Bioassay-guided isolation of Poliovirus-inhibiting constituents from Zephyranthes candida

Abstract

Context: Plants of the Zephyranthes genus are globally used in folk medicine. In a previous study, Zephyranthes candida Linn. (Amaryllidaceae) was identified as having antiviral properties; this led to anti-poliovirus assay-guided isolation of compounds from crude methanol extract of the plant.

Objective: Isolation of anti-poliovirus constituents from Z. candida.

Material and methods: Active chloroform fraction from crude methanol extract of Z. candida (whole plant) was subjected to bioassay-guided fractionation; repeated column and preparative thin layer chromatography led to isolation of active compounds. Chemical structures were identified using spectroscopic techniques. Using serial two-fold dilution of maximum non-toxic concentration (MNTC) of each compound (0.0625–1?µg/mL for lycorine and 0.625–10?µg/mL for trisphaeridine and 7-hydroxy-3′,4′-methylenedioxyflavan), the ability of extracts to inhibit viral-induced cell death in tissue culture was evaluated 72?h post-infection by the colorimetric method using MTT (3-[4,5-dimethylthiazol–2-yl]-2,5-diphenyltetrazolium bromide) dye. Regression analysis was used to determine 50% inhibitory concentration (IC₅₀) and 50% cytotoxicity concentration (CC₅₀), from which selective index (SI) was calculated.

Results: From the chloroform fraction, three compounds were isolated and identified, namely lycorine (1), trisphaeridine (2), and 7-hydroxy-3′,4′-methylenedioxyflavan (3) as the anti-polioviral components. Lycorine was the most active, with an IC₅₀ value of 0.058?µg/mL followed by trisphaeridine (2) with an IC₅₀ of 0.1427?µg/mL, and 7-hydroxy-3′,4′-methylenedioxyflavan (3) with an IC₅₀ of 0.2384?µg/mL.

Discussions and conclusions: The antipoliovirus activity of trisphaeridine (2) and 7-hydroxy-3′,4′-methylenedioxyflavan (3) is established in this report; these compounds are of moderate toxicity and have very good SI. They could be a potential template for the development of a new antiviral agent.     

Chemical constituents from the leaves of Boehmeria rugulosa with antidiabetic and antimicrobial activities

Three new flavonoid glycosides, named chalcone-6′-hydroxy-2′,3,4-trimethoxy-4′-O-β-d-glucopyranoside (1), isoflavone-3′,4′,5,6-tetrahydroxy-7-O-{β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside} (2), and isoflavone-3′,4′,5,6-tetrahydroxy-7-O-{β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside} (3), were isolated from the leaves of Boehmeria rugulosa, together with five known compounds, β-sitosterol, quercetin, 3,4-dimethoxy-ω-(2′-piperidyl)-acetophenone (4), boehmeriasin A (5), and quercetin-7-O-β-d-glucopyranoside. The structures of the isolated compounds were determined by means of chemical and spectral data including 2D NMR experiments. The ethanolic extract of leaves showed significant hypoglycemic activity on alloxan-induced diabetic mice. Glibenclamide, an oral hypoglycemic agent (5 mg/kg, p.o.), was used as a positive control. The ethanolic extract of the plant as well as the isolated compounds 1–3 (25 μg/ml) showed potent antimicrobial activity against two bacterial species (Staphylococcus aureus and Streptococcus mutans) and three fungus pathogens (Microsporum gypseum, Microsporum canis, and Trichophyton rubrum). The activities of the isolated compounds 1–3 have been compared with positive controls, novobiocin, and erythromycin (15 μg/ml).     

Cytotoxic C-Methylated Chalcones from Syzygium samarangense.

Abstract

The flavonoids 2′-hydroxy-4′,6′-dimethoxy-3′-methylchalcone (1), 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethylchalcone (2), 2′,4′-dihydroxy-6′-methoxy-3′-methylchalcone (3), 2′,4′-dihydroxy-6′-methoxy-3′-methyldihydrochalcone (4) and 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethyldihydrochalcone (5), isolated from Syzygium samarangense. (Blume) Merr. & L.M. Perry (Myrtaceae), were subjected to cytotoxicity testing using the dimethylthiazoldiphenyl tetrazolium (MTT) assay. The cell lines used were the Chinese hamster ovarian (CHO-AA8) and the human mammary adenocarcinoma, (MCF-7 and SKBR-3). Among the test compounds, 2 exhibited significant differential cytotoxicity against the MCF-7 cell line with an IC₅₀ of 0.0015 ± 0.0001 nM. It was also cytotoxic against the SKBR-3 cell line with an IC₅₀ of 0.0128 ± 0.0006 nM. Doxorubicin, the positive control, had an IC₅₀ of 2.60 ± 0.28 × 10^?4 nM against the MCF-7 cell line and an IC₅₀ of 2.76 ± 0.52 × 10^?5 nM against the SKBR-3 cell line. When tested in a mechanism-based yeast bioassay for detecting DNA-damaging agents using genetically engineered Saccharomyces cerevisiae. RS322Y (RAD52) mutant strain and (LF15/11) (RAD+) wild-type strain, 2 showed significant selective cytotoxicity against the RAD52 yeast mutant strain. It had an IC₁₂ of 0.1482 nM, as compared with the positive control, streptonigrin, which had an IC₁₂ of 0.0134 nM. Hence, 2 is a cytotoxic natural product with potential anticancer application.     

Four new diterpenoids isolated from the Euphorbia rapulum

Four new diterpenoids named 1-epi-9-hydroxydepressin (1), 1-epi-8-hydroxydepressin (2), 2,13,9-trihydroxy-labda-8(17),12(E),14-triene (3) and tagalsin I (4) were isolated from Euphorbia rapulum. The structures of these compounds were elucidated by means of various spectroscopic methods. All the isolated compounds were evaluated for cytotoxic activities against HepG2, MCF-7, and C6 cell lines, and compound 4 showed moderate selective activity against MCF-7 cell line with an IC₅₀ value of 31.8 μM.     

Antioxidant and cytotoxic activity of polyphenolic compounds isolated from the leaves of Leucenia leucocephala

Context: Cancer is a serious clinical problem to the health care system. Anticancer drugs have been extracted from plants containing phenolic compounds. Leucenia species (Fabaceae) contain a variety of bioactive components of numerous biological and pharmacological properties.

Objective: This study explored the constitutive polyphenols of Leucenia leucocephala Lam. growing in Egypt and evaluated the antioxidant and cytotoxic activity.

Materials and methods: Chemical structures of the isolated compounds from the leaves of L. leucocephala were established by spectral techniques (UV, ¹H, and ¹³C NMR, MS).

Results: Chromatographic separation of 80% MeOH extract of the leaves of L. leucocephala have resulted in a novel flavonoid-galloyl glycoside [myricetin 3-O-(2′,3′4′-tri-O-galloyl)-α-l-rhamnopyranoside] with three known polyphenolic compounds isolated for the first time from this species (apigenin 7-O-β-d-glucuronopyranoside methyl ester, luteolin 7-O-β-d-glucuronopyranoside methyl ester, and 1,3,6-tri-O-galloyl-β-d-glucopyranose) and seven known previously isolated compounds. Also, 80% methanol extract exhibited high antioxidant activity (SC₅₀?=?3.94 µg/ml), which is correlated with its phenolic content. The extract also showed cytotoxic activity against Hep G2 (IC₅₀ value 1.41 µg/ml) confirming its anticancer activity against hepatocellular carcinoma. Among the tested compounds (4–8) for antioxidant property, compound 7 was the most active compound (SC₅₀?=?2.49 µg/ml). Also compounds 7 and 8 exhibited high cytotoxic activity (IC₅₀?=?2.41 and 2.81 µg/ml, respectively).

Discussion and conclusion: These findings demonstrate that the leaves of L. leucocephala contain a considerable amount of polyphenolic compounds with high antioxidant properties, thus it has great potential as a source for natural health products.     

In Vitro Antibacterial and Antifungal Activities of Extracts and Compounds from Uvaria scheffleri

Petroleum ether, dichloromethane, and ethanolic extracts of the stem bark and leaves of Uvaria scheffleri Diels (Annonaceae) exhibited antifungal activity against Aspergillus niger (wild strain), Aspergillus fumigatus (wild strain), and a Penicillium species (wild strain). The ethanol extract of the stem bark was also active against Candida albicans (Strain H6392). The dichloromethane extract of the leaves showed the highest antifungal activity and in addition it showed antibacterial activity against Staphylococcus aureus (NCTC 6571). Fractionation of the dichloromethane extract of the leaves yielded nine known compounds. They included a 1 : 1 mixture of stigmasterol (1) and β-sitosterol (2), which showed antifungal activity against Candida albicans. Others were 3-farnesylindole (3), 2′,6′-dihydroxy-3′,4′-dimethoxy-chalcone (4), 2′-hydroxy-3′,4′,6′-trimethoxychalcone (5), 5-hydroxy-7,8-dimethoxyflavanone (6), 5,7,8-trimethoxyflavanone (7), and a 3 : 2 mixture of 2′,6′-dihydroxy-4′-methoxychalcone (8) and 5,7-dihydroxyflavone (9). Compound 7 and the mixture of compounds 8 and 9 showed antibacterial activity against Escherichia coli (NCTC 10418, MIC 125 µg/ml) and Staphylococcus aureus (MIC 125 µg/ml), respectively. The mixture of compounds 8 and 9 was also active against Candida albicans (MIC 31.25 µg/ml), Aspergillus niger, Aspergillus fumigatus, and the Penicillium species (MIC 1000 µg/ml). We conclude that Uvaria scheffleri extracts contain compounds with antifungal and antibacterial activity. The activities observed in this study are weak. Based on previous studies, it is being speculated that, possibly, the most active compounds were lost during fractionation. Further work to isolate more antifungal and antibacterial compounds is suggested.     

Terpenoids and bisbibenzyls from Chinese liverworts Conocephalum conicum and Dumortiera hirsuta

Four new monoterpene esters, 2α,5β-dihydroxybornane-2-cinnamate (1), 2α,5β-dihydroxybornane-5-acetyl-2-cinnamate (2), 2α,5β-dihydroxybornane-2-p-hydroxycinnamate (3) and 2α,5β-dihydroxy-bornane-2-cis-p-hydroxycinnamate (4), together with a known compound 3,4-dimethoxystyrene (5) were isolated from Chinese liverwort Conocephalum conicum and six known compounds, 5,7-dihydroxycalamenene (6), 7-hydroxycalamenene (7), lunularin (8), riccardin C (9), marchantin C (10) and riccardin D (11) were isolated from Dumortiera hirsuta. Their structures were elucidated by extensive spectral analysis and chemical correlations. Compounds 1 and 8 showed moderate cytotoxicity against human HepG2 cells with IC₅₀ 4.5 μg/ml and 7.4 μg/ml, respectively, while compound 8 also showed antimicrobacterial activity against Pseudomonas aeruginosa with minimum inhibitory concentration at 64 μg/ml.     

A new cytotoxic homoisoflavonoid from Dracaena cambodiana

A new homoisoflavonoid, named cambodianol (1), together with the two known flavanes, (2S)-7,3′-dihydroxy-4′-methoxy-8-methylflavane (2) and (2R)-7,4′-dihydroxy-8-methylflavane (3), were isolated from the stems of Dracaena cambodiana. Their structures were determined based on HR-ESI-MS and spectroscopic techniques (UV, IR, 1D-, and 2D-NMR). Compound 1 exhibited significant cytotoxic activities against K562 and SGC-7901 with the IC₅₀ values of 1.4 and 2.9 μg/ml, respectively.     

Three new C-alkylated flavonoids from Desmodium oblongum

Three new C-alkylated flavonoids, 4′-hydroxy-8-isobutyryl-7-methoxy-6-methyl-flavone (1), 4′,7-dimethoxy-8-isobutyryl-6-methyl-flavone (2), and 4′,7-dimethoxy-8-isobutyryl-flavone (3), together with three know ones luteolin (4), kaemferol (5), and quercetin (6), were isolated from Desmodium oblongum. Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. Compound 1 showed cytotoxicity against NB4, SHSY5Y, and MCF7 cell lines with IC₅₀ values of 8.5, 6.5, and 7.8 μM; compound 2 showed cytotoxicity against SHSY5Y and PC3 cell lines with IC₅₀ values of 5.0 and 6.8 μM; compound 3 displayed cytotoxicity against SHSY5Y and MCF7 cell lines with IC₅₀ values of 6.4 and 9.4 μM, respectively.     

Compounds from Sedum caeruleum with antioxidant,anticholinesterase, and antibacterial activities

Context: This is the first study on the phytochemistry, antioxidant, anticholinesterase, and antibacterial activities of Sedum caeruleum L. (Crassulaceae).

Objective: The objective of this study is to isolate the secondary metabolites and determine the antioxidant, anticholinesterase, and antibacterial activities of S. caeruleum.

Materials and methods: Six compounds (1–6) were isolated from the extracts of S. caeruleum and elucidated using UV, 1D-, 2D-NMR, and MS techniques. Antioxidant activity was investigated using DPPH^?, CUPRAC, and ferrous-ions chelating assays. Anticholinesterase activity was determined against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes using the Ellman method. Antibacterial activity was performed according to disc diffusion and minimum inhibitory concentration (MIC) methods.

Results: Isolated compounds were elucidated as ursolic acid (1), daucosterol (2), β-sitosterol-3-O-β-d-galactopyranoside (3), apigenin (4), apigetrin (5), and apiin (6). The butanol extract exhibited highest antioxidant activity in all tests (IC₅₀ value: 28.35?±?1.22?µg/mL in DPPH assay, IC₅₀ value: 40.83?±?2.24?µg/L in metal chelating activity, and IC₅₀ value: 23.52?±?0.44?µg/L in CUPRAC), and the highest BChE inhibitory activity (IC₅₀ value: 36.89?±?0.15?µg/L). Moreover, the chloroform extract mildly inhibited (MIC value: 80?µg/mL) the growth of all the tested bacterial strains.

Discussion and conclusion: Ursolic acid (1), daucosterol (2), β-sitosterol-3-O-β-d-galactopyranoside (3), apigenin (4), apigetrin (5), and apiin (6) were isolated from Sedum caeruleum for the first time. In addition, a correlation was observed between antioxidant and anticholinesterase activities of bioactive ingredients of this plant.     

Terpenoids from the tuber of Cremastra appendiculata

Two new terpenoids including a cadinane sesquiterpene (1), and an ent-kaurane diterpene diglycoside (2), together with a known triterpene containing 32 carbons (3), have been isolated from the ethanolic extract of Cremastra appendiculata. Their structures were established by the spectroscopic methods including the IR, MS, 1D-, and 2D-NMR experiments as ( ? )-cadin-4,10(15)-dien-11-oic acid (1), ( ? )-ent-12β-hydroxykaur-16-en-19-oic acid, 19-O-β-d-xylopyranosyl-(1 → 6)-O-β-d-glucopyranoside (2), and (+)-24,24-dimethyl-25,32-cyclo-5α-lanosta-9(11)-en-3β-ol (3). Compounds 1–3 were evaluated against several human cancer cell lines. Compound 3 showed in vitro-selective cytotoxicity against human breast cancer cell lines (MCF-7) with an IC₅₀ of 3.18 μM, but 1 and 2 were inactive (IC₅₀>10 μg/ml).     

Three new amides from Microlepia pilosissima

Phytochemical investigation of 70% EtOH extract of the dry fronds of Microlepia pilosissima has resulted in isolation of three new amides, (7E)-N-(3′-hydroxyl-4′-methoxy)-phenylethyl-4-hydroxyl-cinnamamide (1), (7E)-N-(3′,4′,5′-trihydroxyl)-phenylethyl-4-hydroxyl-cinnamamide (2), and (7E)-N-(3′,4′,5′-trihydroxyl)-phenylethyl-4-methoxy-cinnamamide (3). Their structures were characterized by spectroscopic analysis and chemical method, including 1D NMR, 2D NMR, and HR-ESI-MS.     

Degranulation inhibitors from the arils of <Emphasis Type="Italic">Myristica fragrans</Emphasis> in antigen-stimulated rat basophilic leukemia cells

A methanol extract of mace, the aril of Myristica fragrans (Myristicaceae), was found to inhibit the release of β-hexosaminidase, a marker of antigen-IgE-stimulated degranulation in rat basophilic leukemia cells (RBL-2H3, IC₅₀ = 45.7 μg/ml). From the extract, three new 8-O-4′ type neolignans, maceneolignans I–K (1–3), were isolated, and the stereostructures of 1–3 were elucidated based on spectroscopic and chemical evidence. Among the isolates, maceneolignans A (5), D (6), and H (8), (?)-(8R)-?^8′-4-hydroxy-3,3′,5′-trimethoxy-8-O-4′-neolignan (13), (?)-(8R)-?^8′-3,4,5,3′,5′-pentamethoxy-8-O-4′-neolignan (14), (?)-erythro-(7R,8S)-?^8′-7-acetoxy-3,4-methylenedioxy-3′,5′-dimethoxy-8-O-4′-neolignan (17), (+)-licarin A (20), nectandrin B (24), verrucosin (25), and malabaricone C (29) were investigated as possible degranulation inhibitors (IC₅₀ = 20.7–63.7 μM). These inhibitory activities were more potent than those of the antiallergic agents tranilast (282 μM) and ketotifen fumalate (158 μM). Compounds 5, 25, and 29 also inhibited antigen-stimulated tumor necrosis factor-α production (IC₅₀ = 39.5–51.2 μM), an important process in the late phase of type I allergic reactions.     

Flavonoids from the leaves of Pleioblastus argenteastriatus

A new flavonoid, 5,7,3′-trihydroxy-6-C-β-d-digitoxopyranosyl-4′-O-β-d-glucopyranosyl flavonoside (1), along with four known flavonoids 5,7,4′-trihydroxy-3′,5′-dimethoxy flavone (2), 5,3′,4′-trihydroxy-7-O-β-d-glucopyranosyl flavonoside (3), 5,4′-dihydroxy-3′,5′-dimethoxy-7-O-β-d-glucopyranosyl flavonoside (4), 5,3′,4′-trihydroxy-6-C-[β-d-glucopyranosyl-(1 → 6)]-β-d-glucopyranosyl flavonoside (5) were isolated from 95% EtOH extract of the leaves of Pleioblastus argenteastriatus. Their structures were determined on the basis of spectroscopic techniques and chemical methods.     

A new thiophene and two new monoterpenoids from Xanthium sibiricum

Three new compounds (1–3), together with six known compounds (4–9), were isolated from the fruits of Xanthium sibiricum. The structures and the absolute configurations of sibiricumthionol (1), (+)-(5Z)-6-methyl-2-ethenyl-5-hepten-1,2,7-triol [(+)-2], ( ? )-(5Z)-6-methyl-2-ethenyl-5-hepten-1,2,7-triol [( ? )-2], (2E,4E,1′S, 2′R, 4′S, 6′R)-dihydrophaseic acid (3), (+)-xanthienopyran [(+)-4] and ( ? )-xanthienopyran [( ? )-4] were established by extensive spectroscopic analyses, X-ray crystallographic analysis, ECCD analysis and ECD calculations. Caffeic acid (7) and caffeic acid ethyl ester (8) weekly inhibited α-glucosidase enzymatic activity by 44.5% and 40.2%, respectively, at 40 μM. Protocatechuic acid (9) selectively exhibited cytotoxicity against HepG2 cell lines, with an IC₅₀ value of 2.92 μM.     

Anti-inflammatory and anticholinesterase activity of six flavonoids isolated from <Emphasis Type="Italic">Polygonum</Emphasis> and <Emphasis Type="Italic">Dorstenia</Emphasis> species

This study was aimed at investigating the anti-inflammatory and anticholinesterase activity of six naturally occurring flavonoids: (?) pinostrobin (1), 2′,4′-dihydroxy-3′,6′-dimethoxychalcone (2), 6-8-diprenyleriodictyol (3), isobavachalcone (4), 4-hydroxylonchocarpin (5) and 6-prenylapigenin (6). These compounds were isolated from Dorstenia and Polygonum species used traditionally to treat pain. The anti-inflammatory activity was determined by using the Griess assay and the 15-lipoxygenase inhibitory activity was determined with the ferrous oxidation-xylenol orange assay. Acetylcholinesterase inhibition was determined by the Ellman’s method. At the lowest concentration tested (3.12 µg/ml), compounds 2, 3 and 4 had significant NO inhibitory activity with 90.71, 84.65 and 79.57 % inhibition respectively compared to the positive control quercetin (67.93 %). At this concentration there was no significant cytotoxicity against macrophages with 91.67, 72.86 and 70.86 % cell viability respectively, compared to 73.1 % for quercetin. Compound 4 had the most potent lipoxygenase inhibitory activity (IC₅₀ of 25.92 µg/ml). With the exception of (?) pinostrobin (1), all the flavonoids had selective anticholinesterase activity with IC₅₀ values ranging between 5.93 and 8.76 µg/ml compared to the IC₅₀ 4.94 µg/ml of eserine the positive control. These results indicate that the studied flavonoids especially isobavachalcone are potential anti-inflammatory natural products that may have the potential to be developed as therapeutic agents against inflammatory conditions and even Alzheimer’s disease.     

Three new α-pyrone derivatives from the plant endophytic fungus Penicillium ochrochloronthe and their antibacterial,antifungal, and cytotoxic activities

Three new 3,4,6-trisubstituted α-pyrone derivatives, namely 6-(2′R-hydroxy-3′E,5′E-diene-1′-heptyl)-4-hydroxy-3-methyl-2H-pyran-2-one (1), 6-(2′S-hydroxy-5′E-ene-1′-heptyl)-4-hydroxy-3-methyl-2H-pyran-2-one (2), and 6-(2′S-hydroxy-1′-heptyl)-4 -hydroxy-3-methyl-2H-pyran-2-one (3), together with one known compound trichodermic acid (4), were isolated from the solid-substrate fermentation culture of Penicillium ochrochloronthe associated the roots of Taxus media. Compounds 1–4 displayed the antimicrobial activity selectively against tested fungal and bacterial strains with minimum inhibitory concentration (MIC) values ranging from 12.5 to 100 μg/ml. Furthermore, we found that only compound 4 exhibited moderate cytotoxicity against five human cancer cells (A549, LN229, MGC, LOVO, and MDA231) with IC₅₀ values of 51.45, 23.43, 39.16, 46.97, and 42.85 μg/ml, respectively.     

Phenylpropanoids from the leaves of Acanthopanax koreanum and their antioxidant activity

By various chromatographic methods, one new phenylpropanoid, acanthopanic acid (1), and three known compounds, 1,2-O-dicaffeoylcyclopenta-3-ol (2), (4S)-α-terpineol 8-O-β-D-glucopyranoside (3), and rutin (4), were isolated from the methanol extract of the Acanthopanax koreanum leaves. Their structures were elucidated on the basis of spectroscopic analyses, and their antioxidant activities were evaluated by the intracellular reactive oxygen species (ROS) radical scavenging 2′,7′-dichlorofluorescein diacetate assay. Among them, compounds 1, 2, and 4 showed significant scavenging capacity with IC₅₀ values of 3.8, 2.6, and 2.9 μM, respectively, and compound 3 showed weak scavenging capacity with the inhibition rate of 37% at 40 μM.     

Three new flavanoids from artificially induced dragon’s blood of Dracaena cambodiana

Three new flavanoids, (2R)-7,4′-dihydroxy-8-methylflavan (1), (2R)-7,4′-dihydroxy-6-methylflavan (2), and (3R)-7,3′,4′-trihydroxyhomoisoflavan (3), together with seven known compounds (4–10), were isolated from artificially induced dragon’s blood of Dracaena cambodiana, and their structures were determined based on HR-ESI-MS and extensive spectroscopic techniques (UV, IR, 1D-, and 2D-NMR). Compound 2 exhibited weak cytotoxicity against BEL-7402 cells line with the IC₅₀ value of 39.2 μM. In addition, compound 3 showed significant acetylcholinesterase (AChE) inhibitory activity.     

Two new 8-O-4′-type lignans from the stem of Schima superba and their cell growth inhibitory activities against human cancer cell lines

Two new lignans (1 and 2) were isolated from the EtOH extracts of the stem of Schima superba, and elucidated as (7R,8S)-1-(3,4-dimethoxyphenyl)-2-O-(2-methoxy-4-omegahydroxypropylphenyl)propane-1,3-diol (1) and threo-1-(4-hydroxy-3-methoxyphenyl)-1-methoxy-2-{4-[1-formyl-(E)-vinyl]-2-methoxyphenoxy}-3-propanol (2) by spectral analysis. Compounds 1 and 2 showed cell growth inhibitory activity against HeLa, CNE, HepG-2, and HEp-2 cell lines. Compound 1 exhibited significant cytotoxicities with IC₅₀ values of less than 4 μg/ml against all the tested cell lines.