Three New Triterpenoid Saponins from Ardisia crenata

Abstract

Three new triterpenoid saponins, ardisicrenoside I (1), ardisicrenoside J (2), and ardisicrenoside M (3), along with eight known compounds, were isolated from the roots of Ardisia crenata Sims. Their structures were elucidated as 16α‐hydroxy‐30,30‐dimethoxy‐3β‐O‐{β‐D‐xylopyranosyl‐(1→2)‐β‐D‐glucopyranosyl‐(1→4)‐[β‐D‐glucopyranosyl‐(1→2)]‐α‐L‐arabinopyranosyl}‐13β,28‐epoxyoleanane (1), 16α‐hydroxy‐30,30‐dimethoxy‐3β‐O‐{α‐L‐rhamnopyranosyl‐(1→2)‐β‐D‐glucopyranosyl‐(1→4)‐[β‐D‐glucopyranosyl‐(1→2)]‐α‐L‐arabinopyranosyl}‐13β,28‐epoxyoleanane (2), 30,30‐dimethoxy‐16‐oxo‐3β‐O‐{β‐D‐xylopyranosyl‐(1→2)‐β‐D‐glucopyranosyl‐(1→4)‐[β‐D‐glucopyranosyl‐(1→2)]‐α‐L‐arabinopyranosyl}‐13β,28‐epoxyoleanane (3), ardisiacrispin A (4), ardisiacrispin B (5), ardisicrenoside B (6), ardisicrenoside A (7), ardisicrenoside H (8), ardisicrenoside G (9), cyclamiretin A‐3β‐O‐β‐D‐xylopyranosyl‐(1→2)‐β‐D‐glucopyranosyl‐(1→4)‐α‐L‐arabinopyranoside (10), and cyclamiretin A‐3β‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐β‐D‐glucopyranosyl‐(1→4)‐α‐L‐arabinopyranoside (11) by means of chemical and spectral analysis, and their cytotoxicities were evaluated in vitro.

Techniques for the analysis of pentacyclic triterpenoids in medicinal plants

“…Although compounds can be identified through GC, analyzing triterpenes, including the analytes with low volatility, remains a challenge because it requires transformation in trimethylsilyl derivatives. Liu et al [78] evaluated the cytotoxic activities of triterpenes (ardisicrenoside O, P, and Q) on two human cancer cell lines, with the application of GC-MS to qualification of the compounds. They discovered that ardisicrenoside Q, which was a pentacyclic triterpenoids existed in the roots of Ardisia crenata, had significant cytotoxicity.…”

Anti‐inflammatory activity of a new lactone isolated from the leaves of Ardisia crenata Sims

“…[2] A. crenata Sims is a genus of plants in the myrtle family Ardisia, and its roots are recorded in the Chinese Pharmacopoeia (2020) edition for a commonly used as Chinese medicine "Zhushagen". The roots are commonly used for the treatment of sore throat, dysmenorrhea and rheumatism, [3][4][5] and research on chemical constituents showed that triterpenoid saponins, isocoumarins, phenols and benzoquinones were the main chemical constituents in A. crenata Sims, [6][7][8] and studies on these chemical constituents found that triterpenoid saponins had better anti-tumour activity. [9] Moreover, lactones are rarely isolated in A. crenata Sims, and this kind of active ingredients often have better antiinflammatory activities.…”

Two New Phenolic Glycosides with Lactone Structural Units from Leaves of Ardisia crenata Sims with Antibacterial and Anti-Inflammatory Activities

“…The Ardisia crenata Sims is a common evergreen shrub belonging to Ardisia of Myrsinaceae with red fruits at maturity [ 3 ]. In China, the roots of the red-fruited A. crenata Sims are used as a traditional Chinese medicine “Zhushagen” [ 4 ], which is widely used for the treatment of respiratory infections, toothache, arthralgia, menstrual problems, and fertility regulation [ 5 , 6 , 7 ]. These pharmacological activities are often closely related with different kinds of chemical constituents from the roots of A. crenata Sims.…”