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Comparison of lawsone contents among Lawsonia inermis plant parts and neurite outgrowth accelerators from branches

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Abstract

Lawsonia inermis L. (Lythraceae) is cultivated in many countries, including Japan, China, India and Egypt. Its leaves are well known as hair dye and exhibit antibacterial, anticancer, antifungal and anticonvulsant activities. However, there are few reports on its branches. 2-Hydroxy-1,4-naphthoquinone (lawsone) is a characteristic compound in its leaves. However, it remains to be clarified whether lawsone is present in other plant parts or not. In this study, we measured lawsone contents in the extracts of L. inermis flowers, leaves and branches by HPLC with tandem mass spectrometry. The extracts of L. inermis flowers, leaves and branches contained 116.9, 486.2 and 5.4 μg/g lawsone, respectively. Lawsone content was much lower in branches than the other plant parts. Next, in order to identify the biological constituents in the branches, we isolated nine known compounds and examined their effects on neurite outgrowth in PC12 cells. Among the constituents isolated, 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-propane-1,3-diol (1) and quercetin 7-O-β-D-glucopyranoside (8) showed accelerative effects on neurite outgrowth in PC12 cells.

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References

  1. Okada M, Wada H, Terabayashi S, Kondou K (2002) Newly revised illustrated medicinal plants of the world. Hokuryukan, Tokyo

    Google Scholar 

  2. Ashnagar A, Shiri A (2011) Isolation and characterization of 2-hydroxy-1,4-naphthoquinone (lawsone) from the powdered leaves of henna plant marketed in Ahwaz city of Iran. Int J Chem Tech Res 3:1941–1944

    CAS  Google Scholar 

  3. Cuong XN, Nhiem XN, Thao PN, Nam HN, Dat TN, Anh H, Huong ML, Kiem VP, Minh VC, Won J, Chung W, Kim HY (2010) Inhibitors of osteoclastogenesis from Lawsonia inermis leaves. Bioorg Med Chem Lett 20:4782–4784

    Article  PubMed  CAS  Google Scholar 

  4. Yang C, Huang H, Wang S, Sung P, Huang G, Chen J, Kuo Y (2016) New diphenol and isocoumarins from the aerial part of Lawsonia inermis and their inhibitory activities against NO production. Molecules 21:1299

    Article  CAS  Google Scholar 

  5. Liou J, El-Shazly M, Du Y, Tseng C, Hwang T, Chuang Y, Hsu Y, Hsieh P, Wu C, Chen S, Hou M, Chang F, Wu Y (2013) 1,5-Diphenylpent-3-en-1-ynes and methyl naphthalene carboxylates from Lawsonia inermis and their anti-inflammatory activity. Phytochemistry 88:67–73

    Article  PubMed  CAS  Google Scholar 

  6. Siddiqui SB, Kardar NM (2001) Triterpenoids from Lawsonia alba. Phytochemistry 58:1195–1198

    Article  PubMed  CAS  Google Scholar 

  7. Saadabi MAA (2007) Evaluation of Lawsonia inermis Linn. (Sudanese Henna) leaf extracts as an antimicrobial agent. Res J Biol Sci 2:419–423

    Google Scholar 

  8. Zumrutdal EM, Ozaslan M, Tuzcu M, Kalender EM, Daglıoglu K, Akova A, Karagöz DI, Kilic Hİ, Colak O, Köksal F (2008) Effect of Lawsonia inermis treatment on mice with sarcoma. Afr J Biotechnol 7:2781–2786

    Google Scholar 

  9. Tripathi DR, Srivastava SH, Dixit NS (1978) A fungitoxic principle from the leaves of Lawsonia inermis Lam. Experientia 34:51–52

    Article  PubMed  CAS  Google Scholar 

  10. Saikia A, Purkayastha A, Tigga R, Roy D (2016) Anticonvulsant activity of the methanolic extract of Lawsonia inermis leaves in albino rats. Int J Pharm Sci Res 7:3068–3072

    CAS  Google Scholar 

  11. Saeed MGS, Sayeed AS, Ashraf S, Naz S, Siddiqi R, Ali R, Mesaik MA (2013) A new method for the isolation and purification of lawsone from Lawsonia inermis and its ROS inhibitory activity. Pak J Bot 45:1431–1436

    CAS  Google Scholar 

  12. Nakashima S, Oda Y, Nakamura S, Liu J, Onishi K, Kawabata M, Miki H, Himuro Y, Yoshikawa M, Matsuda H (2015) Inhibitors of melanogenesis in B16 melanoma 4A5 cells from flower buds of Lawsonia inermis (Henna). Bioorg Med Chem Lett 25:2702–2706

    Article  PubMed  CAS  Google Scholar 

  13. Nakashima S, Oda Y, Nakamura S, Furukawa M, Onishi E, Matsuda H (2016) Protective effects of the flower buds of Lawsonia inermis against X-ray induced cytotoxicity. Fragr J 44:68–71

    CAS  Google Scholar 

  14. Nakashima S, Matsuda H (2013) Inhibitory effect of flower of Lawsonia inermis on AGEs production and its cell protective effect under glycated conditions. Fragr J 41:68–71

    CAS  Google Scholar 

  15. Oda Y, Nakashima S, Nakamura S, Yano M, Akiyama M, Imai K, Kimura T, Nakata A, Tani M, Matsuda H (2016) New potent accelerator of neurite outgrowth from Lawsonia inermis flower under non-fasting condition. J Nat Med 70:384–390

    Article  PubMed  CAS  Google Scholar 

  16. Greene AL, Tischler SA (1976) Establishment of a noradrenergic clonal line of rat adrenal pheochromocytoma cells which respond to nerve growth factor. Proc Natl Acad Sci USA 73:2424–2428

    Article  PubMed  CAS  Google Scholar 

  17. Marino DS, Gala F, Zollo F, Vitalini S, Fico G, Visioli F, Iorizzi M (2008) Identification of minor secondary metabolites from the latex of Croton lechleri (Muell-Arg) and evaluation of their antioxidant activity. Molecules 13:1219–1229

    Article  PubMed  CAS  Google Scholar 

  18. Li L, Seeram PN (2010) Maple syrup phytochemicals include lignans, coumarins, a stilbene, and other previously unreported antioxidant phenolic compounds. J Agric Food Chem 58:11673–11679

    Article  PubMed  CAS  Google Scholar 

  19. Fu L, Huang X, Lai Z, Hu Y, Liu H, Cai X (2008) A new 3-benzylchroman derivative from Sappan lignum (Caesalpinia sappan). Molecules 13:1923–1930

    Article  PubMed  CAS  Google Scholar 

  20. Chen T, Huang Y, Lin J, Liau B, Wang S, Wu Y, Jong T (2010) Cytotoxic lignan esters from Cinnamomum osmophloeum. Planta Med 76:613–619

    Article  PubMed  CAS  Google Scholar 

  21. Dai Z, Wang G, Lin R (2006) Chemical constituents of Balanophora simaoensis (III). Chin Trad Herb Drugs 37:1608–1610

    CAS  Google Scholar 

  22. Lee RK, Hong WS, Kwak HJ, Pyo S, Jee PO (1996) Phenolic constituents from the aerial parts of Artemisia stolonifera. Arch Pharm Res 19:231–234

    Article  CAS  Google Scholar 

  23. Slimestad R, Andersen MØ, Francis WG, Marston A, Hostettmann K (1995) Syringetin 3-O-(6″-acetyl)-β-glucopyranoside and other flavonols from needles of Norway spruce, Picea abies. Phytochemistry 40:1537–1542

    Article  CAS  Google Scholar 

  24. Saijo R, Nonaka G, Nishioka I (1989) Phenol glucoside gallates from Mallotus japonicus. Phytochemistry 28:2443–2446

    Article  CAS  Google Scholar 

  25. Kazuma K, Noda N, Suzuki M (2003) Malonylated flavonol glycosides from the petals of Clitoria ternatea. Phytochemistry 62:229–237

    Article  PubMed  CAS  Google Scholar 

  26. Markham RK, Ternai B, Stanley R, Geiger H, Mabry JT (1978) Carbon-13 NMR studies of flavonoids-III: naturally occurring flavonoid glycosides and their acylated derivatives. Tetrahedron 34:1389–1397

    Article  CAS  Google Scholar 

  27. Alluis B, Dangles O (2001) Quercetin (= 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one) glycosides and sulfates: chemical synthesis, complexation, and antioxidant properties. Helv Chim Acta 84:1133–1156

    Article  CAS  Google Scholar 

  28. Oda T, Kume T, Katsuki H, Niidome T, Sugimoto H, Akaike A (2007) Donepezil potentiates nerve growth factor-induced neurite outgrowth in PC12 cells. J Pharmacol Sci 104:349–354

    Article  PubMed  CAS  Google Scholar 

  29. Huang X, Xu Y, Bai M, Zhou L, Song S, Wang X (2017) Lignans from the seeds of Chinese hawthorn (Crataegus pinnatifida) against β-amyloid aggregation. Nat Prod Commun in press. https://doi.org/10.1080/14786419.2017.1399378

    Article  Google Scholar 

  30. Jeong M, Kim J, Zou Y, Yoon C, Lim H, Ahn J, Lee H (2010) Enhancement of pheochromocytoma nerve cell growth by consecutive fractionization of Angelica gigas Nakai extracts. Cytotechnology 62:461–472

    Article  PubMed  PubMed Central  Google Scholar 

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Authors and Affiliations

  1. Department of Pharmacognosy, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto, 607-8412, Japan

    Yoshimi Oda, Souichi Nakashima, Erina Kondo, Seikou Nakamura, Mamiko Yano, Chisa Kubota, Yusuke Masumoto, Minami Hirao, Yuki Ogawa & Hisashi Matsuda

  2. N.T.H. Co., Ltd., 1-8-11 4F Sky-ebisu Bldg., Ebisu, Shibuya-ku, Tokyo, 150-0013, Japan

    Yoshimi Oda

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  1. Yoshimi Oda
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  2. Souichi Nakashima
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  3. Erina Kondo
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  4. Seikou Nakamura
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  5. Mamiko Yano
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  9. Yuki Ogawa
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  10. Hisashi Matsuda
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Correspondence to Hisashi Matsuda.

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Oda, Y., Nakashima, S., Kondo, E. et al. Comparison of lawsone contents among Lawsonia inermis plant parts and neurite outgrowth accelerators from branches. J Nat Med 72, 890–896 (2018). https://doi.org/10.1007/s11418-018-1221-y

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  • DOI: https://doi.org/10.1007/s11418-018-1221-y

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