Records of Natural Products

Articles In Press

Original Article

1) Jatroidaine A, A New Tetranortirucallane Type Triterpene from Jatropha multifida

Rec. Nat. Prod. (2021) in press ; 1 - 6
by Fei Li , Liang Ma , Jinyuan Zhang , Xueling Qiao , Dingshan Zhang and Dongbo Zhang

Jatroidaine A (1), a new tetranortirucallane-type triterpene, and two known analogues (23) were isolated from the leaves and branches of Jatropha multifida. Their structures were fully elucidated by extensive spectroscopic methods and comparison to known compounds. The absolute configuration of 1 was assigned by single-crystal X-ray diffraction analysis. All compounds were evaluated for their anti-inflammatory and thioredoxin reductase (TrxR) inhibitory activities. Unfortunately, no significant activity was observed.

DOI
http://doi.org/10.25135/rnp.233.21.02.1968
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Jatropha multifida tirucallane triterpene anti-inflammatory activity thioredoxin reductase
Available online: April 06, 2021
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Original Article

2) New Selective Human MAO-B Inhibitors from the Stems of Erythrina corallodendron L.

Rec. Nat. Prod. (2021) in press ; 1 - 12
by Mohammed Aboelmagd , Khaled M. Elokely , Ataa Said , Eman Haggag , Mohammed Ghoneim and Samir Ross

One new, 10, 11-dioxo-6,7α-erythraline epoxide (A1) and four known erythrinan alkaloids 10, 11-dioxo-erythraline (A2), erysodine (A3), 8-oxo-erythraline (A4) and erythraline (A5) were isolated from the 70% methanolic extract of stems of E. Corallodendron (Fabaceae). The isolated compounds were elucidated by exploiting 1D/2D NMR, and HR-ESI-MS analysis. The absolute configuration of A1 was determined by electronic circular dichroism (ECD). Mono Amine Oxidase inhibitory activity of the isolated alkaloids was investigated in vitro using kynuramine deamination assay on recombinant human MAO-A and B enzymes. The binding modes were predicted by molecular docking and the structure activity relationships of erythrinans were then evaluated. All isolated alkaloids demonstrated preferential activity against MAO-B. A1 displayed the highest potency and selectivity against MAO-B with IC50 of 25.18 μM, (SI >3.97). The selective inhibition exhibited by erythrinan alkaloids against MAO-B is in line with the expected biological impact of Erythrina in the treatment of neurodegenerative diseases and presents this chemical class as promising leads for managing AD and PD diseases.

DOI
http://doi.org/10.25135/rnp.229.21.01.1940
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Erythrina corallodendron alkaloids Alzheimer’s disease Parkinson’s disease selective MAO-B inhibitors docking
Available online: March 14, 2021
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Original Article

3) Isolation and Characterization of Glycosidic Tyrosinase Inhibitors from Typhonium giganteum Rhizomes

Rec. Nat. Prod. (2021) in press ; 1 - 8
by Penghua Shu , Huiqing Zhu , Wanrong Liu , Lingxiang Zhang , Junping Li , Mengzhu Yu , Yingying Fei , Shujing Cai , Ruihua Li , Xialan Wei , Wenhan Yi and Fugang Xiao

A new hydrocinnamoyl glucoside, 1-O-(4-hydroxyhydrocinnamoyl)-β-D-glucopyranose (1), together with fifteen known glycosides, including two phenylethanoid glycosides (23), two cinnamoyl glycosides (45), six phenolic glycosides (611), one lignan glycoside (12) and four megastigmane glycosides (1316) were isolated from a 95% EtOH extract of the Typhonium giganteum rhizomes. The sixteen glycosides were structurally characterized by NMR, HRESIMS, enzymatic hydrolysis and comparison with literature. Upon evaluating inhibitory activities of compounds 116 against mushroom tyrosinase at 25 μM, compounds 10 and 11 exhibited obvious inhibitory activities, with %inhibition values of 20.94±0.59%, 23.28±1.09%, respectively, with arbutin used as the positive control (26.21±0.58%).

DOI
http://doi.org/10.25135/rnp.230.21.02.1965
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Typhonium giganteum tyrosinase inhibitor glycoside arbutin
Available online: March 13, 2021
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Original Article

4) Dicentrine and Dicentrinone Isolated from Stephania tetrandrae Radix Suppress HepG2 Proliferation through Inhibiting PDI Activity

Rec. Nat. Prod. (2021) in press ; 1 - 12
by Mojiao Zhao , Chao Zhang , Dong Zhang , Siyu Zhu , Tianjiao Liu , Zhiwei Li , Dafang Zhang and Yong Yang

Inhibition of protein disulfide isomerase (PDI) has been attempted as a promising anti-cancer strategy. However, there is still no currently available PDI inhibitors approved for clinical use. Here, we isolated seven high yield alkaloids from Stephaniae tetrandrae Radix (STR), a medical herb frequently prescribed in anti-tumor condition, and  identified two potent natural PDI inhibitors, dicentrine and dicentrinone. Among the seven alkaloids isolated, dicentrinone (1), dicentrine (2), tetrandrine (4), and fangchinoline (5) could significantly reduce cell viability in a dosage dependent manner detected by MTT assay in human hepatoma cells. To examine whether the candidate compounds are potent PDI inhibitors, we performed insulin turbidity assay and found dicentrine and dicentrinone, but not tetrandrine  and fangchinoline, could effectively inhibit PDI activity, with IC50 of 56.70 μM and 43.95 μM  respectively. Meanwhile, dicentrine and dicentrinone failed to further reduce the cell number index when co-treated with siRNA of PDI, suggesting the compounds behave as PDI inhibitors. Furthermore, dicentrinone and dicentrine have been successfully docked to the active pocket of PDI (PDB #3UEM) by molecular docking, suggesting the existence of physical interaction between compounds and PDI. Our results suggested that dicentrine and dicentrinone may be developed into safe PDI inhibitors.

DOI
http://doi.org/10.25135/rnp.231.21.01.1929
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Stephania tetrandrae Radix Dicentrine Dicentrinone HepG2 PDI
Available online: March 12, 2021
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Original Article

5) A New Cyclic Tetrapeptide from Endophytic Fungus Aspergillus versicolor E-2

Rec. Nat. Prod. (2021) in press ; 1 - 5
by Miao Dong , Yanjun Chen , Kejun He , Yi-jian Chen , Yanqing Ye and Min Zhou

A new cyclic tetrapeptide (1) named aspergilpeptide A, together with a known cyclic tetrapeptide penicopeptide A (2) and chaetominine (3) were obtained from the endophytic fungus Aspergillus versicolor E-2 isolated from the medicinal plant Euphorbia royleana. The structures of compounds (1-3) were elucidated using NMR and MS methods.

DOI
http://doi.org/10.25135/rnp.225.21.01.1931
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Cyclic tetrapeptide endophytic fungus Aspergillus versicolor
Available online: March 07, 2021
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Original Article

6) Coumarins from Angelica dahurica and Their Antitumor Activities in Human MG-63 Osteosarcoma Cells

Rec. Nat. Prod. (2021) in press ; 1 - 7
by Weizhen Chen , Guokai Wang , Ke Mei and Jianyong Zhu

A new coumarin, angedahurin A (1), and seven known analogues (28), were isolated from the roots of Angelica dahurica. Their structures were identified by extensive NMR, IR, and HR-ESIMS spectroscopic analyses. The cytotoxicities of coumarins 18 against MG-63 human osteosarcoma cell lines were screened. Compound 1 showed significant cytotoxic effects against MG-63 with an IC50 value of 7.2 uM,for comparison, the positive control, 5-FU, had an IC50 value of 32.4 uM. Morphological features of apoptosis activities were evaluated in 1-induced MG-63 cells and the results confirmed MG-63 cell apoptosis in a dose-dependent manner.

DOI
http://doi.org/10.25135/rnp.225.21.01.1935
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Angelica dahurica coumarin apoptosis cytotoxicity
Available online: March 07, 2021
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Short Report

7) Cyclic Polyketides with α-Glucosidase Inhibitory Activity from Endiandra kingiana Gamble and Molecular Docking Study

Rec. Nat. Prod. (2021) in press ; 1 - 6
by Mohamad Nurul Azmi Mohamad Taib , Nur Amirah Saad , Mohamad Hafizi Abu Bakar , Mohammad Tasyriq Che Omar , Ahmad Nazif Aziz , Habibah A. Wahab , Sadia Siddiq , M. Iqbal Choudhary , Marc Litaudon and Khalijah Awang

A phytochemical investigation of the methanolic extract of Endiandra kingiana (bark) led to the isolation of four major compounds which are kingianic acid A (1), tsangibeilin B (2), kingianin A (3) and kingianin F (4). The structures were determined by 1D- and 2D-NMR analysis in combination with HRMS experiments. The compounds were screened for their in vitro α-glucosidase inhibition activity. Among them, compounds 3-4 showed potent α-glucosidase inhibition activity with IC50 value at 11.9 ± 2.0 µM and 19.7 ± 1.5 µM, respectively. The molecular docking study found that both compounds were bound into the active site of the N-terminal of MGAM, and thus agreed with the in vitro α-glucosidase enzyme inhibition activity results.

DOI
http://doi.org/10.25135/rnp.227.20.11.1889
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Endiandra kingiana cyclic polyketides Endiandric acids kingianins α-glucosidase inhibition molecular docking
Available online: March 02, 2021
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Original Article

8) Understanding Radix Angelica sinensis Blood Replenishing mechanisms on Blood Deficiency Rats Based on a UPLC-Q/TOF-MS Metabolomics and Network Pharmacology

Rec. Nat. Prod. (2021) in press ; 1 - 14
by Xiujuan Yang , Yi Deng , Zhijun Yang , Shuo Li , Yunxiang Hai and Yihong Tian

Radix Angelica sinensis (RAS) is a famous Chinese medicine with hematinic effects and has been applied for the treatment of blood deficiency syndrome for many years. Previous studies have indicated that RAS has beneficial effects in the treatment of hemolytic anemia. The hemolytic anemia/blood deficiency syndrome is a common syndrome that is often presented in most traditional Chinese medicine (TCM) clinics. Based on routine blood indicators, metabolomics analysis was conducted to investigate the mechanism of RAS in the treatment of hemolytic anemia. Multivariate and univariate statistical analysis were used to identify potential biomarkers in the serum. On administering RAS to the haemololitic anaemic rat, the levels of WBC, RBC, HGB, and PLT in AG tended to shift toward that of the control group. Additionally, all the 26 metabolites such as cholic acid, succinic acid and orotate which are regulated by blood deficiency appeared normal through the five metabolic pathways, such as linoleic acid metabolism, alanine, aspartic acid and glutamate metabolism, pyrimidine metabolism, arginine and proline metabolism. Thus, three metabolic pathways predicted by the network pharmacology were consistent with the metabolism pathway of Angelica sinensis: linoleic acid metabolism, arginine and proline metabolism, tryptophan metabolism. The integrated metabolomics and network pharmacology comprehensively improved the understanding of the physiological and metabolic state of an organism. The possible hematopoietic effects and underlying mechanism of action on hemolytic anemia rats after lavage with RAS water extracts, could potentially be elucidated by combining pharmacology with untargeted metabolomics. These pointed out the significance of metabolomics as a valuable tool for studying the essence of Chinese medicine’s syndrome theory and the mechanism of RAS under anti-blood deficiency syndrome.

DOI
http://doi.org/10.25135/rnp.224.21.01.1950
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Angelica Sinensis replenishing blood effect UPLC-Q/TOF-MS metabolomics network pharmacology
Available online: March 02, 2021
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Original Article

9) Metabolic Correlations of Salvia dugesii Fernald and Salvia gesneriiflora Lindl. & Paxton with Native Salvia Plants from Four Continents Using Essential Oils Compositions

Rec. Nat. Prod. (2021) in press ; 1 - 13
by Mónica A. Calderón-Oropeza , Ernesto Ramírez-Briones , Gabriela Rodríguez-García , José L. Salvador-Hernández , Brenda Y. Bedolla-García , Sergio Zamudio , Luis D. Maldonado-Bonilla , Rosa E. Del Río and Mario A. Gómez-Hurtado

Several applications of natural products around the world arise from traditional knowledge or evident organoleptic properties, and essential oils from Salvia species are a current example. The genus is integrated by native and endemic species from Africa, the Americas, Asia, and Europe. In the present work, essential oil compositions of Salvia dugesii and S. gesneriiflora were experimentally determined and statistically correlated with ten described Salvia species from four continents by using multivariate methods complemented with univariate analysis and PCA protocols, to establish metabolic approaches. Essential oils data from S. angulata, S. miltiorrhiza, S. plebeia, S. sclarea, S. argentea, S. viridis, S. lavandulifolia, S. africana-lutea, S. chamelaeagnea, and S. officinalis were included in the study. By the above, 146 essential oil components, classified into 29 structural skeletons, according to its biogenesis, were analyzed. The results provided metabolic similarities between American and Asian Salvia species due to a higher active sesquiterpene metabolism; and African and European species revealed chemical similarities, since monoterpene pathways dominate. Such correlations are in concordance with genetic knowledge about genus, thereby, approaches on metabolism of Salvia can be easily visualized using statistical tools, consequently, practical method to analyze Salvias for scientific proposes.

DOI
http://doi.org/10.25135/rnp.223-19.121912
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Salvia Salvia dugesii Salvia gesneriiflora Lamiaceae essential oil metabolism chemometric analysis
Available online: February 14, 2021
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Review Article

10) Evidence-Based Medicinal Potential and Possible Role of Selaginella in the Prevention of Modern Chronic Diseases: Ethnopharmacological and Ethnobotanical Perspective

Rec. Nat. Prod. (2021) in press ; 1 - 26
by Mohd Adnan , Arif Jamal Siddiqui , Arshad Jamal , Walid Sabri Hamadou , Amir Mahgoub Awadelkareem , Manojkumar Sachidanandan and Mitesh Patel

Different species of the genus Selaginella are exploited for various ethnomedicinal purposes around the globe; mainly to cure fever, jaundice, hepatic disorders, cardiac diseases, cirrhosis, diarrhea, cholecystitis, sore throat, cough of lungs, promotes blood circulation, removes blood stasis and stops external bleeding after trauma and separation of the umbilical cord. Though, high content of various phytochemicals has been isolated from Selaginella species, flavonoids have been recognized as the most active component in the genus. Crude extract and different bioactive compounds of this plant have revealed various in vitro bioactivities such as, antimicrobial, antiviral, anti-diabetic, anti-mutagenic, anti-inflammatory, anti-nociceptive, anti-spasmodic, anticancer and anti-Alzheimer. However, more studies into the pharmacological activities are needed, since none of the professed bioactivity of this plant have ever been fully evaluated. Therefore, this review aims to discuss the evidence-based ethnomedicinal and ethnopharmacological uses, phytochemicals and bioactive potential of Selaginella species. It will provide an updated knowledge for ethnobotanists, ethnopharmacologists and other scientific communities to rethink over the possible usage of Selaginella in medicine. Moreover, further explorations are needed to formulate a novel medicinal product from Selaginella extracts for the improvement of human health, together with toxicity evaluations, necessary to ensure about the safety of these medicinal lycophytes.

DOI
http://doi.org/10.25135/rnp.222.20.11.1890
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Selaginella chronic diseases anti-Alzheimer anti-diabetic ethnobotany phytochemistry
Available online: February 07, 2021
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Short Report

11) Eudesmane Sesquiterpenoids from Salvia plebeia

Rec. Nat. Prod. (2021) in press ; 1 - 4
by Ying Lu and Yifang Chen

A new eudesmane sesquiterpene (1), named sapleudesone, together with four known analogs (25) were isolated from the aerial parts of Salvia plebeia. The structure of compound 1 was established by NMR and HRESIMS data, and the absolute configuration of 1 was determined by comparing the experimental ECD spectrum with the calculated ECD spectra. The known compounds were identified to be salplebeone A (2), linderolide I (3), chlorantene D (4), and chlomultin B (5) by comparing the NMR data and specific rotations with reported data. All five compounds were tested for the inhibitory effects against NO production in LPS-activated RAW 264.7 macrophages, As a result, compound 2 exhibited weak inhibitory effects with an IC50 value of 42.3  1.4 uM.

DOI
http://doi.org/10.25135/rnp.218.20.10.1856
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
eudesmane sesquiterpene Salvia plebeia; NO production inhibitory effects
Available online: January 01, 2021
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Original Article

12) Volatile Constituents of Cistanche tubulosa and Their Antioxidant and Antimicrobial Potentials

Rec. Nat. Prod. (2021) in press ; 1 - 11
by Arafa Musa , Khaled F. El-massry , Ahmed H. El-ghorab , Amr Farouk , Hazim M. Ali , Mohamed A. Abdelgawad , Ibrahim A. Naguib and Ehab M. Mostafa

Abstract: Abstract: The hydrodistilled volatile constituents of Cistanche tubulosa (commonly known as Desert Ginseng) have been chemically and biologically investigated. Based on the retention times and mass fragmentation of the obtained GC-MS chromatogram, 106 individual components which representing ≈ 99.29 % of the total volatile constituents have been identified. The major compounds (66.57% of the total composition) were identified as hexanal (15.98%), trans-sabinyl acetate (12.22%), allo-aromadendrene (9.30%), nonanoic acid (6.66%), 3Z- hexeny-2-methyl butanoate (6.09%), valeranone (5.25%), (E, E)-α-Farnesene (3.18%), a-pinene (3.06%), linalool isovalerate (3.03%) and a-humulene (1.8%). Estimation of the antioxidant activity of EO showed promising effect at 80 mg/mL concentration, it exerted 62.40, 863.29 and 62.72 % inhibition compared to TBHQ that showed 78.62, 77.56 and 79.23 % inhibition using DPPH, ABTS and β-carotene/Linoleic acid, respectively. The antioxidant activity was pronounced at 80 mg/mL than other concentrations. The volatile constituents showed inhibitory activity against gram positive bacteria ranged from 2.23 mg/100 mL ( for staphylococcus aureus ), and  15.68 mg/100 mL (for Bacillus cereus) compared to ciprofloxacin which showed inhibitory activity 0.185, and 0.182 mg/100 mL, respectively. Moreover, the MIC of volatiles towards gram negative bacteria are ranged from 18.35 (Escherichia coli) to 31.61 mg/100 mL (Klebsiella pneumonia) compared to ciprofloxacin with 0.184 to 0.188 mg/mL respectively. Additionally, the antifungal activity against candida albicans was rather promising (4.36 mg/mL).

DOI
http://doi.org/10.25135/rnp.220.20.11.1859
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Cistanche tubulosa volatile constituents antioxidant antimicrobial Orobanchaceae
Available online: January 01, 2021
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Review Article

13) Silybum marianum: not just Silymarin and Flavonolignans

Rec. Nat. Prod. (2020) in press ; 1 - 11
by Maria Giordano , Giovanni Luongo , Sergio Davinelli , Afef Ladhari , Giuseppina Rita Nappo and Maddalena Giordano

The use of Silybum marianum L. for therapeutic purposes has been known since ancient times. Its phytocomplex reduces transaminases and other biohumoral indices in the course of liver disease and also in hepato-renal syndrome. In particular, the flavonolignan component has shown properties that would partially explain the ability of the phytocomplex to induce a certain regeneration of liver cells, stimulate the cellular elimination of toxins and reduce the inflammatory component, present in fatty, alcoholic and hormonal therapies with steroids. S. marianum is also successfully used in the treatment of patients with symptomatic chronic hepatitis, with complete disappearance of clinical symptoms, such as asthenia, loss of appetite, severe meteorism, dyspepsia, and with normalization of transaminases. The same results can be obtained in patients undergoing heavy chemotherapy cycles. Modern herbal medicine uses it in decoction or infusion, however with some caution in patients suffering from hypertension, due to the presence of tyramine. In addition, the extracts of the roots have antioxidant, diuretic and febrifugal properties and those of the leaves have aperitif properties. It is therefore interesting to provide a picture of the different non-flavonolignanic components (terpenes, steroids and essential oils) of the plant and their properties, which have perhaps been wrongly neglected over the past few years.

DOI
http://doi.org/10.25135/rnp.219.20.09.1827
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Silybum marianum silibinin terpenes steroids biological activity
Available online: December 26, 2020
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Short Report

14) Chemical Composition, and Evaluation of Antibacterial,Antibiofilm and Synergistic Effects with Conventional Antibiotics of Essential Oil from Mallotus repandus

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Pengxiang Lai , Xin-Chen Zhang , Lin Zhu , Xin-Yu Li and Li-Chuan Liu

The essential oil (EO) of aerial parts of Mallotus repandus (Willd.) Muell. Arg. was extracted by hydrodistillation and characterized by GC/FID and GC/MS. Fifty-one compounds comprising 97.1% of the EO were identified, of which α-humulene  (18.7%), β-selinene (12.8%), aciphyllene (10.7%), (E)-caryophyllene (8.4%), α-copaene (5.5%), humulene epoxide II (4.9%) and caryophyllene oxide (4.3%) were the major compounds. The EO was evaluated for antibacterial properties using broth microdilution method and crystal-violet static biofilm formation assay. The M. repandus EO possessed a bactericidal effect against tested gram-positive bacteria strains (MIC = MBC: 0.05-0.10 mg/mL). Further, the EO showed the ability to inhibit the biofilm formation of Staphylococcus aureus. In addition, the potential synergistic effect was assessed by checkerboard method. Combination of the M. repandus EO with Streptomycin showed synergistic effects against the tested bacterial strains. This study demonstrates that M. repandus EO could be further explored as good alternative for potential pharmaceuticals.

DOI
http://doi.org/10.25135/rnp.217.20.10.1854
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Mallotus repandus (Willd.) Muell. Arg. essential oil antibacterial activity antibiofilm activity synergistic effects
Available online: December 20, 2020
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Original Article

15) New Flavonoids from Saudi collection of Tephrosia purpurea L. (Pers.)

Rec. Nat. Prod. (2020) in press ; 1 - 8
by Maged Abdel-Kader , Mohammed Alqarni and Ahmed Foudah

Phytochemical investigation of the chloroform fraction obtained from Saudi collection of Tephrosia purpurea L. (Pers.) resulted in the isolation of four new and two known flavonoid derivatives. Three of the new compounds were 5-deoxyflavonoid derivatives identified as tephropurpugazanin (1), 4’’-hydroxyapollinin (4), epi-tephroapollin E (5) as well as (-)-tephropurpulin A (2). The known compounds were identified as 3,7-dihydroxy-8-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one (3) and tephroapollin E (6). Structures were elucidated utilizing different spectroscopic tools including UV, optical rotation, 1D- and 2D-NMR as well as HRESIMS.

DOI
http://doi.org/10.25135/rnp.216.20.10.1828
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Tephrosia purpurea isolation structure elucidation 5-deoxyflavonoid
Available online: December 20, 2020
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Original Article

16) Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites

Rec. Nat. Prod. (2020) in press ; 1 - 12
by Danka Bukvicki , Miroslav Novakovic , Tatjana Ilic-Tomic , Jasmina Nikodinovic-Runic , Nina Todorovic , Milan Veljic and Yoshinori Asakawa

Biotransformation of bis-bibenzyl perrottetin F (1), isolated from the liverwort Lunularia cruciata by Aspergillus niger, has been investigated. New metabolites (2-4) have been isolated using reversed phase semipreparative HPLC and their structures were established to be 8-hydroxyperrottetin F, C-7-C-8 cleaved product, and perrottetin F 6’-sulfate using 1D and 2D NMR, HR-ESI-MS, IR and UV spectroscopy. The antimicrobial and cytotoxic properties of these compounds were also evaluated. Given the suggested cytotoxic properties of the parent compound, antiproliferative activity against healthy human lung fibroblasts (MRC5) and human lung carcinoma (A549) of three metabolites were evaluated revealing their lower cytotoxic properties in comparison to the starting compound - perrottetin F. The antimicrobial properties of these compounds were also evaluated, with the inhibitory activity against the Pseudomonas aeruginosa PAO1 and Staphylococcus aureus determined between 100 µM and 450 µM. The metabolites showed remarkable ability to inhibit synthesis of bacterial quorum-sensing signal molecules such as short chain acyl homoserine lactones (AHLs). Therefore, biotransformation method represents fast and effective tool for obtaining new bioactive structures.

DOI
http://doi.org/10.25135/rnp.215.20.09.1812
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Biotransformation; perrottetin F; liverworts; Aspergillus niger; cytotoxic activity; 1D and 2D NMR
Available online: December 17, 2020
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Original Article

17) A New Phenylpropanoid from the Roots of Solanum melongena L. and Evaluation of Anti-inflammatory Activity

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Yan Liu , Xin Yin , Yanping Sun , Yuan Liu , Dongxv Lu , Yuanyuan Zhou , Mohammed Algradi Adnan , Juan Pan , Wei Guan , Bingyou Yang and Haixue Kuang

Fifteen phenylpropanoids were isolated from the ethanol extract of the roots of Solanum melongena L., including a new compound, melongenapanoid A (1), together with fourteen known compounds (2-15). Their chemical structures were elucidated by 1D and 2D NMR and HR-MS data according to those values of the literatures. The fourteen known compounds (2-15) were all firstly isolated from this plant. While, the isolates were evaluated for the inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in RAW 264.7 cell line. Compounds 2, 4 and 5 showed moderate inhibition of NO production with IC50 values of 28.7, 24.4 and 32.6 μM, respectively.

DOI
http://doi.org/10.25135/rnp.211.20.10.1837
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Solanum melongena L natural products phenylpropanoids anti-inflammatory activity
Available online: December 05, 2020
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Original Article

18) Isolation, Characterization and Antioxidant, Tyrosinase Inhibitory Activities of Constituents from the Flowers of Cercis glabra ‘Spring-1’

Rec. Nat. Prod. (2020) in press ; 1 - 7
by Penghua Shu , Yamin Li , Yuehui Luo , Shujing Cai , Yingying Fei , Wenhan Yi , Yuan Yang , Xialan Wei , Yuhuan Zhang , Tieyao Tu and Lin Zhang

A phytochemical study on the flowers of Cercis glabra ‘Spring-1’ led to the isolation and identification of twelve compounds, including one new compound named as 1-O-α-l-rhamnosyl-(E)-phytol (1) and eleven known compounds. Their structures were elucidated based on physical data analysis, including HR-ESI-MS, NMR, UV, IR, and acid hydrolysis. All compounds were screened for in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl method. Compounds 4 and 5 exhibited obvious DPPH radical scavenging activities. All the isolates were tested for their inhibitory effects on mushroom tyrosinase, and compounds 6, 7, 10 and 11 showed moderate tyrosinase inhibitory activities. 

DOI
http://doi.org/10.25135/rnp.214.20.10.1851
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Cercis glabra ‘Spring-1’ 1-O-α-l-rhamnosyl-(E)-phytol antioxidant tyrosinase.
Available online: November 27, 2020
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Original Article

19) Antimicrobial, Cytotoxic, Antiviral Effects, and Spectroscopic Characterization of Metabolites Produced by Fusarium oxysporum YP9B

Rec. Nat. Prod. (2020) in press ; 1 - 22
by Nurettin Yaylı , Merve Cora , Hande Sipahi , Rengin Reis , Elif Öztürk , İshak Erik , Arif Bozdeveci , Gonca Çelik , Gözde Kılıç and Sengul Alpay Karaoglu

The goal of the work is to determine the bioactive pharmaceutical metabolites produced by the Fusarium oxysporum YP9B isolate. Ten new natural compounds were isolated from the ethyl acetate extract of the F. oxysporum YP9B strain.  Their structures were elucidated by spectroscopic methods using 1D and 2D NMR, UV, FT-IR, and mass spectra (LC-QTOF MS and GC-FID/MS). Identified compounds were named as; (1-benzyl-2-methoxy-2-oxoethyl)-2-hydroxy-3-methylbutanoate (1), 2-oxo-8-azatricyclo[9.3.1.13,7]-hexadeca-1(15),3(16),4,6,11,13-hexaen-10-one (2), 2,3-dihydroxypropanoic, hexadecanoic anhydride (3a), 2,3-dihydroxypropanoic (9Z)-octadecenoic anhydride (3b), 2,3-dihydroxy-propanoic (9Z,12Z)-octadecadienoic anhydride (3c), 2,3-dihydroxypropanoic (11Z)-octadecenoic anhydride (4a), 2,3-dihydroxypropanoic, (9E,12E)-octadecadienoic anhydride (4b), 3-hydroxy-1,2,6,10-tetramethylundecyl hexzadecanoate (5a), 3-hydroxy-1,2,6,10-tetramethylundecyl (9E)-octadecaenoate (5b),  and 3-hydroxy-1,2,6,10-tetramethylundecyl octadecanoate (5c). Antimicrobial activities of the isolates obtained from the YP9B strain were determined. Cytotoxic and antiviral activities were tested for the isolates against VERO, MCF-7, PC-3, and A549. Compounds 5a-c, 1, and 3a-c showed bacteriostatic activity at low concentrations, and 4a-b and 2 were found to be bactericides. MIC and MBC values against Mycobacterium smegmatis for the compounds 5a-c and 1 were determined to be ​​ <0.5 µg/mL and 0.46 µg/mL, respectively. The experimental result showed that compounds 2, 5a-c and 1 have strong cytotoxic (7.51±1.38 and 19.13± 0.68 (µM) IC50) activity. The antiviral activity against HSV type-1 was determined to be 1.25 µM for compounds 4a-c and 0.312 µM for compound 1.

DOI
http://doi.org/10.25135/rnp.208.20.06.1674
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Fusarium oxysporum YP9B seconder metabolite antimicrobial cytotoxic antiviral
Available online: November 16, 2020
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Review Article

20) Genus Melaleuca - A Review on the Phytochemistry and Pharmacological Activities of the Non-Volatile Components

Rec. Nat. Prod. (2020) in press ; 1 - 24
by Fatma M. Abdel Bar

Plants of the genus Melaleuca which belong to family Myrtaceae, commonly named "tea trees”, are economically important plants. When talking about tea trees, the essential oils are the center of attention, leaving all other phytoconstituents in their shade. Many reviews addressed the composition and pharmacological activities of Melaleuca alternifolia L. essential oil as the most common one. To date, there are no detailed reviews summarizing the phytochemical and pharmacological properties of the non-volatile components of members of the genus Melaleuca. After distillation of the volatile oil, large amounts of these plants’ waste remain untapped. This review indicates that this genus is a rich source of diverse groups of bioactive phytochemicals, including flavonoids, triterpenoids, benzylic phloroglucinol-terpene derivatives, polyphenols, hydrolysable tannins, and other compounds. It also discusses the diverse pharmacological activities reported for plants of this genus.

DOI
http://doi.org/10.25135/rnp.210.20.09.1801
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Melaleuca Myrtaceae tea tree paperbark tree phytochemistry pharmacological activities
Available online: November 10, 2020
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Short Report

21) Benzodiazepine Derivatives from Marine-Derived Streptomyces cacaoi 14CM034

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Semiha Çetinel , Melis Küçüksolak , Ataç Uzel and Erdal Bedir

7-methoxy-8-hydroxy cycloanthranilylproline (2), a new natural product with pyrrolobenzodiazepine (PBD) framework, was isolated from marine-derived actinobacterium Streptomyces cacaoi 14CM034, together with cycloanthranilylproline (1). Structural elucidation of the compounds was based on FTIR, 1D- (1H and 13C NMR), 2D-NMR (COSY, HMBC and NOESY) and HR-MS analyses. Compounds 1 and 2 exhibited notable antimicrobial activity. The presence of PBD derivatives in S. cacaoi was first demonstrated with this study.

DOI
http://doi.org/10.25135/rnp.203.20.08.1766
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Marine actinobacterium Streptomyces cacaoi Benzodiazepine Antimicrobial activity Antibiotics
Available online: October 19, 2020
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