The use of 13C and ¹H-NMR in the structural elucidation of a new Nor-lupane triterpene

Junges, Mario Jose; Fernandes, João B.; Vieira, Paulo; Silva, Maria Fátima das G. Fernandes da; Filho, Edson Rodrigues

doi:10.1590/s0103-50531999000400011

Cited by 7 publications

(5 citation statements)

References 4 publications

(4 reference statements)

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“…This study contributed to increase the knowledge on the leaf chemical composition of Eugenia florida by complementing previously reported data, 3,[5][6][7] as well as assessed its antioxidant and cytotoxic potential. It was possible to detect fourteen triterpenoids through a detailed analysis of their trimethylsylil derivative mass fragmention pathways on GC-MS and eighteen polyphenolic compounds identified with basis on their mass fragmentation patterns by UFLC/DAD/ ESI-Ion Trap-MS n .…”

Section: Discussionsupporting

confidence: 62%

“…3 The ethanol leaf extract showed antimicrobial activity 3 and insecticide activity was demonstrated for methanol extracts from several parts of the plant. 4 Chemical studies on the leaves composition revealed the presence of mono-and sesquiterpenes in the essential oil, 5 triterpene acids and some of their glucosides, 2,6,7 and polyphenolics. 3 This article describes a comprehensive chemical study of the ethanol leaf extract of E. florida, its antioxidant and cytotoxic activities.…”

Section: Introductionmentioning

confidence: 99%

POLYPHENOL AND TRITERPENOID CONSTITUENTS OF Eugenia florida DC. (MYRTACEAE) LEAVES AND THEIR ANTIOXIDANT AND CYTOTOXIC POTENTIAL

Santos¹,

Gomes²,

Mazzei³

et al. 2018

Quim. Nova

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Leaves of Eugenia florida DC. have been used in folk medicine as hypotensive, hypoglycemic, antipyretic and for gastrointestinal disorders, among others. In this study dried leaves were extracted with ethanol and the extract was partitioned with hexane, CHCl 3 , EtOAc, BuOH and water to afford triterpenoid-and polyphenol-rich fractions which were analyzed by GC-MS and UFLC-DAD-ESI-Ion Trap-MS n. All fractions were tested against the proliferation of leukemic K562 and human melanoma SK-Mel-28 cell lines and for their ability to scavenge DPPH radical. Twenty-nine compounds were fully identified (among triterpenic and phenolic acids, flavonol-and dihydroflavonol-monoglyclosides) based on mass fragmentation patterns and comparison to standards and/or literature data. The ability to scavenge DPPH radical resulted in the following order: BuOH ≈ EtOAc > crude extract ≈ Water >> CHCl 3 >> hexane; with the two most active reaching half of the TBHQ control potency (EC 50 6.59 ± 0.03 µg mL-1). On testing against the proliferation of K562 and SK-Mel-28 cell lines, the most significant inhibitions were achieved on the former by the crude extract (IC 50 12 µg mL-1) and the hexane and EtOAc fractions at 15 µg mL-1 .

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“…Likewise, the absorption bands at ν max 2900 and 1480 are observed, indicating the presence of the C-H and C=C groups respectively. Analysis of its 1 H NMR spectrum shows: A system of three aromatic protons ABX resonating at δ H 7.88 (1H, dd, J=9.0 and 2.0 Hz), 7.05 (1H, d, J=9, 0 Hz) and 7.69 (1H, d, J=2.0) corresponding to H-6 ', H-5' and H-2 'and compatible with an aromatic nucleus substituted with an isoflavone [45]. Two protons in singlet form each resonating at δ H 6.44 (1H, d, J=2 Hz) and 6.34 (1H, d, J=2 Hz) attributable respectively to the meta H-6 and H-8 protons of the trisubstituted A ring, Three signals of three protons each as a singlet at δH 3.96 (3H, s); 3.86 (3H, s) and 3.84 (3H, s) attributable to the methoxyls OMe-7, OMe-4' and OMe-3, respectively.…”

Section: Chemical Analysismentioning

confidence: 99%

Inhibitory Effect and Antimicrobial Activity of Secondary Metabolites of <i>Khaya Senegalensis</i> (Desr.) A. Juss. (Meliaceae)

Nganso¹,

Tchana²,

Kahouo³

et al. 2020

SJC

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This present study investigates the in vitro inhibitory effect and antimicrobial activity of secondary metabolites isolated from the roots of Khaya senegalensis, a plant of the Meliaceae family. Khaya senegalensis is widely used in traditional medicine for the treatment of various illnesses such as: fever, stomach ache, diarrhea, dysentery and anemia. The chemical study of the extract with CH 2 Cl 2-MeOH (1:1) led to the isolation of five compounds: Alphitolic acid (1); Epigouanic acid (2); Methyl angolensate (3); Rohituca-3 (4) and 5, 6, 7, 3′, 4′-pentamethoxyflavone or Sinensetin (5). Alphitolic acid (1), Rohituca-3 (4) and 5, 6, 7, 3′, 4′-pentamethoxyflavone or Sinensetin (5) were isolated from the roots of this plant for the first time. The structures of the isolated compounds have been elucidated on the basis of spectroscopic analysis and a comparison of their spectral data with those reported in the literature. The results of the antibiogram tests showed that the strain of Escherichia coli is sensitive to all the antibiotics tested except Ceftazidime, a Cephalosporin. The Staphylococcus aureus strain is resistant to almost all the antibiotics tested except Amikacin, an aminoglycoside. This is because the enzymes diffuse through the inter and intraspecific transmission of genes through a plasmid. The antibiogram made it possible to establish the sensitivity profile of the strains tested with regard to certain antibiotics. The antimicrobial tests carried out showed that the inhibitory effect of the compounds isolated from Khaya senegalensis on the four bacterial strains tested at the concentration of 25 mg/mL positively influenced at least one of the microbial strains. However, compounds 1, 2 and 3 did not show any bacterial growth inhibitory activity against Proteus vulgaris. MIC obtained for microbiological tests varied between 0.097 and 0.195 mg/mL for the most sensitive strains of Escherichia coli and Pseudomonas aeruginosa, which revealed the highest antibacterial powers. Furthermore, these results therefore show a great variability in the bacteriostatic qualities of the compounds with respect to the different strains. The two Grampositive strains of Staphylococcus aureus are more sensitive than the other Gram-negative bacterial strains tested. From the antibacterial activity, it appears that the compounds isolated from this plant have a bactericidal activity against Escherichia coli and Pseudomonas aeruginosa. This bactericide could justify their use in herbal medicine against bacterial infections.

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“…The betulinic acid ( Figure 1) is a known triterpenoid isolated from various organs and species of plants, including flowering Eugenia DC [Junges, 1999]. This metabolite shows inhibitory activity on growth of human melanoma cells [Pisha et al, 1995], and replication of the AIDS virus [Evers et al 1996;Soler et al, 1996].…”

Section: Introductionmentioning

confidence: 99%

Analysis of the Presence of the Betulinic Acid in the Leaves of Eugenia florida by Using the Technique GC/MS, GC/FID and HPLC/DAD: A Seasonal and Quantitative Study

Barreto¹,

Feliciano²,

Nascimento³

et al. 2013

Column Chromatography

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“…Em relação aos triterpenos, os ácidos não glicosilados com esqueleto ursano, oleanano e lupano (FRIGHETTO et al, 2005) são mais comuns em Myrtaceae, embora saponinas triterpênicas já tenham sido descritas na família (GALLO et al, 2006;DJOUKENG et al, 2005;JUNGES et al, 1999).…”

Section: Myrtaceaeunclassified

Estudo fitoquímico e biológico do cambucá Plinia edulis (Vell.) Sobral - Myrtaceae

Ishikawa¹

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The use of 13C and ¹H-NMR in the structural elucidation of a new Nor-lupane triterpene

Cited by 7 publications

References 4 publications

POLYPHENOL AND TRITERPENOID CONSTITUENTS OF Eugenia florida DC. (MYRTACEAE) LEAVES AND THEIR ANTIOXIDANT AND CYTOTOXIC POTENTIAL

Inhibitory Effect and Antimicrobial Activity of Secondary Metabolites of <i>Khaya Senegalensis</i> (Desr.) A. Juss. (Meliaceae)

Analysis of the Presence of the Betulinic Acid in the Leaves of Eugenia florida by Using the Technique GC/MS, GC/FID and HPLC/DAD: A Seasonal and Quantitative Study

Estudo fitoquímico e biológico do cambucá Plinia edulis (Vell.) Sobral - Myrtaceae

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The use of 13C and ¹H-NMR in the structural elucidation of a new Nor-lupane triterpene

Cited by 7 publications

References 4 publications

POLYPHENOL AND TRITERPENOID CONSTITUENTS OF Eugenia florida DC. (MYRTACEAE) LEAVES AND THEIR ANTIOXIDANT AND CYTOTOXIC POTENTIAL

Inhibitory Effect and Antimicrobial Activity of Secondary Metabolites of &lt;i&gt;Khaya Senegalensis&lt;/i&gt; (Desr.) A. Juss. (Meliaceae)

Analysis of the Presence of the Betulinic Acid in the Leaves of Eugenia florida by Using the Technique GC/MS, GC/FID and HPLC/DAD: A Seasonal and Quantitative Study

Estudo fitoquímico e biológico do cambucá Plinia edulis (Vell.) Sobral - Myrtaceae

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Inhibitory Effect and Antimicrobial Activity of Secondary Metabolites of <i>Khaya Senegalensis</i> (Desr.) A. Juss. (Meliaceae)