Records of Natural Products Articles
Articles In Press
Records of Natural Products
Articles In Press
1) A New Isoflavonolignan Glycoside from Abrus cantoniensis
A new isoflavonolignan glycoside, namely cantoniensin A (1), along with three known compounds were isolated from Abrus cantoniensis. The structure of the new compound was elucidated on the basis of spectroscopic analyses, including 1D-, 2D-NMR and HRESIMS. Compound 1 is the second example of isoflavonolignan glycoside from nature and is also the first isoflavonolignan isolated from the genus of Abrus.DOI http://doi.org/10.25135/rnp.125.19.01.1165 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Leguminosae Abrus cantoniensis cantoniensin A isoflavonolignan isoflavonolignan glycoside Available online: March 02, 2019 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
2) Thymol derivatives from Eupatorium fortunei
The presence of thymol derivatives in the leaves and twigs of E. fortunei collected in Northern Vietnam was investigated. Five thymol derivatives, including new 9-O-angeloxy-10-hydroxy-8-methoxythymol, 10-acetoxy-9-chloro-8,9-dehydrothymol, 9-acetoxy-8,10-epoxythymol-3-O-isobutyrate, 8,10-epoxy-9-hydroxy-thymol-3-O-tiglate, and 9-acetoxy-8,10-epoxythymol-3-O-angelate together with six other compounds, including taraxasteryl acetate, o-coumaric acid, trans-melilotoside, (–)-loliolide, coumarin, and b-sitosterol were isolated. The structures of the isolated compounds were determined on the basis of MS and NMR spectroscopic data.DOI http://doi.org/10.25135/rnp.22.214.171.1242 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Eupatorium fortunei Asteraceae thymol Available online: February 24, 2019 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
3) Structural Elucidation of a Coumarin with New Skeleton from Artemisia ordosica
A new coumarin, named as arteordocoumarin A (1), together with three known compounds (2-9) were isolated from the CHCl3 extract of Artemisia ordosica (A. ordosica). The structures of 1 was elucidated by spectroscopic methods, including UV, IR, HR-ESI-MS and extensive 1D and 2D NMR techniques.DOI http://doi.org/10.25135/rnp.126.96.36.1996 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Arteordocoumarin A Artemisia ordosica NMR Available online: February 24, 2019 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
4) Volatile oil constituents of Crataegus azarolus L. and Crataegus pallasii Grisb.*
In this study the volatile oils constituents of the inflorescence and unripe fruits of Crataegus azarolus L. and Crataegus pallasii Grisb. were investigated. Fifty-four compounds were identified by GC and GC-MS analysis. The major outstanding constituents of the essential oil in all samples (dried and fresh C. azarolus and dried C. pallasii) were; tricosane (33.8%, 29.3%, 34.0 %), pentacosane (24.6%, 21.1%, 30.8%), heptacosane (12.5%, 10.2%, 11.7%), and tetracosane (6.0%, 5.6%, 5.7%), respectively. Besides these alkanes, ten compounds (nonanal, β-elemene, undecanal, β-caryophyllene, (E, E)-α-farnesene, eicosane, hexyl benzoate, (Z)-3-hexenyl benzoate, (E)-2-hexenyl benzoate, docasane) were determined in all samples. Carvacrol, carvacryl acetate, carvone, and thymol were determined for the first time from C. pallasii essential oil. (E)-β-damascenone was determined only in dried C. azarolus oil; sesquiterpene compounds valencene, α-selinene and β-selinene, d-cadinene, germacrene D, selina-3,7(11)-diene, spathulenol, and d-cadinol were determined only in fresh C. azarolus sample. On the other hand (2E,6E)-farnesol was determined in dried C. azarolus and C. pallasii samples.
DOI http://doi.org/10.25135/rnp.188.8.131.520 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Crataegus azarolus Crataegus pallasii volatile constituents GC-MS analysis Available online: February 23, 2019 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
5) Polyacetylenes from the roots of Aralia dumetorum
A new polyacetylene, heptadeca-8,16-dien-4,6-diyn-3,l0-diol (1) along with four known polyacetylenes, 1,2-dihydrodendroarboreol B (2), heptadeca-1,8-dien-4,6-diyn-3,l0-diol (3), 3R, 8S-falcarindiol (4) and 3R,8R-dehydrofalcarindiol (5) were isolated from the ethanol extract of Aralia dumetorum. The structures of the isolates were elucidated on the basis of 1D and 2D NMR spectrums and by comparison of the spectroscopic data with those reported for structurally related compounds. The α-glucosidase inhibitory activity of compounds 1-5 was evaluated using α-glucosidase inhibitory assay, in which all compounds displayed good inhibitory activity with IC50 values ranging from 4.2 ~ 36.2 μM..DOI http://doi.org/10.25135/rnp.119.18.09.940 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Araliaceae Aralia dumetorum polyacetylenic compound α-glucosidase inhibitor Available online: February 11, 2019 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
6) NF-κB Inhibition Activity of Curcumin-Loaded Sterically Stabilized Micelles and Its Up-Regulator Effect on Enhancement of Cytotoxicity of a New Nano-Pirarubicin Formulation in the Treatment of Breast Cancer
This study aims to investigate the effects of co-administration of nano-Curcumin on anticancer effect of nano-Pirarubicin considering the fact that the clinical use of Pirarubicin and other anthracyclines has been limited by development of multidrug resistance (MDR) and based on previous data which have shown that Curcumin can down-regulate MDR proteins and suppress the activity of Nuclear factor-kappa B (NF-κB) a protein involved in chemoresistance. Nano micellar formulations of both Curcumin and Pirarubicin were separately synthesized using 1,2-Distearoyl-sn-glycero-3-phosphoethanolamine-N-methoxy-[poly(ethylene glycol); PEG MW 2,000] (DSPE-PEG2000). The produced sterically stabilized micelles (SSM) are very well known drug delivery systems in terms of their enhanced efficacy and good toxicity profile. We measured the differences of NF-κB levels in two different situations: when Pirarubicin is used alone and when it is co-administered with Curcumin. This study showed that co-administration of SSM-Curcumin (CSSM) and SSM-Pirarubicin (PSSM) with size of 12.81 nm enhances the efficacy of Pirarubicin by suppressing P65, an NF-κB subunit. Furthermore, we showed that SSM is able to successfully enhance water solubility and therapeutic stability of curcumin for using as a complementary agent.DOI http://doi.org/10.25135/rnp.184.108.40.2064 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Curcumin pirarubicin nanoparticles NF-κB breast cancer Available online: January 19, 2019 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
7) A New Ursane-Type Triterpene from the Roots of Salvia miltiorrhiza Bunge
Danshen (Salvia miltiorrhiza) is a one of the most well-known medicinal herbs in the Oriental medicine for treatment of certain cardiovascular disoders. Our current research on triterpenoid component in danshen roots led to the isolation of a new highly hydroxylated ursane-type triterpene, urs-12,20(30)-dien-3β,7β,24-triol-28-oic acid (2) and one known triterpene, epiasiatic acid (1). Their structures were elucidated on the basis of extensive spectroscopic analyses including NMR and MS spectra and comparison with literature data. The new compound 2 showed medium activity against HL-60 cells with the IC50 value of 16.3 μM. The obtained results of unique bioactive triterpenes from danshen contributed not only to its phytochemical profile associated with chemotaxanomy but also to biological evidence of the title plant.DOI http://doi.org/10.25135/rnp.97.18.07.330 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Danshen Salvia miltiorrhiza Lamiaceae triterpene Available online: January 19, 2019 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
8) Biodiversity and Secondary Metabolites of Marine Sponges from Turkey
Turkey is surrounded by the Black Sea, the Aegean Sea and the Mediterranean sea, comprising a rich source of marine biodiversity. Among all marine species, sponges with a wide range of secondary metabolites are an important potential for drug discovery. There are many studies on sponges and their secondary metabolites, but not enough study about Turkish sponges. The present review gives an overview of the current research trends on secondary metabolites from Turkish marine sponges and some of their biological activities. Until today alkaloids, steroids and phenolic compounds have been isolated and determined from Turkish sponges. To our knowledge, this is the first review about Turkish sponges. Furthermore, we have tried to introduce our Marine Herbarium of Ankara University Pharmacy Faculty (MAP).DOI http://doi.org/10.25135/rnp.118.18.07.340 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Bioactivity biodiversity secondary metabolite sponge Available online: January 14, 2019 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
9) New Xanthone from Millettia pachyloba Drake
A new xanthone, 1,7-dihydroxy-2,3,5,6-tetramethoxyxanthone (1), together with eight known compounds including one xanthone (2) and seven isoflavones (3-9) has been isolated from the leaves of Millettia pachyloba. This is the first report on the isolation of xanthone from the genus Millettia. The structure of the compound 1 was elucidated on the basis of spectroscopic data interpretation, including 1D and 2D NMR and HREIMS. Compound 1 exhibited weak cytotoxicity against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7 and SW480.DOI http://doi.org/10.25135/rnp.220.127.116.110 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Millettia pachyloba Drake Leguminosae xanthone Available online: January 10, 2019 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
10) Anti-inflammation C19-diterpenoid Alkaloids from Delphinium giraldii Diels
Two new C19-diterpenoid alkaloids named Delphinium alkaloid A (1) and Delphinium alkaloid B (2) were isolated from the Delphinium (Ranunculaceae). Their structures were elucidated by spectroscopic and mass-spectrometric analyses, including 1D-, 2D-NMR and HR-Q-TOF-MS. Compound 1 showed anti-inflammatory activity by regulating the inflammatory reaction induced by LPS in Caco2 cell.DOI http://doi.org/10.25135/rnp.117.18.09.954 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Delphinium giraldii Diels chemical constituents diterpenoid alkaloids anti-inflammatory Available online: January 07, 2019 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
11) Phenolic Derivatives from Dioscorea bulbifera
Two new phenolic derivatives, diosbulbiol A (1), diosbulbiol B (2), and six known compounds were isolated from Dioscorea bulbifera. Their structures was determined by MS, IR, UV, 1D- and 2D-NMR. The cytotoxicity of new compounds were evaluated against four cancer cell lines.DOI http://doi.org/10.25135/rnp.18.104.22.1683 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Dioscorea bulbifera dioscorea cytotoxicity phenolic derivatives diosbulbiol A diosbulbiol B Available online: December 25, 2018 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
12) A new pericarbonyl lignan from Amauroderma rude
A new pericarbonyl lignan (1), named amaurolignan A was isolated from an ethanol extract of the fruiting bodies in Amauroderma rude of family Ganodermataceae, together with two known lignans, 4-methoxymatairesinol 4′-β-D-glucoside (2) and lappaol F (3). The structures of compounds (1-3) were elucidated using NMR and MS spectroscopic methods.DOI http://doi.org/10.25135/rnp.22.214.171.1247 (DOI number will be activated after the manuscript has been available in an issue.) Keywords lignans Amauroderma rude Available online: December 25, 2018 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
13) Chemical Composition, Enantiomeric Distribution and AChE-BChE Activities of the Essential Oil of Myrteola phylicoides (Benth) Landrum, from Ecuador
The volatile constituents of the essential oil (EO) of Myrteola phylicoides (Benth) Landrum, from Ecuador, extracted by steam distillation have been analyzed. A total of 37 compounds, representing 90.30% the total essential oil sample were identified. Monoterpenes hydrocarbons (53.06%) and sesquiterpene hydrocarbons (35.24%) were the principal groups of compounds. The major components were identiﬁed as α-pinene (30.94%), (E)-caryophyllene (21.93%), β-pinene (14.45%) and α-humulene (9.56%). The essential oil of M. phylicoides showed weak in vitro activity against AChE inhibition with IC50 value 60.8 μg/mL and a low BChE activity with IC50 value >250 μg/mL. This is the first report on the chemical composition of the essential oil of this species.DOI http://doi.org/10.25135/rnp.112.18.09.893 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Myrteola phylicoides essential oil AChE BChE Available online: December 17, 2018 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
14) Cytotoxicity of Some Plants of the Asteraceae Family: Antiproliferative Activity of Psiadia punctulata Root Sesquiterpenes
According to the World Health Organization Cancer is the second leading cause of death globally. The methanol extracts of fourteen Middle-Eastern plants of the family Asteraceae were screened for antiproliferative activity on five cancer cell lines (A2780, MCF7, HeLa, RKO and Jurkat) by using MTT assay. Psiadia punctulata (DC.) Vatke was selected for isolation and elucidation of the bioactive constituents by 1D- and 2D-NMR, and MS analyses. Flow cytometry was used to evaluate cell cycle analysis, apoptotic hallmarks and reactive oxygen species. P. punctulata yielded a new sesquiterpene characterized as 7-hydroxy eudesman-3,5-dien-2-one (punctulin) (3) and three known sesquiterpenes: 1, 2 and 4. The antiproliferative activity of all sesquiterpenes was evaluated in Jurkat (T-cell leukemia) and HeLa cancer cell lines. Compound 1 (1β-hydroxy-8-oxo-cyperone) has induced a significant growth inhibition in Jurkat and HeLa cells (IC50 =12 and 18µM respectively). Flow cytometry of compound 1 has elucidated the mechanism of action by showing its ability to induce cell cycle arrest in Jurkat cells mainly in G0/G1 and, less markedly, in G2/M. Compound 1 also expressed strong antioxidant activity by reducing the basal level of peroxides DHFDA-load in Jurkat cells. Compound 1 antioxidant activity may have contributed to the observed cell cycle arrest.DOI http://doi.org/10.25135/rnp.126.96.36.1999 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Cytotoxic Activity Asteraceae Leukemia Cell cycle Sesquiterpenes Available online: December 15, 2018 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
15) Chemical Composition and Biological Activities of the Essential Oil from Aristolochia fordiana Hemsl
Abstract: The present study investigated the chemical composition of the essential oil obtained from the aerial parts of Aristolochia fordiana Hemsl (AF-EO) using GC-FID and GC-MS, and evaluated the in vitro biological activities of the essential oil. Forty-nine compounds representing 99.6% of the total oil were characterized. The main constituents were identified as β-chamigrene (17.0%), β-caryophyllene (11.1%), α-bulnesene (11.0%) and β-pinene (10.2%). Furthermore, the antibacterial activity of the essential oil of A. fordiana was studied using disc diffusion and micro-broth dilution assays. AF-EO exhibited a significant antibacterial activity against Staphylococcus aureus and Bacillus subtilis with MIC values below 100 μg/mL. Besides, the results of MTT assays indicated that the essential oil exhibited a moderate cytotoxic activity on HepG2 (liver hepatocellular cells) and MCF-7 (human breast adenocarcinoma cells) cell lines. However, the AF-EO showed a weak antioxidant activity in DPPH•, ABTS•+ and FRAP assays.DOI http://doi.org/10.25135/rnp.111.18.09.897 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Aristolochia fordiana Hemsl essential oil antibacterial activity cytotoxic activity antioxidant activity Available online: November 28, 2018 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
16) Assessment of Endemic Cota fulvida (Asteraceae) for Phytochemical Composition and Inhibitory Activities against Oxidation, -Amylase, Lipoxygenase, Xanthine Oxidase and Tyrosinase Enzymes
In the present work, chemical compositions of essential oil and methanol extract of endemic Cota fulvida (Grierson) Holub were investigated as well as their antioxidant, antidiabetic, antiinflammatory and antimelanogenesis potent. The phytochemical analyses have been performed with GC-MS/FID and LC-MS/MS techniques. The essential oil was characterized with hexadecanoic acid (25.6 %), camphor (6.1 %), caryophyllene oxide (5.3 %), 1,8-cineole (4.9 %) and humulene epoxide (3.9 %). In the extract, phenolic acids, phenylpropanoid dimer and flavonoids were detected. The major constituents of the extracts were found to be 5-feruloylquinic acid, caftaric acid, 3,5-O-dicafeoylquinic acid and quercetin rutinoside. The antioxidant activities of the oil and extract were evaluated through scavenging of free radicals, inhibition of linoleic acid peroxidation and superoxide anion radical (O2-) generated by xanthine - xanthine oxidase (XO) system. The extract showed free radical scavenging activity (IC50 0.131 mg/mL), Trolox equivalent antioxidant capacity (1.33 mM) and inhibited (Inh. 36.3 %) peroxidation of lipids. The oil and extract demonstrated significant hypoglycemic activity via inhibition of porcine pancreatic a-amylase. The antiinflammatory effects of the oil and extract via inhibition of 5-LOX enzyme were found as 53.7 % and 23.9 %, respectively. The extract demonstrated moderate inhibitory effect (23.3 %) on oxidation of L-DOPA via inhibition of tyrosinase enzyme.DOI http://doi.org/10.25135/rnp.109.18.09.875 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Cota fulvida Essential Oil Extract GC-MS/FID LC-MS/MS Antioxidant Available online: November 15, 2018 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
17) The Chemical Composition of Volatile Oil and Biological Activity of Rhododendron caucasicum
The aim of this research was to investigate the effect of different extraction methods and chemical composition of the essential oil and solid-phase microextraction (SPME) from Rhododendrum caucasium Pall. The volatiles of R. caucasicum have been isolated by hydro distillation (HD) and SPME. The compositions of the volatiles were characterized by GC-FID/MS. A total of twenty-five and thirty-one compounds were identified constituting over 89.25%, and 90.33% of volatiles obtained with HD and SPME, respectively. The main volatile constituents of R. caucasicum were found to be calarene (46.13% (HD) and 54.91% (SPME)) and sandaracopimaradiene (25.93% (HD) and 8.16% (SPME)). Furthermore, the obtained essential oil (EO) and solvent extracts (n-hexane and methanol) of R. caucasicum were tested against the following nine bacteria: Escherichia coli, Yersinia pseudotuberculosis, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Bacillus cereus, Mycobacterium smegmatis, Candida albicans, and Saccharomyces cerevisiae. The EO showed moderate antimicrobial activities with the inhibition zone from 6 to18 mm against E. faecalis, S. aureus, B. cereus and M. smegmatis, respectively. Methanol extract gave better antimicrobial activity against the P. aeruginosa, E. faecalis, S. aureus, and B. cereus with the almost 15 mm inhibition zones.DOI http://doi.org/10.25135/rnp.107.18.09.952 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Rhododendron caucasicum; hydrodistillation; SPME; essential oil; antimicrobial activity; GC-FID/MS. Available online: November 15, 2018 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
18) Glutinosine A: A New Morphinandienone Alkaloid from Litsea glutinosa
A new morphinandienone alkaloid, named glutinosine A was isolated from the root barks of Litsea glutinosa. The new structure was determined by various spectroscopic techniques including 1D (1H-, 13C-NMR), 2D-NMR (HMBC, HSQC, COSY and ROESY) and high resolution electrospray ionization mass spectrometry (HR-ESI-MS). The effects of the new compound on glucose consumption in HepG2 cells were evaluated. Whereas, the result showed that this compound displayed no activity in stimulating glucose consumption.DOI http://doi.org/10.25135/rnp.92.18.06.306 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Litsea glutinosa Glutinosine A morphinandienone glucose consumption activities Available online: November 12, 2018 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
19) Chemical Compositions of Essential Oil of Piper Species from Atlantic Forest of Amazonia, Brazil
Essential oils from the leaves of Piper japurense, P. coariense, P. auriculifolium, P. curtistilum, P. alatipetiolatum and P. brevesanum from the Amazon Forest (Brazil) were obtained through hydrodistillation. The chemical composition of the oils was determined using gas chromatography and mass spectrometry, which revealed the presence of 108 compounds representing 95.14 ± 0.35%, 95.64 ± 0.59%, 95.57 ± 0.48%, 92.05 ± 0.27%, 96.24 ± 1.04% and 91.31 ± 0.76% of the oils, respectively. The major components were α-eudesmol in the P. japurense (22.05 ± 0.15%) and P. coariense (27.33 ± 0.33%) oils, premnaspirodiene (32.26 ± 0.03%) in the P. auriculifolium oil, caryophyllene oxide (28.69 ± 0.17%) in the P. curtistilum oil, linalool (43.88 ± 0.50%) in the P. alatipetiolatum oil and β-elemene (12.75 ± 0.06%) in the P. brevesanum oil.DOI http://doi.org/10.25135/rnp.110.18.09.904 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Piper ssp Amazonia biome Essential oil Premnaspirodiene Available online: November 12, 2018 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
20) A New Diterpene: Abietane Glycoside from the Roots of Isodon rugosus Wall Ex Benth.
The methanolic extract of the roots of Isodon rugosus were subjected to chromatographic separation, yielded two diterpenes: a new compound named rugosodon 1 and a known compound oridonin 2. The new compound 1 was elucidated as 1-O-α-D-glucopyranosyl-7α,13β-dihydroxyabieta-8(9)-en-11-one and the known compound 2 as 7α,20-epoxy-1α,6β,7,14-tetrahydroxy-kaur-16-en-15-one (oridonin), based on the chemical hydrolysis, physicochemical and spectroscopic data of IR, ESIMS, EIMS, 1D, and 2D NMR. The compounds 1-2 were subjected to bioassay studies of cytotoxicity and α-glucosidase inhibition potential. Rugosodon 1 showed significant potential of α-glucosidase inhibition with IC50 0.453 mg/mL, as compared to the standard acarbose (IC50 0.921 mg/mL). The compounds 1-2 failed to show any significant results for the cytotoxic screening against the three human cancer cell lines (NCI-H460, HeLa and MCF-7).DOI http://doi.org/10.25135/rnp.101.18.06.310 (DOI number will be activated after the manuscript has been available in an issue.) Keywords Abietane diterpene glycoside Isodon rugosus rugosodon oridonin Available online: November 11, 2018 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.