Neolignan glycosides from Symplocos caudata.

Abstract:

:A phytochemical investigation of the roots of Symplocos caudata Wall (Symplocaceae) resulted in isolation and characterization of four optical isomers of a neolignan glycoside (1-4), a lignan lactone glycoside (5), a phenylpropanoid glycoside (6), as well as two known compounds (7, 8). Their structures were elucidated as (7S,8S)-threo-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-d-glucopyranoside (1), (7R,8R)-threo-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-d-glucopyranoside (2), (7R,8S)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-d-glucopyranoside (3), (7S,8R)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-d-glucopyranoside (4), 8R,8'R-matairesinol-4-O-beta-d-xylopyranosyl-(1-->2)-O-beta-d-glucopyranoside (5), 1-O-[beta-d-xylopyranosyl-(1-->6)-O-beta-d-glucopyranosyl]-2,6-dimethoxy-4-propenyl-phenol (6), matairesinoside (7), and (R)-1-O-(beta-d-glucopyranosyl)-2-[2-methoxy-4-(omega-hydroxypropyl)-phenoxyl]-propan-3-ol (8) on the basis of spectroscopic data (1D and 2D NMR, MS and CD) and chemical evidence.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Huo C,Liang H,Zhao Y,Wang B,Zhang Q

doi

10.1016/j.phytochem.2007.08.022

subject

Has Abstract

pub_date

2008-02-01 00:00:00

pages

788-95

issue

3

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(07)00529-8

journal_volume

69

pub_type

杂志文章
  • Saponins from Astragalus hareftae (NAB.) SIRJ.

    abstract::Four cycloartane- (hareftosides A-D) and oleanane-type triterpenoids (hareftoside E) were isolated from Astragalus hareftae along with fifteen known compounds. Structures of the compounds were established as 3,6-di-O-β-D-xylopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane, 3,6,24-tri-O-β-D-xylopyranosyl-3β,6α,16β...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.07.015

    authors: Horo I,Bedir E,Masullo M,Piacente S,Ozgökçe F,Alankuş-Çalışkan O

    更新日期:2012-12-01 00:00:00

  • Cytochrome P450 enzymes: A driving force of plant diterpene diversity.

    abstract::In plant terpene biosynthesis, oxidation of the hydrocarbon backbone produced by terpene synthases is typically carried out by cytochrome P450 oxygenases (CYPs). The modifications introduced by CYPs include hydroxylations, sequential oxidations at one position and ring rearrangements and closures. These reactions sign...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2018.12.003

    authors: Bathe U,Tissier A

    更新日期:2019-05-01 00:00:00

  • Monoterpenoid accumulation in 1,8-cineole, terpinolene and terpinen-4-ol chemotypes of Melaleuca alternifolia seedlings.

    abstract::Individual leaves of the three most common chemotypes of Melaleuca alternifolia were examined both quantitatively and qualitatively for volatile constituents from the emergence of the first true leaves, through to 6-week-old tenth leaf set material. The 1,8-cineole and terpinolene chemotypes were investigated and comp...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00607-6

    authors: Russell MF,Southwell IA

    更新日期:2003-03-01 00:00:00

  • Structure elucidation and hepatotoxicity evaluation against HepG2 human cells of neo-clerodane diterpenes from Teucrium polium L.

    abstract::Seven neo-clerodanes (teupolins VI-XII) and eleven known compounds were isolated and characterized from leaf extracts of Teucrium polium L., a medicinal plant used in traditional and herbal medicine for its hypolipidemic, hypoglycemic, antioxidant and antiproliferative properties. The structures of these compounds wer...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.07.006

    authors: Fiorentino A,D'Abrosca B,Pacifico S,Scognamiglio M,D'Angelo G,Gallicchio M,Chambery A,Monaco P

    更新日期:2011-11-01 00:00:00

  • Anthocyanin determination in blueberry extracts from various cultivars and their antiproliferative and apoptotic properties in B16-F10 metastatic murine melanoma cells.

    abstract::Blueberry consumption is associated with health benefits contributing to a reduced risk for cardiovascular disease, diabetes and cancer. The aim of this study was to determine the anthocyanin profile of blueberry extracts and to evaluate their effects on B16-F10 metastatic melanoma murine cells. Seven blueberry cultiv...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2013.06.018

    authors: Bunea A,Rugină D,Sconţa Z,Pop RM,Pintea A,Socaciu C,Tăbăran F,Grootaert C,Struijs K,VanCamp J

    更新日期:2013-11-01 00:00:00

  • Phenylpropanoid glucosides from leaves of Coussarea hydrangeifolia (Rubiaceae).

    abstract::Phenylpropanoid glycosides, 1'-O-benzyl-alpha-L-rhamnopyranosyl-(1''-->6')-beta-D-glucopyranoside (1) and alpha-L-xylopyranosyl-(4''-->2')-(3-O-beta-D-glucopyranosyl)-1'-O-E-caffeoyl-beta-D-glucopyranoside (2), together with the known derivatives, 1,6-di-O-caffeoyl-beta-D-glucopyranoside (3), 1-O-(E)-caffeoyl-beta-D-g...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.06.019

    authors: Hamerski L,Bomm MD,Silva DH,Young MC,Furlan M,Eberlin MN,Castro-Gamboa I,Cavalheiro AJ,da Silva Bolzani V

    更新日期:2005-08-01 00:00:00

  • Jatrophane diterpenoids from Euphorbia peplus.

    abstract::From the pro-inflammatory active extract of Euphorbia peplus, a new diterpene polyester (1) based on the jatrophane skeleton was isolated together with the known compounds 2-5. The irritant activities of some jatrophane diterpenes (2, 3 and 6-9) were also investigated: only compound 2 was found to exert a weak pro-inf...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00088-6

    authors: Hohmann J,Vasas A,Günther G,Dombi G,Blazsó G,Falkay G,Máthé I,Jerkovich G

    更新日期:1999-07-01 00:00:00

  • Cytotoxic coumarins from Calophyllum dispar.

    abstract::Six coumarins have been isolated from the fruits and the stem bark of Calophyllum dispar (Clusiaceae). The structures of these minor components were established by means of spectroscopic analysis, including extensive 2D NMR studies. Some of these coumarins exhibited a significant cytotoxic activity against KB cells. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00285-0

    authors: Guilet D,Séraphin D,Rondeau D,Richomme P,Bruneton J

    更新日期:2001-10-01 00:00:00

  • Leaf sheath cuticular waxes on bloomless and sparse-bloom mutants of Sorghum bicolor.

    abstract::Leaf sheath cuticular waxes on wild-type Sorghum bicolor were approximately 96% free fatty acids, with the C28 and C30 acids being 77 and 20% of these acids, respectively. Twelve mutants with markedly reduced wax load were characterized for chemical composition. In all of the 12 mutants, reduction in the amount of C28...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00153-9

    authors: Jenks MA,Rich PJ,Rhodes D,Ashwort EN,Axtell JD,Din CK

    更新日期:2000-07-01 00:00:00

  • Conjugates of auxin and cytokinin.

    abstract::Plant growth and developmental processes as well as environmental responses require the action and cross talk of phytohormones including auxins and cytokinins. Active phytohormones are changed into multiple forms by acylation, esterification or glycosylation, for example. It seems that conjugated compounds could serve...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.05.006

    authors: Bajguz A,Piotrowska A

    更新日期:2009-05-01 00:00:00

  • Secondary products in mycorrhizal roots of tobacco and tomato.

    abstract::Colonization of the roots of various tobacco species and cultivars (Nicotiana glauca Grah., N. longiflora Cav., N. rustica L., N. tabacum L., N. tabacum L. cv. Samsun NN, N. sanderae hort. Sander ex Wats.) as well as tomato plants (Lycopersicon esculentum L. cv. Moneymaker) by the arbuscular mycorrhizal fungus Glomus ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00047-9

    authors: Maier W,Schmidt J,Nimtz M,Wray V,Strack D

    更新日期:2000-06-01 00:00:00

  • Properties of a polynucleotide synthesized by strain 74A of Neurospora crassa.

    abstract::A polynucleotide (or a fragment of RNA) was purified to apparent homogeneity by HPLC from mycelium of the wild strain 74A of the mould Neurospora crassa, after growth on sucrose and in the presence of saturating amounts of inorganic phosphate (Pi) for 72 hr at 30 degrees. The M(r) was ca 20,000 as determined by HPLC a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(95)00531-5

    authors: Carmona EC,Han SW,Palma MS,Rossi A

    更新日期:1996-02-01 00:00:00

  • Aragoside and iridoid glucosides from Aragoa cundinamarcensis.

    abstract::From the water-soluble part of an extract of Aragoa cundinamarcensis were isolated seven iridoid glucosides, namely aucubin, catalpol, rehmannioside D, globularin, gardoside methyl ester, epiloganin and mussaenoside. The main glycoside isolated, however, was a new caffeoyl phenylethanoid triglycoside, named aragoside,...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(03)00157-2

    authors: Rønsted N,Bello MA,Jensen SR

    更新日期:2003-09-01 00:00:00

  • A chlorinated coumarinolignan from the African medicinal plant, Mondia whitei.

    abstract::The unusual chlorinated coumarinolignan, 5-chloropropacin, along with several other known compounds have been isolated from the roots of Mondia whitei. The structure of the chlorinated coumarinolignan was determined by NMR and mass spectroscopic analyses. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.11.012

    authors: Patnam R,Kadali SS,Koumaglo KH,Roy R

    更新日期:2005-03-01 00:00:00

  • Hydrogen and carbon isotopic fractionations of lipid biosynthesis among terrestrial (C3, C4 and CAM) and aquatic plants.

    abstract::Compound-specific hydrogen and carbon isotopic compositions in n-alkanoic acids, phytol and sterols were determined for various plant classes (terrestrial C3-angiosperm; C3-gymnosperm; C4; crassulacean acid metabolism (CAM); and aquatic C3 plants) in order to investigate isotopic fractionations among various plant cla...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.03.036

    authors: Chikaraishi Y,Naraoka H,Poulson SR

    更新日期:2004-05-01 00:00:00

  • Ecdysteroids and bufadienolides from Helleborus torquatus (Ranunculaceae).

    abstract::Three bufadienolides, hellebortin A (5-[beta-D-glucopyranosyloxy]-10,14,16-trihydroxy-19-nor-[5beta,10beta,14beta,16beta]-bufa-3,20,22-trienolide [1]), hellebortin B (5-[beta-D-glucopyranosyloxy]-3,4-epoxy-14-hydroxy-19-oxo-bufa-20,22-dienolide [2]) and hellebortin C (5-[beta-D-glucopyranosyloxy]-3,4-epoxy-10,14-dihyd...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00070-x

    authors: Meng Y,Whiting P,Sik V,Rees HH,Dinan L

    更新日期:2001-06-01 00:00:00

  • Sesquiterpene lactones of Centaurea scoparia.

    abstract::From the ethanolic extract of the aerial parts of Centaurea scoparia four new sesquiterpene lactones, belonging to the guaiane class, were isolated and identified, together with a known germacranolide. The structures were elucidated by spectroscopic methods including one- and two-dimensional NMR studies. The relative ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00257-x

    authors: Youssef DT

    更新日期:1998-11-20 00:00:00

  • Transformations of testosterone and related steroids by Botrytis cinerea.

    abstract::Botrytis cinerea (strain AM235) was used to investigate the transformations of testosterone and related steroids. It was found that the position and stereochemistry of the introduced hydroxyl group, as well as the yield of products, depended on the structure of the substrate. Botrytis cinerea converts the examined sub...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00490-9

    authors: Huszcza E,Dmochowska-Gładysz J

    更新日期:2003-01-01 00:00:00

  • Lignans and neolignans with isovaleroyloxy moiety from Solanum lyratum Thunb.: Chiral resolution, configurational assignment and neuroprotective effects.

    abstract::Eight pairs of enantiomeric lignans and neolignans including thirteen undescribed compounds, along with an undescribed meso compound, were isolated from the herbs of Solanum lyratum Thunb.(Solanaceae). Their structures and relative configurations were determined by extensive spectroscopic analyses of HRESIMS and nucle...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112461

    authors: Li SS,Hou ZL,Yao GD,Guo R,Wang YX,Lin B,Huang XX,Song SJ

    更新日期:2020-10-01 00:00:00

  • Characterisation of triterpenes and new phenolic lipids in Cameroonian propolis.

    abstract::Chemical investigation of a sample of propolis originating from North-Western Cameroon led to the isolation of thirteen alk(en)ylphenols (1-13) (inseparable mixture) along with α-amyrin (14), β-amyrin (15), lupeol (16), cycloartenol (17), mangiferonic acid (18), ambonic acid (19), mangiferolic acid (20), ambolic acid ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.07.016

    authors: Kardar MN,Zhang T,Coxon GD,Watson DG,Fearnley J,Seidel V

    更新日期:2014-10-01 00:00:00

  • Abietane diterpenoids and triterpenoic acids from Salvia cilicica and their antileishmanial activities.

    abstract::Bioguided-fractionation of an acetone extract of the roots of Salvia cilicica (Lamiaceae) led to isolation of two new diterpenes, 7-hydroxy-12-methoxy-20-nor-abieta-1,5(10),7,9,12-pentaen-6,14-dione and abieta-8,12-dien-11,14-dione (12-deoxy-royleanone), together with oleanolic acid, ursolic acid, ferruginol, inuroyol...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00361-8

    authors: Tan N,Kaloga M,Radtke OA,Kiderlen AF,Oksüz S,Ulubelen A,Kolodziej H

    更新日期:2002-12-01 00:00:00

  • Biosynthesis of andrographolide in Andrographis paniculata.

    abstract::Andrographolide, a diterpene lactone, is isolated from Andrographis paniculata which is well known for its medicinal properties. The biosynthetic route to andrographolide was studied using [1-(13)C]acetate, [2-(13)C]acetate and [1,6-(13)C(2)]glucose. The peak enrichment of eight carbon atoms in the (13)C NMR spectra o...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.05.022

    authors: Srivastava N,Akhila A

    更新日期:2010-08-01 00:00:00

  • Response of prostaglandin content in the red alga Gracilaria verrucosa to season and solar irradiance.

    abstract::The influence of solar irradiance and seasons on prostaglandin (PG) and arachidonic acid (AA) content in the marine red alga Gracilaria verrucosa (Huds.) Papenf. (unattached form) was investigated. PGA(2), PGE(2), PGF(2), and 15-keto-PGE(2) were isolated from the alga, quantitatively analyzed as 4-methyl-7-methoxycoum...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00321-1

    authors: Imbs AB,Vologodskaya AV,Nevshupova NV,Khotimchenko SV,Titlyanov EA

    更新日期:2001-12-01 00:00:00

  • Functional characterisation of a tropine-forming reductase gene from Brugmansia arborea, a woody plant species producing tropane alkaloids.

    abstract::Brugmansia arborea is a woody plant species that produces tropane alkaloids (TAs). The gene encoding tropine-forming reductase or tropinone reductase I (BaTRI) in this plant species was functionally characterised. The full-length cDNA of BaTRI encoded a 272-amino-acid polypeptide that was highly similar to tropinone r...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.03.008

    authors: Qiang W,Xia K,Zhang Q,Zeng J,Huang Y,Yang C,Chen M,Liu X,Lan X,Liao Z

    更新日期:2016-07-01 00:00:00

  • Characterization and oxidative in vitro cross-linking of an extensin-like protein and a proline-rich protein purified from chickpea cell walls.

    abstract::Two cell wall proteins from chickpea, known to be rapidly insolubilised by an elicitor-stimulated oxidative burst in-vivo, were purified from suspension cells. N-terminal protein sequencing revealed them as a proline-rich protein and an extensin-like protein. Oxidative cross-linking could be modelled in an in vitro sy...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00463-x

    authors: Otte O,Barz W

    更新日期:2000-01-01 00:00:00

  • The effect of growth temperature on the long-chain alkenes composition in the marine coccolithophorid Emiliania huxleyi.

    abstract::The hydrocarbon fraction of a pure culture of Emiliania huxleyi, composed of a mixture of C31, C33, C37 and C38 polyunsaturated n-alkenes, appeared strongly dependent on the growth temperature of the alga between 8 degrees C and 25 degrees C. The total hydrocarbon content increased linearly with decreasing temperature...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00120-5

    authors: Grossi V,Raphel D,Aubert C,Rontani JF

    更新日期:2000-06-01 00:00:00

  • An 8-hydroxylated external flavone and its 8-O-glucoside from Becium grandiflorum.

    abstract::The major vacuolar flavonoid of a greenhouse-grown plant of Becium grandiflorum has been identified as the 8-O-glucoside of isothymusin (5,8,4'-trihydroxy-6,7-dimethoxyflavone), while the major external flavonoids in the diethyl ether surface wash of the same plant are found to be isothymusin and cirsimaritin (5,4'-di...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(97)00626-2

    authors: Grayer RJ,Veitch NC

    更新日期:1998-03-01 00:00:00

  • An optimized protocol for metabolome analysis in yeast using direct infusion electrospray mass spectrometry.

    abstract::A method for the global analysis of yeast intracellular metabolites, based on electrospray mass spectrometry (ES-MS), has been developed. This has involved the optimization of methods for quenching metabolism in Saccharomyces cerevisiae and extracting the metabolites for analysis by positive-ion electrospray mass spec...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00713-6

    authors: Castrillo JI,Hayes A,Mohammed S,Gaskell SJ,Oliver SG

    更新日期:2003-03-01 00:00:00

  • Ambiguanine A-G, hexahydrobenzophenanthridine alkaloids from Corydalis ambigua var. amurensis.

    abstract::Seven hexahydrobenzophenanthridine-type alkaloids, Ambiguanine A-G, along with eight known alkaloids, were isolated from tubers of Corydalis ambigua var. amurensis. Their structures were elucidated based on extensive spectroscopic analyses, with absolute configurations determined by CD experiments. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.05.013

    authors: Yang ZY,Jiang BH,Teng FK,Han N,Liu ZH,Zhou JJ,Wang Y,Guo DA,Yin J

    更新日期:2014-09-01 00:00:00

  • Anti-inflammatory triterpene saponins of Pithecellobium dulce: characterization of an echinocystic acid bisdesmoside.

    abstract::A new bisdesmodic triterpenoid saponin, dulcin was isolated from the seeds of Pithecellobium dulce and was identified as 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl]- 28-O-[beta-D-xylopyranosyl (1-->6)-beta-D-glucopyranosyl]-echinocystic acid. The known oleanolic acid saponin PE, oleanolic acid 3-O-bet...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)90425-4

    authors: Sahu NP,Mahato SB

    更新日期:1994-11-01 00:00:00