Novel Triterpenes and Bioactive Compounds Isolated from Smilax canariensis Brouss. ex Willd

The aerial parts of Smilax canariensis Brouss. ex Willd., an endemic plant species of the Canary Islands and Madeira, were chemically investigated, resulting in the isolation of multiple known and novel compounds. These include known flavonol glycosides: quercetin-3-O-rutinoside, rutin (7), quercetin-3-O-rutinoside decaacetate (7a), kaempferol-3-O-rutinoside nonaacetate, nicotiflorin acetate (8), 2-O-p-coumaroylglycerol triacetate (10), and trans-resveratrol (9). Additionally, a new sterol, 24,24-dimethy-5α-cholesta-7,25-dien-3-one (1), and two novel dammarane-type triterpenes, 24-hydroxy-24-methyl-dammara-20,25-dien-3-one (2) and 3-acetyl-25-methyl-dammara-20,24-diene (3), were identified. In addition, stigmasterol, sitosterol, and stigmast-4-en-3-one (4) were obtained. The structural elucidation of these compounds was achieved via 1D and 2D NMR spectroscopy, mass spectrometry, and comparison with literature data. This study provides the first phytochemical profile of S. canariensis and highlights its potential as a source of bioactive compounds for pharmacological applications.