A New Cytotoxic Stigmasterone from Agathis Macrophylla

Abstract

A new stigmasterone 7α,15α-dihydroxystigmast-4-en-3-one (1), along with fifteen known compounds was isolated from the EtOAc and n-BuOH fractions of the EtOH extract of Agathis macrophylla. The structure of these compounds 1-16 were established mainly by spectroscopic analysis and by comparison of the spectroscopic data with those reported for structurally related compounds. The isolated compounds 1-8 were screened for cytotoxicity in A549 tumor cell line using RSB assay. Compounds 1 and 2 displayed moderate cytotoxicity against A549 tumor cell line with IC50 value of 36.5 and 16.0 μmol/L, respectively.

Phytochemistry, Chemotaxonomy, and Biological Activities of the Araucariaceae Family—A Review

“…Yet, in order to verify if this is a general tendency, more phytochemical studies must be carried out both on the same exemplar and on other samples coming from different areas of Italy and of the world. In addition, in all the cases, more exemplars coming from different areas were studied [ 8 , 9 , 10 , 12 , 13 , 16 , 17 , 18 , 19 , 22 , 23 , 24 , 25 ] except for A. borneensis samples coming only from Malaysia [ 11 ] and A. microstachya samples coming only from Australia [ 8 , 20 ]. For what concerns the studied organs, leaves represent the most studied ones.…”

“…Right about this point, essential oil components and polar fraction components have been evidenced in the genus. Yet, only for six species i.e., A. atropurpurea [ 8 , 9 ], A. australis [ 8 , 9 ], A. macrophylla [ 8 , 16 , 17 , 18 , 19 ], A. microstachya [ 8 , 20 ], A. ovata [ 8 , 9 ] and A. robusta [ 8 , 9 , 22 , 23 , 24 , 25 ], the phytochemical studies regarded both kinds of natural compounds. Indeed, for four species i.e., A. borneensis [ 11 ], A. dammara [ 12 ], A. moorei [ 8 ], and A. philippinensis [ 21 ], only the essential oil composition was studied whereas for two species i.e., A. alba [ 6 , 7 ] and A. lanceolata [ 14 , 15 ], only the polar fraction composition was analyzed.…”

“…Some diterpenes have also been reported for this genus from A. lanceolata [ 14 , 15 ], A. macrophylla from China [ 16 ] and from Fiji [ 18 , 19 ] and the resin of A. microstachya [ 20 ]. Only in one case i.e., A. macrophylla , some triterpenes have also been noticed [ 17 ]. In two cases i.e., A. dammara from Philippines [ 13 ] and A. robusta from United Kingdom [ 23 ], the exact polar fraction composition was not reported since only a phytochemical screening was performed.…”

“…In some cases i.e., A. atropurpurea leaves from Australia [ 8 ], A. australis leaves [ 8 ], A. macrophylla from Australia [ 8 ], A. microstachya leaves [ 8 ], A. moorei [ 8 ], A. ovata from Australia [ 8 ], and A. robusta from Australia [ 8 ], [α] D and NMR analyses accompanied the GC ones. Indeed, for the analysis of the polar fraction metabolites, SE was the only method for the extraction of these compounds, CC, TLC, LC, and HPLC, together or separated, were the methods for the separation procedure of the compounds and [α] D , IR, NMR, and MS, together or separated, were the methods for the identification procedure of the compounds [ 6 , 7 , 9 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 22 ].…”

“…7α,15α-dihydroxystigmast-4-en-3-one and 3β,22,23-trihydroxystigmast-5-en-7-one, isolated from A. macrophylla , have shown medium cytotoxic effects against A549 (adenocarcinomic human alveolar basal epithelial) tumor cell lines with IC 50 values equal to 36.5 and 16.0 μmol/L [ 17 ].…”