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 order to search for minor constituents present in an Ormocarpum kirkii extract, these techniques were applied for the separation and structure elucidation of a series of isoflavanones, biflavanones and biscoumarins. After optimization of chromatographic conditions and subsequent isolation, MS and 1D and 2D NMR data were collected. Experimental and calculated ECD spectra were used in conjunction with NMR data to confirm the absolute configuration of these compounds. Eight compounds were identified for the first time and six have been previously reported. The present approach offers a strategy for accelerating research on natural products.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

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

doi

10.1016/j.phytochem.2012.04.004

subject

Has Abstract

pub_date

2012-07-01 00:00:00

pages

121-8

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(12)00149-5

journal_volume

79

pub_type

杂志文章
  • Enzymatic preparation of 20(S, R)-protopanaxadiol by transformation of 20(S, R)-Rg3 from black ginseng.

    abstract::20(S)-protopanaxadiol (PPD(S)) and 20(R)-protopanaxadiol (PPD(R)), the main metabolites of ginsenosides Rg3(S) and Rg3(R) in black ginseng, are potential candidates for anti-cancer therapy due to their pharmacological activities such as anti-tumor properties. In the present study, we report the preparation of PPD(S, R...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.05.007

    authors: Liu L,Zhu XM,Wang QJ,Zhang DL,Fang ZM,Wang CY,Wang Z,Sun BS,Wu H,Sung CK

    更新日期:2010-09-01 00:00:00

  • Three isoflavones from Derris scandens (Roxb.) Benth and their cancer chemopreventive activity and in vitro antiproliferative effects.

    abstract::Three undescribed isoflavones, derriscandenon A, B, and C, together with seven known isoflavones were isolated and structurally characterized during a study of the chemical constituents in the leaves of Derris scandens (Roxb.) Benth (Leguminosae, Fabaceae) collected in Bangladesh. The inhibitory activity of the compou...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112376

    authors: Ito C,Matsui T,Miyabe K,Hasan CM,Rashid MA,Tokuda H,Itoigawa M

    更新日期:2020-07-01 00:00:00

  • Hypoglycemic activity of withanolides and elicitated Withania somnifera.

    abstract::Withania somnifera, known in India as Asghawhanda, is used traditionally to treat many medical problems including diabetes and has demonstrated therapeutic activity in various animal models as well as in diabetic patients. While much of W. somnifera's therapeutic activity is attributed to withanolides, their role in t...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.02.029

    authors: Gorelick J,Rosenberg R,Smotrich A,Hanuš L,Bernstein N

    更新日期:2015-08-01 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

  • Functional characterization and correlation analysis of phenylalanine ammonia-lyase (PAL) in coumarin biosynthesis from Peucedanum praeruptorum Dunn.

    abstract::Coumarins exhibit many biological activities and are the main specialised metabolites of Peucedanum praeruptorum Dunn, an important plant used in traditional Chinese medicine. In preliminary studies, we cloned several genes involved in coumarin biosynthesis in P. praeruptorum, such as 4-coumarate: CoA ligase (4CL), p-...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.11.006

    authors: Sui Z,Luo J,Yao R,Huang C,Zhao Y,Kong L

    更新日期:2019-02-01 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

  • The biosynthetic origin of oxygen functions in phenylphenalenones of Anigozanthos preissii inferred from NMR- and HRMS-based isotopologue analysis.

    abstract::The biosynthetic origin of 9-phenylphenalenones and the sequence according to which their oxygen functionalities are introduced were studied using nuclear magnetic resonance (NMR) spectroscopy and high-resolution electrospray ionization mass spectrometry (HRESIMS). (13)C-labelled precursors were administered to root c...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.10.007

    authors: Munde T,Maddula RK,Svatos A,Schneider B

    更新日期:2011-01-01 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

  • Polygalasaponins XLII-XLVI from roots of Polygala glomerata.

    abstract::Five new oleanane-type saponins, polygalasaponins XLII-XLVI, along with two known saponins were isolated from the roots of Polygala glomerata Lour. The structures of polygalasaponins XLII-XLVI were elucidated as 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl- (1-->2)-{...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(97)00439-1

    authors: Zhang D,Miyase T,Kuroyanagi M,Umehara K,Noguchi H

    更新日期:1998-02-01 00:00:00

  • Environmental factors influence on chemical polymorphism of the essential oils of Lychnophora ericoides.

    abstract::Lychnophora ericoides is a Brazilian medicinal plant used in folk medicine as an anti-inflammatory and analgesic agent. The essential oils from leaves of two populations with and without scent, collected at 2-month intervals during an 1-year period, were analysed by GC-MS. The results were submitted to principal compo...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.08.002

    authors: Curado MA,Oliveira CB,Jesus JG,Santos SC,Seraphin JC,Ferri PH

    更新日期:2006-11-01 00:00:00

  • A-type proanthocyanidin antioxidant from Dioclea lasiophylla.

    abstract::The A-type proanthocyanidin, epigallocatechin-(2beta-->7,4beta-->8)-epicatechin, together with the known epicatechin, luteolin 3'beta-D-glucopyranoside, chrysoeriol 7beta-D-glucopyranoside and 2-methylpentan-2,4-diol, were isolated from leaves of Dioclea lasiophilla. The structures were established on the basis of the...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00297-1

    authors: Barreiros AL,David JP,de Queiroz LP,David JM

    更新日期:2000-12-01 00:00:00

  • Limonoids from the fruits of Melia toosendan and their NF-κB modulating activities.

    abstract::Eight ring C-seco and ring-intact limonoids, and 25 known limonoids were isolated from the fruits of Melia toosendan (Meliaceae). Their structures were elucidated on the basis of extensive spectroscopic evidence including HRMS, 1D and 2D NMR spectroscopic data. A total of 29 isolated limonoids was evaluated for NF-κB ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.08.009

    authors: Zhu GY,Bai LP,Liu L,Jiang ZH

    更新日期:2014-11-01 00:00:00

  • Ester-type cephalotaxus alkaloids from Cephalotaxus harringtonia var. drupacea.

    abstract::Three alkaloids, neoharringtonine, homoneoharringtonine and 3'S-hydroxyneoharringtonine, were isolated from the leaves and stems of Cephalotaxus harringtonia var. drupacea. Their structures were established by spectroscopic methods, including two-dimensional NMR and CD spectra, and their antileukaemic activity was eva...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(96)00574-2

    authors: Takano I,Yasuda I,Nishijima M,Yanagi Y,Takeya K,Itokawa H

    更新日期:1997-02-01 00:00:00

  • Flavanoids from Caesalpinia pulcherrima.

    abstract::Two new flavanoids, 5,7-dimethoxy-3',4'-methylenedioxyflavanone and isobonducellin along with 2'-hydroxy-2,3,4',6'-tetramethoxychalcone, 5,7-dimethoxyflavone and bonducellin were isolated from the aerial parts of Caesalpinia pulcherrima. The structures of the compounds were settled mainly by interpretation of their 1D...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(03)00325-x

    authors: Srinivas KV,Koteswara Rao Y,Mahender I,Das B,Rama Krishna KV,Hara Kishore K,Murty US

    更新日期:2003-08-01 00:00:00

  • 4-Hydroxy-2-pyrone formation by chalcone and stilbene synthase with nonphysiological substrates.

    abstract::Valerophenone synthase (VPS) is a polyketide synthase that catalyzes the formation of the phloroglucinol derivatives in the synthesis of the bitter acids in hop (Humulus lupulus). The reaction uses isovaleryl-CoA or isobutyryl-CoA, but otherwise it is identical to that of the chalcone synthase in flavonoid biosynthesi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00346-x

    authors: Zuurbier KW,Leser J,Berger T,Hofte AJ,Schröder G,Verpoorte R,Schröder J

    更新日期:1998-12-01 00:00:00

  • A bidesmosidic triterpene saponin from Cephalaria transsylvanica.

    abstract::The structure of cephalaria saponin B, isolated from Cephalaria transsylvanica was elucidated as 3-O-([beta-D-xylopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-->2)-beta-D- xylopyranosyl]-[28-O-beta-D-glucopyranosyl])-3beta,23-dihydroxy-12(13)-oleanene-28-oic acid. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(94)00789-v

    authors: Alankuş-Calişkan O,Anil H

    更新日期:1995-04-01 00:00:00

  • Phenylpropanoid glycosides from Scrophularia ningpoensis.

    abstract::Three phenylpropanoid glycosides named ningposides A (3-O-acetyl-2-O-feruloyl-alpha-L-rhamnopyranose), B (4-O-acetyl-2-O-feruloyl-alpha-L-rhamnopyranose) and C (3-O-acetyl-2-O-p-hydroxycinnamoyl-alpha-L-rhamnopyranose) along with the known compounds sibirioside A, cistanoside D, angoroside C, acteoside, decaffeoylacte...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00171-0

    authors: Li YM,Jiang SH,Gao WY,Zhu DY

    更新日期:2000-08-01 00:00:00

  • Comparative analysis of CYP93E proteins for improved microbial synthesis of plant triterpenoids.

    abstract::Cytochrome P450-dependent monooxygenases (P450s) belonging to the CYP93E subfamily catalyze the C-24 oxidation of the triterpene backbone during the biosynthesis of triterpenoid saponins, which are bioactive plant natural products. In our attempts to produce plant triterpenoids in the yeast Saccharomyces cerevisiae, w...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.10.002

    authors: Moses T,Thevelein JM,Goossens A,Pollier J

    更新日期:2014-12-01 00:00:00

  • Sebestenoids A-D, BACE1 inhibitors from Cordia sebestena.

    abstract::Bioassay-guided fractionation of an extract prepared from the fruits of Cordia sebestena led to the isolation of sebestenoids A-D (1-4). Their structures were elucidated on the basis of extensive NMR experiments and mass spectroscopic measurements. Compounds 1-4 exhibited moderate inhibition of the aspartic protease B...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.09.008

    authors: Dai J,Sorribas A,Yoshida WY,Williams PG

    更新日期:2010-12-01 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

  • Flavonoid gene expression and UV photoprotection in transgenic and mutant Petunia leaves.

    abstract::The effects of UVB radiation on plant growth rate, gene expression and flavonoid content in wild-type, and in transgenic and mutant F3'H deficient Petunia lines have been studied for the first time. In wild-type Petunia, UVB induced an increase in total levels of flavonols and this was due to an up-regulation of sever...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00404-6

    authors: Ryan KG,Swinny EE,Markham KR,Winefield C

    更新日期:2002-01-01 00:00:00

  • Steroidal saponins from the bulbs of Camassia cusickii.

    abstract::Six new steroidal saponins have been isolated from the fresh bulbs of Camassia cusickii. Their structures were determined by spectroscopic analysis and some chemical transformations to be (25R)-5 alpha-spirostan-3 beta,6 alpha-diol (chlorogenin) 6-O-beta-D-glucopyranoside, chlorogenin 6-O-beta-D-glucopyranosyl-(1----2...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(91)80098-l

    authors: Mimaki Y,Sashida Y,Kawashima K

    更新日期:1991-01-01 00:00:00

  • Differing mechanisms of simple nitrile formation on glucosinolate degradation in Lepidium sativum and Nasturtium officinale seeds.

    abstract::Glucosinolates are sulphur-containing glycosides found in brassicaceous plants that can be hydrolysed enzymatically by plant myrosinase or non-enzymatically to form primarily isothiocyanates and/or simple nitriles. From a human health perspective, isothiocyanates are quite important because they are major inducers of ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.07.035

    authors: Williams DJ,Critchley C,Pun S,Chaliha M,O'Hare TJ

    更新日期:2009-07-01 00:00:00

  • Enantioselective accumulation of (--)-pinoresinol through O-demethylation of (+/-)-eudesmin by Aspergillus niger.

    abstract::Microbial transformation of (+/-)-eudesmin by Aspergillus niger was investigated. Enantioselective accumulation of (--)-pinoresinol was shown through O-demethylation of (+/-)-eudesmin. This fungus O- demethylated both enantiomers of eudesmin, but the conversion rates for each enantiomer were clearly different. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(96)00754-6

    authors: Kasahara H,Miyazawa M,Kameoka H

    更新日期:1997-04-01 00:00:00

  • Flavan-3-ols, prodelphinidins and further polyphenols from Cistus salvifolius.

    abstract::Five novel polyphenols have been isolated from the air-dried herb of Cistus salvifolius; they were characterized as epigallocatechin-3-O-(4-hydroxybenzoate), epigallocatechin-(4 beta-->8)-epigallocatechin, epigallocatechin-3-O- gallate-(4 beta-->8)-epigallocatechin, epigallocatechin-(4 beta-->6)-epigallocatechin-3-O-g...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(94)85094-1

    authors: Danne A,Petereit F,Nahrstedt A

    更新日期:1994-09-01 00:00:00

  • Two oleanene glycosides from the aerial parts of Caltha polypetala.

    abstract::Two new oleanene glycosides (1-2) possessing hederagenin as the aglycone were isolated from the methanolic extract of the aerial parts of Caltha polypetala together with four known glycosides. The saccharide portion linked to C-3 of the aglycone is made up of alpha-L-arabinopyranose, alpha-L-rhamnopyranose and galacto...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00164-8

    authors: Baykal T,Bedir E,Calis I,Aquino R,Piacente S,Pizza C

    更新日期:1999-08-01 00:00:00

  • Phytochemical genomics of the Madagascar periwinkle: Unravelling the last twists of the alkaloid engine.

    abstract::The Madagascar periwinkle produces a large palette of Monoterpenoid Indole Alkaloids (MIAs), a class of complex alkaloids including some of the most valuable plant natural products with precious therapeutical values. Evolutionary pressure on one of the hotspots of biodiversity has obviously turned this endemic Malagas...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2014.07.023

    authors: Dugé de Bernonville T,Clastre M,Besseau S,Oudin A,Burlat V,Glévarec G,Lanoue A,Papon N,Giglioli-Guivarc'h N,St-Pierre B,Courdavault V

    更新日期:2015-05-01 00:00:00

  • A 2-oxoglutarate-dependent dioxygenase is integrated in DIMBOA-biosynthesis.

    abstract::Benzoxazinoids are secondary metabolites of grasses that function as natural pesticides. While many steps of DIMBOA biosynthesis have been elucidated, the mechanism of the introduction of OCH(3)-group at the C-7 position was unknown. Inhibitor experiments in Triticum aestivum and Zea mays suggest that a 2-oxoglutarate...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00556-3

    authors: Frey M,Huber K,Park WJ,Sicker D,Lindberg P,Meeley RB,Simmons CR,Yalpani N,Gierl A

    更新日期:2003-02-01 00:00:00

  • Kahiricosides II-V, cycloartane glycosides from an Egyptian collection of Astragalus kahiricus.

    abstract::Four cycloartane-type saponins, kahiricosides II-V (1-4), were isolated from the aerial parts of Astragalus kahiricus of Egyptian origin. Their structures were established as 9beta,19-cyclolanost-24E-ene-3beta,6alpha,16beta,27-tetraol-3-O-beta-D-glucopyranoside, 9beta,19-cyclolanost-24E-ene-3beta,6alpha,16beta,27-tetr...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.08.037

    authors: Radwan MM,El-Sebakhy NA,Asaad AM,Toaima SM,Kingston DG

    更新日期:2004-11-01 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