Bisdemethoxycurcumin

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Bisdemethoxycurcumin
Bisdemethoxycurcumin.png
Names
Preferred IUPAC name
(1E,6E)-1,7-Bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
Other names
Curcumin III, bis(4-hydroxycinnamoyl)methane, didemethoxycurcumin, bisdemethoxycurcumin, Bis(p-hydroxycinnamoyl)methane, NSC687839
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
    Key: PREBVFJICNPEKM-YDWXAUTNSA-N
  • C1=CC(=CC=C1C=CC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O
Properties
C19H16O4
Molar mass 308.333 g·mol−1
Density 1.285 g/cm3
Melting point 226 to 231 °C (439 to 448 °F; 499 to 504 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bisdemethoxycurcumin is a curcuminoid found (along with the curcuminoids curcumin and demethoxycurcumin) in turmeric (Curcuma longa), but absent in Javanese turmeric (Curcuma xanthorrhiza). [1] Bisdemethoxycurcumin is used as a pigment and nutraceutical with antimutagenic properties. [2] [3] All three of the curcuminoids found in Curcuma longa have been shown to have antioxidant properties, but bisdemethoxycurcumin is more resistant than the others to alkaline degradation. [4] It was found to be effective in sensitizing PC cells resistance against gemcitabine. [5]

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Related Research Articles

<span class="mw-page-title-main">Turmeric</span> Plant used as spice

Turmeric or Curcuma longa, is a flowering plant in the ginger family Zingiberaceae. It is a perennial, rhizomatous, herbaceous plant native to the Indian subcontinent and Southeast Asia that requires temperatures between 20 and 30 °C and high annual rainfall to thrive. Plants are gathered each year for their rhizomes, some for propagation in the following season and some for consumption.

<span class="mw-page-title-main">Zingiberaceae</span> Family of plants

Zingiberaceae or the ginger family is a family of flowering plants made up of about 50 genera with a total of about 1600 known species of aromatic perennial herbs with creeping horizontal or tuberous rhizomes distributed throughout tropical Africa, Asia, and the Americas. Many of the family's species are important ornamental, spice, or medicinal plants. Ornamental genera include the shell gingers (Alpinia), Siam or summer tulip, Globba, ginger lily (Hedychium), Kaempferia, torch-ginger Etlingera elatior, Renealmia, and ginger (Zingiber). Spices include ginger (Zingiber), galangal or Thai ginger, melegueta pepper, myoga, korarima, turmeric (Curcuma), and cardamom.

<span class="mw-page-title-main">Ginger</span> Species of plant used as a spice

Ginger is a flowering plant whose rhizome, ginger root or ginger, is widely used as a spice and a folk medicine. It is a herbaceous perennial which grows annual pseudostems about one meter tall, bearing narrow leaf blades. The inflorescences bear flowers having pale yellow petals with purple edges, and arise directly from the rhizome on separate shoots.

<span class="mw-page-title-main">Rhizome</span> Underground stem in which various plants asexually reproduce via budding

In botany and dendrology, a rhizome is a modified subterranean plant stem that sends out roots and shoots from its nodes. Rhizomes are also called creeping rootstalks or just rootstalks. Rhizomes develop from axillary buds and grow horizontally. The rhizome also retains the ability to allow new shoots to grow upwards.

<span class="mw-page-title-main">Curcumin</span> Principal curcuminoid of turmeric

Curcumin is a bright yellow chemical produced by plants of the Curcuma longa species. It is the principal curcuminoid of turmeric, a member of the ginger family, Zingiberaceae. It is sold as a herbal supplement, cosmetics ingredient, food flavoring, and food coloring.

<span class="mw-page-title-main">Medicinal plants</span> Plants or derivatives used to treat medical conditions in humans or animals

Medicinal plants, also called medicinal herbs, have been discovered and used in traditional medicine practices since prehistoric times. Plants synthesize hundreds of chemical compounds for various functions, including defense and protection against insects, fungi, diseases, and herbivorous mammals.

<i>Curcuma zedoaria</i> Species of flowering plant

Curcuma zedoaria is a perennial herb and member of the genus Curcuma, family Zingiberaceae. The plant is native to South Asia and Southeast Asia but is now naturalized in other places including the US state of Florida. Zedoary was one of the ancient food plants of the Austronesian peoples. They were spread during prehistoric times to the Pacific Islands and Madagascar during the Austronesian expansion. Its use as a spice in the West today is extremely rare, having been replaced by ginger, and to a lesser extent, yellow turmeric.

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

Gingerol ([6]-gingerol) is a phenolic phytochemical compound found in fresh ginger that activates heat receptors on the tongue. It is normally found as a pungent yellow oil in the ginger rhizome, but can also form a low-melting crystalline solid. This chemical compound is found in all members of the Zingiberaceae family and is high in concentrations in the grains of paradise as well as an African Ginger species.

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

Rosocyanine and rubrocurcumin are two red colored materials, which are formed by the reaction between curcumin and borates.

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

Pinosylvin is an organic compound with the formula C6H5CH=CHC6H3(OH)2. A white solid, it is related to trans-stilbene, but with two hydroxy groups on one of the phenyl substituents. It is very soluble in many organic solvents, such as acetone.

<span class="mw-page-title-main">Ginger wine</span> Fortified wine

Ginger wine is a fortified wine often made from a fermented blend of ginger, raisins, sugar and yeast, that is often fortified by being blended with brandy. It is one of the main ingredients of the Whisky Mac cocktail.

<span class="mw-page-title-main">Curcuminoid</span> Class of chemical compounds

A curcuminoid is a linear diarylheptanoid, a relatively small class of plant secondary metabolites that includes curcumin, demethoxycurcumin, and bisdemethoxycurcumin, all isolated from turmeric. These compounds are natural phenols and produce a pronounced yellow color that is often used to color foods and medicines. Curcumin is obtained from the root of turmeric.

<i>Curcuma zanthorrhiza</i> Species of flowering plant

Curcuma zanthorrhiza, known as temulawak, Java ginger, Javanese ginger, or Javanese turmeric is a plant species, belonging to the ginger family. It is known in Javanese as temulawak, in Sundanese as koneng gede and in Madurese as temu labak. The scientific name is sometimes written as Curcuma xanthorrhiza, but this is an orthographical variant.

Desmethoxycurcumin is a curcuminoid found in turmeric. Commercial grade curcumin contains a mixture of curcuminoids.

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

Menny (Menahem) Rabinovich was a multi-disciplinary Israeli biochemist with expertise in nutrition, health and medicinal plants. Rabinovich was a researcher at Hadassah Medical Center in Jerusalem. He was the founder and director of the Wise Nutrition Center and the developer of the dietary supplement Curcumall. He researched in the fields of molecular biology, science education and integrative medicine focusing on nutrition and health. He served as a member of the scientific committee of the Hebrew Encyclopedia editor and writer of articles in biochemistry, geology, chemistry and medicine.

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

The diarylheptanoids are polyphenols and a relatively small class of plant secondary metabolites. Diarylheptanoids consist of two aromatic rings joined by a seven carbons chain (heptane) and having various substituents. They can be classified into linear (curcuminoids) and cyclic diarylheptanoids. The best known member is curcumin, which is isolated from turmeric and is known as food coloring E100. Some other Curcuma species, such as Curcuma comosa also produce diarylheptanoids.

1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one is a natural product, a curcuminoid antioxidant found in turmeric and torch ginger.

Curcumin synthase categorizes three enzyme isoforms, type III polyketide synthases (PKSs) present in the leaves and rhizome of the turmeric plant that synthesize curcumin. CURS1-3 are responsible for the hydrolysis of feruloyldiketide-CoA, previously produced in the curcuminoid pathway, and a decarboxylative condensation reaction that together comprise one of the final steps in the synthesis pathway for curcumin, demethoxycurcumin, and bisdemethoxycurcumin, the compounds that give turmeric both its distinctive yellow color, and traditional medical benefits. CURS should not be confused with Curcuminoid Synthase (CUS), which catalyzes the one-pot synthesis of bisdemethoxycurcumin in Oryza sativa.

<span class="mw-page-title-main">EF-24</span> Chemical compound

EF-24 is a compound that is a synthetic analogue of curcumin, a bioactive phytochemical from turmeric. Curcumin has antioxidant, antibiotic, anti-inflammatory and anti-cancer properties in vitro but has low potency and very poor bioavailability when taken orally, resulting in limited efficacy. EF-24 was developed to try to improve upon these properties, and has been found to be around 10x more potent than curcumin and with much higher systemic bioavailability. It has never been developed for medical use, though research continues to investigate whether it may be useful as an adjuvant treatment for some cancers alongside conventional chemotherapy drugs.

Tumerones are a group of related chemical compounds of the sesquiterpene class. They are found in turmeric, from which they derive their name, as well as other related plants such as Curcuma caesia. There are multiple structural types of turmerones which differ in the number and placement of double bonds including α-tumerone, β-turmerone, and ar-turmerone. Each of these types consists of multiple stereoisomers.

References

  1. T. K. Lim (11 February 2016). Edible Medicinal and Non-Medicinal Plants: Volume 12 Modified Stems, Roots, Bulbs. Springer. p. 374. ISBN   978-3-319-26065-5.
  2. Hajime Ohigashi; Toshihiko Osawa; Junji Terao; Shaw Watanabe; Toshikazu Yoshikawa (27 November 2013). Food Factors for Cancer Prevention. Springer Science & Business Media. p. 251. ISBN   978-4-431-67017-9.
  3. Jun-Ping Xu (25 November 2016). Cancer Inhibitors from Chinese Natural Medicines. CRC Press. p. 338. ISBN   978-1-4987-8766-6.
  4. Francisco Delgado-Vargas; Octavio Paredes-Lopez (26 December 2002). Natural Colorants for Food and Nutraceutical Uses. CRC Press. p. 244. ISBN   978-1-4200-3171-3.
  5. "Bisdemethoxycurcumin". ScienceDirect. ScienceDirect. Retrieved 5 October 2022.