Eighteen lignans were isolated from an ethanol extract of Machilus robusta by a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20 and reversed-phase HPLC. Their structures were identified by spectroscopic data analysis as isolariciresinol-9'-O-beta-D-xylopyranoside (1), (+)-5'-methoxy-isolariciresinol-9'-O-beta-D-xylopyranoside(2), lyoniresinol-9'-O-beta-D-xylopyranoside(3), (+)-(8S, 8'S) -4, 4'-dihydroxy-3, 3', 5, 5'-tetramethoxylignan-9, 9'-diol 9-O-beta-D-xylopyranoside (ssioriside, 4), lyoniresinol (5), meso-dihydroguaiaretic acid (6), (+)-(8S, 8'R)-3', 4, 4'-trihydroxy-3'-methoxylignan (7), (8S, 8'R)-4'-hydroxy-3, 3', 4-trimethoxylignan (meso-monomethyl dihydroguaiaretic acid, 8), (+)-guaiacin (9), isoguaiacin (10), (-)-(7'R, 8R, 8'R)-4, 4'-dihydroxy-3, 3', 5-trimethoxy-2, 7'-cyclolignan (11), henricine B (12), (-)-(7S, 7'S, 8R, 8'R)-4, 4'-dihydroxy-3, 3', 5, 5'-tetramethoxy-7, 7'-epoxylignan-9, 9'-dio] (7S, 7'S, 8R, 8'R-icariol A2, 13), (+)-(7R, 8R, 7'E)-4-hydroxy-3, 5'-dimethoxy-7, 4'-epoxy-8, 3'-neolignan-7'-ene (licarin A, 14), nectandrin B (15), machilin-I (16), (-)-pinoresinol (17), and (-)-syringaresinol (18). All compounds were isolated from this plant for the first time. In the preliminary assay, compound 17 showed inhibitory activity against NO secretion of mouse peritoneal macrophages with an inhibition rate of 72.2% at 10 micromol x L(-1).
Download full-text PDF |
Source |
|---|
Publication Analysis
Top Keywords
Similar Publications
Sucrose esters of aryldihydronaphthalene-type lignans, and antitumor activity of extracts of (Forssk.) aerial parts.
Nat Prod Res
April 2024
Chemistry Department, Faculty of Science, Port Said University, Port Said, Egypt.
One new compound 3f-[(7',8')-4,4'-dihydroxy-5-methoxy-2,7'-cycloligna-7-en-9-methoxycarbonyl, 9'-carbonyl--] -- D-fructofuranosyl- (→)-- D-glucopyranoside) (Moltkiopsin A) was isolated and identified from the extract of aerial parts of the wild Egyptian plant (Frossk.), family Boraginaceae, for the first time, along with two aryldihydronaphthalene lignans 3f→9':6f→9-[(7',8')-4,4'- dihydroxy-3,3',5-trimethoxy-2,7'-cycloligna-7-en-9,9'-dicarbonyl]-6g-acetyl--D-gluco pyranosyl-(→) --D-fructofuranoside (Trigonotin A) which was reported for the first time from this plant species and a known compound 3f→9':6f→9-[(7',8')-4,4'- dihydroxy-3,3',5-trimethoxy-2,7'-cycloligna-7-en-9,9'-dicarbonyl]--D-gluco pyranosyl - (→)- -D- fructofuranoside (Trigonotin C) . These compounds were separated and purified using different chromatographic techniques and their structures were elucidated by extensive 1D (H and C NMR), and 2D NMR (COSY, HSQC, and HMBC), besides ESI-MS spectral methods.
View Article and Find Full Text PDFTwo novel polyketones from the leaves and twigs of .
J Asian Nat Prod Res
March 2022
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China.
Article Synopsis
- - Two new polyketones, clerodendruketone A and B, were discovered alongside four known compounds from the leaves and twigs of a plant, with their structures analyzed using NMR, HRESIMS, and ECD data.
- - The antioxidant properties of these compounds were evaluated using a DPPH assay, while their antibacterial activities against specific bacteria were assessed through a turbidimetry assay.
- - Findings revealed that clerodendruketones A and B exhibited significant antibacterial activity, while clerodendruketone A showed moderate antioxidant effects.
[Lignans from seed of Hydnocarpus anthelminthica].
Zhongguo Zhong Yao Za Zhi
April 2019
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College Beijing 100050, China.
This project is to investigate lignans from the seed of Hydnocarpus anthelminthica. Thirteen lignans were isolated from the 95% ethanol extract of the seed of H. anthelminthica, by polyamide resin, Sephadex LH-20, ODS column chromatography and preparative HPLC.
View Article and Find Full Text PDFTwo new lignans, named (7R, 8S)-balanophonin (1) and (7R, 8S)-tomentosanan A (2), together with eight known lignans, burselignan (3), (+)-isolariciresinol (4), (+)-lyoniresinol (5), 5-methoxy-(+)-isolariciresinol (6), (-)-syringaresinol (7), (+)-epipinoresinol (8), (-)-(7'S, 8S, 8'R)-4,4'-dihydroxy-3, 3', 5, 5'-. tetramethoxy-7', 9-epoxy-lignan-9'-ol-7-one (9), and (-)-(7R, 8S)-dihydrodehydrodiconiferyl alcohol (10) were isolated from the whole plants of Hedyotis uncinella Hook. et Am.
View Article and Find Full Text PDFTwo new compounds from the roots of Ilex pubescens and their cytotoxic activity.
J Nat Med
July 2016
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, 103 Wenhua Rd, Shenyang, 110016, People's Republic of China.
A new phenylethanoid, 1-O-β-D-(4-hydroxyphenyl)-ethyl-6-O-vanilloyl-glucopyranoside (1), and a new furofuran lignan, (7R,7'R,7''S,8S,8'S,8''R)-4', 4''-dihydroxy-3,3',3'',5-tetramethoxy-7,9':7'9-diepoxy-4,8''-oxy-8,8'-sesquineolignan-7'',9''-diol (2), along with five known compounds (3-7) were isolated from the roots of Ilex pubescens. Their chemical structures were elucidated on the basis of extensive spectroscopic analysis, including UV, IR, MS, and NMR experiments. In addition, compounds 2-7 were evaluated in vitro for their cytotoxic effects on human HeLa cells; among them, compounds 2, 3, 6, and 7 showed cytotoxic activity against HeLa cells in the test.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!