Records of Natural Products Articles

Hemorrhoidal disease is a benign perianal disease, which is basically caused by vasodilation on pleux haemorrhoidalis vein, which affects mainly individuals at their active ages, and it is believed that the number of cases is much higher than the actual reported number. The majority of the patients’ complaints consist of pain, itching, bleeding and feeling of discomfort. Any patient with these symptoms requires a careful review of their personel history and a physical, digital examination. The treatment options are evaluated in a wide spectrum from conservative to surgical procedures. The main goal of the treatment is, in acute phase, relief of the symptoms quickly and in chronical phase prevention of the relapses. Before going to surgery, depends on the grade of the disease, human being very often apply local topical treatments, plant based intestinal regulators, plant based phlebotonics and anti-inflammatory drugs to improve or prevent the worsening of hemorrhoid. In this review, a brief information was given about hemorrhoid, in further the plants that were applied in traditional medicine, their latin, Turkish and common names, parts of the plants and their method of application in treatment of the symptoms in Anatolia. The data showed that herbal remedies included 170 from 60 different plant families used in the treatment of hemorrhoids. Although there are many natural based antihemorrhoidal preparations presence in the world, just a few safe antihemorrhoidal preparations prescribed in Turkey. This review will be a guide to discovery of different effective natural compounds from plants of different families such as Asteraceae, Lamiaceae and Rosaceae, which are highly rich in terms of antihemorhoidal compounds flavonoids and terpenes.

Eight benzenoids including three new phenols, piniphenols A–C (1–3), along with five known compounds, 4-vinylphenol (4) and 4-hydroxybenzaldehyde (5), 2-methoxy-2-(4'-hydroxyphenyl)ethanol (6), 2,3-dihydroxypropyl acetate (7), and phenol (8) were isolated from ethyl acetate layer of liquid fermentation with Porodaedalea pini (Hymenochaetaceae) BCRC 35384. All structures were established by spectral analysis and comparison with the literature data. Of these isolates, 1 showed moderate NO inhibitory activity with an IC 50 value of 60.0 μM . Compound 1 also showed the androgen receptor (AR) antagonism with the IC 50 value of 0.42 μM. To the best of our knowledge, this is the first report on benzenoid metabolites from the genus Porodaedalea .

The chemical composition of the essential oils (EOs) of four Lamiaceae (Thymus capitatus Hoff. et Link. , Rosmarinus officinalis L., Origanum vulgare L. and Mentha pulegium L.) growing wild in Tunisia was analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Obtained results showed significant variations among the different species. The major constituents identified for each species were respectively carvacrol (69%) and δ-terpinene (17%) for T. capitatus, 1,8-cineole (41%) and α-pinene (24%) for R. officinalis, menthol (39%) and 1.8-cineole (17%) for M. pulegium , thymol (30%), p-cymene (30%) and δ-terpinene (27%) for O. vulgare . EO herbicidal effects were evaluated against three invasive weed species in most cultivated crops: Sinapis arvensis L., Phalaris paradoxa L. and Lolium rigidum Gaud. The study of herbicidal activity was carried out on seed germination and seedling vigor and growth. All tested EOs significantly inhibited the germination and growth of weeds in a dose dependent manner and their herbicidal activity could be attributed mainly to their high content in oxygenated monoterpenes. The antifungal ability of EOs was assessed by using disc agar diffusion against ten plant pathogenic fungi affecting crops and stored foods. The EOs displayed strong inhibitory effect on all tested fungi. Our results on EOs chemical composition and biological activities showed properties that could be valorized in managing biocontrol of weeds and plant fungi.

In this study, we investigated the phytochemical composition, antioxidant, antimicrobial, and antigenotoxic properties of the aqueous extract of Dianthus carmelitarum for the first time. The phenolic and volatile compounds, antioxidant, antimicrobial and antigenotoxic activities of the extract were determined by HPLC and SPME-GC-FID/MS, spectrophotometric, agar well diffusion methods and comet assay, respectively. The polyphenolic content and ferric reducing power values of the extract were found 12.6 ± 0.27 mg gallic acid and 238 ± 2.89 μM trolox equivalents per g sample, respectively. Syringaldehyde and chlorogenic acid were detected as major phenolic compounds, while terpenes were determined as major volatile compound. Dianthus carmelitarum extract especially exhibited moderate antimicrobial activity against Mycobacterium smegmatis. Extract reduced H 2O 2-induced DNA damage in a concentration dependent manner in fibroblast cells compared to positive control (only 20 μM H 2O 2 treatment). Dianthus carmelitarum can be considered in the food, cosmetic, and drug industries due to its antioxidant, antimicrobial, and antigenotoxic activities.

A new ionol derivative, ( 2R, 6 S , 9 S ) -2-hydroxy -3-oxo-α-ionol (1), together with three known analogues, (6 S ,9 S )- 6-hydroxy- 3-oxo-α-ionol (2) , (6 R ,9 S )-3-oxo-α-ionol β -D- g lucopyranoside (3) and (6 R ,9 R )-3-oxo-α-ionol β -D-glucopyranoside (4), were isolated from the ethyl acetate extract of the aerial parts of Euphorbia tirucalli . Their structures were elucidated by means of extensive spectroscopic methods and comparison with the data reported in the literature. The absolute configuration of 1 was deduced by comparing experimental and calculated ECD spectra and 13C NMR data. The ionol d erivative s have been obtained for the first time from the genus Euphorbia.

Two new flavonoidsnamely 7,5′-dimethoxyisoetin (1) and homoorientin-6′′-4-O-methyl-myo-inositol (2) together with six known compounds were isolated and identified as isoorientin (3), genkwanin(4), dihydrokaempferol,7,4′-dimethylether (5), eriodictyol 7,4′-dimethylether (6), D-(+)-pinitol (7) and 3-O-β-D-glucopyranosyl spinasterol (8) from the aerial parts of endemic Phryna ortegioides for the first time. Their chemical structures were determined by 1D ( 1H, 13C and DEPT) and 2D (COSY, HSQC, ROESY, NOESY, TOCSY and HMBC) NMR and mass spectrometry. The antioxidant properties of pure secondary metabolites were analyzed on the basis of ferric thiocyanate method. Compound 1 displayed the highest antioxidant activity with an inhibition rate of 98.09% at a concentration of 100 µg/mL.

Six known compounds identified as 4',5-dihydroxy-6,7-(2,2-dimethylpyrano)-2'-methoxy-8-γ,γ-dimethylallyflavone (1), cudraflavone A (2), artocarpin(3), cycloartobiloxanthone (4), artonin E (5) and oxyresveratrol (6) were isolated from the stem barks of Artocapus scortechinii King. Another four compounds namely macakurzin C (7), flemichapparin A (8), luteolin (9) and apigenin (10) were isolated from the leaves. Structures of all pure compounds were elucidated spectroscopically using 1D NMR ( 1H, 13C, DEPT), 2D NMR (COSY, HMQC, HMBC), MS and FTIR, as well as by comparison with literature data. All isolated compounds were evaluated for their antioxidant capacities using 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) and ferric reducing antioxidant potential (FRAP) assays. Luteolin (9) showed the best ability to act as DPPH free radical scavenger with IC 50 value of 9.51 µM. Luteolin (9) also exhibited the strongest scavenger and potent ferric ion reducer compared to other isolated compounds in the ABTS and FRAP assays with IC 50 value of 124.4µM and 4.07 ± 0.180 mM FRAP equivalent respectively.

The fruits of Zanthoxylum leprieurii Guill. & Perr. (Rutaceae) are traditionally used in Africa, particularly in Cameroon, as a spice and in the treatment of sickle cell anaemia. Phytochemical investigation on the fruits of this plant afforded five kaurane diterpenes, i.e., kaurenoic acid (1), xylopic acid (2), ent-kauran-16β-ol (3), ent-16β-hydroxykauran-19-al (4) and ent-16β-hydroxykauran-19-oic acid (5). The structures of these diterpenes were determined comprehensively by spectroscopic means (1D and 2D NMR spectroscopy and MS analyses) and also by comparison with respective literature data. Among the isolated compounds, only kaurenoic acid (1) exhibited cytotoxicity against the PC3 cell line with an IC 50 value of 33.28 ± 9.14 µg/mL. To the best of our knowledge, this is the first report on the isolation of these kaurane diterpenes (1-5) from the genus Zanthoxylum.

Salvia tebesana Bunge (Lamiaceae) is an endemic medicinal species which grows wild in center of Iran. In the present study, chemical composition of the essential oil of the plant at two developmental stages (vegetative and full flowering) was reported for the first time. The essential oils were obtained by hydrodistillation from air-dried samples and analyzed by GC-FID and GC-MS. The yield of oil (w/w %) in different stages was in the order: full flowering (0.32 %) > vegetative (0.14 %). In total 44 and 61 constituents were identified and quantified in the studied samples representing 99.6 and 99.2 % of the total oil, respectively. The main constituents were 7-epi-α-eudesmol, (E)-nerolidol, (E)-caryophyllene, α-pinene, caryophyllene oxide, and δ-cadinen. Oxygenated sesquiterpens (43.7% and 48.2%) followed by sesquiterpene hydrocarbons (30.3% and 32.7%) were the main group of compound in the oil of the plant at vegetative and full flowering stages, respectively.

A new quinone derivative, named epoxyquinophomopsin (1), was isolated from the EtOAc extract of the fermentation broth culture of an endophytic fungus Phomopsis sp. from Morus cathayana . Structure of compound 1 was determined mainly by NMR and mass spectral data. Biogenetically compound 1 can be regarded as a degradative product of the previously reported anthraquinone found in the fungus .

The chemical composition of volatiles from the root of Stahlianthus campanulatus O. Kuzt (Zingiberaceae) has been studied. The essential oil was obtained by hydrodistillation and analyzed by GC (FID) and GC-MS. The components by identified by MS libraries and their LRIs. The major constituents of the oil were stahlianthusone (27.6%), a -copaene (16.7%) and camphor (14.7%). The chemical compositions of the essential oil of S. campanulatus are being reported for the first time.

A crude hydro-methanolic extract of Trillium govanianum ex D. Don ( Melanthiaceae, Trilliaceae ) rhizomes and its subsequent solvents soluble fractions were tested against different fungal strains i.e. Trichophyton rubrum ATCC 40051 , Aspergillusniger ATCC 16888, Candida albicans ATCC 18804, Microsporum canis ATCC 32903 and Fusarium lini ATCC 16888. The hydro-methanolic extract showed significant activity against T. rubrum and M. canis with 80 and 75% inhibitions respectively. Among the fractions, chloroform soluble fraction showed 90% inhibition, with minimum inhibitory concentration (MIC) of 10µg/mL against T. rubrum followed by ethyl acetate, butanol and n-hexane fractions. The bio-activity guided isolation of chloroform soluble fraction leads to a new trihydroxylated fatty acid, named govanic acid (1) along with two known phytoecdysteroids i.e. 20-hydroxyecdysone (2) and 5, 20-dihydroxyecdysone (3). The structures of isolated compounds were elucidated through 1D, 2D-NMR spectroscopic data analysis. All compounds (1-3) in T. govanianum are reported herein for the first time. Compound 1 showed significant activity against T. rubrum with 70% inhibition and MIC value of 5 µg/mL, but lack of activity against the other test strains.

The composition of essential oils of Rindera lanata (LAM). Bunge var. canescens (A.D.C) Kosn. obtained by hydro-distillation (HD) and microwave assisted distillation (MW) by GC, GC/MS. Thirty three and thirty nine compounds were identified in the oils representing 81.20% and 78.57% of the oils obtained by HD and MW respectively. Aldehydes were shown to be the main group of constituents of the MW 40.11% and 15.23%, respectively. However, the major group in the HD was found to be 25.35% alcohols and 23.78% hydrocarbons. 6-Methyl heptan-2-ol (15.97%) was the main compound of the HD. Furthermore, in the MW assisted essential oil, the major compound present was decane (10.50%). Terpenoid class compounds were found in essential oils and oxygenated monoterpenes were determined as major group (13.34% and 7.19%). Antimicrobial activity of the isolated essential oils of the plant was also investigated and they showed moderate antimicrobial activity against the tested microorganisms.