bluuebunny/crossref_metadata_2025 huggingface dataset:
Biphenyl Columns Provide Good Separation of the Glucosides of DIMBOA and DIM2BOA
Authors: Pedersen Hans Albert , Steffensen Stine Krogh , Heinrichson Kirsten , Fomsgaard Inge S.
Published: March 2019

Hydroxamic acids are important defense compounds in cereals and have been subject to extensive research. Two important hydroxamic acids in maize are 2-β-D-glucopyranosyloxy-4-hydroxy-7-methoxy-2 H-1,4-benzoxazin-3(4 H)-one (DIMBOA-glc) and its 8-methoxylated derivative (DIM2BOA-glc). The compounds are typically reported as resolved by mass spectrometry rather than chromatography, with DIM2BOA-glc quantified relative to DIMBOA-glc. Biphenyl HPLC columns, however, allow good separation of the two compounds at both the analytical and semi-preparative scale, enabling both isolation and absolute quantitation of both compounds. In combination with established sample treatment and chromatographic methods, biphenyl chromatography thus promises new possibilities for resolving benzoxazinoid glucosides.
Cytotoxic Prenylated Polyphenolic Compounds from Maackia amurensis Root Bark
Authors: Veselova Marina V. , Fedoreyev Sergey A. , Tarbeeva Darya V. , Kulesh Nadezda I. , Kalinovskiy Anatoliy I. , Kuzmich Aleksandra S. , Kim Natalia Y. , Grigorchuk Valeria P.
Published: March 2019

Two new prenylated flavanones, isomaackiaflavanone A (1), isomaackiaflavanone B (2) and a new prenylated stilbene maackiastilbene (3), along with five known flavanones were isolated from the root bark of Maackia amurensis using repeated column chromatography on silica gel, Sephadex LH-20 and octadecyl silica (ODS-A) sorbents. The structures of the new compounds were elucidated by HPLC–PDA–MS, HR-ESI-MS, 1H, 13C, 1H–1H COSY, HSQC, ROESY and HMBC NMR analyses. The cytotoxicity of compounds 1–2, 4–8 against two human cancer cell lines HeLa and SK-MEL-5 was tested using the MTS method. Compounds 4, 6 and 8 showed the strongest cytotoxic activity among the compounds tested with IC50 values of 6.5, 8.8 and 7.7 μM, against SK-MEL-5 cells and 8.2, 18.8 and 12 μM against HeLa cells, respectively.
Fermented Onions Extract Inhibits Tyrosinase and Collagenase-1 Activities as a Potential New Anti–Photoaging Agent
Authors: Jeong Eun Ju , Jegal Jonghwan , Jung Young-Suk , Chung Ki Wung , Chung Hae Young , Yang Min Hye
Published: March 2019

The bulbs of onion ( Allium cepa L.) have long been used as food and dietary supplements in the treatment of various diseases. This study aimed to investigate anti-photoaging activities of fermented onions extract rich in flavonoids such as quercetin and isoquercetin. The fermented onions extract (FOE) effectively suppressed the melanin production by inhibition of tyrosinase expression in B16F10 melanoma cells at a concentration of 100 μg/mL. Besides, the FOE exhibited down-regulation of collagenase-1 expression and up-regulation of type I collagen level in UVB-irradiated HaCaT keratinocyte cells. Hyaluronic acid production was increased to 41.11% (10 μg/mL), 107.78% (100 μg/mL), and 146.67% (200 μg/mL) compared with the UVB-irradiated control by treatment of FOE. Therapeutic attempts with FOE might be useful in preventing or treating melanin pigmentary diseases and UVB-induced wrinkle formation.
Glycosylated Flavonoids from Psidium guineense as Major Inhibitors of HIV-1 Replication in vitro
Authors: Ortega Joseph T , Estrada Omar , Serrano Maria L , Contreras Whendy , Orsini Giovannina , Pujol Flor H , Rangel Héctor R
Published: March 2019

Flavonoids are present in practically all plants and many biological activities have been described for them. The flavonoid quercetin is a common molecule for which anti-HIV activity has been demonstrated. Avicularin and guajaverin are derivatives of quercetin with a glycoside substituent in their structure. In this work, a mixture of both derivatives was purified from an extract of Psidium guinense. The mixture exhibited activity against HIV-1 in vitro, with an IC50 of approximately 8.5 μg/mL, which compares favorably with the IC50 of 53 μg/mL of quercetin. The mixture also inhibited HIV-1 reverse transcriptase (RT), with an IC50 of 7.2 μM, compared to 0.6 μM for quercetin. These results are in agreement with the in silico prediction for the interaction of these flavonoids with RT and suggest that the glycosylic moiety could favor the transport of the compound into the cell. However, the glycosidic moiety might be cleaved intracellularly, being the resultant quercetin responsible for the antiviral activity.
New Flavonoid Glycosides from the Leaves of Tribulus terrestris
Authors: Nebieridze Vazha , Skhirtladze Alexander , Kemertelidze Ether , Ganzera Markus
Published: March 2019

The structures of four new flavonoid glycosides - apiotribosides A, B, C and D (1 - 4, resp.) isolated from the leaves of Tribulus terrestris L. were identified as quercetin 3- O-β-D-apiofuranosyl-(1→2)-[β-D-apiofuranosyl-(1→6)]-β-glucopyranoside (1), quercetin 3- O-β-D-apiofuranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (2), isorhamnetin 3- O-β-D-apiofuranosyl-(1→2)-[β-D-apiofuranosyl-(1→6)]-β-D-glucopyranoside (3), and isorhamnetin 3- O-β-D-apiofuranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (4).
Two New Prenylated Isoflavonoids from Erinacea anthyllis with Antioxidant and Antibacterial Activities
Authors: Mouffouk Soumia , Marcourt Laurence , Benkhaled Mohammed , Boudiaf Kaouthar , Wolfender Jean-Luc , Haba Hamada
Published: March 2019

Two new prenylated isoflavonoids, namely Erinasone A and Erinasone B along with 19 known secondary metabolites, including twelve isoflavonoids, three polyphenols, one flavonol, two flavanones and three steroids, were isolated from the whole plant (roots and aerial parts) of Erinacea anthyllis. Structures of all isolated compounds were elucidated by spectroscopic analysis, including 1D and 2D NMR (1H, 13C, COSY, HSQC, TOCSY, HMBC and NOESY), mass spectrometry (ESI-MS), UV-Vis, measurement of optical rotation [α]D and by comparison with the literature data. The total phenolic and flavonoid contents were determined in this study. Furthermore, the antioxidant and antibacterial activities of the EtOAc and n-BuOH extracts of E. anthyllis were evaluated. These extracts exhibited moderate antibacterial and antioxidant activities. Their IC50 values were approximately 0.04 mg/mL ( n-BuOH) and 0.037 mg/mL (EtOAc). Consequently, Erinacea anthyllis is a rich source of polyphenolic compounds particularly isoflavonoids used as chemotaxonomic markers for the subfamily Papilionoideae of the family Fabaceae.
Anti-tumor and Immunomodulatory Effect of Flavonoid Extracts from Patrinia heterophylla on Cervical Carcinoma Bearing Mice
Authors: Zhang Lansheng , Wang Qingbao , Zhang ShiQiang , Yin Yong , Du Xiuping , Han Zhengxiang
Published: March 2019

Patrinia heterophylla Bunge, a traditional Chinese herb, has long been used for therapy of many kinds of diseases, including cancer. Its extract or pure compound has displayed anti-proliferative effect on cancer cells as well. However, the underlying mechanism(s) by which P. heterophylla Bunge exhibited anti-tumor activity in vivo remains to be further elucidated. Herein, we investigated the effect of total flavonoid from P. heterophylla Bunge, named as PHBF, on mice bearing cervical cancer. As a result, the oral administration of PHBF (250 and 500 mg/kg BW) had significant inhibitory effect on tumor volume and weight. In addition, PHBF treatment increased thymus index of tumor-bearing mice in a dose-dependent manner ( P<0.01). Further analysis revealed that cervical cancer cell from tumor-bearing mice treated with PHBF underwent significant apoptosis, which was accompanied by the decrease of PCNA and Bcl-2 expression and increase of Bax and cleaved caspase 3 expression. Interestingly, PHBF treatment also induced more CD4+ and CD8+ T lymphocytes in peripheral blood mononuclear cells (PBMC) of tumor-bearing mice. Furthermore, we observed that the serum level of interferon gamma (IFN-γ) and interleukin-2 (IL-2) was significant higher in mice treated with PHBF than those of control group, implicating that PHBF could function as an immunomodulatory agent. Taken together, these data suggested that PHBF harbored anti-tumor properties against cervical cancer and up-regulated immune response, therefore paving a path to develop as a potential therapeutic and preventive agent for cervical treatment.
Antioxidant, Cytotoxic and α-Glucosidase Inhibitory Activities of Compounds isolated from the Twig Extracts of Maclura fruticosa
Authors: Polbuppha Isaraporn , Maneerat Wisanu , Sripisut Tawanun , Limtharakul (née Ritthiwigrom) Thunwadee , Cheenpracha Sarot , Pyne Stephen G. , Muanprasat Chatchai , Seemakhan Sawinee , Borwornpinyo Suparerk , Laphookhieo Surat
Published: March 2019

The first phytochemical investigation of the twig extracts of Maclura fruticosa led to the isolation and identification of a new xanthone, maclurafruticosone (1), together with 14 known compounds (2–15). All compounds were elucidated using spectroscopic methods as well as through comparisons made with data reported in the literature. Some isolated compounds were evaluated for their antioxidant, α-glucosidase inhibitory and cytotoxic activities. Compound 4, 6 and 7 showed significant antioxidant activity against DPPH radicals with IC50 values ranging from 7.45–16.12 μM. Compound 4 also exhibited potent activity against ABTS•+ scavenging activity with an IC50 value of 0.55 ± 0.01 μM which was better than positive control (ascorbic acid, IC50 2.35 ± 0.17 μM). Compound 12 showed significant α-glucosidase inhibitory activity with an IC50 value of 0.02 ± 0.37 mM. Compounds 5, 6 and 12 showed weak cytotoxic activities against a colon cancer cell line with IC50 values ranging from 22.35–47.62 μM.
Synthesis and Comparative Evaluation of Polymethoxy Substituted 1,4-Naphthoquinones and their Acetyl-O-glucosides as Cytotoxic Agents
Authors: Sabutski Yuri E. , Semenova Marina N. , Yurchenko Ekaterina A. , Polonik Nikita S. , Denisenko Vladimir A. , Dmitrenok Pavel S. , Semenov Victor V. , Polonik Sergey G.
Published: March 2019

Twenty five hydroxy-, chloro- and methoxy derivatives of natural and synthetic naphthazarins and their acetylated O-glycosides were synthesized. Targeted compounds were screened as cytotoxic agents on mouse Ehrlich ascites carcinoma cells using MTT test. Chloro- and methoxy-substituted naphthoquinones as well as naphthoquinone O-acetylglucosides were the most potent with IC50 in low micromolar concentration range. Glucosidation of hydroxynaphthoquinones was shown to enhance cytotoxicity, whereas methoxylation yielded both more active and less active derivatives depending on the number and position of methoxy groups. Evaluation using a phenotypic sea urchin embryo assay suggested that naphthazarins exerted their cytotoxic effects through tubulin-unrelated mechanism.
Improvement of Blood Rheology by Extract of Asana, Pterocarpus marsupium -Suppression of Platelet Aggregation Activity and Pterostilbene, as a Main Stilbene in the Extract
Authors: Murata Kazuya , Deguchi Takahiro , Yasuda Masayuki , Endo Ryutaro , Fujita Takanori , Matsumura Shinichi , Yoshioka Yuri , Matsuda Hideaki
Published: March 2019

The decoction from a tumbler made of heartwood of the Indian kino tree (Asana, Pterocarpus marsupium, PM) was a remedy for diabetes mellitus in Ayurveda. Diabetes mellitus is a one of the lifestyle-related diseases that finally leads to the induction of fatal diseases such as arterial sclerosis and cerebral infarction. In this study, effects on blood fluidity was investigated using extract obtained from the heartwood of PM. Oral administration of the extract reduced passage time of the blood obtained from disseminated intravascular coagulation model rats. In addition, the extract inhibited the reduction of platelets, which suggests that this attributed to the inhibition of platelet aggregation. The extract also demonstrated suppressive effects on both collagen- and arachidonic acid-induced platelet aggregation. Moreover, the extract showed inhibition against cyclooxygenase. The active principle was determined to be pterostilbene by collagen-induced platelet aggregation inhibitory activity-guided purification. Pterostilbene is a derivative of resveratrol, which is known to be in red wine and to possess beneficial effects for prevention of life-style related diseases. Pterostilbene exhibited 56 and 57% inhibition on both collagen- and arachidonic acid-induced platelet aggregation at 20 μM, respectively. These results demonstrate that the extract of PM heartwood may be a promising candidate as a multifunctional agent for treating lifestyle-related diseases.
New p-Terphenyl from the Fruit of Citrullus colocynthis (Cucurbitaceae)
Authors: Rizvi Tania Shamim , Ali Liaqat , Al-Rawahi Sahar Sulaiman , Al-Harrasi Ahmed
Published: March 2019

One new substituted p-terphenyl (1) has been isolated along with the known metabolites; cucurbitacin E 2-O-β-D-glucoside (2) and α-amyrin (3) from ethyl acetate and dichloromethane fractions of fruit extract of Citrullus colocynthis. The structure of the new metabolite was elucidated by combined analysis of 1D (1H and 13C) and 2D (HSQC and HMBC correlations) NMR and MS spectral data. The known metabolites were characterized by comparison of the spectral data with those reported in literature.
Extraction, Solubility and Antimicrobial Activity of (-) Usnic Acid in Ethanol, a Pharmaceutically Relevant Solvent
Authors: Ahmad Rafi , Borowiec Paulina , Falck-Ytter Anne Bergljot , Strætkvern Knut Olav
Published: March 2019

Usnic acid (UA) is the most studied bioactive secondary metabolite from lichens. Recently, UA research has focused on its antibacterial activity. However, increased application in healthcare products of UA is hampered by low solubility in aqueous solutions. Here, we report ethanol both as an alternative extraction solvent to acetone and as a pharmaceutically relevant solvent for future formulations. Dried samples of the abundant reindeer lichen ( Cladonia stellaris) were extracted in a 23 factorial design using either ethanol or acetone, varying both time and solvent-to-dry mass ratio. In both extracts, UA was the predominant compound as shown by two-dimensional thin-layer chromatography (TLC). In a disc diffusion assay, both extracts demonstrated similar antibacterial susceptibility towards Gram-positive ( Bacillus subtilis and Staphylococcus aureus), while showing little to no activity against Gram-negative bacteria ( Escherichia coli and Pseudomonas aeruginosa). Among a range of pharmaceutically relevant solvents tested, UA was only soluble in ethanol (at concentrations up to 1–2 mg mL−1).
Inhibition of Oxidative Stress through the Induction of Antioxidant Enzymes of Pigmented Rice Bran in HEK-293 Cells
Authors: Khammanit Ruksinee , Lomarat Pattamapan , Anantachoke Natthinee , Sato Vilasinee H. , Ungsurungsie Malyn , Mangmool Supachoke
Published: March 2019

The cellular antioxidant enzymes play an essential role on the protection of oxidative stress. Pigmented rice bran is the major sources of phytochemicals and elicits antioxidant property. However, the effects of pigmented rice bran on the upregulation of cellular antioxidant enzymes are incompletely understood. In this study, we demonstrated that treatment of HEK-293 cells with pigmented rice bran extracts (200 μg/mL) from Red Hawm, Red Rose, Black Sukhothai-II, and Kum Doisaket strains significantly inhibited H2O2-induced intracellular ROS production. These pigmented rice bran extracts induced mRNA expression of glutathione peroxidase-1 (GPx-1), glutathione reductase and catalase. Additionally, treatment with these rice bran extract also increased protein expression of GPx-1 and catalase. Thus, these pigmented rice bran extracts exert the cellular antioxidant effects by decreasing ROS generation as well as increasing the production of antioxidant enzymes.
Quality Evaluation of Prunellae Spica Based on Simultaneous Determination of Multiple Bioactive Constituents Combined with Grey Relational Analysis
Authors: Liu Zi-Xiu , Hua Yu-Jiao , Wang Sheng-Nan , Zou Li-Si , Liu Xun-Hong , Zhao Hui , Yan Ying
Published: March 2019

Prunellae Spica (PS) is an important traditional Chinese herbal medicine (TCM) with massive consumption because of its therapeutical and seasoning effects. However, little attention has been paid to simultaneous analyze its bioactive components for quality control of PS based on its different growing habitats and different growth periods. In this study, the quality of PS was evaluated based on simultaneous determination of multiple bioactive components combined with grey relational analysis (GRA). A reliable method based on high-performance liquid chromatography tandem triple quadrupole mass spectrometry (HPLC-QTRAP-MS/MS) was established to simultaneously determine the contents of 21 components in PS, including 9 phenolic acids, 3 coumarins, 8 flavonoids and 1 pentacyclic triterpene. Furthermore, GRA was performed to evaluate the quality of PS samples according to the contents of these 21 components. The results showed that the quality of PS harvested on withering period, cultivated in Anhui was better than that of other PS samples. The proposed method is useful for the overall assessment on the quality of PS, and this study provides valuable information for revealing the dynamic change laws of metabolite accumulation in PS and choosing the most suitable harvesting time and genuine producing area of PS to obtain the best quality.
Isolation, Structural Characterization and Neurotrophic Activity of Alkylamides from Zanthoxylum bungeanum
Authors: Wang Yuan , Liao Zhong-Bin , Cao Rong , Li He , Wei An-Zhi , Gao Jin-Ming
Published: March 2019

Two new fatty acid amides, zanthoamides E (1) and F (2), were isolated from the pericarps of Zanthoxylum bungeanum. The structures of the two sanshool compounds were elucidated by analysis of spectroscopic data (IR, UV, HRESIMS, 1D and 2D NMR). All isolated compounds (1–9) were evaluated for nerve growth factor (NGF)-potentiating activity using PC-12 cells, and the results indicated that compound 8 (tetrahydrobungeanool) showed the strongest neurotrophic activity.
α-Glucosidase and α-Amylase Inhibitory Compounds from three African Medicinal Plants: An Enzyme Inhibition Kinetics Approach
Authors: Ibrahim Mohammed Auwal , Habila James Dama , Koorbanally Neil Anthony , Islam Md. Shahidul
Published: March 2019

The quest to find new lead compounds with anti-diabetic effects via the inhibition of α-glucosidase and α-amylase had led us to conduct bioassay guided isolation of three African medicinal plants which resulted in the identification of bicyclo[2.2.0]hexane-2,3,5-triol (1), 3β- O-acetyl betulinic acid (2) and 2,7-dihydroxy-4 H-1-benzopyran-4-one (3), as the bioactive compounds. The compounds demonstrated a significant (P < 0.05) inhibitory effect on α-glucosidase and α-amylase activities than acarbose. Steady state kinetic analysis revealed that compounds 1 and 2 inhibited both α-amylase and α-glucosidase in non-competitive patterns whilst compound 3 was an uncompetitive inhibitor of α-glucosidase and a non-competitive inhibitor of α-amylase. In conclusion, the study has identified three new active α-glucosidase and α-amylase inhibitory compounds that could have the potential to retard postprandial hyperglycemia.
Essential Oils and Compounds against Pains in Animal Studies
Authors: Schabauer Lisa , Steflitsch Wolfgang , Buchbauer Gerhard
Published: March 2019

The positive impact of essential oils and compounds has been known for a long time. Essential oils are multicomponent mixtures and obtained by steam distillation of leaves or flowers or simply by pressing orange peels for example. Due to the broad-spectrum activity, essential oils can be used for a variety of disorders like sleeping problems, colds or gastrointestinal complaints. The focus of this paper is the use of essential oils against pain in animal studies. The broad use of analgesics like NSAIDs against headaches or menstrual cramps for example, is often associated with unpleasant side effects. Essential oils may help to reduce the analgesic doses.
Antibacterial Properties of the Family Amaryllidaceae: Evaluation of Plant Extracts in vitro
Authors: Nair Jerald J. , van Staden Johannes , Bonnet Susanna L. , Wilhelm Anke
Published: March 2019

The remediation of infectious diseases is an ongoing concern in healthcare structures due to the continued loss of efficacies of existing schedules and, in particular, the poignant threat of multidrug resistance. In the search for new therapies plants have emerged as an attractive option owing to their vast chemical resources. Allied to this feature is the widespread use of plants in traditional approaches towards infectious diseases. As far as the family Amaryllidaceae is concerned, around fifty of its members are identifiable with such distinctive functions in traditional medicine. This review examines the in vitro antibacterial activities of its plant extracts and sheds light on instances where these are corroborative of the traditional usage.
Discovery and Development of Statins
Authors: Endo Akira
Published: March 2019

Mevastatin (Compactin) belonging to the statin class is a hypolipidemic agent. It was isolated from the ascomycetous fungus, Penicillium citrinum by A. Endo in the 1970s, and he discovered that it acted as 3-hydroxy-3-methyl-glutaryl (HMG)-CoA reductase inhibitor. Mevastatin is considered the first statin drug. The clinical trials on mevastatin were carried out in the late 1970s in Japan. The first commercial statin drug was lovastatin, the second statin, which was found in Aspergillus terreus by Merc and Endo, independently in 1979. Since lovastatin was commercialized, 10 statins were synthesized among which paravastatin was launched to the market by Sankyo in 1989. Pravastatin is used in the lowering of cholesterol and preventing cardiovascular disease. At present, statins are the largest-selling class of drugs currently taken by patients throughout the world. Sales for this one class of drugs on 2005 were $25 billion. Today an estimated 40 million people worldwide are taking statin drugs.
Artemisinin Story from the Balkans
Authors: Vajs Vlatka , Jokić Aleksandar , Milosavljević Slobodan
Published: March 2019

The isolation is reported of artemisinin (qinghaosu), a drug remarkably effective against malaria, from the aerial parts of Artemisia annua L. (sweet wormwood) at the Department of Chemistry, University of Belgrade (now Faculty of Chemistry), Serbia by the end of 1970, almost two years before the isolation of the same compound in China.
New Eremophilane-type Sesquiterpenes from Ligularia cymbulifera
Authors: Kato Takahiro , Hirota Hiroshi , Kuroda Chiaki , Gong Xun , Ohsaki Ayumi
Published: March 2019

From the roots of Ligularia cymbulifera collected in Yunnan Province, China, two new eremophilane-type sesquiterpenoids (1 and 2) together with ten known compounds (3–12) were obtained through the precise chemical component elucidation. The structure determination was mainly carried out with 1D and 2D NMR data.
A New Diterpenoid with a Rearranged Skeleton from Salvia prattii
Authors: Kawabe Hiroshi , Suzuki Riyo , Hirota Hiroshi , Matsuzaki Keiichi , Gong Xun , Ohsaki Ayumi
Published: March 2019

A new diterpenoid with a rearranged skeleton, prattinin A (1), was isolated along with five known compounds (2–6) from the roots of Salvia prattii. The structure of 1 bearing a methyl group at the C-5 position was established by extensive spectroscopic analyses and the absolute configuration of 1 was elucidated by comparing the calculated and experimental electronic circular dichroism (ECD) spectra. Compounds 1, 3, 4, and 5 exhibited moderate or weak cytotoxicity against HL-60 and HeLa cell lines.
Melanogenesis Inhibitory Activity of Diterpenoid and Triterpenoid Constituents from the Aerial Part of Isodon trichocarpus
Authors: Manse Yoshiaki , Ninomiya Kiyofumi , Okazaki Akane , Okada-Nishida Eriko , Imagawa Takahiro , Imamura-Mizushima Mami , Yamano Yuki , Kaname Kinji , Nakamura Sho , Morikawa Toshio
Published: March 2019

A methanol extract from the aerial part of Isodon trichocarpus (Labiatae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells (IC50 = 1.6 μg/mL). From the extract, nine diterpenoids (1–9) and four triterpenoids (10–13) were isolated. Among the isolates, enmein (1, IC50 = 0.22 μM), isodocarpin (2, 0.19 μM), nodosin (4, 0.46 μM), and oridonin (6, 0.90 μM) showed an inhibitory effect without notable cytotoxicity at the effective concentrations. These diterpenoids (1, 2, 4, and 6) inhibited the expression of tyrosinase, tyrosine-related protein (TRP)-1, and TRP-2 mRNA, which could be the mechanism of melanogenesis inhibitory activity.
Structure Revision of 5β,6β-Epoxy-(22E)-ergosta-8,22-diene-3β,7β-diol from the Gorgonian Pinnigorgia sp
Authors: Yaoita Yasunori , Machida Koichi
Published: March 2019

Careful reexamination of the published 1H- and 13C-NMR spectral data of 5β,6β-epoxy-(22 E)-ergosta-8,22-diene-3β,7β-diol (1), isolated from the gorgonian Pinnigorgia sp., indicates that, in reality, the compound is 5α,6α-epoxy-(22 E)-ergosta-8,22-diene-3β,7α-diol (2).
Sodium Dodecyl Sulfate-Polyacrylamide Gel Electrophoresis (SDS-PAGE) Analysis of Palytoxin
Authors: Abe Takahiro , Naito Takayuki , Uemura Daisuke
Published: March 2019

Many natural products have been isolated from various marine organisms. These natural products, especially huge polyol and polyether compounds, are expected to be promising drug-leads. On the other hand, the accumulation of these compounds in fish and shellfish can cause food poisoning in humans. Therefore, the development of effective methods for the detection of these compounds is important from both academic and public health perspectives. We subjected palytoxin to an SDS-PAGE analysis, which is very easy, quick, and inexpensive, to determine whether this approach could be effective for detecting huge polyol natural products. Eventually, we were able to detect a band of palytoxin by SDS-PAGE analysis, which demonstrated that SDS-PAGE could be useful for detecting polyol and polyether compounds.
Synthesis of Natural Products and the Development of Synthetic Methodology: The Case Study of (–)-Atrop-abyssomicin C
Authors: Bihelovic Filip , Vulovic Bojan , Saicic Radomir N.
Published: March 2019

During our attempt to follow the planned synthetic route to the naturally occurring antibiotic (–)- atrop-abyssomicin C, we encountered two shortcomings, which forced us to reconsider our tactics and find new methods to overcome the problems. These methods turned out to be of general applicability, as demonstrated later in total syntheses of two other natural products: (+)-allokainic acid and (-)-gabosine H. The paper provides a brief account of these endeavors.
An HPLC Method for the Quantification of Colchicine and Colchicine Derivatives in Gloriosa superba seeds
Authors: Rica Capistrano I. , Naessens Tania , Pieters Luc , Apers Sandra
Published: March 2019

An 80% ethanolic extract of Gloriosa superba L. seeds (glory lily, Colchicaceae), as well as a colchicine-poor/colchicoside-rich extract, were shown to exhibit antitumor activity in a murine model for pancreatic cancer. Phytochemical investigations of the 80% ethanolic extract led to the identification of colchicine, 3- O-demethylcolchicine, and colchicoside. The objective of this work was to develop and validate a high performance liquid chromatographic analytical method according to the ICH guidelines for the quantification of these constituents. The calibration model appeared to be linear, ranging from 2.1 μg/mL to 41.9 μg/mL. The method was shown to be precise with respect to time (RSD% of 3.1% for colchicine, 2.9% for 3- O-demethylcolchicine, and 4.7% for colchicoside, 3 days, n = 6) and with respect to the concentration (RSD% of 2.9% for colchicine, 3.0% for 3- O-demethylcolchicine and 4.1% for colchicoside, 3 levels, n = 6). The recovery of colchicine resulted in a mean recovery of 100.02% with a RSD% of 2.1%. The correction factors for colchicoside and 3- O-demethylcolchicine were determined as 1.94 and 1.20, respectively. The total amount of colchicine and colchicine derivatives found in the crude extract of G. superba was 4.6% (m/m) expressed as colchicine and the overall mean of colchicine found in the crude extract was 2.8% (m/m). By using the correction factors, the other constituents of the crude extract could also be quantified, and it was found to contain 1.5% (m/m) colchicoside and 1.3% (m/m) 3- O-demethylcolchicine.
Construction of Canthin-5,6-diones via Termolecular Condensation Reaction: Studies on Synthesis of Amarastelline A
Authors: Harada Kenichi , Yamane Hiroki , Kubo Miwa , Ohsaki Ayumi , Fukuyama Yoshiyasu
Published: March 2019

A termolecular condensation reaction of harmane, alkyl halide, and dimethyl oxalate has been developed for the construction of a variety of canthin-5,6-diones. The carbon skeleton of amarastelline A, a fluorescent canthin alkaloid, was synthesized in 99.8% yield by applying this procedure.
Antitumor Sulfur Compounds from Allium Species (Onion, Welsh Onion, and Garlic)
Authors: Nohara Toshihiro , Fujiwara Yukio
Published: March 2019

Sulfur compounds obtained from onion, Welsh onion, and garlic are reviewed. A major component (onionin A1) depressed tumor progression and metastasis in both osteosarcoma and ovarian cancer-bearing mouse models.
Microbial Transformation of Some Natural and Synthetic Aromatic Compounds by Fungi: Aspergillus and Neurospora Strains
Authors: Ghani Nurunajah Ab , Ismail Nor Hadiani , Noma Yoshiaki , Asakawa Yoshinori
Published: March 2019

Microbial transformation of chalcone (1), 4-hydroxychalcone (2) and 4′-hydroxychalcone (3), 1,1-diphenylmethane (4), 1,3-diphenylacetone (5), 1,3-diphenylpropane (6), bibenzyl (7), ( E)-stilbene (8a)- and ( Z)-stilbenes (8b), and phenylcyclohexane (9), (1 R,2 S)-1-phenyl-2-hydroxycyclohexane (9a) and (1 S,2 R)-1-phenyl-2-hydroxycyclohexane (9b), and a naturally occurring bis-bibenzyl, marchantin A (10) were performed by using Aspergillus niger TBUYN-2 and the other Aspergillus strains, and Neurospora crassa which were capable to hydrogenation and epoxidation of a conjugated double bond, and direct hydroxylation and hydroperoxidation on benzene ring, and hydroxylation and carbonization on cyclohexane ring. Aspergillus species converted chalcone (1) to dihydrochalcone (1a) almost quantitatively.
Structure of Muscariflavone A-C, Isolated from Purplish Blue Spicate Flower Petals of Muscari armeniacum
Authors: Yoshida Kumi , Azuma Kayoko , Kondo Tadao
Published: March 2019

From purplish-blue spicate flowers of muscari ( Muscari armeniacum), three new glycosylated flavones, named muscariflavone A-C (1–3), were isolated, and their structures were determined using MS and NMR analyses. All of these flavones contained the apigenin chromophore, and three to four sugar linear-chains were attached at the 7-OH of apigenin. The mixture of muscarinin A, muscariflavone A-C and aluminum ions gave a stable purplish-blue color similar to that of the petals.
In vivo Antiplasmodial and Toxicological Effects of Goniothalamus lanceolatus Crude Extracts
Authors: Zohdi Rozaini Mohd , Mukhtar Shahida Muhamad , Bihud Nur Vicky , Rasol Nurulfazlina Edayah , Ahmad Fasihuddin Badruddin , Awang Khalijah , Ismail Nor Hadiani
Published: March 2019

This study is aimed at investigating the antiplasmodial activity and acute toxicity of the methanol (MeOH) extracts of the leaves and roots, and the dichloromethane (DCM) extracts of the stem bark, leaves, and roots of Goniothalamus lanceolatus. Phytochemical analysis was then carried out on the most active extract. In vivo antiplasmodial activity was assessed using the 4-day suppressive test against Plasmodium berghei ANKA (PbANKA) in mice. The plant extracts were administered intraperitoneally (i.p.) as a single dose (30 mg/kg) starting 4 h after infection. At a dose level of 30 mg/kg (i.p.), the DCM extracts of the stem bark and leaves, and the MeOH root extracts, prolonged the survival period of infected mice compared to that of the negative control. In addition, all crude extracts, except for the DCM root extract, exhibited parasitemia suppressive activity. The highest level of parasitemia suppression was recorded in mice treated with the DCM stem bark extract at 66.3%. No mortality was observed in mice treated with the DCM extracts of the stem bark and leaves, and the MeOH extract of the leaves, indicating that the LD50 is greater than 300 mg/kg. On the other hand, both the MeOH and DCM extracts of the roots showed toxic effects at a dose of 300 mg/kg (i.p) with an 83.3% mortality rate. The results obtained indicate that the stem bark of G. lanceolatus (DCM crude extract) possesses good antiplasmodial activity against PbANKA infected mice without causing acute toxicity. Five known styrylpyrone derivatives namely goniodiol 1, 8-epi-9-deoxygoniopypyrone 2, 9-deoxygoniopypyrone 3, digoniodiol 4 and goniothalamin 5 have been isolated from the bark of Goniothalamus lanceolatus (DCM crude extract). The structures and stereochemistry of all compounds were elucidated by interpretation of spectroscopic data. This study provides a scientific basis to support the traditional use of the plant as a remedy for malaria.
Investigation of Galatella villosa and G. tatarica for Antioxidant, α-Amylase, Tyrosinase, Lipoxygenase and Xanthine Oxidase Inhibitory Activities
Authors: Özeka Gülmira , Ishmuratova Margarita , Yur Süleyman , Göger Fatih , Haliloglua Yeşim , Başer K Hüsnü Can , Özek Temel
Published: March 2019

In the present work two Galatella species, Galatella villosa Rchb.f. and Galatella tatarica (Less.) Novopokr collected from Kazakhstan were subjected to hydrodistillation to yield essential oils (EOs), and to maceration in methanol to yield extracts (MEs). The EOs and MEs were evaluated for antioxidant and in vitro inhibitory activities against α-amylase, tyrosinase, lipoxygenase and xanthine oxidase enzymes. The EOs of G. villosa and G. tatarica were investigated for chemical composition using GC-FID and GC/MS techniques. The composition of MEs was investigated with LC-MS/MS technique. Monoterpenes, β-pinene (23.6 %) and α-pinene (14.4 %) were the main constituents of G. tatarica essential oil, while the oil of G. villosa was characterized not only with monoterpene α-pinene (9.0 %), but also fatty acid, hexadecanoic acid (10.2%). 3-, 5-, 1,5- and 3,4-caffeoylquinic acids, 3-, 4- and 5-feruloylquinic acids, quercetin and its different glycosides were detected in MEs according to mass spectral data. G. tatarica (IC50=74.3 μg/mL) and G. villosa (IC50=78.5 μg/mL) extracts showed significant antioxidant activity. In the β-carotene bleaching test, the extracts demonstrated noteworthy activity (%Inh 44.46 and 41.14). The extracts scavenged ABTS radical as 1.85 mM and 1.27 mM of Trolox. In a concentration of 0.5 mg/mL, the oils showed 89% and 85% inhibition of α-amylase, while the extracts showed 86% and 78% inhibition at 2 mg/mL concentration, respectively. The EOs demonstrated noteworthy potent LOX enzyme inhibition ranging between 45% and 57%. In xanthine-xanthine oxidase model system, the extracts demonstrated the highest inhibitory potency ranging between 43% and 39%. The present work is the first contribution to the chemistry and biological activities of G. tatarica and G. villosa.
Intestinal α-Glucosidase Inhibitors in Achillea millefolium
Authors: Noda Kota , Kato Eisuke , Kawabata Jun
Published: March 2019

Achillea millefolium is a plant used as a component of anti-diabetic preparation but the bioactive compounds responsible for its use are not known. Inhibition of intestinal α-glucosidase is a preferable effect for prevention and treatment of diabetes, and A. millefolium extract showed inhibitory activity against the enzyme. Activity-guided separation of the extract gave four mono- or di-caffeoylquinic acids as the isolate. Quantitation of these four caffeoylquinic acids and the activity of the isolates suggested that these are the major contributor for the α-glucosidase inhibitory activity in the extract. However also, the presence of unidentified, minor, but potent α-glucosidase inhibitor in the isolate was also suggested.
Microwave Assisted Synthesis of p-Methoxycinnamamides and p-Methoxy-β-nitrostyrenes from Ethyl p-methoxycinnamate and Screening their Anti-inflammatory Activity
Authors: Komala Ismiarni , Supandia  , Nurhasnib  , Betha Ofa Suzanti , Yardi  , Mufidah Syarifatul , Reza Muhammad , Ali Muhamad Syahid , Aulia Nova Sari , Sutar
Published: March 2019

A new modification reaction of ethyl p-methoxycinnamate (1) to afford a series of p-methoxycinnamamide and p-methoxy-β-nitrostyrene has been developed by using the assistance of the unmodified microwave oven. The synthesized compounds were characterized by using various spectroscopic techniques and furthermore screened for their anti-inflammatory activity by using anti-denaturation of heat bovine serum albumin (BSA) method. The result of bioassay indicated that p-methoxycinnamamide derivatives and p-methoxy-β-nitrostyrenes showed interesting anti-inflammatory activity.
Transcriptome Analysis of Marchantin Biosynthesis from the Liverwort Marchantia polymorpha
Authors: Takahashi Hironobu , Asakawa Yoshinori
Published: March 2019

Marchantin A, the first characterized macrocyclic bis(bibenzyls) found in the liverwort Marchantia polymorpha shows interesting biological activities such as antifungal, antimicrobial, cytotoxic, antioxidant and muscle relaxing activity. Previously, Zenk et al. reported the phenylpropane/polymalonate pathway in the biosynthesis of the marchantins in M. polymorpha. To clear this pathway, transcriptome sequencing and digital gene expression analyses of M. polymorpha were carried out by using Illumina RNA-seq system.
A New Diphenyl Ether Glycoside from Xylosma longifolium Collected from North-East India
Authors: Swapana Ningombam , Noji Masaaki , Nishiuma Rina , Izumi Masahiro , Imagawa Hiroshi , Kasai Yuusuke , Okamoto Yasuko , Iseki Kanako , Singh Ch. Brajakishor , Asakawa Yoshinori , Umeyama Akemi
Published: March 2019

A new diphenyl ether glycoside, xylosmaloside (1), was isolated from the MeOH extract of Xylosma longifolium Clos. The structure of xylosmaloside (1) was elucidated using MS analyses, extensive 2D-homo and heteronuclear NMR data interpretation and the chemical conversions. Xylosmaloside (1) showed stronger antioxidant activity than ascorbic acid.
Two New Cyclobutane Dimers from Diospyros macrocarpa
Authors: Thieury Charlotte , Le Guével Rémy , Herbette Gaëtan , Monnier Valérie , Lebouvier Nicolas , Hnawia Edouard , Asakawa Yoshinori , Guillaudeux Thierry , Nour Mohammed
Published: March 2019

A biochemical and phytochemical study of Diospyros macrocarpa Hiern, an endemic plant of New Caledonia, was realized. Indeed, bark and leaf extracts were tested for their cytotoxic and antibiotic activities as well as for their radical scavenging properties. Methanol extracts showed promising radical scavenging activity with an IC50 value of 5.6 ± 0.9 μg/mL for the leaves and 8.1 ± 1.4 μg/mL for the barks. The ethyl acetate extract from the barks showed strong and selective activity against NCI-H727 cancer cell line with an IC50 value of 9.5 ± 0.6 μg/mL.. Two new cyclobutane dimers: macrocarpasin A (1) and B (2) (figure 1) together with six known compounds: yangonin (3), betulinic acid (4), α-amyrin (5), β–amyrin (6), loliolide (7) and oleanderolide (8) were isolated from leaf extracts. Their structures were established by 1D and 2D NMR along with HRMS analyses. Cytotoxic activities of isolated compounds were also evaluated. None of them showed interesting cytotoxicity against the seven tested cancer cell lines.
Conjugation of Vescalagin with Glucose and Phenylpropanoid: Reactions Related to the Insolubilization of Oak Wood Ellagitannins
Authors: Koga Yuki , Matsuo Yosuke , Tanaka Takashi
Published: March 2019

Vescalagin is an oak wood ellagitannin, which is biosynthesized in sapwood and insolubilized during the conversion of sapwood to heartwood. The insolubilization of this tannin was attributed to the conjugation of cell wall components, such as cellulose and lignin; however, the chemical mechanism is unclear. In this study, we examined the reactions of vescalagin with glucose and sinapylaldehyde as model experiments for the conjugation of vescalagin with cellulose and lignin, respectively. Heating vescalagin with glucose and sinapylaldehyde afforded conjugation products, the structures of which were determined by spectroscopic methods. The condensation of vescalagin with glycerol proceeded at room temperature. These results suggest that the insolubilization of vescalagin is caused by the formation of covalent bonds at the C-1 benzylic carbon of vescalagin with alcohols and α,β-conjugated carbonyl compounds.
GC/MS Fingerprinting of Solvent Extracts and Essential Oils Obtained from Liverwort Species
Authors: Ludwiczuk Agnieszka , Asakawa Yoshinori
Published: March 2019

Studies concerning chemical profiling of the volatiles present in the solvent extracts from liverworts help to determine inter- and intraspecific relationships in this plant group. Due to the fact that the liverworts are morphologically very small and it is difficult to collect their sufficient amounts, there are still a few data concerning the chemistry of essential oils. The available data indicate however, that the components present in the essential oils can be used in chemosystematic studies of these spore-forming plants. Compounds occurring in the essential oils constitute a powerful tool for studying chemical differences between or within liverwort species for which the characteristic components are mono- and sesquiterpenoids. Good results were obtained for the liverworts species from the genera Asterella, Conocephalum, Diplophyllum, Jungermannia, Lepidozia, Radula, Reboulia or Scapania.
Chemical Composition of the Essential Oil of Mentha pulegium Growing Wild in Sicily and its Activity on Microorganisms Affecting Historical Art Crafts
Authors: Casiglia Simona , Bruno Maurizio , Fontana Gianfranco , Senatore Felice
Published: March 2019

The chemical composition of the essential oil from aerial parts of Mentha pulegium L. (Linné) collected in Sicily was evaluated by GC and GC-MS. The main components were pulegone (50.6%), piperitenone (27.8%) and menthone (6.9%). Comparison of this oil with other studied oils of different populations is discussed. The oil showed good antibacterial and antifungal activities against some microorganisms that infest historical art works.
Aroma Profile and Antioxidant Activity of Essential Oil from Alpinia zerumbet
Authors: Kuraya Eisuke , Yamashiro Rui , Touyama Akiko , Nakada Shina , Watanabe Kenta , Iguchi Akira , Itoh Shigeru
Published: March 2019

The essential oil of A. zerumbet, obtained from the leaves through steam distillation, has a distinct aroma and shows antioxidant activity. In this study, we evaluated the yields, antioxidant activity, and volatile compound composition of essential oils extracted from the leaves of A. zerumbet to better understand how these characteristics may vary among individual plants, and how they may differ with location of growth and season in which leaves are harvested. Gas chromatography–mass spectrometry (GC/MS) and principal component analysis (PCA) revealed that chemical composition in each individual plant was not affected by harvest season or growth area. Furthermore, GC/MS and antioxidant activity assays revealed that although the antioxidant activity and yield of these essential oils differed significantly between individual plants and collecting seasons, there was a strong inverse correlation between the yields of essential oils and their antioxidant activity. The yield, the major volatile compound compositions, the enantiomeric ratio of the few monoterpenes, and the antioxidant activities of A. zerumbet essential oil varied significantly among individual plants, and probably reflected the genetic variability within the species. This suggests the plausibility of selecting lineages of A. zerumbet to optimize future production of valuable essential oils.
Fundamental Methods in Ellagitannin Synthesis
Authors: Yamada Hidetoshi , Hirokane Tsukasa , Ikeuchi Kazutada , Wakamori Shinnosuke
Published: March 2019

This account describes methods for synthesizing natural ellagitannins. The ellagitannins, a class of polyphenols, has a wide variety of chemical structures and biological activities. Here, we focus on three topics, which are the synthesis of the hexahydroxydiphenoyl group, construction of the hexahydroxydiphenoyl bridge, and synthesis of C–O digallates. The hexahydroxydiphenoyl group and the C–O digallates are C–C and C–O coupled galloyl groups, respectively, both group of which are the two major components of ellagitannins. By combining methods described in this account, many ellagitannins might be synthesized.
Bryophyllum pinnatum – Reverse Engineering of an Anthroposophic Herbal Medicine
Authors: Hamburger Matthias , Potterat Olivier , Fürer Karin , Simões-Wüst Ana Paula , von Mandach Ursula
Published: March 2019

Bryophyllum pinnatum (syn. Kalanchoe pinnata), a plant native to Madagascar, was introduced into anthroposophic medicine in the early 20th century. In recent years, a number of investigations were conducted on the chemical composition, pharmacological properties, and clinical efficacy of Bryophyllum. Here the phytochemistry, and pharmacological and clinical data are reviewed. With respect to pharmacology, a special focus was put on properties related to the use in anthroposophic medicine as a treatment for “hyperactivity diseases”, including preterm labor, restlessness, and sleep disorders. Recent studies suggest that B. pinnatum has also potential as a treatment option in patients suffering from overactive bladder syndrome. Tolerability of Bryophyllum is addressed, and existing toxicological data are discussed in relation to bufadienolides contained in Bryophyllum. Open questions regarding the use of Bryophyllum are also discussed.
Sixty Challenges – A 2030 Perspective on Natural Products and Medicines Security
Authors: Cordell Geoffrey A.
Published: March 2019

Natural products matter, for they are essential contributors to societal well-being and global health. Flavors, fragrances, essential oils, traditional medicines and phytopharmaceuticals, and prescription and over-the-counter products all utilize constituent materials from natural sources. However, these vast natural resources of Earth are disappearing, and climate change and market expansion by a dramatically increasing and ageing population will continue to strain plant sourcing in the decades ahead. It was with these and other considerations that the term “ecopharmacognosy” was developed as both a philosophy and a practice, and from which the necessity for a “medicines security” strategy evolved.

Extending previous presentations, a series of sixty challenges for 2030 to the status quo promotes the discussion of a different vision for the natural product sciences as applied to traditional medicines. Among the topics presented are areas for global collaborative initiatives in science and in data management, the impact of climate change on medicinal plant accessibility, the sustainability and quality of the natural products that patients receive, and the integration of new technologies, particularly the genomics of secondary metabolite biosynthesis, hand-held detection systems and artificial intelligence, and the implications of increased life expectancy on future health care needs. The presentation closes with two examples of newer approaches in drug discovery.
A New Δ-2-Carene-β-D-Glucopyranoside from Fagonia Longispina
Authors: Ourzeddine Widad , D'Ambola Massimiliano , Malafronte Nicola , León Francisco , Brouard Ignacio , Benayache Fadila , Benayache Samir
Published: March 2019

One new monoterpene Δ-2-carene-6-ol-6- O-(2’,6'-diacetyl)-β-D-glucopyranoside together with fifteen known compounds among which seven flavonoids, four terpene glucosides and four phenolic derivatives, were isolated from the leaves of Fagonia longispina Batt., an endemic species of the septentrional Sahara. Their structures were determined by NMR spectroscopy and mass spectrometry analysis.