Chemical Constituents and Cytotoxic Effect of the Main Compounds of Lythrum salicaria L.

Abstract

Lythrum salicaria L. (Lythraceae), a herbaceous plant growing widely in Iran, has been well known for many centuries for its astringent and styptic properties. A phytochemical investigation of this plant, based on spectroscopic analysis, identifi ed fourteen compounds: 5-hydroxypyrrolidin-2-one (1), umbelliferone-6-carboxylic acid (2), 3,3',4'-tri-O-methylellagic acid-4-O-β-D-(2"-acetyl)-glucopyranoside (3), 3,3',4'-tri-O-methylellagic acid-4-O-β-D-glucopyranoside (4), daucosterol (5), phytol (6), dodecanoic acid (7), oleanolic acid (8), 3,3',4'-tri-O-methylellagic acid (9), corosolic acid (10), β-sitosterol (11), peucedanin (12), buntansin (13), and erythrodiol (14). All compounds, except for 8 and 11, have been isolated from L. salicaria for the fi rst time. Cytotoxic activities of the compounds were examined against three cancerous cell lines, colon carcinoma (HT-29), leukemia (K-562), and breast ductal carcinoma (T47D), and Swiss mouse embryo fi broblast (NIH-3T3) cells using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and methotrexate as positive control. Compounds 5, 10, 11, and 14 were the most active against the HT-29 cell line with IC 50 values of 192.7, 36.8, 38.2, and 12.8 μg/mL, respectively. Compounds 14, 11, 5, and 10 were 6.4, 2.8, 2.6, and 1.4 times, respectively, more selective than methotrexate. Compound 5 was the most active against the K-562 cell line (IC 50 = 50.2 μg/mL), with a selectivity exceeding that of methotrexate 13.3 times. The results of the cytotoxic assay confi rmed that growth and proliferation of the cancer cell lines are predominantly infl uenced by triterpene derivatives and sterols of this plant. ., 2003;Lopez et al., 2008;Tunalier et al., 2007). The plant extract decreases the blood glucose level in both hyperglycaemic and normoglycemic rats and rabbits (Lamela et al., 1986;Torres and Suarez, 1980). Flowering aerial parts of the plant have been traditionally used for the treatment of diarrhea, chronic intestinal catarrh, haemorrhoids, eczema, varicose veins, bleeding of the gums, and vaginitis (Mantle et al., 2000;Rauha et al., 2000). Evaluation of the antidiarrheal effect of Salicairine ® , a formulated medication, demonstrated that there was either a signifi cant increase in the colon net fl uid absorption or a decrease in the net fl uid secretion (Brun et al., 1997).We have previously analysed the extract and fractions of L. salicaria for cytotoxic activity against cancer cell lines using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Ethyl acetate and chloroform fractions of the plant exhibited cytotoxicity toward the T47D cancer cell line with IC 50 values of 63.1 and 108.2 μg/mL, respectively (Khanavi et al., 2011). The objective of the present study was the isolation and characterization of major constituents of L. salicaria through chromatographic and spectroscopic methods, respectively. We also demonstrated cytotoxic effects of the purifi ed compounds using the MTT assay against the three cancerous c...

Phenols and γ‐Lactams from the Aerial Part of Pseudolysimachion linariifolium subsp. dilatatum

“…dilatatum . By comparing their NMR and MS data with reported data, their structures were identified as linariifolioside ( 3 ), [5] 3′,4′,5,6,7‐pentahydroxyflavone‐7‐ O ‐ β ‐ d ‐glucosyl‐(1′′′→2′′)‐ β ‐ d ‐glucoside( 4 ), [3] syringaresinol‐ O ‐ β ‐ d ‐glucopyranoside ( 5 ), [19] eucommin A ( 6 ), [20] (+)‐pinoresinol‐ O ‐ β ‐ d ‐glucopyranoside ( 7 ), [21] pterolactam ( 8 ), [22] 5‐hydroxypyrrolidin‐2‐one ( 9 ), [23] 4‐ O ‐ β ‐ d ‐glucopyranosylvanillic acid ( 10 ), [24] protocatechuic acid ( 11 ), [25] catechol ( 12 ), [26] tachioside ( 13 ), [27] isotachioside ( 14 ), [28] and pyrocatechol 1‐ O ‐ β ‐ d ‐glucopyranoside ( 15 ) [29] . Among them, compounds 6 – 10 , 13 – 15 were identified for the first time in the genus Pseudolysimachion .…”

Antimutagenic activity of compounds isolated from Ajuga bracteosa Wall ex. Benth against EMS induced mutagenicity in mice

“…The β-sitosterol is known to be effective against a number of cancers like human breast cancer [ 15 ], colon carcinoma [ 16 ] and prostatic cancer [ 17 ]. The β-sitosterol also inhibits the proliferation of breast cancer cells in a dose dependent manner [ 18 ].…”

Podophyllum hexandrum ameliorates endosulfan-induced genotoxicity and mutagenicity in freshwater cyprinid fish crucian carp

“…Stigmasterol is known to possess many important biological activities like antihypercholesterolemic, antimutagenic, antileishmanial, antimalarial, antitrypanosomal, platelet aggregation inhibitor and antiviral (Zhou et al 2011). b-Sitosterol is known to be effective against a number of cancers like human breast cancer, colon carcinoma and prostatic cancer (Manayi et al 2013). The significant reduction in the CA and MN in the EE-F4-treated group in our study might be attributed to different mechanism, other than antioxidant potential, of the parent compound podophyllotoxin and needs further study.…”