Mixture Of Stigmasterol Research Articles

A New Aromatic Amide from the Roots of Zanthoxylum tessmannii (Rutaceae).

Phytochemical investigation of the methanolic extract of the roots of Zanthoxylum tessmannii Zepernick and Timler (Rutaceae) led to the isolation and characterization of one new aromatic amide named tessmamide (1) along with twelve known compounds, N-benzoyltyramine methyl ether (2), 7,8,9-trimethoxycoumarin (3), 7,8-dimethoxycoumarin (4), integrifoliodiol (5), robustin (6), skimmianine (7), lupeol (8), lupenone (9), a mixture of stigmasterol and β-sitosterol, and a mixture of their glucosides. The structures of all compounds were determined by comprehensive spectroscopic analyses (1D- and 2D-NMR, EI-MS, and ESI-MS) and comparison with known analogs. The determination of the radical scavenging activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay gave moderate antioxidant values for the crude extracts of the roots of Zanthoxylum tessmannii (IC50 0.8 mg/mL), tessmamide (1; IC50 31.8 μm), and 7,8,9-trimethoxycoumarin (3; IC50 29.3 μm), compared to the standard ascorbic acid (IC50 11.6 μm).

Isolation and antimicrobial activities of a novel discolornolide and other compounds from Monanthotaxis discolor

Characterisation of a novel discolornolide (1) isolated from a first time investigation of Monanthotaxis discolor is described. Other 6 known compounds, karatavin (2), N-acetylanonaine (3), quercetin-3-O–arabinose (4), stigmasterol (5), a mixture of stigmasterol and β-sitosterol (6) and octahydro-5-isopropyl-3-methyl-2-methyleneazulene-8,8-diol (7) isolated are also reported. The structures were established by spectroscopic methods. Citotoxicities and antimicrobial activities of the compounds and crude extracts are also reported whereby compound 1 showed in vitro antifungal activity against Candida albicans and Aspergilus niger at concentrations of 0.13 and 0.17 mg/ml with zones of inhibitions of 7.0 and 5.5 mm respectively. The compound also showed cyitotoxic activity in the brine shrimp test with LC50 of 5.88 μg/ml. - Compound 4 exhibited antibacterial activity against E. coli and S. aureus. The compound also exhibited cytotoxic activities in the brine shrimp test with LC50 of 24.73 μg/mL. The crude extracts exhibited varying citotoxic and in vitro antimicrobial activities.

Triterpenoidal and Phenolic Compounds Isolated from the Aerial Parts of Helicteres hirsuta and their Cytotoxicity on Several Cancer Cell Lines

Helicteres L. is one of the genera of the Sterculiaceae family with several remarkable activities. Previous studies revealed that terpenoids, flavonoids, and lignans are the dominant constituents of Helicteres species. However, information about this genus is scarce and unsystematic. Most of the phytochemical and pharmacological investigations have been mainly reported on Helicteres angustifolia and Helicteres isora, which are commonly used in China and Indonesia, respectively. In the present study, two terpenoids: 3β- O-acetylbetulinic acid (1) and simiarenol (2) together with three phenolic compounds: 4,4'-sulfinylbis(2-( tert-butyl)-5-methylphenol) (3), 7- O-methylisoscutellarein (4), 7,4'-di- O-methylisoscutellarein (5), and a mixture of stigmasterol and β-sitosterol were isolated and structurally elucidated from the aerial parts of Helicteres hirsuta Lour. Compounds 1-5 were tested for cytotoxicity on four human cancer cell lines: leukemia CCRF-CEM, breast MDA-MB-231, colon HCT116 and glioblastoma U251 cancer cells. Among them, compounds 1 and 3 showed moderate activity on CCRF-CEM and HCT116 cancer cells with IC50 values ranging from 14.6 to 31.5 μM (P < 0.05). This is the first time these compounds have been reported from this plant. To the best of our knowledge, compound 3 is novel in nature although it has been chemically synthesized before, and compounds 1, 2, and 4 are new to this plant family (Sterculiaceae).

Therapeutic Protection from Hepatic Injury and Chemical Constituents of Buchanania angustifolia Roxb

The use of modern medicines in the treatment of diseases instead of traditional medicine is causing different adverse effects. Therefore, there is need to search new bioactive compounds to treat different diseases. Buchanania angustifolia has been used in traditional medicine in the treatment of different diseases. On the basis of folkloric information, B. angustifolia aerial parts extracts have been selected for their antioxidant and hepatoprotective potentiality and phytochemical constituents. Qualitative phytochemical screening of B. angustifolia extracts revealed the presence of phytochemical constituents such as steroids, terpenoids, flavonoids, alkaloids, glycosides, tannins, carbohydrates, oils and amino acids. BA-1 and BA-2 compounds isolated from hydroalcoholic extract using chromatography and were identified as linolenic acid and mixture of stigmasterol and β-sitosterol. Antioxidant activity was performed on superoxide, hydroxyl and 1-(2,6-dimethylphenoxy)-2-(3,4-dimethoxyphenylethylamino) propane hydrochloride free radicals. The B. angustifolia extracts showed dose-dependent activity on free radicals. The hydroalcoholic extract showed better activity. The extracts showed hepatoprotective activity on thioacetamide-induced liver intoxication in rats, and hydroalcoholic extract exhibited significant restoration of the altered biochemical parameters due thioacetamide-induced liver intoxication. Among the tested extracts of B. angustifolia, hydroalcoholic extract showed higher antioxidant and hepatoprotective activity and stigmasterol and β-sitosterol were isolated. Further research is needed to evaluate other pharmacological activities and to isolate the other bioactive compounds from B. angustifolia.

NEW DEGRADED QUINONE DITERPENOID FROM THE STEMS OF Byrsonima coccolobifolia Kunth. (Malpighiaceae)

A chemical investigation of two specimens of Byrsonima coccolobifolia collected in the southeast cerrado and from central Brazil was performed. A new degraded diterpenoid, byrsonimaquinone, was isolated from the stems along with known compounds. This is the first study on the roots of B. coccolobifolia, and several triterpenes, such as α-amyrin, β-amyrin, oleanolic acid, and glochidonol, along with a mixture of stigmasterol, β-sitosterol and campesterol, were identified. These compounds were identified by spectroscopic analysis techniques, including 1D and 2D NMR, GC-MS and high-resolution mass spectrometry.

Antimicrobial compounds from Alpinia conchigera

Ethnopharmacological relevanceThe rhizome of Alpinia conchigerahas been used as a condiment in the northern states of Peninsular Malaysia and occasionally in folk medicine in the east coast to treat fungal infections. In some states of Peninsular Malaysia, the rhizomes are consumed as a post-partum medicine and the young shoots are prepared into a vegetable dish. This study aimed to investigate the chemical constituents of the pseudostems and rhizomes of Malaysian Alpinia conchigera and to evaluate the antimicrobial activity of the dichloromethane (DCM) extracts of the pseudostems, rhizomes and the isolated compounds against three selected fungi and five strains of Staphylococcus aureus. Materials and methodsThe dried and ground pseudostems (0.8kg) and rhizomes (1.0kg) were successively extracted in Soxhlet extractor using n-hexane, dichloromethane (DCM) and methanol. The n-hexane and DCM extracts of the pseudostem and rhizome were subjected to isolation and purification using column chromatography on silica gel using a stepwise gradient system (n-hexane to methanol). Briefly, a serial two fold dilutions of the test materials dissolved in DMSO were prepared prior to addition of 100μl overnight microbial suspension (108 cfu/ml) followed by incubation at 37°C (bacteria) or 26°C (dermatophytes and candida) for 24h. The highest concentration of DMSO remaining after dilution (5%, v/v) caused no inhibition to bacterial/candida/dermatophytes’ growth. Antibiotic cycloheximide was used as reference for anticandidal and antidermatophyte comparison while oxacilin was used as reference for antibacterial testing. DMSO served as negative control. Turbidity was taken as indication of growth, thus the lowest concentration which remains clear after macroscopic evaluation was taken as the minimum inhibitory concentration (MIC). ResultsThe isolation of n-hexane and DCM extracts of the rhizomes and pseudostems of Alpinia conchigera via column chromatography yielded two triterpenes isolated as a mixture of stigmasterol and β-sitosterol: caryophyllene oxide, chavicol acetate 1, p-hydroxy cinnamaldehyde 2, 1′S-1′-acetoxychavicol acetate 3, trans-p-coumaryl diacetate 4, 1′S-1′-acetoxyeugenol acetate 5, 1′-hydroxychavicol acetate 6, p-hydroxycinnamyl acetate 7 and 4-hydroxybenzaldehyde.The DCM extract of the rhizome of Alpinia conchigera indicated potent antifungal activity against Candida albicans, Microsporum canis and Trycophyton rubrum with MIC values of 625μg/ml, 156μg/ml and 156μg/ml, respectively. It also showed significant inhibitory activity with MIC values between 17.88 and 35.75μg/ml against the mutant Staphylococci isolates MSSA, MRSA and Sa7.Amongst the isolated compounds, the lowest inhibition observed were of 1′S-1′-acetoxyeugenol against the dermatophytes (MIC 313μg/ml) followed by trans-p-coumaryl diacetate against both dermatophytes and candida (MIC 625μg/ml). The compound p-hydroxycinnamyl acetate strongly inhibited Staphylococcusaureus strain VISA (MIC 39μg/ml) followed by trans-p-coumaryl diacetate and 1′-hydroxychavicol acetate with MIC value of 156μg/ml. ConclusionIn conclusion, the observed antibacterial, anticandidal and antidermatophyte activity of the extracts and compounds obtained from the rhizome confirm the traditional use of Alpinia cochigera rhizome in the treatment of skin infection.

Naucleactonin D, an Indole Alkaloid and other Chemical Constituents from Roots and Fruits of Mitragyna inermis

Phytochemical investigation of the roots and fruits of Mitragyna inermis (Rubiaceae) resulted in the isolation of a new indole alkaloid, named naucleactonin D (1), together with fourteen known compounds: nauclefiline (2), naucleficine (3), nauclefidine (4), angustoline (5), angustine (6), barbinervic acid (7), quinovic acid 3-O-a-L-rhamnopyranoside (8), betulinic acid (9), a mixture of ursolic (10) and oleanolic acid (11), a mixture of stigmasterol and b-sitosterol, b-sitosterol 3-O- b-D-glucopyranoside, and strictosamide (12) as the major compound. The structures of the isolated compounds were elucidated by detailed spectroscopic analysis and by comparison with published data. No 13C NMR data for 2 and 3 exist in the literature and compounds 2, 3, 5, 7, and 12 are reported for the first time from the genus Mitragyna. The crude extract and isolated compounds were tested in vitro for their preliminary cytotoxicity against brine shrimps (Artemia salina).

Chemical profile and biological activities of Deguelia duckeana A.M.G. Azevedo (Fabaceae)

Deguelia duckeana is popularly known as timbó and used by indigenous people as ictiotoxic. On account of there being no literature pertaining to the chemical profile or biological activity of this plant, the hexane, methanol and aqueous crude extracts from leaves, stems and roots were assayed that presented very high cytotoxic potential against Artemia salina, achieving 100% mortality in up to 5.0 µg mL−1 concentration, but lower antioxidant potential on 2,2-diphenyl-1-picryl-hydrazyl and Fe3+/Phenanthroline assays. The phytochemical analysis of crude extracts showed the presence of flavonoids and related compounds as major constituents as well as steroids in all of them, and tannins in polar extracts. All the extracts were assayed for antibacterial activity but only the hexane extract of stems showed moderate activity on Staphylococcus aureus, which was fractionated and yielded a mixture of 3,5,4′-trimethoxy-4-prenylstilbene, lonchocarpine, 4-hydroxylonchocarpine and derricidine, reported for the first time in D. duckeana and other fraction with β-sitosterol and stigmasterol mixture.

Chemical constituents of Millettia barteri and their antimicrobial and antioxidant activities

Context: Millettia barteri (Benth.) Dunn (Fabaceae) is an African medicinal plant used in folk medicine to treat many diseases. This species, as well as other Mellettia species, has been of interest to researchers because of their wide range of traditional uses.Objective: Phytochemical, antimicrobial and 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH)-radical scavenging investigations of the hexane and EtOAc extracts of the stem bark of M. barteri were carried out here for the first time.Materials and methods: The isolation of compounds was done through silica gel column chromatography and their structures were established using spectroscopic analysis, especially, 1D NMR in conjunction with 2D experiments (COSY, HMQC and HMBC), and physical data compared with literature values. The broth micro dilution method was used for antimicrobial test while DPPH radical scavenging assay was used for antioxidant test.Results: Seven compounds, including two guanidine alkaloids: millaurine (2) and milletonine (7); one flavonoid: afzelin (6); four sterols: β-sitosterol (1), β-sitosterol glucoside (3), mixture of stigmasterol (4) and β-sitosterol (5) palmitates have been isolated from stem bark of hexane and ethyl acetate extracts of M. barteri. These extracts showed antimicrobial activity on the set of germs tested with minimum inhibitory concentration values varying from 64 to 512 µg/mL, as well as antioxidant activity (IC50 62.74 and 77.23 µg/mL). Compounds 2 and 7, tested for the first time, demonstrated antimicrobial and antioxidant activities.Discussion and conclusions: The present study clearly demonstrated that M. barteri and some of its isolates possess antimicrobial and antioxidant properties and may act as potential antioxidant for biological systems susceptible to free radical-mediated reactions.

Estudo fitoquímico e avaliação da atividade anti-inflamatória de Aeschynomene fluminensis vell. (Fabaceae)

Phytochemical investigation of Aeschynomene fluminensis leaves and branches led to isolation of the flavonoid glycosides kaempferol 3,7-di-O-α-L-rhamnopyranoside, kaempferol 7-O-α-L-rhamnopyranoside, kaempferol 3-O-apiofuranosil-7-O- rhamnopyranoside, quercitin 3-O-α-L-rhamnopyranoside, quercitin 3-O-arabinofuranoside, 8-β-D-glucopyranosyl 4',5,7-trihydroxyflavanone, the isoflavonoid 4',7-di-hydroxy-isoflavone, the dimer epicatechin-(2β→7, 4β→8)- epicatechin, the polyol 3-O-methyl-chiro-inositol and two steroids in sitosterol and stigmasterol mixture. These compounds were identified by NMR 1H and 13C and compared with literature data. Anti-inflammatory activity of the crude methanolic extract and its fractions was evaluated.

Bioactive Constituents from the Twigs of Sonneratia alba

Three pentacyclic triterpenoids: lupeol [1], oleanolic acid [2], and betulinic acid [3] were isolated from the twigs of Sonneratia alba together with 2,6-dimethoxy-p-benzoquinone [4], a mixture of stigmasterol [5] and b-sitosterol [6]. Their structures were elucidated by analyses of their 1D and 2D NMR, and their physical and spectral data were compared with those reported in the literature. Amongst these isolates, compounds [2,3] exhibit antimycobacterial activity with MIC values of 25 and 50 mg/ml respectively. In addition, compound [4] exhibited antimalarial activity against P. falciparum with an IC50 value of 3.08 mg/ml.

동부로부터 sterol의 분리 동정

The seed of cowpea (Vigna sinensis K.) was extracted with 80% aqueous methanol (MeOH). And the concentrated extract was partitioned with ethyl acetate (EtOAc), n-butanol (n-BuOH) and , successively. The repeated silica gel and octadecyl silica gel (ODS) column chromatographic separations for the EtOAc and n-BuOH fractions led to isolation of four sterols. And the chemical structures of the compounds were determined as a mixture of stigmasterol and -sitosterol with the ratio of 4 to 3 (1), 7-ketositosterol (2), and stigmasterol 3-O-D-glucopyranoside (3) from the interpretation of spectroscopic data including nuclear magnetic resonance (NMR) spectrum metric, mass (MS) spectrum metric and infrared (IR) spectroscope. This study reports the first isolation of -sitosterol, 7-ketositosterol, and stigmasterol 3-O--D-glucopyranoside from the seed of Vigna sinensis K. In addition, compound 2, 7-ketositosterol, is rarely occurred in natural source including plant.

Chemopreventive Properties of Phytosterols and Maslinic Acid Extracted from Coleus tuberosus in Inhibiting the Expression of EBV Early‐Antigen in Raji Cells

Bioassay-guided fractionation of a MeOH extract of tubers of Coleus tuberosus afforded the active anti-tumor-promoting compounds identified as the triterpenoid 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (maslinic acid; CT2) and a phytosterol mixture (CT1). CT1 consists of stigmasterol (32%), beta-sitosterol (40.3%), and campesterol (27.7%) as determined by capillary gas chromatography. CT1 and CT2 showed very strong anti-tumor-promoting activities at IC(50) 0.7 microg/ml and 0.1 microg/ml, respectively, in a convenient, short-term in vitro assay, i.e., the inhibition of Epstein-Barr virus (EBV) activation induced by phorbol 12-myristate 13-acetate (PMA) and sodium butyrate. We report for the first time the anti-tumor-promoting activity of 2alpha,3beta-dihydroxyolean-12-en-28-oic acid and show that a mixture of stigmasterol, beta-sitosterol, and campesterol is more potent than the individual components in inhibiting tumor-promoting activity.

Free radical scavenging and anti-edematogenic activities of Paullinia elegans Cambess., Sapindaceae, leaves extracts

Ethanol extract of the leaves of Paullinia elegans Cambess., Sapindaceae, and its hexane, chloroform, ethyl acetate, and hydroethanol fractions were evaluated for their antiedematogenic and free radical scavenging activities. The ethanol extract and the hexane fraction produced statistically significant inhibition (74.4 and 76.0%, respectively) of the ear edema induced by croton oil in mice, observed at doses of 5 mg/ear. The ethyl acetate and hydroethanol fractions showed significant radical scavenging effect in the DPPH assay, with IC50 of 36.7 and 30.1 µg/mL, respectively. Fractionation of the extracts through chromatographic methods afforded epifriedelanol, oleanolic acid 3-O-acetyl, a mixture of stigmasterol 3-β-O-glucopyranoside and sitosterol 3-β-O-glucopyranoside, kaempferol 3,7-O-α-dirhamnopyranoside, kaempeferol-3-O-α-rhamnopyranoside and 2-O-methyl-chiro-inositol. The compounds were identified on the basis of their NMR spectral data and comparison with those of literature.

Caldensinic acid, a benzoic acid derivative and others compounds from Piper carniconnectivum

A benzoic acid derivative - caldensinic acid; E-phytyl hexadecanoate; β-sitosterol and stigmasterol mixture and phaeophytin a were isolated from the aerial parts of Piper carniconnectivum. The structures of these compounds were established unambiguously by IR, MS, 1D and 2D NMR analysis.

Steroidal and phenolic compounds from Sidastrum paniculatum (L.) Fryxell and evaluation of cytotoxic and anti-inflammatory activities

Sidastrum paniculatum (L.) Fryxell belongs to the family Malvaceae and is popularly known as malva roxa or malvavisco. The phytochemical study of the hexane, CHCl3 and EtOAc phases from the crude ethanol extract of S. paniculatum led to the isolation of six compounds: a mixture of β-sitosterol and stigmasterol, 4-methoxy-3-hydroxybenzoic acid, 4-methoxy-3-hydroxybenzaldehyde, N-trans-feruloyltyramine and kaempferol-3-O-β-D-(6''-E-p -coumaroyl) glucoside. The structural identification of the compounds was made on the basis of spectroscopic methods such as IR, 1H and 13C NMR with the aid of including two-dimensional techniques, besides comparison with literature data. The β-sitosterol and stigmasterol mixture showed a significant anti-inflammatory activity.

Fungicidal activity of compounds extracted from the pericarp of Areca catechu against Colletotrichum gloeosporioides in vitro and in mango fruit

Areca catechu L., a member of the Palmaceae family, is one of the most commonly used drugs in the world. Compounds obtained from the hexane, ethyl acetate and methanol extracts of the pericarp of A. catechu L. were assessed in vitro and in mango fruit for antifungal activity against Colletotrichum gloeosporioides Penz. In vitro studies also indicated that three triterpenes, namely fernenol (fern-9(11)-en-3α-ol), arundoin (fern-9(11)-en-3α-ol ME), and a mixture of stigmasterol and β-sitosterol, and one fatty acid, lauric acid, could inhibit the mycelial growth of C. gloeosporioides with EC 50 values of 36.7, 47.5, 56.7 and 111.5 mg L −1, respectively. Furthermore, fernenol, arundoin, and the mixture of stigmasterol and β-sitosterol highly inhibited spore germination and germtube elongation. Mango fruit studies suggested that fernenol, arundoin and the mixture of stigmasterol and β-sitosterol were significantly more effective than benomyl for controlling postharvest anthracnose disease when used at 100 and 200 mg L −1.

Triumfettamide and Triumfettoside Ic, Two Ceramides and Other Secondary Metabolites from the Stems of WildTriumfetta cordifoliaA. Rich. (Tiliaceae)

AbstractTwo new ceramides, triumfettamide (1) and triumfettoside Ic (2), characterized as (2R,6Z)‐2‐hydroxy‐N‐[(2S,3S,4R)‐1,3,4‐trihydroxyhexacosan‐2‐yl]heptadec‐6‐enamide and (2R)‐N‐{(1S,2R,3E,6Z, 9Z,12Z,15Z)‐1‐[(β‐D‐glucopyranosyloxy)methyl]‐2‐hydroxyheneicosa‐3,6,9,12,15‐pentaen‐1‐yl}‐2‐hydroxytetradecanamide, respectively, were isolated from the stems ofTriumfetta cordifoliaA. Rich.besides eight known secondary metabolites identified as heptadecanoic acid,β‐sitosterol glucopyranoside, friedelin, lupeol, betulin, maslinic acid, 2‐hydroxyoleanolic acid and the mixture of stigmasterol andβ‐sitosterol. Their structures were determined on the basis of spectroscopic methods as well as HR‐MALDI‐FT‐ICR‐MS analysis, chemical transformation, and by comparison of their physical and spectral data with those reported in the literature and with authentic specimens for some known compounds. Five pentacyclic triterpenoids, friedelin, lupeol, betulin, maslinic acid, and 2‐hydroxyoleanolic acid, have been isolated fromTriumfettagenus for the first time.

Constituintes químicos de licania tomentosa Benth. (Chrysobalanaceae)

CHEMICAL CONSTITUENTS OF Licania tomentosa BENTH. (CRHYSOBALANACEAE). This paper describes the chemical constituents isolated from leaves and fruits of Licania tomentosa Benth. The plant materials were successively extracted with hexane and methanol. From the extracts the following compounds were obtained: betulinic acid; licanolide, a new triterpene lactone; oleanolic acid, lupeol; palmitoleic and hexadecanoic acid; a mixture of stigmasterol and sitosterol; and a mixture of tormentic, ursolic and betulinic acid. The structures of the natural products were identified on the basis of spectral data.

.ALPHA.-Glucosidase Inhibitors from Garcinia brevipedicellata (Clusiaceae)

In our continuous search for alpha-glucosidase inhibitors from plants, four new depsidones named brevipsidones A-D (1-4) were isolated from stem bark of Garcinia brevipedicellata together with known damnacanthal, scopoletin and a mixture of stigmasterol and beta-sitosterol. Structural elucidations were made by spectroscopic analyses including 2D-NMR data.