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


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.


Boswellia serrata gum 5-Lipoxygenase inhibitor Medicinal activity Hydrogen bonding 


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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

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