Beccaridiol, an unusual 28-nortriterpenoid from the leaves of Diplectria beccariana

Dae Sik Jang; Bao Ning Su; Alison D. Pawlus; Young Hwa Kang; Leonardus B.S. Kardono; Soedarsono Riswan; Johar J. Afriastini; Harry H.S. Fong; John M. Pezzuto; A. Douglas Kinghorn

doi:10.1016/j.phytochem.2005.11.026

Beccaridiol, an unusual 28-nortriterpenoid from the leaves of Diplectria beccariana

Dae Sik Jang, Bao Ning Su, Alison D. Pawlus, Young Hwa Kang, Leonardus B.S. Kardono, Soedarsono Riswan, Johar J. Afriastini, Harry H.S. Fong, John M. Pezzuto, A. Douglas Kinghorn

Horticultural Science

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

16 Scopus citations

Abstract

A C₂₉-triterpene, beccaridiol (1), a dihydrochalcone natural product, 2′,4′-dihydroxy-3-(4-methoxyphenyl)-propiophenone (2), as well as three known compounds, 4′-hydroxy-1′,2′-dihydro-β-ionone, 4′-O-methyldavidigenin (3), and ursolic acid, have been isolated from an EtOAc-soluble extract of the leaves of Diplectria beccariana. Beccaridiol (1) was characterized as an ursane-type 28-nortriterpene possessing an unusual aromatic E-ring by spectroscopic data interpretation. The relative configuration of this unusual isolate was established by analyzing the observed NOESY NMR correlations, and the absolute stereochemistry of 1 was then determined based on the circular dichroism (CD) spectrum of its 2,3-di-p-bromobenzoate (1b) derivative. All isolates were evaluated for their potential cancer chemopreventive properties utilizing a cell culture assay to determine quinone reductase induction.

Original language	English (US)
Pages (from-to)	1832-1837
Number of pages	6
Journal	Phytochemistry
Volume	67
Issue number	16
DOIs	https://doi.org/10.1016/j.phytochem.2005.11.026
State	Published - Aug 2006

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

Beccaridiol
Circular dichroism
Dihydrochalcone
Diplectria beccariana
Melastomataceae
Nortriterpenoid
Quinone reductase

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@article{fba3d442807d470ea97c005fc3d838f4,

title = "Beccaridiol, an unusual 28-nortriterpenoid from the leaves of Diplectria beccariana",

abstract = "A C29-triterpene, beccaridiol (1), a dihydrochalcone natural product, 2′,4′-dihydroxy-3-(4-methoxyphenyl)-propiophenone (2), as well as three known compounds, 4′-hydroxy-1′,2′-dihydro-β-ionone, 4′-O-methyldavidigenin (3), and ursolic acid, have been isolated from an EtOAc-soluble extract of the leaves of Diplectria beccariana. Beccaridiol (1) was characterized as an ursane-type 28-nortriterpene possessing an unusual aromatic E-ring by spectroscopic data interpretation. The relative configuration of this unusual isolate was established by analyzing the observed NOESY NMR correlations, and the absolute stereochemistry of 1 was then determined based on the circular dichroism (CD) spectrum of its 2,3-di-p-bromobenzoate (1b) derivative. All isolates were evaluated for their potential cancer chemopreventive properties utilizing a cell culture assay to determine quinone reductase induction.",

keywords = "Beccaridiol, Circular dichroism, Dihydrochalcone, Diplectria beccariana, Melastomataceae, Nortriterpenoid, Quinone reductase",

author = "Jang, {Dae Sik} and Su, {Bao Ning} and Pawlus, {Alison D.} and Kang, {Young Hwa} and Kardono, {Leonardus B.S.} and Soedarsono Riswan and Afriastini, {Johar J.} 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 = "2006",

month = aug,

doi = "10.1016/j.phytochem.2005.11.026",

language = "English (US)",

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T1 - Beccaridiol, an unusual 28-nortriterpenoid from the leaves of Diplectria beccariana

AU - Jang, Dae Sik

AU - Su, Bao Ning

AU - Pawlus, Alison D.

AU - Kang, Young Hwa

AU - Kardono, Leonardus B.S.

AU - Riswan, Soedarsono

AU - Afriastini, Johar J.

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.

PY - 2006/8

Y1 - 2006/8

N2 - A C29-triterpene, beccaridiol (1), a dihydrochalcone natural product, 2′,4′-dihydroxy-3-(4-methoxyphenyl)-propiophenone (2), as well as three known compounds, 4′-hydroxy-1′,2′-dihydro-β-ionone, 4′-O-methyldavidigenin (3), and ursolic acid, have been isolated from an EtOAc-soluble extract of the leaves of Diplectria beccariana. Beccaridiol (1) was characterized as an ursane-type 28-nortriterpene possessing an unusual aromatic E-ring by spectroscopic data interpretation. The relative configuration of this unusual isolate was established by analyzing the observed NOESY NMR correlations, and the absolute stereochemistry of 1 was then determined based on the circular dichroism (CD) spectrum of its 2,3-di-p-bromobenzoate (1b) derivative. All isolates were evaluated for their potential cancer chemopreventive properties utilizing a cell culture assay to determine quinone reductase induction.

AB - A C29-triterpene, beccaridiol (1), a dihydrochalcone natural product, 2′,4′-dihydroxy-3-(4-methoxyphenyl)-propiophenone (2), as well as three known compounds, 4′-hydroxy-1′,2′-dihydro-β-ionone, 4′-O-methyldavidigenin (3), and ursolic acid, have been isolated from an EtOAc-soluble extract of the leaves of Diplectria beccariana. Beccaridiol (1) was characterized as an ursane-type 28-nortriterpene possessing an unusual aromatic E-ring by spectroscopic data interpretation. The relative configuration of this unusual isolate was established by analyzing the observed NOESY NMR correlations, and the absolute stereochemistry of 1 was then determined based on the circular dichroism (CD) spectrum of its 2,3-di-p-bromobenzoate (1b) derivative. All isolates were evaluated for their potential cancer chemopreventive properties utilizing a cell culture assay to determine quinone reductase induction.

KW - Beccaridiol

KW - Circular dichroism

KW - Dihydrochalcone

KW - Diplectria beccariana

KW - Melastomataceae

KW - Nortriterpenoid

KW - Quinone reductase

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SN - 0031-9422

VL - 67

SP - 1832

EP - 1837

JO - Phytochemistry

JF - Phytochemistry

IS - 16

ER -

Beccaridiol, an unusual 28-nortriterpenoid from the leaves of Diplectria beccariana

Abstract

Bibliographical note

Keywords

UN SDGs

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