Potential cancer chemopreventive constituents of the leaves of Macaranga triloba

Dae Sik Jang; Muriel Cuendet; Alison D. Pawlus; Leonardus B.S. Kardono; Kazuko Kawanishi; Norman R. Farnsworth; Harry H.S. Fong; John M. Pezzuto; A. Douglas Kinghorn

doi:10.1016/j.phytochem.2003.10.026

Potential cancer chemopreventive constituents of the leaves of Macaranga triloba

Dae Sik Jang, Muriel Cuendet, Alison D. Pawlus, Leonardus B.S. Kardono, Kazuko Kawanishi, Norman R. Farnsworth, Harry H.S. Fong, John M. Pezzuto, A. Douglas Kinghorn

Horticultural Science

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Abstract

Activity-guided fractionation of the leaves of Macaranga triloba, using an in vitro bioassay based on the inhibition of cyclooxygenase-2, resulted in the isolation of a rotenoid, 4,5-dihydro-5′α-hydroxy-4′α- methoxy-6a,12a-dehydro-α-toxicarol (1), as well as 12 known compounds, (+)-clovan-2β,9α-diol, ferulic acid, 3,7,3′,4′- tetramethylquercetin, 3,7,3′-trimethylquercetin, 3,7-dimethylquercetin, abscisic acid, 1β,6α-dihydroxy-4(15)-eudesmene, 3β-hydroxy-24- ethylcholest-5-en-7-one, loliolide, scopoletin, taraxerol, and 3-epi-taraxerol. The structure of compound 1 was determined using spectroscopic methods. All isolates were evaluated for their potential to inhibit cyclooxygenases-1 and -2 by measuring PGE₂ production, and to induce quinone reductase in cultured Hepa 1c1c7 mouse hepatoma cells.

Original language	English (US)
Pages (from-to)	345-350
Number of pages	6
Journal	Phytochemistry
Volume	65
Issue number	3
DOIs	https://doi.org/10.1016/j.phytochem.2003.10.026
State	Published - Feb 2004

Bibliographical note

Funding Information:
We thank Dr. K. Fagerquist, Mass Spectrometry Facility, Department of Chemistry, University of Minnesota, Minneapolis, MN, and Drs. J. A. (Art) Anderson and Y. Wang, Research Resources Center (RRC), University of Illinois at Chicago (UIC), for the mass spectral data. We are grateful to the RRC, UIC, for providing spectroscopic equipment, and to Dr. R. A. Kleps of the RRC, UIC, for facilitating the running of the 500 MHz NMR instrument. This research was supported by program project P01 CA48112, funded by the National Cancer Institute, NIH, Bethesda, MD.

Keywords

4,5-Dihydro-5′α- hydroxy-4′α-methoxy-6a,12a-dehydro-α-toxicarol
Cyclooxygenases-1 and -2
Euphorbiaceae
Flavonoids
Macaranga triloba
Quinone reductase

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Potential cancer chemopreventive constituents of the leaves of Macaranga triloba",

abstract = "Activity-guided fractionation of the leaves of Macaranga triloba, using an in vitro bioassay based on the inhibition of cyclooxygenase-2, resulted in the isolation of a rotenoid, 4,5-dihydro-5′α-hydroxy-4′α- methoxy-6a,12a-dehydro-α-toxicarol (1), as well as 12 known compounds, (+)-clovan-2β,9α-diol, ferulic acid, 3,7,3′,4′- tetramethylquercetin, 3,7,3′-trimethylquercetin, 3,7-dimethylquercetin, abscisic acid, 1β,6α-dihydroxy-4(15)-eudesmene, 3β-hydroxy-24- ethylcholest-5-en-7-one, loliolide, scopoletin, taraxerol, and 3-epi-taraxerol. The structure of compound 1 was determined using spectroscopic methods. All isolates were evaluated for their potential to inhibit cyclooxygenases-1 and -2 by measuring PGE2 production, and to induce quinone reductase in cultured Hepa 1c1c7 mouse hepatoma cells.",

keywords = "4,5-Dihydro-5′α- hydroxy-4′α-methoxy-6a,12a-dehydro-α-toxicarol, Cyclooxygenases-1 and -2, Euphorbiaceae, Flavonoids, Macaranga triloba, Quinone reductase",

author = "Jang, {Dae Sik} and Muriel Cuendet and Pawlus, {Alison D.} and Kardono, {Leonardus B.S.} and Kazuko Kawanishi and Farnsworth, {Norman R.} and Fong, {Harry H.S.} and Pezzuto, {John M.} and Kinghorn, {A. Douglas}",

note = "Funding Information: We thank Dr. K. Fagerquist, Mass Spectrometry Facility, Department of Chemistry, University of Minnesota, Minneapolis, MN, and Drs. J. A. (Art) Anderson and Y. Wang, Research Resources Center (RRC), University of Illinois at Chicago (UIC), for the mass spectral data. We are grateful to the RRC, UIC, for providing spectroscopic equipment, and to Dr. R. A. Kleps of the RRC, UIC, for facilitating the running of the 500 MHz NMR instrument. This research was supported by program project P01 CA48112, funded by the National Cancer Institute, NIH, Bethesda, MD.",

year = "2004",

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doi = "10.1016/j.phytochem.2003.10.026",

language = "English (US)",

volume = "65",

pages = "345--350",

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AU - Jang, Dae Sik

AU - Cuendet, Muriel

AU - Pawlus, Alison D.

AU - Kardono, Leonardus B.S.

AU - Kawanishi, Kazuko

AU - Farnsworth, Norman R.

AU - Fong, Harry H.S.

AU - Pezzuto, John M.

AU - Kinghorn, A. Douglas

N1 - Funding Information: We thank Dr. K. Fagerquist, Mass Spectrometry Facility, Department of Chemistry, University of Minnesota, Minneapolis, MN, and Drs. J. A. (Art) Anderson and Y. Wang, Research Resources Center (RRC), University of Illinois at Chicago (UIC), for the mass spectral data. We are grateful to the RRC, UIC, for providing spectroscopic equipment, and to Dr. R. A. Kleps of the RRC, UIC, for facilitating the running of the 500 MHz NMR instrument. This research was supported by program project P01 CA48112, funded by the National Cancer Institute, NIH, Bethesda, MD.

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N2 - Activity-guided fractionation of the leaves of Macaranga triloba, using an in vitro bioassay based on the inhibition of cyclooxygenase-2, resulted in the isolation of a rotenoid, 4,5-dihydro-5′α-hydroxy-4′α- methoxy-6a,12a-dehydro-α-toxicarol (1), as well as 12 known compounds, (+)-clovan-2β,9α-diol, ferulic acid, 3,7,3′,4′- tetramethylquercetin, 3,7,3′-trimethylquercetin, 3,7-dimethylquercetin, abscisic acid, 1β,6α-dihydroxy-4(15)-eudesmene, 3β-hydroxy-24- ethylcholest-5-en-7-one, loliolide, scopoletin, taraxerol, and 3-epi-taraxerol. The structure of compound 1 was determined using spectroscopic methods. All isolates were evaluated for their potential to inhibit cyclooxygenases-1 and -2 by measuring PGE2 production, and to induce quinone reductase in cultured Hepa 1c1c7 mouse hepatoma cells.

AB - Activity-guided fractionation of the leaves of Macaranga triloba, using an in vitro bioassay based on the inhibition of cyclooxygenase-2, resulted in the isolation of a rotenoid, 4,5-dihydro-5′α-hydroxy-4′α- methoxy-6a,12a-dehydro-α-toxicarol (1), as well as 12 known compounds, (+)-clovan-2β,9α-diol, ferulic acid, 3,7,3′,4′- tetramethylquercetin, 3,7,3′-trimethylquercetin, 3,7-dimethylquercetin, abscisic acid, 1β,6α-dihydroxy-4(15)-eudesmene, 3β-hydroxy-24- ethylcholest-5-en-7-one, loliolide, scopoletin, taraxerol, and 3-epi-taraxerol. The structure of compound 1 was determined using spectroscopic methods. All isolates were evaluated for their potential to inhibit cyclooxygenases-1 and -2 by measuring PGE2 production, and to induce quinone reductase in cultured Hepa 1c1c7 mouse hepatoma cells.

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KW - Cyclooxygenases-1 and -2

KW - Euphorbiaceae

KW - Flavonoids

KW - Macaranga triloba

KW - Quinone reductase

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JO - Phytochemistry

JF - Phytochemistry

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ER -

Potential cancer chemopreventive constituents of the leaves of Macaranga triloba

Abstract

Bibliographical note

Keywords

UN SDGs

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