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Cysteine sulfoxide derivatives in Petiveria alliacea
1Department of Chemistry, State University of New York at Albany, NY, Albany 12222, USA.
Phytochemistry
|October 31, 2001
Summary
Two diastereomers of S-benzyl-L-cysteine sulfoxide were isolated from Petiveria alliacea roots. These compounds, found in all plant parts, are most abundant in the root, marking the first natural occurrence of S-benzylcysteine derivatives.
Area of Science:
- Natural Product Chemistry
- Phytochemistry
- Organic Chemistry
Background:
- Petiveria alliacea is a medicinal plant with a history of traditional use.
- Sulfur-containing compounds are known to contribute to the bioactivity of plants.
- The chemical constituents of P. alliacea, particularly its sulfur compounds, require further elucidation.
Purpose of the Study:
- To isolate and characterize S-benzyl-L-cysteine sulfoxide diastereomers from Petiveria alliacea.
- To determine the distribution and content of these compounds in different parts of the plant.
- To report the first natural occurrence of S-benzylcysteine derivatives.
Main Methods:
- Isolation of diastereomers using chromatographic techniques.
- Structure elucidation and absolute configuration determination via NMR, MALDI-HRMS, IR, and CD spectroscopy.
- Quantification of compounds in root, stem, and leaves.
Main Results:
- Two diastereomers of S-benzyl-L-cysteine sulfoxide, R(S) and S(S), were successfully isolated.
- The S(S) diastereomer was found to be predominant in all plant parts analyzed.
- Compound content varied significantly, with roots exhibiting the highest concentration (up to 2.97 mg g(-1) fr. wt).
- Trace amounts of S-benzylcysteine were also detected (<10 microg g(-1) fr. wt).
Conclusions:
- This study confirms the presence and characterizes S-benzyl-L-cysteine sulfoxide diastereomers in Petiveria alliacea.
- The findings highlight the root as the primary reservoir for these compounds within the plant.
- This research constitutes the initial report on the natural existence of S-benzylcysteine derivatives in nature.
