Antimicrobial, Antioxidant, and Antityrosinase Activities of Morina persica L. and Its Isolated Compounds.

In this study, the isolation of compounds from the aerial parts of Morina persica L. and the antimicrobial, antioxidant and antityrosinase activities of various polarity extracts and isolated compounds were investigated. Column chromatography methods were used for isolation. A microdilution method was used to determine antimicrobial activity; Folin-Ciocalteu method was used to determine total phenolic content; DPPH and ABTS radical scavenging- capacity methods were used to determine antioxidant activity; and a mushroom tyrosinase method was used to determine antityrosinase activity. Kaempferol-3-O-ß-glucopyranoside (astragalin) and quercetin-3-O-rutinoside (rutin) were isolated from M. persica. The extracts and compounds showed higher activity against Staphylococcus aureus and Enterococcus faecalis than other tested bacteria. The highest phenolic content, DPPH, and ABTS radical scavenging activity were detected in an ethyl acetate extract at 50 µg/mL concentration. The methanol extract showed the highest antityrosinase effect at 200 µg/mL concentration.

Evaluation of cytotoxic and apoptotic effects of the extracts and phenolic compounds of Astragalus globosus Vahl and Astragalus breviflorus DC.

Astragalus L. is a genus member of the Fabaceae family, representing about 3,000 species all over the world and 380 species in Turkey. Astragalus species have been used in traditional medicine for many years. Astragalus globosus Vahl, known as "top geven", is a dwarf, scapose, perennial herb, Astragalus breviflorus DC., known as "yünlü geven", is an extremely spiny dwarf shrub. These endemic species grow in the Turkish cities of Erzurum, Kars, and Van. This is the first phytochemical and cytotoxic investigation of Astragalus globosus Vahl and Astragalus breviflorus DC. The main extracts and sub-fractions from the plants were evaluated for in vitro cytotoxic and apoptotic activities. The IC50 values of dichloromethane, n-butanol, and water extracts of the aerial parts of A. globosus against the MCF-7 cell line were determined as 28.39, 868.60, and 1753.00 µg/mL. The values for the MDA-MB-231 cell line were 264.00, 620.30, and 1300.50 µg/mL, respectively. From A. globosus, the following were isolated: a flavone glycoside, diosmetin-7-O-rutinoside (1); and two flavonol glycosides, isorhamnetin-3-O-rutinoside (2) and quercetin-3-O-galactoside (3). From A. breviflorus, two phenolic acids, caffeic acid (4) and chlorogenic acid (5), and a flavan-3-ol, catechin (6), were isolated. Diosmetin-7-O-rutinoside was isolated from Astragalus species for the first time and showed the highest cytotoxic activities on the MCF-7 and MDA-MB-231 breast cancer cell lines with IC50 values of 13.65 and 12.89 µg/mL, respectively. Moreover, we observed that diosmin exerts cytotoxic effects by causing cell necrosis.

Lavandula stoechas L. subsp. stoechas, a New Herbal Source for Ursolic Acid: Quantitative Analysis, Purification and Bioactivity Studies.

In this study, methanol, ethanol, methanol-dichloromethane (1 : 1, v/v), acetone, ethyl acetate, diethyl ether, and chloroform extracts of lavender (Lavandula stoechas L. subsp. stoechas) were prepared by maceration, and the ursolic acid contents in the extracts were determined quantitatively by HPLC analyses. The present results show that the methanol-dichloromethane (1 : 1, v/v) solvent system is the most efficient solvent system for the extraction of ursolic acid from the plant sample with the highest yield (2.22 g/100 g plant sample). In the present study, a new practical method for the isolation of ursolic acid from polar extracts was also demonstrated for the first time. The inhibition effects of the extracts and ursolic acid were also revealed on α-glycosidase, acetylcholinesterase, butyrylcholinesterase, and human carbonic anhydrase I and II enzymes by determining IC50 values for the first time. The extracts and ursolic acid acted as potent antidiabetic agents by strongly inhibiting the α-glycosidase activity, whereas they were found to be very weak neuroprotective agents. In view of the present results, L. stoechas and its major metabolite, ursolic acid, can be recommended as a herbal source to control postprandial blood sugar levels and prevent diabetes by delaying the digestion of starch in food.

Bromination of endo-7-norbornene derivatives revisited: failure of a computational NMR method in elucidating the configuration of an organic structure.

Previously we reported on the bromination of endo-7-bromonorbornene at different temperatures yielding mixtures of addition products. The structural elucidations of the formed compounds were achieved by NMR spectroscopy. Particularly, the γ-gauche effect and long-range couplings were instrumental in assigning the stereochemistry of the adducts. However, in a recent paper, Novitskiy and Kutateladze claimed that based on an applied machine learning-augmented DFT method for computational NMR that the structure of the product, (1R,2R,3S,4S,7s)-2,3,7-tribromobicyclo[2.2.1]heptane was wrong. With the aid of their computational method, they revised a number of published structures, including ours, and assigned our product the structure (1R,2S,3R,4S,7r)-2,3,7-tribromobicyclo[2.2.1]heptane. To fit their revised structure, they proposed an alternative mechanism featuring a skeletal rearrangement without the intermediacy of a carbocation. Herein, we are not only confirming the structure originally assigned by us through crucial NMR experiments, we also present the ultimate structural proof by means of X-ray crystallography. Moreover, we disprove the mechanism proposed by the aforementioned authors based on sound mechanistic reasoning and point to an oversight by the authors that led them to an erroneous mechanistic pathway.

Isolation of Major Compounds and Gastroprotective Activity of Alchemilla Caucasica on Indomethacin Induced Gastric Ulcers in Rats.

OBJECTIVE: The Alchemilla genus, which belongs to the Rosaceae family, is known as Lady's mantle and is commonly used in traditional medicine. This study was designed to investigate the major metabolites isolation and gastroprotective effects of Alchemilla caucasica. MATERIALS AND METHODS: Phytochemical studies were carried out using column chromatography on Alchemilla caucasica. The gastroprotective effect of ethanol extract of this plant was tested on indomethacin-induced gastric ulcer model in rats. In addition, superoxide dismutase (SOD), malondialdehyde (MDA), and glutathione (GSH) parameters in the stomach tissue were examined. RESULTS: Quercetin-3-O-glucuronide, apigenin, and catechin were isolated from aerial parts of Alchemilla caucasica. When macroscopic ulcer index and histopathological results were analyzed, the extract at 200 mg/kg dose was found to be most effective. All doses of extract reduced MDA level and enhanced SOD activity and GSH level. CONCLUSION: The results of this study showed that Alchemilla caucasica has significant antiulcer activity. This effect was thought to be caused by antioxidant properties of flavonoids.

Matrix metalloproteinase inhibitor and sunscreen effective compounds from Rumex crispus L.: isolation, identification, bioactivity and molecular docking study.

INTRODUCTION: Rumex (Polygonaceae) species are widely grown worldwide and their main compounds are anthranoids, tannins, naphthalenes and flavonoids. Matrix metalloproteinase (MMP) enzymes that cause the breakdown of the extracellular matrix and harmful ultraviolet (UV) rays are two important causes of skin ageing. Although there have been many studies on anthraquinones, there are not many studies on their anti-ageing effects. OBJECTIVE: The aim of this study was to determine the anti-ageing effects of pure compounds isolated from Rumex crispus L. by measuring their MMP inhibitory and sunscreen activities. METHODOLOGY: Molecular docking studies on anthranoid, flavonoid, tannin and naphthalene skeletons with MMP enzymes were applied for the first time. Various chromatographic methods were used for isolation studies. The structure elucidation was performed by spectroscopic [UV, infrared (IR), electrospray ionisation mass spectrometry (ESI-MS), nuclear magnetic resonance (NMR)] methods. To determine the anti-ageing capacity of compounds, MMP-1, MMP-8, MMP-13 enzyme inhibitory effects and sun protection factors (SPFs) were investigated for the first time. RESULTS: Molecular docking results showed that skeletons had low binding energy to the target and were likely to inhibit MMP enzymes. Then, eight anthraquinones and a naphthalene glycoside were isolated from the underground parts of Rumex crispus L. According to the results, MMP inhibitory effects of compounds were found to be high. In vitro and molecular docking study results confirmed each other. All anthraquinones showed high sun protection and emodin showed highest UV capability with SPF of 30.59. CONCLUSION: This study shows that anthraquinones may be evaluated as new potential MMP inhibitors, sun protective and anti-ageing agents.

human monoamine oxidase (hMAO) A and hMAO B inhibitors from Artemisia dracunculus L. herniarin and skimmin: human mononamine oxidase A and B inhibitors from A. dracunculus L.

The aim of this study was to investigate the effects of extracts and pure Artemisia dracunculus L. (tarragon) metabolites on the antimonoamine oxidase and anticholinesterase activities. The compounds were characterized as stigmasterol (1), herniarin (2), (2E,4E)-1-(piperidin-1-yl)undeca-2,4-diene-8,10-diyn-1-one (3), (2E,4E)-N-isobutylundeca-2,4-dien-8,10-diynamide (4), 3,4-dehydroherniarin (5) and skimmin (6) by 1H-NMR, 13C-NMR, 1D and 2D NMR methods. The compounds 5 and 6 were isolated from tarragon for the first time. The extracts and pure compounds have inhibitory effects on the human monoamine oxidase (hMAO) A and B enzymes, whereas they did not exhibit any anticholinesterase activities. Among the tarragon compounds, only 2 and 6 compounds showed the inhibitory effects against hMAO A (IC50 = 51.76 and 73.47 µM, respectively) and hMAO B (IC50 = 0.84 and 1.63 mM, respectively). In the study, herniarin content in the extracts was also analysed by high-performance liquid chromatography and it was found that there was a relationship between the inhibition effects of the extracts and their herniarin content.

Synthesis and antioxidant activities of phenol derivatives from 1,6-bis(dimethoxyphenyl)hexane-1,6-dione.

Starting from the compound (3,4-dimethoxyphenyl)(2-(3,4-dimethoxyphenyl)cyclopent-1-en-1-yl)methanone (4), two diols and three tetrol derivatives were synthesised. Morover, from the reactions of 1,3-dimethoxybenzene and 1,4-dimethoxybenzene with adipoyl chloride, fifteen new along with nine known compounds were obtained. For the characterizations of compounds, spectroscopic methods such as NMR including DEPT, COSY, HMQC and HMBC experiments and X-ray diffraction were used. The antioxidant activities of novel synthesized seventeen molecules were investigated by analytical methods like ABTS•+ and DPPH• scavenging. Also, reducing power these molecules were investigated by Fe3+, Cu2+, and [Fe3+-(TPTZ)2]3+. Some of the molecules record powerful antioxidant profile when compared to putative standards. The inhibition effects of the phenols compounds against AChE and BChE activities were analysed. Also, these phenols were found as effective inhibitors for AChE, hCA I, hCA II, and BChE with Kis in the range of 122.95 ± 18.41-351.31 ± 69.12 nM for hCA I, 62.35 ± 9.03-363.17 ± 180.1 nM for hCA II, 134.57 ± 3.99-457.43 ± 220.10 nM for AChE, and 27.06 ± 9.12-72.98 ± 9.53 nM for BChE, respectively.

Synthesis, structure elucidation, and in vitro pharmacological evaluation of novel polyfluoro substituted pyrazoline type sulfonamides as multi-target agents for inhibition of acetylcholinesterase and carbonic anhydrase I and II enzymes.

A novel series of 4-(3-(difluorophenyl)-5-(dimethoxyphenyl)-4,5-dihydropyrazol-1-yl)benzenesulfonamides 1-8 were designed since sulfonamide and pyrazoline pharmacophores draw great attention in novel drug design due to their wide range of bioactivities including acetylcholinesterase (AChE) and human carbonic anhydrase I and II (hCA I and hCA II) inhibitory potencies. Comprehensive structure elucidation of the compounds synthesized was carried out by 1H NMR, 13C NMR, 19F NMR, DEPT 90-135, 1H-1H COSY, 1H-13C HMQC, HMBC, and HRMS spectra. The chemical shifts and splitting patterns of the protons and carbons were affected by the fluorine atoms and exciting splitting patterns were also recorded for the fluorinated compounds. In vitro enzyme assays obviously showed that the novel compounds had a significant inhibitory profile against hCA I, hCA II and AChE enzymes at the nanomolar levels. Ki values were in the range of 3.30 ± 1.09-5.95 ± 2.26 nM for hCA I and 4.29 ± 0.91-7.14 ± 3.15 nM for hCA II, while Ki values for AChE were in the range of 3.28 ± 1.47-9.77 ± 1.86 nM. Many of thecompounds in this study can be considered as promising AChE and CA inhibitors.

Synthesis and bioactivities of 1-(4-hydroxyphenyl)-2-((heteroaryl)thio)ethanones as carbonic anhydrase I, II and acetylcholinesterase inhibitors.

The discovery of enzyme targeting inhibitors is a popular area of drug research. Biological activities of the compounds bearing phenol and heteroaryl groups make them popular groups in drug design targeting important enzymes such as acetylcholinesterase (AChE, E.C.3.1.1.7) and carbonic anhydrases (CAs, EC 4.2.1.1). 1-(4-hydroxyphenyl)- 2-((aryl)thio)ethanones as possible AChE and CAs inhibitors were synthesized, and their chemical structures were confirmed by IR, 1H NMR, 13C NMR, and HRMS. The compounds 2 and 4 were found potent AChE inhibitors with the Ki values of 22.13 ±1.96 nM and 23.71 ±2.95 nM, respectively, while the compounds 2 (Ki = 8.61 ±0.90 nM, on hCA I) and 1 (Ki = 8.76 ±0.84 nM, on hCA II) had considerable CAs inhibitory potency. The lead compounds may help the scientists for the rational designing of an innovative class of drug candidates targeting enzyme-based diseases.

Cytotoxic naphthoquinones from Arnebia densiflora (Nordm.) Ledeb and determining new apoptosis inducers.

In this study, phytochemical composition of Arnebia densiflora (AD) was determined and cytotoxic effects of the n-hexane extract and compounds isolated from this species on various cell lines were investigated. By means of serial chromatographic studies, 6 naphthoquinone derivatives were yielded, which are isovalerylalkannin, α-methyl-n-butyl alkannin, acetylalkannin, ß-acetoxy isovalerylalkannin, alkannin and a new compound: 4-hydroxy 4-methyl valeryl alkannin. Structures of the isolated compounds were elucidated using UV, IR, 1D-2D NMR, MS and CD methods. Cytotoxic effects of the extract and isolated alkannins were investigated on L929, HeLa, HEp-2 cells. AD and the isolated compounds demonstrated moderate to strong cytotoxic effects (IC50 range: 4.92-172.35 µg/ml). The results of DNA fragmentation and caspase-3 activity studies on HeLa cells exhibited that AD and the naphthoquinones isolated from it caused cytotoxicity through induction of apoptosis.[Formula: see text].

The α-amylase and α-glucosidase inhibitory activities of the dichloromethane extracts and constituents of Ferulago bracteata roots.

CONTEXT: Ferulago (Apiaceae) species have been used since ancient times for the treatment of intestinal worms, hemorrhoids, and as a tonic, digestive, aphrodisiac, or sedative, as well as in salads or as a spice due to their special odors. OBJECTIVES: This study reports the α-amylase and α-glucosidase inhibitory activities of dichloromethane extract and bioactive compounds isolated from Ferulago bracteata Boiss. & Hausskn. roots. MATERIALS AND METHODS: The isolated compounds obtained from dichloromethane extract of Ferulago bracteata roots through bioassay-guided fractionation and isolation process were evaluated for their in vitro α-amylase and α-glucosidase inhibitory activities at 5000-400 µg/mL concentrations. Compound structures were elucidated by detailed analyses (NMR and MS). RESULTS: A new coumarin, peucedanol-2'-benzoate (1), along with nine known ones, osthole (2), imperatorin (3), bergapten (4), prantschimgin (5), grandivitinol (6), suberosin (7), xanthotoxin (8), felamidin (9), umbelliferone (10), and a sterol mixture consisted of stigmasterol (11), ß-sitosterol (12) was isolated from the roots of F. bracteata. Felamidin and suberosin showed significant α-glucosidase inhibitory activity (IC50 0.42 and 0.89 mg/mL, respectively) when compared to the reference standard acarbose (IC50 4.95 mg/mL). However, none of the tested extracts were found to be active on α-amylase inhibition. DISCUSSION AND CONCLUSIONS: The present study demonstrated that among the compounds isolated from CH2Cl2 fraction of F. bracteata roots, coumarins were determined as the main chemical constituents of this fraction. This is the first report on isolation and characterization of the bioactive compounds from root extracts of F. bracteata and on their α-amylase and α-glucosidase inhibitory activities.

Synthesis and Cytotoxic Activities of Difluoro-Dimethoxy Chalcones.

BACKGROUND: Although anticancer chemotherapeutics are available in markets, side effects related to the drugs in clinical use lead to researchers to investigate new drug candidates which are more safe, potent and selective than others. Chalcones are popular with their anticancer activities with the several reported mechanisms including inhibition of angiogenesis, inhibition of tubulin polymerization, and induction of apoptosis etc. OBJECTIVE: This study was focused on to synthesize of 1-(2,4/2,6-difluorophenyl)-3-(2,3/2,4/2,5/3,4- dimethoxyphenyl)-2-propen-1-ones (1-8) and investigate their cytotoxic properties with possible mechanism of action. METHOD: The compounds were synthesized by Claisen-Schmidt condensation. The chemical structures were confirmed by 1H NMR, 13C NMR, DEPT, COSY, HMQC, HMBC, 19F NMR and HRMS. In vitro cytotoxic effects of the compounds against human tumour cell lines [gingival carcinoma (Ca9-22), oral squamous cell carcinoma (HSC-2)] and human normal oral cells [gingival fibroblasts (HGF), periodontal ligament fibroblasts (HPLF)] were evaluated via MTT test. RESULTS: All compounds had higher cytotoxicity than reference compound 5-Fluorouracil (5-FU). The compounds 3-7 had higher potency selectivity expression values (PSE) than 5-FU and PSE values of the compounds were over 100. All chalcone derivatives seem good candidates for further studies according to very remarkable and high PSE values. CONCLUSION: It was clearly demonstrated that compound 7 can induce early apoptosis at a concentration of 10 µM and dose-dependent late apoptosis starting at 10 µM. Compound 7 induced cleavage of the apoptosis marker PARP. The results indicate that new chalcones reported here can promote apoptosis in human tumour cell lines.

Synthesis and bioactivity studies of 1-aryl-3-(2-hydroxyethylthio)-1-propanones.

A series of Mannich bases having piperidine moiety were reacted with 2-mercaptoethanol, leading to 1-aryl-3-piperidine-4-yl-1-propanone hydrochlorides. The cytotoxicity and carbonic anhydrase inhibitory activities of these new compounds were evaluated. Among the compounds, only one derivative, nitro substituent bearing EU9, showed an effective cytotoxicity, although weak tumor specificity against human oral malignant versus nonmalignant cells. The compound induced apoptosis in HSC-2 oral squamous cell carcinoma cells, but not in human gingival fibroblast. Chemical modifications of this lead are thus necessary to further investigate it as a drug candidate and to obtain compounds with a better activity profile.

ß-Hydroxydihydrochalcone and flavonoid glycosides along with triterpene saponin and sesquiterpene from the herbs of Pimpinella rhodantha Boiss.

A new ß-hydroxydihydrochalcone glycoside named ziganin (1) and a new acylated flavonol glycoside named isorhamnetin-3-O-α-L-(2″,3″-di-O-trans-coumaroyl)-rhamnopyranoside) (2), along with two known flavonoid glycosides, a ß-hydroxydihydrochalcone glycoside, a hydroxybenzoic acid derivative, a trinorguaiane type sesquiterpenoid, a triterpenic saponin and a polyol were isolated from the herbs of Pimpinella rhodantha Boiss. Their structures were elucidated on the basis of spectroscopic analyses including 1D-and 2D-NMR, UV, IR, CD, ESI-MS, APCI-MS, HR-ESI-MS techniques. The isolated compounds were evaluated for their antioxidant capacity through the DPPH free-radical scavenging assay and ferrous ion-chelating power test.

Gastroprotective and Antioxidant Effects of Lobaria pulmonaria and Its Metabolite Rhizonyl Alcohol on Indomethacin-Induced Gastric Ulcer.

Two lichen metabolites, rhizonaldehyde (1) and rhizonyl alcohol (2), were isolated from the acetone extract of Lobaria pulmonaria by chromatographic methods, and their chemical structures were determined by UV/VIS, IR, and 1D- and 2D-NMR spectroscopic methods. The gastroprotective and in vivo antioxidant activities of extracts of L. pulmonaria and its metabolites, 1 and 2, were investigated in indomethacin-induced ulcer models in rats. The gastric lesions were significantly reduced by acetone, hexane, and CHCl3 extracts, with 75.3-41.5% inhibition. Rhizonyl alcohol (2) significantly reduced the gastric lesions with an inhibition rate of 84.6-42.8%, whereas rhizonaldehyde (1) significantly increased the gastric lesions. Antioxidant parameters and myeloperoxidase activities were also evaluated in the gastric tissues of the rats. Indomethacin caused oxidative stress, which resulted in lipid peroxidation in gastric tissues by decreasing the levels of the antioxidants as compared to healthy rat tissues. In contrast to indomethacin, all extracts and rhizonyl alcohol (2) caused a significant decrease in lipid peroxidation levels and an increase in antioxidant parameters, superoxide dismutase, glutathione peroxidase, and glutathione-S-transferase, and reduced glutathione in gastric tissues. The administration of rhizonyl alcohol (2) also resulted in a decrease in gastric myeloperoxidase activity increased by indomethacin. The gastroprotective effect of rhizonyl alcohol (2) can be attributed to its antioxidant properties and its suppressing effect on neutrophil infiltration into gastric tissues.

Phtytochemical Studies and Quantitative HPLC Analysis of Rosmarinic Acid and Luteolin 5-O-ß-D-Glucopyranoside on Thymus praecox subsp. grossheimii var. grossheimii.

Thymus praecox ssp. grossheimii (RONNIGER) JALAS var. grossheimii (Lamiaceae) is used as an herbal tea for cold, stomachache, cough, and infections in Turkey. There are no phytochemical studies on this species. We performed phytochemical studies and quantitative analysis of rosmarinic acid and luteolin 5-O-ß-D-glucopyranoside in the methanol extract of the plant. Several chromatographic methods were used for the isolation of major compounds. HPLC methods were applied for quantitative analysis of rosmarinic acid and luteolin 5-O-ß-D-glucopyranoside in the methanol extract. In this study, ursolic acid (1), oleanolic acid (2), methyl rosmarinate (3), ethyl rosmarinate (4), rosmarinic acid (5), luteolin 5-O-ß-D-glucopyranoside (6), and thymoquinol 2,5-O-ß-diglucopyranoside (7) were isolated from the aerial parts of the plant. The relative contents of rosmarinic acid and luteolin 5-O-ß-D-glucopyranoside in the extract were 15.2 and 57.8 mg/g of dry weight, respectively. Compounds isolated from this plant and the contents of rosmarinic acid and luteolin 5-O-ß-D-glucopyranoside provided reasonable evidence for the traditional usages of this plant.

Cytotoxic compounds from endemic Arnebia purpurea.

Phytochemical studies of the roots and aerial parts of endemic Arnebia purpurea S. Erik & H. Sumbul resulted in the isolation and characterization of four naphthoquinones [isovalerylalkannin (1), α-methyl-n-butanoyl alkannin (2), acetylalkannin (3), and alkannin (4)], a triterpene derivative [3-O-acetyl-oleanolic acid (5)], a steroid [ß-sitosterol (6)], three flavonoid glycosides [isorhamnetin-3-O-rutinoside (7), kaempferol-3-O-rutinoside (8), kaempferol 3-O-(5"-acetyl) apiofuranoside 7-O-rhamnopyranoside (9)] and a phenolic acid [rosmarinic acid (10)]. 3-O-Acetyl-oleanolic acid, isorhamnetin-3-O-rutinoside, kaempferol-3-O-mrutinoside, and kaempferol 3-O-(5"-acetyl) apiofuranoside 7-O-rhamnopyranoside are reported from an Arnebia species for the first time. Cytotoxic activities on L929 murine fibrosarcoma cell line of the isolated compounds were investigated using MTT assay. Naphthoquinones (1-4) showed intermediate cytotoxic activity in comparison with the standard, doxorubicin.

Insecticidal metabolites from the rhizomes of Veratrum album against adults of Colorado potato beetle, Leptinotarsa decemlineata.

The dried rhizomes of Veratrum album were individually extracted with CHCl3 , acetone, and NH4 OH/benzene to test the toxic effects against the Colorado potato beetle, Leptinotarsa decemlineata, which is an important agricultural pest. Fifteen compounds in various amounts were isolated from the extracts using column and thin-layer chromatography. The chemical structures of 14 compounds were characterized as octacosan-1-ol (1), ß-sitosterol (2), stearic acid (3), diosgenin (4), resveratrol (5), wittifuran X (6), oxyresveratrol (7), ß-sitosterol 3-O-ß-D-glucopyranoside (8), diosgenin 3-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyronoside (9), oxyresveratrol 3-O-ß-D-glucopyranoside (10), jervine (11), pseudojervine (13), 5,6-dihydro-1-hydroxyjervine (14), and saccharose (15) using UV, IR, MS, (1) H- and (13)C-NMR, and 2D-NMR spectroscopic methods. However, the chemical structure of 12, an oligosaccharide, has not fully been elucidated. Compounds 4, 6, 9, and 10 were isolated from V. album rhizomes for the first time in the current study. The toxic effects of three extracts (acetone, CHCl3 , and NH4 OH/benzene) and six metabolites, 2, 2+4, 5, 7, 8, and 11, were evaluated against the Colorado potato beetle. The assay revealed that all three extracts, and compounds 7, 8, and 11 exhibited potent toxic effects against this pest. This is the first report on the evaluation of the toxic effects of the extracts and secondary metabolites of V. album rhizomes against L. decemlineata. Based on these results, it can be concluded that the extracts can be used as natural insecticides.