Records of Natural Products

Year: 2018 Volume: 12 Issue:5 September-October

Review Article

1) Management of Tobacco Mosaic Virus through Natural Metabolites

Rec. Nat. Prod. (2018) 12:5 ; 403 - 415
by Waqar Islam , Muhammad Qasim, Ali Noman, Muhammad Tayyab, Shiman Chen and Liande Wang

The viruses are one of the most threatening factors for plants resulting in gigantic economic losses. These utilize host internal machinery for reproduction and can spread through biological and non-biological means. Among the most hazardous plant viruses, Tobacco mosaic virus (TMV) is the most ancient virus which causes massive economic losses to tobacco, pepper, cucumber and ornamental crops globally. The problem can be reduced by minimizing the vector population through application of pesticides. Opposite to obtained success in virus control, rapid utilization of synthetic chemicals is disastrous for our ecosystem. Therefore, alternative approaches such as natural derivatives should be explored for eco-friendly management of TMV. So, here we have tried to take into account various natural metabolites which can be effectively and potentially used against TMV. We further explained about the derivatives from animals, fungi, bacteria and actinomycetes which are useful against TMV. The review imbibes the recent research findings regarding exploration of natural derivatives for management of TMV and concludes through highlighting the future prospects via hoping that future pesticides will be safer for human being and our planet.

DOI
http://doi.org/10.25135/rnp.49.17.10.178
Keywords
Hyperoxaluria propolis verapamil antioxidant crystal deposition
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© 2018 ACG Publications. All rights reserved.
Original Article

2) Evaluation of Cytotoxic Activity in vitro of Charantin A Extracted from Momordica charantia

Rec. Nat. Prod. (2018) 12:5 ; 416 - 425
by Zijun Guo, Guocai Wang, Maoxin Zhang, Guangwen Liang, Qiang Li and Bing Ling

Charantins A is cucurbitane-type triterpene glycoside secondary metabolites derived from Momordica charantia . Here, biological activities of charantin A and mode of action to Spodoptera litura ovary cell line ( SpLi-221) were evaluated. We investigated the effects of charantins A on cell growth inhibition compared with charantins B, momordicin I and azadirachtin A. Among them, charantins A showed the most potent activity against SpLi-221 cells with the lowest IC 50 values, and in a time- and dose-dependent manner. Moreover, the cell morphology changed after charantin A treatment, including cytoplasm leakage, irregular morphology, and apoptotic bodies. In addition, the flow cytometry assay confirmed that charantin A promoted the occurrence of cells’ G2/M block and apoptosis, as evidenced by an increased ratio of cells in the sub-G1 phase. Furthermore, cell membrane disruption and increase of intracellular calcium levels were observed following charantin A treatment. These findings provide new clues regarding the role of cucurbitane-type triterpene glycosides as potential novel pesticides for pest control.

DOI
http://doi.org/10.25135/rnp.61.17.12.190
Keywords
Momordica charantia tetracyclic triterpene cytotoxicity cell cycle calcium homeostasis Spodoptera litura
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© 2018 ACG Publications. All rights reserved.
Original Article

3) Composition of the Essential Oil of Salvia montbretii Benth. from Turkey

Rec. Nat. Prod. (2018) 12:5 ; 426 - 431
by Fatma Abak, Gulsum Yildiz, Vagif Atamov and Mine Kurkcuoglu

The composition of the essential oil produced from aerial parts of Salvia montbretii Benth.(Lamiaceae), was analyzed by GC and GC-MS. Forty-six compounds constituting about 97.7% of the essential oil were characterized.The main compounds were characterized as b -caryophyllene (32.8%), b -pinene (9.8%), a -humulene (8.2%), 12-hydroxy- b -caryophyllene acetate (6.6%), germacrene D (4.9%) and a -pinene (4.5%).

DOI
http://doi.org/10.25135/rnp.51.17.12.080
Keywords
Salvia montbretii Benth oil composition b -caryophyllene a -humulene b -pinene.
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© 2018 ACG Publications. All rights reserved.
Original Article

4) Evaluation of the Anti-Gout Potential of Calluna vulgaris L. (Ericaceae) in Rats

Rec. Nat. Prod. (2018) 12:5 ; 432 - 444
by Oliviu Vostinaru, Elena Dinte, Maria Loredana Soran, Ildiko Lung, Ocsana Opris and Cristina Mogosan

The present study evaluated the anti-gout potential of an ethanolic extract from Calluna vulgaris L. Hull (ECV). A preliminary phytochemical analysis of ECV was performed by spectrophotometric and HPLC-PDA-MS methods. Hypouricemic effect of ECV was tested in vivo using the oxonate-induced hyperuricemia model in rats, systolic blood pressure being also monitored in hyperuricemic animals. The anti-inflammatory and analgesic effects of ECV were investigated by the carrageenan-induced paw oedema and Randall-Selitto test in rats. The results of the phytochemical analysis of the extract obtained from C. vulgaris showed the main chemical constituents were flavonoids and chlorogenic acid. ECV showed significant and dose-dependent hypouricemic effects in oxonate-treated rats, increasing the urinary excretion of uric acid. The tested extract produced statistically significant anti-inflammatory and analgesic effects at the dose of 500 mg/kg. This study offers a new perspective regarding the anti-gout potential of C. vulgaris.

DOI
http://doi.org/10.25135/rnp.71.18.03.253
Keywords
Calluna vulgaris L. flavonoids chlorogenic acid hypouricemic
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© 2018 ACG Publications. All rights reserved.
Original Article

5) Anatolian Propolis Prevents Oxalate Kidney Stones: Dramatic Reduction of Crystal Deposition in Ethylene-Glycol-Induced Rat Model

Rec. Nat. Prod. (2018) 12:5 ; 445 - 459
by Fehmi Narter, Ayça Diren, Alper Kafkaslı, Allison P. Eronat, M. Fatih Seyhan, Hülya Yılmaz-Aydoğan, Sukran Sarıkaya, Seda Damla Hatipoğlu, Kemal Sarıca and Oguz Ozturk

One of the many properties of propolis, a gift of nature, is that it is a potent antioxidant agent, which has been shown to be a miracle-worker in many different diseases. In this study, its possible protective and reversing effects against hiperoxaluria was investigated in a rat model in comparison with verapamil. In all 5 groups (Total n=76), aside from the control, hiperoxaluria was induced with continuous ethylene glycol (EG) administration. The others received EG only, 50 mg/kg propolis, 100 mg/kg propolis and 1mg/kg verapamil. To estimate the antioxidant/oxidant status in the tissue and serum samples, catalase (CAT), superoxide dismutase (SOD), total glutathione (GSH), nitric oxide (NO), malonyl dialdehyde (MDA) and total anti-oxidant capacity (T-AOC) were measured after 7 and 28 days. In the early phase, serum T-AOC levels were significantly elevated in the EG+P100 (p=0.0062) compared to the control, while in the late phase, it was elevated in the EG+P50 (p=0.037) and EG+V (p=0.009) compared to the EG only group. Propolis administration was observed to dramatically decrease crystal deposition (p<0.0001) and was more effective in the prevention of oxalate-induced renal injury than verapamil. Propolis being a natural product with almost none adverse effects elevates its value as a future approach to urolithiasis.

DOI
http://doi.org/10.25135/rnp.48.17.11.075
Keywords
Hyperoxaluria propolis verapamil antioxidant crystal deposition
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© 2018 ACG Publications. All rights reserved.
Original Article

6) Rapid Profiling and Identification of Triterpene Saponins in Three Different Cephalaria Species by UPLC-ESI-MS/MS

Rec. Nat. Prod. (2018) 12:5 ; 460 - 469
by Veysel Umut Celenk, Nazli Boke Sarikahya and Suheyla Kirmizigul

Triterpene saponins are bioactive glycosides which are responsible for the defense mechanism of the plants and have extensive structural diversity in many plant species. In this study, profile of triterpene saponins was determined in the crude n-BuOH extracts of CephalariahirsutaCephalaria elazigensis var. elazigensis, and Cephalaria procera taxa (Caprifoliaceae) by ultra pressure liquid chromatography coupled with electrospray ionization tandem mass spectrometry. The UPLC-ESI-MS/MS method has been validated to provide linearity, recovery, precision (repeatability), limit of detection and limit of quantification parameters for quantitative analysis. Identification and quantification of the compounds were based on a group of fragment ions and ESI-MS spectra; precursor ions were observed as [M+Na] + and [M+H] + in positive mode for molecular mass information. Thirty nine saponins were identified and quantified by reversed-phase liquid chromatography (RP-LC) and they were separated on C18 reverse phase column (50 mm x 2.1 mm, 1.7 µm) by methanol-water gradient containing 0.1 mM ammonium formate solution as a mobile phase. Among the detected compounds, 28 compounds in C. hirsuta, 4 compounds in C. elazigensis var. elazigensis and 22 compounds in C. procera were identified and quantified based on their retention times and mass spectra in comparison with the data of references which were isolated in our previous studies. In this study, rapid application of an UPLC-ESI-MS/MS approach for resolving the chemical content of complex crude n-BuOH extracts of three Cephalaria species were presented, for the first time.

DOI
http://doi.org/10.25135/rnp.45.17.10.179
Keywords
Cephalaria saponin UPLC-ESI-MS/MS
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© 2018 ACG Publications. All rights reserved.
Original Article

7) Identification and Quantification, by NMR and LC-MS, of Sterols Isolated from the Marine Sponge Aplysina aerophoba

Rec. Nat. Prod. (2018) 12:5 ; 470 - 479
by Pere Ferriol, Francisco J. Toledo Marante, Ignacio Brouard Martin, José J. Santana Rodríguez, Rayco Guedes Alonso, Alba González Benkovics and Roberto Mioso

Aplysterol, several didehydroaplysterols, and their acetylated derivatives were isolated from samples of the marine sponge Aplysina aerophoba, which had been collected on the coast of the Canary Islands, and were identified by chromatography and 1H- and 13C-NMR spectroscopy. A quantitative analysis was done, based on the relative intensities of the signals corresponding to the olefinic quaternary carbons from the 13C-NMR spectrum at 125 MHz. Finally, the results described were confirmed by ultra-high performance liquid chromatography tandem mass spectrometry (UHPLC-MS/MS).

DOI
http://doi.org/10.25135/rnp.52.17.11.558.204
Keywords
Aplysina aerophoba marine sponge sterols quantitative analysis NMR UHLC-MS/MS
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© 2018 ACG Publications. All rights reserved.
Original Article

8) β-Amyrin Rich Bombax ceiba Leaf Extract with Potential Neuroprotective Activity against Scopolamine-Induced Memory Impairment in Rats

Rec. Nat. Prod. (2018) 12:5 ; 480 - 492
by Nada M. Mostafa

The neuroprotective potential of Bombax ceiba L. (Malvaceae) leaves extract (BCLE) was evaluated herein for the first time. Memory impairment was induced in rats by scopolamine (SC) administration for seven days (1.5 mg/kg/day, i.p.). BCLE (200 mg/kg) or donepezil (1mg/kg) was administered orally a week before and then concomitantly with SC for another week. BCLE improved the rats’ behaviors estimated by Morris water maze and passive avoidance tests, where the rats showed prolongation in time spent in platform quadrant and step-through latency, respectively, compared to administration of SC alone. BCLE also ameliorated the antioxidant parameters (Catalase with malondialdehyde (MDA), and the SC-induced elevation of acetylcholinesterase (AChE) in rats’ brain tissues. Histopathological studies supported the above results. BCLE phytochemical study resulted in isolation and structural elucidation of β-sitosterol linoleate (first to be isolated from the genus) and β-amyrin. Twenty-seven compounds ( 93 .35%) were identified in BCLE by gas chromatography / mass spectrometry (GC/MS) . The major components were triterpenoids (69.82%), composing mainly of β-amyrin (45.28%), lupeol (15.03%) and olean-12-en-3-one (6.27%), in addition to fatty acid esters (13.37%) and steroids ( 7.75%), which were rich in methyl palmitate (9.87%) and stigmasterol acetate (4.91%), respectively. These compounds may be responsible for ameliorating the SC-induced oxidative stress and cholinergic dysfunction.

DOI
http://doi.org/10.25135/rnp.47.17.10.062
Keywords
ombax ceiba GC/MS β-amyrin neuroprotective scopolamine
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© 2018 ACG Publications. All rights reserved.
Original Article

9) A New ent-Pimarane-Type Diterpenoid Glycoside from Siegesbeckia pubescens

Rec. Nat. Prod. (2018) 12:5 ; 493 - 497
by Fengqing Xu, Hu a ping Hu, Ying Li, Yashuo Ren, Hongsu Zhao, Qi Huang and Jutao Wang

A new ent-pimarane-type diterpenoid glucoside , along with eight known same skeleton type were isolated from the ethanol extract of Siegesbeckia pubescens Makino by means of various chromatographic techniques (silica gel, RP-8, Sephadex LH-20, Pre-HPLC). Their structures were elucidated on the ba sis of spectroscopic analyses and the new one identified as ent-15-methylene-2α,16,19-trihydroxy-pimar-8(14)-ene-19-O-β-D-glucopyranoside.

DOI
http://doi.org/10.25135/rnp.44.17.11.186
Keywords
Siegesbeckia pubescens ent -pimarane-type diterpenoid pubeside F.
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© 2018 ACG Publications. All rights reserved.
Original Article

10) Morphological, Indumentum and Chemical Characteristics and Analysis of the Volatile Components of the Flowers of Rhododendron ponticum L. subsp. ponticum (Ericaceae) of Turkish Origin §

Rec. Nat. Prod. (2018) 12:5 ; 498 - 507
by Sevim Küçük, Mine Kürkçüoğlu and Kemal Hüsnü Can Başer

Morphological, chemical and indumentum characteristics of Rhododendron ponticum L. subsp. ponticum collected from Bartın province have been investigated. A detailed description of the species has been prepared and compared with that published in the Flora of Turkey of Davis in a tabular form. The taxonomic and morphological characteristics of the plant material have been described and illustrated by drawings. Indumentum characteristics were also investigated. Volatiles of the flowers were trapped by a dynamic headspace SPME setup and their hexane extract were analyzed by GC/MS. Main components of the headspace trapped volatiles of flowers were characterized as α -pinene (44.5 %), β -pinene (10.8 %), linalool (4 %) and limonene (3.3 %) whereas main components in volatiles of the hexane extract were linalool (19.6 %), phenylethyl alcohol (19.1 %), myrtenol (10.1 %). citronellol (9.4 %) and phenylacetaldehyde (7.8%).

DOI
http://doi.org/10.25135/rnp.50.17.11.070
Keywords
Rhododendron ponticum subsp. ponticum Ericaceae Morphology Indumentum Chemistry GC-MS HS-SPME
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© 2018 ACG Publications. All rights reserved.
Short Report

11) Composition of Essential Oils from Schefflera myriocarpa Harms (Araliaceae) from Vietnam

Rec. Nat. Prod. (2018) 12:5 ; 508 - 511
by Dao T.M. Chau, Nguyen H. Hung, Le T. Huong, Nguyen V. Hung and Isiaka A. Ogunwande

The aim of this research was to determine the chemical constituents of essential oils derived from the leaf, bark and stems of Schefflera myriocarpa Harms (Araliaceae) grown in Vietnam for the first . The essential oils were obtained by hydrodistillation and investigated through gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The principal compounds identified in the essential oils were mainly monoterpenes represented by α-pinene (17.1%-21.2%), α-phellandrene (9.2%-27.4%) and limonene (19.8%-36.8%). In addition, methyl eugenol (10.4%) was found in the bark.

DOI
http://doi.org/10.25135/rnp.43.17.11.071
Keywords
Schefflera myriocarpa essential oil monoterpenes
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© 2018 ACG Publications. All rights reserved.
Short Report

12) Noropacursane: A New Nortriterpenoid from the Methanolic Extract of Carissa opaca

Rec. Nat. Prod. (2018) 12:5 ; 512 - 517
by Shehla Parveen, Naheed Riaz, Muhammad Saleem, Muhammad Ashraf, Tasneem Khatoon, Farrukh Nisar and Abdul Jabbar

Aerial parts of Carissa opaca have been investigated for the search of new bioactive secondary metabolites and a new nortriterpenoid: noropacursane (1) has been isolated together with three known compounds, namely, 6-methoxy-7-hydroxycoumarin (2), lupeol (3) and 4-ketopinoresinol (4). The structure of the new compound was established by 1D ( 1H-, 13C-NMR), 2D-NMR (HMBC, HSQC, COSY and NOESY) and high resolution mass spectrometry (HR-EI-MS), where as the structures of the known compounds were elucidated through 1D-NMR, mass spectrometric analysis and compared with the reported data in literature. All the isolates were evaluated for their biological potential against the enzymes acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and lipoxygenase (LOX) as well as for DPPH free radical scavenging assays. Compound 4 was found active against DPPH radical scavenging activity and BChE with IC 50 values of 83.41±0.17 and 101.81±0.24 µM, respectively, whereas compound 2 inhibited enzyme LOX with IC 50 value of 102.25±0.17 µM.

DOI
http://doi.org/10.25135/rnp.42.17.09.153
Keywords
Carissa opaca secondary metabolites isolation NMR nortriterpenoid biological activities
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© 2018 ACG Publications. All rights reserved.