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

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).^{[1] [2]}

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.^[3] It has subsequently been found in other species, including etlingera elatior.A very large number of similar compounds are found in turmeric^[4] and ginger.^[5] 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.

See also

• Diarylheptanoid

Further reading

• Book: 10.1016/B978-0-12-811518-3.00010-7 . Turmeric: A Review of Its Chemical Composition, Quality Control, Bioactivity, and Pharmaceutical Application . Natural and Artificial Flavoring Agents and Food Dyes . 2018 . Meng . Fan-Cheng . Zhou . Yan-Qing . Ren . Dai . Wang . Ruibing . Wang . Chunming . Lin . Li-Gen . Zhang . Xiao-Qi . Ye . Wen-Cai . Zhang . Qing-Wen . 299–350 . 9780128115183 .
• Book: 10.1016/B978-0-08-102071-5.00005-2 . Turmeric: Isolation and synthesis of important biological molecules . Synthesis of Medicinal Agents from Plants . 2018 . Agarwal . Shweta . Mishra . Ritu . Gupta . Anil Kumar . Gupta . Atul . 105–125 . 9780081020715 .

Notes and References

1. 10.1021/np010039x . Park . S. Y. . Kim . D. S. . 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 . 2002 . 12350137 .
2. Mohamad . H. . Lajis . N. H. . Abas . F. . Ali . A. M. . Sukari . M. A. . Kikuzaki . H. . Nakatani . N. . 10.1021/np040098l . Antioxidative Constituents of Etlingera elatior. Journal of Natural Products . 68 . 2 . 285–288 . 2005 . 15730265 .
3. 10.1016/0031-9422(93)85548-6 . Two curcuminoid pigments from Curcuma domestica . 1993 . Nakayama . Reiko . Tamura . Yoshiyuki . Yamanaka . Hiroyuki . Kikuzaki . Hiroe . Nakatani . Nobuji . Phytochemistry . 33 . 2 . 501–502 .
4. 10.1080/10408398.2016.1176554 . Chemical constituents and biological research on plants in the genus Curcuma . 2017 . Sun . Wen . Wang . Sheng . Zhao . Wenwen . Wu . Chuanhong . Guo . Shuhui . Gao . Hongwei . Tao . Hongxun . Lu . Jinjian . Wang . Yitao . Chen . Xiuping . Critical Reviews in Food Science and Nutrition . 57 . 7 . 1451–1523 . 27229295 . 20902215 .
5. 10.1039/C6RA27830B . free . An overview of chemical constituents from Alpinia species in the last six decades . 2017 . Ma . Xiao-Ni . Xie . Chun-Lan . Miao . Zi . Yang . Quan . Yang . Xian-Wen . RSC Advances . 7 . 23 . 14114–14144 . 2017RSCAd...714114M .