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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
ent-Labdane diterpenoid lactone stereoisomers from Andrographis paniculata
Lixia Chen1, Huajie Zhu, Rui Wang
1School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, PR China.
Journal of Natural Products
|March 25, 2008
Summary
Three new ent-labdane diterpenoid lactones were isolated from Andrographis paniculata. These compounds and related derivatives were tested for antiproliferative activity against human leukemia HL-60 cells.
Area of Science:
- Natural Products Chemistry
- Pharmacology
- Medicinal Chemistry
Background:
- Andrographis paniculata is a medicinal plant with a history of traditional use.
- Ent-labdane diterpenoids are a class of natural products with diverse biological activities.
- Previous studies have indicated the potential of these compounds in various therapeutic areas.
Purpose of the Study:
- To isolate and characterize new ent-labdane diterpenoid lactone stereoisomers from Andrographis paniculata.
- To investigate the antiproliferative activities of these isolated compounds and related derivatives against human leukemia cells.
- To revise the stereochemical configuration of a known compound based on spectroscopic data.
Main Methods:
- Extraction of aerial parts of Andrographis paniculata using 85% ethanol.
- Isolation and purification of ent-labdane diterpenoid lactone stereoisomers.
- Structure elucidation using spectroscopic data analyses (NMR) and computational methods (B3LYP/6-311++G(2d,p)//B3LYP/6-31G* level using GIAO method).
- Assessment of antiproliferative activity using human leukemia HL-60 cell line.
Main Results:
- Isolation of two pairs of ent-labdane diterpenoid lactone stereoisomers (1-4), including three new compounds (1-3).
- Structural identification and revision of stereochemistry for compound 4.
- Determination of antiproliferative activities, with andrographolide (7) and isoandrographolide (12) showing significant activity (GI50 values of 9.33 and 6.30 μM, respectively).
Conclusions:
- New ent-labdane diterpenoid lactones were successfully isolated and characterized from Andrographis paniculata.
- The study provides valuable insights into the structure-activity relationships of these compounds regarding antiproliferative effects.
- Andrographolide and isoandrographolide demonstrate potent antiproliferative activity, suggesting their potential as leads for leukemia therapy.
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