Bullatacin

Bullatacin is a bis(tetrahydrofuranoid) fatty acid lactone found in some fruits from Annonaceae family. It is a member of the class of compounds known as acetogenins.[1][2][3]

(+)-Bullatacin
Bullatacin.svg
Names
Other names
Annonareticin; Rolliniastatin 2; Squamocin G
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3/t28-,30+,31-,32+,33+,34+,35+,36+/m0/s1 checkY
    Key: MBABCNBNDNGODA-LUVUIASKSA-N checkY
  • InChI=1/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3/t28-,30+,31-,32+,33+,34+,35+,36+/m0/s1
    Key: MBABCNBNDNGODA-LUVUIASKBE
  • O=C\1O[C@H](/C=C/1C[C@H](O)CCCCCCCCCC[C@@H](O)[C@@H]3O[C@@H]([C@@H]2O[C@H](CC2)[C@@H](O)CCCCCCCCCC)CC3)C
Properties
C37H66O7
Molar mass 622.928 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

ReferencesEdit

  1. ^ H. Naito; E. Kawahara; K. Maruta; M. Maeda; S. Sasaki (1995). "The First Total Synthesis of (+)-Bullatacin, a Potent Antitumor Annonaceous Acetogenin, and (+)-(15,24)-bis-epi-Bullatacin". Journal of Organic Chemistry. 60 (14): 4419–4427. doi:10.1021/jo00119a019.
  2. ^ H.-W. Chih; H.-F. Chiu; K.-S. Tang; F.-R. Chang; Y.-C. Wu (2001). "Bullatacin, a potent antitumor annonaceous acetogenin, inhibits proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction". Life Sciences. 69 (11): 1321–1331. doi:10.1016/S0024-3205(01)01209-7. PMID 11521756.
  3. ^ Y.-H. Hui; J. K. Rupprecht; Y. M. Liu; J. E. Anderson; D. L. Smith; C.-J. Chang; J. L. McLaughlin (1989). "Bullatacin and Bullatacinone: Two Highly Potent Bioactive Acetogenins from Annona bullata". Journal of Natural Products. 52 (3): 463–477. doi:10.1021/np50063a002. PMID 2778448.