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A validated high-performance thin-layer chromatography method for quantification of bavachin, bakuchiol, and psoralen from Psoralea corylifolia seeds

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Abstract

A sensitive and reliable high-performance thin-layer chromatography method has been developed for the simultaneous estimation of bavachin, bakuchiol, and psoralen in Psoralea corylifolia seeds. The methanolic extract of the seeds was applied on a silica gel G 60 F254 plate. The plate was developed using toluene–ether, 1:1, saturated with 10% acetic acid (v/v) as the mobile phase and detection and quantification were performed by densitometric scanning at 254 nm. The correlation coefficients were found to be 0.999, 0.999, and 0.999 for bavachin, bakuchiol, and psoralen, respectively, in the developed method. The accuracy of the method was confirmed by conducting recovery studies at different levels using the standard addition method. The average recovery of bavachin, bakuchiol, and psoralen was found to be close to 98% confirming the accurateness of the method. The proposed method offers a new, sensitive, specific, and precise gauge for quantification of bavachin, bakuchiol, and psoralen representing all the categories of bioactive constituents in P. corylifolia.

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References

  1. Khare C (2007) Indian medicinal plants: an illustrated dictionary. Springer-Verlag, Berlin, New Delhi

    Book  Google Scholar 

  2. Batugal PA, Jayashree K, Leesok Y, Jeffrey T (2004) Medicinal plants research in Asia. Serdang, Selangor DE

    Google Scholar 

  3. Mishra S (2009) Bhiashajya Ratnavali. Chaukhambha, Varanasi

    Google Scholar 

  4. Kirtikar (1975) Indian medicinal plants. International Book Distributors, Dehradun

    Google Scholar 

  5. Warrier P, Nambiar V, Ramankutty C (1995) Indian medicinal plants. Orient Longman, Kottakal

    Google Scholar 

  6. Prajapati N, Purohit S, Sharma A, Kumar T (2004) A handbook of medicinal plants. Agrobios, Jodhpur

    Google Scholar 

  7. Dymock W, Warden C, Hooper D (2005) Pharmacographia Indica. Srishti Book Distributors, New Delhi

    Google Scholar 

  8. Tsai MH, Huang GS, Hung YC, Bin L, Liao LT, Lin LW (2007) Psoralea corylifolia extract ameliorates experimental osteoporosis in ovariectomized rats. Am J Chin Med 35:669–680. https://doi.org/10.1142/S0192415X07005168

    Article  PubMed  Google Scholar 

  9. Weng ZB, Gao QQ, Wang F et al (2015) Positive skeletal effect of two ingredients of Psoralea corylifolia L. on estrogen deficiency-induced osteoporosis and the possible mechanisms of action. Mol Cell Endocrinol 417:103–113. https://doi.org/10.1016/j.mce.2015.09.025

    Article  CAS  PubMed  Google Scholar 

  10. Qamaruddin A, Parveen N, Khan NU, Singhal KC (2002) Potential antifilarial activity of the leaves and seeds extracts of Psoralea corylifolia on cattle filarial parasite Setaria cervi. J Ethnopharmacol 82:23–28. https://doi.org/10.1016/s0378-8741(02)00141-1

    Article  CAS  PubMed  Google Scholar 

  11. Alam F, Khan GN, Hassham M, Asad HB (2017) Psoralea corylifolia L.: Ethnobotanical, biological, and chemical aspects: a review. Phytother Res 1–19. https://doi.org/10.1002/ptr.6006

  12. Liu R, Li A, Sun A, Kong L (2004) Preparative isolation and purification of psoralen and isopsoralen from Psoralea corylifolia by high-speed counter-current chromatography. J Chromatogr A1057:225–228. https://doi.org/10.1016/j.chroma.2004.09.049

    Article  CAS  Google Scholar 

  13. Qiao CF, Han QB, Mo SF, Song JZ, Xu LJ, Chen SL, Yang DJ, Kong LD, Kung HF, Xu HX (2006) Psoralenoside andisopsoralenoside, two new benzofuran glycosides from Psoralea corylifolia. Chem Pharm Bull 54:714–716. https://doi.org/10.1248/cpb.54.714

    Article  CAS  PubMed  Google Scholar 

  14. Khastgir HN, Duttagupta PC, Sengupta P (1961) The structure of psoralidin. Tetrahedron 14:275–283. https://doi.org/10.1016/S0040-4020(01)92176-3

    Article  Google Scholar 

  15. Liu X, Nam JW, Song YS, Viswanath ANI, Pae AN, Kil YS, Kim HD, Park JH, Seo EK, Chang M (2014) Psoralidin, a coumestan analogue, as a novel potent estrogen receptor signaling molecule isolated from Psoralea corylifolia. Bioorg Med Chem Lett 24:1403–1406. https://doi.org/10.1016/j.bmcl.2014.01.029

    Article  CAS  PubMed  Google Scholar 

  16. Yadava RN, Verma V (2005) A new biologically active flavonol glycoside from Psoralea corylifolia (Linn.). J Asian Nat Prod Res 7:671–675. https://doi.org/10.1080/10286020310001608921

    Article  CAS  PubMed  Google Scholar 

  17. Bhalla VK, Nayak UR, Dev S (1968) Tetrahedron Lett 24:2401–2406

    Article  Google Scholar 

  18. Yin S, Fan CQ, Dong L, Yue JM (2006) Psoracorylifols A–E, five novel compounds with activity against Helicobacter pylori from seeds of Psoralea corylifolia. Tetrahedron 62:2569–2575. https://doi.org/10.1016/j.tet.2005.12.041

    Article  CAS  Google Scholar 

  19. Haraguchi H, Inoue J, Tamura Y, Mizutani K (2002) Antioxidative components of Psoralea corylifolia (Leguminosae). Phytother Res 16:539–544. https://doi.org/10.1002/ptr.972

    Article  CAS  PubMed  Google Scholar 

  20. Gupta SR, Seshadri TR, Sood GR (1997) The structure and synthesis of neobavachalcone, a new component of Psoralea corylifolia. Phytochemistry 16:1995–1997. https://doi.org/10.1016/0031-9422(77)80111-8

    Article  Google Scholar 

  21. Sun NJ, Woo SH, Cassady JM, Snapka RM (1998) DNA polymerase and topoisomerase II inhibitors from Psoralea corylifolia. J Nat Prod 61:362–366. https://doi.org/10.1021/np970488q

    Article  CAS  PubMed  Google Scholar 

  22. Yin S, Fan CX, Wang Y et al (2004) Antibacterial prenylflavone derivatives from Psoralea corylifolia, and their structure–activity relationship study. Bioorg Med Chem 12:4387–4392. https://doi.org/10.1016/j.bmc.2004.06.014

    Article  CAS  PubMed  Google Scholar 

  23. Li WD, Yan CP, Wu Y, Weng ZB et al (2014) Osteoblasts proliferation and differentiation stimulating activities of the main components of Fructus Psoraleae corylifoliae. Phytomedicine 21:400–405. https://doi.org/10.1159/000492554

    Article  CAS  PubMed  Google Scholar 

  24. Mehta G, Nayak UR, Dev S (1973) Meroterpenoids –I. Psoralea corylifolia Linn. – 1. Bakuchiol, a novel monoterpene phenol. Tetrahedron 29:1119–1125. https://doi.org/10.1016/0040-4020(73)80071-7

    Article  CAS  Google Scholar 

  25. Shah CC, Bhalla VK, Dev S (1997) J Indian Chem Soc 74:970–973

    CAS  Google Scholar 

  26. Li L, Chen X, Liu CC, Lee LS, Man C, Cheng SH (2016) Phytoestrogen bakuchiol exhibits in vitro and in vivo anti-breast cancer effects by inducing S phase arrest and apoptosis. Front Pharmacol 7:128. https://doi.org/10.3389/fphar.2016.00128

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. Iwamura J, Dohi T, Tanaka H, Odani T, Kubo M (1989) Cytotoxixity of Corylifoliaefructus. Cytotoxicity of bakuchiol and its analogue. J Pharm Soc 109:962–965. https://doi.org/10.1248/yakushi1947.109.12_962

    Article  CAS  Google Scholar 

  28. Katsura H, Tsukiyama RI, Suzuki A, Kobayashi M (2001) In vitro antimicrobial activities of bakuchiol against oral microorganisms. Antimicrob Agents Chemother 45:3009–3013. https://doi.org/10.1128/AAC.45.11.3009-3013.2001

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Newton SM, Lau C, Gurcha SS, Besra GS, Wright CW (2002) The evaluation of forty-three plant species for in vitro antimycobacterial activities; isolation of active constituents from Psoralea corylifolia and Sanguinaria canadensis. J Ethnopharmacol 9:57–67. https://doi.org/10.1016/s0378-8741(01)00350-6

    Article  Google Scholar 

  30. Lau K-M, Fu L-H, Cheng L et al (2010) Two antifungal components isolated from Fructus Psoraleae and Folium Eucalypti Globuli by bioassay-guided purification. Am J Chin Med 38:1005–1014. https://doi.org/10.1142/S0192415X10008421

    Article  PubMed  Google Scholar 

  31. Lau KM, Wong JH, Wu YO et al (2014) Anti-dermatophytic activity of bakuchiol: In vitro mechanistic studies and in vivo tinea pedis-inhibiting activity in a Guinea pig model. Phytomedicine 21:942–945. https://doi.org/10.1016/j.phymed.2014.03.005

    Article  CAS  PubMed  Google Scholar 

  32. Prasad NR, Anandi C, Balasubramanian S, Pugalendi K (2004) Antidermatophytic activity of extracts from Psoralea corylifolia (Fabaceae) correlated with the presence of a flavonoid compound. J Ethnopharmacol 91:21–24. https://doi.org/10.1016/j.jep.2003.11.010

  33. Savoia D (2012) Plant-derived antimicrobial compounds: alternatives to antibiotics. Future Microbiol 7:979–990. https://doi.org/10.2217/fmb.12.68

    Article  CAS  PubMed  Google Scholar 

  34. Srinivasan S, Sarada DVL (2012) Antifungal activity of phenyl derivative of pyranocoumarin from Psoralea corylifolia L. seeds by inhibition of acetylation activity of trichothecene 3-o-acetyltransferase (Tri101). J Biomed Biotechnol 1–8. https://doi.org/10.1155/2012/310850

  35. Yang X, Li J, Wang X, Fang W, Bidochka MJ, She R, Xiao Y, Pei Y (2006) Psc-AFP, an antifungal protein with trypsin inhibitor activity from Psoralea corylifolia seeds. Peptides 27:1726–1731. https://doi.org/10.1016/j.peptides.2006.01.020

    Article  CAS  PubMed  Google Scholar 

  36. Chai L, Zhou K, Wang S et al (2018) Psoralen and bakuchiol ameliorate M-CSF plus RANKL-induced osteoclast differentiation and bone resorption via inhibition of AKT and AP-1 pathways in vitro. Cell Physiol Biochem 48:2123–2133. https://doi.org/10.1159/000492554

    Article  CAS  PubMed  Google Scholar 

  37. Seo E, Oh YS, Kim D (2013) Protective role of Psoralea corylifolia L. seed extract against hepatic mitochondrial dysfunction induced by oxidative stress or aging. Evid-Based Compl Alt 2013:1–9. https://doi.org/10.1155/2013/678028.678028

    Article  Google Scholar 

  38. Wang YF, Wu B, Yang J (2009) A rapid method for the analysis of ten compounds in Psoralea corylifolia L. by UPLC. Chromatographia 70:199–204. https://doi.org/10.1365/s10337-009-1118-8

    Article  CAS  Google Scholar 

  39. Qiao CF, Han QB, Song JZ (2007) Chemical fingerprint and quantitative analysis of Fructus Psoraleae by high-performance liquid chromatography. J Sep Sci 30:813–818. https://doi.org/10.1002/jssc.200600339

    Article  CAS  PubMed  Google Scholar 

  40. Zhao LH, Huang CY, Shan Z (2005) Fingerprint analysis of Psoralea corylifolia L. by HPLC and LC–MS. J Chromatogr B 821:67–74. https://doi.org/10.1016/j.jchromb.2005.04.008

    Article  CAS  Google Scholar 

  41. Chen XG, Kong L, Su XY (2005) Integration of ion-exchange chromatography fractionation with reversed-phase liquid chromatography-atmospheric pressure chemical ionization mass spectrometer and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for isolation and identification of compounds in Psoralea corylifolia. J Chromatogr A 1089:87–100. https://doi.org/10.1016/j.chroma.2005.06.067

    Article  CAS  PubMed  Google Scholar 

  42. Xiao GD, Li GW, Chen LA (2010) Isolation of antioxidants from Psoralea corylifolia fruits using high-speed counter-current chromatography guided by thin layer chromatography-antioxidant autographic assay. J Chromatogr A1217:5470–5476. https://doi.org/10.1016/j.chroma.2010.06.041

    Article  CAS  Google Scholar 

  43. Wang DX, Yang GL, Engelhardt H, Zhang H (1999) Micellar electrokinetic capillary chromatography of psoralen and isopsoralen. Electrophoresis 20:1895–1899

    Article  CAS  Google Scholar 

  44. Shrestha S, Jadav HR, Bedarkar P, Patgiri BJ, Harisha CR, Chaudhari SY, Prajapati PK (2018) Pharmacognostical evaluation of Psoralea corylifolia Linn. seed. J Ayurveda Integr Med 9:209–212. https://doi.org/10.1016/j.jaim.2017.05.005

    Article  PubMed  PubMed Central  Google Scholar 

  45. International Conference on Harmonization, Q2 (R1) Validation of analytical procedures, Text and methodology, Geneva, 2005

  46. Murali B, Amit A, Anand MS, Venkataraman BV (2002) An HPLC method for simultaneous estimation of psoralen, bakuchicin and bakuchiol in Psoralea corylifolia. J Nat Rem 2:76–80. https://doi.org/10.18311/jnr/2002/349

    Article  CAS  Google Scholar 

  47. Kim YJ, Lim HS, Lee J, Jeong SJ (2016) Quantitative analysis of Psoralea corylifolia Linne and its neuroprotective and anti-neuroinflammatory effects in HT22 hippocampal cells and BV-2 microglia. Molecules 21:1076–1086. https://doi.org/10.3390/molecules21081076

    Article  CAS  PubMed Central  Google Scholar 

  48. Yan C, Wu Y, Weng Z, Gao Q, Yang G, Chen Z, Cai B, Li W (2015) Development of an HPLC method for absolute quantification and QAMS of flavonoids components in Psoralea corylifolia L. J Anal Methods Chem 23:1–7. https://doi.org/10.1155/2015/792637

    Article  CAS  Google Scholar 

  49. Chen Q, Li Y, Chen Z (2012) Separation, identification, and quantification of active constituents in Fructus Psoraleae by high-performance liquid chromatography with UV, ion trap mass spectrometry, and electrochemical detection. J Pharm Anal 2:143–151. https://doi.org/10.1016/j.jpha.2011.11.005

    Article  CAS  PubMed  Google Scholar 

  50. Honigsmann H, Fitzpatrick TB, Pathak MA et al (1987) Oral photochemotherapy with psoralen and UVA (PUVA): principles and practice. In: Fitzpatrick TB, Eisen AZ, Wolf K (eds) Dermatology in general medicine. McGraw-Hill, New York, pp 1728–1754

    Google Scholar 

  51. Bethea D, Fullmer B, Syed S, Seltzer G, Tiano J, Rischko C, Gillespie L, Brown D, Gasparro FP (1999) Psoralen photobiology and photochemotherapy: 50 years of science and medicine. J Dermatol Sci 19:78–88. https://doi.org/10.1016/S0923-1811(98)00064-4

    Article  CAS  PubMed  Google Scholar 

  52. Stern RS (2007) Psoralen and ultraviolet a light therapy for psoriasis. N Engl J Med 357:682–690

    Article  CAS  Google Scholar 

  53. Chaudhuri R (2015) Bakuchiol: a retinol-like functional compound, modulating multiple retinol and non-retinol targets. In: Sivamani RS, Jagdeo J, Elsner P, Maibach HI (eds) Cosmeceuticals and active cosmetics, 3rd edn. Taylor & Francis, Oxfordshire, pp 1–18. https://doi.org/10.1201/b18895-2

    Chapter  Google Scholar 

  54. Fisher GJ, Voorhees JJ (1996) Molecular mechanism of retinoid actions in skin. FASEB J 10:1002–1013

    Article  CAS  Google Scholar 

  55. Chaudhuri RK (2010) The miracle of retinol. Soap Perfum Cosmetics 2–24

  56. Chaudhuri RK, Bojanowski K (2014) Bakuchiol. A retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects. Int J Cosmet Sci 36:221–230

    Article  CAS  Google Scholar 

  57. Wang D, Li F, Jiang Z (2001) Osteoblastic proliferation stimulating activity of Psoralea corylifolia extracts and two of its flavonoids. Planta Med 67:748–749. https://doi.org/10.1055/s-2001-18343

    Article  CAS  PubMed  Google Scholar 

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  1. Department of Pharmacognosy, L. M. College of Pharmacy, Navrangpura, Ahmedabad, Gujarat, 380009, India

    Ishita A. Basera & Mamta B. Shah

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Basera, I.A., Shah, M.B. A validated high-performance thin-layer chromatography method for quantification of bavachin, bakuchiol, and psoralen from Psoralea corylifolia seeds. JPC-J Planar Chromat 33, 293–300 (2020). https://doi.org/10.1007/s00764-020-00037-w

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