bluuebunny/crossref_metadata_2025 huggingface dataset:
A New Antioxidant Pyrano[4,3-c][2]benzopyran-1,6-dione Derivative from the Medicinal Mushroom Fomitiporia ellipsoidea
Authors: Zan Li Feng , Bao Hai Ying , Bau Tolgor , Li Yu
Published: March 2019

A new pyrano[4,3-c][2]benzopyran-1,6-dione derivative antioxidant, named phelligridin K (1), was isolated from the methanol extract of the fruiting bodies of Fomitiporia ellipsoidea, together with the known compounds, ( E)-4-(3,4-dihydroxyphenyl)but-3-en-2-one (2), hispidin (3), inoscavin C (4), and inonoblin B (5). Their structures were elucidated by means of extensive NMR and MS data analysis. Compounds 1, 4 and 5 exhibited significant scavenging activity against the ABTS radical cation.
Two New Compounds from Paeonia lactiflora
Authors: Wang QingHu , Dai Nayintai , Han Narenchaoketu , Ao Wuliji
Published: March 2019

Two new compounds, namely 5-methyl-4,2′,3′,5′-tetrahydroxy-4′-methoxy-2-aldehyde biphenyl (1) and 1,8-dioxo-1,8-dihydropyrano[3,4-c]pyran-3,6-dicarboxyl acid, diethyl ester (2), were isolated from the 95% ethanol extract of the roots of Paeonia lactiflora Pall. The structures of 1 and 2 were elucidated by spectroscopic methods, including UV, IR, HR-ESI-MS and extensive 1D and 2D NMR techniques.
Two New Ramulosin Derivatives from the Entomogenous Fungus Truncatella angustata
Authors: Chen Shenxi , Zhang Zhuowei , Li Li , Liu Xingzhong , Ren Fengxia
Published: March 2019

Two new ramulosin derivatives, 7α-hydroxy-8-dihydroramulosin (1) and 7-ketoramulosin (2), along with three known metabolites, (+)-ramulosin (3), 6-hydroxyramulosin (4), and 8-dihydroramulosin (5), were isolated from the crude extract of Truncatella angustata, an entomogenous fungus isolated from the Septobasidium-infected insect Aspidiotus sp. The structures of 1 and 2 were elucidated by nuclear magnetic resonance experiments, and 1 was further confirmed by X-ray crystallography. The absolute configuration of 1 was assigned by single-crystal X-ray diffraction analysis using Cu K α radiation, whereas that of 2 was determined by electronic circular dichroism (ECD) calculations. Compounds 1–5 were tested for cytotoxicity against four human carcinoma cell lines, HeLa, A549, MCF-7, and T24. Compound 4 showed weak cytotoxic effects against A549 and T24.
Crassaostrea gigas Oyster Shell Extract Inhibits Lipogenesis via Suppression of Serine Palmitoyltransferase
Authors: Tran Nguyen Khoi Song , Kwon Jeong Eun , Kang Se Chan , Shim Soon-Mi , Park Tae-Sik
Published: March 2019

Oysters are widely consumed seafood, but their shells impose a serious environmental problem. To extend the utilization of oyster shell waste, we investigated the biological role of oyster shell extract. In this study, we verified that the ethanol extract of oyster shell (EOS) contains taurine and betaine, the major components of oyster body. EOS downregulated transcription of Sptlc1 and Sptlc2 mRNA, the subunits of serine palmitoyltransferase (SPT). Suppression of SPT subunits reduced sphinganine and sphingomyelin by inhibiting de novo sphingolipid biosynthesis. Inhibition of sphingomyelin biosynthesis resulted in downregulation of lipogenic gene expression such as ACC, FAS, SCD1, and DGAT2. Consistent with inhibition of lipogenesis, cellular triglyceride levels were diminished by EOS, but cholesterol levels were not altered. Taken together, these results suggest that EOS has a lipid-lowering effect and could be applied as either a therapeutic or preventive measure for metabolic dysfunction.
Chemical Constituents of Essential Oils from the Leaves, Stems, Roots and Fruits of Alpinia polyantha
Authors: Huong Le T. , Thang Tran D. , Ogunwande Isiaka A.
Published: March 2019

The essential oils obtained from the leaves, stems, roots and fruits of Alpinia polyantha D. Fang (Zingiberaceae) have been studied. The leaf oil was comprised mainly of camphor (16.1%), α-pinene (15.2%) and β-agarofuran (12.9%), while the major constituents of the stem oil were α-pinene (12.4%), β-cubebene (10.6%), β-agarofuran (10.3%) and globulol (8.8%). However, β-cubebene (12.6%), fenchyl acetate (10.8%), β-maaliene (9.0%), aristolone (8.8%) and α -pinene (8.2%) were the compounds occurring in higher amounts in the root oil. The quantitatively significant compounds of the fruit oil were δ-cadinene (10.9%), β-caryophyllene (9.1%), β-pinene (8.7%) and α-muurolene (7.7%).
Anti-inflammatory Compounds from Ampelopsis cantoniensis
Authors: Van Thu Nguyen , Cuong Dao , Hung Tran Manh , Van Luong Hoang , Woo Mi Hee , Choi Jae Su , Lee Jeong-Hyung , Kim Jeong Ah , Min Byung Sun
Published: March 2019

Many natural products have been shown to have an inhibitory effect on nitric oxide (NO), and are used as chemotherapy agents for inflammation disease. The current study was designed to evaluate the anti-inflammatory activity of chemical components from the leaves of Ampelopsis cantoniensis. Sixteen compounds (1–16) were isolated and identified. Phloretin (5) and 5,7,3′,5′-tetrahydroxyflavanone (16) inhibited nitric oxide (NO) production with IC50 values of 5.2, and 18.5 μM, respectively. The inhibitory effect of compounds 5 and 16 were accompanied by dose-dependent decreases in LPS-induced nitric oxide synthase (iNOS) in RAW 264.7 cells, respectively. This study investigated the significant anti-inflammatory properties of isolated compounds from the leaves of A. cantoniensis for the first time. The findings demonstrate that A. cantoniensis could be used beneficially in the treatment of inflammation disease.
Altitudinal Variation of Flavonoid Content in the Leaves of Fallopia japonica and the Needles of Larix kaempferi on Mt. Fuji
Authors: Murai Yoshinori , Setoguchi Hiroaki , Kitajima Junichi , Iwashina Tsukasa
Published: March 2019

Ultraviolet-B radiation is harmful to plants, and its intensity increases at altitude. So plants growing at high altitude possess UV protection systems. Flavonoid is known as a major UV protectant because it absorbs UV radiation and scavenges UV-induced free radicals in plant tissues. Japanese knotweed ( Fallopia japonica) and Japanese larch ( Larix kaempferi) grow at a wide range of altitudes on Mt. Fuji, the highest mountain in Japan, while the two plants harbor a homogeneous genetic structure. In the present study, a total of 14 flavonol 3- O-glycosides were isolated from both species. Furthermore, quantitative HPLC analyses revealed that flavonoid levels in the leaves of F. japonica and the needles of L. kaempferi increased with increasing altitude of their growing sites. The altitudinal trend of UV-absorbing antioxidants of herbal and woody plants was simultaneously revealed for the first time. These results suggest that both species have chemically acclimatized to high altitude regions, in which severe environmental conditions such as higher UV radiation exist.
Flavonoids from Stellaria nemorum and Stellaria holostea
Authors: Ancheeva Elena , Daletos Georgios , Muharini Rini , Lin Wen Han , Teslov Leonid , Proksch Peter
Published: March 2019

Stellaria nemorum L. and S. holostea L. (Caryophyllaceae) were investigated for their flavonoids. The new flavonoid 6- C-[(α-arabinopyranosyl)-(1→2)- O-β-xylopyranosyl]apigenin (1) and the four known C-glycosides, 6- C-[(α-arabinopyranosyl)-(1→2)- O-β-glucopyranosyl]apigenin (2), apigenin 6- C-β-galactopyranoside-8- C-β-glucopyranoside (3), apigenin 6- C-β-glucopyranoside-8- C-α-arabinopyranoside (4), and apigenin 6- C-β-glucopyranoside-8- C-β-xylopyranoside (5) were isolated from the aerial parts of S. nemorum for the first time. Furthemore, five known flavonoids, 3,5,7-trihydroxy-3′,5′-dimethoxyflavone (9), diosmetin 6- C-β-glucopyranoside (8), schaftoside (4), isoorientin (6) and orientin (7) were obtained from the aerial parts of S. holostea. Compounds 4, 8 and 9 are reported for the first time from this species. The structures of all isolated compounds were unambiguously elucidated by one- and two- dimensional NMR and mass spectral analysis, by acid hydrolysis, as well as by comparison with literature data. The crude extracts of the investigated species exhibited antimicrobial activity against Staphylococcus aureus, while none of the isolated compounds was found to be active.
Flower Color Changes in three Japanese Hibiscus Species: Further Quantitative Variation of Anthocyanin and Flavonols
Authors: Shimokawa Satoshi , Iwashina Tsukasa , Murakami Noriaki
Published: March 2019

One anthocyanin and four flavonols were detected from the petals of Hibiscus hamabo, H. tiliaceus and H. glaber. They were identified as cyanidin 3- O-sambubioside, gossypetin 3- O-glucuronide-8- O-glucoside, quercetin 7- O-rutinoside, gossypetin 3- O-glucoside and gossypetin 8- O-glucuronide by UV spectra, LC-MS, acid hydrolysis and HPLC. The flavonoid composition was essentially the same among the petals of H. hamabo, H. tiliaceus and H. glaber, and there was little quantitative variation, except for cyanidin 3- O-sambubioside, the content of which in the petals of H. tiliaceus and H. glaber was much higher than in that of H. hamabo. Flower colors of H. tiliaceus and H. glaber change from yellow to red, and that of H. hamabo changes from yellow to orange. These changes were caused by contents of anthocyanin and flavonols, which increased after flowering of H. hamabo, H. tiliaceus and H. glaber.
Molecular Structures of the Stem Tuber Anthocyanins of Colored Potatoes and Their Coloring Effects on the Tubers
Authors: Zhao Chang Ling , Wen Guo Song , Mao Zi Chao , Xu Shao Zhong , Liu Zheng Jie , Zhao Ming Fu , Lin Chun
Published: March 2019

This paper summarized the important achievements about the general characteristics of the molecular structures of the stem tuber anthocyanins of Colored potatoes and the basic coloring effects of the anthocyanins on the tubers. The various coloration patterns of the skins and/or flesh of Colored potato tubers result from the accumulation of the anthocyanins in the periderms, phelloderms and/or peripheral cortices of the tubers, and the tuber colors are fundamentally determined by the matching profiles of the six naturally occurring anthocyanidins, i.e., cyanidin, delphinidin, malvidin, pelargonidin, peonidin and petunidin. Generally, the tuber anthocyanidins hold an O-glycosidic bond-linked rutinosyl at the C3 site, and either a glucosyl linked by an O-glycosidic bond or no substituent group may exist at the C5 site simultaneously. Furthermore, an E-monoacyl frequently exists at the C3- rutinosyls or at the C5-glucosyls of most tuber anthocyanins, and the phenolic acids acylating the tuber anthocyanins are often p-coumaric, ferulic and caffeic acids. The popular names of the p-coumaric acid derivatives of the malvidin, pelargonidin, peonidin and petunidin of the tubers are Malvanin, Pelanin, Peonanin and Petanin, respectively. This review provides a reference for the exploration of the mechanism of the tuber coloration and the identification of the molecular structures of the stem tuber anthocyanins of Colored potatoes.
Polyphenolic Compounds and Antioxidant Activities of the Leaves of Glochidion hypoleucum
Authors: Anantachoke Natthinee , Kitphati Worawan , Mangmool Supachoke , Bunyapraphatsara Nuntavan
Published: March 2019

Bioassay-guided fractionation of the methanol extract of Glochidion hypoleucum (Miq.) Boerl leaves led to the isolation of five polyphenol compounds, methyl gallate, gallic acid, apigenin-8- C-β-D-glucopyranoside (vitexin), luteolin-8- C-β-D-glucopyranoside (orientin), and luteolin-6- C-β-D-glucopyranoside (isoorientin). The chemical structures of the isolated compounds were determined using spectroscopic (NMR, UV-Vis, IR) and mass spectrometric techniques. The antioxidative properties of the methanol extract and isolated polyphenols were evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) for radical scavenging activity and 2′,7′-dichlorodihydrofluorescein diacetate (DCFH-DA) to measure the level of reactive oxygen species (ROS). With the exception of vitexin, the crude methanol extract and the polyphenol compounds inhibited DPPH radicals with IC50 values ranging from 2.46 ± 0.05 to 40.0 ± 0.3 μg/mL. In addition, the crude methanol extract attenuated H2O2-induced intracellular ROS production in a dose-dependent manner in HEK-293 cells. Gallic acid and isoorientin significantly reduced the ROS level in HEK-293 cells at a concentration of 20 μM.
Phenolic Constituents of Carex vulpinoidea Seeds and their Tyrosinase Inhibitory Activities
Authors: Niesen Daniel B. , Ma Hang , Yuan Tao , Bach Alvin C. , Henry Geneive E. , Seeram Navindra P.
Published: March 2019

Two new phenolics, a stilbenoid, vulpinoideol A (1), and a chalcone, vulpinoideol B (2), along with ten known compounds (3–12) were isolated from Carex vulpinoidea Michx. seeds. The structures of compounds 1–12 were elucidated based on spectrometric and spectroscopic analyses including HRESIMS, 1D and 2D NMR data. All compounds were evaluated for their tyrosinase enzyme inhibitory activities.
Utilization of Flavonoid Compounds from Bark and Wood: A Review
Authors: Yazaki Yoshikazu
Published: March 2019

Flavonoid compounds, which are extracted from bark and wood and used commercially, are flavan 3-ols as monomers and their polymers, which are called “condensed tannins”. Reactions of the condensed tannins with formaldehyde are the basis for wood adhesives. In the late 1940s, tannin research for wood adhesives was begun and the world-first commercial use of wattle tannin from black wattle ( Acacia mearnsii) bark as wood adhesives occurred in Australia in the 1960s. In addition, wattle tannin-based adhesives were further developed in South Africa and the uses of these adhesives have been continuing to date. The success of wattle tannin in wood adhesives is demonstrated by the collaboration of the ACIAR with the CAF in the early 1990s. Although radiata pine bark ( Pinus radiata) could be a useful resource for the production of wood adhesives, three problems prevented its use in this application: low extractive yields from the bark, variable quality of the tannin extracts and excessive viscosity of the formulated tannin adhesives. In order to overcome these problems, various extraction methods have been proposed. Studies on tannin adhesives from bark of other pine species are also described. Furthermore, the use of the tannin in the bark without extraction is described as “bark adhesives” from radiata pine and black wattle. The use of radiata tannin without formaldehyde for moulded wood products is also described. Owing to the strong antioxidant activity of flavonoid compounds, bark extracts from French maritime pine ( Pinus pinaster, synonym P. maritima) and radiata pine have been commercialized as nutritional supplements: Pycnogenol and Enzogenol, respectively. The background and the development of Pycnogenol and the basic difference in the preparation processes between Pycnogenol and Enzogenol are described. On the basis of the discovery that the SOSA value for wattle tannin is approximately 10 times that of extracts from pine bark supplements (Pycnogenol and Enzogenol), chemical, biochemical and clinical studies on wattle tannin were conducted. Results from these studies are outlined. Wattle tannin has been developed as a nutritional supplement and marketed as Acapolia in Japan.
Antiproliferative Effect of Linalool on RPMI 7932 Human Melanoma Cell Line: Ultrastructural Studies
Authors: Cerchiara Teresa , Straface SerafinaVittoria , Brunelli Elvira , Tripepi Sandro , Gallucci Maria Caterina , Chidichimo Giuseppe
Published: March 2019

Linalool, a small monoterpene molecule, is used widely for its flavoring and fragrant properties in many cosmetic products. In this work, we investigated the antiproliferative effect of two different linalool solutions on RPMI 7932 human melanoma and NCTC 2544 normal keratinocites cell lines using the trypan blue method. Morphological changes in cells were investigated by scanning electron microscopy (SEM) and transmission electron microscopy (TEM). In addition, apoptosis was evaluated using caspase 3-antibody. Linalool showed a selective inhibitory effect on the growth of melanoma cells in a concentration-dependent manner, inducing several morphological changes, as revealed by SEM and TEM analysis. Moreover, the labelling for caspase-3 is abundant in the melanoma cells and almost absent in the normal keratinocites cells. The results suggest that linalool could be used as drug and/or as model drug for developing potential therapeutic agents for melanoma.
Degradation Products of Rubusoside under Acidic Conditions
Authors: Prakash Indra , Bunders Cynthia , Devkota Krishna P. , Charan Romila D. , Hartz Rachael M. , Sears Tracy L. , Snyder Tara M. , Ramirez Catherine
Published: March 2019

A natural sweetener, Rubusoside (1), subjected to extreme pH and temperature conditions, resulted in the isolation and structural elucidation of one novel rubusoside degradant (7), together with seven known degradants (2-6 and 8-9). 1D and 2D NMR spectroscopy (1H, 13C, COSY, HSQC-DEPT, HMBC, and NOESY) and mass spectral data were used to fully characterize the degradant 7.
Synthesis of Auronol Derivatives and Their Immunostimulating Activity
Authors: Lan Phương Diep Thi , Nguyen Quoc Vuong , Vu Van Chien , Le Tuan Nguyen , Nguyen Thi Hue , Pham Thi Hang , Chau Van Minh , Pham Van Cuong
Published: March 2019

The first synthesis of alphitonin-4- O-β-D-glucopyranoside (1) was described. Since, the nitrile group, a strong hydrogen bond acceptor with a significant solvation shell, is considered to have capacity comparable to sugar for facilitating the cell membrane permeation of the molecules, several alphitonin-4- O-β-D-glucopyranoside and maesopsin-4- O-β-D-glucopyranoside analogues were prepared by replacing glucopyranose moieties with acetonitrile groups. Immunostimulating activity evaluation on lymphocyte proliferation indicated that the compound 7 with an acetonitrile group at OH-4 of alphitonin had a strong stimulation effect on lymphocyte proliferation. Interestingly, when tested against the normal cell NIH/3T3, 7 had no inhibition even at the concentration of 100 μg/mL.
Anti-Vancomycin-resistant Enterococcus faecium and E. faecalis Activities of (-)-Gossypol and Derivatives from Thespesia garckeana
Authors: Masila Veronica M. , Midiwo Jacob O. , Zhang Jin , Gisacho Bonface M. , Munayi Renee , Omosa Leonidah K. , Wiggers Frank T. , Jacob Melissa R. , Walker Larry A. , Muhammad Ilias
Published: March 2019

The root extract of Thespesia garckeana yielded three known oxidatively coupled sesquiterpenoids, namely (-)-gossypol (1) and two of its derivatives (-)-6-methoxygossypol (2) and (+)-6,6′-dimethoxygossypol (3), and the stem bark afforded ( E)-docosyl-3-(3,4-dihydroxyphenyl) acrylate (4), stigmasterol (5) and betulinic acid (6). The structures of the isolated compounds were determined on the basis of full spectral data (1D and 2D NMR and HRMS) and comparison with literature values. Compound 1 showed potent antibacterial activity against vancomycin-resistant Enterococcus faecium (VRE) with IC50/MIC/MBC values of 1.71/4.82/19.31 μM, respectively, whereas the reference standard vancomycin was found to be inactive. The mono- and di-methoxylated derivatives of this compound, (-)-6-methoxygossypol (2) and (+)-6,6′-dimethoxygossypol (3), were less active with respective IC50/MIC/MBC values of 2.73/4.70/9.40 μM and 6.14/18.32/18.32 μM against this microbe. Compound 2 was more potent than 1 against the low level VRE strain with IC50/MIC/MBC values of 4.34/9.40/9.40 μM ( vs 5.23/19.31/19.31μM for 1). This compound also showed interesting activities against Candida glabrata with an IC50 value of 2.97 μM, but was less active against methicillin-resistant S. aureus (MRSA) exhibiting an IC50 value of 17.33 μM. Compound 1 demonstrated modest activity against the other microbes tested including C. glabrata, S. aureus and MRSA with IC50 values of 0.73, 9.15 and 8.99 μM, respectively.
Coumarins from Murraya exotica Collected in Egypt
Authors: Negi Naoko , Abou-Dough Ahmad Muhamad , Kurosawa Masumi , Kitaji Yukako , Saito Keiko , Ochi Asae , Ushijima Kaori , Kusakabe Eri , Kitaguchi Yoshimi , Jinguji Yu , Teshima Naoko , Ju-ichi Motoharu , Ito Chihiro
Published: March 2019

Four new coumarins, isomurralonginol senecioate (1), isomurralonginoic acid (2), murrangatin 2′-formate (3), and meranzin hydrate 2′-palmitate (4), were isolated from the vegetative branches of Murraya exotica together with 33 known compounds. The structures of the new compounds were determined from chemical and spectroscopic data.
Chemical Composition of the Essential oil of Laserpitium latifolium from Serbia
Authors: Mitić Violeta , Stankov-Jovanović Vesna , Djordjevic Aleksandra , Ilic Marija , Simonovic Strahinja , Stojanovic Gordana
Published: March 2019

The essential oil of aerial parts of Laserpitium latifolium L. from Serbia, obtained by hydro distillation, was analyzed by GC-MS and GC-FID applying liquid injection mode; thirty-four compounds were registered (99.9% of the total oil). The essential oil clearly belongs to the monoterpenoid chemotype, with monoterpenoids constituting 99.8% of the total oil. Sabinene (47.8%), α-pinene (25.0%) and β-pinene (7.1%) were the major constituents.
Endemic Balkan Parsnip Pastinaca Hirsuta: The Chemical Profile of Essential Oils, Headspace Volatiles and Extracts
Authors: Jovanović Snežana Č. , Jovanović Olga P. , Petrović Goran M. , Stojanović Gordana S.
Published: March 2019

The present study for the first time reports the chemical composition of the endemic Balkan parsnip Pastinaca hirsuta Pančić essential oil and headspace (HS) volatiles, obtained from fresh roots, stems, flowers and fruits, as well as fresh fruits n-hexane and diethyl ether extracts. According to GC-MS and GC-FID analyses, β-Pinene was one of the major components of the root and stem HS volatiles (50.6–24.1%). ( E)-β-Ocimene was found in a significant percentage in the stem and flowers HS volatiles (31.6–57.3%). The most abundant constituent of the fruit HS, flower and fruit essential oils and both extracts was hexyl butanoate (70.5%, 31.1%, 80.4%, 47.4% and 52.7%, respectively). Apiole, accompanied by myristicin and ( Z)-falcarinol, make up over 70% of the root essential oils. γ-Palmitolactone was the major component of the stem essential oils (51.9% at the flowering stage and 45.7% at the fruiting stage). Beside esters as dominant compounds, furanocoumarins were also identified in extracts. (Dis)similarity relations of examined plant samples were also investigated by the agglomerative hierarchical cluster analysis. The obtained results show there is difference in the composition of volatile components from different plant organs, while the stage of growth mainly affects the quantitative volatiles composition.
Analgesic and Antiinflammatory Activities of the Essential Oil of the Unique Plant Zhumeria majdae
Authors: Miraghazadeh Seyyedeh Ghazal , Shafaroodi Hamed , Asgarpanah Jinous
Published: March 2019

The analgesic and anti-inflammatory properties of Zhumeria majdae essential oil were investigated in mice and rats. The analgesic activity of the oil was assessed by acetic acid-induced writhing and Eddy's hot plate methods while the acute anti-inflammatory effect was investigated by inflammatory paw edema in rat. Z. majdae oil significantly decreased the number of acetic acid-induced writhes in mice compared with animals that received vehicle only. Also it exhibited a central analgesic effect as evidenced by a significant increase in reaction time in the hot plate method. The oil also significantly reduced carrageenan induced paw edema in rats. The inhibitory activity of Z. majdae essential oil was found to be very close to that of the standard drug, diclofenac sodium (50 mg/kg). The studied oil was analyzed by GC and GC–MS and seventeen constituents were identified, representing 99.2% of the oil. The major components of the oil were characterized as linalool (63.4%) and camphor (27.5%), which might be responsible for these observed activities. The results suggest that Z. majdae essential oil possesses biologically active constituent(s) that have significant activity against acute inflammation and have central and peripheral antinociceptive effects which support the ethnomedicinal claims of the plant application in the management of pain and inflammation.
Occurrence and De novo Biosynthesis of Caffeine and Theanine in Seedlings of Tea (Camellia sinensis)
Authors: Deng Wei-Wei , Ashihara Hiroshi
Published: March 2019

Caffeine (1,3,7-trimethyl xanthine) and theanine (γ-glutamyl-L-ethylamide) are the major nitrogen-containing secondary metabolites in tea leaves. The aim of the present study was to elucidate the relative concentration and amounts of these compounds and the de novo biosynthetic activity in different parts of tea seedlings grown for 27-, 106- and 205 days. The results indicated that caffeine and its biosynthetic activity occur only in leaves and stems, while theanine is distributed in all organs, including roots. The concentration of caffeine and theanine in leaves ranged from 0.3–1.1 mg N/g and 0.1–0.5 mg N/g fresh weight, respectively. A higher concentration of theanine was found in roots (0.5–1.1 mg N). The total amounts of theanine expressed as g N/seedling were 1.1–1.5 times higher than that of caffeine. The high biosynthetic activity of caffeine from NH4+ was found in young leaves during the first 106 days after germination. Theanine biosynthetic activity probably occurs in roots, since higher 15N atom% excess was observed in roots during the first 27 days. Theanine may be synthesized mainly in roots and translocated to leaves. The de novo biosynthesis of caffeine and theanine in tea seedlings and their accumulation and translocation are discussed.
Metabolism of Purine Alkaloids and Xanthine in Leaves of Maté (Ilex paraguariensis)
Authors: Yin Yuling , Katahira Riko , Ashihara Hiroshi
Published: March 2019

Accumulation and metabolism of purine alkaloids in leaves of maté ( Ilex paraguariensis) were investigated. In winter, leaves accumulated caffeine but not theobromine, indicating that caffeine is the end product of purine alkaloid synthesis in maté. To elucidate the purine alkaloid metabolism in maté leaves, the metabolic fate of [8-14C]theobromine, [8-14C]theophylline, [8-14C]caffeine and [8-14C] xanthine was investigated in the leaf disks of young and mature leaves. In young maté leaves, significant amounts of theobromine and theophylline were utilized for caffeine biosynthesis, but the conversion was not observed in mature leaves. A small amount of theophylline was converted to theobromine. Practically no caffeine catabolism was detected in maté leaves during a 24 h-incubation. Catabolism of theobromine and theophylline via 3-methylxanthine was observed mainly in mature leaves. Xanthine was catabolised extensively via ureides in both young and mature leaves, but limited amounts are also utilized for the synthesis of theobromine, theophylline and caffeine. Possible pathways for the metabolism of purine alkaloids in maté leaves are discussed.
Effect of Caffeine on the Expression Pattern of Water-Soluble Proteins in Rice (Oryza sativa) Seedlings
Authors: Deng Wei-Wei , Sasamoto Hamako , Ashihara Hiroshi
Published: March 2019

It has been suggested that caffeine acts as an allelochemical which influences the germination and growth of plants. The effect of caffeine on the expression profiles of proteins was investigated in shoot-root axes of rice (Oryza sativa) seedlings. Two-dimensional difference gel electrophoresis combined with Matrix-Assisted Laser Desorption/Ionization Time of Flight/Time of Flight Mass Spectrometry was employed for the separation and identification of proteins. The results indicated that amounts of 51 protein spots were reduced and 14 were increased by treatment with 1 mM caffeine. Twelve rice seedling proteins were identified. Down-regulated proteins were β-tubulin, sucrose synthase, glyceraldehyde-3-phosphate dehydrogenase, reversibly glycosylated polypeptide/α-1,4-glucan protein synthase and cytoplasmic malate dehydrogenase. In contrast, up-regulated proteins were alanyl-aminopeptidase, acetyl-CoA carboxylase, adenine phosphoribosyltransferase, NAD-malate dehydrogenase, ornithine carbamoyltransferase, glucose-6-phosphate isomerase and nuclear RNA binding protein. Possible alternation of metabolism caused by caffeine is discussed with the protein expression data.
Effect of Purine Alkaloids on the Proliferation of Lettuce Cells Derived from Protoplasts
Authors: Sasamoto Hamako , Fujii Yoshiharu , Ashihara Hiroshi
Published: March 2019

To investigate the ecological role of caffeine, theobromine, theophylline and paraxanthine, which are released from purine alkaloid forming plants, the effects of these purine alkaloids on the division and colony formation of lettuce cells were assessed at concentrations up to 1 mM. Five days after treatment with 500 μM caffeine, theophylline and paraxanthine, division of isolated protoplasts was significantly inhibited. Thirteen days treatment with >250 μM caffeine had a marked inhibitory effect on the colony formation of cells derived from the protoplasts. Other purine alkaloids also acted as inhibitors. The order of the inhibition was caffeine > theophylline > paraxanthine > theobromine. These observations suggest that a relatively low concentration of caffeine is toxic for proliferation of plant cells. In contrast, theobromine is a weak inhibitor of proliferation. Possible allelopathic roles of purine alkaloids in natural ecosystems are discussed.
Isolation and Identification of an Allelopathic Substance from Hibiscus sabdariffa
Authors: Suwitchayanon Prapaipit , Pukclai Piyatida , Ohno Osamu , Suenaga Kiyotake , Kato-Noguchi Hisashi
Published: March 2019

In this study, an allelopathic substance was isolated from an aqueous methanol extract of Hibiscus sabdariffa L. by column chromatography and reverse phase HPLC. The chemical structure of the substance was determined by 1H NMR spectroscopy and mass spectrometry as trimethyl allo-hydroxycitrate. Trimethyl allo-hydroxycitrate inhibited the growth of cress hypocotyls and roots at concentrations greater than 10 mM. The concentrations required for 50% growth inhibition of the hypocotyls and roots of cress were 20.3 and 14.4 mM, respectively. The inhibitory activity of trimethyl allo-hydroxycitrate suggests that the substance may act as an allelopathic substance of H. sabdariffa.
Biosynthesis of Caffeine Underlying the Diversity of Motif B’ Methyltransferase
Authors: Nakayama Fumiyo , Mizuno Kouichi , Kato Misako
Published: March 2019

Caffeine (1,3,7-trimethylxanthine) and theobromine (3,7-dimethylxanthine) are well-known purine alkaloids in Camellia, Coffea, Cola, Paullinia, Ilex, and Theobroma spp. The caffeine biosynthetic pathway depends on the substrate specificity of N-methyltransferases, which are members of the motif B’ methyl-transferase family. The caffeine biosynthetic pathways in purine alkaloid-containing plants might have evolved in parallel with one another, consistent with different catalytic properties of the enzymes involved in these pathways.
Occurrence, Biosynthesis and Metabolism of Theanine (γ-Glutamyl-L-ethylamide) in Plants: A Comprehensive Review
Authors: Ashihara Hiroshi
Published: March 2019

Theanine (γ-glutamyl-L-ethylamide) is the most abundant non-protein amino acid in tea leaves. In addition to Camellia sinensis, theanine occurs in several plants belonging to the Ericales. Biosynthesis of theanine from glutamic acid and ethylamine by theanine synthetase is present in all organs of tea seedlings, but roots are the major site of theanine biosynthesis in adult tea trees. Theanine is transported from roots to young leaves via the xylem sap. Theanine is hydrolysed to glutamic acid and ethylamine in leaves. Ethylamine produced from theanine is predominantly used for catechin biosynthesis. Concentration of ammonia and light intensity influence the biosynthesis and degradation of theanine, respectively. Biosynthesis, translocation and degradation of theanine and related enzymes and genes are reviewed.
Chemical and Genetic Diversity of Ligularia hodgsonii in China
Authors: Kuroda Chiaki , Inagaki Kou , Chao Xun , Inoue Kyosuke , Okamoto Yasuko , Tori Motoo , Gong Xun , Hanai Ryo
Published: March 2019

Ligularia hodgsonii was found to be diverse in China. Furanoeremophilanes were isolated from samples collected in Yunnan Province, while such compounds were absent from samples from Sichuan, Gansu, and Chongqing. DNA sequencing showed that the Yunnan samples were also genetically distinct. γ-Humulene and a new bisabolane sesquiterpene were isolated.
Four New Sesquiterpenoids from Ligularia subspicata Collected in China; Isolation of a Bakkane-type Lactone, an Eremophilane-type Lactone, and Two Ortho Esters
Authors: Saito Yoshinori , Otsubo Takanori , Iwamoto Yuko , Nakashima Katsuyuki , Okamoto Yasuko , Gong Xun , Kuroda Chiaki , Tori Motoo
Published: March 2019

A bakkane type lactone, an eremophilane type lactone, and two ortho esters were isolated from Ligularia subspicata collected in Sichuan Province, China. The ortho ester type compound has been isolated from Ligularia for the first time.
Bioactive Compounds in Wild, In vitro Obtained, Ex vitro Adapted, and Acclimated Plants of Centaurea davidovii (Asteraceae)
Authors: Trendafilova Antoaneta , Jadranin Milka , Gorgorov Rossen , Stanilova Marina
Published: March 2019

In vitro cultures were initiated from a single seed of Centaurea davidovii. Whole plantlets were regenerated and cultivated for several months on agar-solidified nutrient media differing by their composition: basal MS medium, MS medium supplemented with plant growth regulators, and liquid MS medium. Plantlets were ex vitro adapted and successfully acclimated to open-air conditions; flowering was observed in some individuals in the first summer, and mass flowering during the second summer. The contents of the total flavonoids and the total phenolic compounds were determined spectrophotometrically in the leaves of the in vitro plantlets cultured on different media, and then compared with those in the leaves of the wild plants and in the leaves of the acclimated plants of the field plot. The sesquiterpene lactone 8α-(5′-hydroxyangeloyl)-salonitenolide was determined by HPLC in leaf samples of C. davidovii wild plants, in vitro obtained plantlets and ex vitro acclimated plants in the greenhouse and on the experimental field plot. The composition of the nutrient medium influenced the contents of all studied bioactive substances. The highest concentrations of all tested secondary metabolites were detected in the leaves of the acclimated plants during mass flowering, the content of the lactone reaching 56.2 mg/g DW, which was several times more than in the other leaf samples. The obtained results revealed both the effectiveness of biotechnological methods for propagation and conservation of rare and endangered plant species, and the possibility to use C. davidovii plants ex vitro acclimated to field conditions as a source of secondary metabolites with potential biological activity.
New Furanone and Sesquiterpene from the Pericarp of Calocedrus formosana
Authors: Lee Tzong-Huei , Lee Ming-Shian , Ko Horng-Huey , Chen Jih-Jung , Chang Hsun-Shuo , Tseng Mei-Hwei , Wang Sheng-Yang , Chen Chien-Chih , Kuo Yueh-Hsiung
Published: March 2019

One new γ-lactone, namely calolactone (1), together with one new drimane-type sesquiterpene, namely caloterpene (2), were isolated from the pericarp of Calocedrus formosana Florin. Their structures were elucidated by spectroscopic and mass spectrometric analysis.
The Importance of the 5-Alkyl Substituent for the Violet Smell of Ionones: Synthesis of Racemic 5-Demethyl-α-ionone
Authors: Chierici Serena , Bugoni Serena , Porta Alessio , Zanoni Giuseppe , Vidari Giovanni
Published: March 2019

The synthesis and the odor tonalities of racemic 5-demethyl-α-ionone are described. This synthetic ionone derivative did not show the typical floral-woody violet smell of α-ionone, definitely proving the importance of a suitably sized and spatially oriented alkyl substituent at C(5) for stimulating olfactory receptors of ionones.
Manoalide-related Sesterterpene from the Marine Sponge Luffariella variabilis
Authors: Hamada Toshiyuki , Harada Daisuke , Hirata Mitsunobu , Yamashita Keisuke , Palaniveloo Kishneth , Okamura Hiroaki , Iwagawa Tetsuo , Arima Naomichi , Iriguchi Toshiyuki , de Voogd Nicole J. , Vairappan Charles S.
Published: March 2019

A new manoalide-related sesterterpene, (4 E,6 E)-dehydro-25- O-methylmanoalide (1), was isolated from the organic extracts of the Bornean marine sponge Luffariella variabilis, together with the known compound (4 E,6 E)-dehydromanoalide (2). The structure of compound 1 was elucidated by interpretation of its spectroscopic data.
Germinating Seeds of Citrus aurantium a Good Source of Bioactive Limonoids
Authors: Ariza Marta R. , del Pino M. Mar Herrador , Barrero Alejandro F.
Published: March 2019

A simple method to obtain extracts enriched in bioactive limonoids from Citrus aurantium L. seeds has been developed, using solvents of increasing polarity. 1H NMR data from the extracts revealed that the highest amounts of limonoids were present in the t-butylmethylether extract. The comparison between extracts obtained from dormant and germinating seeds showed that the latter contained almost double amounts of limonoids, revealing germinating seeds as an excellent source of those bioactive compounds.
Structure Revision of Two Polyoxygenated Sterols from the Marine Sponge Neofibularia nolitangere
Authors: Yaoita Yasunori , Kikuchi Masao , Machida Koichi
Published: March 2019

Careful reexamination of the published 1H- and 13C-NMR spectral data of (24 S)-24-ethylcholest-8-ene-3β,5α,6β,7α-tetraol (1) and (24 S)-24-ethylcholest-8(14)-ene-3β,5α,6β,7α-tetraol (2), isolated from the marine sponge Neofibularia nolitangere, indicates that, in reality, compounds 1 and 2 are (24 S)-5α,6α-epoxy-24-ethylcholest-8-ene-3β,7α-diol (9) and (24 S)-5α,6α-epoxy-24-ethylcholest-8(14)-ene-3β,7α-diol (10), respectively.
Anti-Acetylcholinesterase Alkaloids from Annona glabra Leaf
Authors: Lee Shoei-Sheng , Wu Dong-Yi , Tsai Sheng-Fa , Chen Chien-Kuang
Published: March 2019

Bioassay guided fractionation and separation of the EtOH extract of Annona glabra leaf against acetylcholinesterse led to the characterization of 15 alkaloids. Among them, (–)-actinodaphnine (2) and (–)-(6a S,7 R)-7-hydroxyactinodaphnine (9) are new aporphines, although (+)-2 and (±)-2 have been found in several plants. Their structures were established by spectroscopic analysis. (-)-Anolobine (5) and (-)-roemeroline (8) showed moderate inhibitory activity against eel acetylcholinesterase with IC50 values of 22.4 and 26.3 μM, respectively.
Normonanchocidins A, B and D, New Pentacyclic Guanidine Alkaloids from the Far-Eastern Marine Sponge Monanchora pulchra
Authors: Tabakmakher Ksenya M. , Makarieva Tatyana N. , Denisenko Vladimir A. , Guzii Alla G. , Dmitrenok Pavel S. , Kuzmich Aleksandra S. , Stonik Valentin A.
Published: March 2019

New pentacyclic guanidine alkaloids, normonanchocidins A, B and D (1–3) along with the earlier known monanchocidin A were isolated from the Far-Eastern marine sponge Monanchora pulchra. Structures of 1–3 were elucidated using 1D- and 2D-NMR spectroscopic and mass spectrometric data. Compound 1 and a mixture of 2 and 3 (1:1) exhibited cytotoxic activities against human leukemia THP-1 cells with IC50 values of 2.1 μM and 3.7 μM, respectively, and against cervix epithelial carcinoma HeLa cells with IC50 of 3.8 μM and 6.8 μM, respectively.
Unusual Flavonoid Glycosides from the Hawaiian Tree Metrosideros polymorpha
Authors: Clark Benjamin R. , Pramanick Swapan , Arancon Norman , Borris Robert P.
Published: March 2019

Metrosideros polymorpha is a highly variable and widely-distributed tree native to the Hawaiian islands. We describe here the isolation of two new gossypetin derivatives and three new C-methylated flavonol glycosides, which are highly uncommon and may prove to be useful chemotaxonomic markers for the species. In addition, a wide range of known flavonoid glycosides, chalcones, and terpenoids were isolated alongside the new compounds.
Anti-inflammatory Flavonoids Isolated from Passiflora foetida
Authors: Nguyen Thi Yen , To Dao Cuong , Tran Manh Hung , Lee Joo Sang , Lee Jeong Hyung , Kim Jeong Ah , Woo Mi Hee , Min Byung Sun
Published: March 2019

In this study, we evaluated the anti-inflammatory activity of the soluble ethyl acetate fraction and chemical components of the stem bark of Passiflora foetida (Passifloraceae). Ten flavonoids (1–10) were isolated by various chromatographic techniques, and their structures were determined based on spectroscopic analyses by using nuclear magnetic resonance (NMR). Luteolin (2) and chrysoeriol (3) showed the most potent inhibition of nitric oxide (NO) production in macrophage cell line, RAW264.7, with half maximal inhibitor concentration (IC50) values of 1.2 and 3.1 μM, respectively. These compounds suppressed lipopolysaccharide (LPS)-induced inducible NO synthase (iNOS) expression at the transcription level. Our research indicates that the stem bark of P. foetida has significant anti-inflammatory properties, suggesting that its flavonoids may have anti-inflammatory benefits.
In vitro Xanthine Oxidase Inhibitory Studies of Lippia nodiflora and Isolated Flavonoids and Phenylethanoid Glycosides as Potential Uric Acid-lowering Agents
Authors: Cheng Lee-Chuen , Murugaiyah Vikneswaran , Chan Kit-Lam
Published: March 2019

Lippia nodiflora has been traditionally used for treatment of knee joint pain. Hitherto, no studies have been reported on the effective use of L. nodiflora against hyperuricemia, gout or other metabolic disorders. In this present study, L. nodiflora was examined for its ability to lower uric acid levels using an in vitro xanthine oxidase inhibitory assay. The whole plant methanolic extract was subjected to bioactivity-guided fractionation to yield 4 fractions (F1–F4). F3 displayed the highest potency and was further purified by column chromatography to afford two phenylethanoid glycosides, arenarioside (1) and verbascoside (2), and three flavonoids, 6-hydroxyluteolin (3), 6-hydroxyluteolin-7- O-glycoside (4), and nodifloretin (5). These compounds inhibited xanthine oxidase activity, with IC50 values between 7.52 ± 0.01 and 130.00 ± 2.25 μM, of which 3 was the most potent. In contrast, allopurinol, serving as a positive control, was 0.22 ± 0.00 μM. Thus, L. nodiflora, and its chemical constituents are worthy of further studies as potential anti-hyperuricemic agents.
Chemical Constituents of the Underground Parts of Iris florentina and their Cytotoxic Activity
Authors: Yokosuka Akihito , Koyama Yoshikazu , Mimaki Yoshihiro
Published: March 2019

Three new isoflavonoid glycosides (1, 5, and 9) and 10 known compounds (2–4, 6–8, and 10–13) were isolated from the underground parts of Iris florentina (Iridaceae). The structures of the new compounds were determined based on extensive spectroscopic data and the results of hydrolytic cleavage. The isolated compounds and the aglycones were evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells. Compound 12 induced apoptotic cell death in the HL-60 cells.
Anthocyanin Profile and Antioxidant Activity of Various Berries Cultivated in Korea
Authors: Bae Hong-Sook , Kim Hyun Ju , Kang Jin Hee , Kudo Rika , Hosoya Takahiro , Kumazawa Shigenori , Jun Mira , Kim Oh-Yoen , Ahn Mok-Ryeon
Published: March 2019

This study examined the anthocyanin composition and antioxidant activity of various berries cultivated in Korea: blueberry, crowberry, Korean black raspberry, mulberry, and strawberry. The anthocyanins in berries were identified by high-performance liquid chromatography (HPLC) analysis, and each component was quantitatively analyzed. Furthermore, the antioxidant activity of berries was evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical-scavenging, 2,2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation decolorization, oxygen radical absorbance capacity (ORAC), and ferric ion reducing antioxidant (FRAP) assays. The results revealed that the total content of anthocyanins in crowberry was 35.1 mg/g of extract, which was higher than that in the other four major berry species (1.9-27.7 mg/g of extract). Nineteen anthocyanins were identified in the various berries. The major anthocyanins of crowberry were cyanidin-3-galactoside and delphinidin-3-galactoside, and those from Korean black raspberry were cyanidin-3-rutinoside and cyanidin-3-sambubioside-5-rhamnoside. These two berries also had relatively strong antioxidant activity accompanied by high total polyphenol contents. Thus, consumption of crowberry and Korean black raspberry may be beneficial in reducing the risk of developing lifestyle-related chronic diseases because of their strong antioxidant activity.
Flavonoids and Phenolic Acids in Methanolic Extracts, Infusions and Tinctures from Commercial Samples of Lemon Balm
Authors: Arceusz Agnieszka , Wesolowski Marek , Ulewicz-Magulska Beata
Published: March 2019

The aim of this study was to quantify the levels of flavonoids (rutin, myricetin, quercetin, kaempferol) and phenolic acids (gallic, p-coumaric, rosmarinic, syringic, caffeic, chlorogenic, ellagic, ferulic) in lemon balm ( Melissa officinalis L.) commonly used as a culinary, aromatic and medicinal herb. A rapid and reliable HPLC procedure was developed to determine the phenolic compounds in methanolic extracts, infusions and tinctures prepared from lemon balm. Except for myricetin and quercetin, as well as ellagic, gallic and rosmarinic acids, higher levels of the analytes under study were determined in the methanolic extracts (up to 22 mg/g of dry weight, DW), than in infusions (up to 5 mg/g DW). Tinctures were the poorest in flavonoids and phenolic acids (below 550 μg/g DW), except for ellagic and rosmarinic acids, which were quantified in tinctures at higher levels (mg/g DW). To sum up, the flavonoids were extracted more effectively in the infusions and tinctures than the phenolic acids. Statistically significant correlations were found between phenolic acids, possibly owing to similar biochemical pathways of the compounds. The hierarchical cluster and principal component analyses have also shown that the samples of lemon balm could be differentiated based on the levels of flavonoids and phenolic acids.
Flavonoids and Other Phenolic Compounds in Needles of Pinus peuce and Other Pine Species from the Macedonian Flora
Authors: Karapandzova Marija , Stefkov Gjose , Cvetkovikj Ivana , Stanoeva Jasmina Petreska , Stefova Marina , Kulevanova Svetlana
Published: March 2019

Flavonoids and other phenolic compounds in young needles of four pine species, Pinus peuce, P. nigra, P. mugo and P. sylvestris from the Macedonian flora were investigated. The amount of total phenols and total flavonoids were determined using Folin-Ciocalteau and aluminum chloride assay, respectively. The obtained results revealed that the total phenolic content (TPC) and total flavonoids content (TFC) varied among different pine species ranging from 9.8 to 14.0 mg GAE/g and from 3.3 to 7.2 mg CE/g of dried plant material, respectively. Qualitative analysis of flavonoids and other phenolic components was made by a LC-DAD/ESI-MSn optimized chromatographic method. A total of 17 phenolic components were identified and classified as: acids (2), procyanidins (2) and flavonoid glycosides (13). The most prevalent components were flavonoid glycosides, especially flavonols and methylated flavonols (9). Additionally, 3 components were found as acylated flavonol glycosides with ferulic and p-coumaric acid. The last one was found not only in esterified form but also in the free form. Only one flavone-apigenin glycoside was detected. Procyanidins were identified as catechin derivatives, both dimers and trimers.