Records of Natural Products

Year: 2017 Volume: 11 Issue:1 January-February

Original Article

1) Bioactive Dammarane Triterpenoids from the Bark of Drypetes acuminata from Paluma, North Queensland, Australia

Rec. Nat. Prod. (2017) 11:1 ; 1 - 8
by Suraj K. Pokharel, Mary Snow Setzer, Stefanie E. Greenleaf, Noura S. Dosoky, Betsy R. Jackes and William N. Setzer

Two known triterpenoids, friedelin and aglaitriol, and a new dammarane triterpenoid, aglaitriol 3-caffeate, have been isolated and identified in the chloroform bark extract of Drypetes acuminata P.I. Forst. (Putranjivaceae) from Paluma, north Queensland, Australia. The compounds were screened for antimicrobial and cytotoxic activity. Aglaitriol showed potent cytotoxic activity against three human tumor cell lines (MCF-7, MDA-MB-231, and 5637). Aglaitriol 3-caffeate showed moderate antibacterial activity against Staphylococcus aureus and Escherichia coli. A molecular docking analysis suggests topoisomerase II may be a likely protein target for aglaitriol.

Keywords
Drypetes acuminata dammarane aglaitriol aglaitriol 3-caffeate cytotoxicity antibacterial
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Original Article

2) Chemical Composition and Biological Activity of Volatile Extracts from Leaves and Fruits of Schinusterebinthifolius Raddi from Tunisia

Rec. Nat. Prod. (2017) 11:1 ; 9 - 16
by Alessandra Piras, Hanen Marzouki, Danilo Falconieri, Silvia Porcedda, Maria José Gonçalves, Carlos Cavaleiro and Ligia Salgueiro

Volatile oils composition from leaves and ripe fruits of pink pepper (Schinus terebinthifolius Raddi) growing in Tunisia were investigated using GC-FID and GC-MS techniques. Volatile oil extraction was achieved by hydrodistillation (HD) using a Clevenger apparatus and by supercritical fluid extraction (SFE) using carbon dioxide. All plant organs, gave SFE extracts chiefly composed by a -pinene, a -phellandrene, b -phellandrene, germacrene D and bicyclogermacrene. In the case of the fruits, both extraction techniques gave volatile oils of similar composition; whereas the comparison between the HD and SFE leave oils revealed important differences in the content of a -pinene (6.1 % vs traces), a -phellandrene (22.7 % vs 0.8 %) and b -phellandrene (14.6 % vs 1.2 %). All volatile samples were evaluated against yeasts and dermatophyte strains, being more active against Cryptococcus neoformans, particularly the volatile oil from the fruits, with MIC values of (0.32-0.64) mg/mL.Moreover, this oil revealed an inhibitory effect on germ tube formation in C. albicans at sub-inhibitory concentration. At the concentration of MIC/8 the inhibition of filamentation was more than 70 %.

Keywords
Schinus terebinthifolius supercritical carbon dioxide extracts essential oil antifungal activity
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Original Article

3) A Comparison of Diosgenin, Phenolics, Fatty Acid Profiles and Mineral Contents with Free Radical Scavenging Activity of Trigonella L. Species From Section Cylindricae

Rec. Nat. Prod. (2017) 11:1 ; 17 - 30
by Selma Ş. Uras Güngör, Ahmet İlçim and Gamze Kökdil

In this study, the fatty acids composition, the total flavonoids, phenolics, and mineral contents of Trigonella species belonging to Cylindricae Section (T. spruneriana, T. sibthorpii, T. kotschyi, T. mesopotamica, T. cylindricae, T. cilicica, T. filipes, T. velutina, T. strangulata and T. smyrnea) were determined. Diosgenin content in seeds and aerial parts of these species was investigated by RP-HPLC. Furthermore, the phytochemical profiles and radical scavenging activities of the plants were evaluated. The oils contained high proportions of α-linolenic (29.7-42.1 %) and linoleic acids (26.6-40.3 %). All the seed extracts had higher concentrations of total flavonoids and phenolics than those of aerial parts. T. strangulata and T. spruneriana seeds showed the highest total phenolics (201.35±0.51 and 191.90±0.86 mg GAE/g, respectively) and flavonoids contents (121.84±0.05 and 128.04±0.09 mg RE/g, respectively). For the DPPH radical scavenging assay, the extracts of four species of Trigonella showed moderate radical scavenging activity. The seeds contained high concentrations of potassium, calcium and phosphorus while the aerial parts were rich in calcium and potassium. Phytochemical screening tests showed that saponins, flavonoids, coumarins and fixed oils were main secondary metabolites. The highest diosgenin level was detected in T. cilicica seed and aerial part extracts (0.52±0.013 and 0.16±0.005 mg/g, respectively).

Keywords
Fabaceae Trigonella fatty acid total phenolic and flavonoid content mineral diosgenin
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Original Article

4) A New Acetylenic Compound and Other Bioactive Metabolites from a Shark Gill-derived Penicillium Strain

Rec. Nat. Prod. (2017) 11:1 ; 31 - 36
by Yi Zhang, Yan Feng, Markus Kramer, Frank Essmann and Stephanie Grond

Nine chiral compounds (19) were isolated from the static fermentation culture of a shark gill-derived fungus Penicillium polonicum AP2T1. These compounds include a new acetylenic aromatic ether (1 , (-)-WA ), four alkaloids ( a urantiomide C ( 2 ), fructigenine A (3), cyclopenin (4) and cyclopenol (5)) and four oxygenated compounds ((R)-penipratynolene (6), (3S,4S)-3,4-dihydro-3,4,8-trihydroxyl-naphthalenone (7), verrucosidin (8) and norverrucosidin (9)). Their structures were elucidated by MS, NMR , optical rotation and circular dichroism (CD) . In antimicrobial tests , compounds 14, 6 and 89 showed weak antibacterial activity against Staphylococcus aureus, Bacillus subtilis, and/or Escherichia coli.Compounds 3, 8 and 9 also exhibited moderate toxicity against Artemia salina larva , and showed cytotoxicity against human colon cancer cell line HCT116.

Keywords
econdary metabolites shark Penicillium polonicum bioactivity
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Original Article

5) Isolation and Characterization of New Constituents from Tricholepis eburnea

Rec. Nat. Prod. (2017) 11:1 ; 37 - 42
by Shagufta Rasool, Noureen Khan, Rashad Mehmood and Farzana Shaheen

hrough current phytochemical investigation on dichloromethane (DCM) fraction of 80% methanolic extract of Tricholepis eburnea, seven chemical constituents were isolated and their structures were elucidated by spectroscopic analyses. Two of them were identified as new flavonoids as trichonoide A (1) and trichonoide B (2), while the other five known constituents β-sitosterol (3), 3-O-acetyl-β-stigmastanol (4), 3β,17β,20-trihydroxy-l-oxo-(20R, 22 R)- witha-5,14,24-trienolide (5), pectolinaringenin (6), and dillenetin (7) were isolated for the first time from this species .

Keywords
Tricholepis eburnea asteraceae structural elucidation trichonoides A and B
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Original Article

6) Melilotoside Derivatives from Artemisia splendens (Asteraceae)

Rec. Nat. Prod. (2017) 11:1 ; 43 - 50
by Fariba H. Afshar, Abbas Delazar, Hossein Nazemiyeh, Lutfun Nahar, Sedigheh B. Moghaddam, Blessing O. Mbaebie, Simon Gibbons and Satyajit D. Sarker

A combination of solid-phase-extraction (SPE) and reversed-phase preparative high-performance liquid chromatography (prep-HPLC) of the methanolic extract of the aerial parts of Artemisia splendens (common name: “Asia Minor Wormwood”), an endemic Iranian species, afforded Z- and E-melilotosides (1 and 2), Z- and E-4-methoxy-melilotosides (3 and 4), and a new dimer, bis-ortho-Z-melilotoside (5, named: splendenoside). Whilst the structures of these compounds (1-5) were elucidated unequivocally by spectroscopic means, the in vitro free-radical-scavenging property of 1-5 was determined by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. This is the first report on the occurrence of any melilotoside derivatives in the genus Artemisia.

Keywords
Artemisia splendens Asteraceae 2 2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenger melilotoside splendenoside.
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Short Report

7) Antibacterial and Cytotoxic Activity of Extracts and Isolated Compounds from Myrciariaferruginea (Myrtaceae)

Rec. Nat. Prod. (2017) 11:1 ; 51 - 56
by Cinthia Costa de Lima, Kátia M. T. Caffaro, Maria Gabriella S. Araújo, Maria Lysete de A. Bastos, Lucia M. Conserva, Jamylle Nunes S. Ferro and Emiliano Barreto

This study evaluated for the first time the antibacterial activity, cell viability and migration ability on   3T3 murine fibroblast  cells of extracts and isolated compounds [lupeol (1), hexamethylcoruleoellagic acid (2) and a mixture of 1 and betulinaldehyde (3)] of Myrciaria ferruginea. In antibacterial assays extracts were susceptible only against S. aureus (MIC 500 μg/mL) and S. epidermidis (MIC ranging from 7.8 to 500 μg/mL) and compounds 1-3have shown no significant activity. In trials for c ell viability, with exception of MeOH-H 2O fraction from leaves (viable cells > 90%), both the crude extract and other fractions showed inhibition of cell growth (viable cells ≤ 80% at 15.625 and 31.25 μg/mL); while the samples from stems, with the exception of CHCl 3 fraction that showed strong cytotoxic effect at the lowest concentration tested (15.625 μg/mL), the other fractions were not cytotoxic. Compounds (1-3) inhibited cell viability in dose dependent manner (15.625 to 500 μg/mL). Mixture containing 1 and 3 showed inhibitions only in concentrations greater than 62.5 μg/mL while compound 2 decreased from the lowest concentration tested. In scratch wound assay, these compoundsnot increased the population of fibroblasts at concentrations less than 62.5 μg/mL.

Keywords
Myrciaria ferruginea antibacterial activity cell viability fibroblast cells MTT assa
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Short Report

8) Chemical Composition and Antimicrobial Activity of Essential Oil of Lepechiniaradula Benth Epling

Rec. Nat. Prod. (2017) 11:1 ; 57 - 62
by Vladimir Morocho, María Luisa Toro, Luis Cartuche, Diana Guaya, Eduardo Valarezo, Omar Malagón and Jorge Ramírez

The essential oil (EO) was obtained by hydrodistillation from the aerial parts of Lepechiniaradula Benth Epling (Lamiaceae) from Ecuador. Thirty-four compounds accounting to 93.4% of the total oil were identified. The main constituents of the essential oil were δ-3-carene (19.9%), β-pinene (17.0%), (E)-β-caryophyllene (9.7%) and (E-E)-α-farnesene (9.4%). The essential oil of L.radula possessed strong antifungal activity against Trichophytonrubrum (ATCC® 28188) and Trichophytonmentagrophytes (ATCC® 28185).

Keywords
Lepechinia radula Lamiaceae δ-3-carene Trichophyton rubrum Trichophyton mentagrophytes.
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Short Report

9) SİL||Chemical Composition and Antimicrobial Activity of Essential Oil of Lepechiniaradula Benth Epling

Rec. Nat. Prod. (2017) 11:1 ; 63 - 68
by

An ethyl acetate (EtOAc) extract of Laurencia nidifica was found to have toxic effect against brine shrimp larvae (Artemia salina). Bioassay-guided fractionation of the EtOAc extract resulted in the isolation of four known halogenated sesquiterpenes, laurinterol (1), isolaurinterol (2), aplysin (3), and a -bromocuparene (4). Their structures were established on the basis of spectral analysis and comparison with literature data. Among isolated compounds, only laurinterol showed strong toxicity against A. salina. Further experiments revealed that laurinterol also exhibited repellent activity against the maize weevil Sitophilus zeamais , insecticidal activity against the termite Reticulitermes speratus, and acetylcholinesterase (AChE) inhibitory effect . This is the first report of insecticidal and repellent activities of laurinterol.

Keywords
Laurinterol Laurencia nidifica h alogenated secondary metabolites brine shrimp i nsecticid al activity termiticidal activity
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Short Report

10) Insecticidal and Repellent Activit ies of Laurinterol from the Okinawan Red Alga Laurencia nidifica

Rec. Nat. Prod. (2017) 11:1 ; 63 - 68
by Takahiro Ishii, Takumi Nagamine, Binh Cao Quan Nguyen and Shinkichi Tawata

An ethyl acetate (EtOAc) extract of Laurencia nidifica was found to have toxic effect against brine shrimp larvae (Artemia salina). Bioassay-guided fractionation of the EtOAc extract resulted in the isolation of four known halogenated sesquiterpenes, laurinterol (1), isolaurinterol (2), aplysin (3), and a -bromocuparene (4). Their structures were established on the basis of spectral analysis and comparison with literature data. Among isolated compounds, only laurinterol showed strong toxicity against A. salina. Further experiments revealed that laurinterol also exhibited repellent activity against the maize weevil Sitophilus zeamais , insecticidal activity against the termite Reticulitermes speratus, and acetylcholinesterase (AChE) inhibitory effect . This is the first report of insecticidal and repellent activities of laurinterol.

Keywords
Laurinterol Laurencia nidifica h alogenated secondary metabolites brine shrimp i nsecticid al activity termiticidal activity
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Short Report

11) Essential Oil Composition of Three Centaurea Species from Turkey: Centaurea aggregata Fisch. & Mey. ex. DC. subsp. aggregata, C. balsamita Lam. and C. behen L.

Rec. Nat. Prod. (2017) 11:1 ; 69 - 73
by Tuğçe Erdoğan, Burcu Sümer, Özge Özçınar, Uğur Çakılcıoğlu, Betül Demirci, Kemal Hüsnü Can Başer and Bijen Kıvçak

The essential oils of Centaurea aggregata subsp. aggregata, C. balsamita and C. behen collected in the same habitat from Turkey, have been investigated. A total of 26, 54 and 26 components were identified in C. aggregata subsp. aggregata, C. balsamita and C. behen, respectively. The main constituents of the investigated populations of the three taxa have been revealed as follows: Centaurea aggregata subsp. aggregata: hexadecanoic acid (35.8%), phytol (7.2%), caryophyllene oxide(6.0%), spathulenol (6.0%); C. balsamita: hexadecanoic acid (23.0%), spathulenol (8.9%), germacrene D (2.1%); C. behen: hexadecanoic acid (32.7%), germacrene D (14.8%), and phytol (12.3%).

Keywords
entaurea aggregata subsp. aggregata Centaurea balsamita Centaurea behen Asteraceae essential oil.
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Short Report

12) A New Sugar Ester from the Roots of Acanthus ilicifolius

Rec. Nat. Prod. (2017) 11:1 ; 74 - 76
by Na Lin, Bo Yi, Juan Li, Wanke Zhang and Xiaopo Zhang

A new compound, 1,2-di-(syringoyl)-β-D-glucopyranose, together with erigeside C, were isolated from the roots of Acanthus ilicifolius. The structure of the new compound was elucidated by extensive spectroscopic methods, including 1D, 2D NMR and HRESIMS spectroscopic data. The cytotoxic activities of these compounds were evaluated against HepG2, A-549, and HeLa cells in vitro. However, none of them showed cytotoxic activities.

Keywords
Acanthus ilicifolius 1 2-di-(syringoyl)-β-D-glucopyranose cytotoxic activities.
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Short Report

13) A New Phloroglucinol Derivative Isolated from Hypericum afrum, a Plant Endemic to Algeria

Rec. Nat. Prod. (2017) 11:1 ; 77 - 81
by Farida Larit, Francisco León, Narayan D. Chaurasiya, Babu L. Tekwani, Samira Benyahia, Samir Benayache and Stephen J.Cutler

A new phloroglucinol derivative, identified as 3-benzoyl-3-hydroxy-5-(3-methylbut-2-en-1-yl)cyclopentane-1,2,4-trione (1 ), together with eight previously reported compounds, quercetin, myricitrin, hypericin, biapeginin, pseudohypericin, myricetin, 1,3,5,6-tetrahydroxyxanthone, and β-sitosterol were isolated from the chloroform, ethyl acetate and butanol extracts of the aerial part of Hypericum afrum (Lam.). Their structures were elucidated by spectroscopic analyses, including 1D-, 2D-NMR and HRESIMS. The EtOAc extract showed moderate MAO-A inhibition with an IC 50 value of 3.35 μg/mL. Bioassay-guided fractionation of the EtOAc extract resulted in the isolation of quercetin as the active component exhibiting MAO-A inhibitory activity with an IC 50 value of 1.25 μM.

Keywords
Hypericum phloroglucinol derivatives MAO-A and MAO-B spectroscopic analyses .
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Short Report

14) Volatile Constituents of Three Myrsine L. Species from Brazil

Rec. Nat. Prod. (2017) 11:1 ; 82 - 87
by Arthur L. Corrêa, Hildegardo S. França, Luis Armando C. Tietbohl, Bruna N. Luna, Marcelo G. Santos, Maria de Fátima Freitas, Adriana P. Oliveira and Leandro Rocha

The chemical compositions of the essential oils obtained by hydrodistillation from the aerial parts of Myrsine rubra, Myrsine gardneriana and Myrsine parvifolia and the fruits of Myrsine parvifolia were elucidated by a combination of GC and GC-MS analyses. The main constituents of the native M. parvifolia were caryophyllene oxide (14.4%), β-caryophyllene (12.6%) and γ-Muurolene (7.9%) of the leaves oil and β-caryophyllene (11.7%), δ-Cadinene (7.1%) of the fruit oil. The volatile oil of the endemic M. rubra leaves was dominated by β-caryophyllene (17.2%), γ-Muurolene (11.1%), Germacrene B (10.0%). The essential oil of the native M. gardneriana leaves was characterized by β-caryophyllene (18.0%), γ-Muurolene (8.4%). These three Myrsine species are similar in the dominance of sesquiterpenes. By contrast, monoterpenes were found only in the volatile oil from the fruits of M. parvifolia. To the best of our knowledge, this study is the first report on the volatile constituents of M. rubra, M. gardneriana, M. parvifolia.

Keywords
Myrsine rubra Myrsine gardneriana Myrsine parvifolia essential oil
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Short Report

15) Difference in Volatile Composition of Chenopodium murale from Two Different Locations of Cyprus

Rec. Nat. Prod. (2017) 11:1 ; 88 - 91
by Kaan Polatoğlu, Betül Demirci, İhsan Çalış and Kemal Hüsnü Can Başer

Volatile composition of Chenopodium murale from Değirmenlik and Salamis locations of Cyprus were trapped with headspace solid-phase microextraction (HS-SPME) technique and analyzed by GC-MS. Twenty-one compounds were identified comprising of 80.5% of the volatile sample from the Değirmenlik and twenty-six compounds were identified comprising of 82.2% of the volatile from the Salamis sample. Volatiles of C. murale from Değirmenlik contained 18.7% benzaldehyde, 8.6% yomogi alcohol 6.8% 1-hexanol and 6.5% dihydromyrcenol as the main components whereas volatiles of the sample from Salamis contained 20.5% yomogi alcohol, 14.5% camphor, 8.1% 1-hexanol and 6.6% 2-ethyl-hexanol. The volatiles of C. murale from both locations contained unexpected irregular monoterpene yomogi alcohol which is previously known to be restricted to Asteraceae genus. Both locations showed variations in their compositions which suggests the chemotype variation could be observed from this species.

Keywords
Chenopodiastrum Chenopodium murale yomogi alcohol benzaldehyde camphorvolatiles .
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