Discovery of a stable vitamin C glycoside in crab apples (Malus sylvestris).

Abstract:

:Non-targeted LC-MS metabolomics on fruit of three wild and domesticated apple species (Malus sylvestris, M. sieversii and M. domestica) showed that two crab apple (M. sylvestris) accessions were distinguished by high concentrations of an ascorbic acid glycoside (AAG). This was partly purified, but key NMR signals were masked by inseparable sucrose. Reference samples of 2-O-β-D-glucopyranosyl L-ascorbic acid and 2-O-β-D-galactopyranosyl L-ascorbic acid were synthesised, but both coincided with the crab apple AAG on LC-MS. Peracetylation of the crab apple extract allowed both purification and characterisation, and the AAG was proven to be 2-O-β-D-glucopyranosyl L-ascorbic acid by comparison of 1H NMR, HRMS and HPLC data with synthesised peracetylated ascorbyl glycoside standards. The stability of the natural AA 2-β-glycoside was similar to synthetic 2-O-α-D-glucopyranosyl L-ascorbic acid, used widely in cosmetic and pharmaceutical products. This discovery in crab apples (Rosaceae) is only the fourth reported occurrence of any ascorbyl glycoside from plants, the others being from Cucurbitaceae, Solanaceae and Brassicaceae. It is hypothesised that AAGs may be more widespread in plants than currently realised.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Richardson AT,Cho J,McGhie TK,Larsen DS,Schaffer RJ,Espley RV,Perry NB

doi

10.1016/j.phytochem.2020.112297

subject

Has Abstract

pub_date

2020-05-01 00:00:00

pages

112297

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(19)31008-8

journal_volume

173

pub_type

杂志文章
  • Oleanane-type triterpenes of Embelia schimperi leaves.

    abstract::An investigation of an ethyl acetate extract of Embelia schimperi leaves has led to the isolation of 10 oleanane-type triterpenes characterized as 3beta,16alpha-di-O-acetyl-13beta, 28-epoxyoleanane (1), 3beta-acetyl-16-oxo-13beta, 28-epoxyoleanane (2), 3beta-acetyl-16alpha-hydroxy-13beta, 28-epoxyoleanane (3), 3beta-a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.07.025

    authors: Manguro LO,Okwiri SO,Lemmen P

    更新日期:2006-12-01 00:00:00

  • alpha-D-Glucuronosyl-(1-->3)-L-galactose, an unusual disaccharide from polysaccharides of the hornwort Anthoceros caucasicus.

    abstract::Acid hydrolysis of cell wall-rich material from thalli of the hornwort Anthoceros caucasicus yielded substantial amounts of an unusual disaccharide (1). Hydrolysis of 1 yielded only GlcA, Gal and unhydrolysed 1. Compound 1 was identified as alpha-D-GlcpA-(1-->3)-L-Gal by 1H and 13C NMR spectroscopic analysis and by th...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(03)00330-3

    authors: Popper ZA,Sadler IH,Fry SC

    更新日期:2003-09-01 00:00:00

  • Macrocyclic trichothecenes are undetectable in kudzu (Pueraria montana) plants treated with a high-producing isolate of Myrothecium verrucaria.

    abstract::Myrothecium verrucaria was found to be an effective pathogen against kudzu grown in the greenhouse and the field. M. verrucaria produced large amounts of macrocyclic trichothecenes when cultured on solid rice medium, including epiroridin E (16.8 mg/g crude extract), epiisororidin E (1 mg/g), roridin E (8.7 mg/g), rori...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00214-x

    authors: Abbas HK,Tak H,Boyette CD,Shier WT,Jarvis BB

    更新日期:2001-09-01 00:00:00

  • Saikosaponin derivatives from Bupleurum wenchuanense.

    abstract::From the roots of Bupleurum wenchuanense 14 derivatives of saikosaponin were isolated and identified as 2"-O-beta-D-xylopyranosylsaikosaponin b2, 3",6"-O O-diacetylsaikosaponin b2, 2"-O-beta-D-glucopyranosylsaikosaponin b2, saikosaponin b2, 6"-O-acetylsaikosaponin b2, saikosaponin d, 2"-O-acetylsaikosaponin d, 3"-O-ac...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(93)85049-w

    authors: Luo SQ,Lin LZ,Cordell GA

    更新日期:1993-07-01 00:00:00

  • Purification and partial sequences of Aralia cordata cinnamyl alcohol dehydrogenase.

    abstract::Cinnamyl alcohol dehydrogenase (CAD) (EC 1.1.1.195) from a dicot, Aralia cordata, was purified to homogeneity and its properties were characterized. The enzyme shows a preference for cinnamyl alcohols and cinnamyl aldehydes as substrates. The M(r) is estimated at 72,000. The enzyme is composed of two heterogeneous sub...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)95137-9

    authors: Hibino T,Shibata D,Umezawa T,Higuchi T

    更新日期:1993-02-01 00:00:00

  • Anti-radical flavonol glycosides from the aerial parts of Cleome chelidonii L.f.

    abstract::Eleven previously undescribed flavonoid glycosides, named cleomesides C-M, along with five known compounds, were isolated from the aerial parts of Cleome chelidonii L.f. (Cleomaceae). All flavonol glycosides were esterified derivatives of 3,7-O-diglycosides of quercetin or kaempferol. Their structures were elucidated ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.06.012

    authors: Nguyen PD,Sayagh C,Borie N,Lavaud C

    更新日期:2017-10-01 00:00:00

  • Cytosolic ascorbate peroxidase 2 (cAPX 2) is involved in the soybean response to flooding.

    abstract::Proteomic analyses of soybean seedlings responding to flooding were conducted to identify key proteins involved. The seeds were germinated on a spongy matrix for two days, and then subjected to flooding for three days. After flooding, the total number of roots, the length of the main root, the lengths of the lateral a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2008.01.007

    authors: Shi F,Yamamoto R,Shimamura S,Hiraga S,Nakayama N,Nakamura T,Yukawa K,Hachinohe M,Matsumoto H,Komatsu S

    更新日期:2008-04-01 00:00:00

  • Hemicellulosic polysaccharides from bamboo shoot cell-walls.

    abstract::Cell-wall polysaccharides of bamboo shoots were extracted with chelating reagent (CDTA, trans-1,2-cyclohexanediamine-N,N,N',N'-tetraacetic acid), Na(2)CO(3) and KOH solutions. Glycosyl composition and glycosyl linkage analyses showed that the hemicellulose was composed of arabinoxylan, (1-->3, 1-->4)-beta-D-glucan, xy...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00237-4

    authors: Edashige Y,Ishii T

    更新日期:1998-11-20 00:00:00

  • The isolation, structure and fragmentation characteristics of natural truxillic and truxinic acid derivatives in Abrus mollis leaves.

    abstract::Five undescribed compounds were separated from Abrus mollis leaves, including two truxillate forms (abrusamide D, H) and three truxinate forms (abrusamide E, F, G). The absolute configuration of abrusamide D was determined by X-ray crystallography. Abrusamide A was reassessed and corrected to be β-truxinate configurat...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112572

    authors: Yuan X,Liu Y,Zhao H,Men L,He C,Qiu Y,Yu Q,Li K,Qi L,Chen D

    更新日期:2021-01-01 00:00:00

  • On the propensity of lignin to associate: a size exclusion chromatography study with lignin derivatives isolated from different plant species.

    abstract::Despite evidence that lignin associates under both aqueous and organic media, the magnitude and nature of the underlying driving forces are still a matter of discussion. The present paper addresses this issue by examining both solution properties and size exclusion behaviour of lignins isolated from five different spe...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.05.026

    authors: Guerra A,Gaspar AR,Contreras S,Lucia LA,Crestini C,Argyropoulos DS

    更新日期:2007-10-01 00:00:00

  • Cell-wall proteins from Sitka spruce xylem are selectively insolubilised during formation of dehydrogenation polymers of coniferyl alcohol.

    abstract::Extracts from the lignifying xylem of Sitka spruce that were enriched in cell-wall-associated glycoproteins contained peroxidase and oxidase activity and readily formed lignin-like water-insoluble dehydrogenation polymers (DHPs) from coniferyl alcohol (CA) when supplied with H2O2. During the formation of DHPs, the abu...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00027-9

    authors: McDougall GJ

    更新日期:2001-05-01 00:00:00

  • The S8 serine, C1A cysteine and A1 aspartic protease families in Arabidopsis.

    abstract::The Arabidopsis thaliana genome has over 550 protease sequences representing all five catalytic types: serine, cysteine, aspartic acid, metallo and threonine (MEROPS peptidase database, http://merops.sanger.ac.uk/), which probably reflect a wide variety of as yet unidentified functions performed by plant proteases. Re...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2003.09.005

    authors: Beers EP,Jones AM,Dickerman AW

    更新日期:2004-01-01 00:00:00

  • (+/-)-Dievodialetins A-G: Seven pairs of enantiomeric coumarin dimers with anti-acetylcholinesterase activity from the roots of Evodia lepta Merr.

    abstract::Seven pairs of undescribed enantiomeric bis-coumarins, (±)-dievodialetins A-G, were separated from the roots of Evodia lepta Merr. Two coumarin nuclei were linked via a 1,4-dimethyl4-vinylcyclohexene moiety in (±)-dievodialetins C-G. The structures of the undescribed compounds, including their absolute configurations ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112597

    authors: Huang GY,Cui H,Lu XY,Zhang LD,Ding XY,Wu JJ,Duan LX,Zhang SJ,Liu Z,Zhang RR

    更新日期:2021-02-01 00:00:00

  • Biotransformation of 20(S)-protopanaxatriol by Mucor spinosus and the cytotoxic structure activity relationships of the transformed products.

    abstract::Biotransformation of 20(S)-protopanaxatriol (1) by the fungus Mucor spinosus AS 3.3450 gave 10 metabolites (2-10), of which 2-5 were previously known. On the basis of NMR and MS analyses, structures 6-10 were established as 12-oxo-23beta-hydroxyl-20(S)-protopanaxatriol (6), 20S,24R-epoxy-dammaran-3beta,6alpha,25-triol...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.05.028

    authors: Zhang J,Guo H,Tian Y,Liu P,Li N,Zhou J,Guo D

    更新日期:2007-10-01 00:00:00

  • Phytochemical analysis and genetic characterization of six Hypericum species from Serbia.

    abstract::The secondary metabolite contents and genetic profiles of six Hypericum species (H. barbatum Jacq., H. hirsutum L., H. linarioides Bosse, H. maculatum Crantz, H. rumeliacum Boiss. and H. tetrapterum Fries), collected from different locations in Serbia, have been analyzed. Methanol extracts of the aerial parts of the p...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.10.021

    authors: Smelcerovic A,Verma V,Spiteller M,Ahmad SM,Puri SC,Qazi GN

    更新日期:2006-01-01 00:00:00

  • Intermediates in the oxidative pathway from torulene to torularhodin in the red yeasts Cystofilobasidium infirmominiatum and C. capitatum (Heterobasidiomycetes, Fungi).

    abstract::Two red Cystofilobasidium spp. isolated from spring sap-flows of Betula pendula were analysed for their carotenoid content. In Cystofilobasidium infirmominiatum, three unusual pigments were detected and identified by structure elucidation as oxidised torulene derivatives. These included 16'-hydroxytorulene and torular...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.05.019

    authors: Herz S,Weber RW,Anke H,Mucci A,Davoli P

    更新日期:2007-10-01 00:00:00

  • An extensive study on the chemical diversity of lipophilic extractives from Eucalyptus globulus wood.

    abstract::Three mature Eucalyptus globulus trees with 40 years of age were studied at three height levels (0%, 35%, and 60% of total tree height) and at three radial regions (sapwood, inner and outer heartwood). The composition of lipophilic extracts was evaluated and an extensive list of 202 compounds was reported for the firs...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112520

    authors: Gominho J,Lourenço A,Marques AV,Pereira H

    更新日期:2020-12-01 00:00:00

  • Phosphorylation-mediated regulation of a rice ABA responsive element binding factor.

    abstract::OREB1 is a rice ABRE binding factor characterized by the presence of multiple highly-conserved phosphorylation domains (C1, C2, C3, and C4) and two kinase recognition motifs, RXXS/T and S/TXXE/D, within different functional domains. An in vitro kinase assay showed that OREB1 is phosphorylated not only by the SnRK2 kin...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.10.005

    authors: Hong JY,Chae MJ,Lee IS,Lee YN,Nam MH,Kim DY,Byun MO,Yoon IS

    更新日期:2011-01-01 00:00:00

  • Dimeric antioxidant and cytotoxic triterpenoid saponins from Terminalia ivorensis A. Chev.

    abstract::Three saponins, including two dimeric triterpenoid glucosides possessing an unusual skeleton, ivorenosides A and B, and a monomeric triterpenoid saponin (ivorenoside C), together with the known sericoside, were isolated from the bark of Terminalia ivorensis. Their structures were established on the basis of 1D and 2D ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.08.020

    authors: Ponou BK,Teponno RB,Ricciutelli M,Quassinti L,Bramucci M,Lupidi G,Barboni L,Tapondjou LA

    更新日期:2010-12-01 00:00:00

  • Non-indolyl cruciferous phytoalexins: Nasturlexins and tridentatols, a striking convergent evolution of defenses in terrestrial plants and marine animals?

    abstract::Highly specialized chemical defense pathways are a particularly noteworthy metabolic characteristic of sessile organisms, whether terrestrial or marine, providing protection against pests and diseases. For this reason, knowledge of the metabolites involved in these processes is crucial to producing ecologically fit cr...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.07.024

    authors: Pedras MS,To QH

    更新日期:2015-05-01 00:00:00

  • Antioxidant phenylpropanoid glycosides from the leaves of Wasabia japonica.

    abstract::From the MeOH extract of the leaves of W. japonica, seven phenylpropanoid gentiobiosides (1-7) were isolated along with eight known phenylpropanoids (8-15). Structures of 1-7 were determined based on spectroscopic data and chemical evidence. The activity of compounds 1-15 to scavenge superoxide anion radicals was inve...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.08.021

    authors: Hosoya T,Yun YS,Kunugi A

    更新日期:2008-02-01 00:00:00

  • Differential tissue distribution of metabolites in Jacobaea vulgaris, Jacobaea aquatica and their crosses.

    abstract::Plants are attacked by many different herbivores. Some will consume whole leaves or roots, while others will attack specific types of tissue. Thus, insight into the metabolite profiles of different types of leaf tissues is necessary to understand plant resistance against herbivores. Jacobaea vulgaris, J. aquatica and ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.03.011

    authors: Nuringtyas TR,Choi YH,Verpoorte R,Klinkhamer PG,Leiss KA

    更新日期:2012-06-01 00:00:00

  • Triterpenoids and their glycosides from the bark of Schefflera octophylla.

    abstract::A new triterpene and its glycosides were isolated from the bark of Schefflera octophylla together with asiatic acid and asiaticoside. Based on spectroscopic data, especially 2DNMR, and chemical transformations the structures of the new compounds were determined as 3 alpha-hydroxy-urs-12-ene-23,28-dioic acid and 3 alph...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(91)83042-j

    authors: Sung TV,Lavaud C,Porzel A,Steglich W,Adam G

    更新日期:1992-01-01 00:00:00

  • Rapid isolation and identification of minor natural products by LC-MS, LC-SPE-NMR and ECD: isoflavanones, biflavanones and bisdihydrocoumarins from Ormocarpum kirkii.

    abstract::The combination of the hyphenated techniques LC-MS and LC-SPE-NMR constitutes a powerful platform for the rapid isolation and identification of minor components from natural sources. Electronic circular dichroism (ECD) is a useful tool to determine the absolute configuration of small quantities of chiral molecules. In...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.04.004

    authors: Xu YJ,Foubert K,Dhooghe L,Lemière F,Maregesi S,Coleman CM,Zou Y,Ferreira D,Apers S,Pieters L

    更新日期:2012-07-01 00:00:00

  • Acylated flavonol glycosides from leaves of Planchonia grandis.

    abstract::Three acylated flavonol glycosides have been identified from leaves of Planchonia grandis Ridley. They possess kaempferol as aglycone and two triglycosidic chains substituting hydroxyl groups at the 3- and 7-positions. The first glycosidic unit of each chain is esterified by a cis or trans p-coumaric acid. Structural ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(03)00215-2

    authors: Crublet ML,Long C,Sévenet T,Hadi HA,Lavaud C

    更新日期:2003-09-01 00:00:00

  • Characterization of native and yeast-expressed tomato fruit fructokinase enzymes.

    abstract::Three fructokinase isozymes (FKI, FKII, FKIII) were separated from both immature and ripe tomato fruit pericarp. All three isozymes were specific for fructose with undetectable activity towards glucose or mannose. The three isozymes could be distinguished from one another with respect to response to fructose, Mg and n...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00331-4

    authors: Petreikov M,Dai N,Granot D,Schaffer AA

    更新日期:2001-11-01 00:00:00

  • Galactinol synthase enzyme activity influences raffinose family oligosaccharides (RFO) accumulation in developing chickpea (Cicer arietinum L.) seeds.

    abstract::To understand raffinose family oligosaccharides (RFO) metabolism in chickpea (Cicer arietinum L.) seeds, RFO accumulation and corresponding biosynthetic enzymes activities were determined during seed development of chickpea genotypes with contrasting RFO concentrations. RFO concentration in mature seeds was found as a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.02.009

    authors: Gangola MP,Jaiswal S,Kannan U,Gaur PM,Båga M,Chibbar RN

    更新日期:2016-05-01 00:00:00

  • Changes in wheat leaf phenolome in response to cold acclimation.

    abstract::A study of wheat (Triticum aestivum L.) leaves phenolome was carried out during cold acclimation of the winter (Claire) and spring (Bounty) varieties using a combination of HPLC-ESI-MS techniques. A total of 40 phenolic and flavonoid compounds were identified, and consisted mainly of two coumarin derivatives, eight si...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.08.021

    authors: Moheb A,Ibrahim RK,Roy R,Sarhan F

    更新日期:2011-12-01 00:00:00

  • Chemical polymorphism of the essential oils from populations of Thymus caespititius grown on the island S. Jorge (Azores).

    abstract::The compositions of the essential oils obtained from ten populations of Thymus caespititius grown on S. Jorge (Azores) were studied by GC and GC-MS. All the oils analysed were dominated by their monoterpene fraction (69-9%). The sesquiterpene fraction was rather small (4-17%) and consisted mainly of oxygen-containing ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00278-8

    authors: Pereira SI,Santos PA,Barroso JG,Figueiredo AC,Pedro LG,Salgueiro LR,Deans SG,Scheffer JJ

    更新日期:2000-10-01 00:00:00

  • Antioxidant dehydrotocopherols as a new chemical character of Stemona species.

    abstract::From the roots of various Stemona species four new dehydrotocopherols (chromenols) were isolated and their structures and stereochemistry elucidated by spectroscopic methods. The double bond between C-3 and C-4 proved to be a typical chemical character of the genus found in most of the species. Various C-methylations ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.08.023

    authors: Brem B,Seger C,Pacher T,Hartl M,Hadacek F,Hofer O,Vajrodaya S,Greger H

    更新日期:2004-10-01 00:00:00