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Isolation, Characterization, Crystal Structure Elucidation, and Anticancer Study of Dimethyl Cardamonin, Isolated from Syzygium campanulatum Korth.

Memon AH, Ismail Z, Aisha AF, Al-Suede FS, Hamil MS, Hashim S, Saeed MA, Laghari M, Abdul Majid AM - Evid Based Complement Alternat Med (2014)

Bottom Line: Conventionally it has been used as a stomachic.The structural characterization of DMC was carried out by making use of various techniques including UV, IR, NMR spectral followed by LC-MS, and X-ray crystallographic techniques.For determining the purity of compound, highly effective techniques including TLC, HPLC, and melting point were used.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia.

ABSTRACT
Syzygium campanulatum Korth is an equatorial, evergreen, aboriginal shrub of Malaysia. Conventionally it has been used as a stomachic. However, in the currently conducted study dimethyl cardamonin or 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (DMC) was isolated from S. campanulatum Korth, leaf extract. The structural characterization of DMC was carried out by making use of various techniques including UV, IR, NMR spectral followed by LC-MS, and X-ray crystallographic techniques. For determining the purity of compound, highly effective techniques including TLC, HPLC, and melting point were used. The cytotoxicity of DMC and three different extracts of S. campanulatum was evaluated against human colon cancer cell line (HT-29) by three different assays. DMC and ethanolic extract revealed potent and dose-dependent cytotoxic activity on the cancer cell line with IC50 12.6 and 90.1 µg/mL, respectively. Quite astonishingly to our knowledge, this is the very first report on S. campanulatum as being a rich source (3.5%) of DMC, X-ray crystallography, and anticancer activity on human colon cancer cells.

No MeSH data available.


Related in: MedlinePlus

(a) The inhibitory effects of DMC and ethanolic extract of S. campanulatum on the migration property of HT-29 cells, which is a characteristic of metastasis of the cancer cells. (b) Clonogenic cell survival (%) of HT-29 treated with 1% DMSO as a negative control, 3 μg/mL of 5-fluorouracil as positive control, and indicated concentrations of S. campanulatum ethanolic extract and DMC. (c) The percentage of surviving fraction obtained after the treatment with DMC and ethanolic extract of S. campanulatum. The percentage of surviving fraction of the HT-29 colonies was decreased with increasing concentration of DMC and ethanolic extract S. campanulatum, mean ± SD (n = either 6 or 10).
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fig5: (a) The inhibitory effects of DMC and ethanolic extract of S. campanulatum on the migration property of HT-29 cells, which is a characteristic of metastasis of the cancer cells. (b) Clonogenic cell survival (%) of HT-29 treated with 1% DMSO as a negative control, 3 μg/mL of 5-fluorouracil as positive control, and indicated concentrations of S. campanulatum ethanolic extract and DMC. (c) The percentage of surviving fraction obtained after the treatment with DMC and ethanolic extract of S. campanulatum. The percentage of surviving fraction of the HT-29 colonies was decreased with increasing concentration of DMC and ethanolic extract S. campanulatum, mean ± SD (n = either 6 or 10).

Mentions: Wound healing assay was used to examine the effects of DMC and ethanolic extract of S. campanulatum on the migration of HT-29 cells. For improved results, this was executed on the experimental lines: the percentage of inhibition of wound closure in the presence and absence of DMC was calculated after every 12 and 48 h, relative to the zero time. The results of the percentage of inhibition of wound healing assay are as depicted in Figure 4. The results sharply outlined the fact that the percentage of wound closure after 48 h was almost 100% in the untreated cells, whereas, in treated group, the wound remained open even after 48 h period time. The percentage of inhibition of migration of HT-29 cancer cells is shown in Figure 5(a). DMC (3 μg/mL), at every 12 and 48 h, inhibited the migration of HT-29 cells up to 60 and 75%, while 6 μg/mL concentration of DMC inhibited cell migration at 80 and 90% at the same duration of 12 and 48 h, respectively. The ethanolic extract of S. campanulatum after 12 and 48 h at 30 and 60 μg/mL inhibited the HT-29 migration 30–60 and 50–90%, respectively. The positive control 5-fluorouracil (3 μg/mL) showed 40 and 80% inhibition in migration of HT-29 cells after 12 and 48 h, respectively.


Isolation, Characterization, Crystal Structure Elucidation, and Anticancer Study of Dimethyl Cardamonin, Isolated from Syzygium campanulatum Korth.

Memon AH, Ismail Z, Aisha AF, Al-Suede FS, Hamil MS, Hashim S, Saeed MA, Laghari M, Abdul Majid AM - Evid Based Complement Alternat Med (2014)

(a) The inhibitory effects of DMC and ethanolic extract of S. campanulatum on the migration property of HT-29 cells, which is a characteristic of metastasis of the cancer cells. (b) Clonogenic cell survival (%) of HT-29 treated with 1% DMSO as a negative control, 3 μg/mL of 5-fluorouracil as positive control, and indicated concentrations of S. campanulatum ethanolic extract and DMC. (c) The percentage of surviving fraction obtained after the treatment with DMC and ethanolic extract of S. campanulatum. The percentage of surviving fraction of the HT-29 colonies was decreased with increasing concentration of DMC and ethanolic extract S. campanulatum, mean ± SD (n = either 6 or 10).
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4228816&req=5

fig5: (a) The inhibitory effects of DMC and ethanolic extract of S. campanulatum on the migration property of HT-29 cells, which is a characteristic of metastasis of the cancer cells. (b) Clonogenic cell survival (%) of HT-29 treated with 1% DMSO as a negative control, 3 μg/mL of 5-fluorouracil as positive control, and indicated concentrations of S. campanulatum ethanolic extract and DMC. (c) The percentage of surviving fraction obtained after the treatment with DMC and ethanolic extract of S. campanulatum. The percentage of surviving fraction of the HT-29 colonies was decreased with increasing concentration of DMC and ethanolic extract S. campanulatum, mean ± SD (n = either 6 or 10).
Mentions: Wound healing assay was used to examine the effects of DMC and ethanolic extract of S. campanulatum on the migration of HT-29 cells. For improved results, this was executed on the experimental lines: the percentage of inhibition of wound closure in the presence and absence of DMC was calculated after every 12 and 48 h, relative to the zero time. The results of the percentage of inhibition of wound healing assay are as depicted in Figure 4. The results sharply outlined the fact that the percentage of wound closure after 48 h was almost 100% in the untreated cells, whereas, in treated group, the wound remained open even after 48 h period time. The percentage of inhibition of migration of HT-29 cancer cells is shown in Figure 5(a). DMC (3 μg/mL), at every 12 and 48 h, inhibited the migration of HT-29 cells up to 60 and 75%, while 6 μg/mL concentration of DMC inhibited cell migration at 80 and 90% at the same duration of 12 and 48 h, respectively. The ethanolic extract of S. campanulatum after 12 and 48 h at 30 and 60 μg/mL inhibited the HT-29 migration 30–60 and 50–90%, respectively. The positive control 5-fluorouracil (3 μg/mL) showed 40 and 80% inhibition in migration of HT-29 cells after 12 and 48 h, respectively.

Bottom Line: Conventionally it has been used as a stomachic.The structural characterization of DMC was carried out by making use of various techniques including UV, IR, NMR spectral followed by LC-MS, and X-ray crystallographic techniques.For determining the purity of compound, highly effective techniques including TLC, HPLC, and melting point were used.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia.

ABSTRACT
Syzygium campanulatum Korth is an equatorial, evergreen, aboriginal shrub of Malaysia. Conventionally it has been used as a stomachic. However, in the currently conducted study dimethyl cardamonin or 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (DMC) was isolated from S. campanulatum Korth, leaf extract. The structural characterization of DMC was carried out by making use of various techniques including UV, IR, NMR spectral followed by LC-MS, and X-ray crystallographic techniques. For determining the purity of compound, highly effective techniques including TLC, HPLC, and melting point were used. The cytotoxicity of DMC and three different extracts of S. campanulatum was evaluated against human colon cancer cell line (HT-29) by three different assays. DMC and ethanolic extract revealed potent and dose-dependent cytotoxic activity on the cancer cell line with IC50 12.6 and 90.1 µg/mL, respectively. Quite astonishingly to our knowledge, this is the very first report on S. campanulatum as being a rich source (3.5%) of DMC, X-ray crystallography, and anticancer activity on human colon cancer cells.

No MeSH data available.


Related in: MedlinePlus