Abstract
A madecassoside-rich fraction obtained from the industrial purification of Centella asiatica leaves afforded a new triterpene glycoside, named isomadecassoside (4), characterized by an ursane-type skeleton and migration of the double bond at Δ20(21) in ring E. The structure of isomadecassoside was established by means of HR-ESIMS and detailed analysis of 1D and 2D NMR spectra, which allowed a complete NMR assignment. Studies on isolated J774A.1 macrophages stimulated by LPS revealed that isomadecassoside (4) inhibited nitrite production at non-cytotoxic concentrations, thus indicating an anti-inflammatory effect similar to that of madecassoside.
Highlights
Centella asiatica (L.) Urban, known as gotu kola or Indian pennyworth, is a perennial herbaceous plant belonging to the family Apiaceae (Umbelliferae)
The structural diversity within these series is given by the number and position of double bonds and the degree of hydroxylation and glycosylation, the predominant members of the class are characterized by a Glucose (Glu)-Glucose (Glu)-Rhamnose (Rha) triglycoside esterifying the carboxylic group at C-28 [8]
A fraction obtained from C. asiatica leaves enriched in triterpenoid glycosides of the madecassoside series was subjected to reverse phase HPLC purification affording the new isomadecassoside (4), together with the known madecassoside (2) and terminoloside
Summary
Centella asiatica (L.) Urban, known as gotu kola or Indian pennyworth, is a perennial herbaceous plant belonging to the family Apiaceae (Umbelliferae). C. asiatica are typically indicated to accelerate healing of skin ulcers and wounds, being able to promote the synthesis of collagen, normalize the hyperproliferation of keratinocytes and restore the natural homeostasis of the epidermis [1,2]. Phytochemical studies on this important medicinal plant have reported several biomolecules such as triterpenes (in the free and glycosylated forms) [3] and flavonoids [4], in addition to volatile components of the essential oils [5,6]. The nomenclature of the several dozens of Centella saponins reported in the
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