Records of Natural Products

Articles In Press

Original Article

1) Chemical Composition and Assessment of Antimicrobial, Antioxidant and Antiproliferative Activities of Essential oil from Clinopodium sericeum, a Peruvian Medicinal Plant

Rec. Nat. Prod. (2020) in press ; 1 - 12
by Buc Calderon Pedro , Julio Benites , David Rios , Angélica Guerrero-Castilla , Cinthya Enríquez , Ewaldo Zavala , Roberto O. Ybañez-Julca , Quispe-díaz Ivan and Rafael Jara-Aguilar

Clinopodium sericeum is widely used in Peruvian folk medicine in the form of infusion to treat stomach distress, indigestion and antiflu. In this study, the essential oil from C. sericeum was obtained by hydrodistillation, analyzed by GC and GC/MS, and 73 compounds were identified. Major components of the oil were b-germacrene-D (15%), b-caryophyllene (13.8%), and sabinene (11.2%). Furthermore, we assessed the in vitro biological activities displayed by the oil obtained from the aerial parts of C. sericeum, namely the antioxidant, antimicrobial and antiproliferative activities. The antioxidant activities of the essential oil were evaluated by FRAP, CUPRAC, ABTS and DPPH radical scavenging activity. The essential oil displays antibacterial activity against Gram-negative and Gram-positive bacterial strains (MIC 50-200 µg/mL) in a dose-range close to standard antibiotics. Such activity may be related to the presence of terpene compounds. The antiproliferative activity of the essential oil was measured in vitro using the MTT colorimetric assay in healthy non-tumorigenic cells (HEK-293) and in three human cancer cell lines (T24, DU-145, and MCF-7). The calculated IC50 values were around 0.2 mg/mL. Since the essential oil was almost devoid of antioxidant activity, its anti-proliferative action is unlikely related to oxidative stress and relies on other unknown mechanisms.

DOI
http://doi.org/10.25135/rnp.213.20.10.1845
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Folk medicine Clinopodium sericeum antioxidant antimicrobial antiproliferative cancer cells
Available online: November 17, 2020
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Short Report

2) Composition and Antimicrobial Activity of Essential Oils from Leaves and Twigs of Magnolia hookeri var. longirostrata D.X.Li & R. Z. Zhou and Magnolia insignis Wall. in Ha Giang Province of Vietnam

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Ha Thi Thu Chu , Thuy Thi Thu Dinh , Nam Quang Vu , Tam Kieu Bang Nguyen and William N. Setzer

The essential oils from leaves and twigs of Magnolia hookeri var. longirostrata D.X.Li & R.Z.Zhou and Magnolia insignis Wall., growing wild in Ha Giang Province of Vietnam, were obtained by hydrodistillation and analyzed by gas chromatography-flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS). The respective yields of the M. hookeri var. longirostrata leaf and twig oils were 0.14% and 0.05% (v/w), and of the M. insignis leaf and twig oils were 0.16% and 0.05% (v/w), calculated on a dry weight basis. Major components of the oils of M. hookeri var. longirostrata were: Linalool (21.3%), (E)-nerolidol (12.2%) and neo-intermedeol (13.5%) (leaf oil); 1,8-cineole (13.3%) and linalool (17.1%) (twig oil). Major components of the oils of M. insignis were: Linalool (24.1%), geraniol (14.9%) and (E)-nerolidol (22.5%) (leaf oil); 1,8-cineole (9.5%) and linalool (26.9%) (twig oil). The essential oils from M. insignis showed stronger inhibitory effects on the seven test microorganisms than those from M. hookeri var. longirostrata. Candida albicans and Lactobacillus fermentum were more sensitive to the essential oils than the other tested microorganisms. This is the first time information on essential oils of M. hookeri var. longirostrata leaves and twigs and of M. insignis twigs are reported.

DOI
http://doi.org/10.25135/rnp.212.20.10.1842
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Magnolia hookeri var. longirostrata Magnolia insignis antimicrobial activity essential oil
Available online: November 16, 2020
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Original Article

3) 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

4) 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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Original Article

5) Trimacoside A, a High Molecular Weight Antioxidant Phenylpropanoid Glycoside from Tricyrtis maculata

Rec. Nat. Prod. (2020) in press ; 1 - 8
by Yunze Wang , Wei Zhang , Li Ren , Jing Sun and Dongbo Zhang

Trimacoside A (1), a new phenylpropanoid glycoside, together with nine known compounds (210) was isolated from Tricyrtis maculata. All compounds, except for 8, were firstly isolated from this plant. The structure elucidation of the new compound was carried out by the analysis of spectroscopic data, including 1D, 2D NMR, and HRESIMS. Compounds 1, 4, 5, 7, 8, and 10 showed significant antioxidant activities by DPPH and ABTS assays.

DOI
http://doi.org/10.25135/rnp.209.20.09.1810
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Liliaceae Tricyrtis maculata phenylpropanoid glycoside antioxidant
Available online: October 31, 2020
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Review Article

6) Phytochemistry, Pharmacological Potency, and Potential Toxicity of Myoporum spp.

Rec. Nat. Prod. (2020) in press ; 1 - 21
by Arafa Musa

Abstract:  Genus Myoporum family Myoporaceae, includes approximately 32 species of woody small trees or shrubs, most of them are native to Australia and surrounding territories. Only certain species have been thoroughly studied and  rich in flavonoids, phenylethanoids, Phenylpropanoids, terpenoids, iridoids, essential oil, and trace alkaloids. The essential oils are characterized by sesquiterpenes type components, either in ketone or alcoholic forms usually combined to a furanoid moiety. Myoporum spp. have been utilized in folk medicine for treatment of various diseases and were used as antidermatitis, antibacterial, antipyretic, anti-pulpitis, antipsychotic, anti-inflammatory, detoxicant, and others. Despite all these benefits, Myoporum spp. must be cautiously employed due to their potential toxicities, which arise from the presence of furanosesquiterpenoid contents, particularly in their essential oil. The toxicity influences liver and can extend to kidney and lung causing injury. The present review aims to explore the phytochemistry, beneficial uses and the toxic potentials of Myoporum spp.

DOI
http://doi.org/10.25135/rnp.208.20.10.1833
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Myoporum Myoporaceae secondary metabolites furanosesquiterpenoids biological activities toxicity
Available online: October 31, 2020
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Short Report

7) Aromatic Rosane-type Diterpenoid with Lipase Inhibitory Effect from Euphorbia ebracteolata and Chemotaxonomic Significance of Diterpenoids

Rec. Nat. Prod. (2020) in press ; 1 - 5
by Jian Zhou , Jinhua Wen , Jianhua Huang , Pengfei Chen , Xiao-Chi Ma , Rongjing Sun and Chao Wang

The phytochemical investigation has been performed for Euphorbia ebracteolata, the roots of which are usually used natural medicine in traditional Chinese medicine for the treatments of tuberculosis and bacterial infection. A diterpenoid has been obtained using silica gel and ODS column chromatography. Furthermore, on the basis of widely spectroscopic data analyses, including 1D-, 2D-NMR, HR-ESIMS and ECD, the isolated compound was determined to be a rosane type diterpenoid, which possessed a rare aromatic ring. The isolated diterpenoid as a new compound was named ebraphenol E (1). The bioactivity of isolated diterpenoid (1) has been evaluated and moderate inhibitory effect on lipase (IC50 = 12.5 μM) was observed. In combination with our previous phytochemical investigations about E. ebracteolata, the chemotaxonomic significance of diterpenoids was summarized for E. ebracteolata.

DOI
http://doi.org/10.25135/rnp.204.20.08.1774
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Euphorbia ebracteolata rosane diterpenoid ebraphenol E lipase Chemotaxonomy
Available online: October 28, 2020
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Original Article

8) Three New Polyketides from the Insect-Associated Fungus Letendraea sp. 5XNZ4-2

Rec. Nat. Prod. (2020) in press ; 1 - 7
by Yan Xu , Nanyan Fu , Wanjing Ding , Pinmei Wang and Jinzhong Xu

Chemical investigation of the EtOAc extract of an insect-associated fungus Letendraea sp. 5XNZ4-2 cultured in Potato Dextrose Broth (1/2 PDB) medium lead to the isolation of three new polyketides, named letendronol D (1), phomopsiketones H-I (2-3). The structures of new compounds were elucidated by the analysis of HRESIMS and NMR spectroscopic data, and the absolute configurations were determined by modified Mosher’s method, ECD calculation and single-crystal X-ray diffraction. Cytotoxicity and antibacterial activities of 1 were assayed and regrettably 1 didn’t display any cytotoxicity and antibacterial activity. 3 was the first phomopsiketone derivative obtaining the lactone.

DOI
http://doi.org/10.25135/rnp.206.20.08.1786
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
polyketides insect-associated fungus Letendraea sp.
Available online: October 27, 2020
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Short Report

9) A New Angular Naphthopyrone from Crinoid Colobometra perspinosa

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Hsu-ming Chung , Ling-tsung Hsiao , Zong-you Li and Zhi-hong Wen

A chemical investigation was carried out on a crinoid Colobometra perspinosa collected from Hengchun Peninsula in the South China Sea, which led to the isolation of five angular naphthopyrones (15), including one new metabolite, 8-hydroxy-5,6,10-trimethoxy-2-pentyl-4H-naphtho[1,2-b]pyran-4-one (1). Their structures were assigned based on spectroscopic methods, including UV, HRESIMS, 1D- and 2D-NMR spectra. The anti-inflammatory activity of the isolated compounds was evaluated and compound 5 was found to inhibit the accumulation of the pro-inflammatory iNOS protein in LPS-stimulated RAW264.7 macrophages.

DOI
http://doi.org/10.25135/rnp.207.20.07.1757
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
angular naphthopyrone crinoid Colobometra perspinosa iNOS
Available online: October 20, 2020
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Original Article

10) Antiradical Aromatic Constituents from Pleurotus eryngii

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Jun Sheng Zhang , Xin-xin Cao , Jin-yue Sun , Hua Zhang and Chao Liu

Six aromatic compounds including a new (Z)-ferulic acid ester (1) and a new syringic acid ester (2), as well as four known ferulic acid esters (36), were isolated from a well-known edible mushroom, Pleurotus eryngii. Structures of these aromatics were unambiguously characterized via spectroscopic methods especially MS and NMR techniques. All the isolates were assessed for their antiradical effect and NO production inhibitory activity in RAW264.7 macrophages, and compounds 1 and 3 displayed mild DPPH radical removing activity, with IC50 values of 25.0 and 21.6 mM, respectively.

DOI
http://doi.org/10.25135/rnp.205.20.08.1789
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Pleurotus eryngii aromatics ferulic acid ester syringic acid ester antiradical
Available online: October 19, 2020
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Short Report

11) 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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Short Report

12) Computational Study and Biological Evaluation of Isolated Saponins from the Fruits of Gleditsia aquatica and Gleditsia caspica

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Ehab Ragab , Usama Shaheen , Ammar Bader , Khaled Elokely and Mohammed Ghoneim

Phytochemical study of the ethanolic extract of the fruits of Gleditsia aquatica and Gleditsia caspica resulted in the isolation of the triterpene saponins; aquaticasaponin A (1), aquaticasaponin B (2), caspicaoside L (3) and caspicaoside M (4).  Compound (1) showed good activity against methicillin resistant Staphylococcus aureus (MRSA) (IC50 =16.3 μg/mL) and Staphylococcus aureus (non-MRSA), (IC50 =12.2 μg/mL) and it expressed considerable cytotoxic activity against BT-549 (Human Ductal Carcinoma, Breast), KB (Human Epidermal Carcinoma, Oral) and SK-MEL (Human Malignant Melanoma) with IC50 values of 8.3, 10.0 and 3.3 μg/mL, respectively. Compounds (2) and (3) showed potent cytotoxicity against BT-549 with IC50 values of 5.3 and 7.3 μg/mL, and against SK-MEL with IC50 values of 4.3 and 3.1 μg/mL, respectively. Compound (4) showed good cytotoxicity against KB with IC50 value of 7.3 μg/mL. In consistent, the study of molecular determinates of cytotoxic activity of these new scaffolds showed close high docking scores to CD81 (Cluster of Differentiation 81) human antigen which could be of great importance for the development of new cytotoxic candidates. The structure identification of isolated metabolites was carried out using 1D and 2D NMR  and mass spectra.

DOI
http://doi.org/10.25135/rnp.202.20.08.1764
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Triterpenoidal saponins cytotoxicity CD81 human antigen computational study MRSA
Available online: October 18, 2020
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Original Article

13) Chemical Investigation of a Co-Culture of Aspergillus fumigatus D and Fusarium oxysporum R1

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Ronglu Yu , Mingzhu Li , Yi Wang , Xuelian Bai , Jianwei Chen , Xingnuo Li , Hong Wang and Huawei Zhang

Chemical investigation of a co-culture of two endophytic fungi Aspergillus fumigatus D and Fusarium oxysporum R1 from two traditional medicinal plants, Edgeworthia chrysantha Lindl. and Rumex madaio Makino, led to isolation of a new amide 1 and six known compounds, including neovasinin (2), neovasifuranone B (3), N-(2-phenylethyl)acetamide (4), α-linolenic acid (5), α-elaeostearic acid (6), palmitoleic acid (7). On the basis of extensive spectroscopic analysis including 1D and 2D NMR, HR-ESI-MS and optical rotation measurement as well as comparison of literature data, chemical structure of 1 was unambiguous elucidated as (S, E)-methyl-2-(2,4-dimethylhex-2-enamido)acetate. Bioassay results indicated that none of these compounds exhibited strong inhibitory effect on three human pathogens Escherichia coli, Staphyloccocus aureus and Candida albicans with MIC values of ≥25 μM.

DOI
http://doi.org/10.25135/rnp.199.20.07.1728
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Endophytic fungus Aspergillus fumigatus D Fusarium oxysporum R1 co-culture amide antimicrobial effect
Available online: October 17, 2020
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Short Report

14) Novel Pharmacological Effects of Syringin on Anxiety Behavior and Autonomic Nervous System Activity

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Shouhei Miyazaki , Hirotaka Oikawa , Hideo Takekoshi , Masako Hoshizaki , Masato Ogata and Takahiko Fujikawa

Acanthopanax senticosus HARMS (ASH), a traditional Chinese herbal medicine, has been used to treat arthralgi, muscle weakness of the lower body, hypertension, and impotence. ASH was also reported to increase resistance to stress and fatigue. Recently, the efficacy of ASH against depression and stress-induced gastric ulcer was demonstrated in a rodent model. Previously, we also reported that ASH exerted anxiolytic effects and modulated autonomic nervous system activity under stress. However, no research has examined the anxiolytic effects of isofraxidin and syringin, two constituents of ASH. Thus, we investigated the anxiolytic constituents of ASH. The rats were administered distilled water, isofraxidin or syringin for 1 week. Autonomic nervous system activity was estimated using heart rate variability and anxiety behavior in the improved elevated beam walking (IEBW) test. The syringin increased the time spent in the open arm in the IEBW test. The syringin blocked the significant decrease in normalized high-frequency power, indicative of parasympathetic nervous system activity, in the IEBW test. The isofraxidin exerted no significant effects on behavior and autonomic nervous system activity. These results indicated that syringin partially contributes to the anxiolytic and autonomic nervous system-modulating effects of ASH.

DOI
http://doi.org/10.25135/rnp.200.20.08.1775
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Acanthopanax senticosus isofraxidin syringin anxiolytics autonomic nervous
Available online: September 26, 2020
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Original Article

15) Isolation, Characterization and Antiproliferative Activity of Secondary Metabolites from Tanacetum alyssifolium (Bornm.) Grierson

Rec. Nat. Prod. (2020) in press ; 1 - 8
by Ekrem Köksal , Yakup Ulutaş , Samed Şimşek , Taha Bayraktar , Ahmet Altay , Mustafa Çatır , İbrahim Demirtaş , Ali Rıza Tüfekçi , Ali Kandemir , Cemalettin Alp , Mohammed B. Anwer Alemdar and Hüseyin Akşit

Secondary metabolites of Tanacetum alyssifolium (Bornm.) Grierson (Asteraceae) were investigated for the first time. Thirteen compounds including axillarin (1), Luteolin-7-O-β-glucoside (8) and rutin (13) as flavonoids, fraxetin (7), isofraxidin (9), isofraxidin-7-O-glucoside (11) and fraxidin (12) as coumarins, tatridin A (2), altissin (3), tamirin (4) and tanachin (5) as sesquiterpene lactones and 2,4-dihydroxy-6-methoxy acetophenone (6) and picein (10) as acetophenone derivatives were isolated from the methanol extract of the species. The structures of all isolated compounds were elucidated by 1D and 2D-NMR techniques and by comparing with the literature data. In addition, in vitro cytotoxic activity of all isolated compounds was evaluated against breast cancer MCF-7 cell line by XTT assay. Sesquiterpene lactones; tatridin A (2), tamirin (4) and tanachin (5) were found to be the most cytotoxic molecules against MCF-7 cell line.

DOI
http://doi.org/10.25135/rnp.201.20.07.1702
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Tanacetum alyssifolium sesquiterpene lactones cytotoxicity MCF-7 cell line
Available online: September 26, 2020
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Original Article

16) Essential Oils of Three Hypericum Species from Colombia: Chemical Composition, Insecticidal and Repellent Activity Against Sitophilus zeamais Motsch. (Coleoptera: Curculionidae)

Rec. Nat. Prod. (2020) in press ; 1 - 11
by William Ramiro Patiño Bayona , Erika Plazas , Jenifer Jhoana Bustos Cortes , Juliet Angélica Prieto Rodríguez and Oscar Javier Patiño Ladino

The maize weevil (Sitophilus zeamais) is one of the main insect responsible of significant losses in stored products,  and  to keep nutritional value of them to find  effective and safe solutions are very important. The Hypericum genus might be a potential source of new bio-insecticides due to the chemical composition of essential oils.  In this study, components of  essential oils of three Hypericum species were investigated for first time by Gas Chromatography-Mass Spectrometry (GC-MS) and, fumigant and contact toxicities as well as the repellent activity of essential oils of them were evaluated against S. zeamais adults. While the main components in H. mexicanum oil were determined as  n-nonane (53.08%) and α-pinene (25.28%), the major constituents  were determined as α-pinene (45.52%) and β-caryophyllene (13.59%) in the essential oil of H. myricariifolium. Chemical composition of  essential oil of H. juniperinum were found to be n-nonane (12.0%), α-pinene (8.25%), geranyl acetate (7.93%), and β-caryophyllene (13.60%). The results revealed that H. mexicanum and H. myricariifolium oils have fumigant toxicity (LC50 < 500 µL/L air) and a potential action as repellents (RP > 70% at 6.2–22.7 μL/L air) for the control of the pest.

DOI
http://doi.org/10.25135/rnp.192.20.05.1665
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Sitophilus zeamais essential oil repellent Hypericum mexicanum Hypericum myricariifolium Hypericum juniperinum
Available online: September 14, 2020
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Original Article

17) A New Cynaropicrin Derivative from Cynara Scolymus L.

Rec. Nat. Prod. (2020) in press ; 1 - 8
by Ghada Abbas , Amal Sallam , Fatma M. Abdel Bar , Mohamed Farid Lahloub and Ahmed Gohar

A new sesquiterpene lactone 1a along with other four known compounds 1b, 2, 3 and 4 were isolated from fresh leaves of Cynara scolymus L. using ordinary chromatographic techniques. The structures of the isolated compounds were determined via spectroscopic analysis.

DOI
http://doi.org/10.25135/rnp.198.20.07.1747
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Cynara scolymus sesquiterpene lactones dihydrocynaropicrin etrahydrocynaropicrin pinoresinol luteolin
Available online: September 08, 2020
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Original Article

18) Chemical Constituents of Tibetan Herbal Medicine Pulicaria insignis and Their in vitro Cytotoxic Activities

Rec. Nat. Prod. (2020) in press ; 1 - 12
by Xinzhu Wang , Peilei Hou , Yanbo Qu , Rizhen Huang , Yan Feng , Shifeng Zhao , Yelin Ding and Zhixin Liao

Abstract:  One new phenolic derivative, 1-(4',5'-dihydroxy-2'-methylphenyl)-pentane-1,4-dione (1), along with eighteen known compounds including eight sesquiterpenoids (29), one triterpenoid (10), one bisdpoxylignan (11), one coumarin (12),  and seven flavonoids (1319) were isolated from the dried inflorescence of Tibetan herbal medicine Pulicaria insignis. The structure of 1 was established by spectroscopic methods, including HRESIMS, IR, 1D, and 2D NMR. All isolates were assessed for the cytotoxic activities against MGC-803, T24, HepG2, and HeLa cell lines using the MTT assay. The results showed that compound 1 displayed moderate cytotoxicity against Hela and HepG2, and compounds 3, 4, 5, 6, and 13 exhibited potential cytotoxic activities against the four cell lines with IC50 values ranging from 3.05 to 14.37 μM. Notably, compound 5 exhibited significant anti-proliferative activities against HepG2 cell lines with the IC50 values of 3.05 ± 0.36 μM. Further bioactivity investigation showed that compound 5 could block HepG2 cells in the G1 phase of the cell cycle, thereby inhibiting the growth of HepG2 cells and inducing apoptosis in HepG2 cells.

DOI
http://doi.org/10.25135/rnp.193.20.06.1692
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Pulicaria insignis chemical constituent phenolic derivative cytotoxic activity sesquiterpenoid
Available online: August 24, 2020
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Original Article

19) Identification and Structural Characterization of Anti-Endoplasmic Reticulum Stress Compounds from Ageratum conyzoides (L.)

Rec. Nat. Prod. (2020) in press ; 1 - 9
by Tran Duy Binh , Ryo Kusunoki , Thanh Q. C. Nguyen , Ako Nakagami , Kenji Kanaori , Yen D. H. Nguyen , Tuan L. A. Pham , Cuong C. Nguyen , Le Van Vang and Kaeko Kamei

Ageratum conyzoides is an herbaceous plant widely used in traditional medicine against various diseases, and possesses anti-inflammatory, anti-ulcer, analgesic, and diuretic properties. However, its effects on endoplasmic reticulum (ER) stress, as observed in diseases such as diabetes, have not yet been characterized. In this study, using mouse pancreatic Beta-cells, we demonstrated that the ethanol extract of A. conyzoides effectively suppressed cell death induced by ER stress. Four polymethoxyflavones (PMFs) including (1) 5,6,7,3′,4′,5′- hexamethoxyflavone; (2) 5,6,7,8,3′,4′-hexamethoxyflavone (nobiletin); (3) 3′,4′-methylenedioxy-5′,5,6,7- tetramethoxyflavone; and (4) 5,6,7,8,5′-pentamethoxy-3′,4′-methylenedioxyflavone were isolated from the ethyl acetate fraction using reverse-phase chromatography. Their structures were elucidated using spectroscopic and mass-spectrometric analyses including 1D-, 2D-NMR, and HRESI-MS. All compounds were further evaluated for their ability to inhibit ER stress. Our results suggested that only compound 1 did not show an ability to rescue ER stress-induced cell death. Additionally, compound 2 as a nobiletin and its commercial product alleviated the tunicamycin-dependent chop mRNA expression induction. Notably, extremely low concentrations of both compounds exerted cytoprotective activity against tunicamycin-induced ER stress in pancreatic Beta-cells

DOI
http://doi.org/10.25135/rnp.194.20.06.1697
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Ageratum conyzoides anti-endoplasmic reticulum stress pancreatic-cells nobiletin
Available online: August 24, 2020
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Original Article

20) A New Alkaloid Glycoside from the Stems of Zanthoxylum dissitum Hemsl.

Rec. Nat. Prod. (2020) in press ; 1 - 6
by Xian Wei , Yang Tan , Yuhe Shi , Yuan Yuan and Shunmin Li

A new alkaloid glycoside (1) and six known alkaloids (27) were isolated from the stems of Zanthoxylum dissitum Hemsl.. The structure of compound 1 was resolved by spectrum data, including MS, IR, UV, and MS. All compounds obtained in this research were evaluated for their inhibitions against NO release from LPS-activated RAW264.7 macrophages. Compounds 1-3, 6 and 7 showed significant inhibition activities with IC50 values of 26.12±0.81, 8.41±0.23, 13.75±0.54, 6.97±0.77, and 5.78±0.42 μM, respectively.

 

DOI
http://doi.org/10.25135/rnp.191.20.05.1643
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Zanthoxylum dissitum Hemsl. alkaloid macrophages NO
Available online: July 30, 2020
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© ACG Publications. All rights reserved.