Advertisement

Journal of Chemical Crystallography

, Volume 41, Issue 5, pp 697–702 | Cite as

Synthesis and Structural Proof of a Potent 5-Lipoxygenase Inhibitor

  • Devipriya Balu
  • Kumaradhas Poomani
  • Kalyanam Nagabushanam
  • Sridhar Balasubramanium
  • Rajendran Ramanujam
  • Majeed Muhammed
Original Paper
  • 118 Downloads

Abstract

5-Lipoxygenase inhibitor 3-O-acetyl-9,11-dehydro-β-boswellic acid was detected in the extract of Boswellia serrata gum resulting from unstable 11-hydroxy precursor. It was reported more potent than other Boswellic acids in its inhibition of 5-Lipoxygenase. Here, we report the method of conversion of 3-acetoxy-β-boswellic acid to 3-O-acetyl-9,11-dehydro-β-boswellic acid, and the crystal structure of later. This compound crystallizes in orthorhombic space group P212121 with cell parameters of a = 12.726(1) Å, b = 16.597(1) Å, c = 27.332(2) Å, α = β = γ = 90°, V = 5772.7(5) Å3, D c = 1.143 Mg/m3, and Z = 8. The X-ray structure investigation indicates that the rings A, B, D and E are exhibit chair and the ring C adopts a distorted half chair conformation. The conformational difference of the two structures in the arrangement is due to crystal packing of 3-O-acetyl-9,11-dehydro-β-boswellic acid. The molecular packing is stabilized by C–H···O and O–H···O types of hydrogen bonding interactions.

Graphical Abstract

Synthesis and crystal structure analysis of 5-Lipoxygenase Inhibitor 3-O-acetyl-9,11-dehydro-β-boswellic acid are reported. Rings A, B, D and E of the inhibitor adopt chair conformation and the C-ring exhibit a distorted half chair conformation. The molecular packing is stabilized by C–H···O and O–H···O types of hydrogen bonding interactions.

Keywords

Boswellia serrata gum 5-Lipoxygenase inhibitor Medicinal activity Hydrogen bonding 

References

  1. 1.
    Ammon HPT (2006) Planta Medica 72:1100–1116CrossRefGoogle Scholar
  2. 2.
    Safayahi H, Mack T, Sabieraj J, Anazodo M, Subramanian LR, Ammon HPT (1992) J Pharm Exp Ther 26:1143–1146Google Scholar
  3. 3.
    Sailer ER, Hoernlein RF, Subramanian LR, Ammon HPT, Safayhi H (1996) Arch Pharm Pharm Med Chem 329:54–56CrossRefGoogle Scholar
  4. 4.
    Schweizer S, Von Brocke AFW, Boden SE, Bayer E, Ammon HPT, Safayhi H (2000) J Nat Prod 63:1058–1061CrossRefGoogle Scholar
  5. 5.
    Rajnikant V, Gupta VK, Rangari VD, Bapat SR, Agarwal RB, Gupta R (2001) Cryst Res Technol 36:93–100CrossRefGoogle Scholar
  6. 6.
    Virgil SC, Jenkins PR, Wilson AJ, Garcia Romero MD (2006) N-bromosuccinimide in e-EROS encyclopedia of reagents for organic synthesis. John Wiley & Sons Google Scholar
  7. 7.
    Bruker (2000) APEX-II and SAINT. Bruker AXS Inc, Madison, WI, USAGoogle Scholar
  8. 8.
    Sheldrick GM (1997) SHELXS97, Program for the structure solution. University of Gottingen, GermanyGoogle Scholar
  9. 9.
    Sheldrick GM (1997) SHELXL97, Program for the crystal structure refinement. University of Gottingen, GermanyGoogle Scholar
  10. 10.
    Johnson CK (1976) ORTEPII, ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, TN, USAGoogle Scholar
  11. 11.
    Duax WL, Weeks CM, Rohrer DC (1976) In: Eliel EL, Allinger N (eds) Topics in stereochemistry. John Wiley, New York, pp 271–383Google Scholar
  12. 12.
    Shishkin OV (2000) J Struct Chem 41:383–387CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Devipriya Balu
    • 1
  • Kumaradhas Poomani
    • 1
  • Kalyanam Nagabushanam
    • 2
  • Sridhar Balasubramanium
    • 3
  • Rajendran Ramanujam
    • 2
  • Majeed Muhammed
    • 2
  1. 1.Department of PhysicsPeriyar UniversitySalemIndia
  2. 2.Research & DevelopmentSabinsa CorporationEast WindsorUSA
  3. 3.Laboratory of X-Ray CrystallographyIndian Institute of Chemical TechnologyHyderabadIndia

Personalised recommendations