Records of Natural Products

Year: 2019 Volume: 13 Issue:1 January-February

Original Article

1) Phytochemical Changes in Aerial Parts of Hypericum perforatum at Different Harvest Stages

Rec. Nat. Prod. (2019) 13:1 ; 1 - 9
by Ping Sun, Tianlan Kang, Hua Xing, Zhen Zhang, Delong Yang, Jinlin Zhang, Paul W. Paré and Mengfei Li
Abstract

Hypericum perforatum is a perennial herb that produces anti- depression metabolite hypericin (Hyp) as well as flavonoids and poly phenols . In order to find the optimization of harvest stage to increase bioactive compounds production , the levels of Hyp , flavonoids and poly phenols as well as antioxidant capacity were evaluated by the assays of high performance liquid chromatography (HPLC), NaNO 2-AlCl 3-NaOH and Folin-Ciocalteu as well as 1, 1-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP), respectively. The results showed that there was no difference in antioxidant capacity of extracts from aerial parts between floral budding stage (FBS) and blooming stage (BS) , while significant decrease was observed at fruit set stage (FSS) compared to BS (P < 0.05). On a per plant basis, biomass and the levels of Hyp , flavonoids and poly phenols in aerial parts decreased during harvest stages , even if bioactive compounds contents i n flower reache d the highest at BS on a dry weight basis . These findings indicated that the optimization of harvest stage of H. perforatum should be at FBS.

DOI
http://doi.org/10.25135/rnp.77.18.04.267
Keywords
Hypericum perforatum harvest stage hypericin flavonoids poly phenols antioxidant capacity .
DETAILS PDF OF ARTICLE
© 2019 ACG Publications. All rights reserved.
Original Article

2) Antinociceptive Activity of Essential Oils from Wild Growing and Micropropagated Plants of Renealmia alpinia (Rottb.) Maas

Rec. Nat. Prod. (2019) 13:1 ; 10 - 17
by Isabel Gómez-Betancur, Dora Benjumea, Juan E. Gómez, Natalia Mejía and Juan F. León
Abstract

Renealmia alpinia is a medicinal plant that has been cultivated and used for the treatment of headaches, abdominal pain, as a febrifuge and t o treat snake bites in southeast Colombia and in the Caribbean islands. Moreover, its edible fruits are commonly used as spice in Mexico. The R. alpinia leave-extracts have shown enzymatic inhibition of Bothrops atrox and B othrops asper snake poison. The extracts also showed effects as a peripheral analgesic agent. This report investigates the analgesic activity of the essential oils obtained by hydrodistillation from wild and in vitro propagation samples of R. alpinia as well as the chemical profile using GC-MS. The essential oils isolated from R. alpinia evaluated on concentrations of 50, 75 and 100 mg/ k g showed significant antinociceptive effects in the test of acetic-acid-induced abdominal writhing, compared to the control animals. The essential oil of the wild flora leaves showed the highest percentage of pain inhibition by 200 mg/kg , concluding that t he essential oil of R. alpinia presents antinociceptive activity in an in vivo model. These results help us to understand the traditional use of R . a lpinia to treat pain and make it a potential source for the development of phyto pharmaceutics.

DOI
http://doi.org/10.25135/rnp.70.18.01.084
Keywords
Renealmia alpinia essential oil an tinociceptive micropropagation
DETAILS PDF OF ARTICLE
© 2019 ACG Publications. All rights reserved.
Original Article

3) The Chemical Composition and Biological Activity of the Essential Oil from the Underground Parts of Ferula tadshikorum (Apiaceae)

Rec. Nat. Prod. (2019) 13:1 ; 18 - 23
by Farukh S. Sharopov, Payrav D. Khalifaev, Prabodh Satyal, Yanfang Sun, Abduahad Safomuddin, Safol Musozoda, Michael Wink and William N. Setzer
Abstract

The underground parts of Ferula  tadshikorum M. Pimenwere collected from the southern part of Tajikistan. The essential oils were obtained by hydrodistillation and analyzed by GLC-FID and GLC-MS. A total of 26 compounds were identified representing 94.4 % of total oil composition. The essential oil was dominated by the sulfur-containing compounds (Z)-1-propenyl sec-butyl disulfide (37. 3%), (E)-1-propenyl sec-butyl disulfide (29.9%), (E)-1-propenyl 1-(methylthio)propyl disulfide (16.8%), and propyl sec-butyl disulfide (4.8%). The antioxidant, antimicrobial and cytotoxic activities of the essential oil was evaluated. To our best knowledge, this is the first report concerning the chemical composition and biological activity of the essential oil obtained from the underground parts of F.  tadshikorum.

DOI
http://doi.org/10.25135/rnp.65.18.02.089
Keywords
Ferula tadshikorum essential oil composition disulfides
DETAILS PDF OF ARTICLE
© 2019 ACG Publications. All rights reserved.
Original Article

4) Biological Activities of Various Extracts from Salvia cassia Sam. ex Rech.f. and Chemical Composition of Its Most Active Extract

Rec. Nat. Prod. (2019) 13:1 ; 24 - 36
by Burcu Sen Utsukarci, Bahar Gurda, Merve Bilgin, Dilek Satana, Betul Demirci, Nur Tan and Afife Mat
Abstract

This study was conducted on the antibacterial, antimycobacterial and antifungal activities of various extracts (petroleum ether (PE), chloroform (CHCl 3) and ethanol (EtOH) extracts; infusion and decoction) and essential oil from the aerial parts of S. cassia Sam. ex Rech.f. and the chemical composition of the most active samples. The antibacterial activity was determined against Bacillus subtilis, Staphylococcus aureus, methicillin resistant Staphylococcus aureus, Pseudomonas aeruginosa, Enterococcus faecalis, Klebsiella pneumoniae, Proteus mirabilis and Escherichia coli. The antimycobacterial activity was analyzed against five different Mycobacterium tuberculosis and the antifungal activity was compared with two dermotophytes and three Candida species. The composition of EO was analyzed by GC-FID and GC-MS. The EO had a very good activity against B. subtilis (0.3 µL/mL) and good activity against S. aureus, methicillin resistant S. aureus (MRSA) and E. faecalis (0.6 µL/mL). All extracts were active in the antimycobacterial and antifungal tests (MICs=50-400 µg/mL). The EO was the most active samples against all Mycobacterium strains, dermatophytes and Candida species (MICs=0.1-6.25 µL/mL). Because of the high activity of EO, its composition was analyzed, and the major compound was found caryophyllene oxide (22.3%), which was also found the major components of the essential oils from other antimicrobial plants such as Salvia trichoclada Benth.

DOI
http://doi.org/10.25135/rnp.68.18.02.090
Keywords
Salvia cassia antimicrobial antimycobacterial antifungal essential oil caryophyllene oxide
DETAILS PDF OF ARTICLE
© 2019 ACG Publications. All rights reserved.
Original Article

5) HPLC Fingerprint of Important Phenolic Compounds in Some Salvia L. Species from Iran

Rec. Nat. Prod. (2019) 13:1 ; 37 - 49
by Marzieh Fotovvat, Tayebeh Radjabian, and Azra Saboora
Abstract

Salvia L. is a large genus of the Lamiaceae family with high medicinal value. Pharmaceutical properties of Salvia species are mainly due to their secondary metabolites, especially phenolic compounds. This study was focused on identification and determination of five bioactive phenolic compounds (rosmarinic acid, carnosic acid, caffeic acid, salvianolic acids A and B) in the 41 populations from 27 wild Salvia species of Iran using a simple and reliable HPLC-UV method. The principal component analysis (PCA) technique was used to study differentiation among species according to their phenolic compound profiles. Significant intra- and inter-specific variations were observed in the distribution patterns and contents of phenolic compounds in the studied Salvia species. As a result of this study, it was found that leaves had greater amounts of phenolic compounds as compared to the roots. The highest content of rosmarinic acid (41.53±0.88 mg/g DW) and salvianolic acid A (8.10±0.35 mg/g DW) were found in the leaves of S. verticillata. The leaves of S. syriaca and S. sharifii were rich in salvianolic acid B (54.47±2.00 mg/g DW) and carnosic acid (34.05±1.18 mg/g DW), respectively. The PCA results revealed chemical variations in the Salvia species collected from different regions and could fully distinguish between them based on the phenolic compounds concentrations. The present study demonstrated that apart from S. officinalis, some wild species such as S. verticillata, S. hypoleuca, S. leriifolia and S. virgata can be introduced as potent natural sources for medicinal and industrial purposes.

DOI
http://doi.org/10.25135/rnp.72.18.02.228
Keywords
Salvia species rosmarinic acid salvianolic acid A salvianolic acid B carnosic acid HPLC
DETAILS PDF OF ARTICLE
© 2019 ACG Publications. All rights reserved.
Original Article

6) Chemical Characterization and Antioxidant Activity of Mountain Pine (Pinus mugo Turra, Pinaceae) from Republic of Macedonia

Rec. Nat. Prod. (2019) 13:1 ; 50 - 63
by Marija Karapandzova, Gjoshe Stefkov, Ivana Cvetkovikj Karanfilova, Tatjana Kadifkova Panovska, Jasmina Petreska Stanoeva, Marina Stefova and Svetlana Kulevanova
Abstract

Chemical composition and antioxidant activity of essential oils and methanol extracts of needles of Pinus mugo native to R. Macedonia were investigated. Plant material was collected on Karadzica Mountain during two seasons. Essential oil was obtained by steam distillation and was analyzed by GC/FID/MS. 8 major constituents were identified: D 3 -carene, a -pinene, limonene+ b -phellandrene, germacrene D, trans-caryophyllene, d -cadinene, bicyclogermacrene and a -cadinol. Identification of flavonoids and phenolic compounds in methanol extracts was made by LC-DAD/ESI-MS n. 14 compounds were identified (2 phenolic acids, 2 procyanidins, 7 flavonol glycosides and 3 flavonol acylated glycosides). Total phenolic content (TPC) and total flavonoid content (TFC) were measured by Folin-Ciocalteau and aluminum chloride assay, respectively. TPC and TFC values ranged from 11.41-12.17 mgGAE/g and from 4.65-6.03 mgCE/g for dried plant material, respectively. Evaluation of antioxidant activity was made using DPPH and TBARS test. IC 50 values for the methanol extract ranged from 11.58-16.01 mg/mL for DPPH and from 9.41-15.76 mg/mL for TBARS assay. IC 50 values for the essential oil ranged from 2.51-4.26 mg/mL and 2.59-4.14 mg/mL for DPPH and TBARS assay, respectively. The needles from Macedonian P. mugo could be considered as a potential plant source for isolation of essential oil as well as flavonoids and other phenolics as they exhibit promising antioxidant activity. Additionally, f urther investigation and evaluation of chemical composition as well as biological activity should be done in order to provide more data for their possible medicinal, pharmaceutical and commercial utilization.

DOI
http://doi.org/10.25135/rnp.73.18.02.233
Keywords
Essential oil flavonoids GC/FID/MS LC/DAD/ESI-MS n methanol extract Pinus mugo
DETAILS PDF OF ARTICLE
© 2019 ACG Publications. All rights reserved.
Original Article

7) Isolation and Antimicrobial Activity of Rutin and Its Derivatives from Ruta chalepensis (Rutaceae) Growing in Iraq

Rec. Nat. Prod. (2019) 13:1 ; 64 - 70
by Shaymaa Al-Majmaie, Lutfun Nahar, George P. Sharples, Khazal Wadi and Satyajit D. Sarker
Abstract

Rutin (1), rutin 3'-methyl ether (2), and a new flavonol glycoside, 6-hydroxy-rutin 3',7-dimethyl ether (3), were isolated from the methanol extract of the fruits of Ruta chalepensis , collected from Diyala, Iraq. Their structures were elucidated by spectroscopic analyses, including 1D-, 2D-NMR and HR ESI MS. Antimicrobial activity of compounds 1-3 was tested against four Gram +ve and Gram –ve bacterial strains, and the only fungal strain, Candida albicans, using the 96-well based resazurin microtitre assay.

DOI
http://doi.org/10.25135/rnp.74.18.03.250
Keywords
Ruta chalepensis Rutaceae resazurin assay antimicrobial activity rutin 6-hydroxy-rutin 3‵ 7-dimethyl ether
DETAILS PDF OF ARTICLE
© 2019 ACG Publications. All rights reserved.
Original Article

8) Chemical Constituents and Anti-influenza Viral Activity of the Leaves of Vietnamese Plant Elaeocarpus tonkinensis

Rec. Nat. Prod. (2019) 13:1 ; 71 - 80
by Nga Thu Dao, Yejin Jang, Meehyein Kim, Hung Huy Nguyen, Duong Quang Pham, Quang Le Dang, Minh Van Nguyen, Bong-Sik Yun, Quan Minh Pham, Jin-Cheol Kim and Vu Dinh Hoang
Abstract

Various Elaeocarpus species including Elaeocarpus tonkinensis have been important medicinal plants that used in traditional medication system and mainly used to cure nervous system-related disorders. However, their antiviral potential has not been reported yet. During the screening of medicinal plant extracts with the antiviral activity against influenza viruses, we found that E. tonkinensis extract has strong antiviral activity. Through organic solvent partition and repeated column chromatography using SiO 2, C-18 and Sephadex LH-20, a total of nine compounds were purified from the methanol extract of E. tonkinensis. Their chemical structures were determined by NMR and MS spectral data to be trolliamide (1), gallic acid (2), urolithin M-5 (3), hydroquinone (4), 2,4-dihydroxybenzoic acid (5), 3,5-dihydroxy-4-methoxybenzoic acid (6), corilagin (7), chebulagic acid (8), and shikimic acid (9). Their antiviral activity against influenza virus strains A/Puerto Rico/8/34 (H1N1; PR8), A/Hong Kong/8/68 (H3N2; HK) and B/Lee/40 (Lee) was examined on the basis of cytopathic effect (CPE) assay. Among them, compounds 2, 3, 4, 7, and 8 significantly inhibited viral replication in a dose-dependent manner with EC 50 values ranging from 7.8 to 59.6 μg/mL against influenza A and/or B viruses with selectivity indices above 5.0. This study suggests that the botanical materials of E. tonkinensis could be promising inhibitors of influenza A andB viruses and applied to the development of a novel herbal medicine.

DOI
http://doi.org/10.25135/rnp.76.18.04.266
Keywords
Influenza virus Elaeocarpus tonkinensi antiviral activity infectious disease
DETAILS PDF OF ARTICLE
© 2019 ACG Publications. All rights reserved.
Short Report

9) Investigation of Insect Repellent Activity of Cyclocolorenone Obtained from the Red Alga Laurencia intricata

Rec. Nat. Prod. (2019) 13:1 ; 81 - 84
by Takahiro Ishii, Yuto Shinjo, Miyu Miyagi, Hiroshi Matsuura, Tsuyoshi Abe, Norio Kikuchi and Minoru Suzuki
Abstract

Three known secondary metabolites were isolated from the organic extract of Laurencia intricata. Their structures were identified by NMR and MS experiments and comparison with the literature data. An aromadendrane sesquiterpene, (+)-cyclocolorenone showed strong repellent activity against the maize weevil Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae) adults. It had the same activity as natural insecticides, pyrethrins, with a ED 50 value of 2.0 m g/cm 2. This is the first report of insect repellent activity of (+)-cyclocolorenone. The results suggest that the red alga Laurencia is a promising source of bioactive compounds which can be used as potential biocontrol agents for stored-product insects.

DOI
http://doi.org/10.25135/rnp.66.18.02.221
Keywords
Cyclocolorenone insect repellent activity Sitophilus zeamais Laurencia intricata
DETAILS PDF OF ARTICLE
© 2019 ACG Publications. All rights reserved.
Short Report

10) Chemical Composition and Antihypertensive Effect of Phoenix roebelenii Using Angiotensin Converting Enzyme inhibition invitro and in vivo

Rec. Nat. Prod. (2019) 13:1 ; 85 - 90
by Karina S. Schumacker, Andrews Marques Nascimento, Anna Paula Rampazzo , Dominik Lenz, Helber Barcellos da Costa, Wanderson Romão, Rodrigo Scherer, Tadeu Uggere Andrade and Denise Coutinho Endringer
Abstract

This study aimed to evaluate in vivo anti-hypertensive effect of Phoenix roebelenii. To access the chemical composition, the EtOH extract and CH2Cl2 fraction of P. roebelenii were analyzed using electrospray ionization (ESI) source combined with the Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS) technique. The ACE inhibitory effect was evaluated in vivo by Ang I administration. The antihypertensive assay was performed in Spontaneously Hypertensive Rats (SHR) and Wistar rats that were treated with enalapril (10 mg/kg), CH2Cl2 fraction (80 mg/kg; twice a day) or vehicle for 30 days. ACE activity in vivo was measured by colorimetric assay. ESI(-)FT-ICR mass spectrum for EtOH extract identified the presence of rutin, quercitrin, kaempferol-7-O-glucoside and kaempferol-3-O-rutenoside, and in the CH2Cl2 fraction, paradol, gingerol, ursolic/betulinic acid and maslinic/corosolic acid. CH2Cl2 fraction exhibited anti-hypertensive effect in vivo by reducing blood pressure in the SHR models. It may be concluded that the presence pungent vanilloids compounds in CH2Cl2 fraction contributed to the ACE inhibition in vitro and in vivo and that action could be the mechanism of the anti-hypertensive effect, known for its medicinal value

DOI
http://doi.org/10.25135/rnp.75.18.02.238
Keywords
Keywords:Phoenix roebelenii phoenix palm. angiotensin converting enzyme gingerol.
DETAILS PDF OF ARTICLE
© 2019 ACG Publications. All rights reserved.
Short Report

11) Chemical Composition, Antibacterial and Antioxidant Activities of Essential oil from Leonurus pseudomacranthus Kitag

Rec. Nat. Prod. (2019) 13:1 ; 91 - 95
by Ling-Jing Mao , Xiao-Yu Xie, Yang Gao , Peng-Xiang Lai and Qing-lin Ma
Abstract

This study investigated the chemical composition and in vitro antibacterial and antioxidant activities of the essential oil obtained by hydrodistillation from the aerial parts ofLeonurus pseudomacranthus Kitag for the first time. The chemical composition was studied by GC-FID and GC-MS. Forty-nine compounds accounting for 91.1% of the essential oil were identified. The major components were s clareol (34.8%), β- c aryophyllene (7.1%), p recocene (I) (6.3%) and α- m uurolene (5.3%). The antibacterial activity of the essential oil was assessed by the disc diffusion and microdilution methods. The essential oil showed excellent antibacterial activity against Bacillus subtilis and Staphylococcus aureus with MIC values of 0.039 mg/mL and 0.156 mg/mL, respectively. Moreover, the antioxidant potential was evaluated by DPPH, ABTS and FRAP assays. The essential oil gave IC 50 values of 1.5 13 mg/mL, 0.1 52 mg/mL in DPPH and ABTS methods, and a Trolox equivalent concentration of 33.63 μmol Trolox × g -1 in FRAP method. The results indicated that the essential oil could be regarded as a promising product for pharmaceutical and food industry after more detailed study.

DOI
http://doi.org/10.25135/rnp.83.18.03.098
Keywords
Leonurus pseudomacranthus Kitag essential oil antibacterial activity antioxidant activity.
DETAILS PDF OF ARTICLE
© 2019 ACG Publications. All rights reserved.
Erratum

12) Erratum to “ Headspace Analysis of Volatile Compounds Coupled to Chemometrics in Leaves from the Magnoliaceae Family

Rec. Nat. Prod. (2019) 13:1 ; 96 - 96
by Mohamed A. Farag, Riham Salah El Din and Sherifa Fahmy
Abstract

In the published paper affiliations for coauthors Riham S. El Din & and Sherifa Fahmy is given a wrong number 2 and to be thus affiliated to Center for Regulatory and Environmental Analytical Metabolomics, Department of Chemistry, University of Louisville 2320 S. Brook St., Louisville and should be 1 to Pharmacognosy Department, College of Pharmacy, Kasr El-Aini St, Cairo University, Egypt. T he authors apologize for this error and their affiliation number changed as 1

DOI
http://doi.org/10.25135/rnp.88.18.07.325
Keywords
Magnoliaceae
DETAILS PDF OF ARTICLE
© 2019 ACG Publications. All rights reserved.