Cytotoxic Coumarins from the Bark of Mammea siamensis

Ngoc Trang Nhu Ngo, Vy Thuy Nguyen, Hoa Van Vo, Ole Vang, Fritz Duus, Thuy-Duong Huynh Ho, Hung Dinh Pham, Lien-Hoa Dieu Nguyen

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

A new geranylated coumarin, (E)-4-(1-hydroxypropyl)-5,7-dihydroxy-6-(3,7-dimethyl-2,6-octadienyl)-8-(3-methyl-1-oxobutyl)coumarin (named surangin D), was isolated from the bark of Mammea siamensis collected in Vietnam, along with four known coumarins, surangins B and C, and theraphins B and C, and seven xanthones, 1,7-dihydroxyxanthone, 7-hydroxy-1-methoxyxanthone, 1,7-dimethoxyxanthone, 1,7-dimethoxy-6-hydroxyxanthone, 1,6,7-trihydroxyxanthone, 1,3,7-trihydroxyxanthone, and 1,7-dihydroxy-3-methoxyxanthone. Their structures were determined by spectroscopic methods (mainly 1D- and 2D-NMR) and preparation of methylated derivatives. The four coumarins, surangins C and D and theraphins B and C, were tested for inhibition of cell proliferation in DLD-1 (colon cancer), MCF-7 (breast adenocarcinoma), HeLa (human cervical cancer) and NCI-H460 (human lung cancer) cell lines using the sulforhodamine B (SRB) assay. In all four cell lines, theraphin C showed the strongest activity (IC₅₀ in the range of 1.6-5.7 µM). Testing the anti-proliferative effect of the methylated derivatives showed reduced cellular effects of all derivatives, indicating that the number and position of free hydroxyl groups were very important for the anti-proliferative effect.
OriginalsprogEngelsk
TidsskriftChemical & Pharmaceutical Bulletin
Vol/bind58
Udgave nummer11
Sider (fra-til)1487-1491
ISSN0009-2363
StatusUdgivet - 2010

Citer dette

Ngo, N. T. N., Nguyen, V. T., Vo, H. V., Vang, O., Duus, F., Ho, T-D. H., ... Nguyen, L-H. D. (2010). Cytotoxic Coumarins from the Bark of Mammea siamensis. Chemical & Pharmaceutical Bulletin, 58(11), 1487-1491.
Ngo, Ngoc Trang Nhu ; Nguyen, Vy Thuy ; Vo, Hoa Van ; Vang, Ole ; Duus, Fritz ; Ho, Thuy-Duong Huynh ; Pham, Hung Dinh ; Nguyen, Lien-Hoa Dieu. / Cytotoxic Coumarins from the Bark of Mammea siamensis. I: Chemical & Pharmaceutical Bulletin. 2010 ; Bind 58, Nr. 11. s. 1487-1491.
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title = "Cytotoxic Coumarins from the Bark of Mammea siamensis",
abstract = "A new geranylated coumarin, (E)-4-(1-hydroxypropyl)-5,7-dihydroxy-6-(3,7-dimethyl-2,6-octadienyl)-8-(3-methyl-1-oxobutyl)coumarin (named surangin D), was isolated from the bark of Mammea siamensis collected in Vietnam, along with four known coumarins, surangins B and C, and theraphins B and C, and seven xanthones, 1,7-dihydroxyxanthone, 7-hydroxy-1-methoxyxanthone, 1,7-dimethoxyxanthone, 1,7-dimethoxy-6-hydroxyxanthone, 1,6,7-trihydroxyxanthone, 1,3,7-trihydroxyxanthone, and 1,7-dihydroxy-3-methoxyxanthone. Their structures were determined by spectroscopic methods (mainly 1D- and 2D-NMR) and preparation of methylated derivatives. The four coumarins, surangins C and D and theraphins B and C, were tested for inhibition of cell proliferation in DLD-1 (colon cancer), MCF-7 (breast adenocarcinoma), HeLa (human cervical cancer) and NCI-H460 (human lung cancer) cell lines using the sulforhodamine B (SRB) assay. In all four cell lines, theraphin C showed the strongest activity (IC₅₀ in the range of 1.6-5.7 µM). Testing the anti-proliferative effect of the methylated derivatives showed reduced cellular effects of all derivatives, indicating that the number and position of free hydroxyl groups were very important for the anti-proliferative effect.",
author = "Ngo, {Ngoc Trang Nhu} and Nguyen, {Vy Thuy} and Vo, {Hoa Van} and Ole Vang and Fritz Duus and Ho, {Thuy-Duong Huynh} and Pham, {Hung Dinh} and Nguyen, {Lien-Hoa Dieu}",
year = "2010",
language = "English",
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pages = "1487--1491",
journal = "Chemical & Pharmaceutical Bulletin",
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Ngo, NTN, Nguyen, VT, Vo, HV, Vang, O, Duus, F, Ho, T-DH, Pham, HD & Nguyen, L-HD 2010, 'Cytotoxic Coumarins from the Bark of Mammea siamensis', Chemical & Pharmaceutical Bulletin, bind 58, nr. 11, s. 1487-1491.

Cytotoxic Coumarins from the Bark of Mammea siamensis. / Ngo, Ngoc Trang Nhu ; Nguyen, Vy Thuy; Vo, Hoa Van; Vang, Ole; Duus, Fritz; Ho, Thuy-Duong Huynh; Pham, Hung Dinh; Nguyen, Lien-Hoa Dieu.

I: Chemical & Pharmaceutical Bulletin, Bind 58, Nr. 11, 2010, s. 1487-1491.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Cytotoxic Coumarins from the Bark of Mammea siamensis

AU - Ngo, Ngoc Trang Nhu

AU - Nguyen, Vy Thuy

AU - Vo, Hoa Van

AU - Vang, Ole

AU - Duus, Fritz

AU - Ho, Thuy-Duong Huynh

AU - Pham, Hung Dinh

AU - Nguyen, Lien-Hoa Dieu

PY - 2010

Y1 - 2010

N2 - A new geranylated coumarin, (E)-4-(1-hydroxypropyl)-5,7-dihydroxy-6-(3,7-dimethyl-2,6-octadienyl)-8-(3-methyl-1-oxobutyl)coumarin (named surangin D), was isolated from the bark of Mammea siamensis collected in Vietnam, along with four known coumarins, surangins B and C, and theraphins B and C, and seven xanthones, 1,7-dihydroxyxanthone, 7-hydroxy-1-methoxyxanthone, 1,7-dimethoxyxanthone, 1,7-dimethoxy-6-hydroxyxanthone, 1,6,7-trihydroxyxanthone, 1,3,7-trihydroxyxanthone, and 1,7-dihydroxy-3-methoxyxanthone. Their structures were determined by spectroscopic methods (mainly 1D- and 2D-NMR) and preparation of methylated derivatives. The four coumarins, surangins C and D and theraphins B and C, were tested for inhibition of cell proliferation in DLD-1 (colon cancer), MCF-7 (breast adenocarcinoma), HeLa (human cervical cancer) and NCI-H460 (human lung cancer) cell lines using the sulforhodamine B (SRB) assay. In all four cell lines, theraphin C showed the strongest activity (IC₅₀ in the range of 1.6-5.7 µM). Testing the anti-proliferative effect of the methylated derivatives showed reduced cellular effects of all derivatives, indicating that the number and position of free hydroxyl groups were very important for the anti-proliferative effect.

AB - A new geranylated coumarin, (E)-4-(1-hydroxypropyl)-5,7-dihydroxy-6-(3,7-dimethyl-2,6-octadienyl)-8-(3-methyl-1-oxobutyl)coumarin (named surangin D), was isolated from the bark of Mammea siamensis collected in Vietnam, along with four known coumarins, surangins B and C, and theraphins B and C, and seven xanthones, 1,7-dihydroxyxanthone, 7-hydroxy-1-methoxyxanthone, 1,7-dimethoxyxanthone, 1,7-dimethoxy-6-hydroxyxanthone, 1,6,7-trihydroxyxanthone, 1,3,7-trihydroxyxanthone, and 1,7-dihydroxy-3-methoxyxanthone. Their structures were determined by spectroscopic methods (mainly 1D- and 2D-NMR) and preparation of methylated derivatives. The four coumarins, surangins C and D and theraphins B and C, were tested for inhibition of cell proliferation in DLD-1 (colon cancer), MCF-7 (breast adenocarcinoma), HeLa (human cervical cancer) and NCI-H460 (human lung cancer) cell lines using the sulforhodamine B (SRB) assay. In all four cell lines, theraphin C showed the strongest activity (IC₅₀ in the range of 1.6-5.7 µM). Testing the anti-proliferative effect of the methylated derivatives showed reduced cellular effects of all derivatives, indicating that the number and position of free hydroxyl groups were very important for the anti-proliferative effect.

M3 - Journal article

VL - 58

SP - 1487

EP - 1491

JO - Chemical & Pharmaceutical Bulletin

JF - Chemical & Pharmaceutical Bulletin

SN - 0009-2363

IS - 11

ER -