ent-5α,3,15-Dioxodolabr-4(18)-ene-16,18-diol

Area of Science:

• Natural Product Chemistry
• Organic Chemistry
• Crystallography

Background:

• Ceriops tagal is a mangrove species known to produce various bioactive compounds.
• Dolabrane diterpenoids represent a class of natural products with diverse chemical structures.
• Understanding the structural and conformational properties of natural products is crucial for their potential applications.

Purpose of the Study:

• To isolate and characterize a novel dolabrane diterpenoid from Ceriops tagal.
• To elucidate the three-dimensional structure and conformation of the isolated compound.
• To investigate the intermolecular interactions and crystal packing of the compound.

Main Methods:

• Isolation of the compound using chromatographic techniques.
• Structure elucidation using spectroscopic methods (e.g., NMR, MS).
• Single-crystal X-ray diffraction analysis to determine the crystal structure and molecular conformation.

Main Results:

• A dolabrane diterpenoid, C(20)H(30)O(4), was successfully isolated from Ceriops tagal.
• The compound exhibits a unique conformation with one cyclohexane ring in a half-chair and two in chair conformations.
• Intramolecular hydrogen bonding forms an S(6) ring motif, and crystal packing involves screw chains stabilized by O-H⋯O and C-H⋯O interactions.

Conclusions:

• The study reports the isolation and full structural characterization of a novel dolabrane diterpenoid.
• The conformational analysis reveals specific structural features influencing the molecule's properties.
• The crystal structure provides insights into the intermolecular forces governing the compound's solid-state organization.