Quadrangularin A

Last updated
Quadrangularin A
Quadrangularin A.svg
Names
Preferred IUPAC name
(1E,2R,3R)-2-(3,5-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-[(4-hydroxyphenyl)methylidene]indene-4,6-diol
Other names
(±)-Quadrangularin A
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C28H22O6/c29-18-5-1-15(2-6-18)9-23-24-13-22(33)14-25(34)28(24)27(16-3-7-19(30)8-4-16)26(23)17-10-20(31)12-21(32)11-17/h1-14,26-27,29-34H/b23-9-/t26-,27+/m1/s1
    Key: BIQMSWPBPAKGSE-PBSLAQMISA-N
  • C1=CC(=CC=C1C=C2C(C(C3=C(C=C(C=C23)O)O)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O
Properties
C28H22O6
Molar mass 454.478 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Quadrangularin A is an oligostilbene found in Cissus quadrangularis [1] and in Parthenocissus laetevirens . [2] It is a resveratrol dimer.

Related Research Articles

<span class="mw-page-title-main">Mass spectrometry</span> Analytical technique based on determining mass to charge ratio of ions

Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a mass spectrum, a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is used in many different fields and is applied to pure samples as well as complex mixtures.

<span class="mw-page-title-main">Ion source</span> Device that creates charged atoms and molecules (ions)

An ion source is a device that creates atomic and molecular ions. Ion sources are used to form ions for mass spectrometers, optical emission spectrometers, particle accelerators, ion implanters and ion engines.

<span class="mw-page-title-main">Electrospray ionization</span> Technique used in mass spectroscopy

Electrospray ionization (ESI) is a technique used in mass spectrometry to produce ions using an electrospray in which a high voltage is applied to a liquid to create an aerosol. It is especially useful in producing ions from macromolecules because it overcomes the propensity of these molecules to fragment when ionized. ESI is different from other ionization processes since it may produce multiple-charged ions, effectively extending the mass range of the analyser to accommodate the kDa-MDa orders of magnitude observed in proteins and their associated polypeptide fragments.

<span class="mw-page-title-main">Tandem mass spectrometry</span> Type of mass spectrometry

Tandem mass spectrometry, also known as MS/MS or MS2, is a technique in instrumental analysis where two or more stages of analysis using one or more mass analyzer are performed with an additional reaction step in between these analyses to increase their abilities to analyse chemical samples. A common use of tandem MS is the analysis of biomolecules, such as proteins and peptides.

<span class="mw-page-title-main">Matrix-assisted laser desorption/ionization</span> Ionization technique

In mass spectrometry, matrix-assisted laser desorption/ionization (MALDI) is an ionization technique that uses a laser energy-absorbing matrix to create ions from large molecules with minimal fragmentation. It has been applied to the analysis of biomolecules and various organic molecules, which tend to be fragile and fragment when ionized by more conventional ionization methods. It is similar in character to electrospray ionization (ESI) in that both techniques are relatively soft ways of obtaining ions of large molecules in the gas phase, though MALDI typically produces far fewer multi-charged ions.

<span class="mw-page-title-main">Electron-capture dissociation</span>

Electron-capture dissociation (ECD) is a method of fragmenting gas-phase ions for structure elucidation of peptides and proteins in tandem mass spectrometry. It is one of the most widely used techniques for activation and dissociation of mass selected precursor ion in MS/MS. It involves the direct introduction of low-energy electrons to trapped gas-phase ions.

The thomson is a unit that has appeared infrequently in scientific literature relating to the field of mass spectrometry as a unit of mass-to-charge ratio. The unit was proposed by Cooks and Rockwood naming it in honour of J. J. Thomson who measured the mass-to-charge ratio of electrons and ions.

In mass spectrometry, direct analysis in real time (DART) is an ion source that produces electronically or vibronically excited-state species from gases such as helium, argon, or nitrogen that ionize atmospheric molecules or dopant molecules. The ions generated from atmospheric or dopant molecules undergo ion-molecule reactions with the sample molecules to produce analyte ions. Analytes with low ionization energy may be ionized directly. The DART ionization process can produce positive or negative ions depending on the potential applied to the exit electrode.

Surface-enhanced laser desorption/ionization (SELDI) is a soft ionization method in mass spectrometry (MS) used for the analysis of protein mixtures. It is a variation of matrix-assisted laser desorption/ionization (MALDI). In MALDI, the sample is mixed with a matrix material and applied to a metal plate before irradiation by a laser, whereas in SELDI, proteins of interest in a sample become bound to a surface before MS analysis. The sample surface is a key component in the purification, desorption, and ionization of the sample. SELDI is typically used with time-of-flight (TOF) mass spectrometers and is used to detect proteins in tissue samples, blood, urine, or other clinical samples, however, SELDI technology can potentially be used in any application by simply modifying the sample surface.

<span class="mw-page-title-main">Desorption atmospheric pressure photoionization</span>

Desorption atmospheric pressure photoionization (DAPPI) is an ambient ionization technique for mass spectrometry that uses hot solvent vapor for desorption in conjunction with photoionization. Ambient Ionization techniques allow for direct analysis of samples without pretreatment. The direct analysis technique, such as DAPPI, eliminates the extraction steps seen in most nontraditional samples. DAPPI can be used to analyze bulkier samples, such as, tablets, powders, resins, plants, and tissues. The first step of this technique utilizes a jet of hot solvent vapor. The hot jet thermally desorbs the sample from a surface. The vaporized sample is then ionized by the vacuum ultraviolet light and consequently sampled into a mass spectrometer. DAPPI can detect a range of both polar and non-polar compounds, but is most sensitive when analyzing neutral or non-polar compounds. This technique also offers a selective and soft ionization for highly conjugated compounds.

<span class="mw-page-title-main">Ambient ionization</span>

Ambient ionization is a form of ionization in which ions are formed in an ion source outside the mass spectrometer without sample preparation or separation. Ions can be formed by extraction into charged electrospray droplets, thermally desorbed and ionized by chemical ionization, or laser desorbed or ablated and post-ionized before they enter the mass spectrometer.

A hybrid mass spectrometer is a device for tandem mass spectrometry that consists of a combination of two or more m/z separation devices of different types.

<span class="mw-page-title-main">Polymer Factory Sweden AB</span>

Established in 2005, Polymer Factory concentrates on developing well defined dendrimers and dendron based on 2,2-bis(methylol)propionic acid, where the company has the exclusive right to the production, marketing, and sales of such materials. The company also provides tailor-made hyperbranched polymers. Polymer Factory's research lab is located in Stockholm, Sweden.

<span class="mw-page-title-main">Collision-induced dissociation</span> Mass spectrometry technique to induce fragmentation of selected ions in the gas phase

Collision-induced dissociation (CID), also known as collisionally activated dissociation (CAD), is a mass spectrometry technique to induce fragmentation of selected ions in the gas phase. The selected ions are usually accelerated by applying an electrical potential to increase the ion kinetic energy and then allowed to collide with neutral molecules. In the collision, some of the kinetic energy is converted into internal energy which results in bond breakage and the fragmentation of the molecular ion into smaller fragments. These fragment ions can then be analyzed by tandem mass spectrometry.

<span class="mw-page-title-main">Pallidol</span> Chemical compound

Pallidol is a resveratrol dimer. It can be found in red wine, in Cissus pallida or in Parthenocissus laetevirens.

<i>Parthenocissus laetevirens</i> Species of vine

Parthenocissus laetevirens is a climbing plant species in the genus Parthenocissus found in China.

<span class="mw-page-title-main">Oligostilbenoid</span>

Oligostilbenoids are oligomeric forms of stilbenoids. Some molecules are large enough to be considered polyphenols and constitute a class of tannins.

In mass spectrometry, a matrix is a compound that promotes the formation of ions. Matrix compounds are used in matrix-assisted laser desorption/ionization (MALDI), matrix-assisted ionization (MAI), and fast atom bombardment (FAB).

References

  1. Li, Wenling; Li, Hao; Li, Ying; Hou, Zijie (2006). "Total Synthesis of (±)-Quadrangularin A". Angewandte Chemie International Edition. 45 (45): 7609–7611. doi: 10.1002/anie.200603097 . PMID   17051632.
  2. Chen, Juanjuan; He, Shan; Mao, Hui; Sun, Cuirong; Pan, Yuanjiang (2009). "Characterization of polyphenol compounds from the roots and stems of Parthenocissus laetevirensby high-performance liquid chromatography/Tandem mass spectrometry". Rapid Communications in Mass Spectrometry. 23 (6): 737–744. Bibcode:2009RCMS...23..737C. doi:10.1002/rcm.3937. PMID   19204932.