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Macrocalyxin I.

Hao Shi¹, Yuan Jiang Pan, Shi Hua Wu

¹Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China.

Acta Crystallographica. Section C, Crystal Structure Communications

|January 10, 2002

Summary

A diterpenoid isolated from Rabdosia macrocalyx forms an extensive crystal network. This natural compound utilizes hydrogen bonds between its hydroxy and carboxy groups for crystal stabilization.

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Area of Science:

Natural Product Chemistry
Organic Chemistry
Crystallography

Background:

Rabdosia macrocalyx is a plant source of bioactive natural products.
Diterpenoids are a class of organic compounds with diverse biological activities.
Understanding the crystal structure of natural products aids in elucidating their properties.

Purpose of the Study:

To characterize the diterpenoid 2-[1,2,3,4,4a,4b,5,6,7,8,8a,9-dodecahydro-7-hydroxy-4b,8,8-trimethylphenanthren-2-yl]propenoic acid.
To investigate the intermolecular interactions and crystal packing of this natural product.
To explore the role of functional groups in crystal network formation.

Main Methods:

Isolation of the diterpenoid from Rabdosia macrocalyx.
Chemical structure elucidation using spectroscopic methods (implied).
X-ray crystallography to determine the crystal structure and hydrogen bonding patterns.

Main Results:

The compound 2-[1,2,3,4,4a,4b,5,6,7,8,8a,9-dodecahydro-7-hydroxy-4b,8,8-trimethylphenanthren-2-yl]propenoic acid (C20H30O3) was isolated.
The molecule features hydroxy and carboxy groups acting as hydrogen bond donors and acceptors.
Two intermolecular O-H...O hydrogen bonds were identified, creating a network linking each molecule to four neighbors.

Conclusions:

The isolated diterpenoid exhibits a propensity for forming extensive hydrogen-bonded networks in the solid state.
The specific arrangement of functional groups dictates the crystal packing and network architecture.
This structural insight contributes to the understanding of diterpenoid crystal chemistry.

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