Pentacyclic Triterpenoids from Maytenus cuzcoina

Abstract

Phytochemical analysis of the root bark extract of Maytenus cuzcoina (Celastraceae) led to the isolation and characterization of sixteen triterpenoids with a 6/6/6/6/6 pentacyclic system, including the new 22-hydroxy-29-methoxy-3-tetradecanoate-olean-12-ene, and 3,24-epoxy-29-methoxy-2,3,6trihydroxy-D:A-friedelane that is reported for the first time as a natural product. This is the first instance of the isolation of a tetradecanoate triterpene ester from a Celastraceae species. The structures were elucidated on the basis of spectrometric and spectroscopic methods, including 1D and 2D NMR techniques.

A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies

“…Two new oleanane triterpenes, 3 β ,19 α -dihydroxyolean-12-en-29-oic acid ( 96 ) and 3 α ,19 α -dihydroxyolean-12-en-29-oic acid ( 97 ), were obtained from M. austyoyunnanensis [ 14 ]. Compound 3-oxo-11 α -methoxyolean-12-ene ( 98 ) was obtained from the extracts of the roots of M. spinosa [ 24 ], while 22 α -hydroxy-29-methoxy-3 β -tetradecanoate-olean-12-ene ( 99 ) was separated from the root bark extracts of M. cuzcoina [ 31 ]. The new compound maytefolin B ( 100 ) was separated from the leaves of a Brazilian medicinal plant, M. ilicifolia [ 44 ].…”

“…Compounds 1 α ,2 α ,6 β ,8 β ,9 α ,15-hexacetoxy-4 β -hydroxy-3 β ,13-[2′-(3-carboxybutyl)] nicotinicacid-dicarbo-lactone- β -dihydroagarofuran ( 254 ), 1 α ,2 α ,9 α ,15-tetracetoxy-4 β ,6 β -dihydroxy-8-oxo,3 β ,13-[4′-(3-carboxybutyl)]nicotinicacid-dicarbolactone- β -dihydroagarofuran ( 255 ), 1 α ,2 α ,9 α ,15-tetracetoxy-4 β ,6 β ,8 β -trihydroxy-3 β ,13-[4′-(3-carboxybutyl)] nicotinicacid-dicarbolactone- β -dihydroagarofuran ( 256 ) and 1 α ,2 α ,8 β ,9 α ,15-pent acetoxy-4 β ,6 β -dihydroxy-3 β ,13-[4′-(3-carboxybutyl)] nicotinicaciddicarbolactne- β -dihydroagarofuran ( 257 ) were isolated from the leaves of M. spinosa [ 65 ]. Compounds 4-deoxyalatamine ( 258 ), 1- O -benzoyl-1-deacetyl-4-deoxy-alatamine ( 259 ), 1,2- O -dibenzoyl-1,2-deacetyl-4-deoxyalatamine ( 260 ) and 4-deoxyisowilfordine ( 261 ) were obtained from an ethyl acetate extract of M. oblongata stems [ 31 ] ( Table 6 and Figure 6 ).…”

“…Compounds 15α-hydroxy-tingenone (30), 15-dehydro-pristimerin (31), vitideasin (32) and 20β-hydroxy-scutione (33) were separated from the roots of M. vitis-idaea [24]. Six new compounds, including 7-oxo-7, 8-dihydro-scutione (34), 6,23-dioxo-7,8-dihydropristimerol-23-oic Acid (35), 23-nor-blepharodol (36), 3-methoxy-6-oxo-tingenol-23-oic Acid (37), retusonine (38) and were isolated from the root bark of M. retusa [25].…”

“…A new triterpenoid, 12,16-dihydroxyfriedelan-3-one (48), was isolated from an ethyl acetate extract of M. oblongata [30]. Compounds 3β,24β-epoxy-29-methoxy-2α,3α,6α-trihydroxy-D:A-friedelane (49) and 3β,24β-epoxy-29-methoxy-2α,3α,6α-triacetoxy-D:A-friedelane (49a) were obtained from the root bark extracts of M. cuzcoina [31]. Three new pentacyclic triterpenoids, friedel-1-en-3,16-dione (50), 1α,29-dihydroxyfriedelan-3-one (51) and 16β,28,29trihydroxyfriedelan-3-one (52) have been separated from M. robusta [32].…”