Chemical Constituents from Leaves of Camellia nitidissima and Their Potential Cytotoxicity on SGC7901 Cells

Qi, Jing; Shi, Ruixia; Yu, Jianming; Li, Yang; Yuan, Shengtao; Yang, Ji-zhu; Hu, Jiang‐Miao; Jia, Ai‐Qun

doi:10.1016/s1674-6384(16)60012-6

Cited by 20 publications

(22 citation statements)

References 7 publications

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“…In brief, 16 chemical constituents were isolated from the leaves of C. nitidissima , and 6 phytochemicals (compound 2, 3, 5, 6, 7 and 10) were first reported in this plant in this study, while other 8 phytochemicals were first reported in this plant in our previous published study ( 11 ). Furthermore, we evaluated the antitumor activity of 16 phytochemicals on 4 different cancer cell lines (3 different cancer types).…”

Section: Introductionmentioning

confidence: 69%

“…The structures of these 16 chemical constituents are shown in Fig. 2 , and the spectra are described as follows: Compound 1: the spectrum was reported previously ( 11 ). Compound 2: C 32 H 50 O 5 1 H-NMR (400 MHz, CDCl 3 -d1) δ:1.14 (2H, H-1α), 2.60 (2H, ddd, J=14.00, 3.24, 3.24, H-1β), 1.61 (2H, H-2), 4.49 (1H, dd, J=12.3, 8.0, H-3α), 1.54 (1H, H-5), 4.92 (1H, d, J=12.03, H-6β), 0.83 (1H, H-9), 1.57 (2H, H-11), 1.21 (2H, H-12), 1.00 (2H, H-15α), 2.11 (2H, ddd, J=13.74, 13.6, 4.2, H-15β), 1.82 (2H, ddd, J=13.48, 12.70, 3.97, H-16α), 1.19 (2H, H-16β), 1.51 (1H, H-18), 1.98 (2H, dd, J=12.74, H-19α), 1.25 (2H, H-19β), 1.47 (2H, H-21a), 1.33 (2H, H-21b), 1.39 (2H, H-22a), 1.10 (2H, H-22b), 0.87 (3H, s, H-23), 0.90 (3H, s, H-24), 1.19 (3H, s, H-25), 1.37 (3H, s, H-26), 0.92 (3H, s, H-27), 1.23 (3H, s, H-28), 0.95 (3H, s, H-29), 0.89 (3H, s, H-30), 2.04 (3H, H-2′) 13 C-NMR (100 MHz, CDCl 3 -d1) δ: 39.9 (C-1), 23.8 (C-2), 80.5 (C-3), 39.3 (C-4), 56.7 (C-5), 72.2 (C-6), 211.2 (C-7), 43.3 (C-8), 55.3 (C-9), 38.2 (C-10), 17.5 (C-11), 33.9 (C-12), 82.3 (C-13), 45.0 (C-14), 22.5 (C-15), 29.7 (C-16), 33.5 (C-17), 49.1 (C-18), 38.5 (C-19), 31.3 (C-20), 34.0 (C-21), 39.0 (C-22), 28.1 (C-23), 16.4 (C-24), 16.0 (C-25), 20.5 (C-26), 18.4 (C-27), 31.3 (C-28), 31.8 (C-29), 25.0 (C-30), 171.0 (C-1′), 21.3 (C-2′).…”

Section: Resultsmentioning

confidence: 96%

“…Compound 3: C 35 H 52 O 6 1 H-NMR (600 MHz, MeOH-d4) δ: 3.17 (1H, dd, J=4.2, 11.4, H-3), 5.26 (1H, t, J=3.6, H-12), 3.79 (1H, d, J=10.2, H-15), 3.92 (1H, d, J=4.2, H-16), 2.54 (1H, dd, J=4.2, 14.4, H-18), 5.45 (1H, dd, J=6.0, 12.0, H-22), 0.98 (3H, s, H-23), 0.78 (3H, s, H-24), 0.95 (3H, s, H-25), 1.02 (3H, s, H-26), 1.40 (3H, s, H-27), 3.09, 3.22 (2H, d, J=10.8, H-28), 0.90 (3H, s, H-29), 1.04 (3H, s, H-30), 6.03 (1H, dq, J=1.2, 7.2, H-3′), 1.99 (3H, dd, J=1.8, 7.2, H-4′), 1.90 (3H, br t, J=1.8, H-5′) 13 C-NMR (150 MHz, MeOH-d4) δ: 39.8 (C-1), 27.9 (C-2), 79.7 (C-3), 38.2 (C-4), 56.6 (C-5), 19.7 (C-6), 37.2 (C-7), 41.9 (C-8), 48.2 (C-9), 33.6 (C-10), 24.7 (C-11), 123.4 (C-12), 144.5 (C-13), 45.7 (C-14), 68.5 (C-15), 75.4 (C-16), 41.9 (C-17), 42.9 (C-18), 47.6 (C-19), 33.6 (C-20) 42.3 (C-21), 73.3 (C-22), 28.7 (C-23), 16.2 (C-24), 15.9 (C-25), 17.8 (C-26), 20.9 (C-27), 63.8 (C-28), 32.4 (C-29), 25.1 (C-30), 169.5 (C-1′), 130.0 (C-2′), 138.1 (C-3′), 16.3 (C-4′), 21.1 (C-5′). Compound 4: the spectrum was reported previously ( 11 ). Compound 5: C 41 H 66 O 10 1 H-NMR (600 MHz, MeOH-d4) δ: 3.97 (2H, dd, J=5.410.8, H-1), 4.22 (2H, d, J=7.2, H-3) 13 C-NMR (150 MHz, MeOH-d4) δ: 68.7 (C-1), 70.2 (C-2), 64.0 (C-3), 105.4 (C-1′), 72.4 (C-2′), 74.9 (C-3′), 71.8 (C-4′), 76.8 (C-5′), 62.5 (C-6′), 175.0 (C-1″), 174.7 (C-1‴), 23.6–35.1 (C-2″-C-6″, C-9″, C-12″, C-15″, C-2‴-C-6‴, C-9‴, C-12‴, C-15‴), 129.1–133.8 (C-7″-C-8″, C-10″-C-11″, C-13″-C-14″, C-7‴-C-8‴, C-10‴-C-11‴, C-13‴-C-14‴), 14.5 (C-16″), 14.5 (C-16‴).…”

Section: Resultsmentioning

confidence: 98%

“…Compound 7: C 45 H 76 O 10 1 H-NMR (600 MHz, MeOH-d4) δ: 5.32 (1H, m, C=CH), 0.06 (3H, s, H-18″, H-18‴), 4.42 (1H, dd, J=3, 12, H-6′) 13 C-NMR (150 MHz, MeOH-d4) δ: 68.7 (C-1), 70.2 (C-2), 64.0 (C-3), 105.4 (C-1′), 72.4 (C-2′), 74.9 (C-3′), 71.8 (C-4′), 76.8 (C-5′), 62.5 (C-6′), 175.0 (C-1″), 174.7 (C-1‴), 128.2–132.7 (C-9″-C-10″, C-12″-C-13″, C-15‴-C-16‴, C-9‴-C-10‴, C-12‴-C-13‴), 21.5–35.1 (C-2″-C-8″, C-11″, C-14″-C-17″, C-2‴-C-8‴, C-11‴, C-16‴, C-17‴). Compound 8: the spectrum was reported previously ( 11 ). Compound 9: the spectrum was reported previously ( 11 ).…”

Section: Resultsmentioning

confidence: 98%

“…1 . Finally, 16 compounds, including flavonoids, C-27 steroidal saponins, monoterpenes, and triterpenes were identified as follows: compound 1: 3β-acetoxy-20-lupanol ( 11 ); compound 2: 3β,6α,13β-trihydroxyolean-7-one ( 12 ); compound 3: A1-barrigenol-22a-angelate ( 13 ); compound 4: (3R, 6R, 7E)-3-hydroxy-4,7-megastigmadien-9-one ( 11 ); compound 5: β-D-glucopyranoside, 3-[(1-oxo-9,12,15-octadecadienyl)oxy]-2-[(1-oxo-9,12,15-octadecatrienyl)oxy ( 14 ); compound 6: β-D-glucopyranoside, 2-[[(9Z,12Z,15Z)-1-oxo-9,12,15-octadecatrien-1-yl]oxy]-3-[(1-oxooctyl)oxy]propyl ( 15 ); compound 7: β-D-Glucopyranoside,3-[(1-oxo-9,12-octade-cadienyl)oxy]-2-[(1-oxo-9,12,15-octadecatrienyl)oxy]propyl ( 16 ); compound 8: kaempferol3-O-[2-O-(trans-p-coumaroyl)-3-O-α-D-glucopyranosyl]-α-D-glucopyranoside ( 11 ); compound 9: stigmasta-7,22-diene-3-O-[α-L-arabinopyranosyl(1→2)]-β-D-gala-ctopyranoside ( 11 ); compound 10: β-D-galactopy ranoside, (2S)-2-(acetyloxy)-3-[[(9Z)-1-oxo-9-octadecen-1-yl]oxy]propyl ( 17 ); compound 11: aromadendrin( 11 ); compound 12: α-spinasteryl-β-D-glucopyranoside ( 11 ); compound 13: catechin ( 11 ); compound 14: phlorizin4′-O-β-D-glucopyranoside ( 11 ); compound 15: 3β,6α,13β-trihydroxyolean-7-one ( 11 ); compound 16: dodecanoic acid ( 11 ).…”

Section: Resultsmentioning

confidence: 99%

See 4 more Smart Citations

The antitumor activity screening of chemical constituents from Camellia nitidissima Chi

Hou

Yang

et al. 2018

Int J Mol Med

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Chemotherapy is the preferred and most common treatment for cancer in clinical practice. An increasing number of researchers all over the world are focusing on natural medicines to find new antitumor drugs, and several reports have shown that Camellia nitidissima (C. nitidis-sima) Chi could reduce blood-lipid, decrease blood pressure, resist oxidation, prevent carcinogenesis and inhibit tumors. Therefore, the pharmacodynamics of the chemical constituents in C. nitidissima need to be investigated further. In the present study, 16 chemical constituents were isolated from the leaves of C. nitidissima, of which 6 compounds are reported to be found in this plant for the first time. Furthermore, all these phytochemicals were screened for antitumor activity on 4 common cancer cell lines, while compound 3, one oleanane-type triterpene, exhibited the most potential antitumor effects. Interestingly, to our knowledge, this was the first report that compound 3 inhibits cancer cells. Compound 3 inhibited EGFR-mutant lung cancer cell line, NCI-H1975 via apoptosis effect, with an IC50 of 13.37±2.05 µM at 48 h. Based on the data, compound 3 showed potential for antitumor drug development, suggesting the scientific basis for the antitumor activity of C. nitidissima.

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Section: Introductionmentioning

confidence: 69%

Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

See 3 more Smart Citations

The antitumor activity screening of chemical constituents from Camellia nitidissima Chi

Hou

Yang

et al. 2018

Int J Mol Med

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Genotypic and Phenotypic Diversity of Endemic Golden Camellias Collected from the North of Vietnam

Nga

Nguyen

et al. 2022

Chemistry & Biodiversity

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Golden Camellias have recently been used as a food, cosmetic, and traditional medicine in China and Vietnam. Forty-two species have natural distribution in Vietnam, of which thirty-two species were considered endemic species of this country. The morphology of leaves and flowers of these species were similar; therefore, their taxonomic identification usually needed experts and the authentication has often been confused among species. Our study aims to describe the genetic diversity and the relationship of six species Camellia phanii, Camellia tamdaoensis, Camellia tienii, Camellia flava, Camellia petelotii and Camellia euphlebia by using three chloroplast DNA-barcodes: matK, rbcL and trnH-psbA. We also clarified the significant differences in anatomical characteristics of midvein and blade of their leaves, which suggested the possibility to use these criteria in taxonomy. In addition, preliminary chemical profiles of the methanolic extracts of leaves from six Golden Camellias such as total phenolic content (TPC), total flavonoid content (TFC), total anthocyanin content (TAC) and chlorogenic acids content (TCGAs) also showed the diversity among them. Interestingly, the discrimination on the catechins profile among six species followed the same tendency with the genetic distance on the phylogeny tree suggesting that catechins (i. e., discriminative catechins) can be biomarkers for the chemotaxonomy of these six Golden Camellias.

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A Comprehensive Strategy for Metabolites Profiling of Flowers and Leaves from Camellia tienii, an Endemic Golden Tea of Vietnam

Nguyen,

Le,

Gontier

et al. 2024

Chemistry & Biodiversity

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Golden camellia is defined as a species of the Camellia genus with yellow flowers, which have long been used as a medicine, food, and cosmetic in many Asian countries. To date, more than 50 golden camellia species are considered endemic in Vietnam; however, more information is needed about its chemical constituents and biological activity. This work aims to unveil the potential of Camellia tienii Ninh, a golden camellia species, as an herbal beverage by examining the presence and abundance of chemical components in flowers and leaves. A comprehensive strategy has been developed using both liquid and gas chromatography coupled with mass spectrometry. Specifically, LC‐MS‐based widely targeted analyses were opted to characterize 158 polar metabolites belonging mainly to flavonoids, catechins, and amino acids classes, and an untargeted approach using GC‐MS annotated 42 major volatile compounds such as terpenes and fatty acids. The extensive profile revealed by these techniques could help understand the significant discrimination between two organs. C. tienii flowers accumulated more flavonoids, amino acids, and fatty acids, while leaves contain more terpenes, suggesting different pharmacological properties of these materials. Overall, this pipeline can be applied for other Camellia species and valorization of these valuable resources for health benefits purposes.

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Chemical Constituents from Leaves of Camellia nitidissima and Their Potential Cytotoxicity on SGC7901 Cells

Cited by 20 publications

References 7 publications

The antitumor activity screening of chemical constituents from Camellia nitidissima Chi

The antitumor activity screening of chemical constituents from Camellia nitidissima Chi

Genotypic and Phenotypic Diversity of Endemic Golden Camellias Collected from the North of Vietnam

A Comprehensive Strategy for Metabolites Profiling of Flowers and Leaves from Camellia tienii, an Endemic Golden Tea of Vietnam

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