Steroidal lactones from Withania somnifera, an ancient plant for novel medicine

Abstract

Withania somnifera, commonly known as Ashwagandha, is an important medicinal plant that has been used in Ayurvedic and indigenous medicine for over 3,000 years. In view of its varied therapeutic potential, it has also been the subject of considerable modern scientific attention. The major chemical constituents of the Withania genus, the withanolides, are a group of naturally occurring C28-steroidal lactone triterpenoids built on an intact or rearranged ergostane framework, in which C-22 and C-26 are appropriately oxidized to form a six-membered lactone ring. In recent years, numerous pharmacological investigations have been carried out into the components of W. somnifera extracts. We present here an overview of the chemical structures of triterpenoid components and their biological activity, focusing on two novel activities, tumor inhibition and antiangiogenic properties of withaferin A and the effects of withanolide A on Alzheimer's disease. The most recent attempts in biotechnological production of withanolides are also discussed.

Figure 1

The basic structure of withanolides.

Figure 2

Overview of the most important steps in the withanolide biosynthetic pathway.

Figure 3

Structure of withaferin A.

Figure 4

Different structures of withanolides.

Figure 5

Ashwagandhanolide, a new compound isolated from W. somnifera.

Figure 6

Different withanamides (A-I) isolated from W. somnifera fruits.