“…Their structures were elucidated by NMR, IR, and HRESIMS analyses (see pages S1–S21 in the Supporting Information). The known compounds were identified as senaetnine ( 4 ), [7] 2‐angeloyloxy‐5,8‐dihydroxypresilphiperfolane ( 5 ), [8] caffeic acid ( 6 ), [9] methylcaffeate ( 7 ), [10] and lupeol ( 8 ) [11] by comparison of their spectroscopic data with literature data.…”
Section: Resultsmentioning
confidence: 99%
“…In conclusion, the CH 3 OH−CH 2 Cl 2 (1 : 1) root and stem bark extracts of S. mannii afforded the new silphiperfolanol angelate ester umutagarananol ( 1 ), the macrocyclic pyrrolizidine alkaloids umutagarinine A and B ( 2 and 3 ) along with the known secondary compounds senaetnine ( 4 ), [7] 2‐angeloyloxy‐5,8‐dihydroxypresilphiperfolane ( 5 ), [8] caffeic acid ( 6 ), [9] methylcaffeate ( 7 ), [10] and lupeol ( 8 ) [11] . The configuration of senaetnine ( 4 ) was determined to be 7 R ,12 R ,13 R using NAMFIS analysis.…”
Three new compounds, the silphiperfolanol angelate ester umutagarananol (1), the macrocyclic pyrrolizidine alkaloids umutagarinine A and B (2–3), and five known secondary metabolites (4–8) were isolated from the CH2Cl2−MeOH (1 : 1) extract of the roots and the stem bark of Solanecio mannii (Hook. f.) (Asteraceae). The isolated compounds were characterized by NMR and IR spectroscopic, and mass spectrometric analyses, whereas the relative stereochemistry of 4 was established by NAMFIS‐based combined computational and solution NMR analysis. Synthetic modification of 5 provided two new compounds, 2‐angeloyloxy‐4,8‐epoxypresilphiperfolane (9) and 2‐angeloyloxy‐4,8‐epoxypresilphi‐perfolane (10). The crude extracts and the isolated constituents showed weak antibacterial activities (EC50 0.7–13.3 mM) against the Gram‐negative Escherichia coli and the Gram‐positive Bacillus subtilis. Compounds 2, 3 and 4 exhibited strong cytotoxicity against MCF‐7 human breast cancer cells, with EC50 values of 35.6, 21.7 and 12.5 μM, respectively.
“…Their structures were elucidated by NMR, IR, and HRESIMS analyses (see pages S1–S21 in the Supporting Information). The known compounds were identified as senaetnine ( 4 ), [7] 2‐angeloyloxy‐5,8‐dihydroxypresilphiperfolane ( 5 ), [8] caffeic acid ( 6 ), [9] methylcaffeate ( 7 ), [10] and lupeol ( 8 ) [11] by comparison of their spectroscopic data with literature data.…”
Section: Resultsmentioning
confidence: 99%
“…In conclusion, the CH 3 OH−CH 2 Cl 2 (1 : 1) root and stem bark extracts of S. mannii afforded the new silphiperfolanol angelate ester umutagarananol ( 1 ), the macrocyclic pyrrolizidine alkaloids umutagarinine A and B ( 2 and 3 ) along with the known secondary compounds senaetnine ( 4 ), [7] 2‐angeloyloxy‐5,8‐dihydroxypresilphiperfolane ( 5 ), [8] caffeic acid ( 6 ), [9] methylcaffeate ( 7 ), [10] and lupeol ( 8 ) [11] . The configuration of senaetnine ( 4 ) was determined to be 7 R ,12 R ,13 R using NAMFIS analysis.…”
Three new compounds, the silphiperfolanol angelate ester umutagarananol (1), the macrocyclic pyrrolizidine alkaloids umutagarinine A and B (2–3), and five known secondary metabolites (4–8) were isolated from the CH2Cl2−MeOH (1 : 1) extract of the roots and the stem bark of Solanecio mannii (Hook. f.) (Asteraceae). The isolated compounds were characterized by NMR and IR spectroscopic, and mass spectrometric analyses, whereas the relative stereochemistry of 4 was established by NAMFIS‐based combined computational and solution NMR analysis. Synthetic modification of 5 provided two new compounds, 2‐angeloyloxy‐4,8‐epoxypresilphiperfolane (9) and 2‐angeloyloxy‐4,8‐epoxypresilphi‐perfolane (10). The crude extracts and the isolated constituents showed weak antibacterial activities (EC50 0.7–13.3 mM) against the Gram‐negative Escherichia coli and the Gram‐positive Bacillus subtilis. Compounds 2, 3 and 4 exhibited strong cytotoxicity against MCF‐7 human breast cancer cells, with EC50 values of 35.6, 21.7 and 12.5 μM, respectively.
“…From the analysis by GC-MS of white solid Cn2 ( Figure 4 ), two triterpenes were determined: α – amyrin ( 3 ) and β – amyrin ( 4 ) ( Figure 3 ). These compounds have been reported in plants of the Ericaceae, Balanophoraceae, and Combretaceae families and there have been studies of their anti-inflammatory and antibacterial activity ( Malca Garcia et al., 2015 ; Matulevich et al., 2016 ; Salih et al., 2018 ). Figure 4 GC-MS total ion chromatogram (TIC) of Cn2 and 3 - mass spectrum of α-amyrin ( 3 ); 4 – mass spectrum of β-amyrin ( 4 ).…”
“…These known compounds include: Cyclooctasulfur ( 2 ), lup-20(29)-en-3-triacontanoate ( 3 ) [10], lupeol ester (reported for the first time from Cordia genus), 1-(26-hydroxyhexacosanoyl)glycerol ( 4 ) [11], glyceryl-1-hexacosanoate ( 5 ) [12], which are monoglycerides and this is the first report of monoglycerol from Cordia genus. The other known compounds are betulinic acid ( 6 ) [13], lupenone ( 7 ) [14], β -amyrone ( 8 ) [15], lupeol ( 9 ) [16], β -amyrin ( 10 ) [17], allantoin ( 11 ) [18], 2′-(4-hydroxyphenyl)ethylpropanoate ( 12 ) [19] and stigmasterol glycoside ( 13 ) [20]. The chemical structures of the hemi-synthetic derivatives, that is, Cordicerol A ( 14 ) and Cordicerol B ( 15 ), are also presented in Figure 1.…”
Chemical investigation of Cordia millenii, Baker resulted in the isolation of a new depsidone, cordidepsine (1), along with twelve known compounds including cyclooctasulfur (2), lup-20(29)-en-3-triacontanoate (3), 1-(26-hydroxyhexacosanoyl)glycerol (4), glyceryl-1-hexacosanoate (5) betulinic acid (6), lupenone (7), β-amyrone (8), lupeol (9), β-amyrin (10), allantoin (11), 2′-(4-hydroxyphenyl)ethylpropanoate (12) and stigmasterol glycoside (13). Hemi-synthetic reactions were carried out on two isolated compounds (5 and 6) to afford two new derivatives, that is, cordicerol A (14) and cordicerol B (15), respectively. The chemical structures of all the compounds were established based on analysis and interpretation of spectroscopic data such as electron ionization mass spectrometry (EI–MS), high resolution electrospray ionization mass spectrometry (HR-ESI–MS), fast atom bombardment mass spectrometry (FAB–MS), one dimension and two dimension nuclear magnetic resonance (1D and 2D-NMR) spectral data as well as X-ray crystallography (XRC). Lupeol ester derivatives [Lup-20(29)-en-3-triacontanoate (3)], monoglycerol derivatives [1-(26-hydroxyhexacosanoyl)glycerol (4) and glyceryl-1 hexacosanoate (5)] were isolated for the first time from Cordia genus while sulfur allotrope [cyclooctasulfur (2)] was isolated for the first time from plant origin. Biological assays cordidepsine (1) exhibited significant anti-HIV integrase activity with IC50 = 4.65 μM; EtOAc extract of stem barks, EtOAc fraction of roots and leaves were not toxic against 3T3 cells.
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