1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one

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1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one
1,7-bis (4-hydroxyphenyl)-1,4,6-heptatrien-3-one.svg
Names
Preferred IUPAC name
(1E,4E,6E)-1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • (1E,4E,6E):InChI=1S/C19H16O3/c20-17(10-7-16-8-13-19(22)14-9-16)4-2-1-3-15-5-11-18(21)12-6-15/h1-14,21-22H/b3-1+,4-2+,10-7+
    Key: PALMCMYYFAHUGA-BPTNNVFMSA-N
  • (1Z,4E,6E):Key: PALMCMYYFAHUGA-ZRFKDBLFSA-N
  • (Unspecified stereochemistry):Key: PALMCMYYFAHUGA-UHFFFAOYSA-N
  • (1E,4E,6E):c1cc(ccc1C=CC=CC(=O)C=Cc2ccc(cc2)O)O
Properties [2]
C19H16O3
Molar mass 292.334 g·mol−1
AppearanceYellow powder
Melting point 168–170 °C (334–338 °F; 441–443 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Contents

Structure and isolation

The all-trans double bond isomer (1E,4E,6E)-1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one was first fully characterised when isolated from extracts of the rhizomes of turmeric (Curcuma longa) in 1993. [5] It has subsequently been found in other species, including etlingera elatior . [2] A very large number of similar compounds are found in turmeric [6] and ginger. [7] These have been extensively studied in their roles as antioxidants and for their potential pharmacological properties.

The (1Z) double bond isomer is poorly characterised in the literature and it and the compounds with unspecified stereochemistry may in fact be the parent all-E molecule.

Properties

Mohamad et al. (2005) found that the curcuminoids 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one, demethoxycurcumin, and 16-hydroxylabda-8(17),11,13-trien-15,16-olide inhibit lipid peroxidation more potently than does alpha-tocopherol. [4]

See also

Related Research Articles

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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.

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<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.

<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

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<i>Etlingera elatior</i> Herbaceous perennial plant

Etlingera elatior is a species of herbaceous perennial plant in the family Zingiberaceae; it is native to Indonesia, Thailand, Malaysia and New Guinea.

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Kaempferia galanga, commonly known as kencur, aromatic ginger, sand ginger, cutcherry, is a monocotyledonous plant in the ginger family, and one of four plants called galangal. It is found primarily in open areas in Indonesia, southern China, Taiwan, Cambodia, and India, but is also widely cultivated throughout Southeast Asia.

<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 caesia</i> Species of flowering plant

Curcuma caesia, black turmeric or black zedoary, is a perennial herb with bluish-black rhizomes that is native to northeast India.

<i>Etlingera fulgens</i> Species of flowering plant

Etlingera fulgens is a species of herbaceous perennial plant of the family Zingiberaceae. This species occurs in southern Thailand and peninsular Malaysia. E. fulgens is used as an ornamental plant in landscape gardens for its bright red flowers and young leaves.

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

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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.

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References

  1. "Human Metabolome Database: Showing metabocard for (all-E)-1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one (HMDB0040889)". www.hmdb.ca.
  2. 1 2 Habsah, M.; Ali, A.M.; Lajis, N.H.; Sukari, M.A.; Yap, Y.H.; Kikuzaki, H.; Nakatani, N. (2005). "Antitumour-Promoting and Cytotoxic Constituents of Etlingera Elatior". The Malaysian Journal of Medical Sciences. 12 (1): 6–12. PMC   3349407 . PMID   22605941.
  3. Park, S. Y.; Kim, D. S. (2002). "Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: A drug discovery effort against Alzheimer's disease". Journal of Natural Products. 65 (9): 1227–1231. doi:10.1021/np010039x. PMID   12350137.
  4. 1 2 Mohamad, H.; Lajis, N. H.; Abas, F.; Ali, A. M.; Sukari, M. A.; Kikuzaki, H.; Nakatani, N. (2005). "Antioxidative Constituents of Etlingera elatior". Journal of Natural Products. 68 (2): 285–288. doi:10.1021/np040098l. PMID   15730265.
  5. Nakayama, Reiko; Tamura, Yoshiyuki; Yamanaka, Hiroyuki; Kikuzaki, Hiroe; Nakatani, Nobuji (1993). "Two curcuminoid pigments from Curcuma domestica". Phytochemistry. 33 (2): 501–502. doi:10.1016/0031-9422(93)85548-6.
  6. Sun, Wen; Wang, Sheng; Zhao, Wenwen; Wu, Chuanhong; Guo, Shuhui; Gao, Hongwei; Tao, Hongxun; Lu, Jinjian; Wang, Yitao; Chen, Xiuping (2017). "Chemical constituents and biological research on plants in the genus Curcuma". Critical Reviews in Food Science and Nutrition. 57 (7): 1451–1523. doi:10.1080/10408398.2016.1176554. PMID   27229295. S2CID   20902215.
  7. Ma, Xiao-Ni; Xie, Chun-Lan; Miao, Zi; Yang, Quan; Yang, Xian-Wen (2017). "An overview of chemical constituents from Alpinia species in the last six decades". RSC Advances. 7 (23): 14114–14144. Bibcode:2017RSCAd...714114M. doi: 10.1039/C6RA27830B .

Further reading