Pentacyclic Triterpenoids from the Medicinal Herb, Centella asiatica (L.) Urban

Abstract

Centella asiatica accumulates large quantities of pentacyclic triterpenoid saponins, collectively known as centelloids. These terpenoids include asiaticoside, centelloside, madecassoside, brahmoside, brahminoside, thankuniside, sceffoleoside, centellose, asiatic-, brahmic-, centellic- and madecassic acids. The triterpene saponins are common secondary plant metabolites and are synthesized via the isoprenoid pathway to produce a hydrophobic triterpenoid structure (aglycone) containing a hydrophilic sugar chain (glycone). The biological activity of saponins has been attributed to these characteristics. In planta, the Centella triterpenoids can be regarded as phytoanticipins due to their antimicrobial activities and protective role against attempted pathogen infections. Preparations of C. asiatica are used in traditional and alternative medicine due to the wide spectrum of pharmacological activities associated with these secondary metabolites. Here, the biosynthesis of the centelloid triterpenoids is reviewed; the range of metabolites found in C. asiatica, together with their known biological activities and the chemotype variation in the production of these metabolites due to growth conditions are summarized. These plant-derived pharmacologically active compounds have complex structures, making chemical synthesis an economically uncompetitive option. Production of secondary metabolites by cultured cells provides a particularly important benefit to manipulate and improve the production of desired compounds; thus biotechnological approaches to increase the concentrations of the metabolites are discussed.

Targeted inhibition of tumor proliferation, survival, and metastasis by pentacyclic triterpenoids: Potential role in prevention and therapy of cancer

“…Asiatic acid (AA) is a pentacyclic triterpenoid derived from the tropical medicinal plant, Centella asiatica (Apiaceae) [17]. Pentacyclic triterpenoids have been found to have wide-ranging pharmacological effects and in particular AA has been shown to reduce inflammation, inhibit tumor cell proliferation, and induce apoptosis through a mitochondria-dependent pathway [18].…”

Relationships Between Chemical Structure and Activity of Triterpenes Against Gram-Positive and Gram-Negative Bacteria

“…These pentacyclic triterpenes (PCTTs) present a basic skeleton which provides a large amount of derivative structures because different positions on their skeleton may be substituted. As result, there are at least 4000 known PCTTs (Dzubak et al, 2006), exhibiting a large spectrum of biological activities (James & Dubery, 2009). Some classes of triterpenes present other skeleton, such as fernane-and lupane-type triterpenes.…”

Antidiabetic activity of Centella asiatica (L.) urbana in alloxan induced Type 1 diabetic model rats

“…It has been used widely in folk medicine for hundreds of years to treat a wide range of illness (Brinkhaus et al 2000). It is used in traditional and alternative medicine due to the wide spectrum of pharmacological activities associated with these secondary metabolites (James and Dubery 2009). It accumulates large quantities of pentacyclic triterpenoid saponins, collectively known as centelloids.…”