Cytotoxic Homoisoflavonoids from &lt;i&gt;Ophiopogon japonicus&lt;/i&gt; Tubers

Dang, Nguyen Hai; Chung, Nguyen Dinh; Tuan, Hoang Duong; Hiep, Nguyen Tuan; Dat, Nguyen Tien

doi:10.1248/cpb.c16-00743

Cited by 16 publications

(17 citation statements)

References 15 publications

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“…The major IR absorption bands indicated a carboxyl group (1726 cm -1 ) and hydroxy groups (3420 cm -1 ). Analysis of the 1 H, 13 These findings indicated that the structure of 1 was similar to those of paniculoside-IV. [14] Additionally, the structure of 1 was further confirmed The relativeconfiguration of 1 was determined by analyzing its NOESY data and based generally comparable NMR data with those previously reported.…”

Section: Cytotoxic Assaymentioning

confidence: 77%

“…[12] Compounds 1-5 were also evaluated for their cytotoxic effect against A549 (lung), MCF-7 (breast carcinoma), Hep3B (hepatoma), and PC3 (prostate) human cancer cell lines using 3-(4,5dimethylthiazolyl-2)-2,5-diphenyltetrazoliumbromide (MTT) assays for 48h (at concentrations of 10, 30, 50, and 100 µM). [13] Among the tested compounds, moderate effects were observed with compounds 1 and 3 on Hep3B and PC3 cells with IC50 values of 49.3, 55.6 µM and 34.6, 61.0 µM, respectively (at the highest concentration tested 100 μM). However, compounds 2 and 5 were not toxic to A549, Hep3B, and PC3 cells, while 4 was inactivity against all four cell lines, comparing to the positive control, camptothecin (IC50 = 1.5 µM).…”

Section: Cytotoxic Assaymentioning

confidence: 92%

“…This assay was determined under steady-state conditions as described using the protocol of Dang et al [13] 3. RESULTS AND DISCUSSION Compound 1 was obtained as a white, amorphous powder, with a negative optical rotation   24 D α -77.2 (c 0.2, MeOH).…”

Section: Cytotoxic Assaymentioning

confidence: 99%

“…Its IR spectrum showed characteristic absorption bands for hydroxy groups (3400 cm −1 ), a carbonyl group (1750 cm −1 ), a double bond (1640 cm −1 ), and an ether group (1350 cm −1 ). The signals in the 1 H and 13 (Table 2). Moreover, the 1D NMR signals of δC 87.82 (CH, C-3)/δH 3.01 (1H, d, J = 3.0 Hz, H-3) suggested the presence of an oxygenated methinegroup, and the COSY, HMBC experiments indicated an oxymethine group was located at C-3 of the aglycone (Fig.…”

Section: Cytotoxic Assaymentioning

confidence: 99%

“…1 H and13 C NMR spectroscopic data (δ ppm) of 2 in CD3OD MHz. Assignments were made using the HSQC, HMBC, COSY, and ROESY spectra.…”

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confidence: 99%

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Anti‐inflammatory and cytotoxic activities of constituents from Wedelia trilobata (L.) Hitchc.

Thảo

Binh

Luyen³

et al. 2019

Vietnam Journal of Chemistry

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Using various chromatographic separations, five compounds (1–5) were isolated from a methanol extract of W. trilobata leaves. Their structures were elucidated to be paniculoside‐IV (1), 3‐O‐[β‐D‐glucopyranosyl(1‐4)‐β‐D‐glucoronopyranosyl] oleanolic acid 28‐O‐β‐D‐glucopyranosyl ester (2), 5,7,4'‐trihydroxyflavone (3), apigenin 7‐O‐β‐D‐glucopyranoside (4), and 3,4‐dihydroxy‐cinnamic acid (5), by detailed analysis via spectroscopic techniques (IR, 1D, 2D NMR and ESI‐MS data) as well as comparison with those reported. This is the first report of 2 from Wedelia genus. Furthermore, the effects of the isolated compounds on LPS‐induced NO production in RAW264.7 cells and cytotoxic activity (against A549, MCF‐7, Hep3B, and PC3 cell lines) were also evaluated.

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Section: Cytotoxic Assaymentioning

confidence: 77%

Section: Cytotoxic Assaymentioning

confidence: 92%

Section: Cytotoxic Assaymentioning

confidence: 99%

Section: Cytotoxic Assaymentioning

confidence: 99%

“…1 H and13 C NMR spectroscopic data (δ ppm) of 2 in CD3OD MHz. Assignments were made using the HSQC, HMBC, COSY, and ROESY spectra.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Anti‐inflammatory and cytotoxic activities of constituents from Wedelia trilobata (L.) Hitchc.

Thảo

Binh

Luyen³

et al. 2019

Vietnam Journal of Chemistry

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Homoisoflavonoids profiling of Ophiopogon japonicus by off‐line coupling high‐speed countercurrent chromatography with high‐performance liquid chromatography–diode array detector‒quadrupole time‐of‐flight tandem mass spectrometry

Deng

Tong

et al. 2020

J of Separation Science

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Roots of Ophiopogon japonicus have been used as a functional food ingredient and traditional Chinese medicine for a long time in China. Homoisoflavonoids are one of the major kinds of bioactive compounds in O. japonicus; however, literature data about its homoisoflavonoids profile are scarce because of the complex ingredients with low abundance. Here, homoisoflavonoid fraction was prepared by petroleum ether extraction. Then, a high-speed countercurrent chromatography offline coupling with high-performance liquid chromatography-diode array detectorquadrupole time-of-flight tandem mass spectrometry was developed for systematic identification of homoisoflavonoids. After that, 39 homoisoflavonoids, including 29 homoisoflavanone and 10 homoisoflavone, were unambiguously or tentatively identified, while 12 of them were reported in O. japonicus for the first time. Finally, eight available homoisoflavonoids were sensitively, precisely, and accurately determined by standard calibration curves, with limit of detection and limit of quantification in the range of 0.05-0.30 μg/mL and 0.12-0.66 μg/mL, relative standard deviation less than 7.3% for intra-and interday variations, and recovery at 94.5-105.2%. Collectively, our developed method is efficient, reliable, and valuable to profile chemical components of complex natural products.

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A pair of homoisoflavonoid analogues (6-aldehydo-isoophiopogonanone A/6-aldehydo-isoophiopogonanone B) from Ophiopogon japonicus as a tyrosinase inhibitor: inhibitory activity, conformational change and mechanism

Wang

Qin

Wang

et al. 2021

Eur Food Res Technol

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Cytotoxic Homoisoflavonoids from <i>Ophiopogon japonicus</i> Tubers

Cited by 16 publications

References 15 publications

Anti‐inflammatory and cytotoxic activities of constituents from Wedelia trilobata (L.) Hitchc.

Anti‐inflammatory and cytotoxic activities of constituents from Wedelia trilobata (L.) Hitchc.

Homoisoflavonoids profiling of Ophiopogon japonicus by off‐line coupling high‐speed countercurrent chromatography with high‐performance liquid chromatography–diode array detector‒quadrupole time‐of‐flight tandem mass spectrometry

A pair of homoisoflavonoid analogues (6-aldehydo-isoophiopogonanone A/6-aldehydo-isoophiopogonanone B) from Ophiopogon japonicus as a tyrosinase inhibitor: inhibitory activity, conformational change and mechanism

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