Skip to content
2000
Volume 21, Issue 8
  • ISSN: 1573-4072
  • E-ISSN: 1875-6646

Abstract

Bakuchiol, a meroterpene natural product found in various plants, exhibits diverse biological activities, notably anticancer properties. Researchers have synthesized numerous analogs targeting different positions, such as alcoholic OH, ethenyl, and isopropylidene groups within bakuchiol, aiming to enlighten potent therapeutic agents with enhanced pharmaceutical characteristics. The review aims to focus on the extensive potential of the bioactive molecule, bakuchiol describing SAR that may lead to the development of a variety of bakuchiol derivatives. Literature survey has been carried out to determine the potential of bakuchiol and its derivatives. This review comprehensively outlines the biosynthesis, isolation, patent, and clinical studies of bakuchiol, and pharmacological potential of bakuchiol derivatives documented to date. Additionally, it explores the structure-activity relationships observed in its derivatives. Collectively, findings from various studies underscore the significant potential of bakuchiol and its derivatives in the development of potent anticancer and other therapeutic agents. Ultimately, this review serves as a valuable resource for researchers interested in both the chemistry and biology of bakuchiol, offering insights into its multifaceted applications and paving the way for further exploration in this field.

© 2025 Bentham Science Publishers
Loading

Article metrics loading...

/content/journals/cbc/10.2174/0115734072316629240921115831
2024-10-09
2025-10-13

  • From This Site

    /content/journals/cbc/10.2174/0115734072316629240921115831
    dcterms_title,dcterms_subject,pub_keyword
    -contentType:Contributor -contentType:Concept -contentType:Institution
    10
    5
Loading full text...

Full text loading...

References

  1. LauK.M. WongJ.H. WuY.O. ChengL. WongC.W. ToM.H. LauC.P. YewD.T.W. LeungP.C. FungK.P. HuiM. NgT.B. LauC.B.S. Anti-dermatophytic activity of bakuchiol: In vitro mechanistic studies and in vivo tinea pedis-inhibiting activity in a guinea pig model.Phytomedicine201421794294510.1016/j.phymed.2014.03.005 24703327
     [Google Scholar]
  2. MehtaG. NayakU.R. DevS. Bakuchiol, a novel monoterpenoid.Tetrahedron Lett.19667384561456710.1016/S0040‑4039(00)70078‑5
     [Google Scholar]
  3. ChopraB. DhingraA.K. DharK.L. Psoralea corylifolia L. (Buguchi) — Folklore to modern evidence. [Review]Fitoterapia201390445610.1016/j.fitote.2013.06.016 23831482
     [Google Scholar]
  4. LabbéC. FainiF. CollJ. ConnollyJ.D. Bakuchiol derivatives from the leaves of Psoralea glandulosa.Phytochemistry19964251299130310.1016/0031‑9422(96)00144‑6
     [Google Scholar]
  5. HsuP.J. MillerJ.S. BergerJ.M. Bakuchiol, an antibacterial component of Psoralidium tenuiflorum.Nat. Prod. Res.200923878178810.1080/14786410902840158 19418361
     [Google Scholar]
  6. ChoiS.Y. LeeS. ChoiW.H. LeeY. JoY.O. HaT.Y. Isolation and anti-inflammatory activity of bakuchiol from Ulmus davidiana var. japonica.J. Med. Food20101341019102310.1089/jmf.2009.1207 20553183
     [Google Scholar]
  7. KreniskyJ.M. LuoJ. ReedM.J. CarneyJ.R. Isolation and antihyperglycemic activity of bakuchiol from Otholobium pubescens (Fabaceae), a Peruvian medicinal plant used for the treatment of diabetes.Biol. Pharm. Bull.199922101137114010.1248/bpb.22.1137 10549873
     [Google Scholar]
  8. LiW.D. YanC.P. WuY. WengZ.B. YinF.Z. YangG.M. CaiB.C. ChenZ.P. Osteoblasts proliferation and differentiation stimulating activities of the main components of Fructus Psoraleae corylifoliae.Phytomedicine201421440040510.1016/j.phymed.2013.09.015 24220018
     [Google Scholar]
  9. ChopraB. DhingraA. DharK.L. Antimicrobial activity of Psoralea corylifolia Linn. (Baguchi) seeds extracts by Organic Solvents and Supercritical Fluids.Int J Pharm Clinical Res2013511316
     [Google Scholar]
  10. ChoiY. YonG. HongK. YooD. ChoiC. ParkW.K. KongJ. KimY. RyuS. In vitro BACE-1 inhibitory phenolic components from the seeds of Psoralea corylifolia.Planta Med.200874111405140810.1055/s‑2008‑1081301 18666047
     [Google Scholar]
  11. WuC.Z. LiuD.C. GuoX. DaiY. MaT. LiH.M. HuoQ. Synthesis and Evaluation of Bakuchiol Derivatives as Potential Anticancer Agents.Molecules201823351510.3390/molecules23030515 29495380
     [Google Scholar]
  12. ChopraB. DhingraA.K. Therapeutic and Health Promoting Potential of Bakuchiol from Psoralea corylifolia: A Comprehensive Review.Endocr. Metab. Immune Disord. Drug Targets20232391125113610.2174/1871530323666230207123613 36748816
     [Google Scholar]
  13. ChopraB. DhingraA.K. GrewalA.S. JainA. ChaudharyJ. GroverP. Bakuchiol: A Potential Anticancer Compound from Psoralea corylifolia Linn.Anticancer. Agents Med. Chem.202323998999810.2174/1871520623666230130102910 36717993
     [Google Scholar]
  14. ZhaoG. ZangS.Y. ZhengX.W. ZhangX.H. GuoL.H. Bakuchiol analogs inhibit monoamine transporters and regulate monoaminergic functions.Biochem. Pharmacol.20087591835184710.1016/j.bcp.2008.01.014 18329002
     [Google Scholar]
  15. LauK.M. FuL.H. ChengL. WongC.W. WongY.L. LauC.P. HanS.Q.B. ChanP.K.S. FungK.P. LauC.B.S. HuiM. LeungP.C. Two antifungal components isolated from Fructus Psoraleae and Folium Eucalypti Globuli by bioassay-guided purification.Am. J. Chin. Med.20103851005101410.1142/S0192415X10008421 20821830
     [Google Scholar]
  16. AdlercreutzH. Phyto-oestrogens and cancer.Lancet Oncol.20023636437310.1016/S1470‑2045(02)00777‑5 12107024
     [Google Scholar]
  17. YuY. WangY. PiJ. GaoX. The Research Progress of Bakuchiol. J Shandong Univ Trad.Chin. Med.201337174176
     [Google Scholar]
  18. FerrándizM.L. GilB. SanzM.J. UbedaA. ErazoS. GonzálezE. NegreteR. PachecoS. PayáaM. AlcarazM.J. Effect of bakuchiol on leukocyte functions and some inflammatory responses in mice.J. Pharm. Pharmacol.201148997598010.1111/j.2042‑7158.1996.tb06016.x 8910867
     [Google Scholar]
  19. PaeH.O. ChoH. OhG.S. KimN.Y. SongE.K. KimY.C. YunY.G. KangC.L. KimJ.D. KimJ.M. ChungH.T. Bakuchiol from Psoralea corylifolia inhibits the expression of inducible nitric oxide synthase gene via the inactivation of nuclear transcription factor-κB in RAW 264.7 macrophages.Int. Immunopharmacol.200119-101849185510.1016/S1567‑5769(01)00110‑2 11562076
     [Google Scholar]
  20. ParkE.J. ZhaoY.Z. KimY.C. SohnD.H. Bakuchiol-induced caspase-3-dependent apoptosis occurs through c-Jun NH2-terminal kinase-mediated mitochondrial translocation of Bax in rat liver myofibroblasts.Eur. J. Pharmacol.20075592-311512310.1016/j.ejphar.2007.01.024 17292878
     [Google Scholar]
  21. KimK.A. ShimS.H. AhnH.R. JungS.H. Protective effects of the compounds isolated from the seed of Psoralea corylifolia on oxidative stress-induced retinal damage.Toxicol. Appl. Pharmacol.2013269210912010.1016/j.taap.2013.03.017 23545180
     [Google Scholar]
  22. XinD. WangH. YangJ. SuY.F. FanG.W. WangY.F. ZhuY. GaoX.M. Phytoestrogens from Psoralea corylifolia reveal estrogen receptor-subtype selectivity.Phytomedicine201017212613110.1016/j.phymed.2009.05.015 19577453
     [Google Scholar]
  23. LiL. ChenX. LiuC.C. LeeL.S. ManC. ChengS.H. Phytoestrogen bakuchiol exhibits in vitro and in vivo anti-breast cancer effects by inducing S phase arrest and apoptosis.Front. Pharmacol.2016712810.3389/fphar.2016.00128 27252650
     [Google Scholar]
  24. ChenZ. JinK. GaoL. LouG. JinY. YuY. LouY. Anti-tumor effects of bakuchiol, an analogue of resveratrol, on human lung adenocarcinoma A549 cell line.Eur. J. Pharmacol.20106432-317017910.1016/j.ejphar.2010.06.025 20599920
     [Google Scholar]
  25. KimJ.E. KimJ.H. LeeY. YangH. HeoY.S. BodeA.M. LeeK.W. DongZ. Bakuchiol suppresses proliferation of skin cancer cells by directly targeting Hck, Blk, and p38 MAP kinase.Oncotarget2016712146161462710.18632/oncotarget.7524 26910280
     [Google Scholar]
  26. ParkM.H. KimJ.H. ChungY.H. LeeS.H. Bakuchiol sensitizes cancer cells to TRAIL through ROS- and JNK-mediated upregulation of death receptors and downregulation of survival proteins.Biochem. Biophys. Res. Commun.2016473258659210.1016/j.bbrc.2016.03.127 27033605
     [Google Scholar]
  27. BanerjiA. ChintalwarG.J. Fate of leucine in the biosynthesis of bakuchiol, a meroterpene from Psoralea corylifolia.Indian J. Biochem. Biophys.1989266394396 2632364
     [Google Scholar]
  28. BanerjiA. ChintalwarG.J. Biosynthesis of bakuchiol from cinnamic and p-coumaric acids.Phytochemistry19842381605160610.1016/S0031‑9422(00)83449‑4
     [Google Scholar]
  29. QinT. LiuJ. BiY. WangY. LiuJ. DingG. Improved extraction efficiency of bakuchiol with antioxidant and whitening bioactivities from the seeds of Psoralea corylifolia L.Sci. Trad. Chin. Med.20231212312810.1097/st9.0000000000000014
     [Google Scholar]
  30. KhurannaD. SharmaS. MirS.R. AqilM. AhmadA. RehmanM.U. AhmadP. AlwahibiM.S. ElshikhM.S. MujeebM. Extraction, quantification, and cytokine inhibitory response of bakuchiol in Psoralea coryfolia Linn.Separations2020734810.3390/separations7030048
     [Google Scholar]
  31. YanD.M. ChangY.X. WangY.F. LiuE.W. LiJ. KangL.Y. GaoX.M. In vivo pharmacokinetics of bakuchiol after oral administration of bakuchiol extraction in rat plasma.J. Ethnopharmacol.2010128369770210.1016/j.jep.2009.12.039 20051255
     [Google Scholar]
  32. TakanoS. ShimazakiY. OgasawaraK. Enantiocontrolled synthesis of natural (+)-bakuchiol.Tetrahedron Lett.199031233325332610.1016/S0040‑4039(00)89055‑3
     [Google Scholar]
  33. BergerJ.M. ThomasM.M. RileyT.C. FlanaganK.A. ZilinskiM.V. GurunianV. -Hematin polymerization inhibition of plant extracts.J. Undergrad. Chem. Res.200653129134
     [Google Scholar]
  34. HsuP.J. Isolation, characterization, and degradation of bakuchiol from Psoralium tenuiflorum. PhD thesis, Department of Chemistry and Biochemistry, Montclair State University2006
     [Google Scholar]
  35. PouchertC.J. BehnkeJ. The Aldrich library of 13C and of 1 H FT NMR spectra.MilwaukeeAldrich Chemical Company Inc.1933Vol. 2
     [Google Scholar]
  36. ChaM.R. ChoiC.W. LeeJ.Y. KimY.S. YonG.H. ChoiS.U. RyuS.Y. Anti-proliferative effect of synthesized bakuchiol analogues on cultured human tumor cell lines.Bull. Korean Chem. Soc.20123372378238010.5012/bkcs.2012.33.7.2378
     [Google Scholar]
  37. GuptaN. SharmaS. RainaA. DangrooN.A. BhushanS. SangwanP.L. Synthesis and anti-proliferative evaluation of novel 3,4-dihydro-2H-1,3-oxazine derivatives of bakuchiol.RSC Advances2016610810615010615910.1039/C6RA23757F
     [Google Scholar]
  38. MajeedR. ReddyM.V. ChinthakindiP.K. SangwanP.L. HamidA. ChashooG. SaxenaA.K. KoulS. Bakuchiol derivatives as novel and potent cytotoxic agents: A report.Eur. J. Med. Chem.201249556710.1016/j.ejmech.2011.12.018 22245048
     [Google Scholar]
  39. ChenH. DuX. TangW. ZhouY. ZuoJ. FengH. LiY. Synthesis and structure–immunosuppressive activity relationships of bakuchiol and its derivatives.Bioorg. Med. Chem.20081652403241110.1016/j.bmc.2007.11.054 18063371
     [Google Scholar]
  40. GautamL.N. LingT. LangW. RivasF. Anti-proliferative evaluation of monoterpene derivatives against leukemia.Eur. J. Med. Chem.2016113758010.1016/j.ejmech.2016.02.034 26922230
     [Google Scholar]
  41. GuptaN. SharmaS. RainaA. BhushanS. MalikF.A. SangwanP.L. Synthesis of novel mannich derivatives of] bakuchiol as apoptotic inducer through caspase activation and PARP-1 cleavage in A549 cells.ChemistrySelect20172185196520110.1002/slct.201700504
     [Google Scholar]
  42. LiH. LiuJ. LiuC.F. LiH. LuoJ. FangS. ChenY. ZhongR. LiuS. LinS. Design, synthesis, and biological evaluation of membrane-active bakuchiol derivatives as effective broad-spectrum antibacterial agents.J. Med. Chem.20216495603561910.1021/acs.jmedchem.0c02059 33909443
     [Google Scholar]
  43. ReddyM.V. ThotaN. SangwanP.L. MalhotraP. AliF. KhanI.A. ChimniS.S. KoulS. Novel bisstyryl derivatives of bakuchiol: Targeting oral cavity pathogens.Eur. J. Med. Chem.20104573125313410.1016/j.ejmech.2010.03.049 20427099
     [Google Scholar]
  44. ManoharB. DivakarS. SankarK.U. Amyloglucosidase catalyzed syntheses of bakuchiol glycosides in supercritical carbon dioxide.Bull. Korean Chem. Soc.20093081760176610.5012/bkcs.2009.30.8.1760
     [Google Scholar]
  45. ShojiM. ArakakiY. EsumiT. KohnomiS. YamamotoC. SuzukiY. TakahashiE. KonishiS. KidoH. KuzuharaT. Bakuchiol is a phenolic isoprenoid with novel enantiomer-selective anti-influenza a virus activity involving Nrf2 activation.J. Biol. Chem.201529046280012801710.1074/jbc.M115.669465 26446794
     [Google Scholar]
  46. Adarsh KrishnaT.P. EdacheryB. AthalathilS. Bakuchiol – a natural meroterpenoid: structure, isolation, synthesis and functionalization approaches.RSC Advances202212148815883210.1039/D1RA08771A 35424800
     [Google Scholar]
  47. ThomsenK.F. BundgaardH. Cyclization-activated phenyl carbamate prodrug forms for protecting phenols against first-pass metabolism.Int. J. Pharm.1993911394910.1016/0378‑5173(93)90419‑G
     [Google Scholar]
  48. XuK. ShaY. WangS. ChiQ. LiuY. WangC. YangL. Effects of Bakuchiol on chondrocyte proliferation via the PI3K‐Akt and ERK1/2 pathways mediated by the estrogen receptor for promotion of the regeneration of knee articular cartilage defects.Cell Prolif.2019525e1266610.1111/cpr.12666 31407423
     [Google Scholar]
  49. HaraguchiH. InoueJ. TamuraY. MizutaniK. Inhibition of mitochondrial lipid peroxidation by Bakuchiol, a meroterpene from Psoralea corylifolia.Planta Med.200066656957110.1055/s‑2000‑8605 10985089
     [Google Scholar]
  50. LiuH. GuoW. GuoH. ZhaoL. YueL. LiX. FengD. LuoJ. WuX. CuiW. QuY. Bakuchiol attenuates oxidative stress and neuron damage by regulating Trx1/TXNIP and the phosphorylation of AMPK after subarachnoid hemorrhage in mice.Front. Pharmacol.20201171210.3389/fphar.2020.00712 32499702
     [Google Scholar]
  51. AdhikariS. JoshiR. PatroB.S. GhantyT.K. ChintalwarG.J. SharmaA. ChattopadhyayS. MukherjeeT. Antioxidant activity of bakuchiol: experimental evidences and theoretical treatments on the possible involvement of the terpenoid chain.Chem. Res. Toxicol.20031691062106910.1021/tx034082r 12971793
     [Google Scholar]
  52. IwamuraJ. DohiT. TanakaH. OdaniT. KuboM. Cytotoxicity of corylifoliae fructus. II. Cytotoxicity of bakuchiol and the analogues.Yakugaku Zasshi19891091296296510.1248/yakushi1947.109.12_962 2630640
     [Google Scholar]
  53. FahimA. Himratul-AznitaW.H. Abdul-RahmanP.S. Allium-sativum and bakuchiol combination: A natural alternative to Chlorhexidine for oral infections?Pak. J. Med. Sci.2020362271275 32063973
     [Google Scholar]
  54. RajuA. DeganiM.S. KhambeteM.P. RayM.K. RajanM.G.R. Antifolate activity of plant polyphenols against Mycobacterium tuberculosis.Phytother. Res.201529101646165110.1002/ptr.5437 26275674
     [Google Scholar]
  55. BacquevilleD. MaretA. NoizetM. DupratL. CoutanceauC. GeorgescuV. Bessou-TouyaS. DuplanH. Efficacy of a dermocosmetic serum combining bakuchiol and vanilla tahitensis extract to prevent skin photoaging in vitro and to improve clinical outcomes for naturally aged skin.Clin. Cosmet. Investig. Dermatol.20201335937010.2147/CCID.S235880 32494181
     [Google Scholar]
  56. NardaM. BrownA. Muscatelli-GrouxB. GrimaudJ.A. GrangerC. Epidermal and dermal hallmarks of photoaging are prevented by treatment with night serum containing melatonin, bakuchiol, and ascorbyl tetraisopalmitate: In vitro and Ex Vivo Studies.Dermatol. Ther. (Heidelb.)202010119120210.1007/s13555‑019‑00349‑8 31900804
     [Google Scholar]
  57. SinghS. AgrawalA. Ethnopharmacological, Phytochemistry and Pharmacological Activities of Psoralea Corylifolia: A Review.Int. Res. J. Ayurveda & Yoga20225511512410.47223/IRJAY.2022.5518
     [Google Scholar]
  58. NardaM. BrownA. Pérez-CremadesD. García-GiménezJ.L. GrangerC. Melatonin, bakuchiol and ascorbyl tetraisopalmitate synergize to modulate gene expression and restore hypoxia-inducible factor 1 signaling in UV-exposed skin.Cell. Mol. Biol.20186583947 32133977
     [Google Scholar]
  59. CheemaH. SinghA. PalA. BhakuniR. DarokarM. Antimalarial activity, mechanism of action and drug interaction study of active constituent isolated from the dried seeds of Psoralea corylifolia.Int. J. Pharm. Sci. Res.201793364375
     [Google Scholar]
  60. MadridA. EspinozaL. GonzálezC. MelladoM. VillenaJ. SantanderR. SilvaV. MontenegroI. Antifungal study of the resinous exudate and of meroterpenoids isolated from Psoralea glandulosa (Fabaceae).J. Ethnopharmacol.2012144380981110.1016/j.jep.2012.10.027 23099252
     [Google Scholar]
  61. SwindellW.R. BojanowskiK. SinghP. RandhawaM. ChaudhuriR.K. Bakuchiol and ethyl (linoleate/oleate) synergistically modulate endocannabinoid tone in keratinocytes and repress inflammatory pathway mRNAs.JID Innov.20233310017810.1016/j.xjidi.2022.100178 36992949
     [Google Scholar]
  62. JafernikK. HalinaE. ErcisliS. SzopaA. Characteristics of bakuchiol - the compound with high biological activity and the main source of its acquisition - Cullen corylifolium (L.).Medik. Nat. Prod. Res.202135245828584210.1080/14786419.2020.1837813 33185126
     [Google Scholar]
  63. PetricD. Bakuchiol and astaxanthin: a new weapon for sun protection?Food Health2022431610.53388/FH20220801016
     [Google Scholar]
  64. ChaudhuriR.K. BojanowskiK. Bakuchiol: a retinol‐like functional compound revealed by gene expression profiling and clinically proven to have anti‐aging effects.Int. J. Cosmet. Sci.201436322123010.1111/ics.12117 24471735
     [Google Scholar]
  65. DhaliwalS. RybakI. EllisS.R. NotayM. TrivediM. BurneyW. VaughnA.R. NguyenM. ReiterP. BosanacS. YanH. FooladN. SivamaniR.K. Prospective, randomized, double‐blind assessment of topical bakuchiol and retinol for facial photoageing.Br. J. Dermatol.2019180228929610.1111/bjd.16918 29947134
     [Google Scholar]
  66. GoldbergD.J. RobinsonD.M. GrangerC. Clinical evidence of the efficacy and safety of a new 3‐in‐1 anti‐aging topical night serum‐in‐oil containing melatonin, bakuchiol, and ascorbyl tetraisopalmitate: 103 females treated from 28 to 84 days.J. Cosmet. Dermatol.201918380681410.1111/jocd.12896 30924254
     [Google Scholar]
  67. PolákováK. FaugerA. SayagM. JourdanE. A dermocosmetic containing bakuchiol, Ginkgo biloba extract and mannitol improves the efficacy of adapalene in patients with acne vulgaris: result from a controlled randomized trial.Clin. Cosmet. Investig. Dermatol.20158187191 25914553
     [Google Scholar]
  68. ChaudhuriR.K. MarchioF. Bakuchiol in the management of acne-affected skin.Cosmet. Toiletries20111267502
     [Google Scholar]
  69. JiaQ HongMF Compositions of bakuchiol and methods of making the same.U.S. Patent 10905654B22021
     [Google Scholar]
  70. HongMF JiaQ BrownellLA Bakuchiol compositions for treatment of post inflammatory hyperpigmentation.U.S. Patent 11013699B22021
     [Google Scholar]
  71. LinHC DingHY ChangWL ChaoCL HuangHW LinCL Pharmaceutical composition containing bakuchiol for treating woman osteoporosis.U.S. Patent 7714026B22010
     [Google Scholar]
  72. ChaudhuriRK Skin treatment compositions and methods.E.P. Patent 2144590B12018
     [Google Scholar]
/content/journals/cbc/10.2174/0115734072316629240921115831
Loading
Bakuchiol and their Derivatives: Unveiling its Chemistry, SAR, Pharmacological Marvels and Therapeutic Odyssey
Curr. Bioact. Compd. 21, E15734072316629 (2025); https://doi.org/10.2174/0115734072316629240921115831
/content/journals/cbc/10.2174/0115734072316629240921115831
/content/journals/cbc/10.2174/0115734072316629240921115831
Loading

Data & Media loading...


  • Article Type:     Review Article
Keyword(s): babachi; Bakuchiol; bioactive molecule; pharmacological marvels; Psoralea corylifolia; SAR

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