Skip to content
2000
  1. Home
  2. A-Z Publications
  3. Current Molecular Pharmacology
  4. Volume 17, Issue 1
  5. Article
Volume 17, Issue 1
  • ISSN: 1874-4672
  • E-ISSN: 1874-4702
file format pdf download PDF
side by side viewer icon HTML

Abstract

Alnustone (4(E)-,6(E)-1,7-Diphenyl-hepta-4,6-dien-3-one) is a non-phenolic natural diarylheptanoid, which was first isolated and identified from the male flower of (Betulaceae). It can also be isolated from Curcuma (Zingiberaceae) rhizomes and Hayata (Zingiberaceae) seeds. It was first synthesized through a five-step process from β-phenyl propionyl chloride. In later years, new methods for synthesizing Alnustone were designed and performed with different yields. Due to the various therapeutic effects exhibited by alnustone like other diarylheptanoids, its biological activities such as antioxidant, antibacterial, and anti-inflammatory properties have been the subject of many studies.

This article has reviewed different aspects of this valuable natural compound, including its natural and synthetic sources, therapeutic effects, and pharmacokinetics as a potential future therapeutic agent.

© 2024 The Author(s). Published by Bentham Science Publisher.
This is an open access article distributed under the terms of the Creative Commons Attribution 4.0 International Public License (CC-BY 4.0), a copy of which is available at: https://creativecommons.org/licenses/by/4.0/legalcode. This license permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
Loading

Article metrics loading...

/content/journals/cmp/10.2174/0118761429252459231115060139
2024-01-26
2024-11-22

  • From This Site

    /content/journals/cmp/10.2174/0118761429252459231115060139
    dcterms_title,dcterms_subject,pub_keyword
    -contentType:Contributor -contentType:Concept -contentType:Institution
    10
    5
Loading full text...

Full text loading...

/deliver/fulltext/cmp/17/1/e18761429252459.html?itemId=/content/journals/cmp/10.2174/0118761429252459231115060139&mimeType=html&fmt=ahah

References

  1. ClaesonP. Naturally occurring 1, 7-diarylheptanoids.J. Indian Chem. Soc.199471509521
     [Google Scholar]
  2. Vanucci-BacquéC. Bedos-BelvalF. Anti-inflammatory activity of naturally occuring diarylheptanoids – A review.Bioorg. Med. Chem.20213111597110.1016/j.bmc.2020.11597133422907
     [Google Scholar]
  3. SugaT. AsakawaY. IwataN. 1, 7-diphenyl-1, 3-heptadien-5-on, ein neues keton aus alnus pendula (betulaceae).Chem. Informationsd. Org. Chem.197124010.1002/chin.197140280
     [Google Scholar]
  4. SugaT. IwataN. AsakawaY. Chemical constituents of the male flower of Alnus pendula (Betulaceae).Bull. Chem. Soc. Jpn.19724572058206010.1246/bcsj.45.2058
     [Google Scholar]
  5. PerC. ClaesonU.P. TuchindaP. ReutrakulV. Occurrence, structure and bioactivity of 1,7-diarylheptanoids.Stud. Nat. Prod. Chem.20022688190810.1016/S1572‑5995(02)80021‑7
     [Google Scholar]
  6. AokiT. OhtaS. SugaT. Triterpenoids, diarylheptanoids and their glycosides in the flowers of Alnus species.Phytochemistry199029113611361410.1016/0031‑9422(90)85286‑O
     [Google Scholar]
  7. KuroyanagiM. NoroT. FukushimaS. AiyamaR. IkutaA. ItokawaH. MoritaM. Studies on the constituents of the seeds of Alpinia katsumadai Hayata.Chem. Pharm. Bull.19833151544155010.1248/cpb.31.1544
     [Google Scholar]
  8. ClaesonP. PanthongA. TuchindaP. ReutrakulV. KanjanapothiD. TaylorW. SantisukT. Three non-phenolic diarylheptanoids with anti-inflammatory activity from Curcuma xanthorrhiza. Planta Med.199359545145410.1055/s‑2006‑9597308255938
     [Google Scholar]
  9. ClaesonP. PongprayoonU. SematongT. TuchindaP. ReutrakulV. SoontornsaratuneP. TaylorW. Non-phenolic linear diarylheptanoids from Curcuma xanthorrhiza: a novel type of topical anti-inflammatory agents: Structure-activity relationship.Planta Med.199662323624010.1055/s‑2006‑9578678693036
     [Google Scholar]
  10. SugaT. AokiT. KawadaY. OhtaS. OhtaE. C31,-secodammarane-type triterpenoid saponins from the male flowers of Alnus pendula.Phytochemistry19842361297129910.1016/S0031‑9422(00)80445‑8
     [Google Scholar]
  11. SakakibaraM. MoriK. MatsuiM. Synthesis of 1, 7-diphenyl-1, 3-heptadien-5-one, one of the components in the fresh catkin of Alnus pendula.Agric. Biol. Chem.1972361018251827
     [Google Scholar]
  12. VigO. Synthesis of 1, 7-diphenyl-trans, trans-1, 3-heptadien-5-one (Alnustone).Indian J. Chem.19751311291130
     [Google Scholar]
  13. VigO. BariS. SattarM. SharmaS. MahajanN. New synthesis of alnustone, tagetone and dihydrotagetone from beta-ketophosphonate.J. Indian Chem. Soc.198966298100
     [Google Scholar]
  14. KatoN. HamadaY. ShioiriT. New methods and reagents in organic synthesis. 47. A general, efficient, and convenient synthesis of diarylheptanoids.Chem. Pharm. Bull.19843283323332610.1248/cpb.32.3323
     [Google Scholar]
  15. ItokawaH. AiyamaR. IkutaA. Synthesis of diarylheptanoids and assessment of their pungency.Chem. Pharm. Bull.19833172491249610.1248/cpb.31.2491
     [Google Scholar]
  16. BaranovskyA. SchmittB. FowlerD.J. SchneiderB. Synthesis of new biosynthetically important diarylheptanoids and their oxa-and fluoro-analogues by three different strategies.Synth. Commun.20033361019104510.1081/SCC‑120016367
     [Google Scholar]
  17. WangN. WuZ. WangJ. UllahN. LuY. Recent applications of asymmetric organocatalytic annulation reactions in natural product synthesis.Chem. Soc. Rev.202150179766979310.1039/D0CS01124J34286704
     [Google Scholar]
  18. YangY. KinoshitaK. KoyamaK. TakahashiK. TaiT. NunouraY. WatanabeK. Two novel anti-emetic principles of Alpinia katsumadai.J. Nat. Prod.199962121672167410.1021/np990096e10654416
     [Google Scholar]
  19. WangY. BaoR. HuangS. TangY. Bioinspired total synthesis of katsumadain A by organocatalytic enantioselective 1,4-conjugate addition.Beilstein J. Org. Chem.2013911601160610.3762/bjoc.9.18223946860
     [Google Scholar]
  20. CoreyE.J. BakshiR.K. ShibataS. ChenC.P. SinghV.K. A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses.J. Am. Chem. Soc.1987109257925792610.1021/ja00259a075
     [Google Scholar]
  21. SuksamrarnA. PonglikitmongkolM. WongkrajangK. ChindaduangA. KittidanairakS. JankamA. YingyongnarongkulB. KittipanumatN. ChokchaisiriR. KhetkamP. PiyachaturawatP. Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation.Bioorg. Med. Chem.200816146891690210.1016/j.bmc.2008.05.05118554915
     [Google Scholar]
  22. YangY. KinoshitaK. KoyamaK. TakahashiK. KondoS. WatanabeK. Structure-antiemetic-activity of some diarylheptanoids and their analogues.Phytomedicine20029214615210.1078/0944‑7113‑0009111995948
     [Google Scholar]
  23. MenzekA. KarakayaM.G. KayaA.A. Reductions of benzene derivatives whose benzylic positions bear oxygen atoms under mild conditions.Helv. Chim. Acta200891122299230710.1002/hlca.200890250
     [Google Scholar]
  24. AltundaşA. MenzekA. GültekinD.D. KarakayaM. Excellent and convenient procedures for reduction of benzene and its derivatives.Turk. J. Chem.2005295513518
     [Google Scholar]
  25. LeeS.L. HuangW.J. LinW.W. LeeS.S. ChenC.H. Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs.Bioorg. Med. Chem.200513226175618110.1016/j.bmc.2005.06.05816084726
     [Google Scholar]
  26. TianZ. AnN. ZhouB. XiaoP. KohaneI.S. WuE. Cytotoxic diarylheptanoid induces cell cycle arrest and apoptosis via increasing ATF3 and stabilizing p53 in SH-SY5Y cells.Cancer Chemother. Pharmacol.20096361131113910.1007/s00280‑008‑0832‑518836721
     [Google Scholar]
  27. AraújoC.A.C. LeonL.L. Biological activities of Curcuma longa L.Mem. Inst. Oswaldo Cruz200196572372810.1590/S0074‑0276200100050002611500779
     [Google Scholar]
  28. HiroshiH. YoshinobuK. NobuharuK. YasumasaH. TakayukiS. RitsuoA. HidejiI. FumiyukiK. UshioS. Antihepatotoxic actions of gingerols and diarylheptanoids.J. Ethnopharmacol.1985141313910.1016/0378‑8741(85)90025‑X4087920
     [Google Scholar]
  29. SawamuraR. ShimizuT. SunY. YasukawaK. MiuraM. ToriyamaM. MotohashiS. WatanabeW. KonnoK. KurokawaM. In vitro and in vivo anti-influenza virus activity of diarylheptanoids isolated from Alpinia officinarum.Antivir. Chem. Chemother.2010211334110.3851/IMP167621045258
     [Google Scholar]
  30. AliM.S. BanskotaA.H. TezukaY. SaikiI. KadotaS. Antiproliferative activity of diarylheptanoids from the seeds of Alpinia blepharocalyx.Biol. Pharm. Bull.200124552552810.1248/bpb.24.52511379774
     [Google Scholar]
  31. IshidaJ. KozukaM. TokudaH. NishinoH. NagumoS. LeeK.H. NagaiM. Chemopreventive potential of cyclic diarylheptanoids.Bioorg. Med. Chem.200210103361336510.1016/S0968‑0896(02)00164‑512150883
     [Google Scholar]
  32. UtoT. TungN.H. Appiah-OpongR. AningA. MorinagaO. EdohD. NyarkoA.K. ShoyamaY. Antiproliferative and pro-apoptotic activity of diarylheptanoids isolated from the bark of Alnus japonica in human leukemia cell lines.Am. J. Chin. Med.201543475776710.1142/S0192415X1550047026119959
     [Google Scholar]
  33. HuangW.Z. ZhangC.F. ZhangM. WangZ.T. A new biphenylpropanoid from Alpinia katsumadai. J. Chin. Chem. Soc.20075461553155610.1002/jccs.200700218
     [Google Scholar]
  34. HuangW. DaiX. LiuY. ZhangC. ZhangM. WangZ. Studies on antibacterial activity of flavonoids and diarylheptanoids from Alpinia katsumadai. Zhiwu Ziyuan Yu Huanjing200615137
     [Google Scholar]
  35. GrienkeU. SchmidtkeM. KirchmairJ. PfarrK. WutzlerP. DürrwaldR. WolberG. LiedlK.R. StuppnerH. RollingerJ.M. Antiviral potential and molecular insight into neuraminidase inhibiting diarylheptanoids from Alpinia katsumadai. J. Med. Chem.201053277878610.1021/jm901440f20014777
     [Google Scholar]
  36. BurmaoğluS. ÇelikH. GöksuS. MaraşA. AltundaşR. SeçenH. Synthesis of two alnustone-like natural diarylheptanoids via 4+ 3 strategy.Synth. Commun.20093991549156210.1080/00397910802542036
     [Google Scholar]
  37. KikuzakiH. KawaiY. NakataniN. 1,1-Diphenyl-2-picrylhydrazyl radical-scavenging active compounds from greater cardamom (Amomum subulatum Roxb.).J. Nutr. Sci. Vitaminol. (Tokyo)200147216717110.3177/jnsv.47.16711508709
     [Google Scholar]
  38. JangD.S. ParkE.J. HawthorneM.E. VigoJ.S. GrahamJ.G. CabiesesF. SantarsieroB.D. MesecarA.D. FongH.H.S. MehtaR.G. PezzutoJ.M. KinghornA.D. Constituents of Musa x paradisiaca cultivar with the potential to induce the phase II enzyme, quinone reductase.J. Agric. Food Chem.200250226330633410.1021/jf020667012381112
     [Google Scholar]
  39. MoonS-S. ChoS-C. LeeJ-Y. Tsaokoarylone, a cytotoxic diarylheptanoid from Amomum tsao-ko fruits.Bull. Korean Chem. Soc.200526344745010.5012/bkcs.2005.26.3.447
     [Google Scholar]
  40. LiJ. ZhaoF. LiM.Z. ChenL.X. QiuF. Diarylheptanoids from the rhizomes of Curcuma kwangsiensis.J. Nat. Prod.201073101667167110.1021/np100392m20879743
     [Google Scholar]
  41. KüçükoğluK. Seçi̇nti̇H. ÖzgürA. SeçenH. TutarY. Synthesis, molecular docking, and antitumoral activity of alnustone-like compounds against estrogen receptor alpha-positive human breast cancer.Turk. J. Chem.201539117919310.3906/kim‑1408‑72
     [Google Scholar]
  42. Demi̇rŞ.B. Seçi̇nti̇H. Çelebi̇oğluN. ÖzdalM. SezenA. GülmezÖ. AlgurÖ.F. SeçenH. Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids.Turk. J. Chem.202044358960110.3906/kim‑1911‑6133488179
     [Google Scholar]
  43. SongY. ZhouY. YanX.T. BiJ.B. QiuX. BianY. WangK.F. ZhangY. FengX.S. Pharmacokinetics and tissue distribution of Alnustone in rats after intravenous administration by liquid chromatography-mass spectrometry.Molecules20192417318310.3390/molecules2417318331480657
     [Google Scholar]
  44. ZacharisC.K. MarkopoulouC.K. Recent trends in pharmaceutical analytical chemistry.Molecules20202516356010.3390/molecules2516356032764423
     [Google Scholar]
/content/journals/cmp/10.2174/0118761429252459231115060139
Loading
Alnustone: A Review of its Sources, Pharmacology, and Pharmacokinetics
Curr Mol Pharmacol 17, e18761429252459 (2024); https://doi.org/10.2174/0118761429252459231115060139
/content/journals/cmp/10.2174/0118761429252459231115060139
/content/journals/cmp/10.2174/0118761429252459231115060139
Loading

Data & Media loading...


  • Article Type:     Review Article
Keyword(s): Alnustone; Alternative medicine; Complementary medicine; Pharmacokinetics; Pharmacology; Review

Most Cited Most Cited RSS feed

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test