Imperatorin

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Imperatorin
Imperatorin Structural Formula V.1.svg
Names
Preferred IUPAC name
9-[(3-Methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one
Other names
Ammidin
Marmelosin
Pentosalen
8-Isoamylenoxypsoralen
8-Isopentenyloxypsoralene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.893 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3 Yes check.svgY
    Key: OLOOJGVNMBJLLR-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3
    Key: OLOOJGVNMBJLLR-UHFFFAOYAQ
  • O=C/3Oc2c(OC\C=C(/C)C)c1occc1cc2\C=C\3
Properties
C16H14O4
Molar mass 270.28 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Imperatorin is a furocoumarin and a phytochemical that has been isolated from Urena lobata L. (Malvaceae), Angelica archangelica , [1] Angelica dahurica , [2] Glehnia littoralis , [3] Saposhnikovia divaricata , [4] Cnidium monnieri , [5] Incarvillea younghusbandii , [6] and Zanthoxylum americanum mill . [7] It is biosynthesized from umbelliferone, a coumarin derivative. [8]

Contents

Isolation

The procedure for the isolation of imperatorin from Urena lobata involves exhaustively extracting under reflux with benzene the air-dried and pulverised roots followed by separation by column chromatography. [9]

Biochemical activity

Imperatorin was identified from a Bioactive Molecules library in a high throughput screening experiment for inhibitors of the phosphodiesterase PDE4. It displays a significant preference for PDE4B over PDE4A. [10]

See also

Related Research Articles

<i>Angelica archangelica</i> Species of plant

Angelica archangelica, commonly known as garden angelica, wild celery, and Norwegian angelica, is a biennial plant from the family Apiaceae, a subspecies of which is cultivated for its sweetly scented edible stems and roots. Like several other species in Apiaceae, its appearance is similar to several poisonous species, and should not be consumed unless it has been identified with absolute certainty. Synonyms include Archangelica officinalis Hoffm. and Angelica officinalis Moench.

<i>Eleutherococcus senticosus</i> Species of flowering plant

Eleutherococcus senticosus is a species of small, woody shrub in the family Araliaceae native to Northeastern Asia. It may be colloquially called devil's bush, Siberian ginseng, eleuthero, ciwujia, Devil's shrub, shigoka, touch-me-not, wild pepper, or kan jang. E. senticosus has a history of use in folklore and traditional Chinese medicine. Root extracts of E. senticosus are sold as a dietary supplement or cosmetic, usually under the name Siberian ginseng.

<i>Angelica sinensis</i> Species of flowering plant

Angelica sinensis, commonly known as dong quai or female ginseng, is a herb belonging to the family Apiaceae, indigenous to China. Angelica sinensis grows in cool high altitude mountains in East Asia. The yellowish brown root of the plant is harvested in the fall and is a well-known Chinese medicine which has been used for thousands of years.

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

Daidzein is a naturally occurring compound found exclusively in soybeans and other legumes and structurally belongs to a class of compounds known as isoflavones. Daidzein and other isoflavones are produced in plants through the phenylpropanoid pathway of secondary metabolism and are used as signal carriers, and defense responses to pathogenic attacks. In humans, recent research has shown the viability of using daidzein in medicine for menopausal relief, osteoporosis, blood cholesterol, and lowering the risk of some hormone-related cancers, and heart disease. Despite the known health benefits, the use of both puerarin and daidzein is limited by their poor bioavailability and low water solubility.

<span class="mw-page-title-main">Phosphodiesterase 2</span>

The PDE2 enzyme is one of 21 different phosphodiesterases (PDE) found in mammals. These different PDEs can be subdivided to 11 families. The different PDEs of the same family are functionally related despite the fact that their amino acid sequences show considerable divergence. The PDEs have different substrate specificities. Some are cAMP selective hydrolases, others are cGMP selective hydrolases and the rest can hydrolyse both cAMP and cGMP.

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

Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is a chemical compound, of the anthraquinone family, that can be isolated from rhubarb, buckthorn, and Japanese knotweed. Emodin is particularly abundant in the roots of the Chinese rhubarb, knotweed and knotgrass as well as Hawaii ‘au‘auko‘i cassia seeds or coffee weed. It is specifically isolated from Rheum palmatum L. It is also produced by many species of fungi, including members of the genera Aspergillus, Pyrenochaeta, and Pestalotiopsis, inter alia. The common name is derived from Rheum emodi, a taxonomic synonym of Rheum australe, and synonyms include emodol, frangula emodin, rheum emodin, 3-methyl-1,6,8-trihydroxyanthraquinone, Schüttgelb (Schuttgelb), and Persian Berry Lake.

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

Glaucine is an aporphine alkaloid found in several different plant species in the family Papaveraceae such as Glaucium flavum, Glaucium oxylobum and Corydalis yanhusuo, and in other plants like Croton lechleri in the family Euphorbiaceae.

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

Osthol, or osthole, is a chemical compound which is a derivative of coumarin. It is found in a variety of plants including Cnidium monnieri, Angelica archangelica and Angelica pubescens.

<i>Zanthoxylum americanum</i> Species of tree

Zanthoxylum americanum, the common prickly-ash, common pricklyash, common prickly ash or northern prickly-ash, is an aromatic shrub or small tree native to central and eastern portions of the United States and Canada. It is the northernmost New World species in the citrus family, Rutaceae, and is the type species in its genus, which includes sichuan pepper. It can grow to 10 meters (33 ft) tall with a diameter at breast height (DBH) of 15 cm (5.9 in). It produces membranous leaflets and axillary flower clusters. The wood is not commercially valuable, but oil extracts from the bark have been used in traditional and alternative medicine, and have been studied for antifungal and cytotoxic properties. The genus name is sometimes spelled Xanthoxylum.

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

Daidzin is a natural organic compound in the class of phytochemicals known as isoflavones. Daidzin can be found in Japanese plant kudzu and from soybean leaves.

<span class="mw-page-title-main">Huang Bai</span> Herb in Chinese medicine

Huáng bǎi, huáng bó or huáng bò is one of the fifty fundamental herbs of traditional Chinese medicine. Known also as Cortex Phellodendri, it is the bark of one of two species of Phellodendron tree: Phellodendron amurense or Phellodendron chinense.

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

Scopoletin is a coumarin. It found in the root of plants in the genus Scopolia such as Scopolia carniolica and Scopolia japonica, in chicory, in Artemisia scoparia, in the roots and leaves of stinging nettle, in the passion flower, in Brunfelsia, in Viburnum prunifolium, in Solanum nigrum, in Datura metel, in Mallotus resinosus, or and in Kleinhovia hospita. It can also be found in fenugreek, vinegar, some whiskies or in dandelion coffee. A similar coumarin is scoparone. Scopoletin is highly fluorescent when dissolved in DMSO or water and is regularly used as a fluorimetric assay for the detection of hydrogen peroxide in conjunction with horseradish peroxidase. When oxidized, its fluorescence is strongly suppressed.

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

Phenolic acids or phenolcarboxylic acids are types of aromatic acid compounds. Included in that class are substances containing a phenolic ring and an organic carboxylic acid function. Two important naturally occurring types of phenolic acids are hydroxybenzoic acids and hydroxycinnamic acids, which are derived from non-phenolic molecules of benzoic and cinnamic acid, respectively.

<i>Zanthoxylum asiaticum</i> Species of plant

Zanthoxylum asiaticum is a species of plant in the family Rutaceae. Under its synonym Toddalia asiatica, it was the only species in the monotypic genus Toddalia, now included in Zanthoxylum. It is known by the English name orange climber.

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

Angelicin is the parent compound in a family of naturally occurring organic compounds known as the angular furanocoumarins. Structurally, it can be considered as benzapyra-2-one fused with a furan moiety in the 7,8-position. Angelicin is commonly found in certain Apiaceae and Fabaceae plant species such as Bituminaria bituminosa. It has a skin permeability coefficient (LogKp) of -2.46. The maximum absorption is observed at 300 nm. The 1HNMR spectrum is available; the infrared and mass spectra of angelicin can be found in this database. The sublimation of angelicin occurs at 120 °C and the pressure of 0.13 Pa. Angelicin is a coumarine.

Cnidium monnieri (L.) Cusson ex Juss., Monnier's snowparsley, is a flowering plant species in the genus Cnidium. Also known as Shechuangzi, Osthole, Jashoshi, Cnidii Fructus . It may be confused with Bacopa monnieri, Ligusticum officinale, both similar but different plants. The coumarins osthol, imperatorin and xanthotoxol can be found in C. monnieri.

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

Fraxetin is an O-methylated coumarin. It can be found in Fraxinus rhynchophylla and seeds of Datura stramonium. Fraxin is a glucoside of fraxetin.

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

Bacoside A is a mixture of chemical compounds, known as bacosides, isolated from Bacopa monnieri. Its major constituents include the saponins bacoside A3, bacopaside II, jujubogenin isomer of bacopasaponin C, and bacopasaponin C. The mixture has been studied in in vitro experiments and animal models for its potential neuroprotectivity.

Phosphodiesterases (PDEs) are a superfamily of enzymes. This superfamily is further classified into 11 families, PDE1 - PDE11, on the basis of regulatory properties, amino acid sequences, substrate specificities, pharmacological properties and tissue distribution. Their function is to degrade intracellular second messengers such as cyclic adenine monophosphate (cAMP) and cyclic guanosine monophosphate (cGMP) which leads to several biological processes like effect on intracellular calcium level by the Ca2+ pathway.

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

Daturadiol is a pentacyclic triterpenoid found in Datura species including Datura stramonium and Datura innoxia. It is also found in non-Solanaceae plants such as Vernicia fordii and Terminalia brasiliensis.

References

  1. Sigurdsson S, Ogmundsdottir HM, Gudbjarnason S (July–August 2004). "Antiproliferative effect of Angelica archangelica fruits". Zeitschrift für Naturforschung C. 4th. 59 (7–8): 523–7. doi: 10.1515/znc-2004-7-813 . PMID   15813373. S2CID   20991241.
  2. Xie Y, Zhao W, Zhou T, Fan G, Wu Y (September–October 2010). "An efficient strategy based on MAE, HPLC-DAD-ESI-MS/MS and 2D-prep-HPLC-DAD for the rapid extraction, separation, identification and purification of five active coumarin components from Radix Angelicae Dahuricae". Phytochemical Analysis. 21 (5): 473–82. doi:10.1002/pca.1222. PMID   20931624.
  3. Liu M, Shi X, Yang W, Liu S, Wang N, Shi R, Qiao S, Wang Q, Wang Y (July 2011). "Quantitative analysis of nine coumarins in rat urine and bile after oral administration of Radix Glehniae extract by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry". Biomed. Chromatogr. 25 (7): 783–93. doi:10.1002/bmc.1517. PMID   20878664.
  4. Zhao B, Yang X, Yang X, Zhang L (June 2010). "Chemical constituents of roots of Saposhnikovia divaricata" [Chemical constituents of roots of Saposhnikovia divaricata]. Zhongguo Zhong Yao Za Zhi. 2nd (in Chinese). 35 (12): 1569–72. doi:10.4268/cjcmm20101214. PMID   20815209.
  5. Shin, Eunjin; Lee, Chul; Sung, Sang Hyun; Kim, Young Choong; Hwang, Bang Yeon; Lee, Mi Kyeong. (2010-11-17). "Antifibrotic activity of coumarins from Cnidium monnieri fruits in HSC-T6 hepatic stellate cells". Journal of Natural Medicines. 65 (2): 370–374. doi:10.1007/s11418-010-0485-7. PMID   21082271. S2CID   21188255.
  6. Fu, Y; Bai Y; Dawa Z; Bai B; Ding L. (January 2010). "Chemical constituents of Incarvillea younghusbandii" [Chemical constituents of Incarvillea younghusbandii]. Zhongguo Zhong Yao Za Zhi. 2nd. 35 (1): 58–62. doi:10.4268/cjcmm20100112. PMID   20349717.
  7. Bafi-Yeboa, N. F.; Arnason JT; Baker J; Smith ML. (May 2005). "Antifungal constituents of northern prickly ash, Zanthoxylum americanum mill". Phytomedicine. 12 (5): 370–7. doi:10.1016/j.phymed.2003.12.005. PMID   15957372.
  8. F. M. Dean Naturally Occurring Oxygen Ring Compounds, Butterworths, London, 1963.
  9. A furocoumarin, Imperatorin isolated from Urena lobata L. (Malvaceae) Keshab Ghosh Molbank 2004, M382 Archived 2005-04-06 at the Wayback Machine open access publication
  10. Ivey FD, Wang L, Demirbas D, Allain C, Hoffman CS (January 2008). "Development of a fission yeast-based high-throughput screen to identify chemical regulators of cAMP phosphodiesterases". J Biomol Screen. 13 (1): 62–71. doi:10.1177/1087057107312127. PMC   2851203 . PMID   18227226.