Cytotoxic Diarylheptanoids from the Roots of Juglans mandshurica

Abstract

A new (2) and three known diarylheptanoids (1, 3, and 4), along with one known sesquiterpenoid (5), were isolated from the roots of Juglans mandshurica, and their structures were elucidated on the basis of spectroscopic studies. Four of these compounds (2-5) exhibited moderate cytotoxicities against human colon carcinoma and human lung carcinoma cell lines with IC(50)'s ranging from 2 to 25 microg/mL.

New Cytotoxic Diarylheptanoids from the Rhizomes of Alpinia officinarum

“…3), thus the structure of 2 was established as (2S)-1,7-diphenyl-2-hydroxy-4E-hepten-3-one. The other fifteen known diarylheptanoids were also isolated from this plant and identified by comparing spectral data with those reported in literature; they were 3,6-furan-1,7-diphenylheptane (3) [8], 7-(4′′-hydroxy-3′′-methoxyphenyl)-1-phenyl-3,5-heptanediol (4) [9], (3R,5R)-1,7-diphenyl-3,5-heptanediol (5) [10], (5S)-5-hydroxy-7-(4′′-hydroxy-3′′-methoxyphenyl)-1-(4′-hydroxyphenyl)-3-heptanone (6) [6], (5S)-7-(4′′-hydroxy-3′′-methoxyphenyl)-1-(4′-hydroxyphenyl)-5-methoxy-3-heptanone (7) [6], (5S)-5-hydroxy-7-(4′′-hydroxyphenyl)-1-phenyl-3-heptanone (8) [9], (5S)-7-(4′′-hydroxyphenyl)-5-methoxy-1-phenyl-3-heptanone (9) [11], (5S)-1,7-diphenyl-5-methoxy-3-heptanone (10) [11], (5R)-5-hydroxy-7-(4′′-hydroxy-3′′-methoxyphenyl)-1-phenyl-3-heptanone (11) [12], (5R)-7-(4′′-hydroxy-3′′-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone (12) [13], (5R)-1,7-diphenyl-5-hydroxy-3-heptanone (13) [12], 7-( 4 ′ ′-hydroxy-3′′-methoxyphenyl)-1-phenyl-4E-hepten-3-one (14) [12], 7-(4′′-hydroxyphenyl)-1-phenyl-4E-hepten-3-one (15) [14], 1,7-diphenyl-4E-hepten-3-one (16) [13] and 7-(4′′-hydroxy-3′′-methoxyphenyl)-1-(4′-hydroxyphenyl)-4E-hepten-3-one (17) [14]. Compound 3 is a new natural product isolated from plants for the first time.…”

Juglanthraquinone C, a novel natural compound derived from Juglans mandshurica Maxim, induces S phase arrest and apoptosis in HepG2 cells

“…In recent years, a number of natural compounds, such as phenolics, naphthoquinones, tetralones, flavonoids, naphthalenyl glucosides, diarylheptanoid and galloyl glycosides, have been isolated from Juglans species [1,2]. These compounds show several biological activities including cytotoxicity, anti-oxidation, inhibition of topoisomerase I and II, ribonuclease H, HIV-1 reverse transcriptase and pancreatic lipase as well as anti-complement activity [2][3][4][5][6][7][8]. In our previous study, 38 chemicals were extracted from J. mandshurica, including one newly discovered anthracene derivative, two new anthraquinones, and one new naturally occurring anthraquinone compound (Juglanthraquinone C, JC) that has shown strong cytotoxicity [9].…”

Antioxidative Activities of Galloyl Glucopyranosides from the Stem-Bark ofJuglans mandshurica

“…It has also been shown that these constituents exhibited inhibitory effects on DNA polymerase and RNase H activity, 8,10) as well as cytotoxic, 5,8,9) anti-HIV-1, 11) and anti-complement activities. 12) In this study, two galloyl monosaccharides, 1,2,6-trigalloyl glucose (1) and 1,2,3,6-tetragalloyl glucose (2), isolated from J. mandshurica were examined for their scavenging activities against some free y To whom correspondence should be addressed.…”

“…3) A number of natural phenolics, naphthoquinones, naphthalenyl glucosides, tetralones, [5][6][7][8] diarylheptanoids, 5,[7][8][9] galloyl monosaccharides, and flavonoids 5,10) have previously been isolated from this plant. It has also been shown that these constituents exhibited inhibitory effects on DNA polymerase and RNase H activity, 8,10) as well as cytotoxic, 5,8,9) anti-HIV-1, 11) and anti-complement activities.…”