bluuebunny/crossref_metadata_2025 huggingface dataset:
New Humulenes from Hyptis incana (Labiatae)
Authors: Satoh Mitsuru , Satoh Yoshio , Anzai Yasuhiro , Ajisawa Daisuke , Matsuzaki Keiichi , Makino Mitsuko , Fujimoto Yasuo
Published: March 2019

Two new humulene-type sesquiterpenes, named hyptishumulene I (1) and II (2), have been isolated, together with eight known compounds, a humulene-type sesquiterpene (3), a monoterpene (4) and six abietane-type diterpenoids (5–10) from the aerial parts of Hyptis incana (Labiatae). The cytotoxic activity of the isolated compounds against mouse leukemia cells (L1210) was examined. The abietane-type diterpenoids (5–10) showed rather potent growth inhibitory activity (IC50<15 μM), while the new humulene-type compounds (1 and 2) exhibited moderate activity (IC50>50 μM).
Crotofolane Diterpenoids from Croton caracasanus
Authors: Chávez Katiuska , Compagnone Reinaldo S. , Riina Ricarda , Briceño Alexander , González Teresa , Squitieri Emilio , Landaeta Carlos , Soscún Humberto , Suárez Alírica I.
Published: March 2019

Four new crotofolane-type diterpenoids, crotocarasin (A-D) (1–4), together with the known crotofolin E, were isolated from a dichloromethane extract of the stems of Croton caracasanus Pittier. The structures of the new compounds were determined by spectroscopic methods, and the structure of 3 was further confirmed by single-crystal X-ray data analyses.
Antiangiogenic Activity of Flavonoids from Melia azedarach
Authors: Kumazawa Shigenori , Kubota Satomi , Yamamoto Haruna , Okamura Naoki , Sugiyama Yasumasa , Kobayashi Hirokazu , Nakanishi Motoyasu , Ohta Toshiro
Published: March 2019

Three flavonoid glycosides, 1 (rutin: quercetin 3- O-rutinoside), 2 (kaempferol 3- O-robinobioside) and 3 (kaempferol 3- O-rutinoside) were isolated from the subcritical water extracts of Melia azedarach leaves. Strong antiangiogenic activity of these compounds was observed in the in vivo assay using the chorioallantoic membrane (CAM) from growing chick embryos.
New Therapeutic Potentials of Milk Thistle (Silybum marianum)
Authors: Milić Nataša , Milošević Nataša , Suvajdžić Ljiljana , Žarkov Marija , Abenavoli Ludovico
Published: March 2019

Silymarin is a bioflavonoid complex extract derived from dry seeds of Milk thistle [( Silybum marianum(L.) Gaernt. (Fam. Asteraceae/Compositaceae)] whose hepatoprotective effect has clinically been proved. Low toxicity, favorable pharmacokinetics, powerful antioxidant, detoxifying, preventive, protective and regenerative effects and side effects similar to placebo make silymarin extremely attractive and safe for therapeutic use. The medicinal properties of silymarin and its main component silibinin have been studied in the treatment of Alzheimer's disease, Parkinson's disease, sepsis, burns, osteoporosis, diabetes, cholestasis and hypercholesterolemia. Owing to its apoptotic effect, without cytotoxic effects, silymarin possesses potential applications in the treatment of various cancers. Silymarin is being examined as a neuro-, nephro- and cardio-protective in the damage of different etiologies due to its strong antioxidant potentials. Furthermore, it has fetoprotective (against the influence of alcohol) and prolactin effects and is safe to be used during pregnancy and lactation. Finally, the cosmetics industry is examining the antioxidant and UV-protective effects of silymarin. Further clinical studies and scientific evidence that silymarin and silibinin are effective in the therapy of various pathologies are indispensable in order to confirm their different flavonolignan pharmacological effects.
New Guaian-type Sesquiterpene from Wikstroemia indica
Authors: Kato Mamoru , He Yu-Min , Dibwe Dya Fta , Li Feng , Awale Suresh , Kadota Shigetoshi , Tezuka Yasuhiro
Published: March 2019

From a MeOH extract of powdered roots of Wikstroemia indica, we isolated a new guaian-type sesquiterpene (1) and two known guaian-type sesquiterpenes [oleodaphnal (2), 1α,7α,10α H-guaia-4,11-dien-3-one (3)], together with twelve known compounds: (+)-arctigenin, (+)-matairesinol, (+)-trachelogenin, (+)-nortrachelogenin, (+)-hinokinin, (+)-kusunokinin, 7-methoxycoumarin, 7-hydroxycoumarin (umbelliferone), daphnogitin, daphnoretin, salicifoliol, and (-)-pinoresinol. The structure of compound 1 was determined to be 4,10,11-guaiatrien-3-one-14-oic acid, by the analyses of spectral data.
Differences in the Chemical Composition of Arnica montana Flowers from Wild Populations of North Italy
Authors: Clauser Maria , Aiello Nicola , Scartezzini Fabrizio , Innocenti Gabbriella , Dall'Acqua Stefano
Published: March 2019

The flower heads of fourteen wild Arnica montana L. populations were collected in the summer of 2010 in the provinces of Trento, Brescia and Bergamo (Italy). The dried flowers were analyzed to assess their chemical diversity. HLPC-MS analysis led to the identification of phenolic derivatives and sesquiterpene lactones in the samples, confirming literature data. Quali-quantitative analysis of the flower heads showed similar qualitative patterns both for the phenolic as well as sesquiterpene lactone derivatives, while significant variability was obtained in the amounts (HPLC-DAD) of sesquiterpene lactones (0.45–2.31%), phenolic acids (1.44–2.88%) and flavonoids (0.96–2.44%). The highest quantities of sesquiterpene lactones, flavonoids and phenolic acids were found in Malga Fregasoga (1703 m above sea level), Rifugio Camini (1608 m a.s.l.) and Malga Sass (1817 m a.s.l.) samples, respectively.
New Diterpenes from Azorella spinosa
Authors: Astudillo Luis , Gutiérrez Margarita , Quesada Luisa , San-Martín Aurelio , Espinoza Luis , Peñailillo Patricio
Published: March 2019

Two new diterpenes,2-acetoxy-13-hydroxy-mulin-11-ene and 2-acetoxy-mulin-11, 13-diene, have been isolated from the aerial parts of Azorella spinosa and their structures determined by spectroscopic and conventional chemical methods. Furthermore, 2, 13-dihydroxy-mulin-11-ene was obtained using a basic hydrolysis of the first compound. Two diterpenes reported for other Azorella species have also been found, namely mulinolic acid and 13β-hydroxyazorellane, as well as the triterpene lactone of ursolic acid, quercetin, and 7-hydroxycoumarin. The compounds were evaluated using antibacterial, antioxidant and enzymatic assays; no significant activity was detected.
In vitro Antioxidant Activity, Phenolic Compounds and Protective Effect against DNA Damage Provided by Leaves, Stems and Flowers of Portulaca oleracea (Purslane)
Authors: Silva Rúben , Carvalho Isabel S.
Published: March 2019

This study analyzed the antioxidant properties of Portulaca oleracea L., known as purslane. The samples (leaves, flowers and stems) were collected at two different locations in Portugal: Tavira (L1) and Vendas Novas (L2). Assays for total antioxidant activity, total phenolic content and ferric-reducing antioxidant power were conducted and, for both locations, significantly higher values ( P<0,05) were observed for stems (508.8 and 982.3 mg AAE/100 g DW, 1008.6 and 2285.5 mg GAE/100 g DW, 121.0 and 166.3 mg TE/100 g DW, respectively for each location), than in leaves or flowers. In the DPPH assay, the three-plant parts from L2 reached the 50% inhibition rate in lower concentrations than plants from L1. On the other hand, higher concentrations of total monomeric anthocyanins were found in samples from L1 (95.5, 88.8 and 86.0 mg/L) than in samples from L2 (81.7, 70.5 and 59.8 mg/L). The same was true for phenolic acids, estimated by liquid-chromatography, where methanol extracts were used. Phenolic extracts from all three-plant parts from both locations showed protective effects on DNA against hydroxyl radicals. This work suggests the possibility of benefit to human health from its consumption, related to the high antioxidant activity of purslane, even the stems, usually discarded in daily consumption.
How to Deal with Nomenclatoral Ambiguities of Trivial Names for Natural Products? – A Clarifying Case Study Exemplified for “Corymbosin”
Authors: Ramabharathi Vatsavaya , Schuehly Wolfgang
Published: March 2019

Many names of plant secondary compounds that have been isolated and identified in the course of phytochemical investigations are based either on the vernacular or Latin names of the source plants, are constructed according to rules of chemical nomenclature, or consist of in-between forms. Trivial names, based on the specific epithets of biological organisms, occasionally create confusion because such epithets are used in numerous combinations and, therefore, could potentially be used when naming chemical entities from radically different sources. Such an example of ambiguous naming is represented with the case of corymbosin, a name that was assigned to two chemically distinct compounds that were isolated and reported simultaneously in 1967 from two different spermatophyte taxa: a terpene glucoside from Turbina corymbosa and a flavone from Webera corymbosa. The flavone is more widespread and has been reported so far from 15 taxa, whereas the glucoside has thus far only been isolated from the original source species. Furthermore, glycosides named corymbosins K1-K4 were isolated in 2006 from Knoxia corymbosa. This article emphasizes the need to adhere to strict principles when naming secondary constituents and suggests that a practice should be applied that is similar to the application of the priority rules used in botanical nomenclature for homonyms. The use of the trivial name, corymbosin, should be applied only to the more widespread tricetin-7,3′,4′,5′-tetramethyl ether by rules of conservation.
Antiausterity Activity of Arctigenin Enantiomers: Importance of (2R,3R)-Absolute Configuration
Authors: Awale Suresh , Kato Mamoru , Dibwe Dya Fita , Li Feng , Miyoshi Chika , Esumi Hiroyasu , Kadota Shigetoshi , Tezuka Yasuhiro
Published: March 2019

From a MeOH extract of powdered roots of Wikstroema indica, six dibenzyl-γ-butyrolactone-type lignans with (2 S,3 S)-absolute configuration [(+)-arctigenin (1), (+)-matairesinol (2), (+)-trachelogenin (3), (+)-nortrachelogenin (4), (+)-hinokinin (5), and (+)-kusunokinin (6)] were isolated, whereas three dibenzyl-γ-butyrolactone-type lignans with (2 R,3 R)-absolute configuration [(-)-arctigenin (1), (-)-matairesinol (2), (-)-trachelogenin (3)] were isolated from Trachelospermum asiaticum. The in vitro preferential cytotoxic activity of the nine compounds was evaluated against human pancreatic PANC-1 cancer cells in nutrient-deprived medium (NDM), but none of the six lignans (1–6) with (2 S,3 S)-absolute configuration showed preferential cytotoxicity. On the other hand, three lignans (1*–3*) with (2 R,3 R)-absolute configuration exhibited preferential cytotoxicity in a concentration-dependent manner with PC50 values of 0.54, 6.82, and 5.85 μM, respectively. Furthermore, the effect of (-)- and (+)-arctigenin was evaluated against the activation of Akt, which is a key process in the tolerance to nutrition starvation. Interestingly, only (-)-arctigenin (1*) strongly suppressed the activation of Akt. These results indicate that the (2 R,3 R)-absolute configuration of (-)-enantiomers should be required for the preferential cytotoxicity through the inhibition of Akt activation.
Volatile Glycosides from the Leaves of Morus alba with a Potential Contribution to the Complex Anti-diabetic Activity
Authors: Hunyadi Attila , Herke Ibolya , Veres Katalin , Erdei Anna , Simon András , Tóth Gábor
Published: March 2019

The leaves and root bark of Morus alba, the white mulberry tree, are well-known traditional medicines for the treatment of type II diabetes. Several different types of constituents have been suggested to be responsible for the anti-diabetic activity of mulberry drugs, such as iminosugars, flavonoids and other phenolic compounds, glycopeptides and ecdysteroids. Our group recently suggested that a volatile-oil like fraction of the hot water extract of M. alba leaves, containing several phenyl-propane derivatives, can increase the glucose consumption of adipocytes. Here we report the isolation of three glycosylated volatile constituents from mulberry leaves, two megastigmane derivatives along with the β-D-glucoside of eugenol. Furthermore, a commercially available mixture of probiotic bacteria was assessed to study the effect of the intestinal flora on the megastigmane derivatives. Significant amounts of the aglycons of both compounds were liberated, suggesting that these compounds can be metabolized in the large intestines and absorbed without the sugar moiety after the consumption of a traditional mulberry tea. Based on literature data, both the glycosides and their aglycons have a potential contribution to the beneficial effects of mulberry leaves in type 2 diabetes.
Evaluation of the Anti-melanoma Activities of Sarcophine, (+)-7α,8β-Dihydroxydeepoxysarcophine and Sarcophytolide from the Red Sea Soft Coral Sarcophyton glaucum
Authors: Szymanski Pawel T. , Ahmed Safwat A. , Radwan Mohamed M. , Khalifa Sherief I. , Fahmy Hesham
Published: March 2019

Three natural cembranoids from the Red Sea soft coral Sarcophyton glaucum namely sarcophine (1), (+)-7α,8β-dihydroxydeepoxysarcophine (2) and sarcophytolide (3) were evaluated for their potential inhibitory effects on growth of mouse melanoma B16F10 cells. Compounds (1) and (2) maximally inhibit viability of melanoma cells during 48 hr and 72 hr treatment at concentrations that show no cytotoxicity on monkey kidney CV-1 cells and also inhibit de novo DNA synthesis and PARP activity. Compound (3) produced cytotoxic effects at the same concentration range it produces its antitumor effects. These data suggest that (1) and (2), but not (3), have potential for further development as antitumor agents against melanoma.
Nutritional and Functional Properties of Aqueous and Hydroalcoholic Extracts from Argentinean Propolis
Authors: Danert Fátima C. , Zampini Catiana , Ordoñez Roxana , Maldonado Luis , Bedascarrasbure Enrique , Isla María Inés
Published: March 2019

Bee propolis is a natural product extensively used as an ingredient in functional foods in amounts that may confer health benefits. The aim of this study was to investigate the nutritional and functional properties (antioxidant activity) of aqueous and ethanolic extracts of propolis samples from Santiago del Estero province, northern Argentina. All propolis extracts contained macronutrients (glucose, fructose, sucrose and proteins), micronutrients (Na, K, Ca, P and Mg) and trace elements (Fe). Spectrophotometric, TLC and HPLC-DAD analyses showed the presence of several phenolic, flavonoid and non-flavonoid compounds, but in all cases the flavonoids prevailed. The PCA of polyphenolic content provided a clear separation of propolis in Group 1 (SE1, 2, 3, 4 and 7) and Group 2 (SE5 and 6) associated with phenolic compound content and collection regions. Two compounds, pinocembrin and chrysin, which could be used as chemical markers of Santiago del Estero propolis, were identified in all samples. Propolis samples extracted with water presented better radical scavenging ability than ethanolic extracts, independent of the antioxidant method (scavenging activity of ABTS•+, DPPH•, HO• and O2•- and β-carotene bleaching test). Such results correlated closely with the levels of total phenols and flavonoids in samples. The results justify the use of Argentine propolis as a functional dietary supplement.
Anthraquinone and Naphthoquinone Derivatives from the Roots of Coptosapelta flavescens
Authors: Kongyen Wipapan , Rukachaisirikul Vatcharin , Phongpaichit Souwalak , Sawangjaroen Nongyao , Songsing Phruksa , Madardam Hattaya
Published: March 2019

Investigation of the acetone and methanol extracts of the roots of Coptosapelta flavescens using various chromatographic techniques led to the isolation of four anthraquinones (1 and 3–5) and one naphthoquinone (2). 1,4-Dimethoxy-2-methylanthraquinone (1) and 2-amino-3-methoxycarbonyl-1,4-naphthoquinone (2) are reported as natural compounds for the first time. This is the first report on the phytochemistry and biological activity of compounds from C. flavescens.
Methicillin-resistant Staphylococcus aureus, Vancomycin-resistant Enterococcus faecalis and Enterococcus faecium active Dimeric Isobutyrylphloroglucinol from Ivesia gordonii
Authors: Ahmed Marwa H. , Ibrahim Mohamed Ali , Zhang Jin , Melek Farouk R. , El-Hawary Seham S. , Jacob Melissa R. , Muhammad Ilias
Published: March 2019

Bioassay-guided fractionation of the chloroform soluble fraction of stem, leaf, and flower extracts of the American plant Ivesia gordonii led to the isolation of a new dimeric acylphloroglucinol, 3,3′-diisobutyryl-2,6′-dimethoxy-4,6,2′,4′-tetrahydroxy-5,5′dimethyldiphenyl methane (1), to which we have assigned the trivial name of ivesinol (1), together with a known monomeric acylphloroglucinol, 1,5-dihydroxy-2-(2′-methylpropionyl)-3-methoxy-6-methylbenzene (2). The structures of the isolated compounds were characterized using 1D- and 2D- NMR spectroscopy, including COSY, HMQC, HMBC, and ROESY experiments, as well as mass spectrometry. Ivesinol (1) showed potent activity against Staphylococcus aureus (SA) and methicillin-resistant S. aureus (MRSA) with IC50/MIC/MBC values of 0.10/1.25/>20 μg/mL and 0.05/0.31/>20 μg/mL, respectively (vs. IC50/MIC/MBC 0.13/0.5/1.0 μg/mL and 0.13/0.5/1.0 μg/mL of ciprofloxacin), while the corresponding monomer 2 was found to be less active. Compound 1 also demonstrated strong activity against vancomycin-resistant Enteococcus faecium ( VRE) with IC50/MIC/MBC values of 0.22/1.25/>20 μg/mL, whereas the reference standard ciprofloxacin was found to be inactive against this strain. In addition, compound 2 showed moderate activity against two species of Candida and Cryptococcus neoformans, while 1 was inactive against these fungi. In order to evaluate the influence of the acyl group(s) in phloroglucinol (3) as a ligand, the mono- (4) and diacetylphloroglucinol (5) were prepared from 3, and evaluated for their in vitro SA, MRSA, and VRE activities; 2,4-diacetylphloroglucinol (5) showed potent activity, like 1, against SA, MRSA, and VRE (ATCC 700221) with IC50/ MIC values of 0.3/2.5, 0.23/2.5, and 0.86/2.5 μg/mL, respectively, while 4 was inactive.
Antimicrobial Activity of Endophytic Fungi Isolated from Swietenia macrophylla Leaves
Authors: Ibrahim Darah , Lee Chong Chai , Sheh-Hong Lim
Published: March 2019

The endophytic fungi isolated from leaves of Swietenia macrophylla of different ages were examined for antimicrobial activity. The agar plug diffusion assay was used for primary screening, followed by the disc diffusion method. A total of 461 filamentous endophytic fungi were isolated and cultured to examine their antimicrobial properties. In the primary screen, 315 isolates (68.3%) exhibited activity against at least one of the test pathogenic microorganisms. The percentage of isolates exhibiting antimicrobial activity increased with leaf age. Endophytic fungal assemblages, as well as those isolates exhibiting antimicrobial properties appeared to increase with leaf age. The main antimicrobial compounds were produced extracellularly by the endophytic fungi. The results suggest that healthy leaves at older stages of growth can be a potential source for the isolation of endophytic fungi with antimicrobial properties.
Aroma Profile of Star Anise and the Structure-odor Relationship of Anethole
Authors: Hasegawa Toshio , Seimiya Haruna , Fujihara Takashi , Fujiwara Noriko , Yamada Hideo
Published: March 2019

Star anise is an important fragrance material that has a characteristic anise-like odor. Although the main component of star anise is ( E)-anethole, which accounts for over 90% of the constituents, the odor of ( E)-anethole is different from that of the material itself. Here, we examined the aroma profile of star anise. GC-MS analysis of star anise extracts showed that it contains many compounds with structures similar to ( E)-anethole. Our results indicate that ( E)-anethole is the key compound in the odor of star anise, but structurally similar compounds play an important role in creating its odor. We examined the structure-odor relationship of ( E)-anethole, focusing on the methoxy and 1-propenyl substituents. Altering the 1-propenyl group changed the odors of all the anethole derivatives. Replacing the methoxy group with a hydrogen atom created compounds with similar fatty odors. This shows that the methoxy group is important for the characteristic odor of anethole. We synthesized anethole derivatives where the methoxy group was replaced with a methyl group. In both methoxy- and methyl-substituted anethole derivatives, altering the 1-propenyl group changed the odors of the derivatives. Therefore, the methoxy and methyl benzene moieties are important structural features for the odor of star anise. The structural characteristics of anethole are closely related to its odor expression.
Use of (S)-trans-γ-Monocyclofarnesol as a Useful Chiral Building Block for the Stereoselective Synthesis of Diterpenic Natural Products
Authors: Serra Stefano , Cominetti Alessandra A. , Lissoni Veronica
Published: March 2019

A comprehensive study of the exploitation of ( S)- trans-γ-monocyclofarnesol as a useful chiral building block for the stereoselective synthesis of natural diterpene derivatives is here described. The farnesol derivative (+)-1 was used as starting material in the preparation of the diterpenes ( S)-dehydroambliol-A and ( S)-trixagol, as well as for the syntheses of the dinorditerpene ( S)-dinortrixagone and of the guanidine-interrupted terpenoid ( S)-dotofide. Key steps of the presented syntheses were the cross-coupling between an allyl acetate and a Grignard reagent, the Wittig reaction, the selective preparation of a diacylguanidine derivative and the alkylation of a sulfone derivative, followed by the reductive removal of the same functional group. It is worth noting that the natural products (+)-8, (+)-12 and (+)-15 were prepared stereoselectively for the first time, thus allowing the unambiguous assignment of their absolute configuration.
Seed Dormancy Breaking Diterpenoids, Including Novel Brassicicenes J and K, from Fungus Alternaria brassicicola, and their Necrotic/Apoptotic Activities in HL-60 Cells
Authors: Kenmoku Hiromichi , Takeue Sayaka , Oogushi Megumi , Yagi Yasuyuki , Sassa Takeshi , Toyota Masao , Asakawa Yoshinori
Published: March 2019

To find new metabolites similar to cotylenins and fusicoccins from the fungus Alternaria brassicicola, screening tests were carried out using the lettuce seed dormancy breaking assay. Activity-guided fractionation of the EtOAc extract from the culture using the assay afforded the isolation of two novel fusicoccane diterpenoids named brassicicenes J (1) and K (2), along with three known brassicicenes A (3), B (4), and F (5). Their structures were elucidated from extensive NMR spectral data and by comparison of these with those reported in the literature. Brassicicenes (1–5) exhibited weak to moderate seed dormancy breaking activities against lettuce seeds in the presence of abscisic acid. In addition, the necrotic/apoptotic activities of the brassicicenes (1–5), fusicoccin A (6) and cotylenin A (7) were evaluated by determining their cytotoxicity, cell viability and caspase-3/7 activation on the HL-60 cell line. Brassicicene K (2) exhibited similar cytostatic profiles to that of cotylenin A (7), and brassicicenes J (1), A (3), B (4), and F (5) exhibited necrotic activity. This is the first report of the seed dormancy breaking activity of brassicicenes in plants, and of necrotic/apoptotic activity in mammalian cells.
Cytotoxic Effects of Four Aescin Types on Human Colon Adenocarcinoma Cell Lines
Authors: Seweryn Ewa , Glehsk Michał , Środa-Pomianek Kamila , Ceremuga Ireneusz , Włodarczyk Maciej , Gamian Andrzej
Published: March 2019

Four types of aescin that are available on the pharmaceutical market, β-aescin crystalline, β-aescin amorphous, β-aescin sodium and aescin polysulfate, have been analyzed for their cytotoxic effects on human colon adenocarcinoma (LoVo) and doxorubicin-resistant human colon adenocarcinoma cell lines (LoVo/Dx). Their cytotoxic activities were evaluated by sulforhodamine B (SRB) and methyl tetrazolium (MTT) assays. All four types of aescin exerted strong dose-dependent cytotoxicity to LoVo and, to a lesser degree, LoVo/Dx cell lines. The IC50 value for the LoVo/Dx cell line was higher, but still dose-dependent. Results from both assays demonstrated that β-aescin crystalline has the most cytotoxic activity toward human colon adenocarcinoma cell lines.
Structures of Violaceusosides C, D, E and G, Sulfated Triterpene Glycosides from the Sea Cucumber Pseudocolochirus violaceus (Cucumariidae, Dendrochirotida)
Authors: Silchenko Alexandra S. , Kalinovsky Anatoly I. , Avilov Sergey A. , Andryjaschenko Pelageya V. , Dmitrenok Pavel S. , Kalinin Vladimir I. , Yurchenko Ekaterina A. , Dautov Salim S.
Published: March 2019

Four new triterpene glycosides, violaceusosides C (1), D (2), E (3) and G (4) have been isolated from the sea cucumber Pseudocolochirus violaceus (Cucumariidae, Dendrochirotida). Eight known glycosides, DS-holothurin A and holothurinoside A, isolated earlier from Holothuria forskalii (order Aspidochirotida); and violaceuside A, lefevreoside C, philinopside E, intercedenside B, violaceuside II and liovilloside A isolated earlier from representatives of the family Cucumariidae, order Dendrochirotida have also been found in P. violaceus. The chemical structures of the glycosides were elucidated by 2D NMR spectroscopy and mass spectrometry. Violaceusosides C (1), D (2), E (3) and G (4) have holostane-type aglycones and tetrasaccharide linear carbohydrate chains differing in the sugar composition and the number and position of sulfate groups. Violaceusosides E (3) and G (4) are characterized by the presence of a sulfate group at C-3 of the quinovose residue that is very rare among sea cucumber glycosides. Cytotoxic activities of the glycosides 1–4 against cells of the ascite form of mouse Ehrlich carcinoma and hemolytic activities against mouse erythrocytes have been studied. Violaceusosides C (1) and D (2) demonstrated moderate cytotoxic and hemolytic effects, while violaceusosides E (3) and G (4) have more powerful activities.
Structure-Activity Relationships of Tanshinones in Activating Nrf2. A DFT Study and Implications for Multifunctional Antioxidant Discovery
Authors: Sun You-Min , Xiao Zheng-Tao , Zhang Hong-Yu
Published: March 2019

A series of recent studies reveal that tanshinones, derived from the traditional Chinese herbal medicine Salvia miltiorrhiza Bunge, are promising multifunctional antioxidants by activating nuclear factor (erythroid-derived 2) - like 2 (Nrf2). It is thus of great interest to elucidate their structure-activity relationships (SAR) for Nrf2 activation. In this study, two theoretical parameters characterizing the electron-abstracting potential, namely, electron affinity (EA) and energy level of the lowest unoccupied molecular orbital (ELUMO), are calculated by a density functional theory (DFT) method. By these parameters, we provide a satisfactory explanation to the SAR of tanshinones for activating Nrf2, which is helpful to find new multifunctional antioxidants.
Evaluation of Bioactive Components and Antioxidant and Anticancer Properties of Citrus Wastes Generated during Bioethanol Production
Authors: Im Soon Jae , Kim Jae-Hoon , Kim Min Young
Published: March 2019

In the bioethanol production process employing citrus peels, a large amount of enzymatic hydrolyzed residues is generated as waste material. The bioactive compounds, and antioxidant and anticancer activities of these residues were investigated in the present study. Hydrolyzed citrus residues exhibited similar antioxidant activity as the unhydrolyzed control, which was positively correlated to the contents of total phenols, flavonoids and total carotenoid. Some flavonoids (naringin, naringenin, hesperetin and neohesperidin) and two high value co-products (D-limonene and galacturonic acid) were detected only in hydrolyzed residues. In addition, hydrolyzed residues showed antiproliferative activity and sub-Gl arrest in human melanoma A375 and colon cancer HCT116 cells. These results provide an alternative use for hydrolyzed citrus residues in the functional food, cosmetic and pharmaceutical industries.
ETAS, an Enzyme-treated Asparagus Extract, Attenuates Amyloid β-Induced Cellular Disorder in PC 12 Cells
Authors: Ogasawara Junetsu , Ito Tomohiro , Wakame Koji , Kitadate Kentaro , Sakurai Takuya , Sato Shogo , Ishibashi Yoshinaga , Izawa Tetsuya , Takahashi Kazuto , Ishida Hitoshi , Takabatake Ichiro , Kizaki Takako , Ohno Hideki
Published: March 2019

One of the pathological characterizations of Alzheimer's disease (AD) is the deposition of amyloid beta peptide (Aβ) in cerebral cortical cells. The deposition of Aβ in neuronal cells leads to an increase in the production of free radicals that are typified by reactive oxygen species (ROS), thereby inducing cell death. A growing body of evidence now suggests that several plant-derived food ingredients are capable of scavenging ROS in mammalian cells. The purpose of the present study was to investigate whether enzyme-treated asparagus extract (ETAS), which is rich in antioxidants, is one of these ingredients. The pre-incubation of differentiated PC 12 cells with ETAS significantly recovered Aβ-induced reduction of cell viability, which was accompanied by reduced levels of ROS. These results suggest that ETAS may be one of the functional food ingredients with anti-oxidative capacity to help prevent AD.
An Integrated Approach to the Evaluation of a Metabolomic Fingerprint for a Phytocomplex. Focus on Artichoke [Cynara cardunculus subsp. scolymus] Leaf
Authors: Fodaroni Giada , Burico Michela , Gaetano Anna , Maidecchi Anna , Pagiotti Rita , Mattoli Luisa , Traldi Pietro , Ragazzi Eugenio
Published: March 2019

The availability of reliable herbal formulations is essential in order to assure the maximal activity and to limit unwanted side-effects. The correct concentration of declared components of herbal products is a matter of health legislation and regulation, but is still a topic under debate in the field of quality control assessment. In the present work specific constituents of artichoke leaf extracts, considered as a test herbal product, were measured by standard spectrophotometric and HPLC methods (for quantitative determination of some components only), and results were correlated with the ESI-MS (showing the full metabolomic fingerprint). Phytocomplex stability over time was also investigated in batches submitted to different storage conditions. The results indicated excellent agreement between the two approaches in the measurement of total caffeoylquinic acids and chlorogenic acid contents, but the metabolomic ESI-MS method approach provides a more complete evaluation and monitoring of the composition of a herbal product, without focusing only on a single/few compound measurements. Therefore, the ESI-MS method can be proposed for the evaluation of the quality of complex matrices, such as those in a phytocomplex. Another aspect lies in the possibility to obtain a broad-spectrum stability control of herbal formulations, requiring minimal sample pre-processing procedures.
Seasonal Influence on the Essential Oil of Eucalyptus microcorys
Authors: Oliveira Flávia N. M. , Fortes Gilmara A. C. , Paula José R. , Ferri Pedro H. , Santos Suzana C.
Published: March 2019

The chemical composition of the essential oil, phenolic contents, and foliar nutrients of Eucalyptus microcorys leaves, cultivated in Brazil, was analysed on a monthly basis for one year. Canonical redundancy analysis correlated results with climate conditions (rainfall, humidity, and mean temperature), allowing three groups to be distinguished as regards temperature, flavonoids, and the content of some metals. Strong correlations between Mn, Cu, Zn, Ca, P, and K with some monoterpenes and phenolic compounds were observed. Oxygenated monoterpenes were predominant in all sampling months. Oil chemovariation may be influenced by climatic factors as well as by foliar nutrient variation.
Cladieunicellin J, a New Hydroperoxyeunicellin from Cladiella sp
Authors: Chen Tsung-Hung , Cheng Ching-Hsiao , Chen Yung-Husan , Lu Mei-Chin , Fang Lee-Shing , Chen Wu-Fu , Wen Zhi-Hong , Wang Wei-Hsien , Wu Yang-Chang , Sung Ping-Jyun
Published: March 2019

A new 6-hydroperoxyeunicellin diterpenoid, designated as cladieunicellin J (1), was isolated from an octocoral Cladiella sp., and its structure elucidated by spectroscopic methods. Compound 1 was found to exhibit cytotoxicity toward CCRF-CEM human T-cell acute lymphoblastic leukemia.
Nectandra amazonum-Derived Flavonoids as COX-1 Inhibitors: In Vitro and Docking Studies
Authors: Valdés-Barrera Iván Daniel , Cuca-Suarez Luis Enrique , Coy-Barrera Ericsson David
Published: March 2019

The ability of eleven known flavonoids isolated from Nectandra amazonum (Lauraceae) was tested for in vitro PGHS (COX) inhibition. All test compounds exhibited a dose dependent activity at different levels, exhibiting selectivity towards COX-1 inhibition. Autodock Vina was used to dock the compound structures within the active site of the PGHS-1 (PDB: 3N8V). In vitro results showed that chalcone and dihydrochalcone-related compounds exhibited reasonable inhibitory properties (IC50: 1.56-36.5 μM), with good correlation with docking results. Arg120 (or Tyr355) and Ser530 were found to be the key residues to dock the most active flavonoids, indicating such interaction might interfere with the formation of prostaglandin H2 in the active site of COX-1.
Identification and Modulatory Activity Assessment of 2-Hydroxy-3,4,6-trimethoxyacetophenone Isolated from Croton anisodontus Mull. Arg.(Euphorbiaceae)
Authors: Oliveira Maria T. A. , Teixeira Alexandre M R. , Coutinho Henrique D. M. , Menezes Irwin R. A. , Sena Diniz M. , Santos Hélcio S. , de Mesquita Bruna M , Albuquerque Maria R. J. R. , Bandeira Paulo N. , Braz-Filho Raimundo
Published: March 2019

The n-hexane extract of the stem bark of Croton anisodontus yielded 2-hydroxy-3,4,6-trimethoxyacetophenone, a well-known substance, but isolated from this species for the first time. The antimicrobial and modulatory activities of the compound towards Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Candida albicans, C krusei and C tropicalis strains were assessed. Antibiotics such as amikacin, gentamicin and neomycin were used in a subinhibitory concentration. Significant activity was observed towards P. aeruginosa and S. aureus 358, with p < 0.001 in association with amikacin. The present results place C anisodontus as an alternative source of 2-hydroxy-3,4,6-trimethoxyacetophenone with antibacterial potential.
In Vitro Cytotoxic Activity Guided Essential Oil Composition of Flowering Twigs of Stevia rebaudiana
Authors: Mann Tavleen S , Agnihotri Vijai K , Kumar Dharmesh , Pal Probir K , Koundal Rajkesh , Kumar Ashish , Padwad Yogendra S
Published: March 2019

The essential oil extracted by hydrodistillation from the flowering twigs of Stevia rebaudiana Bertoni (Asteraceae) was fractioned by chromatography. Forty-three constituents were characterized with the help of GC, GC-MS and other spectroscopic techniques. The essential oil was found to be a complex mixture of mono- and sesqui-terpenes. The cytotoxicity of the essential oil and its fractions was evaluated by sulforhodamine B (SRB) based assay against two cancer cell types viz. C-6 (rat glioma cells) and CHOK1 (Chinese hamster ovary cells). The essential oil and its fractions showed promising cytotoxicity against both cell lines. The highest activity (95.6±0.6%) was show by the essential oil on the C-6 cell line at a concentration of 400 μg/mL, which was comparable with that of the standard drug vinblastin.
An Easy Way to Pyrimidine Based Nucleoterpenes
Authors: Fiorito Serena , Genovese Salvatore , Epifano Francesco
Published: March 2019

The direct synthesis of N3 substituted pyrimidine nucleoterpenes from uridine, thymidine, and inosine with C5, C10, and C15 side chains and using DBU as the base is described. In all cases the reaction proceeded smoothly in very good yields (85–99%) affording selectively N3 substituted adducts.
Morphological, Chemical and Molecular Characterization of Centella asiatica Germplasms for Commercial Cultivation in the Indo-Gangetic Plains
Authors: Prasad Archana , Dhawan Sunita S. , Mathur Ajay K. , Prakash Om , Gupta Madan M. , Verma Ram K. , Lal Raj K. , Mathur Archana
Published: March 2019

Centella asiatica germplasm collected from north, north-eastern and southern parts of India was compared for biomass and centellosides productivity under uniform agro-climatic conditions of the Indo-Gangetic plains at Lucknow. The highest biomass accumulation (411.9 g FW/m2 area) was recorded in accession A from north India, followed by 284.0, 135.7 and 29.2 g FW/m2 in accessions M, B and E from southern, eastern and north-eastern regions, respectively. Accession M possessed the highest asiaticoside content (52.1 mg/gDW) that was 1.58, 2.34 and 21.7 folds more than accessions A, B and E, respectively. The madecassoside level in leaves of accessions B and M was comparable (28.9 and 25.7 mg/gDW) and two folds more than accession A (13.9 mg/gDW). The madecassic and asiatic acid content in leaf tissue of all four accessions remained low in Lucknow. Amplified fragment length polymorphism (AFLP) analysis with 23 primers yielded 696 fragments, 563 of which were polymorphic. Accession M out-grouped with genetic dissimilarity indices of 83, 85 and 95% from accessions A, E and B, respectively. Commercial cultivation of accessions M and A through a four months growth cycle (June to September) in agro-climatic conditions of the Indo-Gangetic plains is suggested.
Possible Role of Fat Tissue in the Pharmacokinetics of Dodeca-2E,4E,8Z,10E/Z-tetraenoic Acid Isobutylamides after Oral Administration of Echinacea angustifolia Extract in Rats
Authors: Jedlinszki Nikoletta , Rédei Dóra , Haller József , Freund Tamás F. , Hohmann Judit , Zupkó István
Published: March 2019

Alkamides are one of the most important constituents of lipophilic extracts of Echinacea angustifolia roots. These compounds play an important role in the versatile pharmacological actions of this plant. The present study aimed to compare the concentrations of isomeric dodeca-2 E,4 E,8 Z,10 E/ Z-tetraenoic acid isobutylamides (DTAI) in brain and periepididymal fat tissues and blood plasma of rats. Thirty, 60, 240 and 720 min after the oral administration of E. angustifolia root extract, tissue and plasma concentrations were determined by reversed-phase HPLC with ESI-MS/MS detection. The calculated terminal t½ of the mixture of DTAI was 8.28 h, which indicates a relatively slow elimination. In the 0.5–4 h period the brain/plasma and fat/plasma concentration ratios were continuously above 3 and 18, respectively, followed by equilibrium at 12 h. Our results indicate substantial accumulation of alkamides in lipid-rich tissues, which presumably contributes to a maintained pharmacological action.
Two Novel Iridoids from Morinda longifolia
Authors: Ban Ninh Khac , Giang Vu Huong , Linh Tran My , Lien Le Quynh , Ngoc Ninh Thi , Dat Le Duc , Thao Nguyen Phuong , Nhiem Nguyen Xuan , Cuong Nguyen Xuan , Pham Van Cuong , Nam Nguyen Hoai , Regalado Jacinto , Van Keo Huynh , Van Kiem Phan , Van Minh Chau
Published: March 2019

Six secondary metabolites, including two novel iridoids, longifolides A (1) and B (2), were isolated by various chromatographic methods from a methanol extract of branches and leaves of Morinda longifolia Craib. The structures of the compounds were determined on the basis of NMR spectroscopic (1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, NOESY) and FTICR-MS data, as well as by comparison of them with literature values.
Effect of Silitidil, a Standardized Extract of Milk Thistle, on the Serum Prolactin Levels in Female Rats
Authors: Capasso Raffaele
Published: March 2019

The aim of this study was to assess the effect of Silitidil, a standardized extract of milk thistle, on the serum levels of prolactin in female rats. A 14-day treatment with Silitidil (25–200 mg/kg, per os), a standardized extract of Silybum marianum fruits (milk thistle), increased, in a dose dependent manner, the serum prolactin levels in female rats. Galega (200 mg/kg, per os) given alone neither modified the basal levels of prolactin nor increased further serum prolactin levels when associated with Silitidil. Bromocriptine (1 mg/kg, per os) significantly reduced the high serum prolactin levels induced by Silitidil (200 mg/kg, per os). The results show that the extract of S. marianum fruits significantly increases prolactin levels in female rats; this effect is not potentiated by galega and seems to involve, at least in part, dopamine D2 receptors.
Preparative Production of Spinochrome E, a Pigment of Different Sea Urchin Species
Authors: Shestak Olga P. , Anufriev Victor Ph. , Novikov Vyacheslav L.
Published: March 2019

A concise route to spinochrome E (1) (2,3,5,6,7,8-hexahydroxy-1,4-naphthoquinone), a pigment isolated from sea urchins of different species, has been developed starting from either commercially available 5,8-dihydroxy-1,4-naphthoquinone (11) or 2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone (12). The protocol involves 3 steps, the chlorination of either 11 or 12 to tetrachloronaphthazarin (13), the total nucleophilic substitution of the chlorine atoms in 13 by methoxy groups, and hydrolysis of tetramethyl ether14; this makes possible the preparation of the target compound in overall yields from 41 to 46%.
Phenylpropanoids and Furanocoumarins as Antibacterial and Antimalarial Constituents of the Bhutanese Medicinal Plant Pleurospermum amabile
Authors: Wangchuk Phurpa , Pyne Stephen G. , Keller Paul A. , Taweechotipatr Malai , Kamchonwongpaisan Sumalee
Published: March 2019

With the objective of determining safety and verifying the traditional uses of the Bhutanese medicinal plant, Pleurospermum amabile Craib & W. W. Smith, we investigated its crude extracts and the isolated phytochemicals for their biological activities. Four phenylpropanoids [( E)-isomyristicin (1), ( E)-isoapiol (2), methyl eugenol (3) and ( E)-isoelemicin (4)] and six furanocoumarins [psoralen (5), bergapten (6), isoimperatorin (7), isopimpinellin (8), oxypeucedanin hydrate (9) and oxypeucedanin methanolate (10)] were isolated from this plant. Among the test samples, compound 10 showed weak antibacterial activity against Bacillus subtilis and best antimalarial activity against the Plasmodium falciparum strains, TM4/8.2 (chloroquine and antifolate sensitive) and K1CB1 (multidrug resistant). None of the test samples showed cytotoxicity. This study generated scientific data that support the traditional medical uses of the plant.
Quantification and Comparison of Extraction Methods for Alkaloids in Aegle marmelos Leaves by HPLC
Authors: Karmase Aniket , Prasanna K , Rasabattula Sruti , Bhutani Kamlesh K
Published: March 2019

The leaves of Aegle marmelos are reported to contain multi-bioactive classes of compounds including coumarins, furanocoumarins and alkaloids. HPLC analysis of the crude extract was challenging due to low concentrations of the compounds in the leaves. Five compounds visible in the HPLC chromatogram were separated and identified by HPLC and further elaborated for quantification as marker compounds of A. marmelos leaves using a C18 column with detection at 275 nm. A gradient mobile phase consisting of acetonitrile and water was used. The developed HPLC method showed good linearity (r2≥0.994), high precision (RSD<5%), and good recovery (99.27–99.98%) of the compounds. The lowest detection limit was 5 ng and the method was found to be robust. All the validation parameters were within the permissible limits. Therefore, the developed method is accurate and reliable for the quality control of A. marmelos. This is the first report of extensive quantitative HPLC analysis of marker compounds in A. marmelos leaves and method validation.
Biological Properties of 6-Gingerol: A Brief Review
Authors: Wang Shaopeng , Zhang Caihua , Yang Guang , Yang Yanzong
Published: March 2019

Numerous studies have revealed that regular consumption of certain fruits and vegetables can reduce the risk of many diseases. The rhizome of Zingiber officinale (ginger) is consumed worldwide as a spice and herbal medicine. It contains pungent phenolic substances collectively known as gingerols. 6-Gingerol is the major pharmacologically-active component of ginger. It is known to exhibit a variety of biological activities including anticancer, anti-inflammation, and anti-oxidation. 6-Gingerol has been found to possess anticancer activities via its effect on a variety of biological pathways involved in apoptosis, cell cycle regulation, cytotoxic activity, and inhibition of angiogenesis. Thus, due to its efficacy and regulation of multiple targets, as well as its safety for human use, 6-gingerol has received considerable interest as a potential therapeutic agent for the prevention and/or treatment of various diseases. Taken together, this review summarizes the various in vitro and in vivo pharmacological aspects of 6-gingerol and the underlying mechanisms.
1H and 13C NMR Analysis of the neo-Clerodane Diterpenoid Scutecyprin
Authors: Penchev Plamen N. , Nachkova Stefka R. , Vasileva Tonka A. , Bozov Petko I.
Published: March 2019

The 1H and 13C NMR spectra of the neo-clerodane diterpenoid scutecyprin were completely assigned by using a combination of 2D NMR experiments, which included 1H-1H COSY, HSQC, HMBC and NOESY sequences.
Analysis of Bioactive Amaryllidaceae Alkaloid Profiles in Lycoris Species by GC-MS
Authors: Guo Ying , Pigni Natalia B. , Zheng Yuhong , de Andrade Jean Paulo , Torras-Claveria Laura , de Souza Borges Warley , Viladomat Francesc , Codina Carles , Bastida Jaume
Published: March 2019

The genus Lycoris, a group of Amaryllidaceae plants distributed in temperate regions of Eastern Asia, is already known for containing representative alkaloids typical of this botanical family with a wide range of biological activities (for example, lycorine and galanthamine). In the present work, the alkaloid profiles of nine species, L. albiflora, L. aurea, L. chinensis, L. haywardii, L. incarnata, L. longituba, L. radiata, L. sprengeri, and L. squamigera, and one variety ( L. radiata var. pumila) have been evaluated by GC-MS. Structures belonging to the lycorine-, homolycorine-, haemanthamine-, narciclasine-, tazettine-, montanine- and galanthamine-series were identified and quantified, with galanthamine- and lycorine-type alkaloids predominating and usually showing a high relative abundance in comparison with other alkaloids of the extracts. Interestingly, L. longituba revealed itself to be a potential commercial source of bioactive alkaloids. In general terms, our results are consistent with the alkaloid profiles reported in the literature for previously studied species.
Induction, Cloning and Functional Expression of a Sesquiterpene Biosynthetic Enzyme, δ-Guaiene Synthase, of Aquilaria microcarpa Cell Cultures
Authors: Lee Jung-Bum , Hirohashi Syun , Yamamura Yoshimi , Taura Futoshi , Kurosaki Fumiya
Published: March 2019

A homology-based cloning strategy yielded a cDNA clone presumably encoding δ-guaiene synthase, a sesquiterpene cyclase, from tissue cultures of Aquilaria microcarpa, which were treated with methyl jasmonate. Incubation of cell cultures of the plant with yeast extract also induced transcriptional activation of the sesquiterpene synthase gene. The translated protein of the gene obtained by heterologous expression in Escherichia coli catalyzed the cyclization of farnesyl diphosphate to liberate δ-guaiene with α-guaiene and germacrene A as the minor products. The results obtained in the present study, together with the previously reported results, suggest that two classes of δ-guaiene synthase occur in Aquilaria; the enzyme proteins from A microcarpa and A sinensis liberate germacrene A as a minor product, while the protein from A. crassna generates α-humulene instead of germacrene A.