Records of Natural Products

Articles In Press

Short Report

1) Antioxidants and α-Glucosidase Inhibitors from Lactuca serriola L.

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Nouran H. Abdel Fatah , Yhiya Amen , Fatma M. Abdel Bar , Ahmed F. Halim and Hassan-Elrady A. Saad

Our main objective in the present study was to search for bioactive compounds of potential antidiabetic and antioxidant activities from the methanol extract of Lactuca serriola L. aerial parts for the prevention and treatment of diabetes. Phytochemical investigation allowed the isolation of 17 known compounds identified based on various spectroscopic techniques as lupeol (1), β-sitosterol (2), taraxast-20-ene-3β,20-diol (3), glycerol monopalmitate (4) (2S,3S,4R,2`R,14E)-2-(2`-hydroxytetracosanoylamino)-14-octadecene-1,3,4-triol (5), lactucopicrin (6), daucosterol (7), (E)-p-coumaric acid (8), 11β,13-dihydrolactucin (9), 4-hydroxybenzoic acid (10), protocatechuic acid (11), kaempferol (12), quercetin (13), lactuside A (14), luteolin-7-O-β-D glucoside (15), lactuside B (16) and cichorioside B (17). The antioxidant activity was evaluated using ABTS, DPPH radical scavenging assays and FRAP assay. The ethyl acetate fraction showed remarkable α-glucosidase inhibitory activity (IC50, 9.16±0.17 µg/mL) and antioxidant activity among the tested fractions. The in vitro α-glucosidase inhibitory assay is reported in this study for the first time for L. serriola L. The results strongly suggest that L. serriola L. can be used as a potential good natural remedy targeting oxidative stress-related diabetes mellitus.

DOI
http://doi.org/10.25135/rnp.189.2005.1647
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Asteraceae Lactuca serriola antioxidant α-glucosidase inhibitors
Available online: July 03, 2020
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Short Report

2) Aromatic Compounds from the Marine-Derived Fungus Aspergillus versicolor

Rec. Nat. Prod. (2020) in press ; 1 - 5
by Rong Yao , Shen Yao and Ailian Hua

Chemical investigation of the EtOAc extract of a marine-derived fungus Aspergillus versicolor SZW-5 led to the isolation of one new compound, named aspeverether A (1), and seven known compounds. The structures were determined by extensive analyses of spectroscopic data (1D and 2D NMR, and HRESIMS). Compounds 1 and 3 possessed an unusual 1,3-dimethoxy-2-vinylbenzene moiety, which is rarely found in nature. Compound 6 showed strong inhibitory effect toward a-glucosidase with an IC50 value of 71 mM, being more active than the positive acarbose (210 mM).

DOI
http://doi.org/10.25135/rnp.188.20.05.1664
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Aspergillus versicolor aspeverether A structure elucidation marine
Available online: June 28, 2020
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Original Article

3) Protective Effects of Origanum onites Essential Oil in the Methotrexate-Induced Rat Model: Role on Apoptosis and Hepatoxicity

Rec. Nat. Prod. (2020) in press ; 1 - 10
by Asli Aykac , Eda Becer , Dilek Özbeyli , Göksel Şener and Kemal Hüsnü Can Başer

Methotrexate (MTX) is an effective cytotoxic agent which is used to treat malignancies and inflammatory diseases. Origanum onites (O. onites) is found throughout the Eastern Mediterranean region and has been used in traditional medicine. The essential oils (EOs) of O. onites rich in highly bioactive phytochemicals such as carvacrol (CVR) and has antiviral, antioxidant, anticancer and proapoptotic properties. The aim of this study was to investigate the protective effects of CVR and O. onites-EO treatment in MTX-induced hepatorenal toxic rats' liver and kidney tissues. The bcl-2/bax ratio, glutathione (GSH) level, malondialdehyde (MDA) level, and myeloperoxidase (MPO) activity of liver and kidney tissues were evaluated in the MTX-induced rat model. Results showed that the administration of CVR or O. onites-EO significantly increased bcl-2/bax expression and GSH levels as well as reduced MDA level and MPO activity in the kidney and liver tissues of MTX-induced rat model. In conclusion, our results suggest that O. onites-EO and CVR have protective effect in MTX-induced hepatorenal toxic rats' liver and kidney tissues by decreasing oxidative stress and apoptosis.

DOI
http://doi.org/10.25135/rnp.186.20.04.1631
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Methotrexate Origanum onites essential oil hepatorenal toxicity
Available online: June 16, 2020
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Original Article

4) The Leaf and the Gall Volatiles of Salvia fruticosa Miller from Turkey: Chemical Composition and Biological Activities

Rec. Nat. Prod. (2020) in press ; 1 - 15
by Sevda Süzgeç Selçuk , Temel Ozek , Gulmira Özek , Süleyman Yur , Fatih Göger , Bahar Gürdal , Gizem Gülsoy Toplan , Ali H. Meriçli and Kemal .H. Can Baser

In this study two different extraction techniques namely, conventional hydrodistillation (HD) and micro-steam distillation-solid-phase microextraction (MSD-SPME), were used to analyze the volatile constituents from the leaves and the galls of Salvia fruticosa Mill. by gas chromatography (GC-FID) and gas chromatography coupled to mass spectrometry (GC-MS). The oxygenated monoterpenes (62.4-69.3%) were found to be predominating compound group with 1,8-cineole and camphor as the main constituents in all the tested samples with the exception of the gall oil in which oxygenated sesquiterpenes (25.6%) and diterpenes (17.3%) were detected in high percentages. Qualitative differences of the volatiles obtained by HD and MSD-SPME techniques from the leaf and the galls are discussed. The resulting leaf essential oils were evaluated for their in vitro acetylcholinesterase (AChE) inhibition potential. In vitro DPPH scavenging, and Cupric Reducing Antioxidant Capacity (CUPRAC) assays were used to evaluate the leaf essential oils. AChE inhibition 41.2% and antioxidant 36.8% assays results showed moderate levels of activity. In this present study, to the best of our knowledge comparative leaf and gall volatiles of S. fruticosa was reported for first time.

DOI
http://doi.org/10.25135/rnp.185.20.03.1579
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Salvia fruticosa galls acetylcholinesterase antioxidant SPME GC-MS
Available online: June 15, 2020
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Original Article

5) A New Lignan Glycoside from the Roots of Silene tatarinowii Regel

Rec. Nat. Prod. (2020) in press ; 1 - 5
by Xiaofei Liang , Yuze Li , Yuwen Cui , Zhuofei Liang , Wenli Huang , Yi Jiang , Huawei Zhang and Xiaomei Song

A new lignan glycoside, siletatoside A (1), and three known lignans, (+)-isolariciresinol (2), balanophonin (3), and (+)-lariciresinol (4), were isolated from the roots of Silene tatarinowii Regel. Compounds 2–4 were isolated from the Silene genus for the first time. Their structures were determined based on physicochemical properties and spectroscopic methods. The structure of siletatoside A was elucidated for the first time. The cytotoxicity of 1–4 was evaluated in vitro in human HCT116, HT29, A549, and H1299 tumor cell lines. These compounds displayed weak cytotoxicity in the human cancer cell lines. 

DOI
http://doi.org/10.25135/rnp.187.20.01.1529
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Silene tatarinowii lignan siletatoside A cytotoxicity
Available online: June 15, 2020
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Original Article

6) Overexpression of Global Regulator LaeA Induced Secondary Metabolite Production in Aspergillus versicolor 0312

Rec. Nat. Prod. (2020) in press ; 1 - 8
by Ting He , Yudan Wang , Lianqiong Du , Fangru Li , Qiufen Hu , Guiguang Cheng and Weiguang Wang

This experiment investigated the effect of the global regulator laeA on the secondary metabolites of Aspergillus versicolor. The laeA gene was cloned from Aspergillus versicolor 0312 to introduce pSilent I overexpression vector, and the recombinant plasmid was introduced into Aspergillus versicolor 0312 by PEG guided protoplast transformation. Then, the over-expressing strain 0312-laeA was screened and verified by metabolic level and gene level. A new compound versicolor A (1) was obtained by liquid fermentation of the over-expressing strain, together with four known compounds, acetylapoaranotin (2), acetylaranotin (3), diisobutyl phthalate (4) and ergosterol (5). The structure of the new compound was elucidated by using various spectroscopic techniques inclusive of HRESIMS, 1D- and 2D-NMR data. Compound 1 showed cytotoxicity against MOLT-4 cell lines with IC50 values of 29.6 µM, while 2 showed significant cytotoxicities against MOLT-4, MCF-7, and CaCo-2 cell lines with IC50 values of 7.8, 19.9, and 15.9 µM, respectively. The results further supported that laeA is a global regulator that could up-regulate and/or activate cryptic gene clusters to produce new secondary metabolites. This study provides an important basis for exploring the mechanism of laeA gene on the secondary metabolites of Aspergillus versicolor.

DOI
http://doi.org/10.25135/rnp.183.20.03.1593
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Natural products Aspergillus versicolor LaeA biosynthetic gene clusters secondary metabolites
Available online: June 14, 2020
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Original Article

7) Salvianolic Acid B Attenuated Ischemia/Reperfusion-Induced Brain Injury in Mice by Inhibiting Reactive Oxygen Species-Mediated Inflammation

Rec. Nat. Prod. (2020) in press ; 1 - 10
by Chiyeon Lim , Chang-Hyun Kim , Se-Hyun Lim and Suin Cho

Salvianolic acid B (SAB) is one of main components of the dried roots and rhizomes of Salvia miltiorrhiza Bunge (RSM), which is widely used as a medicinal herb in East-Asia. According to traditional Korean medicine, RSM promotes blood flow, and thus, we investigated the effects of administering SAB after ischemia/reperfusion (I/R)-induced brain injury in a mouse model. I/R-induced brain injury was induced by middle cerebral artery occlusion (MCAO) for 2 h. SAB was orally administered to mice twice after 3 and 6 h of occlusion at 5, 15, or 45 mg/kg body weight. Administration of SAB at 45 mg/kg significantly reduced infarct volumes and edema indices and suppressed interleukin 1 beta (IL-1β), tumor necrosis factor alpha (TNF-α), and reactive oxygen species (ROS) levels in brain ipsilateral hemispheres. SAB also down-regulated Mn-SOD protein expression in affected brain tissues after I/R-induced brain injury. Our results indicate the neuro-protective effects of salvianolic acid B are due to its anti-inflammatory effect mediated by intra-cellular superoxide scavenging..

DOI
http://doi.org/10.25135/rnp.184.20.03.1573
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Salvianolic acid B Salvia miltiorrhiza ischemia/reperfusion injuryi nflammationb rain edema
Available online: May 27, 2020
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Short Report

8) A New Diarylbenzophenone from Selaginella tamariscina

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Wanling Chen , Yujie Peng , Wanxia Huang , Lu Zhou , Xinyu Quan , Qiong Zhao , Dan Zhang , Xifeng Sheng , Yixiao Luo and Hui Zou

A new diarylbenzophenone, namely selagibenzophenone C (1), along with 1,3-di-p-hydroxyphenyl-4-penten-1-one, (2) and unciflavone E (3) were isolated from Selaginella tamariscina. Their structures were elucidated on the basis of spectroscopic and mass spectrometric analyses, including 1D-, 2D-NMR and HRESIMS. Compound 1 represents the first example of naturally occurring diarylbenzophenone. Compound 2 was firstly isolated from the genus of Selaginella.

DOI
http://doi.org/10.25135/rnp.182.20.03.1586
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Selaginella Selaginella tamariscina diarylbenzophenone selagibenzophenone C norlignan
Available online: May 09, 2020
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Short Report

9) Two New Bibenzyl Compounds from Dendrobium lindleyi

Rec. Nat. Prod. (2020) in press ; 1 - 5
by Zhimei Shang , Xiaofei Li and Shiji Xiao

Two new bibenzyl compounds 4,4',5-trihydroxy-3,3',α-trimethoxybibenzyl (1) and 4,5-dihydroxy-3, 3',4',α-tetramethoxybibenzyl (2), along with seven known compounds (39), were isolated from the methanol extract of the whole parts of Dendrobium lindleyi. The chemical structures were established on the basis of spectroscopic analysis including one and two-dimensional NMR spectroscopy and comparison with previously reported data.

DOI
http://doi.org/10.25135/rnp.181.20.02.1557
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Orchidaceae Dendrobium lindleyi Bibenzyl compound
Available online: May 09, 2020
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Original Article

10) Chemical Constituents of the Seeds of Pharbitis purpurea and Laxative Effect of Methyl Caffeate on Rats

Rec. Nat. Prod. (2020) in press ; 1 - 9
by Fenqin Zhao , Yahui Yan , Jiawei Li , Yizhu Dong , Jin Xie , Ruyue Chen and Hui Yang

The chemical constituents of the seeds of Pharbitis purpurea belonging to the Convolvulaceae family were studied. The anti-tumor activities of all isolated compounds on A549 and HepG2 tumor cell lines and effect of methyl caffeate (8) on intestinal excretion in rats were also studied. Fourteen compounds were isolated from the seeds of P. purpurea by column chromatography using silica gel, ODS, Sephadex LH-20 and HPLC. Their structures were determined by 1D and 2D NMR and HRMS. They were identified as (2S,3S)-5-[(1E)-2-carboxyethenyl]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-3-benzofurancarboxylic acid dimethyl ester (1), 8-epiblechnic acid (2), dimethyl (1R,2S)-6,7-dihydroxy-l-(3,4-dihydroxy)-phenyl-1,2-dihydronaphthalene-2,3-dicarboxylate (3), dimethyl 6,9,10-trihydroxybenzo[kl]xanthene-1,2-dicarboxylate (4), syringaresinol-4’-O-β-D-glucopyranoside (5), (+)-syringaresinol (6), (+)-pinoresinol (7), methyl caffeate (8), ethyl caffeate (9), osmanthuside J (10), methyl 6β,7β,16β,17-tetrahydroxy ent-kauran-18-oate (11), β-sitosterol (12), 1-O-linoleoyl-glycol (13) and 1-O-linoleoyl-glycerol (14). Compounds 1 and 3 are new natural products. 4 is reported from the family Convolvulaceae for the first time and 8, 10 and 11 from P. purpurea for the first time. Methyl caffeate (8), 10 and 30 mg/kg, significantly promote intestinal peristalsis in rats. Methyl caffeate (8) has no acute toxicity to rats at 5000 mg/kg.

DOI
http://doi.org/10.25135/rnp.178.19.12.1508
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Pharbitis purpurea chemical constituents promoting intestinal peristalsis methyl caffeate
Available online: May 09, 2020
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Short Report

11) Chemical Constituents of Gymnosporia stylosa and Their Anti-inflammatory Activity

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Dang Thach Tran , Phi Hung Nguyen , Manh Hung Tran , Phuong Dai Nguyen Nguyen , Truong Nhan Ngu , Thi Huyen Thoa Pham and Dao Cuong To

A new flavanone glycoside, gymnosporioside (1), and three known compounds (2-4) were isolated from the leaves of Gymnosporia stylosa. The structure of gymnosporioside (1) was determined by nuclear magnetic resonance (NMR), time-of-flight mass spectrometry (TOFMS), and circular dichroism (CD) spectral data. The known compounds were identified as prunin (2), acteoside (3), and isoacteoside (4), by comparing the NMR data from this study with those reported in the literature. These known compounds, 2-4, have not been previously isolated from G. stylosa. Their anti-inflammatory activities were evaluated against lipopolysaccharides (LPS)-induced activation of nitric oxide (NO) production in RAW264.7 cells, in vitro. Compounds 3 and 4 showed significant inhibitory activities against LPS-induced NO production in RAW264.7 cells, with IC50 values of 17.8 ± 0.4 and 19.3 ± 0.3 mM, respectively.

DOI
http://doi.org/10.25135/rnp.179.20.03.1578
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Gymnosporia stylosa Celastraceae Flavanone Anti-inflammatory
Available online: May 02, 2020
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