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. 2017 Apr-Jun;13(50):293-299.
doi: 10.4103/0973-1296.204549. Epub 2017 Apr 18.

Anti-Differentiation Effect of B, D- Seco limonoids of Swietenia mahogani

Heejung Yang  1 , Mina Choi  2 , Dong Young Lee  2 , Sang Hyun Sung  2
Affiliations

Anti-Differentiation Effect of B, D- Seco limonoids of Swietenia mahogani

Heejung Yang et al. Pharmacogn Mag. 2017 Apr-Jun.

Abstract

Background: Obesity is a pathological state caused by abnormal or excessive accumulation of fat. Swietenia mahogani JACQ., known as West Indian mahogany, is a medium-sized semi-evergreen tree belonging to Meliaceae. Their seeds are used in Indonesian folk medicine as a treatment for hypertension, diabetes, malaria, and it also has anti-feedant activities. The major components of S. mahogani are B, D-seco limonoids, a type of irregular triterpenes are well known.

Objective: We tried to find the bioactive components, which have the inhibitory activity on adipocyte differentiation from the seeds of S. mahogani.

Material and methods: 3T3-L1 cells, derived from mouse preadipocyte, are widely used in studying adipogenesis process. In this study, we used 3T3-L1 cells to find natural products with the inhibitory activity on adipocyte differentiation. S. mahogani seeds were dried and extracted with 100% MeOH.

Results: The methanolic extract was fractionated by bioassay-guided method to give nine B, D-seco limonoids (1-9) with slight structural modifications. Among nine compounds, compounds 4, 6 and 8 exhibited significant inhibitory effects of cell differentiation on 3T3-L1 cells. Those compounds have tigloyl residue at C-3 in common. Besides, compounds with no tigloyl residue at C-3 showed insignificant effect. Nevertheless, not all compounds with tigloyl residue at C-3 exerted significant inhibitory effect.

Conclusion: These results suggested that tigloyl residue at C-3 may play a role in the anti-proliferative activity on a dipogenesis and the refined extract of S. mahogani may have a potential to be developed as a therapeutic agent to treat obesity.

Summary: Nine irregular seco-limonoids were isolated from Swietenia mahogani.Total extract and CHCl3 fraction of S. mahogani showed the significant inhibitory activities on 3T3-L1 cell differentiation.A tigloyl residue at C-3 in an aglycone may play a role in the anti-proliferative activity on adipogenesis.

Keywords: 3T3-L1; Swietenia mahogani; adipogenesis; obesity; seco-limonoid; structure and activity relationship.

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Conflict of interest statement

There are no conflicts of interest.

Figures

Figure 1
Figure 1
The structures of compounds 1-9.
Figure 2
Figure 2
The chromatogram of CHCl3 fraction from S. mahogani analyzed by UPLC-QTOF-MS.
Figure 3
Figure 3
Inhibitory effect of total extract and fractions (A) and compounds 1-9 (B) of S. mahogani seeds on 3T3-L1 differentiation.
None
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