Antiproliferative Constituents in the Plants 7. Leaves of Clerodendron bungei and Leaves and Bark of C. trichotomum.

Abstract

The constituents of the leaves of Clerodendron bungei STEUD. (Verbenaceae) and leaves and bark of C. trichotomum THUNB. were investigated guided by the antiproliferative activity against three tumor cell lines (MK-1: human gastric adenocarcinoma, HeLa: human uterus carcinoma, and B16F10: murine melanoma). Two phenylethanoid glycoside caffeic acid esters, acteoside and isoacteoside, were isolated as the constituents which selectively inhibit the growth of B16F10 cells.The antiproliferative activities against B16F10 cells of acteoside (GI 50 : 8 m mM), isoacteoside (8 m mM) and their methanolysis products, methyl caffeate (26 m mM), 3,4-dihydroxyphenethyl alcohol (8 m mM), 3,4-dihydroxyphenethyl glucoside (10 m mM), desrhamnosyl acteoside (6 m mM), and desrhamnosyl isoacteoside (6 m mM) suggested that the 3,4-dihydroxyphenethyl alcohol group might be more responsible for the activities of acteoside and isoacteoside than the caffeoyl group. The activities of chlorogenic acid, 3,4-dihydroxyphenylacetic acid, 3-(3,4-dihydroxyphenyl) alanine, 3,4-dihydroxy-phenethylamine hydrochloride, ferulic acid, sinapic acid, and five dihydroxybenzoic acids were also determined and compared with those of the above compounds.

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

“…When we compared the activities of 3Ј,4Ј-di-OH-flavones [luteolin, 6-hydroxyluteolin, eupafolin (11), and cirsiliol (8)], the influence of 5-OH-6,7-di-OCH 3 appears slightly greater, but that of 5,7-di-OH, 5,6,7-tri-OH, and 5,7-di-OH-6-OCH 3 are almost the same. However, the order is 5,7-di-OHϾ5,7-di-OH-6-OCH 3 for apigenin (10) vs. hispidulin (9), 5,7-di-OH-6-OCH 3 Ͼ5-OH-6,7-di-OCH 3 for desmethoxycentaureidin vs. eupatorin (2), and 5,6-di-OH-7-OCH 3 · 5-OH-6,7-di-OCH 3 for 5 vs. 3. Values are means of four determinations.…”

“…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).…”

“…10) Extraction and Fractionation The dried leaves (50 g) were extracted three times with MeOH (300 ml) under reflux for 1 h. The MeOH extract (15 g) was suspended in 60% MeOH and passed through a column of styrene polymer, Diaion HP 20 (200 ml), and the column was successively washed with 60% MeOH, MeOH, and then AcOEt. The 60% MeOH eluate was concentrated to remove MeOH, and the aqueous solution was passed through a new column of Diaion HP 20 (100 ml) and washed with H 2 Table 1.…”

Antiproliferative Constituents in the Plant 8. Seeds of Rhynchosia volubilis.

“…A similar result has already been reported against rat hepatoma (dRLh-84) cells by Inoue et al 12) We have also observed the phenomenon that the antiproliferative activity of caffeic acid is lowered by esterification. 1) In spite of structural differences, 5 and 3 showed similar activity. Since the activity of catechin was less potent than that of 3 (not shown), the presence of the galloyl group would be a key factor for antiproliferative activity.…”

Evaluation of Variation of Acteoside and Three Major Flavonoids in Wild and Cultivated Scutellaria baicalensis Roots by Micellar Electrokinetic Chromatography.

“…13) Furthermore, anti-oxidant activity 14,15) of SR is regarded as a potential cure for hepatitis, inflammation and other chronic diseases. Therefore, acteoside with potent antioxidant properties could offer important biological functions of SR.…”