Triterpene Esters: Natural Products from Dorstenia arifolia (Moraceae)

Abstract

The phytochemical study of Dorstenia arifolia Lam. (Moraceae) has led to the identification of 18 triterpenes esterified by fatty acids, five triterpenes without esterification, 12 triterpenes esterified by acetic acid, together with a known furanocoumarin: α-amyrin (1), β-amyrin (2) α-amyrin acetate (3) β-amyrin acetate (4), α-amyrin octanoate (5), β-amyrin octanoate (6), α-amyrin decanoate (7), β-amyrin decanoate (8), α-amyrin dodecanoate (9), β-amyrin dodecanoate (10), α-amyrin tetradecanoate (11), β-amyrin tetradecanoate (12), α-amyrin hexadecanoate (13), β-amyrin hexadecanoate (14), glutinol (15), glutinyl acetate (16), 11-oxo-α-amyrin (17), 11-oxo-β-amyrin (18), 11-oxo-α-amyrin acetate (19), 11-oxo-β-amyrin acetate (20) 11-oxo-α-amyrin octanoate (21) 11-oxo-β-amyrin octanoate (22), 11-oxo-α-amyrin decanoate (23), 11-oxo-β-amyrin decanoate (24) 11-oxo-α-amyrin dodecanoate (25) 11-oxo-β-amyrin dodecanoate (26), ursa-9(11),12-dien-3-yl acetate (27), oleana-9(11),12-dien-3-yl acetate (28), ursa-9(11),12-dien-3-yl decanoate (29), oleana-9(11),12-dien-3-yl decanoate (30), 12,13-epoxyolean-3-yl acetate (31), 12,13-epoxyolean-9(11)en-3-yl acetate (32), taraxeryl acetate (33), lupenyl acetate (34), lanosta-8,24-dien-3-yl acetate (35) and psoralen (36). The identification of the triterpene compounds isolated as isomeric mixtures obtained from the hexane extract was based mainly in mass spectra and 13C-NMR data. The long-chain alkanoic acid esters of the triterpenes α- and β-amyrin; 11-oxo-α- and 11-oxo-β-amyrin; ursa- and olean-9(11),12-dien-3-yl; have not been reported before in the literature as constituents of the Dorstenia genus.

Anti-Inflammatory Triterpenoids from the Stems of Microtropis Fokienensis

“…Its IR spectrum showed absorption bands for hydroxyl groups (3425 cm ) and an α,β-unsaturated ketone system (1655 cm −1 ). The molecular formula was determined to be C 30 Therefore, 1 was suggested to have an urs-12-ene frame and the α,β-unsaturated ketone system in ring C was similar to 3β-hydroxyurs-12-en-11-one, except for the presence of one more oxymethine [16][17][18]. The MS fragmentations at m/z 248, where each bond was cleaved at the α,β-unsaturated ketone system in ring C, indicated that the other hydroxyl group was seemed to be located in either ring D or E. (Figure 2) [19].…”

New ursane triterpenoids from Ficus pandurata and their binding affinity for human cannabinoid and opioid receptors

“…The known compounds were identified by analysing the spectroscopic data (1D and 2D NMR) and comparing their data with those in the literature to be α -amyrin acetate ( 1 ) (Virgilio et al 2015), α -amyrin ( 2 ) (Virgilio et al 2015), 3 β -acetoxy-20-taraxasten-22-one ( 3 ) (Ramadan et al 2009; Ahmed 2010), 3 β -acetoxy-11 α -methoxy-olean-12-ene ( 4 ) (Kuo and Chiang 2000; Mallavadhani et al 2006; Barbosa et al 2010), 3 β -acetoxy-11 α -methoxy-12-ursene ( 5 ) (Mathias et al 2000; Barbosa et al 2010), 11-oxo- α -amyrin acetate ( 6 ) (Fingolo et al 2013), 11-oxo- β -amyrin acetate ( 7 ) (Fingolo et al 2013), palmitic acid ( 8 ) (Ajoku et al 2015), stigmast-4,22-diene-3,6-dione ( 9 ) (Itokawa et al 1973), stigmast-4-ene-3,6-dione ( 10 ), stigmasterol ( 12 ) (Mohamed and Ibrahim 2007; Kamboj and Salujai 2011; Chaturvedula and Prakash 2012), β -sitosterol ( 13 ) (Al-Musayeib et al 2013), stigmast-22-ene-3,6-dione ( 14 ) (Wei et al 2004), stigmastane-3,6-dione ( 15 ) (Wei et al 2004; Lim et al 2005), 3 β ,21 β -dihydroxy-11 α -methoxy-olean-12-ene ( 16 ) (Cáceres-Castillo et al 2008), 3 β -hydroxy-11 α -methoxyurs-12-ene ( 18 ) (Fujita et al 2000), 6-hydroxystigmast-4,22-diene-3-one ( 19 ) (Kontiza et al 2006; Georges et al 2006), 6-hydroxystigmast-4-ene-3-one ( 20 ) (Kontiza et al 2006; Georges et al 2006) and β -sitosterol-3- O - β -D-glucopyranoside ( 22 ) (Khatun et al 2012). …”

Antidiabetes Activities Extract Hexane From the Peels of Artocarpus Camansi Blanco Fruit

“…Based on the fragmentation pattern it is suspected that a compound is a group of amyrin compounds. Based on the typical MS on the chromatogram are: 468, 426, 218 (100), 203 (44), and 189 (17) [10]. Fragment pattern is similar to the β-amyrin acetate compound.…”