Total assignment of 13C and 1H spectra of three isomeric triterpenol derivatives by 2D NMR: an investigation of the potential utility of 1H chemical shifts in structural investigations of complex natural products

Reynolds, William F.; McLean, Stewart; Poplawski, J.; Enríquez, Raúl G.; Escobar, Luis A.; Leon, Ismael

doi:10.1016/s0040-4020(01)87309-9

Cited by 171 publications

(105 citation statements)

References 7 publications

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“…It is reported that flavan-3,4-diols were involved as intermediate substances in flavan-3-ol biosynthesis catalyzed by reductase reaction (Drewes & Roux, 1965). The other isolated compounds were successively identified as 1,2,3-benzenetriol (2), butin (3), 2 000 ,3 000 -dihydroxylupinifolin (4), lupinifolin (5), 8-methoxy-7,3 0 ,4 0 -trihydroxyflavone (6), 7,8,3 0 ,4 0 -tetrahydroxyflavone (7), lupeol (8), stigmasta-5,22-dien-3-one (9), and a mixture of b-sitosterol and stigmasterol by the analysis of their NMR spectra and by comparing with the data reported in the literature (Herath et al, 2009;Mahidol et al, 1997Mahidol et al, , 2002Porter & Foo, 1982;Reynolds et al, 1986). Compounds 1-4 were first isolated herein from the genus Albizia.…”

Section: Discussionmentioning

confidence: 89%

Chemical constituents and biological activities ofAlbizia myriophyllawood

Joycharat

Boonma

Thammavong

et al. 2015

Pharmaceutical Biology

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Context: Albizia myriophylla Benth (Leguminosae) is a medicinal plant widely used in Thailand and other Asian countries as a folk medicine remedy for many ailments. Objective: The objective of this study is to investigate the chemical compositions, antibacterial activity, and cytotoxicity of A. myriophylla wood. Materials and methods: The structure identification of the isolated compounds was established using spectroscopic methods. In vitro antibacterial activity against Streptococcus mutans, Staphylococcus aureus, and Bacillus cereus and the cytotoxicity against KB cells of extracts and compounds from A. myriophylla were performed using broth microdilution and resazurin microplate assays, respectively. The lupinifolin content in A. myriophylla extracts was quantified by high-performance liquid chromatography. Results: A rare flavan-3,4-diol (1) together with eight known compounds (2-9) were isolated from the wood of A. myriophylla. Compounds 4-9 exhibited anti-S. mutans activity, of which lupinifolin (5) was the most potent with an MIC value of 0.98 mg/mL, followed by its dihydroxy derivative 4 with an MIC value of 62.5 mg/mL. Compounds 4 and 5 also displayed marked antibacterial activity against B. cereus and S. aureus (MIC value 15.63-125 mg/mL) and showed strong cytotoxic activity against KB cells (IC 50 value 4.95-12.55 mg/mL). The lupinifolin contents in ethanol extracts from two different collections of this plant originating from central and southern Thailand were 93.85 and 0.04 mg/g, respectively. Conclusion: This is the first report of compounds 1-4 from A. myriophylla. Compounds 4 and 5 showed potent antibacterial and cytotoxic activities compared with other isolates. The anti-S. mutans activity of A. myriophylla extracts seems to be related to the lupinifolin content.

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Section: Discussionmentioning

confidence: 89%

Chemical constituents and biological activities ofAlbizia myriophyllawood

Joycharat

Boonma

Thammavong

et al. 2015

Pharmaceutical Biology

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“…The EtOAc and 1-BuOH-soluble fractions were separated by means of various chromatographic procedures including column chromatography (CC) on silica gel and reversed-phase octadecyl silica gel (ODS) CC, and HPLC, 17 compounds (1-17) being isolated; a new cyanogenic glucoside (1), a new megastigmane glucoside (2) and a new sulfated flavonoid rhamnoside (3), in addition to 14 known compounds, which were identified as lupeol (4), 4) demethoxymatteucinol (5), 5) cryptostrobin (6), 6) betulinic acid (7), 7) β-sitosterol glucoside (8), 8) 2R-prunasin (9), 9) myrciaphenone A (10), 10) 1-feruloyl-β-D-glucopyranoside (11), 11) (3S,5R,6R,7E,9S )-3,5,6,9-tetrahydroxymegastigman-7-ene (12), 12) guaijaverin (13), 13) myricetin 4′-methyl ether 3-O-α-Lrhamnopyranoside (14), 14) myricetrin (15), 15) gallic acid (16) 16) and actinidioionoside (17) 17) by comparing their spectroscopic data with those reported in the literature.…”

Section: Resultsmentioning

confidence: 99%

Taxiphyllin 6′-O-Gallate, Actinidioionoside 6′-O-Gallate and Myricetrin 2″-O-Sulfate from the Leaves of Syzygium samarangense and Their Biological Activities

et al. 2014

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“…As estruturas do lupeol (5) e do β-sitosterol (6) foram identificadas através dos dados fornecidos pelos espectros de RMN de H 1 e de 13 C, comparados com valores descritos na literatura 16 .…”

Section: Resultsunclassified

Constituintes químicos de Zanthoxylum ekmanii (URB.) Alain

Facundo¹,

Silveira²,

Braz-Filho³

et al. 2005

Quím. Nova

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Recebido em 17/2/04; aceito em 9/9/04; publicado na web em 17/2/05 CHEMICAL CONSTITUENTS OF Zanthoxylum ekmanii (URB.) ALAIN. Chemical investigation of Z. ekmanii resulted in the isolation of skimmianine, dictamnine, tembamide, sesamin, lupeol and β-sitosterol. The structures were established by spectroscopic analyses. This is the first report on the phytochemical study of the roots and leaves of Z. ekmanii .

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Total assignment of 13C and 1H spectra of three isomeric triterpenol derivatives by 2D NMR: an investigation of the potential utility of 1H chemical shifts in structural investigations of complex natural products

Cited by 171 publications

References 7 publications

Chemical constituents and biological activities ofAlbizia myriophyllawood

Chemical constituents and biological activities ofAlbizia myriophyllawood

Taxiphyllin 6′-<i>O</i>-Gallate, Actinidioionoside 6′-<i>O</i>-Gallate and Myricetrin 2″-<i>O</i>-Sulfate from the Leaves of <i>Syzygium samarangense</i> and Their Biological Activities

Constituintes químicos de Zanthoxylum ekmanii (URB.) Alain

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