Cytotoxic prenylated flavanones from Monotes engleri

E. K. Seo; G. L. Silva; H. B. Chai; T. E. Chagwedera; N. R. Farnsworth; G. A. Cordell; J. M. Pezzuto; A. D. Kinghorn

doi:10.1016/S0031-9422(96)00871-0

Cytotoxic prenylated flavanones from Monotes engleri

E. K. Seo
, G. L. Silva
, H. B. Chai
, T. E. Chagwedera
, N. R. Farnsworth
, G. A. Cordell
, J. M. Pezzuto
, A. D. Kinghorn

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

65 Scopus citations

Abstract

From the leaves of Monotes engleri, five prenylated flavanones were isolated as constituents that displayed cytotoxic activity against several human cancer cell lines. Three of these substances are novel, namely, 6- (1,1-dimethylallyl)naringenin, 6-(1,1-dimethylallyl)eriodictyol and 3'-O- methyl-6-(1,1-dimethylallyl)-eriodictyol, with the other two active substances being the known flavanones, 6,8-diprenyleriodictyol and hiravanone. Additionally, two novel, but non-cytotoxic, biogenetically related flavanones were isolated, 6[(2RS)-hydroxy-3-methyl-3-butenyl]-8- prenyleriodictyol and 5,4'-dihydroxy-4''4''-dimethyl-5''-methyl-5''H- dihydrofurano[2''3'':6,7]flavanone. The structures of the new compounds were determined by spectral analysis 1D- and 2D-NMR experiments.

Original language	English
Pages (from-to)	509-515
Number of pages	7
Journal	Phytochemistry
Volume	45
Issue number	3
DOIs	https://doi.org/10.1016/S0031-9422(96)00871-0
State	Published - Jun 1997

Bibliographical note

Funding Information:
Acknowledgements-This investigation was supported by grant UOl-CA-52956 from the National Cancer Institute, NIH, Bethesda, Maryland. We wish to thank the Nuclear Magnetic Resonance Laboratory of the Research Resources Center, University of Illinois at Chicago, for provision of the spectroscopic equipment used in this study. Mr R. B. Dvorak and Dr K. Zaw of the Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, are acknowledged for the MS data and for valuable input concerning the NMR studies, respectively. We also acknowledge Drs D. S. H. L. Kim and I.-S. Lee for helpful suggestions.

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

cytotoxic activity
Dipterocarpaceae
human cancer cell lines
leaves
Monotes engleri
prenylated flavanones

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10.1016/S0031-9422(96)00871-0

Cite this

@article{f5e083d7e20341eb96a0ecb5035d3417,

title = "Cytotoxic prenylated flavanones from Monotes engleri",

abstract = "From the leaves of Monotes engleri, five prenylated flavanones were isolated as constituents that displayed cytotoxic activity against several human cancer cell lines. Three of these substances are novel, namely, 6- (1,1-dimethylallyl)naringenin, 6-(1,1-dimethylallyl)eriodictyol and 3'-O- methyl-6-(1,1-dimethylallyl)-eriodictyol, with the other two active substances being the known flavanones, 6,8-diprenyleriodictyol and hiravanone. Additionally, two novel, but non-cytotoxic, biogenetically related flavanones were isolated, 6[(2RS)-hydroxy-3-methyl-3-butenyl]-8- prenyleriodictyol and 5,4'-dihydroxy-4''4''-dimethyl-5''-methyl-5''H- dihydrofurano[2''3'':6,7]flavanone. The structures of the new compounds were determined by spectral analysis 1D- and 2D-NMR experiments.",

keywords = "cytotoxic activity, Dipterocarpaceae, human cancer cell lines, leaves, Monotes engleri, prenylated flavanones",

author = "Seo, \{E. K.\} and Silva, \{G. L.\} and Chai, \{H. B.\} and Chagwedera, \{T. E.\} and Farnsworth, \{N. R.\} and Cordell, \{G. A.\} and Pezzuto, \{J. M.\} and Kinghorn, \{A. D.\}",

note = "Funding Information: Acknowledgements-This investigation was supported by grant UOl-CA-52956 from the National Cancer Institute, NIH, Bethesda, Maryland. We wish to thank the Nuclear Magnetic Resonance Laboratory of the Research Resources Center, University of Illinois at Chicago, for provision of the spectroscopic equipment used in this study. Mr R. B. Dvorak and Dr K. Zaw of the Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, are acknowledged for the MS data and for valuable input concerning the NMR studies, respectively. We also acknowledge Drs D. S. H. L. Kim and I.-S. Lee for helpful suggestions.",

year = "1997",

month = jun,

doi = "10.1016/S0031-9422(96)00871-0",

language = "English",

volume = "45",

pages = "509--515",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Ltd.",

number = "3",

}

TY - JOUR

T1 - Cytotoxic prenylated flavanones from Monotes engleri

AU - Seo, E. K.

AU - Silva, G. L.

AU - Chai, H. B.

AU - Chagwedera, T. E.

AU - Farnsworth, N. R.

AU - Cordell, G. A.

AU - Pezzuto, J. M.

AU - Kinghorn, A. D.

N1 - Funding Information: Acknowledgements-This investigation was supported by grant UOl-CA-52956 from the National Cancer Institute, NIH, Bethesda, Maryland. We wish to thank the Nuclear Magnetic Resonance Laboratory of the Research Resources Center, University of Illinois at Chicago, for provision of the spectroscopic equipment used in this study. Mr R. B. Dvorak and Dr K. Zaw of the Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, are acknowledged for the MS data and for valuable input concerning the NMR studies, respectively. We also acknowledge Drs D. S. H. L. Kim and I.-S. Lee for helpful suggestions.

PY - 1997/6

Y1 - 1997/6

N2 - From the leaves of Monotes engleri, five prenylated flavanones were isolated as constituents that displayed cytotoxic activity against several human cancer cell lines. Three of these substances are novel, namely, 6- (1,1-dimethylallyl)naringenin, 6-(1,1-dimethylallyl)eriodictyol and 3'-O- methyl-6-(1,1-dimethylallyl)-eriodictyol, with the other two active substances being the known flavanones, 6,8-diprenyleriodictyol and hiravanone. Additionally, two novel, but non-cytotoxic, biogenetically related flavanones were isolated, 6[(2RS)-hydroxy-3-methyl-3-butenyl]-8- prenyleriodictyol and 5,4'-dihydroxy-4''4''-dimethyl-5''-methyl-5''H- dihydrofurano[2''3'':6,7]flavanone. The structures of the new compounds were determined by spectral analysis 1D- and 2D-NMR experiments.

AB - From the leaves of Monotes engleri, five prenylated flavanones were isolated as constituents that displayed cytotoxic activity against several human cancer cell lines. Three of these substances are novel, namely, 6- (1,1-dimethylallyl)naringenin, 6-(1,1-dimethylallyl)eriodictyol and 3'-O- methyl-6-(1,1-dimethylallyl)-eriodictyol, with the other two active substances being the known flavanones, 6,8-diprenyleriodictyol and hiravanone. Additionally, two novel, but non-cytotoxic, biogenetically related flavanones were isolated, 6[(2RS)-hydroxy-3-methyl-3-butenyl]-8- prenyleriodictyol and 5,4'-dihydroxy-4''4''-dimethyl-5''-methyl-5''H- dihydrofurano[2''3'':6,7]flavanone. The structures of the new compounds were determined by spectral analysis 1D- and 2D-NMR experiments.

KW - cytotoxic activity

KW - Dipterocarpaceae

KW - human cancer cell lines

KW - leaves

KW - Monotes engleri

KW - prenylated flavanones

UR - https://www.scopus.com/pages/publications/0031172185

U2 - 10.1016/S0031-9422(96)00871-0

DO - 10.1016/S0031-9422(96)00871-0

M3 - Article

C2 - 9190085

AN - SCOPUS:0031172185

SN - 0031-9422

VL - 45

SP - 509

EP - 515

JO - Phytochemistry

JF - Phytochemistry

IS - 3

ER -

Cytotoxic prenylated flavanones from Monotes engleri

Abstract

Bibliographical note

UN SDGs

Keywords

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