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Atalaphylline.

Suchada Chantrapromma, Nawong Boonnak, Ibrahim Abdul Razak

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

Atalaphylline, an acridone alkaloid from Atalantia monophylla, was structurally characterized. Its crystal structure reveals fused rings, specific substituent conformations, and intermolecular hydrogen bonding forming screw chains.

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Area of Science:

Natural Product Chemistry
Crystallography
Organic Chemistry

Background:

Atalantia monophylla Corrêa is a mangrove plant known to produce bioactive compounds.
Acridone alkaloids represent a significant class of natural products with diverse pharmacological properties.
Understanding the three-dimensional structure of natural products is crucial for elucidating their biological activity.

Purpose of the Study:

To isolate and characterize the acridone alkaloid atalaphylline from Atalantia monophylla.
To determine the crystal structure of atalaphylline.
To analyze the molecular conformation, hydrogen bonding, and intermolecular interactions in the crystal state.

Main Methods:

Isolation of atalaphylline from Atalantia monophylla.
Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.
Analysis of intra- and intermolecular hydrogen bonds and π-π interactions.

Main Results:

Atalaphylline, identified as 1,3,5-trihydroxy-2,4-bis-(3-methyl-but-2-enyl)acridin-9(10H)-one, was successfully isolated.
The crystal structure revealed a planar core with specific conformations of the prenyl substituents.
Intramolecular hydrogen bonds formed S(5) and S(6) ring motifs, while intermolecular hydrogen bonds and π-π stacking mediated crystal packing.

Conclusions:

The crystal structure of atalaphylline provides detailed insights into its solid-state arrangement.
The identified hydrogen bonding and π-π interactions are key factors governing the crystal packing.
This structural characterization contributes to the understanding of acridone alkaloid chemistry and their physical properties.