Records of Natural Products Articles

Mushrooms are very important sources of drugs for modern medicine. Phyotherapeutic efficiency of terpenes from mushrooms has been proved. Lanostane type triterpenoids having potentials for cancer disease treatments are rich source of mushrooms. Therefore, the demand of isolation of bioactive compounds from the mushroom species has been increasing due to their medicinal importance. The paper reviewed isolation and biological activities such as antibacterial, anticancer, anticandidal, anticholinesterase, anti-compliment, antileishmanial, anti-inflammatory, anti-invasive, antimalarial, antioxidant, antitubercular, antitumor, antiviral, and cytotoxic activities of terpenoids from mushroom origin in the last two decades.

Leaves and fruits of Morus nigra L. (Moraceae) are used for the treatment of wounds especially mouth sore in Turkish traditional medicine. The present study was designed to investigate wound healing activity of M. nigra by using incision and excision wound models. Furthermore, anti-inflammatory activity was assessed by Whittle method. Lyophilized fruit extract (MNF) displayed significant wound healing activity, while aqueous leaf extract of M. nigra (MNL) did not. Through biological activity guided fractionation technique, MNF was subjected to successive solvent extraction. Among the subextracts obtained, n-butanol (MNF-n-BuOH) subextract was found to possess wound healing activity. MNF -n-BuOH was subjected Sephadex LH-20 column chromatography to obtain three fractions, which then applied to the same biological activity tests. Compounds 1 and 2 were isolated from the active fraction and their structures were identified as quercetin-3-O-rutinoside and kaempferol-3-O-rutinoside, respectively. The isolates were investigated for their in vitro enzyme inhibitory activities.

Cranberries (Vaccinium macrocarpon) contain many bioactive compounds and have some biological activities and beneficial health properties. In the study, antioxidant effects of lyophilized aqueous extract of cranberry (LAEC) and quantity of some its polyphenolic compounds were determined. For this purpose, we performed DPPH·, DMPD •+, ABTS •+ and O 2 •- radicals scavenging activities, inhibition of lipid peroxidation activity by thiocyanate method, Cu 2+ and Fe 3+ reducing abilities, FRAP assay and Fe 2+ binding activity. At the 10 µg/mL concentration, LAEC inhibited 52.4% lipid peroxidation produced by linoleic acid emulsion. Also, α-tocopherol, BHA, trolox, and BHT had 52.5, 89.9, 93.1 and 94.9% inhibition value at 30 µg/mL concentration, respectively. Quantitative amounts of some phenolic compounds in LAEC were investigated by high performance liquid chromatography-tandem mass spectrometry (LC-MS/MS). p-Hydroxy benzoic acid was found as the most abundant phenolic compound (55 mg/kg extract) in LAEC.

A new α-pyrone derivative1, along with four known congeners 2, 3, 4 and 5, were isolated from the solid-substrate fermentation medium of the endophytic fungus Pestalotiopsis microspore isolated from the branch of Taxus chinensis. Their structures and relative configurations were elucidated by extensive spectroscopic analysis. The cytotoxic activities of the isolated α-pyrone derivatives against two tumor cell lines as well as compound 1 ’ s antimicrobial activity against three bacteria and three plant-pathogenic strains were evaluated. No antimicrobial activity was observed for compound 1. The cytotoxicity against Caski and He L a tumor cell lines w as insignificant. To our surprise, the known compound 4 showed significant gibberellin synergistic activity towards Distylium chinense seeds.

In this study, Pseudomonas fluorescens 4.9.3 isolated from a sponge sample was investigated for its secondary metabolites. Two metabolites were isolated, and their structures were elucidated by 1D-, 2D NMR and LC-MS/MS experiments. The new compound (1) was established as (5R)-N-(2-(1H-imidazol-4-yl)ethyl)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydrooxazole-4-carboxamide, while the known metabolite was determined as pre-pseudomonine.

The aims of this study were to compare the chemical composition and antibacterial activity of four hydrodistilled oils of Ferula vesceritensis Coss. & Dur . Essential oils were obtained from the hydrodistillation of fresh flowers ( FF), dry flowers (DF), fresh stems (FS) and dry stems (DS). The GC-MS analyses of the oils revealed the presence of forty two compounds for FF, thirty seven compounds for DF, forty eight compounds for FS and thirty six components for DS. The total yields of the volatile essential oils were respectively: 97.9% (FF), 88.6% (DF), 96.4% (FS) and 87.4% (DS) with the prevalence of α -pinene (FF 32%, DF 16.1%, FS 11.5%, DS 17.4%), β-pinene (FS 8.1%, DS 8.9%), α - phellandrene (FF 8.5%, DF 24.3%), fenchylacetate (FF 10.4%, FS 7.3%, DS 8.8%), elixene (DF 6.3%, FS 5.4%), aristolene (FF 5.4%, FS 7.2%, DS 6.8%), caryophyllene oxide (FS 7.6%) and carotol (FF 13.9%, DF 10.7% FS 18.8%, DS 10.8%). The essential oils were tested againest 9 bacteria and showed a good antibacterial activity against almost food-borne pathogens and clinical isolated microorganisms at a concentration of 128 µ g/mL Minimum inhibitory concentration (MIC) values for all the bacteria were ranged between16 µ g/mL and 80 µ g/mL.

A new ent-kaurane diterpenoid, 2 β , 3 β , 6 β , 11 β -tetraacetoxy -ent -kaur-16 β - methy-15-one (1), along with three kown diterpenoids, hebeirubescensin L (2), rabescensin C (3), and trichokaurin (4) were isolated from the leaves of Isodon parvifolius. Their structures were elucidated on the basis of spectroscopic methods and literatures.

Twelve Unonopsis specimens, comprising five species commonly found at Amazonas state (Brazil) were collected in three different sites. The leaves of the specimens were extracted by hydrodistillation and analyzed by gas chromatography coupled to mass spectrometry (GC-MS). The data treated by chemometric analysis with the objective of verify the potential of their chemical profiles for chemotaxonomic approaches. Despite the essential oils presented spathulenol and caryophyllene oxide as a main constituent in most samples, the multivariate analysis showed significant differences between the species and their collection sites. The obtained results suggest high chemical similarity between U. floribunda and U. rufescens species and proved that U. guatterioides has a distinct chemistry when compared to the analyzed species. The chemical identification points to α-guaiene, α-calacorene and widdrol as possible chemical markers for U. floribunda and U. rufescens species.

Hydrodistillation of the ground flowering tops of Leucanthemum vulgare (Asteraceae), collected from Heyran (Ardabil Province, Iran), afforded a greenish yellow oil (yield 0.15%, v/w), which was analyzed by the GC-MS and the GC-FID. The volatile oil comprised 47 compounds representing 90.3% of the oil. Caryophyllene oxide (21.2%), aromadendrene oxide (13.7%), cis-β-farnesene (6.5%), 1-octen-3-yl-acetate (5.6%) and trans-caryophyllene (4.9%) were the major compounds. The volatile oil composition of L. vulgare collected from Iran (present study) was significantly different from that collected from elsewhere, indicating two possible chemotypes. The volatile oil showed free-radical-scavenging, antifungal and allelopathic effects.

Pleurospermum angelicoides Benth. , a herb used in folk medicine, was collected from near Milam glacier of Uttarakhand. Different plant parts were investigated for their terpenoid compositions, antifungal, antibacterial and antioxidant potential. Nothoapiole (5-allyl-4,6,7-trimethoxy-benzo[1,3] dioxide 1) was observed as a single major constituent (87.3%) in the root essential oil while α -asarone was the major constituent of leaf and flower essential oils (23.2%, 20.7% respectively). Monoterpenes viz. limonene, α-pinene, γ-terpinene and perilla aldehyde were other constituents of leaf and flower oils. All the essential oils exhibited broad range of antioxidant potential. The leaf essential oil showed significant antifungal activity against Candida albicans and Candida glabrata.

The phytochemical examination of the extract of bark of Millettia ovalifolia yielded chemical constituents, which included one novel flavonoid 7-(4-methoxyphenyl)-9H-furo [2, 3-f] chromen-9-one and four new source compounds characterized as 3,7-Dihydroxy-2-phenyl-4H-chromen-4-one, (E)-Ethyl-13-(3,4-dimethoxyphenyl)acrylate, (E)-Methyl-3-(3,4-dimethoxyphenyl)acrylate and N-Ethylacetamide. These compounds were characterized by using advance modern spectroscopic analytical techniques such as UV, IR, 1D, 2D NMR and mass spectrometry. The novel flavonoid (1) displayed significant inhibition of cytosolic form of bovine carbonic anhydrase-II with IC 50 value of 17.86 ± 0.07 µM. This flavonoid may be used as a new pharmacophore to treat cystic fibrosis, glaucoma, epilepsy, leaukomia and other disorders such as neurology etc.

Blastocyst implantation which is analogous to pro-inflammatory response, mediated by different inflammatory mediators and ovarian hormones found to be an effective target for the development of emergency contraceptives. In the present study, a series of derivatives an anti-inflammatory natural scaffold, lupeol were synthesized under mild reaction conditions and good yield. All the compounds were evaluated for acute anti-inflammation. The three active compounds with 62-92% edema protection were screened for chronic anti-inflammation. The analogue 3-(p-chlorocinnamoyl) lupeol ( 2) with potent anti-inflammatory activity (85% protection) was evaluated for t he anti-implantation activity by studying changes in superoxide dismutase (SOD) and lipid peroxidation (LPO) levels, visualization of implantation site and anti-estrogenic activity. As expected, a sharp decrease in superoxide anion radical and increase in SOD activity was seen in the endometrium of treated animals. Also no implantation sites were observed in the uterus of treated animals. The active compound also exhibited anti-estrogenic activity.

Antioxidants are the substances which significantly delay or prevent the development of age-related degenerative and chronic diseases caused by oxidative damage. Due to this, there is a considerable interest in the identification of lead molecules, which can inhibit the oxidation process or slow it down considerably. Based on the spectrofluorimetric analysis of superoxide and diphenylpicrylhydrazyl radical scavenging ability, the bio-assay guided isolation of methanolic extract of Nepeta floccosa Benth. was carried out. As a result of this study, one new flavanonol named nepetavanol (1) and four known flavonoids; dihydrokaempferol (2), naringenin (3), caulesnarinside (4), and poncirin (5) have been isolated. The structure of the new flavanonol was assigned on the basis of 1H- and 13C-NMR spectra including two-dimensional NMR techniques such as COSY, HMQC, and HMBC experiments and FABMS, EIMS, HR-MS data. Compound 1 , 2, and 3 showed significant activity whereas compounds 4 and 5 showed moderate activity against antioxidant assays.

The purpose of this study was to determine the phytochemical content of Cotula cinerea to establish principal components which may consolidate its use as a medicinal plant in the southeast of Morocco. The amount of total phenolic compounds as determined by analytical HPLC in methanol extracts was 79.23 ± 2.5 mg/g dry matter. The major phenolic compounds identified by HPLC-ESI-MS were neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid and luteolin-4´-O-glucoside. All compounds displayed very strong antioxidant capacities in the DPPH, FRAP and ORAC assays . The data indicates that methanol extracts of C. cinerea via their antioxidant capacities, may be effective disease prevention potions in traditional African medicine which is probably related to the significant content of echinoids and flavonoids.

Phytochemical investigation o n the ethanol extracts of Meliosma oldhamii Miquel branches led to the isolation of seven triterpene constituents: betulin ( 1 ) , lupeol ( 2 ) , oleanolic acid ( 3 ) , 3 b -acetoxyolean-12-en-28-acid (4), 3 b -acetoxyolean-12-en-28-aldehyde (5), 3 b -acetoxy-28-hydroxyolean-12-ene (6) and maslinic acid ( 7 ) . Their chemical structures were determined based on the spectr oscopic studies, as well as by comparison with literature data. Elastase inhibition activities were examined for the isolates using ursolic acid as a positive control . In this test , the compounds 1 and 3 proved to inhibit porcine pancreatic elastase with an IC 50 values of 39.3 and 39.5 m g/mL, indicating comparable activities to ursolic acid (IC 50 = 28.5 m g/mL). This study demonstrated that the M. oldhamii extract including triterpenes has potentials applicable as anti-wrinkle ingredient in cosmetic formulations. All of the compounds 1 - 7 were isolated for the first time from M. oldhamii.

Volatile components from florets, leaves and stems and branches of Centaurea aeolica Guss. harvested in Lipari, Sicily, Italy, were analysed by gas phase chomatography (GC) and gas chomatography mass spectrometry (GC-MS). The main constituents were β-eudesmol, caryophyllene oxide, ( E )-12-norcaryophyll-5-en-2-one and hexahydrofarnesylacetone in flowers, hexahydrofarnesylacetone, 2-methyloctadecane and tricosane in the leaves and hexadecanoic acid , caryophyllene oxide and β-eudesmol in the stems and branches . The analysis of the essential oil of the aerial parts of Centaurea diluta Aiton gave mainly fatty acids and derivatives, the main ones being hexadecanoic acid and (Z,Z)-9,12-octadecadienoic acid methyl ester.

Pluchea lanceolata (DC.) Oliv. & Hiern (Rasana) is an important medicinal plant due to its usage in number of Ayurvedic formulations. First time, chemical composition of essential oil from the aerial part of P. lanceolata was analyzed by gas chromatography-mass spectrometry (GC-MS) and NMR spectroscopy. Ex-vivo cholinesterase inhibitory activity of the essential oil was also evaluated using mouse brain homogenate. The major components were linalool (32.2%), β-caryophyllene (8.5%), α-terpineol (8.0%), spathulenol (7.4%), linalylacetate (5.6%), naphthalene, 1,6-dimethyl-4-(1-methylethyl)- (4.3%), α-copaene (3.6%), epi-cubebol (3.6%) and trans-α-bergamontene (3.1%). The experimental results showed that hydrodistilate of P. lanceolata significantly inhibited acetylcholinesterase activity (IC 50 value 2.54 ± 0.03 µg/mL).

The Syzygium (Family: Myrtaceae) species are well known for their aromatic nature. Though 45 Syzygium species are reported from the Western Ghats region of India, the volatile oil chemistry of most of these aromatic plants are uninvestigated. The present study reports the chemical constituents of the leaf essential oils of 6 Syzygium species, S. arnottianum Walp., S. caryophyllatum (L.) Alston, S. hemisphericum (Wight) Alston, S. laetum (Buch. Ham.) Gandhi, S. lanceolatum (Lam.) Wight & Arn. and S. zeylanicum (L.) DC. var. zeylanicum, collected from the Western Ghats of Kerala. Sesquiterpenoids were the predominantcompounds in all theSyzygium species studied and -caryophyllene and caryophyllene oxide were present in all the oils except S. laetum. The open chain sesquiterpenoids (Z,E)-α-farnesene and (E)-nerolidol were characteristic of S. laetum while phenyl propanoids were exclusively present in S. lanceolatum.

Two new analogs, a carboxy methyl (Argaminolic B) and a carboxy derivative (Argaminolic C), of a recently reported amino phenolic, Argaminolic A, isolated from the fruit of the argan tree, Argania spinosa(Skeels L.), are described. Argaminolic B exhibits facile hydrolysis of its methyl ester to yield Argaminolic C, which then undergoes a remarkably facile decarboxylation to the previously described Argaminolic A.

The essential oils of the fresh flower, leaf, and stem of Sempervivum brevipilum Muirhead. (Crassulaceae) were isolated by hydrodistillation in a modified Clevenger-type apparatus, and characterized by GC-FID and GC-MS. A total of fifty, fourty-three, and thirty-one compounds were identified, constituting over 92.6%, 92.6%, and 94.3% of oil composition of the flower, leaf, and stem of S. brevipilum, respectively. The chemical profile reveals the dominance of hydrocarbons (flower: 65.3%, leaf: 47.6%, stem: 71.1%). The major compounds of essential oils from S. brevipilum were tetracosane (20.2%) in flower, 1,2-diphenyl ethandione (16.1%) in leaf and docosane (30.5%) in stem. Monoterpene hydrocarbons were the major class of terpenoids in flower (2.2%) and in stem (1.8%), oxygenated diterpene was the major class of terpenoids in leaf (4.5%). Oxygenated monoterpenes were in minor amounts in all parts (flower: 0.3%, leaf: 0.7%, stem: 0.1%) of the plant. In addition, antimicrobial activities of the essential oils of S. brevipilum were investigated. The oils didn’t show any antibacterial and antifungal activity against tested bacteria, but showed high antituberculostatic activity against Mycobacterium smegmatis.

Chenopodiumambrosioides (Chenopodiaceae) growing wildly in Egypt was subjected to antioxidant –guided phytochemical investigation and the EtOAc fraction afforded the two new flavone glycosides; scutellarein-7-O-α-rhamnopyranosyl-(1→2)-α-rhamnopyranosyl-(1→2)-α-rhamnopyranoside (1) and scutella-rein-7-O-α-rhamnopyranosyl-(1→2)-α-rhamnopyranoside (2). In addition, the invitro antioxidant activities of the plant alcohol extract, CHCl 3 fraction, EtOAc fraction and isolates were studied.

The composition of the essential oils obtained by hydrodistillation from the aerial parts of Salvia pinnata L. (Labiatae), collected during flowering and fruiting periods, were analyzed by GC and GC-MS. 37 compounds were identified representing 96.1 % of the essential oil obtained from the plant material collected during flowering period. 30 compounds were detected constituting 94.7 % of the essential oil of the plant material collected in fruiting period. The main components of the essential oils were characterized as bornyl acetate, camphor, camphene, bornyl formate, a -pinene and borneol. The oils were screened for antimicrobial activity by the micro-dilution assay against standard bacteria (Escherichia coli, Salmonella enterica, Staphylococcus aureus, Enterococcus faecalis) and yeast (Candida albicans and Candida parapsilosis). Both of the oils showed antimicrobial activity against the tested organisms.

In the present study a new flavoniod 1 along with Betulin 2 Betulinic acid 3, Oleanolic acid 4 andUrsolic acid 5 were isolated from the aerial part of Viburnum grandiflorum Wall. ex DC as white amorphous powder from the chloroform fraction. On the bases of different modern spectroscopic techniques such as EIMS, UV, IR, NMR, HSQC, HMBC, COSY and NOESY the structure of compound 1 was elucidate as 6,7-bis (propenyloxy)-2-ethoxy-5-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one (Grandinoid).

Chemical composition of the essential oils obtained by hydrodistillation from the aerial parts of thirty six samples of perennial Spanish savouries (Satureja montana L., Satureja innota (Pau) G. López, Satureja cuneifolia Ten. and Satureja intricata Lange), was investigated by GC and GC-MS. A total of 72 compounds accounting between 98.25-99.55% of the total oil were identified. High content of carvacrol (59.72±1.50%) followed by g -terpinene (17.40±1.11%) were found in S.montana essential oils. S. cuneifolia yielded an oil rich in camphor (45.04±1.67%) and camphene (12.42±1.71%) whereas S. innota produces an essential oil with linalool (23.94±7.58%) or geraniol (8.62±3.45%) according to the locality of collection and S. intricata showed chemical polymorphism with camphor (16.02±1.75%), as the main compound followed with populations with myrcene (8.46±1.46%) and populations with g -terpinene (8.22±1.33%). Although the morphological affinity between S. innota, S.cuneifolia and S. intricata could lead to consider the subspecies level, the phytochemical discriminant analysis support the taxonomic classification of Flora Iberica which ranks these taxa into species.

The aim of this study was to investigate the chemical constituents of marine bryozoan Cryptosula pallasiana inhabiting Huang Island of China. Three aromatic compounds, p-methylsulfonylmethyl-phenol (1), p-hydroxybenzaldehyde (4) and methylparaben (5), nine alkaloids, 7-bromoquinolin-4(1H)-one (2), 7-bromo-2,4(1H,3H)-quinazolinedione (3), benzamide (6), phenylacetamide (7), 4(3H)-quinazolinone (8), thymine (9), uracil (10), hypoxanthine (11) and tryptophan (12), together with two glycerol derivatives, glycerol (13) and monoheneicosanoin (14), were isolated for the first time from this marine bryozoan. Among the isolates, compounds 1 and 2 were new natural products, and their spectral traits were reported for the first time. The structures of the two compounds were elucidated by extensive spectroscopic analyses, including HR-ESI-MS, EI-MS, 1D- and 2D-NMR techniques. The isolated compounds 1–3 were evaluated for their cytotoxicity against HL-60 human myeloid leukemia cell line. The results showed that bromated alkaloid (3) appeared strong cytotoxicity against HL-60 cells with IC 50 value of 11.87 µg/mL, while compounds 1 and 2 were inactivity.