bluuebunny/crossref_metadata_2025 huggingface dataset:
Chemotypic Variation of Conocephalum salebrosum in the Southeastern Appalachian Range: A Search for Cryptic Plant Biodiversity Around the Tennessee River Valley
Authors: Craft Jonathan D. , Harrelson Daniel , Setzer William N.
Published: March 2019

The chemotaxonomy of the Conocephalum spp. complex, based on GC-MS analysis of the volatile compositions, has helped to reveal cryptic biodiversity and delineate actual distribution patterns of chemotypes. In the Appalachian Mountains, two samples from eastern central part of the range were previously shown to be C. salebrosum. Additionally, it has recently come to light that stress can alter the volatile composition of C. conicum. This study address a previously unsampled region of the southeastern Appalachians, a region that is a biodiversity epicenter, to determine if more chemotypic diversity remains to be seen for the Conocephalum spp. complex. A common garden experiment was performed, but yielded more of a common stress experiment, and significantly altered the volatile compositions. Wild-collected controls and a meta-analysis of these data and those from previous works suggest that the common garden experiment caused stress and that the liverworts sampled belong to the C. salebrosum clade of of the Conocephalum spp. complex.
Essential Oils of some Mentha Species and Cultivars, their Chemistry and Bacteriostatic Activity
Authors: Ludwiczuk Agnieszka , Kiełtyka-Dadasiewicz Anna , Sawicki Rafał , Golus Joanna , Ginalska Grażyna
Published: March 2019

The major purpose of this study was to determine the chemical relationships between the essential oils (EO) obtained form 18 mint samples of different species and its cultivars. GC/MS analysis of all essential oils showed that oxygenated monoterpenoids are the major components of these oils, with the exception of Mentha arvensis ‘Banana’. Based on the chemical composition of the essential oils, the analyzed mints can be divided into five groups. Group I was characterized by the presence of menthol and menthone, piperitenone oxide is the major constituent of group II, linalool of group III, carvone characterizes group IV, while 3-octanone is the most characteristic compound for group V. A reference strain of biofilm forming Staphylococcus epidermidis ATTC 35984 was tested against the obtained essential oils. Two of them, M. suaveolens ‘Variegata’ and M. x piperita ‘Almira’ exhibited significant bacteriostatic activity. The MIC values of these EOs were 0.25% and 0.5% respectively in comparison with an average MIC of 4% of the other tested mint EOs. Both active EOs are characterized by the presence of piperitenone oxide as the major component.
Icacina trichantha, A Tropical Medicinal Plant
Authors: Che Chun-Tao , Zhao Ming , Guo Brian , Onakpa Michael M.
Published: March 2019

This is a review on the pharmacological properties and chemical composition of Icacina trichantha (Icacinaceae), a food and medicinal plant native to West Africa. The tuber is a good source of nutrients such as starch; it also exhibits a variety of pharmacological activities in animal models. Chemical analysis has revealed the presence of a series of unusual pimarane-type diterpenes.
16-Hydroxycembra-1,3,7,11-tetraene, a new Cembrane Diterpene from Malaysian Soft Coral Genus Sarcophyton
Authors: Kamada Takashi , Phan Chin-Soon , Tin Hoe-Seng , Vairappan Charles Santhanaraju , Muhammad Tengku Sifzizul Tengku
Published: March 2019

One new cembrane diterpene, 16-hydroxycembra-1,3,7,11-tetraene (1), along with three known compounds, 15-hydroxycembra-1,3,7,11-tetraene (2), sarcophine (3) and sarcophytoxide (4) were isolated from Sarcophyton sp. collected from Karah Island, Terengganu, West Malaysia. Their structures were elucidated based on spectroscopic data. Activities of these compounds against antibacterial resistant clinical bacteria are reported. Only 1 exhibited inhibition against Staphylococcus aureus.
A Novel 3,4-Secocycloartane Triterpene, Bearing a Tetrahydropyran Moiety, from Pasania formosana Leaf
Authors: Lee Shoei-Sheng , Xi Yue , Chen Chien-Kuang , Chang Ching-Chia , Tsai Sheng-Fa
Published: March 2019

Bioassay guided fractionation against α-glucosidase and separation of the ethanolic extract of Pasania formosana leaf by chromatographic methods led to the isolation of a novel secocycloartane triterpene. This compound, named pasasecocycloartenoic acid, was elucidated as 21,24( R)-epoxy-25-hydroxy-3,4-secocycloart-4(28)-en-3-oic acid through analysis of 1D and 2D NMR spectra and on the basis of HRESIMS data. The compound showed weak activity against α-glucosidase, but its poor solubility hampered the bioassay.
Three Tetracyclic Triterpenoic Acids from Dysoxylum densiflorum and Their Antibacterial Activities
Authors: Dharmayani Ni Komang T. , Juliawaty Lia D. , Syah Yana M.
Published: March 2019

This paper reports the chemical isolation and antibacterial properties of terpenoid components of Dysoxylum densiflorum. Three new tetracyclic triterpenoic acids, densiflorinic acids A-C (1-3), were isolated from the acetone extract of the plant's leaves. The structures of the three compounds were determined mainly by extensive analysis of 1-D and 2-D NMR spectroscopic data. On antibacterial evaluation, the highest activity was shown by compound 1 against Bacillus subtilis with an IC50 of 26.5 μM.
Optimization of 3', 4'-Anhydrovinblastine Synthesis in vitro Using Crude Extracts of Catharanthus roseus Irradiated with Near-Ultraviolet Light
Authors: Asano Mamiko , Harada Kazuo , Umeno Akiko , Hirata Kazumasa
Published: March 2019

Dimeric indole alkaloids (DIAs), such as vinblastine and vincristine, found in Catharanthus roseus are used clinically as antitumor drugs. A stable supply of DIAs is desired because these alkaloids are very expensive due to their low abundance in plants. A coupling reaction between catharanthine (CAT) and vindoline (VID) is the rate-limiting step of DIAs biosynthesis in planta. 3', 4'-Anhydrovinblastine (AVLB), the product of the coupling reaction, is the precursor of CAT and VID. Therefore, an effective AVLB production system is greatly required. Previously we found that the coupling reaction of CAT and VID to produce AVLB occurred in the presence of flavin mononucleotide and manganese ion (II) by irradiation with near-ultraviolet light at a peak of 370 nm without the presence of any enzyme. In this study, we investigated the effects of organic solvents on this non-enzymatic reaction. We show that the addition of 10% methanol to the reaction mixture permitted the preparation of a highly concentrated substrate solution, resulting in a high yield of AVLB by the coupling reaction. Conditions for the coupling reaction in 10% methanol solution were optimized. We also confirmed that the coupling reaction could occur in crude extracts of C. roseus obtained by organic solvent extraction. These findings suggest a method to produce DIAs on a large scale with reduced production costs.
Virgin Coconut Oil and its Cardiovascular Health Benefits
Authors: Ma Zheng Feei , Lee Yeong Yeh
Published: March 2019

Cardiovascular disease (CVD) is known as the number one cause of death worldwide. It is associated with huge health care costs and loss of productivity in the population. Poor diet is an important risk factor in CVD. Diet rich in polyunsaturated fatty acids, such as virgin coconut oil (VCO), has been associated with a reduced risk of CVD. This systematic review focused on studies that reported the association between VCO and the biochemical measurements associated with CVD. These studies conclude that VCO shows promising effects in improving the biochemical derangements associated with CVD, thus lowering the CVD risk. However, most of these studies were performed in animals with very limited data from human. Future investigations are needed to examine the health benefits of VCO in human intervention studies.
Influence of Thermal Processing and in vitro Digestion on the Antioxidant Potential of Ginger and Ginger Containing Products
Authors: Koch Wojciech , Kukula-Koch Wirginia , Dziedzic Marcin , Głowniak Kazimierz , Asakawa Yoshinori
Published: March 2019

Zingiber officinale (Zingiberaceae) is a common spice and a medicine widely cultivated in tropical and subtropical climate around the globe, which contains both precious polyphenols and terpenes in its extracts. The ubiquity of ginger in a variety of foods encouraged the authors to assess the influence of thermal processing and digestion of the plant material on its antioxidant capacity. The obtained results of DPPH assay showed marked differences in the antioxidant potential of the processed samples, in comparison with fresh ginger rhizomes. Autoclave and microwave heating procedures were found to evoke the mildest decomposition of the antioxidants and increase the antioxidant capacity of the plant (from IC50 of 210±10 for a fresh rhizome to ca 160±16 μg/mL for the former, and to 150±18 for the latter technique), whereas frying and boiling for different durations significantly deteriorated the antiradical potential up to IC50 = 940±36 μg/mL. Mouth and stomach digestion decreased the antioxidant potential of the extracts even to ca. 1000±47 μg/mL. A protective role of saliva towards the antioxidant compounds against hydrochloric acid and pepsin activities has been proven. A marked deterioration in antioxidant capacity in digested rhizomes may shed new light on the actual absorption of consumed polyphenols with food products.
Odor-Active Components of Luo Han Guo (Siraitia grosvenorii)
Authors: Tomiyama Kenichi , Sakurai Kazutoshi , Yaguchi Yoshihiro , Kawakami Yukihiro
Published: March 2019

The volatile components of the dried fruit of Luo Han Guo ( Siraitia grosvenorii Swingle) belonging to the family Cucurbitaceae were analyzed by AROMASCOPE® technique using MonoTrap® DCC18 as an absorbent. A total of 124 volatile components were identified from the headspace aroma solvent extract. The major components were ethanol, butan-l-ol, pentanal, 2-methylbutanal, hexanal, furfural, pent-3-en-2-one, acetic acid, propionic acid, 3-methylbutanoic acid, hexadecanoic acid, and so on. Among them, acetic acid, 3-methylbutanoic acid, and 3-hydroxy-4,5-dimethylfuran-2(5 H)-one (sotolon) strongly contributed to the overall aroma of the fruit. Besides, sotolon and 5-ethyl-3-hydroxy-4-methylfuran-2(5 H)-one (maple furanone) were responsible for the characteristic molasses-like aroma of the fruit.
Aphelasteroside F, a new Asterosaponin from the Far Eastern Starfish Aphelasterias japonica
Authors: Popov Roman S. , Ivanchina Natalia V. , Kalinovsky Anatoly I. , Kharchenko Sofiya D. , Kicha Alla A. , Malyarenko Timofey V. , Ermakova Svetlana P. , Dmitrenok Pavel S.
Published: March 2019

A new asterosaponin aphelasteroside F (1) was isolated from the ethanolic extract of the Far Eastern starfish Aphelasterias japonica along with the previously known ophidianoside F (2). The structure of 1 was elucidated by extensive use of NMR and ESI-MS techniques, and chemical transformations. Compound 1 contains a new type of asterosaponin carbohydrate chain linked to C-6 of the steroid aglycone aphelaketotriol. Compounds 1 and 2 at non-toxic concentrations slightly inhibited cell proliferation and colony formation of the cancer melanoma cell lines SK-Mel-28, SK-Mel-5, and RPMI-7951.
Absolute Configuration and Body Part Distribution of the Alkaloid 6-epi-Monanchorin from the Marine Polychaete Chaetopterus variopedatus
Authors: Shubina Larisa K. , Makarieva Tatyana N. , Denisenko Vladimir A. , Dmitrenok Pavel S. , Dyshlovoy Sergey A. , von Amsberg Gunhild , Glazunov Valery P. , Silchenko Artem S. , Stonik Inna V. , Lee Hyi-Seung , Lee Yeon-Ju , Stonik Valentin A.
Published: March 2019

As a result of the first study on secondary metabolites from the cosmopolitan bioluminescent marine tube polychaete Chaetopterus variopedatus, a new bicyclic guanidine alkaloid, 6- epi-monanchorin (1), along with the previously known monanchorin (2) were isolated. The structure of 1 was elucidated by spectroscopic and chemical methods, including a cleavage of the C1–O7 bond to obtain a secondary alcohol (3), which was used to determine the absolute configurations by Mosher's method. It was found that 1 and 2 were mainly accumulated in a secreted mucus special organ of the worm (food net), where green and blue-green microalgae were detected. A biosynthetic pathway to 6- epi-monanchorin and monanchorin from dietary polyenic fatty acid precursors was proposed.
N-Demethylaaptanone, A new Congener of Aaptamine Alkaloids from the Vietnamese Marine Sponge Aaptos aaptos
Authors: Utkina Natalia K. , Denisenko Vladimir A.
Published: March 2019

A new compound, N-demethylaaptanone (5), having an oxygenated 1,6-naphthyridine core, has been isolated from the Vietnamese marine sponge Aaptos aaptos, along with the known metabolites, aaptamine (1), isoaaptamine (2), 9-demethylaaptamine (3), and aaptanone (4). The structure of N-demethylaaptanone was determined as 9-hydroxy-8-methoxy-4 H-benzo[ de][1,6]-naphthyridine-5,6-dione from spectroscopic data.
Two Pyrones with Antibacterial Activities from Alpinia malaccensis
Authors: Juwitaningsih Tita , Juliawaty Lia D , Syah Yana M.
Published: March 2019

A new pyrone derivative, malakavalactone (2), was isolated from the acetone extract of Alpinia malaccensis fruits, along with a known compound kavalactone (1). The structure of the new compound was determined based on NMR and mass spectral data. Compounds 1 and 2 showed weak antibacterial activities against eight pathogenic bacteria.
Inhibition of Spore Germination and Appressorium Formation of Rust Species by Plant and Fungal Metabolites
Authors: Barilli Eleonora , Cimmino Alessio , Masi Marco , Evidente Marco , Rubiales Diego , Evidente Antonio
Published: March 2019

Eight fungal and plant metabolites belonging to different classes of naturally occurring compounds, a 24-oxa[14]-cytochalasan as cytochalasin B (1), a trisubstituted isocoumarin as 6-hydroxymellein (2), a tetracyclic pimarane diterpene as sphaeropsidin A (3), a chalcone as cavoxin (4), a pentasubstituted benzofuranone as cyclopaldic acid (5), a bicyclic-sesquiterpene as inuloxin A (6), a epipolythiopiperazine as gliotoxin (7) and a cyclohexene epoxide as epi-epoformin (8), were tested for their effectiveness in reducing early stages of development of several major rust fungi from the genera Puccinia and Uromyces. Spore germination and appressoria formation were assessed on pre-treated detached leaves, under controlled conditions. Among the various metabolites evaluated, compounds 5 and 8 were the most effective in inhibiting fungal germination and penetration of all rust species studied at values comparable with those obtained by fungicide application, while compound 4 was phytotoxic to plant leaves at any concentration tested.
Antioxidant Activities and Reduced Amyloid-β Toxicity of 7-Hydroxycalamenene Isolated from the Essential Oil of Zelkova serrata Heartwood
Authors: Yen Pei-Ling , Cheng Sen-Sung , Wei Chia-Cheng , Lin Huan-You , Liao Vivian Hsiu-Chuan , Chang Shang-Tzen
Published: March 2019

The in vitro and in vivo antioxidant activities and its potential to protect against amyloid-β toxicity of essential oils from Zelkova serrata (Thunb.) Makino were investigated in the model organism Caenorhabditis elegans. The results revealed that the essential oil of Z. serrata heartwood exhibited great radical scavenging activities and high total phenolic content. In vivo assays showed significant inhibition of oxidative damage in wild-type C. elegans under juglone-induced oxidative stress and heat shock. Based on results from both in vitro and in vivo assays, the major compound in essential oil of heartwood, (-)-(1 S, 4 S)-7-hydroxycalamenene (1 S, 4 S-7HC), may contribute significantly to the observed antioxidant activity. Further evidence showed that 1 S, 4 S-7HC significantly delayed the paralysis phenotype in amyloid beta-expressing transgenic C. elegans. These findings suggest that 1 S, 4 S-7HC from the essential oil of Z. serrata heartwood has potential as a source for antioxidant or Alzheimer's disease treatment.
A Survey of the Chemical Compounds of Piper spp. (Piperaceae) and Their Biological Activities
Authors: Xiang Cai-Peng , Shi Yan-Ni , Liu Fang-Fang , Li Hai-Zhou , Zhang Ying-Jun , Yang Chong-Ren , Xu Min
Published: March 2019

The genus Piper is one of the largest genera in the Piperaceae, with most species widely distributed globally, covering all continents. To date, many Piper species have been scientifically investigated for their chemical diversities and interesting broad spectrum of bioactivities, including central nervous system (CNS), pesticidal, antifungal and antibacterial effects. This review systematically summarizes the scaffolds of the alkaloids reported, the major chemicals isolated from Piper spp., and their biological activities. Besides the alkaloids, some neolignans with rearranged skeletons show structural diversities, while the chalcones, flavonoids and kava-pyrones have some potential activities. Herein, the sesquiterpenes and phenolic compounds from Piper species and their bioactivities are also surveyed.
Integration of Traditional and Western Medicine in Vietnamese Populations: A Review of Health Perceptions and Therapies
Authors: Adorisio Sabrina , Fierabracci Alessandra , Rossetto Ariele , Muscari Isabella , Nardicchi Vincenza , Liberati Anna Marina , Riccardi Carlo , Van Sung Tran , Thuy Trinh Thy , Delfino Domenico V.
Published: March 2019

In Vietnam, two types of traditional medicine (TM) are practiced: thuoc nam, medicine of the South, and thuoc bac, medicine of the North, both of which are largely based on herbal drugs used by different Vietnamese ethnic groups. This review presents recently published information from various databases regarding TM, especially herbal drugs, and its integration with Western medical practices outside and inside Vietnam. We first discuss the integration of traditional and modern health concepts by Vietnamese immigrants living outside Vietnam. Next, we describe native and emigrated health education and practices of pharmacy students, health professionals, and citizens living in Vietnam. Finally, we report the recent biological validation of medicinal plants and non-herbal therapies emerging from Vietnamese TM and their current and potential medical uses as identified by Western approaches. The main example described here involves utilization of the tree Artocarpus tonkinensis by the ethnic minority of Black Hmong in northern Vietnam, who use a decoction of its leaves to treat arthritis and backache without apparent adverse effects. Our comprehensive review emphasizes that, although Vietnam has a very rich collection of TM practices (particularly the use of herbal drugs), these therapies should be biologically and clinically validated with modern Western methods for optimal integration of Western and traditional medicine in global populations.
Insecticidal Pregnane Glycosides from the Root Barks of Periploca sepium
Authors: Li Renfeng , Zhao Ximei , Shi Baojun , Wei Shaopeng , Zhang Jiwen , Wu Wenjun , Hu Zhaonong
Published: March 2019

To explore novel lead compounds for botanical pesticides from natural sources, a new pregnane glycoside (periplocoside) P2 as well as its isomer, a known pregnane glycoside P1, were isolated from the root barks of Periploca sepium using a bioactivity-guided method, and their structures were confirmed by 1D NMR, 2D NMR, IR, ESI-MSn and HRMS. Their insecticidal activities were evaluated against 3rd instar larvae of M. separata, and the results indicated that P2 exhibited excellent insecticidal activity with LC50 values of 2.9 and 2.2 mg/mL after 24 and 48 h, respectively, much lower than those of the positive control celangulin-V (24.7 and 21.0 mg/mL after 24 and 48 h, respectively). This work demonstrated that pregnane glycosides from Periploca sepium could be promising lead compounds for developing botanical pesticides urgently needed in agriculture.
Apigenin Suppresses Angiogenesis by Inhibiting Tube Formation and Inducing Apoptosis
Authors: Kim Hyun Ju , Ahn Mok-Ryeon
Published: March 2019

Apigenin has been reported to exert angiogenic and anticancer activities in vitro. The mechanism of inhibition of angiogenesis by apigenin, however, has not been well-established. In this study, we investigated whether apigenin not only inhibited tube formation but also induced apoptosis in human umbilical vein endothelial cells (HUVECs). Furthermore, strong antiangiogenic activity of apigenin was observed in the in vivo assay using chick embryo chorioallantoic membrane (CAM). We also analyzed changes in survival signals and the apoptotic pathway through Western blotting. The results indicate that apigenin exerts its antiangiogenic effects through induction of endothelial apoptosis.
HPLC Fingerprint Combined with Quantitation of Phenolic Compounds and Chemometrics as an Efficient Strategy for Quality Consistency Evaluation of Sambucus nigra Berries
Authors: Viapiana Agnieszka , Wesolowski Marek
Published: March 2019

Sambucus nigra L. berries have been traditionally used as culinary and medicinal ingredients. To ensure the highest quality of elderberry plant products for consumers, the objective of this study was to develop a HPLC fingerprint procedure for quality consistency evaluation of S. nigra berries obtained from various herbal manufacturers in Poland. The HPLC profiles of thirteen batches of elderberries showed more than sixty peaks in each chromatogram, including fourteen well-resolved common peaks. Four of these were assigned to caffeic acid, syringic acid, myricetin and quercetin. Based on the chromatographic profiles of all the samples, the reference HPLC fingerprint and similarity values were calculated by Matlab 9.1 software. Quantitation of phenolic compounds (flavonols and phenolic acids) revealed that the S. nigra samples with the highest quantity differ to a small extent with regard to the mean content of phenolic compounds. On the other hand, in batches of elderberries with lower similarity values, higher differences in the mean phenolic compound content were observed. The results of hierarchical cluster and principal component analyses showed that samples classified into one group are associated with a similar chemical composition, reflected in fourteen common HPLC peaks and similarity values. Chromatographic fingerprint combined with quantitation of plant bioactive compounds and unsupervised data analysis techniques can be a useful and efficient strategy for monitoring the quality consistency of elderberry fruits.
Aroma Profile of Galangal Composed of Cinnamic Acid Derivatives and Their Structure-Odor Relationships
Authors: Hasegawa Toshio , Hashimoto Momohiro , Fujihara Takashi , Yamada Hideo
Published: March 2019

Cinnamic acid derivatives are important odorants due to their characteristic scent. Some fragrance materials, such as cinnamon bark, matsutake mushrooms, and Kaempferia galanga L. rhizome (galangal), contain several cinnamic acid derivatives as important odor constituents. The main odor constituent of galangal is ( E)-ethyl 4-methoxycinnamate, but the odor of this compound is different from that of galangal. We investigated the aroma profile of galangal using our previously described method that considers the intermolecular interactions of the odorant compounds with their receptors. Odorant compounds in galangal were extracted by hexane extraction, steam distillation, and headspace sampling. The odor of the hexane extract was different from that of the steam distillate and similar to that of galangal; therefore, we searched for the key compounds contributing to the aroma profile of galangal by separating the constituents of the hexane extract. A fraction with a galangal-like odor was obtained by bulb-to-bulb distillation of the hexane extract. The main component of this fraction was not ( E)-ethyl 4-methoxycinnamate, but rather ethyl cinnamate. These results indicate that ethyl cinnamate is more important in the aroma profile of galangal than ( E)-ethyl 4-methoxycinnamate. GC-MS analysis revealed that this fraction contained aromatic compounds, cyclic terpenes, and linear chain compounds in addition to ethyl cinnamate. We synthesized cinnamic acid derivatives and examined the importance of the odor expression of these cinnamic acid derivatives. Cinnamic acid derivatives lacking a p-methoxy group had a strong fruity odor. Replacement of the hydrogen atom at the para position with a methoxy group altered and weakened the odor. We found that a p-methoxy group in cinnamic acid derivatives plays an important role in the aroma profile of galangal.
Essential Oil Composition of Pimpinella cypria and its Insecticidal, Cytotoxic, and Antimicrobial Activity
Authors: Tabanca Nurhayat , Nalbantsoy Ayse , Bernier Ulrich R. , Agramonte Natasha M. , Ali Abbas , Li Andrew Y. , Yalcin Husniye Tansel , Gucel Salih , Demirci Betul
Published: March 2019

A water-distilled essential oil (EO) from the aerial parts of Pimpinella cypria Boiss. (Apiaceae), an endemic species in northern Cyprus, was analyzed by GC-FID and GC-MS. Forty-five compounds were identified in the oil, which comprised 81.7% of the total composition. The compound classes in the oil were oxygenated sesquiterpenes (33.9%), sesquiterpenes (22.0%), monoterpenes (11.4%), oxygenated monoterpenes (2.6%), and phenylpropanoids (7.5%). The main components of the oil were ( Z)-β-farnesene (6.0%), spathulenol (5.9%), ar-curcumene (4.3%), and 1,5-epoxy-salvial(4)14-ene (3.8%). The P. cypria EO deterred yellow fever mosquitoes (Aedes aegypti) from biting at a concentration of 10 μg/cm2 in in vitro bioassays. The oil was tested for repellency in assays using human volunteers. The oil had a minimum effective dosage (MED) for repellency of 47 ± 41 μg/cm2 against Ae. aegypti, which was less efficacious than the positive control N,N-diethyl-3-methylbenzamide (DEET). In larval bioassays, P. cypria EO showed an LC50 value of 28.3 ppm against 1st instar Ae. aegypti larvae. P. cypria EO demonstrated dose dependent repellency against nymphs of the lone star tick, Amblyomma americanum. Between 45.0% and 85.0% repellency was observed at concentrations ranging from 26 to 208 μg/cm2. However, P. cypria EO was less effective compared with DEET in the tick bioassays. Cytotoxicity assays showed that the P. cypria EO did not exhibit significant effects up to the maximum treatment concentration of 50 μg/mL on HEK293, PC3, U87MG, and MCF cells. P. cypria EO also demonstrated moderate antimicrobial activity against Gram-negative and -positive bacteria with MICs ranging from 15.6 to 62.5 μg/mL, except for Candida albicans, which showed the same MIC value of 7.8 μg/mL as the positive control, flucytosine. This is the first report on the chemical composition of P. cypria EO and its insecticidal, toxicant, cytotoxic, and antimicrobial activity.
Chemical and Biological Study of Cladosporin, an Antimicrobial Inhibitor: A Review
Authors: Wang Xiaoning , Wedge David E , Cutler Stephen J
Published: March 2019

Natural antifungal agents are generally broad-spectrum compounds with low mammalian and environmental toxicity. Cladosporin is a naturally occurring fungal metabolite mainly isolated from the endophytic fungus Cladosporium cladosporioides. This review article summarizes the chemistry and biological properties of cladosporin covering references published from 1971–2016, including the source, phytochemical characterization, biosynthesis, total synthesis, structure and activity (SAR), and biological activity of cladosporin. Cladosporin exhibited potent antibacterial, antifungal, insecticidal, and anti-inflammatory activities, as well as plant growth regulatory effects. More importantly, cladosporin was identified as having potent, nanomolar, antiparasitic activity against both Plasmodium falciparum blood and liver stages via specific inhibition of protein synthesis. This provides a new approach for the design of isocoumarin-based compounds for the treatment of malaria. Herbicidal activity and antifungal activity against Cryptococcus neoformans (IC50 value of 17.7 μg/mL) of cladosporin are also described here in the review for the first time. Cladosporin selectively inhibited the growth of a monocot (agostis) and showed no activity against a dicot (lettuce), which indicates its great potential as a selective herbicide for monocots in agriculture use. The above data suggest that cladosporin has great potential utility as a lead compound in the development of agrochemicals against certain plant pathogens and pharmaceuticals against drug-resistant bacteria and parasites.
Biological Properties of Some Volatile Phenylpropanoids
Authors: Ilijeva Radmila , Buchbauer Gerhard
Published: March 2019

Plants and their extracts are the new field of interest for many scientists and also of some pharmaceutical industries. In order to provide more information for their usage in the prevention and treatment of diseases many clinical trials and researches are being carried out. In this review the biological activities and the mechanism of action of volatile phenylpropanoids (PPs) found in essential oils (EOs) are presented. The aim of this overview is to show that volatile PPs found in EOs can exert many of the biological activities which are generally attributed to EOs. Almost all of the PPs possess antimicrobial, anti-inflammatory and anticancer activities. These are related to the different substitution of the phenylpropane molecule. For each isolated group not only one, but more pharmacological activities can be credited.
A New Ursane-type Triterpenoid and Other Constituents from the Leaves of Crataegus azarolus var. aronia
Authors: Mahmud Sarbast A. , Al-Habib Omar A.M , Bugoni Serena , Clericuzio Marco , Vidari Giovanni
Published: March 2019

A new ursane-type triterpene acid, named azarolic acid (1), along with four known phenolic compounds and four known triterpene acids, was isolated from the crude EtOAc extract of the leaves of Crataegus azarolus var. aronia L. The structure of 1 was determined from 1D and 2D NMR spectroscopic data. Euscaphic acid showed high anti-vasoconstriction effects on aortic rings, supporting the use of this medicinal plant in cardiovascular disease.
Antimicrobial and Cytotoxic Evaluation of New Quinazoline Derivatives
Authors: Turan-Zitouni Gülhan , Yurttaş Leyla , Saka Güner , Cantürk Zerrin , Gencer Hülya Karaca , Baysal Merve , Kaplancιklι Zafer Asιm
Published: March 2019

The synthesis of nine new quinazoline derivatives (2a-2i) and evaluation of their antimicrobial and cytotoxic activities were aims of the present work. For the synthesis of the compounds, 2-chloro-6,7-dimethoxyquinazolin-4-amine was used as the initial starting material. The intermediate product, 2-hydrazinyl-6,7-dimethoxyquinazolin-4-amine, was reacted with appropriate aromatic aldehydes to obtain 2-(2-benzylidenehydrazinyl)-6,7-dimethoxyquinazolin-4-amine derivatives as final compounds. The structures of the compounds were elucidated by 1H- and 13C-NMR, IR, and MS analyses. The new pure compounds were evaluated for their potential antimicrobial and cytotoxic activities using in vitro microdilution and cell culture techniques, respectively. The compounds 2e and 2f may be promising candidates for the treatment of fungal infections with their activity and cytotoxicity.
Simultaneous Determination of the Five Marker Compounds in Melandrium firmum using High-Performance Liquid Chromatography with Photodiode-Array Detection
Authors: Seo Chang-Seob , Shin Hyeun-Kyoo
Published: March 2019

In Korean folk medicine, Melandrium firmum Rohrbach (Caryophyllaceae) has been used to treat various diseases, including anuria, breast cancer, and gonorrhea. In this study, a high-performance liquid chromatography method with photodiode-array UV detection (HPLC-PDA) was established and then validated for the simultaneous determination of five flavonoids in M. firmum: schaftoside, homoorientin, cytisoside, vitexin, and isovitexin. Separation of the five compounds was performed on a Gemini C18 column at 40°C by gradient elution of two mobile phases. The flow rate and injection volume were 1.0 mL/min and 10 μL, respectively. The HPLC-PDA method showed excellent linear regression with r2 values of 0.9999 within the test ranges. The limits of detection and quantification of all components were 0.01–0.11 and 0.04–0.34 μg/mL, respectively. The extraction recovery of the five analytes was 97.6—105.6% and the RSD values were < 2.0% The relative standard deviation values of intra- and interday precision for all analytes were < 1.71 and < 1.46%, respectively. As determined using the established and validated HPLC-PDA method described here, the amounts of the five marker compounds in M firmum were 0.02–2.54 mg/g.
Inhibitory Activities of Sesame Seed Extract and its Constituents against β-Secretase
Authors: Matsumura Shinichi , Murata Kazuya , Zaima Nobuhiro , Yoshioka Yuri , Morimoto Masanori , Matsuda Hideaki , Iwaki Masahiro
Published: March 2019

The need for a preventive agent against dementia led us to screen natural plant resources. Among the herbs and spices tested, sesame seed prepared from Sesamum indicum seeds showed potent β-secretase inhibitory activity. The active principles were determined to be sesamin and sesamolin, typical lignans in S. indicum. The IC50 values of sesamin and sesamolin were 257 and 140 μM, respectively. These compounds were investigated in a preliminary absorption experiment. After oral administration, these compounds were detected in an intact form in the brain and serum. These results suggest that consumption of sesame seeds may prevent dementia by sesamin and sesamolin, the constituents in sesame seeds.
Essential Oils and Their Vapors as Potential Antibacterial Agents against Respiratory Tract Pathogens
Authors: Ács Kamilla , Bencsik Tímea , Böszörményi Andrea , Kocsis Béla , Horváth Györgyi
Published: March 2019

Increasing appearance of antibiotic-resistant pathogens, which could be one of the major causes of respiratory tract infections, has again drawn attention to natural substances and alternative treatments. Therefore, the aim of the present study was the antibacterial evaluation of cinnamon bark, clove, thyme, citronella, peppermint, Scots pine, and eucalyptus essential oils (EOs) against respiratory tract pathogens such as methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa with in vitro vapor phase (VP) and tube dilution (TD) techniques. The chemical and percentage compositions of the EOs were determined by GC-FID and GC-MS analysis. Among the EOs, cinnamon bark was the most effective against all the investigated pathogens (MIC: 31.25–125 μL/L) in the VP assay, but clove oil presented the best inhibition against MRSA in liquid medium (MIC: 0.1 mg/mL). Thyme oil also showed antibacterial activity against MRSA and the antibiotic-sensitive strain of P. aeruginosa in both methods. In higher concentration, we found that peppermint oil was effective only in vapor form; contrarily, eucalyptus oil was more efficient in liquid medium. Surprisingly, Scots pine did not show any activity in our test systems. These results suggest that EOs could be promising solutions for the problem of antibiotic resistance due to their multiple composition and complex mode of action. However, more in vivo studies are necessary to calculate the effective dose of EOs in patients and determine their possible side effects and toxicity.
Distribution and Discrimination Study of Bioactive Compounds from Berberis species using HPLC-ESI-QTOF-MS/MS with Principle Component Analysis
Authors: Singh Awantika , Bajpai Vikas , Kumar Sunil , Kumar Brijesh , Srivastava Mukesh , Arya Kamal Ram , Sharma Kulwant Rai
Published: March 2019

Berberis species have been used extensively as raw material in various herbal medicines. In this work, a fast and sensitive method based on reversed-phase high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (HPLC-ESI-QTOF-MS/MS) was used to assist the distribution and discrimination study of bioactive compounds from Berberis species such as B. aristata, B. asiatica, B. chitria, B. jaeschkeana, B. koehneana, B. lyceum, B. petiolaris and B. pseudoumbellata. The HPLC separation was performed on a Thermo Betasil C8 column (250 mm x 4.5 mm, 5μ) using gradient elution with a mobile phase of 0.1% aqueous solution of formic acid (v/v) and acetonitrile. The high resolution (HR) and collision induced dissociation (CID) mass spectrometry experiments were conducted in order to provide molecular-mass information and MS/MS fragmentation patterns of the compounds for structural elucidation. A total of 59 compounds were tentatively identified and characterized including three acids, forty-one alkaloids and twelve flavonoids using seventeen reference standards for authentication. Principle component analysis (PCA) was also applied to discriminate eight Berberis species according to their plant parts i.e., leaf, stem and root. The highest total content of identified compounds was detected in the root of all the Berberis species wherein alkaloids were predominant.
Beauvericin K, a New Antifungal Beauvericin Analogue from a Marine-derived Fusarium sp
Authors: Xu Xiuli , Zhao Shujiang , Yu Ying , Chen Zhengkun , Shen Huihui , Zhou Li
Published: March 2019

Chemical investigation of a Chinese collection of a marine-derived fungus, Fusarium sp., led to the characterization of beauvericin K, a new analogue of beauvericin. The structure of the new compound was elucidated by detailed spectroscopic analysis, including 1D and 2D NMR methods, and HRMS. Beauvericin K showed significant activity against the yeast Candida albicans with an IC50 value of 6.25 μg/mL.
Isoprenylated Flavonoids from Roots of Artocarpus styracifolius
Authors: Lin Qin Hua , Yuan Jin Bin , Ma Zhi Lin , Liang Jian , Zhai Xiao Xiao , Khan Ikhlas A , Ding Yuan Qing , Ren Gang
Published: March 2019

Seven isoprenylated flavonoids were isolated from Artocarpus styracifolius, including one new triisoprenylated flavone, styracifolin D (1), and six known ones, artocarpone B (2), kuwanon C (3), 6-C-prenyl luteolin (4), albanin A (5), 2,4,2′,4′-tetrahydroxy-3′-(3-methyl-2-butenyl)-chalcone (6), and 3′-[γ-hydroxymethyl-( E)-γ-methylallyl]-2,4,2′,4′-tetrahydroxychalcone 11′- O-coumarate (7). The structures of these compounds were determined by analysis of their spectroscopic and mass spectrometric data. Of them, 3 and 5 exhibited inhibitory effects on cathepsin K with IC50 values of 114.6 and 7.4 μM, respectively.
Cytotoxic and Antileishmanial Components from the Bark Extract of Ruyschia phylladenia from Monteverde, Costa Rica
Authors: Steinberg Kelly Marie , Shrestha Samon , Dosoky Noura S. , Monzote Lianet , Piñón Abel , Haber William A. , Setzer William N.
Published: March 2019

The bark of Ruyschia phylladenia was collected from Monteverde, Costa Rica, and extracted with acetone. Bioactivity-directed chromatographic separation of the crude acetone bark extract of R. phylladenia led to isolation and identification of lupeol, betulinic acid, and isofraxidin. Lupeol and betulinic acid showed in-vitro cytotoxic activity to MCF-7, MDA-MB-231, and 5637 human tumor cell lines. Isofraxidin was not cytotoxic, but did show antileishmanial activity to Leishmania amazonensis promastigotes.
A New Cardenolide and Other Compounds from Salsola tetragona
Authors: Ghorab Hamida , Khettaf Abdelkrim , Lehbili Meriem , Kabouche Ahmed , Magid Abdulmagid Alabdul , Harakat Dominique , Voutquenne-Nazabadioko Laurence , Kabouche Zahia
Published: March 2019

One new cardenolide, 3- O-β-D-allopyranosylcoroglaucigenin (salsotetragonin) (1), was isolated from the aerial parts of Salsola tetragona Delile with four known cardenolides (2–5), two known flavonoids (6–7), three known phenolic compounds (8–10) and two known fatty acids (11–12). Their structures were identified by spectroscopic analyses and by comparison of their spectral data with those reported in the literature. Compounds 1–5, 7, 10 and 12 were isolated from the genus Salsola for the first time. This is the first report on cardenolides identified in the Amaranthaceae family.
Preparation and Validated Analysis of Anthocyanin Concentrate from the Calyces of Hibiscus sabdariffa
Authors: Opletal Lubomir , Chocholousova-Havlikova Lucie , Siatka Tomas , Cahliková Lucie , Locarek Miroslav , Ali Badreldin H. , Manoj Priyadarshini , Ramkumar Aishwarya , Al Suleimani Yousuf M. , Al Za'abi Mohammed , Karaca Turan , Nemmar Abderrahim
Published: March 2019

Extracts of Hibiscus sabdariffa calyces have been shown to have various medicinal properties, some of which have been reported to be due to anthocyanins present in the calyces. To study whether these claims are valid, it is necessary to produce an extract with a high anthocyanin content and to have available a method to identify and quantify the individual compounds in the product. A method of extraction and purification has been developed based on a polyamide column chromatographic purification step. Using this method, anthocyanin concentrates were produced containing from 57 to 64% of delphinidin-3-sambubioside plus cyanidin-3-sambubioside. A rapid, efficient and validated HPLC analytical method was developed and used for the analysis of the anthocyanin concentrate.
Vibrational and Thermal Studies of Essential Oils Derived from Cistus ladanifer and Erica arborea Shrubs
Authors: Carrión-Prieto Paula , Martín-Ramos Pablo , Maria Teresa M.R. , Hernández-Navarro Salvador , Garrido-Laurnaga Fermín , Eusébio M. Ermelinda S. , Martín-Gil Jesús
Published: March 2019

Essential oils from the two most representative shrub species from the Iberian Peninsula (namely Cistus ladanifer L. and Erica arborea L.) have been characterized by Fourier transform infrared spectroscopy (FTIR) and thermoanalytical techniques (TG/DTG and DSC). Vibrational spectra have been compared with those of components of the plants, and with those of oils, gums and resins from other species. The different content in terpenoids of C. ladanifer oil (mainly mono- and sesquiterpenoids) and E. arborea oil (mainly triterpenoids) is reflected in the ATR-FTIR by the position of the bands at around 2873 cm−1, 1730 cm−1 and 1678 cm−1. As regards their thermal behavior, C. ladanifer-derived oil evinced higher thermal stability than that of obtained from E. arborea: the pyrolysis of the former was sensitized at 210°C, whereas for the later it occurred at 143°C. These temperatures are high enough to state that thermolabile constituents such as terpenoids are conserved in the hydrodistillation and that this extraction process ensures the recovery of the main constituents of both essential oils.
Chemical Profile and in vitro Biological Activities of Essential Oils of Nectandra puberula and N. cuspidata from the Amazon
Authors: da Silva Joyce Kelly R. , Andrade Eloísa Helena A. , Mourão Rosa Helena V. , Maia José Guilherme S. , Dosoky Noura S. , Setzer William N.
Published: March 2019

Essential oils (EO) from leaves and branches of Nectandra puberula Schott (Nees) and from leaves of N. cuspidata Nees & Mart. were obtained by hydrodistillation and their chemical compositions determined by gas chromatography - mass spectrometry (GC-MS). The main compounds identified from N. puberula EO were apiole (22.2%), β-caryophyllene (15.1%), β-pinene (13.3%), germacrene D (8.3%), pogostol (6.6%) and bicyclogermacrene (6.4%) in the leaves; and apiole (28.1%), pogostol (19.8%) and guaiol (11.2%) in the branches. The EO of N. cuspidata leaves showed β-caryophyllene (26.9%), bicyclogermacrene (16.0%) and spathulenol (5.2%) as the main compounds. The EOs were subjected to antibacterial screening and displayed promising activity against Escherichia coli (MIC = 19.5 μg.mL−1). In addition, the EOs were tested for cytotoxic activity against MCF-7 breast tumor cells and the IC50 values were 64.5 ± 1.6 and 117.1 ± 11.9 μg.mL−1 for the leaf EOs of N. puberula and N. cuspidata, respectively.
The Rare Amino Acid Building Block 3-(3-furyl)-Alanine in the Formation of Non-ribosomal Peptides
Authors: Maddah Fayrouz El , Nazir Mamona , König Gabriele M.
Published: March 2019

Microorganisms have made considerable contributions to the production of peptide secondary metabolites, many of them with therapeutic potential, e.g., the fungus-derived immunosuppressant cyclosporine A and the antibiotic daptomycin originating from Streptomyces. Most of the medically used peptides are the product of non-ribosomal peptide synthetases (NRPS), incorporating apart from proteinogenic also unique, non-proteinogenic amino acids into the peptides. An extremely rare such amino acid is 3-(3-furyl)-alanine. So far, only few peptides have been found that contain this residue, including the rhizonins, bingchamide B and endolides. The producer of the rhizonins was proven to be the bacterial endosymbiont Burkholderia endofungorum inside the fungus Rhizopus microsporus. The microbial origin, chemistry and bioactivity of the 3-(3-furyl)-alanine containing peptides are the focus of this review.
Phytochemical Profile of Inula britannica from Bulgaria
Authors: Ivanova Victoria , Trendafilova Antoaneta , Todorova Milka , Danova Kalina , Dimitrov Dimitar
Published: March 2019

The flower heads of Inula britannica L. of Bulgarian origin afforded sesquiterpene lactones (gaillardin, britannin, 11,13-dihydroinuchinenolide B, ivalin, pulchellin C), triterpenoids (3- O-palmitates of 16β-hydroxylupeol, 16β-hydroxy-β-amyrin, and faradiol) and flavonoids (quercetin, luteolin, luteolin-7- O-glucoside). All compounds are known and they were identified by spectral methods. The observed differences in the chemical content of the chloroform and methanol extracts were also reflected in their free radical scavenging activity, evaluated by DPPH and ABTS assays. Intraspecific variability of I. britannica is discussed.
Production of Δ7-Sterols from In Vitro Root Cultures of Endangered Gypsophila trichotoma
Authors: Zdraveva Petranka , Popova Pavlinka , Shkondrov Aleksandar , Krasteva Ilina , Ionkova Iliana
Published: March 2019

Species from the genus Gypsophila are known for their medicinal, industrial and decorative applications. G. trichotoma Wend. is an endangered plant species for the Bulgarian flora according to the Red Data Book. Δ7-Sterols, which are unusual and rare in the plant kingdom, are present in the roots of this species. In previous studies different in vitro cultures were established from aerial parts of the species. The objective of this study was to explore the possibility for production of Δ7-sterols from in vitro cultured roots of G. trichotoma. The root cultures were grown on six modified MS media and the quantity of sterols was analyzed. These findings will serve to solve the important matter of the role of nutrients on sterols biosynthesis.
Analysis of Antioxidant Polyphenols in Loquat Leaves using HPLC-based Activity Profiling
Authors: Nawrot-Hadzik Izabela , Granica Sebastian , Abel Renata , Czapor-Irzabek Hanna , Matkowski Adam
Published: March 2019

Leaves of Eriobotrya japonica (loquat) have been used in Traditional Chinese Medicine with beneficial effects in numerous diseases. Extracts from loquat leaves are rich in antioxidants, containing among others: triterpenes, sesquiterpenes, flavonoids, tannins, and megastigmane glycosides. However, there is no conclusive study revealing which of these compounds are the main bioactive principles. The goal of this study was to pinpoint compounds responsible for strong antioxidant activity. Eriobotryae folium was extracted and fractionated between solvents of increasing polarity. All extracts and fractions were screened for total polyphenols and tannins, and antioxidant activity was checked by DPPH, phosphomolybdenum and linoleic acid tests. The ethyl acetate fraction demonstrated the highest antioxidant activity and contained the largest amount of polyphenols. Applying HPLC-based activity profiling to localize antioxidants revealed that cinchonain IIb, as well as flavonoid glycosides such as hyperoside, isoquercitrin, kaempferol glycosides, quercetin-rhamnoside, as well as two tentatively identified protocatechuic acid derivatives are the main substances responsible for the strong antioxidant activity of the ethyl acetate fraction.