1969

DOI: 10.1016/s0040-4020(01)82733-2

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Tumor inhibitors—XXXIII

S. Morris Kupchan¹,

Carl W. Sigel²,

R.J. Hemingway³

et al.

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Cited by 112 publications

(37 citation statements)

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“…Reagents for culture of the tumor cells and for the bioassay were described in a previous paper. 10) The instruments used in this study were a Shimadzu Double Beam Spectrometer UV-200S (UV spectra), JEOL JNM A-500 Spectrometer ( 1 H-NMR and 13 C-NMR spectra), JEOL JMS HX-110 Mass Spectrometer (MS spectra), and Yanaco Micro Melting Point Apparatus (mp).…”

mentioning

confidence: 99%

Antiproliferative Constituents in Plants. 10. Flavones from the Leaves of Lantana montevidensis BRIQ. and Consideration of Structure-Activity Relationship.

¹

,

²

,

³

et al. 2002

Biological & Pharmaceutical Bulletin

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Lantana camara L. is indigenous to tropical America, and its leaves have been used in folk medicine for the treatment of bronchitis and stomach disorders and as a sudorific, and are also put into baths to treat rheumatism in South America.2) However, this species has been known to be toxic to livestock, which develop hepatotoxicity and photosensitization on ingestion of the leaves.3) There have been many reports on the biological action of this plant and the toxic constituents. Scores of triterpene derivatives have been isolated, [3][4][5][6] and some of them have been reported to exhibit inhibitory activity against Epstein-Barr virus early antigen activation in Raji cells induced by 12-O-tetradecanoyl-phorbol-13-acetate. 7)L. montevidensis BRIQ. is native to Brazil (Montevideo), and the tea and infusion of the dried leaves have been used in folk medicine for the same purposes as L. camara.2) However, to our knowledge there is only one report on the essential oil from the leaves 2) and there is no report on the other constituents.Among several Verbenaceae plants in which we investigated the antiproliferative activity of the MeOH extracts, L. camara and L. montevidensis exhibited higher activity against tumor cell growth. The MeOH extract of the leaves of L. montevidensis showed 50% growth inhibition (GI 50 ) at the concentrations of 8 mg/ml for human gastric adenocarcinoma (MK-1), 3 mg/ml for human uterus carcinoma (HeLa), and 4 mg/ml for murine melanoma (B16F10), which were more potent than the inhibition by the MeOH extract of the leaves of L. camara (12.5 mg/ml for MK-1 and 25 mg/ml for HeLa and B16F10). The inhibitory activity was found to be localized in the nonglycoside fraction that contains several flavonoids. The nonflavonoid fraction exhibited higher activity, however, the flavonoid fraction also showed significant activity. We therefore first investigated the active constituents in the flavonoid fraction. This paper deals with the isolation and identification of the flavone constituents in the leaves of L. montevidensis and their antiproliferative activity. MATERIALS AND METHODS Materials, Reagents, and InstrumentsThe leaves of L. montevidensis were collected in Munakata City, Fukuoka, Japan, in July 2000 and air-dried. 6-Hydroxyluteolin, desmethoxycentaureidin, and jaceosidin were isolated from the herb of Lippia canescens KUNTH. (Verbenaceae), 1) and eupatilin was isolated from the herb of Artemisia ludoviciana NUTT. subsp. mexicana (WILLD. ex SPRENGEL) (Compositae). 8)Pectolinarigenin was obtained by acid hydrolysis of linariin isolated from the herb of Trifolium dubium SIBTH. (Leguminosae) and identification was performed by comparison of the NMR data with those reported. 9) Chrysin, luteolin, baicalein, and 6-and 7-methoxyflavones were purchased from Aldrich Chemical Company (Milwaukee, WI, U.S.A.). Reagents for culture of the tumor cells and for the bioassay were described in a previous paper.10) The instruments used in this study were a Shimadzu Double Beam Spectrometer UV-200S (UV spectra), JE...

“…Reagents for culture of the tumor cells and for the bioassay were described in a previous paper. 10) The instruments used in this study were a Shimadzu Double Beam Spectrometer UV-200S (UV spectra), JEOL JNM A-500 Spectrometer ( 1 H-NMR and 13 C-NMR spectra), JEOL JMS HX-110 Mass Spectrometer (MS spectra), and Yanaco Micro Melting Point Apparatus (mp).…”

mentioning

confidence: 99%

Antiproliferative Constituents in Plants. 10. Flavones from the Leaves of Lantana montevidensis BRIQ. and Consideration of Structure-Activity Relationship.

¹

,

²

,

³

et al. 2002

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

Lantana camara L. is indigenous to tropical America, and its leaves have been used in folk medicine for the treatment of bronchitis and stomach disorders and as a sudorific, and are also put into baths to treat rheumatism in South America.2) However, this species has been known to be toxic to livestock, which develop hepatotoxicity and photosensitization on ingestion of the leaves.3) There have been many reports on the biological action of this plant and the toxic constituents. Scores of triterpene derivatives have been isolated, [3][4][5][6] and some of them have been reported to exhibit inhibitory activity against Epstein-Barr virus early antigen activation in Raji cells induced by 12-O-tetradecanoyl-phorbol-13-acetate. 7)L. montevidensis BRIQ. is native to Brazil (Montevideo), and the tea and infusion of the dried leaves have been used in folk medicine for the same purposes as L. camara.2) However, to our knowledge there is only one report on the essential oil from the leaves 2) and there is no report on the other constituents.Among several Verbenaceae plants in which we investigated the antiproliferative activity of the MeOH extracts, L. camara and L. montevidensis exhibited higher activity against tumor cell growth. The MeOH extract of the leaves of L. montevidensis showed 50% growth inhibition (GI 50 ) at the concentrations of 8 mg/ml for human gastric adenocarcinoma (MK-1), 3 mg/ml for human uterus carcinoma (HeLa), and 4 mg/ml for murine melanoma (B16F10), which were more potent than the inhibition by the MeOH extract of the leaves of L. camara (12.5 mg/ml for MK-1 and 25 mg/ml for HeLa and B16F10). The inhibitory activity was found to be localized in the nonglycoside fraction that contains several flavonoids. The nonflavonoid fraction exhibited higher activity, however, the flavonoid fraction also showed significant activity. We therefore first investigated the active constituents in the flavonoid fraction. This paper deals with the isolation and identification of the flavone constituents in the leaves of L. montevidensis and their antiproliferative activity. MATERIALS AND METHODS Materials, Reagents, and InstrumentsThe leaves of L. montevidensis were collected in Munakata City, Fukuoka, Japan, in July 2000 and air-dried. 6-Hydroxyluteolin, desmethoxycentaureidin, and jaceosidin were isolated from the herb of Lippia canescens KUNTH. (Verbenaceae), 1) and eupatilin was isolated from the herb of Artemisia ludoviciana NUTT. subsp. mexicana (WILLD. ex SPRENGEL) (Compositae). 8)Pectolinarigenin was obtained by acid hydrolysis of linariin isolated from the herb of Trifolium dubium SIBTH. (Leguminosae) and identification was performed by comparison of the NMR data with those reported. 9) Chrysin, luteolin, baicalein, and 6-and 7-methoxyflavones were purchased from Aldrich Chemical Company (Milwaukee, WI, U.S.A.). Reagents for culture of the tumor cells and for the bioassay were described in a previous paper.10) The instruments used in this study were a Shimadzu Double Beam Spectrometer UV-200S (UV spectra), JE...

“…These maxima correspond to bands I and II, typical in this class of compounds. Analysis of the 1 H and 13 C NMR spectra of both compounds and comparison with literature data 8,9 allowed us to characterize them as eupafolin (3) and hispidulin (4).…”

Section: Resultsmentioning

confidence: 99%

“…In an early study 8 they showed significant cytotoxic action against KB cells. Anti-oxidant 15 and antihepatotoxic 16,17 properties have also been described for these compounds.…”

mentioning

confidence: 99%

“…Eupafolin has been found, for example, in E. cuneifolium 8 , E. cannabinum 10 and in E. subhastatum 11 while hispidulin has been found in E. cannabinum 8 , E. cuneifolium 9 , E. rotundifolium 8 , E. semiserratum 12 , E. serratum 13 and E. subhastatum 14 .…”

mentioning

confidence: 99%

See 1 more Smart Citation

HPLC analysis of flavonoids in Eupatorium littorale

et al. 2001

J. Braz. Chem. Soc.

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Neste trabalho são descritos o isolamento e a identificação de eupafolina e hispidulina das folhas secas de Eupatorium littorale (Asteraceae). Foi desenvolvido também um método para a detecção desses flavonóides e de rutina na planta, utilizando a técnica de CLAE em fase reversa com detetor de arranjo de fotodiodos. Eupafolina e hispidulina foram quantificados sendo encontradas as concentrações de 0,29% e 0,21%, respectivamente.The isolation and identification of eupafolin and hispidulin in the dried leaves of Eupatorium littorale (Asteraceae) are described. A method for the detection of those flavonoids and rutin was also developed using reversed-phase HPLC with a photodiode array detector. Eupafolin and hispidulin were quantified and the concentrations found were 0.29% and 0.21%, respectively.

“…This class of naturally occurring compounds are glycerol-3-phosphate dehydrogenase inhibitors 5 and cleave DNA through selective strand scission 6 . Previous investigation of the non polar ether fractions of the flowers of Ononis vaginalis resulted in the isolation of seven flavonoids 7. Among these, eupatilin is known to have a cytotoxic action against human carcinoma of nasopharynx 8 and trifolin proved to have an insect growth regulator like action 9 . However, the more polar butanol fraction was not subjected to more detailed investigation.…”

Section: Introductionmentioning

confidence: 99%

Two new norphenylpropanoid glucosides and hemipholin from the flowers of Ononis vaginalis

Abdel‐Kader¹

1997

J. Braz. Chem. Soc.

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