Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum.

Abstract:

:A sulfated fucan containing fraction (SmWE) was isolated from water extract of the brown seaweed Stoechospermum marginatum collected from the Arabian Sea. Anion exchange chromatography of the crude fraction results in the production of a sulfated fucan (F3) having a molecular mass of 40 kDa and specific rotation [alpha]D(30) - 124 degrees (c 0.5, H2O). NMR spectroscopic studies and methylation analysis suggested that the polymer consists of a backbone of (1-->4)- and (1-->3)-linked-alpha-L-fucopyranosyl residues that are substituted at C-2 and C-3, and that fucosyl residues are sulfated mostly at C-2 and/or C-4. SmWE and F3 were selective inhibitors of herpes simplex virus type 1 (strain F, thymidine kinase-deficient strains field and B2006 and syncytial variants arising after selection with a natural carrageenan syn 13-8 and 14-1) and type 2 (strain MS) in Vero cells, with antiviral effective concentration 50% (EC50) values in the range 0.63-10.0 microg/ml. The compounds were highly selective due to the lack of cytotoxicity. The antiviral activity was dependent on the presence of the sulfated fucans during the adsorption period. No direct inactivating effect on virions was observed in a virucidal assay. The absence of anticoagulant activity at concentrations near EC50 confirmed that there was no correlation between the antiviral and anticoagulant properties.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Adhikari U,Mateu CG,Chattopadhyay K,Pujol CA,Damonte EB,Ray B

doi

10.1016/j.phytochem.2006.05.024

subject

Has Abstract

pub_date

2006-11-01 00:00:00

pages

2474-82

issue

22

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(06)00293-7

journal_volume

67

pub_type

杂志文章
  • Induction of acid phosphatase transcripts, protein and enzymatic activity by simulated herbivory of hybrid poplar.

    abstract::Herbivory and wounding upregulate a large suite of defense genes in hybrid poplar leaves. A strongly wound- and herbivore-induced gene with high similarity to Arabidopsis vegetative storage proteins (VSPs) and acid phosphatase (AP) was identified among genes strongly expressed during the poplar herbivore defense respo...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.01.001

    authors: Veljanovski V,Major IT,Patton JJ,Bol E,Louvet S,Hawkins BJ,Constabel CP

    更新日期:2010-04-01 00:00:00

  • Production of (+)-5-deoxystrigol by Lotus japonicus root culture.

    abstract::Lotus japonicus roots, cultured in a modified B5 medium, produced and secreted germination stimulants that induced Striga hermonthica seed germination. The germination-inducing activity was detected both in the roots and the culture filtrate. Following bioassay-guided purification procedures, an active compound was is...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.06.011

    authors: Sugimoto Y,Ueyama T

    更新日期:2008-01-01 00:00:00

  • Steroidal saponins from the leaves of Beaucarnea recurvata.

    abstract::Thirteen steroidal saponins were isolated from the leaves of Beaucarnea recurvata Lem. Their structures were established using one- and two-dimensional NMR spectroscopy and mass spectrometry. Six of them were identified as: 26-O-β-D-glucopyranosyl (25S)-furosta-5,20(22)-diene 1β,3β,26-triol 1-O-α-L-rhamnopyranosyl-(1→...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.03.004

    authors: Eskander J,Lavaud C,Harakat D

    更新日期:2011-06-01 00:00:00

  • Heterogeneity of carrageenans from Chondrus crispus.

    abstract::Carrageenans extracted from gametophytic and sporophytic Chondrus crispus were analysed by hydrolysis, KCl fractionation and 1H NMR spectroscopy. The carrageenan from gametophytic plants is composed predominantly of two KCl insoluble fractions which contain kappa-carrageenan as the major component with 1-carrageenan a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(92)90032-l

    authors: Matsuhiro B,Urzua CC

    更新日期:1992-02-01 00:00:00

  • Phytotoxins from the fungus Malbranchea aurantiaca.

    abstract::Bioassay-directed fractionation of an ethyl acetate extract from cultures of the fungus Malbranchea aurantiaca led to the isolation of two phytotoxic compounds, namely, 1-hydroxy-2-oxoeremophil-1(10),7(11),8(9)-trien-12(8)-olide (1) and penicillic acid (2). The structure of 1 was established by spectroscopic and X-ray...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.03.005

    authors: Martínez-Luis S,González MC,Ulloa M,Mata R

    更新日期:2005-05-01 00:00:00

  • Metabolism and detoxification of phytoalexins and analogs by phytopathogenic fungi.

    abstract::To date, the many examples reporting that fungal pathogens can efficiently detoxify phytoalexins provide strong evidence that the pathogenicity and/or virulence of some fungi is linked to their ability to detoxify their hosts' phytoalexins. The pathways used by plant pathogenic fungi to metabolize and detoxify phytoal...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2004.12.032

    authors: Pedras MS,Ahiahonu PW

    更新日期:2005-02-01 00:00:00

  • A potent bidirectional promoter from the monocot cereal Eleusine coracana.

    abstract::Ragi bifunctional α-amylase-trypsin inhibitor (RBI) of Eleusine coracana (L.) Gaertn. (finger millet) simultaneously inhibits α-amylase and trypsin. In continuation of previous work on the cloning, expression and characterization of RBI, a bidirectional promoter from finger millet was explored on the basis of experime...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.07.009

    authors: Sen S,Dutta SK

    更新日期:2016-09-01 00:00:00

  • Three saponins from Oxytropis species.

    abstract::Three flavonoids and three saponins have been isolated from Oxytropis species. Their structures were determined as isorhamnetin-3-O-beta-D-glucoside, rhamnetin-3-O-beta-D-galactoside, apigenin, 3-O-[alpha-L-rhamnopyranosyl (1----2)-beta-D-glucopyranosyl(1----4)-beta-D-glucuronopyranosyl]+ ++soyasapogenol B, 3-O-[beta-...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(91)85128-m

    authors: Sun RQ,Jia ZJ,Cheng DL

    更新日期:1991-01-01 00:00:00

  • Xanthones from the bark of Garcinia merguensis.

    abstract::The bark of Garcinia merguensis yielded 10 xanthones, merguenone, 1,5-dihydroxy-6'-methyl-6'-(4-methyl-3-pentenyl)-pyrano(2',3':3,2)-xanthone, subelliptenone H, 8-deoxygartanin, rheediaxanthone A, morusignin G, 6-deoxyjacareubin, 1,3,5-trihydroxy-4,8-di(3-methylbut-2-enyl)-xanthone, rheediachromenoxanthone and 6-deoxy...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00433-8

    authors: Nguyen LH,Vo HT,Pham HD,Connolly JD,Harrison LJ

    更新日期:2003-06-01 00:00:00

  • Anti-inflammatory lignans and phenylethanoid glycosides from the root of Isodon ternifolius (D.Don) Kudô.

    abstract::Five undescribed lignans, three undescribed phenylethanoid glycosides and eight known compounds were isolated from the root of Isodon ternifolius (D.Don) Kudô (Lamiaceae). The structures of all of the isolated constituents were characterized by physical data analyses including NMR, MS and ECD. The anti-inflammatory ac...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.05.017

    authors: Zhang Y,Wang K,Chen H,He R,Cai R,Li J,Zhou D,Liu W,Huang X,Yang R,Deng S,Li J,Guan X

    更新日期:2018-09-01 00:00:00

  • Accumulation and tolerance of lead in two contrasting ecotypes of Dianthus carthusianorum.

    abstract::Dianthus carthusianorum is one of the dominant plant species colonising the Zn-Pb waste deposits in Bolesław, Southern Poland. It differs in terms of morphology and genetics from ecotypes inhabiting non-metal-polluted areas. The response of waste-heap (metallicolous, M) and reference (nonmetallicolous, NM) ecotypes of...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.01.008

    authors: Wójcik M,Tukiendorf A

    更新日期:2014-04-01 00:00:00

  • Chemical characterization of high-molar-mass fractions in a Norway spruce knotwood ethanol extract.

    abstract::The low-molar-mass (LMM) fraction, only, i.e., the GC-eluting compounds, which are mainly lignans, has been characterized in Norway spruce knotwood hydrophilic extracts previously. Of this fraction, many lignans and sesquilignans and all GC peaks supposedly representing dilignans remain unidentified. In this work, dil...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.05.006

    authors: Smeds AI,Eklund PC,Willför SM

    更新日期:2016-10-01 00:00:00

  • Antitumor sterols from the mycelia of Cordyceps sinensis.

    abstract::Activity guided fractionations led to the isolation of two antitumor compounds 5 alpha,8 alpha-epidioxy-24(R)-methylcholesta-6,22-dien-3 beta-D-glucopyranoside and 5,6-epoxy-24(R)-methylcholesta-7,22-dien-3 beta-ol from the methanol extract of Cordyceps sinensis. Two previously known compounds, ergosteryl-3-O-beta-D-g...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00128-4

    authors: Bok JW,Lermer L,Chilton J,Klingeman HG,Towers GH

    更新日期:1999-08-01 00:00:00

  • On the formation of lignin polysaccharide networks in Norway spruce.

    abstract::In this study we were mirroring suggested in vivo phenomena of lignin-hemicellulose complex formation in vitro, by cross-linking Norway spruce (Picea abies) galactoglucomannans, xylans and lignin moieties to high molecular weight complexes by laccase treatment. We were able to observe the oxidation and cross-linking o...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.10.027

    authors: Oinonen P,Zhang L,Lawoko M,Henriksson G

    更新日期:2015-03-01 00:00:00

  • Caudatan A, an undescribed human kidney-type glutaminase inhibitor with tetracyclic flavan from Ohwia caudata.

    abstract::Human kidney-type glutaminase (KGA) is an important target that is often over expressed in many cancer cells but very few effective inhibitors of this enzyme have yet reached clinical trials. Caudatan A and caudatan B, two undescribed tetracyclic flavans with an unusual ether bond between the C-4 and C-2' were isolate...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.04.013

    authors: Sun Y,Feng X,Liu X,Qian C,Che X,Cao F,Jin S,Meng D

    更新日期:2018-08-01 00:00:00

  • A hemiterpene glucoside as a probing deterrent of the bean aphid, Megoura crassicauda, from a non-host vetch, Vicia hirsuta.

    abstract::The bean aphid, Megoura crassicauda Mordvilko, feeds selectively on plants belonging to the genus Vicia (Fabaceae). However, it never infests the tiny vetch, V. hirsuta (L.) Gray. The aphid appeared to discriminate between host and non-host plants by tasting specific chemicals during penetration of its stylet into the...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.12.013

    authors: Ohta N,Mori N,Kuwahara Y,Nishida R

    更新日期:2006-03-01 00:00:00

  • Tetraoxygenated xanthones from the fruits of Garcinia cowa.

    abstract::Tetraoxygenated xanthones, cowaxanthones A-E, together with 10 previously reported tetraoxygenated xanthones, were isolated from the crude hexane extract of the fruits of Garcinia cowa. Cowaxanthone B has previously been reported as a synthetic xanthone. Their structures were elucidated by analysis of spectroscopic da...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.02.027

    authors: Panthong K,Pongcharoen W,Phongpaichit S,Taylor WC

    更新日期:2006-05-01 00:00:00

  • A 1H NMR-based metabolomic approach to study the production of antimalarial compounds from Psiadia arguta leaves (pers.) voigt.

    abstract::Psiadia arguta (Asteraceae) is endemic to the island of Mauritius in the Indian Ocean. The species is traditionally used to treat various ailments, such as its use as an expectorant or for the treatment of bronchitis and asthma. Preliminary biological screenings have displayed the antimalarial (Plasmodium falciparum) ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112401

    authors: Mahadeo K,Grondin I,Herbette G,Palama TL,Bouchemal N,Soulange J,Laulloo SJ,Sadeyen J,Humeau L,Frederich M,Gauvin-Bialecki A,Kodja H

    更新日期:2020-08-01 00:00:00

  • Substrate specificity in phospholipid transformations by plant phospholipase D isoenzymes.

    abstract::Phospholipase D (PLD) catalyzes the hydrolysis and transesterification of glycerophospholipids at the terminal phosphodiester bond. In many plants, several isoforms of PLD have been identified without knowing their functional differences. In this paper, the specificities of two PLD isoenzymes from white cabbage (Brass...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.01.011

    authors: Dippe M,Ulbrich-Hofmann R

    更新日期:2009-02-01 00:00:00

  • Biosynthesis of unusual monocyclic alkenes by the diatom Rhizosolenia setigera (Brightwell).

    abstract::Novel, polyunsaturated monocyclic sester- and triterpenes isolated from the diatom Rhizosolenia setigera (Brightwell), are biosynthesised mainly via the mevalonate pathway. The experiments involved incubation of the alga with [1-(13)C]acetate, isolation of the alkenes by extraction and silver ion HPLC, followed by det...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.02.019

    authors: Massé G,Belt ST,Rowland SJ

    更新日期:2004-04-01 00:00:00

  • Curtisians E-H: four p-terphenyl derivatives from the inedible mushroom Paxillus curtisii.

    abstract::Four p-terphenyl derivatives named curtisians E-H (1-4) were isolated from the methanolic extract of fruit bodies of the Basidiomycete Paxillus curtisii by a combination of Sephadex LH-20, silica gel column chromatography and preparative reversed phase HPLC. The relative stereochemistries of the curtisians were elucid...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(03)00263-2

    authors: Quang DN,Hashimoto T,Nukada M,Yamamoto I,Tanaka M,Asakawa Y

    更新日期:2003-09-01 00:00:00

  • Characterization of recombinant nitrile-specifier proteins (NSPs) of Arabidopsis thaliana: dependency on Fe(II) ions and the effect of glucosinolate substrate and reaction conditions.

    abstract::Glucosinolates are plant secondary metabolites that are part of a plant defence system against pathogens and pests, the myrosinase-glucosinolate system, in which glucosinolates get activated by enzymic degradation through thioglucoside glucohydrolases called myrosinases. Epithiospecifier protein (ESP) and nitrile-spec...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.08.004

    authors: Kong XY,Kissen R,Bones AM

    更新日期:2012-12-01 00:00:00

  • Does an apple a day keep the doctor away because a phytoestrogen a day keeps the virus at bay? A review of the anti-viral properties of phytoestrogens.

    abstract::From dengue to herpes and influenza to AIDS, the phytoestrogens that are present in many fruits and vegetables have been shown to exert anti-viral properties. Here we review the various different anti-viral mechanisms employed by phytoestrogens. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2006.11.018

    authors: Martin JH,Crotty S,Warren P,Nelson PN

    更新日期:2007-02-01 00:00:00

  • Cyanogenic glucosides and plant-insect interactions.

    abstract::Cyanogenic glucosides are phytoanticipins known to be present in more than 2500 plant species. They are considered to have an important role in plant defense against herbivores due to bitter taste and release of toxic hydrogen cyanide upon tissue disruption. Some specialized herbivores, especially insects, preferentia...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2003.10.016

    authors: Zagrobelny M,Bak S,Rasmussen AV,Jørgensen B,Naumann CM,Lindberg Møller B

    更新日期:2004-02-01 00:00:00

  • Glucose-conjugation of the flavones of Psiadia arabica by Cunninghamella elegans.

    abstract::Microbial transformation of psiadiarabin and its 6-desmethoxy analogue 5,3' dihydroxy-7,2',4'5'-tetramethoxyflavone by Cunninghamella elegans NRRL 1392 gave the 3'-glucoside conjugates of the two flavones. Structural elucidation of these two new metabolites was achieved using 1D and 2D NMR spectroscopy and CIMS. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:

    authors: Ibrahim AR,Galal AM,Mossa JS,el-Feraly FS

    更新日期:1997-12-01 00:00:00

  • Diels-Alder type adducts from Morus cathayana.

    abstract::Two natural Diels-Alder type adducts, cathayanon A (1) and cathayanon B (2), resembling sanggenon C (4) and O (3), were isolated from the root bark of Morus cathayana. Their structures were elucidated on the basis of spectroscopic evidence. The structure of 1 was confirmed by the results of X-ray crystallographic anal...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00171-6

    authors: Shen RC,Lin M

    更新日期:2001-08-01 00:00:00

  • Chlorantholides A-F, eudesmane-type sesquiterpene lactones from Chloranthus elatior.

    abstract::Six eudesmane-type sesquiterpene lactones, named chlorantholides A-F, were isolated from the ethanol extract of Chloranthus elatior (Chloranthaceae) together with 12 known compounds. Their structures were elucidated on the basis of extensive spectroscopic analysis, and their absolute configurations were studied by the...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.02.008

    authors: Wang F,Zhou DS,Wei GZ,Ren FC,Liu JK

    更新日期:2012-05-01 00:00:00

  • α,β-Unsaturated monoterpene acid glucose esters: structural diversity, bioactivities and functional roles.

    abstract::The glycosylation of lipophilic small molecules produces many important plant secondary metabolites. The majority of these are O-glycosides with relatively fewer occurring as glucose esters of aromatic or aliphatic acids. In particular, monoterpene acid glucose esters have much lower structural diversity and distribut...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2011.08.026

    authors: Goodger JQ,Woodrow IE

    更新日期:2011-12-01 00:00:00

  • Influence of trans-cis isomerisation of coumaric acid substituents on colour variance and stabilisation in anthocyanins.

    abstract::The recently isolated pigments from Petunia integrifolia and Triteleia bridgesii present a distinct feature that sheds new light on the understanding of intramolecular copigmentation of anthocyanins. These are among the infrequent anthocyanins that naturally present a coumaric acid substituent in both cis and trans fo...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00105-4

    authors: George F,Figueiredo P,Toki K,Tatsuzawa F,Saito N,Brouillard R

    更新日期:2001-07-01 00:00:00

  • Synthesis of enantio-manoyl oxides: modifiers of the activity of adenylatecyclase enzyme.

    abstract::Cyclization of methyl ent-8 alpha-hydroxylabd-13(16),14-dien-18-oate with m-chloroperbenzoic acid gave methyl (13S)-ent-16-hydroxy-8 alpha,13-epoxylabd-14-en-18-oate and its epimer at C-13. Biotransformation of the former (which exhibits antileishmania activity) with Rhizopus nigricans cultures produced the methyl (13...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(94)00549-9

    authors: García-Granados A,Liñán E,Martínez A,Onorato ME,Parra A,Arias JM

    更新日期:1995-01-01 00:00:00