Coumaroyl triterpene lactone, phenolic and naphthalene glycoside from stem bark of Diospyros angustifolia

Pathak, Arunendra; Kulshreshtha, D. K.; Maurya, Rakesh

doi:10.1016/j.phytochem.2004.03.010

Cited by 19 publications

(8 citation statements)

References 8 publications

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“…The detailed isolation procedure for 1 – 6 is provided in the Supporting Information. All the isolated compounds were characterized by 1 H‐ and 13 C‐NMR spectroscopy and MS, and the data were in agreement with the reported literature data .…”

Section: Methodssupporting

confidence: 88%

A validated high‐performance thin‐layer chromatography method for the identification and simultaneous quantification of six markers from Platanus orientalis and their cytotoxic profiles against skin cancer cell lines

Khan

Sangwan

Dar

et al. 2013

J of Separation Science

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Betulinic acid (1), betulinic acid-3-acetate (2), 3-acetylbetulinaldehyde (3), oleanolic acid-3-acetate (4), 3-β-hydroxy-28,19-β-olenolide (5), and β-sitosterol (6) were isolated from Platanus orientalis and a high-performance thin-layer chromatography method was developed for their simultaneous quantification. The markers were first derivatized on the chromatogram with ceric ammonium sulfate and then high-performance thin-layer chromatography densitometry was carried out. Chromatographic separation of these markers was carried out on silica gel 60 plates using a ternary solvent system n-hexane/toluene/acetone (6:3.5:1 v/v/v) as a mobile phase. For marker 1, a deuterium (D2) lamp and wavelength of 420 nm was used. A tungsten (W) lamp was used for markers 2 and 3 at 550 nm and for 4-6 at 500 nm. The method was validated for accuracy, precision, LOD, and LOQ. All calibration curves showed a good linear relationship (r > 0.9919). The precision evaluated by an intra- and interday study showed RSDs < 2.51% and accuracy validation recovery between 95.54 and 99.33% with RSDs < 1.55%. The successful application of the validated method showed 1 as the most abundant component (4.63%) and 5 (0.017%) the least. The markers displayed a significant cytotoxic effect against human keratinocyte, mouse melanoma, and human skin epithelial carcinoma cancer cells by using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay.

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Section: Methodssupporting

confidence: 88%

A validated high‐performance thin‐layer chromatography method for the identification and simultaneous quantification of six markers from Platanus orientalis and their cytotoxic profiles against skin cancer cell lines

Khan

Sangwan

Dar

et al. 2013

J of Separation Science

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“…One new naphthalene glycoside, 5-hydroxydianellin 286, and a known naphthalene glycoside, dianellin 287, were isolated from roots of the daylily Hemerocallis fulva 'Kwanzo' Kaempfer (278). Diospyrosonaphthoside 288 was isolated from an ethanolic extract of the stem bark of Diospyros angustifolia (279), and plicataloside 289, an O,O-diglycosylated naphthalene derivative, was isolated from Aloe plicatilis (280).…”

Section: Glycosides Of Naphthalene Derivativesmentioning

confidence: 99%

Astonishing diversity of natural surfactants: 5. Biologically active glycosides of aromatic metabolites

Dembitsky

2005

Lipids

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This review article presents 342 aromatic glycosides, isolated from and identified in plants and microorganisms, that demonstrate different biological activities. They are of great interest, especially for the medicinal and/or pharmaceutical industries. These biologically active natural surfactants are good prospects for the future chemical preparation of compounds useful as antioxidant, anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been classified into several groups, including simple aromatic compounds, stilbenes, phenylethanoids, phenylpropanoids, naphthalene derivatives, and anthracene derivatives.

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“…Resonances in the H-COSY spectrum of 4 revealed the connectivity from HÀC(5') to HÀC (7'), and also showed couplings between MeÀC(2) and HÀC (3), and HÀC (6) and HÀC (7). The HMBCspectrum of isodiospyrol A (4) established the partial structure from C(1) to C(8); demonstrating correlations from MeÀC(2) H-atoms to C(1), C(2), and C(3); HÀC (3) to C(4); HOÀC(4) to C(4), C(4a), and C(3); HÀC (6) to C(4a) and C (8); and HÀC (7) to C(5) and C(8a). The HMBC spectral data also assisted in partial structure assembling from C(1') to C (8'), from which the following correlations were seen; HOÀC(1') to C(1'), C(2'), and C(8'a); MeÀC(3') H-atoms to C(2'), C(3'), and C(4'); HÀC(4') to C(5') and MeÀC(3') C-atom; HÀC(5') to C(4'), C(4'a), and C(8'a); and both HÀC(6') and HÀC (7') to C(8').…”

mentioning

confidence: 94%

Bioactive Deoxypreussomerins and Dimeric Naphthoquinones fromDiospyros ehretioides Fruits: Deoxypreussomerins May Not Be Plant Metabolites But May Be from Fungal Epiphytes or Endophytes

Prajoubklang

Sirithunyalug

Charoenchai

et al. 2005

C&B

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Deoxypreussomerin derivatives, palmarumycins JC1 (1) and JC2 (2), and two dimeric naphthoquinones, isodiospyrin (3) and its new derivative isodiospyrol A (4), were isolated from dried fruits of Diospyros ehretioides. Structures of the isolated compounds were elucidated by spectroscopic analyses. Palmarumycins were not found in the extract of freshly collected fruits; however, they were present in dried fruit extract. The absence of palmarumycins in fresh fruits of D. ehretioides, together with the chemotaxonomic point of view, we proposed that palmarumycins JC1 (1) and JC2 (2) are more likely to be fungal metabolites, i.e., endophytes or epiphytes. The isolation of palmarumycins 1 and 2 from dried D. ehretioides fruits could be reproducible; both plant samples collected in the years 2002 and 2004 provided the same result, and, therefore, symbiont fungal strains should be specific to the plant host, D. ehretioides, and they can grow on the fruits during drying the sample. Palmarumycin JC1 (1) did not exhibit antimalarial, antifungal, antimycobacterial, and cytotoxic activities. Palmarumycin JC2 (2) exhibited antimalarial (IC50 4.5 microg/ml), antifungal (IC50 12.5 microg/ml), antimycobacterial (MIC 6.25 microg/ml), and cytotoxic (IC50 11.0 microg/ml for NCI-H187 cell line) activities. In our bioassay systems, isodiospyrin (3) did not exhibit antimycobacterial, antifungal, antimalarial, and cytotoxic activities. Isodiospyrol A (4) exhibited antimalarial (IC50 2.7 microg/ml) and antimycobacterial (MIC 50 microg/ml) activities, but was inactive towards Candida albicans. Compound 4 also exhibited cytotoxicity against BC cells (IC50 12.3 microg/ml), but not towards KB and Vero cell lines.

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Coumaroyl triterpene lactone, phenolic and naphthalene glycoside from stem bark of Diospyros angustifolia

Cited by 19 publications

References 8 publications

A validated high‐performance thin‐layer chromatography method for the identification and simultaneous quantification of six markers from Platanus orientalis and their cytotoxic profiles against skin cancer cell lines

A validated high‐performance thin‐layer chromatography method for the identification and simultaneous quantification of six markers from Platanus orientalis and their cytotoxic profiles against skin cancer cell lines

Astonishing diversity of natural surfactants: 5. Biologically active glycosides of aromatic metabolites

Bioactive Deoxypreussomerins and Dimeric Naphthoquinones fromDiospyros ehretioides Fruits: Deoxypreussomerins May Not Be Plant Metabolites But May Be from Fungal Epiphytes or Endophytes

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