Records of Natural Products

Articles In Press

Original Article

1) 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

Rec. Nat. Prod. (2018) in press ; 1 - 15
by Zahra Eskandari , Fatemeh Bahadori , Melda Altikatoglu , Vildan Betul Yenigun , Abdurrahim Kocyigit and Hayat Onyuksel
Abstract

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.108.18.10.984
(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
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Short Report

2) A New Ursane-Type Triterpene from the Roots of Salvia miltiorrhiza Bunge

Rec. Nat. Prod. (2018) in press ; 1 - 5
by Le Quoc Hung, Phuong Thien Thuong and Nguyen Huu Tung
Abstract

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
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Review Article

3) Biodiversity and Secondary Metabolites of Marine Sponges from Turkey

Rec. Nat. Prod. (2018) in press ; 1 - 12
by Hajar Heydari , Bulent Gozcelioglu and Belma Konulugil
Abstract

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
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Original Article

4) New Xanthone from Millettia pachyloba Drake

Rec. Nat. Prod. (2018) in press ; 1 - 5
by Zhi Na , Qishi Song and Qingfei Fan
Abstract

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.116.18.10.1020
(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
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Original Article

5) Anti-inflammation C19-diterpenoid Alkaloids from Delphinium giraldii Diels

Rec. Nat. Prod. (2018) in press ; 1 - 6
by Yan Liu , Zhiyang Liu , xinyi wang , Jing Zhang , Fangfang Liu and Yunlong Cong
Abstract

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
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Original Article

6) Phenolic Derivatives from Dioscorea bulbifera

Rec. Nat. Prod. (2018) in press ; 1 - 6
by Guokai Wang , Juan Zheng , Jaising Yang , Yunpeng Sun , Nan Zhang , Huiwen Liu and Guo-Kai Wang
Abstract

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.114.18.10.1003
(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
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Original Article

7) A new pericarbonyl lignan from Amauroderma rude

Rec. Nat. Prod. (2018) in press ; 1 - 5
by Miao Dong , Zuhong Ma , Qiaofen Yang , Qiuyue Hu , Yanqing Ye and Min Zhou
Abstract

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.115.18.10.1007
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
lignans Amauroderma rude
Available online: December 25, 2018
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Original Article

8) Chemical Composition, Enantiomeric Distribution and AChE-BChE Activities of the Essential Oil of Myrteola phylicoides (Benth) Landrum, from Ecuador

Rec. Nat. Prod. (2018) in press ; 1 - 8
by James Calva , Jessica M Castillo , Nicole Bec , Jorge Ramirez , José Miguel Andrade , Christian Larroque and Chabaco Armijos
Abstract

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
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Original Article

9) Cytotoxicity of Some Plants of the Asteraceae Family: Antiproliferative Activity of Psiadia punctulata Root Sesquiterpenes

Rec. Nat. Prod. (2018) in press ; 1 - 9
by Ammar Bader , Qasem Abdallah , Mohamed Abdelhady , Nunziatina De Tommasi , Nicola Malafronte , Usama Shaheen , Majdi Bkhaitan and Roberta Cotugno
Abstract

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.113.18.10.969
(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
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Original Article

10) Chemical Composition and Biological Activities of the Essential Oil from Aristolochia fordiana Hemsl

Rec. Nat. Prod. (2018) in press ; 1 - 9
by Pengxiang Lai , Xiao-Dan Su , Yang Gao , Yingxin Xiang , Pengxiang Lai and Xiang Xing
Abstract

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
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Original Article

11) Assessment of Endemic Cota fulvida (Asteraceae) for Phytochemical Composition and Inhibitory Activities against Oxidation, -Amylase, Lipoxygenase, Xanthine Oxidase and Tyrosinase Enzymes

Rec. Nat. Prod. (2018) in press ; 1 - 13
by Gulmira Özek , M. Ufuk Özbek , Süleyman Yur , Fatih Göger , Munevver Arslan and Temel Özek
Abstract

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
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Original Article

12) The Chemical Composition of Volatile Oil and Biological Activity of Rhododendron caucasicum

Rec. Nat. Prod. (2018) in press ; 1 - 8
by Seda Fandaklı , Nurettin Yaylı , Nuran Kahriman , Emel Uzunalioğlu , Nevin Ulaş Çolak , Sercan Yıldırım and Ahmet Yasar
Abstract

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
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Short Report

13) Glutinosine A: A New Morphinandienone Alkaloid from Litsea glutinosa

Rec. Nat. Prod. (2018) in press ; 1 - 4
by Yubin Ji, Chenxu Wang, Yuchen Zhang, Caiyun Zhang, Di Cui and Xiaopo Zhang
Abstract

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
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Original Article

14) Chemical Compositions of Essential Oil of Piper Species from Atlantic Forest of Amazonia, Brazil

Rec. Nat. Prod. (2018) in press ; 1 - 9
by Claudio Augusto Gomes da Camara , Carolina Alves de Araujo , Marcilio Martins de Moraes , Geraldo José Nascimento de Vasconcelos , Charles Eugene Zartman and Marta Regina Silva Pereira
Abstract

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
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Original Article

15) A New Diterpene: Abietane Glycoside from the Roots of Isodon rugosus Wall Ex Benth.

Rec. Nat. Prod. (2018) in press ; 1 - 9
by Arif Ullah, Ghias Uddin, Mamoon Ur Rashid, Ismail Ismail, Nasruddin, Bina Shaheen Siddiqui, Zahoor Ullah, Muhammad Alamzeb
Abstract

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
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Original Article

16) Chemical Composition and Anti-Candida and Anti- Trypanosoma cruzi Activities of Essential Oils from the Rhizomes and Leaves of Brazilian Species of Renealmia L. fil.

Rec. Nat. Prod. (2018) in press ; 1 - 13
by Kathlyn V. Gevú, Helena R.P. Lima, Ilzenayde A. Neves, Érica O. Mello, Gabriel B. Taveira, Laís P. Carvalho, Mário G. Carvalho, Valdirene M. Gomes, Edésio J.T. Melo and Maura Da Cunha
Abstract

This work aimed to determine the chemical composition of essential oils from rhizomes and leaves of Renealmia chrysotricha Petersen, R. breviscapa Poepp. & Endl. and R. nicolaioides Loes., and to evaluate the biological activities of these oils on three Candida species and the parasite Trypanosoma cruzi. The rhizomes and leaves were collected in the Atlantic and Amazon rainforests. Essential oils were isolated and characterized by gas chromatography. Βeta-Caryophyllene was found to be the most predominant compound in the essential oils of rhizomes and leaves of R. breviscapa, and the rhizomes of R. nicolaioides, whereas (E)-nerolidol was the most abundant compound in the oils of leaves of R. nicolaioides. In R. chrysotricha, α-terpineol, coronarin-E and 1,8-cineole were found to be the most predominant compounds in the essential oils of rhizomes, whereas cis-3-hexenol was predominant in the leaves. The tested oils did not inhibit C. albicans growth at 1000 µg/mL, whereas leaf oils from R. chrysotricha and R. nicolaioides inhibited the growth of C. buinensis and C. tropicalis by about 50%. Essential oils from the rhizomes and leaves of R. chrysotricha exhibited efficient antiparasitic activity against Trypanosoma cruzi. Damage to T. cruzi epimastigotes was confirmed by LM and TEM.

DOI
http://doi.org/10.25135/rnp.105.18.08.125
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Zingiberaceae rhizomes leaves terpenoids anticandidal activity antiparasitic activity.
Available online: November 01, 2018
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Original Article

17) Curcuma kwangsiensis Extracts Produced Antioxidant Effects Against Injury Induced by H2O2 on PC12 Cells

Rec. Nat. Prod. (2018) in press ; 1 - 14
by Juxiang Liu, Lianli Zhang, Jinyang Zhang, Baocai Li and Mi Zhang
Abstract

The radix of Curcuma kwangsiensis S. G. Lee & C. F. Liang (Zingiberaceae) is a traditional medicine in China, and used for treating qi stagnation and blood stasis. Previous chemical study showed it is rich in sesquiterpenoids and diarylheptanoids, similar to those in Curcuma longa L., which showed obviously protective effects against oxidative damage. However, the antioxidant and underlying mechanism of C. kwangsiensis has not been studied yet. In current study, the antioxidant activities of C. kwangsiensis extracts (ECWs), including 95 % EtOH extract (HCECW), 75 % EtOH extract (MCECW), methanol extract (MECW), dichloromethane extract (DECW) and petroleum ether extract (PECW), and their possible mechanisms, were studied on the model of H2O2-induced PC12 cell damage in vitro. The results showed different concentrations (1, 10, 50 µg/mL) of HCECW, MCECW and DECW could increase damaged PC12 cell viability significantly. In the extract-treated groups, the release rate of LDH significantly decreased, while SOD, CAT, and GSH markedly increased. In the meantime, the intracellular Ca2+ and cell apoptosis decreased significantly, while MMP increased and apoptosis morphology was clearly improved. Compared with the model group, they produced effects on up-regulating of Bcl-2, down-regulating of Bax and Caspase-3. Further, the chemical analysis of those five extracts by UPLC-DAD-Q-TOF-MS showed their major constituents were sesquiterpenoids and diarylheptanoids, indicating both of them presented in ECWs are antioxidant substances in this plant. This study provided an experimental basis for the future development of antioxidants from the genus Curcuma.

DOI
http://doi.org/10.25135/rnp.104.18.08.342
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Curcuma kwangsiensis antioxidant effect PC12 cell oxidative injury chemical analysi
Available online: October 28, 2018
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Original Article

18) New Diterpenes Isolated from the Colombian Caribbean Soft Coral Pseudoplexaura flagellosa and Their Cytotoxic Properties

Rec. Nat. Prod. (2018) in press ; 1 - 11
by Katherine Bauer, Mónica Puyana, Leonardo Castellanos and Edisson Tello
Abstract

Studies about secondary metabolites isolated from soft corals around the world have proven the potential of these organism as producers of compounds with a potent cytotoxic activity. In this work, we obtained the extract of Pseudoplexaura flagellosa collected in Santa Marta, Colombia, the cytotoxic activity of this extract, fractions and compounds was established against SiHa (ATCC® HTB-35™), MDA-MB-231 (ATCC® HTB26™), A549 (ATCC® CRM-CCL-185™), PC3 (ATCC® CRL1435), and L929 (ATCC® CCL1™) cell lines. The results showed that the extract of soft coral P. flagellosa has cytotoxic activity with an IC50 of 35.4, 72.3, 49.8 and 40.5 μg/mL against SiHa, A549, PC3 and MDA-MB-231 cell lines, respectively. Thus, this extract was repeatedly subjected to different chromatographic columns and final purification of these fractions afforded pure compounds 14, which were elucidated by 1D and 2D NMR experiments including 1H, 13C, COSY, HSQC, HMBC and NOESY, and HRESIMS. In addition, Mosher method was used to establish the stereochemistry of compound 2 and chemical interconversion allow establishing the stereochemistry of compound 1. These results let to conclude that compound 2 is a new stereoisomers of acetylated asperdiol previously reported on literature. Additionally, three analogues 5, 6, and 7 were synthesized from compound 1 and the cytotoxic activity of all compounds was evaluated using doxorubicin as positive control. The results showed that 6 (IC50 of 19.3, 23.7, 13.4 and 18.7 μg/mL against SiHa, A549, PC3 and MDA-MB-231, respectively) was the most active compound against all the cancer cell lines.

DOI
http://doi.org/10.25135/rnp.100.18.07.325.1
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Pseudoplexaura flagellosa cytotoxic activity absolute stereochemistry stereoisomers soft corals
Available online: October 28, 2018
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Original Article

19) Bioactivity-Guided Isolation of Anti-Inflammatory Principles from Cistus parviflorus Lam.

Rec. Nat. Prod. (2018) in press ; 1 - 10
by Perihan Gürbüz , Şengül Dilem Doğan , Gizem Nur Çelik , Hatice Bekci , Ahmet Cumaoğlu , Miyase Gözde Gündüz and Mehmet Yavuz Paksoy
Abstract

Bioactivity-guided fractionation and purification of Cistus parviflorus led to the isolation of two flavan-3-ol derivatives; gallocatechin (1) and epigallocatechin (2) and two flavonoid glycosides; avicularin (3) trans-tiliroside (4). The structures of the compounds were elucidated on the basis of NMR and ESIMS data. All compounds were isolated from C. parviflorus for the first time. Compounds 2 and 3 exhibited anti-inflammatory activity through decreasing the NOS2 and COX2 levels on LPS+IFN-γ treated RAW 264.7 cells. Molecular docking studies of avicularin, the most potent compound, were carried out in the active sites of NOS2 and COX2 to predict the most plausible binding modes and support the experimental data.

DOI
http://doi.org/10.25135/rnp.106.18.09.883
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Cistaceae; inflammation; flavonoids; structure elucidation; avicularin; molecular modelling
Available online: October 24, 2018
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Short Report

20) Essential Oil Constituents from the Leaves of Anoectochilus setaceus, Codonopsis javanica and Aristolochia kwangsiensis from Vietnam

Rec. Nat. Prod. (2018) in press ; 1 - 6
by Tran M. Hoi, Do N. Dai, Chu T. T. Ha, Ha V. Anh and Isiaka A. Ogunwande
Abstract

There are very few reports on the phytochemistry of Anoectochilus setaceus Blume, Codonopsis javanica (Blume) Hook. f. and Aristolochia kwangsiensis Chun & F.C.How ex S.Yun Liang species in the literature. Here we present essential oil compositions of the three endemic plants from Vietnam. The analysis of the chemical constituents of the hydrodistilled essential oils was achieved by using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The essential oils of A. setaceus, C. javanica and A. kwangsiensis afforded very low oil yields: 0.12%, 0.31% and 0.10% (v/w), respectively, calculated on a dry weight basis. The result indicated that the major components of the leaf oil of A. setaceus consist mainly of α-cadinol (17.1%), (E,E)-farnesol (14.0%) and terpinen-4-ol (11.0%) while β-pinene (20.8%) and α-pinene (15.4%) were the main compounds identified in C. javanica. However, the significant compounds of A. kwangsiensis were sabinene (34.8%), β-caryophyllene (8.8%) and terpinen-4-ol (8.6%). To the best of our knowledge this is the first report on the essential oil compositions of these species.

DOI
http://doi.org/10.25135/rnp.103.18.08.124
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Anoectochilus setaceus Codonopsis javanica Aristolochia kwangsiensis essential oil terpenoids.
Available online: October 16, 2018
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Original Article

21) Inhibitory Effects of Metabolites Isolated from Artemisia dracunculus L. Against the Human Carbonic Anhydrase I (hCA I) and II (hCA II)

Rec. Nat. Prod. (2018) in press ; 1 - 10
by Tuba Aydın, Bayram Yurtvermez, Murat Şentürk, Cavit Kazaz and Ahmet Çakır
Abstract

Tarragon or Dragon's-wort (Artemisia dracunculus L.) is widely used as spice and in traditional medicine in various regions of the world. Inhibitory effects of the n-hexane, dichloromethane, ethanol and methanol extracts of the leaves of tarragon on the human carbonic anhydrase (hCA) I and II enzymes were investigated. Dichloromethane extract exhibited the strongest activity with lowest IC50 value (0.020 and 0.031 μg/mL, respectively). The chromatographic studies on the dichloromethane extract of tarragon allowed the isolation of six known strong inhibitors of hCA isozymes as trans-anethole, stigmasterol, herniarin, (2E,4E)-N-isobutylundeca-2,4-dien-8,10-diynamide, (2E,4E)-1-(piperidin-1-yl)undeca-2,4-diene-8,10-diyn-1-one and 1-(4'-methoxyphenyl)-1,2,3-trihydroxypropane. The compound, 1-(4'-methoxyphenyl)-1,2,3-trihydroxypropane was isolated from tarragon for the first time in this study. Among the tested compounds, 1-(4'-methoxyphenyl)-1,2,3-trihydroxypropane showed the highest inhibitiory impact on both hCA isozymes. Also its IC50 values were found lower than positive control, acetazolamide.

DOI
http://doi.org/10.25135/rnp.102.18.07.329
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Artemisia dracunculus L. 1-(4'-methoxyphenyl)-1 2 3-trihydroxypropane enzyme inhibition hCA I hCA II.
Available online: October 14, 2018
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Original Article

22) Phytochemical Profiles and Antioxidant Activity of Salvia species from Southern Italy

Rec. Nat. Prod. (2018) in press ; 1 - 11
by Marzia Vergine, Francesca Nicolì, Carmine Negro, Andrea Luvisi, Eliana Nutricati, Rita Annunziata Accogli, Erika Sabella and Antonio Miceli
Abstract

The purpose of this research was to investigate phytochemical profiles and antioxidant activity in four Salvia species growing in Salento (Southern Italy). The hydrodistillation products obtained from the aerial parts of Salvia clandestina, Salvia fruticosa, Salvia officinalis and Salvia sclarea were characterized by GC–MS and 50 compounds were detected. With the exception of S. clandestina, that did not produce essential oils, the other species shared different amounts of monoterpenes oxygenated (camphor 2.13%-9.16%) and sesquiterpenes hydrocarbons (caryophyllene 4.65%-18.33%; humulene 1.87%-12.39%). The phenolic profiling, analyzed by HPLC ESI/MS-TOF, highlights that S. clandestina is a rich source of danshensu (4.76 mg/g DW) while S. sclarea of rosmarinic acid (15.57 mg/g DW). Mutivariate statistical analysis (PCA) of hitherto studied Salvia phenols have shown similarities in profiles between S. fruticosa and S. officinalis, while S. clandestina and S. sclarea showed distinctive profiles. Otherwise, essential oil profiles analysed by PCA are clearly different among the three productive species. The extracts from collected plants were found to be effective antioxidant in three different in vitro assays (DPPH, ABTS, FRAP and Superoxide anion scavenging activity). Thus, they can be proposed as natural ingredients in functional foods, herbal medicines or as sources of bioactive molecules.

DOI
http://doi.org/10.25135/rnp.96.18.07.119
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Salvia clandestina L. Salvia fruticosa Mill. Salvia officinalis L. Salvia sclarea L. essential oils phenolic compounds.
Available online: October 10, 2018
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Original Article

23) Two New Lipodepsipeptides from the Endophytic Fungus Colletotrichum aotearoa Y41

Rec. Nat. Prod. (2018) in press ; 1 - 6
by Yang Wu, Juanli Zhang, Wenxing Xiang, Mingzi Wang and Chunhua Lu
Abstract

Two closely related lipodepsipeptides, with the same 12-membered oxodepsipeptide ring system, aotearolides A (1) and B (2), together with 1H-indole-3-carbaldehyde (3) and 2-(1H-indol-3-yl)acetic acid (4) were isolated from the endophytic fungal isolate Colletotrichum aotearoa Y41 of Huperzia serrata. The structures were elucidated on the basis of their high-resolution ESI/MS, 1D and 2D NMR spectroscopic data.

DOI
http://doi.org/10.25135/rnp.90.18.05.298
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Lipodepsipeptide aotearolides A and B Colletotrichum aotearoa Huperzia serrata
Available online: October 08, 2018
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Original Article

24) Cytotoxic Activity-Guided Isolation Studies on Fumana procumbens (Dunal) Gren. & Godr.

Rec. Nat. Prod. (2018) in press ; 1 - 10
by Esra Emerce, Perihan Gürbüz, Şengül Dilem Doğan, Ela Kadioglu and Ipek Süntar
Abstract

Among the plant secondary metabolites much attention has been given to naturally occurring phenolic compounds as attractive candidates for cancer treatment and prevention. Fumana procumbens (Dunal) Gren. & Godr (Cistaceae) is a perennial herb, distributed in inner and southwest Anatolia, Turkey. F. procumbens was shown to be rich in phenolic constituents especially flavonoids and biflavonoids which are known for their antioxidant and anticarcinogenic effects. Thus, this study aims to investigate the anticancer activity of F. procumbens extracts, fractions and pure compounds by MTT test against HeLa, MCF-7, and A549 as well as BEAS-2B cell lines for determining selectivity. Bioactivity-guided phytochemical investigation on Fumana procumbens (Dunal) Gren. & Godr. led to the isolation and identification of three biflavonoids: genkwanol A, dihydrodaphnodorin B and stelleranol. The structures were elucidated by extensive 1D- and 2D-NMR spectroscopic analysis in combination with MS experiments. This is the first report on the isolation of genkwanol A and stelleranol from the genus Fumana and from the family Cistaceae. As a result, no individual cytotoxic activity was obtained for biflavonoid compounds. However, the former fractions FrC and FrD as well as MeOH and n-BuOH extracts exerted moderate and significant cytotoxic activity which suggested a possible synergistic effect.

DOI
http://doi.org/10.25135/rnp.98.18.07.331
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Anticancer activity Cistaceae Fumana procumbens cell viability cytotoxicity MTT test.
Available online: October 01, 2018
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Original Article

25) Triterpenoids from Acokanthera schimperi in Ethiopia

Rec. Nat. Prod. (2018) in press ; 1 - 7
by Wondwonsen A. Matebie, Wanchang Zhang, Shuo Zhang and Guangbo Xie
Abstract

The studies on the leaves of Acokanthera schimperi, a traditional herb of Ethiopia, afforded eight triterpenoids, including a new triterpenoid ester, lupan-20-ol-3(b)-yl 3-hydroxyoctadecanoate (1), along with seven known triterpenoids, lupeol (2), 28-nor-urs-12-ene-3b,17b-diol (3), ursolic aldehyde (4), 3b-hydroxy-oleana-11,13(18)-dien-28-oic acid (5), alagidiol (6), oleanolic acid (7) and ursolic acid lactone (8). ir structures were determined by spectroscopic methods including 2D NMR techniques and X-ray diffraction analysis.

DOI
http://doi.org/10.25135/rnp.94.18.07.324
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Acokanthera schimperi triterpenoids Ethiopian medicinal plants spectroscopic analyses X-ray diffraction.
Available online: September 30, 2018
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Original Article

26) Composition of the Essential Oils of Two Endemic Helichrysum Species in Turkey

Rec. Nat. Prod. (2018) in press ; 1 - 7
by Mine Kürkçüoğlu, Hale Gamze Ağalar, Ahmet Aksoy, and Kemal Hüsnü Can Başer
Abstract

The aerial parts of Helichrysum noeanum Boiss. and H. chionophilum Boiss. et Balansa were hydrodistilled for 3 h using a Clevenger-type apparatus. The essential oils were analyzed by GC-FID and GC-MS, simultaneously. The main constituents were identified as hexadecanoic acid (25.3%), dodecanoic acid (17.8%), tetradecanoic acid (13.7%), and decanoic acid (4.2%) for H. noeanum. Decanoic acid (18.7%), tetradecanoic acid (16.9%), dodecanoic acid (13.8%), hexadecanoic acid (12.2%) and hexahydrofarnesyl acetone (3.2%) were found to be the major compounds for H. chionophilum. Several reports have been encountered in the literature dealing with the oil composition of several Helichrysum species. To the best of our knowledge, the essential oil of H. chionophilum has not previously been investigated.

DOI
http://doi.org/10.25135/rnp.93.18.06.113
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Helichrysum noeanum H. chionophilum essential oil GC GC-MS.
Available online: September 20, 2018
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