¹H and ¹³C NMR characterization of new cycloartane triterpenes from Mangifera indica

Abstract

From the stem bark of Mangifera indica, seven cycloartane-type secondary metabolites were isolated. Compound 1 has been isolated for the first time from M. indica, whereas compounds 2 (2a and 2b, as an epimeric mixture), 3, and 4 are new triterpenoid-type cycloartanes. Unambiguous (13) C and (1) H NMR assignments for these compounds and the known compounds mangiferonic acid (compound 5), isomangiferolic acid (compound 6), ambolic acid (compound 7), and friedelin (compound 8) are reported; the latter because full NMR data for these compounds are not available in the literature.

Chemical profiling and antioxidant activity of Bolivian propolis

“…The compound 29 , with a more restricted occurrence, was reported from Mangifera indica . This tree is cultivated in Santa Cruz and Yungas for its fruits and might be one of the sources of this compound.…”

“…46 The compound 29, with a more restricted occurrence, was reported from Mangifera indica. 37,47 This tree is cultivated in Santa Cruz and Yungas for its fruits and might be one of the sources of this compound. Other cycloartane triterpenes have been described from Rapanea, 41 Euphorbia, 36 Gardenia 38 and Aglaia species, 39 among others.…”

Characterisation of triterpenes and new phenolic lipids in Cameroonian propolis

“…The sample of propolis was extracted with 70% ethanol and the extract obtained was partitioned with n-hexane, ethyl acetate and n-butanol, respectively. Fractionation of the n-hexane and ethyl acetate extracts using repeated chromatographic procedures led to the isolation of a mixture of thirteen alk(en)ylphenols (1-13), including the three new structures (8), (12) and (13), along with α-amyrin (14) (Hernández Vázquez et al, 2012;Basyuni et al, 2006), β-amyrin (15) (Basyuni et al, 2006;Mahato and Kundu, 1994), lupeol (16) (Basyuni et al, 2006;Thanakijcharoenpath and Theanphong, 2007), cycloartenol (17) (Kamisako et al, 1987;Zhu et al, 2012), mangiferonic acid (18) (Escobedo-Martinez et al, 2012), ambonic acid (19) (Da Silva et al, 2005), mangiferolic acid (20) (Escobedo-Martinez et al, 2012), ambolic acid (21) (Escobedo-Martinez et al, 2012), and isomangiferolic acid (22) (Escobedo-Martinez et al, 2012). Fractionation of the n-butanol extract afforded a mixture of nine alk(en)ylresorcinols (23-31), including the new structure (30) ( Figs.…”

“…indica, Anacardiaceae) (Anjaneyulu and Radhika, 2000;Cojocaru et al, 1986;Escobedo-Martinez et al, 2012;Knödler et al, 2008;Kienzle et al, 2014), a resin-producing plant widely used in honey production in Cameroon and throughout tropical Africa (Nguemo Dongock et al, 2004;Focho et al, 2009). The hypothesis that mango is used as a botanical source of phytochemicals for our sample needs to be confirmed with further field studies (i.e., observation of bees foraging) and comparative analyses of the chemical composition, if collected, of mango resin and of propolis used in local hives.…”

Cyclocuneatol and Cuneatannin, New Cycloartane Triterpenoid and Ellagitannin Glycoside from Euphorbia cuneata

“…The NOESY cross peaks of H‐3/H‐5, H 3 ‐28, and H 3 ‐30 and H 3 ‐28/H‐17 designated the α‐orientation of these protons. Moreover, H‐29 exhibited a cross peak to H‐8 and H‐18, suggesting their β‐configuration . Thus, the cyclocuneatol structure was assigned as cycloart‐20‐en‐3β‐ol.…”