacetoxy-7,10-dihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.14,8]hexadeca-3,11-dien-5-yl (2R,3S)-3-(dimethylamino)-2-hydroxy-3-phenylpropanoate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C35H47NO10/c1-18-24(44-19(2)37)15-23-26(45-20(3)38)14-22-17-35(6,32(42)30(40)28(18)34(23,4)5)27(39)16-25(22)46-33(43)31(41)29(36(7)8)21-12-10-9-11-13-21/h9-14,23-27,29-31,39-41H,15-17H2,1-8H3/b22-14+/t23-,24-,25-,26-,27-,29-,30+,31+,35-/m0/s1
    Key: KOTXAHKUCAQPQA-MCBQMXOVSA-N
  • CC1=C2C(C(=O)C3(CC(=CC(C(C2(C)C)CC1OC(=O)C)OC(=O)C)C(CC3O)OC(=O)C(C(C4=CC=CC=C4)N(C)C)O)C)O
Properties
C35H47NO10
Molar mass 641.751 g·mol−1
Melting point 204-206 °C[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Taxine B
Skeletal formula of Taxine B
Taxine B
Names
IUPAC name
10β-Acetoxy-1,2α,9α-trihydroxy-13-oxotaxa-4(20),11-dien-5α-yl (3R)-3-(dimethylamino)-3-phenylpropanoate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C33H45NO8/c1-18-23(36)17-33(40)29(38)27-19(2)24(42-25(37)16-22(34(7)8)21-12-10-9-11-13-21)14-15-32(27,6)30(39)28(41-20(3)35)26(18)31(33,4)5/h9-13,22,24,27-30,38-40H,2,14-17H2,1,3-8H3
    Key: XMZFIBDTPOUHMW-UHFFFAOYSA-N
  • CC1=C2C(C(C3(CCC(C(=C)C3C(C(C2(C)C)(CC1=O)O)O)OC(=O)CC(C4=CC=CC=C4)N(C)C)C)O)OC(=O)C
Properties
C33H45NO8
Molar mass 583.722 g·mol−1
Melting point 115 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Taxine alkaloids, which are often named under the collective title of taxines, are the toxic chemicals that can be isolated from the yew tree.[2][3] The amount of taxine alkaloids depends on the species of yew, with Taxus baccata and Taxus cuspidata containing the most.[4] The major taxine alkaloids are taxine A and taxine B although there are at least 10 different alkaloids.[5] Until 1956, it was believed that all the taxine alkaloids were one single compound named taxine.[4]

The taxine alkaloids are cardiotoxins with taxine B being the most active.[6] Taxine alkaloids have no medical uses but Paclitaxel and other taxanes that can be isolated from yews have been used as chemotherapy drugs.[7]

  1. ^ Graf, Engelbert; Kirfel, Armin; Wolff, Gerd-Joachim; Breitmaier, Eberhard (1982-02-10). "Die Aufklärung von Taxin A ausTaxus baccata L.". Liebigs Annalen der Chemie. 1982 (2): 376–381. doi:10.1002/jlac.198219820222. ISSN 0170-2041.
  2. ^ Veterinary toxicology : basic and clinical principles. Gupta, Ramesh C. (Ramesh Chandra), 1949- (2nd ed.). Oxford: Academic. 2012. ISBN 9780123859266. OCLC 778786624.{{cite book}}: CS1 maint: others (link)
  3. ^ Miller, Roger W. (July 1980). "A Brief Survey of Taxus Alkaloids and Other Taxane Derivatives". Journal of Natural Products. 43 (4): 425–437. doi:10.1021/np50010a001. ISSN 0163-3864.
  4. ^ a b Cite error: The named reference :0 was invoked but never defined (see the help page).
  5. ^ Constable, Peter D (2016-10-25). Veterinary medicine : a textbook of the diseases of cattle, horses, sheep, pigs and goats. Hinchcliff, Kenneth W. (Kenneth William), 1956-, Done, Stanley H.,, Grünberg, Walter,, Preceded by: Radostits, O. M. (11th ed.). St. Louis, Mo. ISBN 9780702070587. OCLC 962414947.{{cite book}}: CS1 maint: location missing publisher (link)
  6. ^ Alloatti, G.; Penna, C.; Levi, R. C.; Gallo, M. P.; Appendino, G.; Fenoglio, I. (1996). "Effects of yew alkaloids and related compounds on guinea-pig isolated perfused heart and papillary muscle". Life Sciences. 58 (10): 845–854. doi:10.1016/0024-3205(96)00018-5. ISSN 0024-3205. PMID 8602118.
  7. ^ Muriel, Le Roux (2016-11-26). Navelbine® and Taxotère® : histories of sciences. Gueritte, Françoise. London. ISBN 9780081011379. OCLC 964620092.{{cite book}}: CS1 maint: location missing publisher (link)