bluuebunny/crossref_metadata_2025 huggingface dataset:
Dinimbidiol Ether, a Novel Bioactive Dimeric Diterpene from the Root Extract of Cnidoscolus souzae
Authors: García-Sosa Karlina , Aldana-Pérez Rodolfo , Moo Reyna V. Ek , Simá-Polanco Paulino , Peña-Rodríguez Luis M.
Published: March 2019

The radical scavenging assay-guided fractionation of the root extract of Cnidoscolus souzae resulted in the isolation and identification of a novel bioactive dimeric diterpene with an ether linkage which has been designated as dinimbidiol ether (2). Evaluation of the antioxidant activity using the DPPH reduction assay showed that 2 is the most active metabolite in the crude extract of the plant.
Chemical Constituents from Walsura pinnata (Meliaceae)
Authors: Mahdzir Mohamad A. , Shilpi Jamil A. , Mahmud Norfaizah , Ramasamy Sujatha , Awang Khalijah
Published: March 2019

A phytochemical study on the bark of Walsura pinnata has led to the isolation of a new oleanane triterpene acid, 3-oxo-olean-9(11),12-dien-28-oic acid (1), together with nine known compounds (2–10). Their structures were established on the basis of the detailed spectroscopic analysis, including one- and two-dimensional NMR, ESI-MS and HR-ESI-MS techniques. Compounds 2, 3, 5, 6 and 8 were isolated from W. pinnata for the first time. Compounds 3 and 4 showed in vitro growth inhibitory activity against two human cancer cell lines MCF-7 and SK-OV-3 with IC50 values within the range of 8.85 - 18.28 μg/mL. To the best of our knowledge, this is the first report on the cytotoxic activity of compound 3 towards both cancer cell lines.
Chelidonine and Homochelidonine Induce Cell Death through Cell Cycle Checkpoints and MAP Kinase Pathways
Authors: Havelek Radim , Seifrtova Martina , Kralovec Karel , Habartova Klara , Cahlikova Lucie , Rezacova Martina
Published: March 2019

This study focuses on the comparative in vitro cytotoxicity of chelidonine and homochelidonine on human cancer and non-cancer cells. Both alkaloids produced a decrease in cellular growth in a dose-dependent manner exhibiting greater potency in cancer cells. The growth inhibitory effect was evidenced in both ovarian carcinoma A2780 and lung fibroblast MRC-5 cells by inducing G2 and mitotic phase cell cycle arrest. Results indicated that the extent of apoptosis induced by chelidonine and homochelidonine was correlated to sensitivity to the antiproliferative activity of the evaluated compounds. Western blotting suggested that the cellular toxicological mechanism of chelidonine is related to the differential upregulation of phospho-Chk2, p21Cip1/Waf1, phospho-ERK1/2 and phospho-p38 in various cell types, leading to alternations in the suppression of proliferation and either induction or prevention of apoptosis. Chelidonine showed the more potent effects and also affected the cell cycle checkpoints and MAPK signaling pathways within cells.
Further Antinociceptive Properties of Naringenin on Acute and Chronic Pain in Mice
Authors: Dallazen Jorge L. , da Silva Carla F. , Hamm Leticia , Córdova Marina M. , Santos Adair R. S. , Werner Maria Fernanda P. , Baggio Cristiane H.
Published: March 2019

Naringenin (NG) is a flavanone abundant in grapefruit and other citrus fruits that presents several pharmacological effects, such as antioxidant, anti-inflammatory, analgesic, among others. We investigated the antinociception of systemic administration of naringenin (NG) and some of the mechanisms of action underlying its effect. Intraperitoneal administration of NG (10 mg/kg) inhibited the mechanical allodynia induced by partial sciatic nerve ligation (PSNL) and carrageenan in 65 ± 4 and 43 ± 9% (2 h), respectively. NG also reduced the writhes number (30 mg/kg: 90 ± 9%) and the nociceptive response of formalin (100 mg/kg: 75 ± 12%, inflammatory phase), bradykinin (30 mg/kg: 79 ± 6%) and prostaglandin E2 (100 mg/kg: 98 ± 1%). Besides, NG reduced the glutamate-induced nociception with ID50 value of 66 mg/kg, effect that was reversed by naloxone. NG, at antinociceptive doses, did not affect the locomotor activity. Our findings demonstrated that systemic NG exerts anti-allodynic activity in neuropathic pain model and antinociceptive effect in several chemical and inflammatory models of nociception, with participation of glutamatergic and opioid system.
Amidochromenes for Promising Antileishmanial Activity
Authors: Neghra Abdelhak , Lecsö Marylin , Butel Marie-José , Espindola Laila S. , Deguin Brigitte , Seguin Elisabeth
Published: March 2019

Numerous natural products having a 2,2-dimethylchromene (2,2-dimethylbenzopyrane) structural element present interesting biological activities that may, therefore, be considered as privileged pharmacophore. Nine aliphatic and aromatic amides were synthesized from the 5-amino-7-methoxy-2,2-dimethyl-2 H-chromene synthon. The antibacterial, antifungal, antileishmanial and cytotoxic activities of all amidochromenes were evaluated. No antibacterial or antifungal activity was observed. Nevertheless, three aromatic amides compounds shown significant antileishmanial activity with an excellent selectivity index.
Two Diarylundecanones Isolated from Ardisia tenera
Authors: Lu Chong-Yu , Li Hong-Xiang , Li Sha , Qiu Ling , Yu Si , Cao Zhi-Xing , Guo Da-Le , Deng Yun
Published: March 2019

Ardisinones G-H (1–2), two new diarylundecanones, were isolated from the ethanol extract of aerial parts of Ardisia tenera Mez. Their structures were elucidated by interpretation of the spectroscopic evidence. The isolated compounds were evaluated for cytotoxicity against four cell lines (MV4–11, MCF-7, HCT116 and A549) and displayed moderate inhibitory activities.
Cytotoxic Compounds from the Stem Bark of Calophyllum soulattri
Authors: Lim Chan-Kiang , Hemaroopini Subramaniam , Say Yee-How , Jong Vivien Yi-Mian
Published: March 2019

Chemical investigation of the stem bark of Calophyllum soulattri resulted in the isolation of a new phloroglucinol, namely calosubellinone (1) along with two known compounds, garsubellin B (2) and soulattrone A (3). The structures of these compounds were established on the basis of spectroscopic methods. Compounds 1 and 2 displayed growth inhibitory activities against HeLa cancer cells comparable to the positive control cisplatin, with IC50 values of 19.3 and 16.5 μM, respectively. In addition, compound 2 also showed antiproliferative activity against a MDA-MB-231 cancer cell line with an IC50 value of 17.7 μM. Compounds 1 and 2 were found to exhibit good cancer-specific cytotoxicity when tested against noncancerous HEK293 cells. These findings have highlighted the therapeutic potential of compounds 1 and 2 as anticancer agents.
Synthesis and Cytotoxic Evaluation of Glucoconjugated Ethylmompain Derivatives
Authors: Pokhilo Natalia D. , Atopkina Lyubov N. , Kiseleva Marina I. , Denisenko Vladimir A. , Anufriev Victor Ph.
Published: March 2019

Quinone-carbohydrate conjugates of ethylmompain, a pigment of the sea urchin Echinothrix diadema, and its chlorinated analog were synthesized. The cytotoxic activity and contraceptive properties of the synthesized compounds have been investigated using the sperm and eggs of the sea urchin Strongylocentrotus intermedius.
Stereoselective Total Syntheses of (3R,5R)-Sonnerlactone and (3R,5S)-Sonnerlactone
Authors: Ghanty Supriya , Khan P. Rasvan , Reddy B. V. Subba
Published: March 2019

A highly convergent and concise total syntheses of (3 R,5 R)-Sonnerlactone and (3 R,5 S) Sonnerlactone from a readily available L-malic acid is described. The following series of reactions such as Barbier allylation, photochemical esterification and Ring Closing Metathesis (RCM) are utilized as key steps to accomplish their syntheses.
Phytochemical Constituents from the Root of Luvunga Scandens and Biological Activity Evaluation
Authors: Sirinut Prangchanok , Petchkongkeaw Awanwee , Romsaiyud Jariya , Prateeptongkum Saisuree , Thongyoo Panumart
Published: March 2019

Isobutylglucosinolate (1) was isolated from the root of Luvunga scandens (Roxb.) for the first time, which demonstrated an antioxidant activity with an IC50 value of 30.1±0.2 μg/mL Additionally, two biological active phytosterols, named β-sitosterol (2) and stigmasterol (3) were also isolated from Luvunga scandens (Roxb.), showing the low cytotoxicity against human colon adenocarcinoma cell line (HT29) with IC50 values of 124±1 μg/mL and 141±3 μg/mL, respectively. The chemical structure of all isolated compounds (1–4) was identified by spectroscopic analyses.
Chemical Profile of Essential Oils and Headspace Volatiles of Chaerophyllum hirsutum from Serbia
Authors: Petrović Goran M. , Stamenković Jelena G. , Stojanović Gordana S. , Mitić Violeta D. , Zlatković Bojan K
Published: March 2019

The present study reports the chemical composition on the headspace volatiles and essential oils obtained from fresh roots, shoots and inflorescences of Chaerophyllum hirsutum. In headspace samples, the most dominant class was monoterpene hydrocarbons, but the main compounds were different. The root had β-phellandrene as the major compound. Sabinene was the main component in the shoots volatiles, while the inflorescence was dominated by endo-fenchyl acetate. The composition of the essential oils of the aerial parts and the oil obtained from root was found to be quite different. The root essential oil showed the presence of phenolic compounds (13.2%), while in the oils from the aerial parts these compounds were present in very small amounts (0.1% in the shoots and 0.2% in the inflorescences oil). In total, 70 compounds were identified in the oil isolated from the root, with γ-terpinene (15.8%) as the major compound of the oil. In the oils isolated from the shoots and the inflorescences, for which 55 and 69 compounds were identified, respectively, the main class was represented by oxygenated sesquiterpenes with acorenone B as the main component, representing 57.0% of the shoots and 44.6% of the inflorescences.
1-Deoxynojirimycin: Sources, Extraction, Analysis and Biological Functions
Authors: Wang Niannian , Zhu Feifei , Chen Keping
Published: March 2019

1-Deoxynojirimycin (DNJ), a natural polyhydroxylated piperidine alkaloid, is attracting growing attention due to its important biological functions. This paper introduces the discovery and origins of DNJ, its extraction, purification, and physiological functions in the treatment of diabetes. The mechanisms of DNJ in the inhibition of fat accumulation and tumor cell metastasis are also discussed. In addition, the prospects and challenges of DNJ for practical production are proposed. This work aims to provide technical advice on obtaining DNJ and a fuller understanding of its biological activities.
Fungal Biotransformation of Cyclademol and Antimicrobial Activities of Its Metabolites
Authors: Kiran Ismail , Özşena Özge , Can Başer K Hüsnü , Demirci Fatih
Published: March 2019

Cyclademol (1) was converted for the first time to 1-(4-hydroxy-3,3-dimethylcyclohexyl) ethanone (2) and 4-(1-hydroxyethyl)-2,2-dimethylcyclohexanol (3) with 31.2 and 15.1% yields by Aspergillus niger and Neurospora crassa, respectively. The resulting metabolite structures were established by FT-IR, MS and NMR spectroscopic studies, respectively. In addition, the in vitro antimicrobial activities of the substrates and metabolites were evaluated comparatively both by using agar dilution and microdilution methods. The minimum inhibitory concentrations (MIC) of the tested compounds against a panel of pathogenic bacterial strains ranged from 1000 - 4000 μg/mL, whereas the MIC values against fungal strains were between 500 −1000 μg/mL.
Anti-allergic and Cytotoxic Effects of Sesquiterpenoids and Phenylpropanoids Isolated from Magnolia biondii
Authors: Nguyen Thi Tuyet Mai , Nguyen Thi Thu , Lee Hyun-Su , Lee Bomi , Min Byung Sun , Kim Jeong Ah
Published: March 2019

Ten sesquiterpenoids (1-10) and six phenylpropanoid derivatives (11-16) were isolated from the flower buds of Magnolia biondii Pamp. Their structures were determined by 1D- and 2D-NMR spectroscopy, mass spectrometry, and optical rotation. To evaluate their anti-allergic properties, the inhibitory effect of each isolate (1-16) on interleukin-2 (IL-2) gene expression was examined in Jurkat T cells. Among the isolated compounds, three sesquiterpenoids (2, 5, and 7) and two monoterpenoids (12 and 13) strongly inhibited IL-2 production in Jurkat T cells. Four compounds, (-)-parthenolide (2), eudesm-4(15)-eno-1β,6α-diol (5), biondinin D (12), and tiliroside (16), showed cytotoxicity against Jurkat T cells. In addition, (-)-parthenolide (2) exhibited cytotoxicity against the human cervical cancer HeLa cell line, the human breast cancer MCF-7, and human promyelocytic leukemia HL-60 cell lines.
Complete Structure Elucidation of New Steviol Glycosides Possessing 9 Glucose Units Isolated from Stevia rebaudiana
Authors: Prakash Indra , Hong Sangphyo , Ma Gil , Bunders Cynthia , Devkota Krishna P. , Charan Romila D. , Ramirez Catherine , Snyder Tara M.
Published: March 2019

In our continued effort to discover new diterpene glycoside sweeteners from Stevia rebaudiana Bertoni with a better taste profile than that of rebaudioside M, we have isolated three novel steviol glycosides with 9 glucose units, 3 at the C-13 site of the aglycone backbone and 6 at the C-19 site. Compounds 2-4 contain an additional tri-glucosyl unit attached to the C-19 glycoside region of rebaudioside M. For compounds 2 and 3 this unit is attached via the relatively rare 1→6 α-glycoside linkage. For compound 4 this additional unit is attached via the uncommon 1→3 α-glycoside linkage. In this paper, we describe the complete structure elucidation of novel diterpene glycosides with 9 sugar moieties by NMR (1H, 13C, COSY, HSQC-DEPT, HMBC, 1D TOCSY, NOESY) and mass spectral data.
Synthesis and Cytotoxic Evaluation of Betulin–Triazole–AZT Hybrids
Authors: Anh Dang Thi Tuyet , Giang Le Nhat Thuy , Hien Nguyen Thi , Cuc Dinh Thi , Thanh Nguyen Ha , Ha Nguyen Thi Thu , Chinh Pham The , Van Tuyen Nguyen , Van Kiem Phan
Published: March 2019

Betulin was converted to the corresponding alkyne-functionalized esters and amides and subsequently deployed as substrates for a ‘click’ chemistry-mediated coupling with 3'-azido-3'-deoxythydimine (AZT) to furnish a novel betulin–triazole–AZT hybrid compounds. Eleven new hybrids were thus successfully prepared and evaluated as cytotoxic agents, revealing an interesting anticancer activity in KB and HepG2 cancer cell lines.
Triterpene Saponins from Wisteria floribunda “macrobotrys” and “rosea”
Authors: Champy Anne-Sophie , Mitaine-Offer Anne-Claire , Paululat Thomas , Papini Anna-Maria , Lacaille-Dubois Marie-Aleth
Published: March 2019

Five oleanane-type saponins were isolated from two cultivars of Wisteria floribunda (Willd.) DC. (Fabaceae): From the roots of Wisteria floribunda “macrobotrys”, one new oleanane derivative elucidated as 3- O-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosyl-22- O-acetyl-3p,22p,24-trihydroxyolean-12-en-30-oic acid, and two known glycosides, and from the roots of Wisteria floribunda “rosea”, two known ones. Their structures were elucidated by a detailed 600 MHz NMR analysis including 1D and 2D NMR (1H, 13C, COSY, TOCSY, ROESY, HSQC, HMBC) experiments and mass spectrometry. Chemotaxonomic conclusions were proposed.
Magnumosides B3, B4 and C3, Mono- and Disulfated Triterpene Tetraosides from the Vietnamese Sea Cucumber Neothyonidium (= Massinium) magnum
Authors: Silchenko Alexandra S. , Kalinovsky Anatoly I. , Avilov Sergey A. , Kalinin Vladimir I , Andrijaschenko Pelageya V. , Dmitrenok Pavel S. , Chingizova Ekaterina A. , Ermakova Svetlana P. , Malyarenko Olesya S. , Dautova Tatyana N.
Published: March 2019

Two new monosulfated triterpene glycosides, magnumosides B3 (1) and B4 (2) and one new disulfated triterpene glycoside, magnumoside C3 (3) have been isolated from the tropical Indo-West Pacific sea cucumber Neothynidium (=Massinium) magnum (Phyllophoridae, Dendrochirotida) collected in the Vietnamese shallow waters. The structures of the glycosides were elucidated by 2D NMR spectroscopy and mass-spectrometry. All the isolated glycosides are characterized by the non-holostane type aglycones having 18(16)-lactone and 7(8)-double bond and differing from each other by the side chains structures and the quantity of sulfate groups in the carbohydrate chains. The cytotoxic activity of the compounds 1–3 against mouse spleen lymphocytes and ascite form of mouse Ehrlich carcinoma cells, human colorectal carcinoma DLD-1 as well as their hemolytic effects have been studied. Magnumoside B4 (2) greatly suppressed the colony formation and decreased the size of colonies of DLD-1 cancer cells at non-cytotoxic concentrations. The study on synergism of effects of radiation and compounds 1–3 on proliferation of DLD-1 cells showed that the tested compounds almost equally enhanced antiproliferative effect of radioactive irradiation.
Chemical Analysis of the Edible Mushroom Tricholoma populinum: Steroids and Sulfinyladenosine Compounds
Authors: Kovács Bernadett , Béni Zoltán , Dékány Miklós , Orbán-Gyapai Orsolya , Sinka Izabella , Zupkó István , Hohmann Judit , Ványolós Attila
Published: March 2019

Ten compounds have been identified in the methanol extract of cottonwood mushroom ( Tricholoma populinum J.E. Lange), 9 of them for the first time in this species. Besides adenosine (8) and nicotinamide (7) the isolated compounds were ergostane type steroids (1-6) and rare sulfinyladenosine constituents (9 and 10). The chemical structures of these compounds were elucidated by means of extensive spectroscopic methods (NMR and MS). Compounds 3-6 were evaluated for their potential antiproliferative activity against human cancer cell lines using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The xanthine oxidase (XO) inhibitory activity of 7-10 has been examined by spectrophotometric method. Cerevisterol (3), its methylated derivative (5) and 3-glycoside of ergosterol peroxide (6) showed significant antiproliferative activity on human breast cancer cell lines.
Chemical Constituents of the Aerial Parts of Santolina chamaecyparissus and Evaluation of Their Antioxidant Activity
Authors: Labed Fatiha , Masullo Milena , Cerulli Antonietta , Benayache Fadila , Benayache Samir , Piacente Sonia
Published: March 2019

Santolina chamaecyparissus is an aromatic evergreen herb growing in North Africa and near the Mediterranean coasts of Southern Europe. Literature data focused mainly on the investigation of the essential oil content of the aerial parts of S. chamaecyparissus, but few is known on the chemical composition of its polar extract. Total phenolic content was determined by the Folin-Ciocalteau method and the antioxidant activity of the n-butanol and chloroform fractions of S. chamaecyparissus was tested by Trolox equivalent antioxidant capacity (TEAC) and diphenyl-2-picrylhydrazyl radical (DPPH•) assays. Difference of the phenolic content and of the antioxidant activity between the two extracts prompted us to investigate their chemical composition. Five compounds, eupatilin (1), circimaritin (2), 4’-hydroxy-5,6,7-trimethoxyflavone (3), 1,3-propanediol,2-amino 1-(4-hydroxy-3-methoxyphenyl) (4) and luteolin (5) have been isolated from the chloroform extract, while the investigation of butanolic extract led to the isolation of seven compounds, prunasin (6), luteolin 7- O-β-D-glucopyranoside (7), syringoside (8), junipeionoloside (9), citroside A (10), lonicerin (11) and apigenin 7- O-β-D-neohesperidoside (12). Their structures were elucidated by extensive spectroscopic methods including 1D- (1H, 13C and TOCSY) and 2D-NMR (DQF-COSY, HSQC, HMBC) experiments as well as ESIMS analysis.
Phenolic Composition of Leaf extracts of Ailanthus altissima (Simaroubaceae) with Antibacterial and Antifungal Activity Equivalent to Standard Antibiotics
Authors: Poljuha Danijela , Sladonja Barbara , Šola Ivana , Dudaš Slavica , Bilić Josipa , Rusak Gordana , Motlhatlego Katlego E , Eloff Jacobus N
Published: March 2019

Extracts of fresh and dry Ailanthus altissima leaves from Croatia were evaluated for their phenolic composition, antioxidant and antimicrobial activities. The methanolic extract had a higher concentration of total phenolics, flavonoids and non-flavonoids, as well as a higher antioxidant capacity than water extracts. Flavonoids identified in A. altissima leaves belong to two groups: flavones (glycosides of apigenin and luteolin) and flavonols (glycosides of quercetin and kaempferol). They were mainly present as glycosides, quercetin-3- O-glucoside was the predominant flavonoid. Only traces of aglycones were detected even after extract hydrolysis. Caffeic acid was the predominant phenolic acid both before and after hydrolysis, followed by chlorogenic acid after hydrolysis. The concentration of chlorogenic acid significantly increased soon after tissue fragmentation suggesting this compound is involved in rapid response against mechanical wounding in A. altissima. Therefore, to increase the chlorogenic acid concentration, mechanical wounding could be applied. The acetone leaf extract was as active against Escherichia coli as the positive control gentamicin. Both acetone and methanol:dichloromethane extracts had a higher activity against Candida albicans than a standard drug amphotericin B. Therefore, A. altissima could serve as a valuable resource for antimicrobial activity, which makes this species interesting for further investigation and possible pharmaceutical application.
Non-alkaloid Constituents from Mahonia bealei
Authors: Van Thanh Bui , Van Anh Nguyen Thi , Giang Do Hoang , Dang Nguyen Hai , Anh Luu Dam Ngoc , Van Huong Bui , Phuong Ngo Duc , Dat Nguyen Tien
Published: March 2019

A phytochemical investigation of an ethyl acetate fraction of Mahonia bealei trunks led to the isolation of three new and four known compounds. By means of NMR and MS spectroscopic methods, the structure of the new compounds was elucidated as bishexadecyl epiphyllate (1), 3-(4-hydroxy-3,5-dimethoxyphenyl)-3-ethoxy-2-sulfopropane-1-ol (2), and 6α-acetoxystigmastan-3β-ol (3).
Zingerone Suppresses the Shedding of Endothelial Protein C Receptor
Authors: Lee In-Chul , Kim Dae Yong , Bae Jong-Sup
Published: March 2019

Zingerone (ZGR), a phenolic alkanone found in Zingiber officinale, has been reported to have various pharmacological activities including anti-inflammatory and anti-apoptotic activities. The endothelial cell protein C receptor (EPCR) plays an important role in the cytoprotective pathway and activation of protein C EPCR can be shed from the cell surface, which is mediated by tumor necrosis factor-α converting enzyme (TACE). However, little is known about the effects of ZGR on EPCR shedding. We investigated this by monitoring the effects of ZGR on phorbol-12-myristate 13-acetate (PMA)-, tumor necrosis factor (TNF)-a, and interleukin (IL)-1p-induced EPCR shedding in human umbilical vein endothelial cells (HUVECs), and cecal ligation and puncture (CLP)-mediated EPCR shedding in mice, as well as by analyzing the underlying mechanisms. Here, ZGR triggered potent inhibition of PMA-, TNF-α-, IL-1β-and CLP-induced EPCR shedding through the inhibition of phosphorylation of mitogen-activated protein kinases (MAPKs) such as p38, janus kinase (JNK), and extracellular signal-regulated kinase (ERK) 1/2. ZGR also inhibited PMA-induced TACE expression and activity in HUVECs, suggesting that p38, ERK1/2, and JNK could be molecular targets of ZGR. These results demonstrate the potential of ZGR as an agent against PMA- and CLP-mediated EPCR shedding.
Suppressive Effects of Sulforaphane on TGFBIp-mediated Sepsis
Authors: Lee In-Chul , Bae Jong-Sup
Published: March 2019

Sulforaphane (SFN) is produced when the enzyme myrosinase transforms glucoraphanin upon damage to the plant such as from chewing and effective in preventing carcinogenesis, diabetes, and inflammatory responses. Transforming growth factor β-induced protein (TGFBIp) is an extracellular matrix protein whose expression in several cell types is greatly increased by TGF-β. TGFBIp is released by human umbilical vein endothelial cells (HUVECs) and functions as a mediator of experimental sepsis. We hypothesized that SFN could reduce TGFBIp-mediated severe inflammatory responses in human endothelial cells and mice. Here, we investigated the anti-septic effects and underlying mechanisms of SFN against TGFBIp-mediated septic responses. SFN effectively inhibited lipopolysaccharide-induced release of TGFBIp and suppressed TGFBIp-mediated septic responses. In addition, SFN suppressed cecal ligation and puncture (CLP)-induced sepsis lethality and pulmonary injury. In conclusion, SFN suppressed TGFBIp-mediated and CLP-induced septic responses. Therefore, SFN could be a potential therapeutic agent for treatment of various severe vascular inflammatory diseases via inhibition of the TGFBIp signaling pathway.
In Vivo and In Vitro Evidence for the Antihyperuricemic, Anti-inflammatory and Antioxidant Effects of a Traditional Ayurvedic Medicine, Triphala
Authors: Sato Vilasinee Hirunpanich , Sungthong Bunleu , Nuamnaichati Narawat , Rinthong Prasob-orn , Mangmool Supachoke , Sato Hitoshi
Published: March 2019

The objectives of the present study were to demonstrate the antihyperuricemic effect of triphala, a formulation of traditional Ayurvedic medicine, in potassium oxonate-induced hyperuricemic mice in vivo, and to examine its inhibitor effects on xanthine oxidase (XOD), inflammatory mediators and DPPH radicals in vitro. The water extract of triphala was determined to contain the total phenolics and total flavonoids of 317.6 ± 9.2 mg GAE/g and 7.73 ± 0.26 mg QE/g, respectively. Oral administrations of triphala significantly reduced the plasma uric acid levels of potassium oxonate-induced hyperuricemic mice at doses of 1,000 and 1,500 mg/kg, as compared with control ( p<0.05). Moreover, both doses of triphala treatments markedly inhibited the formation of uric acid due to inhibition of XOD activity in liver homogenates extracted from the hyperuricemic mice by about 70-80%. Lineweaver-Burk analysis of enzyme-kinetic data showed that triphala exhibited non-competitive inhibition on XOD activity in vitro with an inhibitory constant (Ki) of 590 μg/mL. Furthermore, triphala significantly suppressed the mRNA expressions of COX-II, TNF-α and iNOS in LPS-stimulated RAW 264.7 cells, as compared with control ( p <0.05), and decreased the expression of TGF-β. IC50 values for inhibition of DPPH radical formation was calculated to be 21.9 ± 2.50 μg/mL. Antioxidant activities of triphala were determined to be 0.81 ± 0.07 g TEAC/g and 6.78 ± 0.29 mmol/100g, respectively, as assessed by ABTS and FRAP assays. In conclusion, this study provided in vivo and in vitro mechanistic evidence for the antihyperuricemic, antioxidative and anti-inflammatory effects of triphala for the first time, rationalizing its therapeutic usage for the treatment of hyperuricemia of gout.
Comparison of Volatiles of Sideritis caesarea Specimens Collected from Different Localities in Turkey
Authors: Günbatan Tuğba , Demirci Betül , Gürbüz İlhan , Demircib Fatih , Özkanc Ayşe Mine Gençler
Published: March 2019

Sideritis caesarea H. Duman, Aytaç & Başer of the Lamiaceae is an Anatolian endemic species, and is mainly used as herbal tea and folk medicine. This present study aimed to determine and compare the chemical compositions of the volatile components of S. caesarea specimens collected from different localities in Kayseri province, Turkey: Sariz town (samples A and B), Pınarbaşı-Kaynar (sample C) and Pınarbaşı-Şirvan Mountain (sample D), respectively. Initially, the essential oils of the aerial parts were obtained by hydrodistillation and analysed both by gas chromatography-flame ionization detector (GC-FID), gas chromatography/mass spectrometer (GC/MS), simultaneously. Major volatile components of samples A and D were characterized as hexadecanoic acid (19.7 and 20.5%), caryophyllene oxide (6.7 and 20.2%), β-caryophyllene (6.5 and 12.6%), respectively. In sample B, hexadecanoic acid (14.6%), β-caryophyllene (11.5%) and caryophyllene oxide (8.3%) were detected as the major components. Whereas caryophyllene oxide (13.7%), hexadecanoic acid (8.5%) and spathulenol (6.1%) were the main components of the essential oil of sample C. Besides the chemical profiling, in vitro antimicrobial effects of samples were evaluated against a panel of six pathogenic microorganisms. Inhibition zones of the tested samples varied against bacteria with low to moderate activity, where no susceptibility against Candida albicans was observed.
Chemical Composition of Essential Oil among Seven Populations of Zanthoxylum armatum from Himachal Pradesh: Chemotypic and Seasonal Variation
Authors: Bhatt Vinod , Sharma Sushila , Kumar Neeraj , Sharma Upendra , Singh Bikram
Published: March 2019

Essential oil from the fresh leaf of Zanthoxylum armatum, collected from the different regions of Himachal Pradesh, India, was obtained by hydrodistillation. The main constituents of essential oil, as well as locational and seasonal change in its composition have been determined by GC-FID and GC-MS techniques. Thirty-five constituents, making up about 93.1-99.4% of the total composition of oil, were characterized. Among all the characterized components, non-terpenic hydrocarbons (2-undecanone and ( E)-2-decanal), oxygenated monoterpenes (linalool, 1,8-cineol and β-terpineol) and monoterpene hydrocarbons ( β-phellandrene, α-pinene, sabinene and β-myrcene) contribute to major proportion of oil. Further, principal component analysis was carried out to distinguish the variation of essential oil composition among the collected samples in summer and winter season. Based on the cluster separation, five chemotypes were identified, representing β-phellandrene/2-undecanone; linalool/2-undecanone; linalool; 2-undecanone; 2-undecanone /1,8-cineol.
Composition, in vitro Antibacterial and Anti-mildew Fungal Activities of Essential Oils from Twig and Fruit Parts of Eucalyptus citriodora
Authors: Su Yu-Chang , Hsu Kuang-Ping , Ho Chen-Lung
Published: March 2019

In this study, antibacterial and anti-mildew fungal activities of the twig and fruit essential oil and its constituents from Eucalyptus citriodora were investigated in vitro against eight bacteria and seven mildew fungi, respectively. The major ingredient responsible for the antibacterial and anti-mildew fungal activities were also identified. The essential oil from the fresh twigs and fruits of E. citriodora were isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC–FID and GC–MS, respectively. The twig oil consisted primarily of 1,8-cineole (17.7%), p-cymene (17.1%), caryophyllene oxide (13.8%), and isopulegol (12.2%); the fruit oil's main constituent was p-cymene (23.2%), α-pinene (16.1%), α-cadinol (11.5%), and τ-cadinol (8.4%). In addition, comparing the antibacterial and anti-mildew fungal activities of the oils showed that the fruit oil was the most effective. For the antibacterial and anti-mildew fungal activities of the fruit oil, the active source compounds were determined to be τ-cadinol and τ-cadinol.
Methoxyflavones from Marcetia taxifolia as HIV-1 Reverse Transcriptase Inhibitors
Authors: Ortega Joseph T , Serrano María Luisa , Suárez Alírica I , Baptista Jani , Pujol Flor H , Rangel Héctor R
Published: March 2019

Methoxyflavones are flavonoid widely distributed in plants and has been reported as potent antitumor agents and some of them have shown activity against HIV-1. In this work, two methoxyflavones isolated from Marcetia taxifolia were evaluated in vitro and in silico as HIV-1 inhibitors. Pentamethoxyflavone (5,3’-dihydroxy-3,6,7,8,4’-pentamethoxyflavone) (PMF) and Hexamethoxyflavone (5-Hydroxy-3,6,7,8,3’,4’-hexamethoxyflavone) (HMF) showed activity against HIV-1. The EC50 for HMF was 0.05 μM and 0.04 μM for PMF. The methoxyflavones also inhibited HIV-1 reverse transcriptase (RT), with an IC50 of 4.1 μM for HMF and 0.4 μM for PMF. PMF exhibited an IC50 lower than nevirapine (1.4 μM). These results are in agreement with the in silico prediction for the interaction of these flavonoids with RT. Furthermore, the effect of some methoxyflavones with different patterns of methoxylation was evaluated on RT activity in a virtual screening; found that the inhibitory activity was inversely proportional to the degree of methoxylation.
Antioxidant Activity and Upregulation of Antioxidant Enzymes of Phenolic Glycosides from Aquilaria crassna Leaves
Authors: Supasuteekul Chonlakan , Nuamnaichati Narawat , Mangmool Supachoke , Likhitwitayawuid Kittisak , Tengamnuay Parkpoom , Putalun Waraporn , Sritularak Boonchoo
Published: March 2019

The leaves of Aquilaria crassna Pierre ex Lecomte (Thymelaeaceae) have been used in the traditional medicine and consumed as a health-promoting tea in several Asian countries. This study investigated the antioxidant activity of three major bioactive constituents of A. crassna leaves, genkwanin 5- O-β-primeveroside (1), iriflophenone 3,5- C-β-D-diglucoside (2) and iriflophenone 3- C-β-D-glucoside (3) using DPPH and superoxide scavenging assays, as well as their effects on induction of mRNA and protein expressions of antioxidant enzymes in HEK-293 cells. The benzophenone glycoside 3 exhibited significant scavenging activity against both types of free radicals and increased the mRNA expression of antioxidant enzymes such as glutathione peroxidase-1, glutathione reductase and heme oxygenase-1 in HEK-293 cells. In addition, all three compounds also increased the protein expression of glutathione peroxidase-1. These findings revealed the effects of these compounds at cellular level, and might be useful for the development of A. crassna leaves as supplements for prevention of oxidative stress.
Anti-proliferative Activities of Two Flavonols with Unsubstituted B-ring from the Leaves of Platanus acerifolia
Authors: Chen Hui-Feng , Huang Ri-Zhen , Zuo Bo , Ji Lan-Ju , Mo Zhi-Jian , Liao Zhi-Xin
Published: March 2019

The anti-proliferative activities against five cancer cell lines of two flavonols (1, 2) with unsubstituted B ring isolated from the ethanol extract of the leaves of Platanus acerifolia were investigated. The results showed that compound 1 possessed a noteworthy anti-proliferative activity against MGC-803 cells with an IC50 value of 17.26±1.04 μM, and compound 2 was less active than 1 with an IC50 value of 20.29±1.37 μM compared with 41.94±1.58 μM for the positive control group. In addition, the results of Hoechst 33258 staining, AO/EB staining and annexinV-FITC assays indicated that 1 caused a significant MGC-803 cellular apoptosis in a dose-dependent manner. The further mechanisms showed that compound 1 induced the production of ROS, decreased the mitochondrial membrane potential, and altered pro- and anti-apoptotic proteins, leading to activation of caspase-9 and caspase-3 in the process of cellular apoptosis. The present investigation indicated that compound 1 could be used as a potential anti-cancer candidate.
Inhibition of Lipoxygenase and Peroxidase Reaction by Some Flavonols and Flavones: The Structure-Activity Relationship
Authors: Sroka Zbigniew , Sowa Alina , Dryś Andrzej
Published: March 2019

Some flavonoids were investigated for their effects on lipoxygenase and peroxidase. The strongest inhibitor of lipoxygenase was kaempferol with one hydroxyl group situated at the 4’ position in the B ring, with activity of 21.2±2.03 calculated per μmole of compound. The weakest inhibition was observed for diosmetin with a hydroxyl group at the 3′ position and a methoxyl group at 4′ in the B ring, with activity of 1.17±0.77 per μmole.

Peroxidase was most strongly inhibited by quercetin (22.7±0.05) with two hydroxyl groups in the B ring at 3′ and 4′. The weakest inhibitor of peroxidase was genkwanin (0±0.16) with one hydroxyl group at position 4′ in the B ring and methoxyl at position 7 in the A ring. The correlation coefficient between reduction of Fe3+ by flavonoids and inhibition of lipoxygenase by these compounds was 0.72 and the reduction of Fe3+ and inhibition of peroxidase was 0.24. The results show that inhibition of peroxidase is weakly associated with reducing properties of phenols and inhibition of lipoxygenase may be associated with antioxidant properties of flavonoids.
Quercetin-3-O-glucoside Improves Glucose Tolerance in Rats and Decreases Intestinal Sugar Uptake in Caco-2 Cells
Authors: Torres-Villarreal Denys , Camacho Alberto , Milagro Fermín I. , Ortiz-Lopez Rocío , de la Garza Ana Laura
Published: March 2019

Flavonoid-rich foods intake has been associated with lower risk of non-communicable chronic diseases. Quercetin is the most abundant flavonoid in nature (fruits, vegetables, leaves and grains) as well as the most consumed flavonol. This study aims to investigate the potential effects of its conjugated form quercetin-3- O-glucoside (or isoquercetin) on glucose metabolism in rats and Caco-2 cells. To analyse the effect of quercetin-3- O-glucoside on postprandial hyperglycemia, an oral glucose tolerance test (OGTT) was conducted in Wistar rats. Additionally, Caco-2 cells were used to determine the effect of quercetin-3- O-glucoside (30 to 60 μM) on mRNA expression of genes involved in glucose uptake by RT-PCR. Thereby, in vivo studies demonstrated that quercetin-3- O-glucoside decreased blood glucose levels evaluated by OGTT in rats. Furthermore, in the presence of Na+, quercetin-3- O-glucoside inhibited methylglucoside (MG) uptake in enterocytes and both sodium dependent glucose transporter-1 (SGLT1)- and glucose transporter-2 (GLUT2)-mediated glucose uptake were downregulated in Caco-2 cells incubated with quercetin-3- O-glucoside. In summary, our results show that quercetin-3- O-glucoside improves postprandial glycemic control in rats and reduces sugar uptake in Caco-2 cells, possible by decreasing the expression of glucose transporters (SGLT1 and GLUT2) according to the results obtained through RT-PCR.
UFLC-MS-IT-TOF and Bioassay Guided Isolation of Flavonoids as Xanthine Oxidase Inhibitors from Diospyros dumetorum
Authors: Deng Zhen-Tao , Yang Tong-Hua , Huang Xiao-Yan , Chen Xing-Long , Zhang Jian-Gang , Zhang Xue-Mei , Chen Ji-Jun , Geng Chang-An
Published: March 2019

Diospyros dumetorum is an important folk medicine for treating pulmonary abscess and inflammation. The leaves of D. dumetorum revealed xanthine oxidase (XOD) inhibitory activity. With the guidance of UFLC-MS-IT-TOF analyses combined with bioassay in vitro, 15 flavonoids were isolated from the active parts of D. dumetorum. Except for 11 (IC50 > 200μM), all compounds showed obvious XOD inhibitory activity with IC50 values of 32.5 ± 0.7 ~ 145.0 ± 3.3 μM. The preliminary structure-activity relationships study suggested that glycosylation on C-3 was unfavorable for XOD inhibitory activity; hydroxyl groups on ring B were essential for maintaining activity; the activity was closely related with the position of galloylation. This is the first recognition of the XOD inhibitory activity and active constituents of D. dumetorum, and will provide valuable information for this plant as a new resource for treating hyperuricemia and gout.
Two New Carboxyethylflavanones from the Heartwood of Dalbergia tonkinensis and Their Antimicrobial Activities
Authors: Son Ninh The , Harada Kenichi , Cuong Nguyen Manh , Fukuyama Yoshiyasu
Published: March 2019

Two new carboxyethylflavanone derivatives, (2 S)-8-carboxyethylnarigenin (2) and (2 S)-6,8-dicarboxyethylpinocembrin (3) were isolated from the heartwood of Dalbergia tonkinensis Prain, along with four known compounds 1, and 4-6. The chemical structures of two new compounds 2 and 3 were elucidated based on analyses of the spectroscopic data, including 1D and 2D NMR, HR-ESI-MS, IR, UV, and CD spectroscopies. By carrying out antimicrobial assay, CH3OH and CHCl3 fractions exhibited weak MIC value at 200 μg/mL against filamentous fungus A. niger (439), whereas the known flavanone 1 and the new carboxyethylflavanone 2 had MIC at 100 μg/mL.
A New C-methyl Isoflavone and Other Compounds from the Roots of Amphiblemma monticola(Melastomataceae)
Authors: Ndjateu Fabrice S. T. , Tene Mathieu , Tane Pierre , Choudhary Muhammad I.
Published: March 2019

The phytochemical study of the EtOH extract of the roots of Amphiblemma monticola Jacq.-Fél. led to the isolation of a new C-methyl isoflavone, amphiblemmone A (1), along with ten known compounds, including 3,4’-di- O-methylellagic acid (2), dimethyl 4,4’,5,5’,6,6’- hexahydroxybiphenyl-2,2’-dicarboxylate (3), lupeol (4), ellagic acid (5), β-sitosterol (6), sitosterol 3- O-β-D-glucopyranoside (7), 3-hydroxy-4,5-dimethoxybenzoic acid (8), 3- O-methylellagic acid 4′- O-β-D-xylopyranoside (9), and a mixture of oleanolic acid (10) and ursolic acid (11). The structures were elucidated using spectroscopic analyses (IR, UV, NMR and MS) and comparison with literature data. Compounds 2-11 were isolated for the first time from the genus Amphiblemma. This is the first report of compounds 2-4, 8 and 9 from the Melastomataceae family.
Biotransformation of Daidzein to Diadzein-7-Glucoside and Its Anti-allergic Activity
Authors: Fujitaka Yuya , Shimoda Kei , Araki Minami , Doi Shouta , Ono Tsubasa , Hamada Hatsuyuki , Hamada Hiroki
Published: March 2019

The biotransformation of daidzein and its diacetate was investigated using cultured plant cells of Phytolacca americana as biocatalysts. Daidzein was glucosylated to the corresponding 7- O-β-D-glucoside. On the other hand, daidzein diacetate was hydrolyzed to daidzein, which was further glucosylated to 7- O-β-D-glucoside with much higher yield in comparison with the biotransformation of daidzein. Daidzein 7- O-β-D-glucoside showed higher inhibitory activity for histamine release from rat peritoneal mast cells than daidzein.
Phenolics from the Fruits of Maclura pomifera
Authors: Su Zushang , Wang Ping , Yuan Wei , Grant Greg , Li Shiyou
Published: March 2019

Two new compounds, maclurin A (1) and maclurin B (2), and six known ones, ononin (3), pterofuran (4), osajin (5), pomiferin (6), 3,4-dihydroxybenzoic acid (7), and 2,3,4-trihydroxybenzoic acid (8) were isolated from the fruit of Maclura pomifera. Compounds 3 and 4 were isolated from the genus for the first time. Structure elucidation was achieved by spectroscopic measurements and by comparison with literature data. Compounds 2-4 exhibited activities against the cancer cell lines A549 and Panc-28 with GI50 values from 18.1 to 32.2, and 20.6 to 43.5 μM, respectively. Compounds 2 and 4 also showed cytotoxicity against HCT 116 with GI50 values of 47.2 and 24.4 μM, respectively.
Broad Spectrum Antimicrobial Activity of Licochalcones A and E against MDR (Multidrug Resistant) Strains of Clinical Origin
Authors: Kim Jung-Eun , Yoon Goo , Shim Jung-Hyun , Cho Seung-Sik
Published: March 2019

The aim of this study was to evaluate the antibacterial activity of the licochalcones A (1) and E (2) against drug resistant strains of clinical origin. The results indicate that the licochalcones had a broad inhibitory activity against tested bacteria. Compared to vancomycin and teicoplanin, these compounds provided weaker activity against non-MDR Staphylococcus aureus and Enterococcus but broader activity against MRSA and VRE strains. The results provide promising baseline information for the potential use of 1 and 2 from Glycyrrhiza inflata in the treatment of drug resistant bacterial infections.
Two Dibenzoquinones from the Fungus Acremonium cavaraeanum
Authors: Xu Qiao , Zhang Miao-Miao , Yana Shu-Zhen , Cao Lu-Fen , Lia Qiang , Lin Jie , Chen Shuang-Lin
Published: March 2019

Two symmetrical dibenzoquinone derivatives were isolated from solid cultures of the fungus Acremonium cavaraeanum. Compound 1 was new and identified as 2,7-dihydroxy-3,6,9-trimethyl-9 H-xanthene-1,4,5,8-tetraone. Compound 2 was 3,3’,6,6’-tetrahydroxy-4,4’-dimethyl-1,1’-bi- p-benzoquinone, i.e. oosporein, which was reported from A. cavaraeanum for the first time. The structure of the dibenzoquinone (1) was unambiguously elucidated using a combination of MS, IR, 1D- and 2D-NMR, and the dibenzoquinone (2) was further determined by single-crystal X-ray diffraction.
Phenolic Derivatives from Periplaneta americana
Authors: Yan Yong-Ming , Zhu Hong-Jie , Xiang Bin , Qi Jing-Jing , Cheng Yong-Xian
Published: March 2019

Periplaneta americana is a medicinal insect used for the treatment of the wound healing in China. In this study, four new compounds, named periplanols A-D (1-4), together with twelve known compounds, were isolated from the whole bodies of this species. Their structures were elucidated by extensive spectroscopic methods. All the isolates except compounds 6, 9, 11, and 14 were tested for their wound healing related activities towards nitric oxide (NO) inhibitory effect, cell proliferation in HDFs, cell migration and angiogenesis in HUVEC, respectively.
A Phenylpropanoid and Biflavonoids from the Needles of Cephalotaxus harringtonia var. harringtonia
Authors: Mendiratta (Nee Chugh) Anju , Dayal Rameshwar , Bartley John P. , Smith Graham
Published: March 2019

A phenylpropanoid [2-(3-methoxy-4-hydroxyphenyl)-propane-1,3-diol] (1) together with four known biflavonoids namely 7, 4′, 7′″, 4′″-tetra- O-methyl amentoflavone (2); 7, 4′, 7″-tri- O-methyl amentoflavone (3); ginkgetin (4); sequoiaflavone (5) were isolated from the acetone soluble extract of needles of Cephalotaxus harringtonia var. harringtonia. Their structures were elucidated mainly on the basis of interpretation of 1D and 2D NMR spectroscopy and X-ray diffraction studies. The detailed spectral data of phenylpropanoid have been described for the first time. Ginkgetin (4) exhibited significant hepatoprotective activity in rat at 6 mg/kg oral dose level.
Resveratrol Demonstrated Higher Antiproliferative and Antiangiogenic Efficacy Compared with Oxyresveratrol on Head and Neck Squamous Cell Carcinoma Cell Lines
Authors: Sintuyanon Napaporn , Phoolcharoen Waranyoo , Pavasant Prasit , Sooampon Sireerat
Published: March 2019

Resveratrol and its derivative, oxyresveratrol, have various pharmacological effects. Several studies demonstrated the anticancer activity of resveratrol. However, little is known about the anticancer activity of oxyresveratrol. In this study, we compared the antiproliferative and antiangiogenic effects of oxyresveratrol and resveratrol. Three head and neck squamous cell carcinoma cell lines (HSC-3, HN-8, and HN-30) were treated with a range of concentrations of either resveratrol or oxyresveratrol. MTT assays demonstrated that resveratrol and oxyresveratrol significantly inhibited cell survival in a dose-dependent manner. Although ELISA and Real-time PCR revealed that oxyresveratrol inhibited vascular endothelial growth factor (VEGF) expression at both the mRNA and protein level, the reduction was lower than that of resveratrol. Altogether, these findings indicate that oxyresveratrol possesses anticancer properties by inhibiting cancer cell proliferation and VEGF expression. However, its efficacy is lower compared with that of resveratrol.
A Comprehensive LC-MS and Isolation Study of Cicada Slough as a Crude Drug
Authors: Matsumoto Hiroki , Konno Katsuhiro , Kazuma Kohei
Published: March 2019

Cicada slough is one of the traditional crude drugs in East Asia. A comprehensive LC-MS analysis was conducted to overview constituents in a commercially purchased cicada slough as a crude drug. It revealed that there were oligomers of N-acetyldopamine with the degree of polymerization of up to 8. High-resolution tandem mass spectrometry could enable a detailed analysis on their structures by uncovering the presumed fragmentation pathways. Additional isolation experiments disclosed the presence of four known compounds: 2,3’,4’-trihydroxyacetophenone, 2-oxo- N-acetyldopamine, protocatechuic acid, and paeonol. The quantified paeonol content for purchased cicada slough ranged from 3 to 290 μg/g dw crude drug, although wild cicada slough did not show the presence of paeonol.