Anthraquinones from Vismia species

Carmo, María do; Miraglia, Marina; Mesquita, Antonio A.L.; Jesus, Marisa de Sousa Viana; Varejão, C.; Gottlieb, Otto R.; Gottlieb, Hugo E.

doi:10.1016/0031-9422(81)84067-8

Cited by 22 publications

(8 citation statements)

References 4 publications

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“…Our 1 H NMR data of vismiaquinone (2) were in agreement with those previously reported (do Carmo et al, 1981); however, differences were noticed regarding the chemical shifts of some aromatic protons and carbon atoms reported in the literature. Therefore, unam- biguous 13 C and 1 H NMR assignments (Table II) were achieved with the aid of HSQC and HMBC experiments.…”

Section: Isolation Of Compoundssupporting

confidence: 91%

“…3). Vismiaquinone (2) had first been isolated from the wood of V. japurensis (do Carmo et al, 1981), thereafter from the leaves of V. reichardtiana (Goncalves and Mors, 1981), V. parviflora (Nagem and de Oliveira, 1997), and V . laurentii (Noungoue et al, 2009).…”

Section: Isolation Of Compoundsmentioning

confidence: 99%

“…It was further obtained as a natural product from the wood of V. japurensis (do Carmo et al, 1981), and the berries of V. mexicana and V. cayennensis (Moura Pinheiro et al, 1984). …”

Section: Isolation Of Compoundsmentioning

confidence: 99%

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Anthraquinones from Vismia mexicana

Reyes-Chilpa

Gómez-Cansino

Guzmán-Gutiérrez

et al. 2014

Zeitschrift Für Naturforschung C

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Vismia mexicana (Clusiaceae) is a small tropical tree found from Mexico to Honduras. The CH2Cl2/MeOH extract from the leaves has been reported to have inhibitory properties against reverse transcriptase of human immunodeficiency virus type 1 (HIV-1 RT). In order to characterize some of its chemical constituents, the EtOAc-soluble fraction of this extract was subjected to column chromatography. A new natural product was isolated and designated vismiaquinone D [1-hydroxy-6-methoxy-7,8-(3',3'-dimethyl-pyrano) anthraquinone]. In addition, vismiaquinone was obtained. The structures of vismiaquinone and vismiaquinone D were determined by 1H and 13C NMR spectroscopy, unambiguous assignments were achieved with DEPT, HSQC, and HMBC experiments, and corroborated by X-ray diffraction studies. The isolated anthraquinones were tested against HIV-1 RT. However, none showed relevant activity, suggesting that other compounds in this extract may be responsible for its HIV-1 RT inhibitory properties.

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Section: Isolation Of Compoundssupporting

confidence: 91%

Section: Isolation Of Compoundsmentioning

confidence: 99%

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Anthraquinones from Vismia mexicana

Reyes-Chilpa

Gómez-Cansino

Guzmán-Gutiérrez

et al. 2014

Zeitschrift Für Naturforschung C

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“…Repeated column chromatography of soluble fractions obtained fifteen compounds (1-15) including 1-2 from hexane-soluble fraction, 3-13 from EtOAc-soluble fraction and 14-15 from BuOHsoluble fraction. On the basis of their physicochemical data, and by comparing with those published in the literature, isolated compounds (1-15) were identified as chyrsophanol (1) (Sang et al, 2005), physcion (2) (Carmo et al, 1981), desoxyrhaponticin (3) (Kashiwada et al, 1984), rhapontincin (4) (Yoshiki et al, 1984), resveratrol (5) (Jin et al, 2002), desoxyrhapontigenin (6) (Kashiwada et al, 1984), emodin (7) (Choi et al, 2005), rhapontigenin (8) (Kashiwada et al, 1984), chrysophanol-8-O-E-D-glucopyranoside (9) (Kashiwada et al, 1984), piracetannol-3'-E-D-glucopyranoside (10) (Kashiwada et al, 1984), piceid (11) (Kashiwada et al, 1984), H-viniferin (12) (Ito et al, 1999;Kim et al, 1999), isorhapontin (14) (Artemnika et al, 2004), and emodin-8-O-E-glucopyranoside (15) (Zhang et al, 2005).…”

Section: Resultsmentioning

confidence: 99%

Lipoxygenase inhibitory constituents from rhubarb

et al. 2008

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Phytochemical study on the ethanol extract of rhubarb led to the isolation of fifteen compounds, including five anthraquinones: chrysophanol (1), physcion (2), emodin (7), chrysophanol-8-O-beta-D: -glucopyranoside (9) and emodin-8-O-beta-D: -glucopyranoside (15), and ten stilbenes: desoxyrhaponticin (3), rhaponticin (4), resveratrol (5), desoxyrhapotigenin (6), rhapontigenin (8), piceatannol-3'-O-beta-D: -glucopyranoside (10), piceid (11), epsilon-viniferin (12), ampelopsin B (13) and isorhaponticin (14). Their structures were identified by comparing the physicochemical data with those of published papers. Among the isolated compounds, stilbene derivatives (3-6, 8 and 10-14) showed remarkable inhibitory effect on lipoxygenase with IC(50) values ranging from 6.7 to 74.1 microM. The inhibition kinetics analyzed by Lineweaver-Burk plots found that they were competitive inhibitors with the linoleic acid at the active site of lipoxygenase. In addition, stilbenes exhibited significantly free radical scavenging activity against ABTS(.+) with trolox equivalent activity capacity (TEAC) values ranging from 1.16 to 4.64. Whereas, anthraquinone derivatives (1-2, 7, 9 and 15) neither inhibited lipoxygenase nor scavenged free radical ABTS(.+). These results indicated that stilbene derivatives were considerate to be mainly lipoxygenase inhibitor and free radical scavenger constituents of rhubarb.

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“…Fractions 27–47, eluted with the mixture of cyclohexane/ethyl acetate (9:1) gave 1.3 g of brown residue which was subjected to further column chromatography to yield laurentixanthone (25 mg), 3-methoxyemodine (25 mg); compound C and compound E bivismiaquinone (40 mg). Fraction A eluted with cyclohexane/ethyl acetate (4:1), gave after repetitive column chromatography, kampherol (16 mg), laurentixanthone A (50 mg), 1,7- dihydroxy xanthone (18 mg), vismiaquinone B (50 mg); compound B,, 2-isoprenyl-3-methoxyemodine (22 mg); compound D. The chemical structure of each isolated compound was established on the basis of their NMR spectra (one and two dimensions) [ 2 , 20 ] and data recorded on BRUKER DRX-400 instrument.…”

Section: Methodsmentioning

confidence: 99%

Antimicrobial structure activity relationship of five anthraquinones of emodine type isolated from Vismia laurentii

et al. 2017

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BackgroundAntimicrobial activity of anthraquinone compounds of emodine type has been reported by many authors. These compounds are found in Vismia laurentii (Clusiaceae), a plant used in traditional pharmacopoeia for treatment of microbial infections among others affections. The continuous identification of new compounds has raised the problem of the relation between the structure and antimicrobial properties.ResultsThe yeast growth kinetics parameters were not influenced by the pH variation as it was the case for the other tested bacteria. Fungicidal activities were noted for all molecules while only few of them had bactericidal activities, mostly on Gram positive bacteria. Mathematical model establishing a quantitative relationship between physicochemical properties of molecules and their fungicidal activities were obtained for Candida albicans and showed that physicochemical properties impacting on antifungal activity were polarizability, partition coefficient, molecular weight and hydrogen bond acceptor.ConclusionsThis work demonstrated that the presence of a long aliphatic chain methoxy group substituted in position two of the emodine structure increased the antibacterial properties of the studied compounds. Moreover this antimicrobial property depends on the pH of the environment, and specifically on the polarizability and number of hydrogen bond acceptors of the compound.

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Anthraquinones from Vismia species

Cited by 22 publications

References 4 publications

Anthraquinones from Vismia mexicana

Anthraquinones from Vismia mexicana

Lipoxygenase inhibitory constituents from rhubarb

Antimicrobial structure activity relationship of five anthraquinones of emodine type isolated from Vismia laurentii

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