Journal of Natural Medicines

, Volume 71, Issue 1, pp 299–304 | Cite as

Pteleifolols A–E, acetophenone di-C-glycosides and a benzopyran dimer from the leaves of Melicope pteleifolia

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Abstract

Four new acetophenone di-C-glycosides, pteleifolols A–D (1–4) and a new dimeric benzopyran, pteleifolol E (5), were isolated from the leaves of Melicope pteleifolia. Seven known compounds, including 2,4,6-trihydroxyacetophenone-3,5-di-C-glucopyranoside (6), were also isolated. Structures of the new compounds (1–5) were established by using spectroscopic and spectrometric techniques, including 1D and 2D nuclear magnetic resonance (NMR), UV, and high-resolution electrospray ionization mass spectrometry (HR-ESI–MS) data. Pteleifolols A–D (1–4) were E-p-coumaroyl, Z-p-coumaroyl, E-feruloyl, and benzoyl esters of 6, respectively. Pteleifolol E (5) was a dichromene dimerized through a C2 unit.

Keywords

Melicope pteleifolia Rutaceae Acetophenone Dimeric benzopyran Pteleifolols A–E 
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References

  1. 1.
    Hartley TG (2001) On the taxonomy and biogeography of Euodia and Melicope. Allertonia 8:1–319Google Scholar
  2. 2.
    Nakashima K, Oyama M, Ito T, Murata H, Iinuma M (2011) New furanocoumarins from the fruits of Melicope triphylla. Heterocycles 83:1603–1610. doi: 10.3987/COM-11-12228 CrossRefGoogle Scholar
  3. 3.
    Nakashima K, Oyama M, Ito T, Witono JR, Darnaedi D, Tanaka T, Murata J, Iinuma M (2012) Novel zierane- and guaiane-type sesquiterpenes from the root of Melicope denhamii. Chem Biodivers 9:2195–2202. doi: 10.1002/cbdv.201100345 CrossRefPubMedGoogle Scholar
  4. 4.
    Nakashima K, Oyama M, Ito T, Akao Y, Witono JR, Darnaedi D, Tanaka T, Murata J, Iinuma M (2012) Novel quinolinone alkaloids bearing a lignoid moiety and related constituents in the leaves of Melicope denhamii. Tetrahedron 68:2421–2428. doi: 10.1016/j.tet.2012.01.007 CrossRefGoogle Scholar
  5. 5.
    Oyama M, Nakashima K, Kamiya T, Haba M, Ito T, Murata H, Tanaka T, Adachi T, Iinuma M, Kinoshita T (2013) Flavonoids isolated from the leaves of Melicope triphylla and their extracellular-superoxide dismutase-inducing activity. Phytochem Lett 6:215–218. doi: 10.1016/j.phytol.2013.01.007 CrossRefGoogle Scholar
  6. 6.
    Kamperdick C, Van NH, Sung TV, Adam G (1997) Benzopyrans from Melicope ptelefolia leaves. Phytochemistry 45:1049–1056. doi: 10.1016/S0031-9422(97)00059-9 CrossRefGoogle Scholar
  7. 7.
    Li SG, Tian HY, Ye WC, Jiang RW (2011) Benzopyrans and furoquinoline alkaloids from Melicope pteleifolia. Biochem Syst Ecol 39:64–67. doi: 10.1016/j.bse.2011.01.005 CrossRefGoogle Scholar
  8. 8.
    Xu J, Sun X, Liu X, Peng M, Li S, Jin D-Q, Lee D, Bartlam M, Guo Y (2016) Phytochemical constituents from Melicope pteleifolia that promote neurite outgrowth in PC12 cells. J Funct Foods 23:565–572. doi: 10.1016/j.jff.2016.03.011 CrossRefGoogle Scholar
  9. 9.
    Van NH, Kamperdick C, Sung TV, Adam G (1998) Benzopyran dimers from Melicope ptelefolia. Phytochemistry 48:1055–1057. doi: 10.1016/S0031-9422(97)00613-4 CrossRefGoogle Scholar
  10. 10.
    Li GL, Zhu DY (1998) Two new dichromenes from Evodia lepta. J Nat Prod 61:390–391. doi: 10.1021/np9704516 CrossRefPubMedGoogle Scholar
  11. 11.
    Li GL, Zhu DY (1999) Two dichromenes from Evodia lepta. J Asian Nat Prod 1:337–341CrossRefGoogle Scholar
  12. 12.
    Xu J-F, Zhao H-J, Wang X-B, Li Z-R, Luo J, Yang M-H, Yang L, Yu W-Y, Yao H-Q, Luo J-G, Kong L-Y (2015) (±)-Melicolones A and B, rearranged prenylated acetophenone stereoisomers with an unusual 9-oxatricyclo[3.2.1.13,8]nonane core from the leaves of Melicope ptelefolia. Org Lett 17:146–149. doi: 10.1021/ol5033738 CrossRefPubMedGoogle Scholar
  13. 13.
    Chen KT, Lin LC, Chou CJ, Chen CF (1994) A novel acetophenone di-C-glycoside from Melicope pteleifolia fruit. Chin Pharm J (Taipei) 46:165–174Google Scholar
  14. 14.
    Zhang Y, Yang LJ, Jiang K, Tan JJ, Yang PM, Zhu DY (2012) Glycosidic constituents from the roots and rhizomes of Melicope pteleifolia. Carbohydr Res 361:114–119. doi: 10.1016/j.carres.2012.08.011 CrossRefPubMedGoogle Scholar
  15. 15.
    Manandhar MD, Hussaini FA, Kapil RS, Shoeb A (1985) Bacteriostatic heterocycles from Euodia lunu-ankenda. Phytochemistry 24:199–200. doi: 10.1016/S0031-9422(00)80844-4 CrossRefGoogle Scholar
  16. 16.
    Li G, Jiafeng Z, Zhu D (1997) Isolation and identification of four new 2,2-dimethylchromones. Yao Xue Xue Bao 32:682–684PubMedGoogle Scholar
  17. 17.
    Pusset J, Lopez JL, Pais M, Neirabeyeh MA, Veillon JM (1991) Isolation and 2D NMR studies of Alkaloids from Comptonella sessilifoliola. Planta Med 57:153–155. doi: 10.1055/s-2006-960053 CrossRefPubMedGoogle Scholar
  18. 18.
    Cullmann F, Becker H (1999) Lignans from the liverwort Lepicolea ochroleuca. Phytochemistry 52:1651–1656. doi: 10.1016/S0031-9422(99)00372-6 CrossRefGoogle Scholar
  19. 19.
    Blas B, Zapp J, Becker H (2004) ent-Clerodane diterpenes and other constituents from the liverwort Adelanthus lindenbergianus (Lehm.) Mitt. Phytochemistry 65:127–137. doi: 10.1016/S0031-9422(03)00387-X CrossRefPubMedGoogle Scholar
  20. 20.
    Nguyen NH, Ha TK, Choi S, Eum S, Lee CH, Bach TT, Chinh VT, Oh WK (2016) Chemical constituents from Melicope pteleifolia leaves, Phytochemistry, (in press). doi: 10.1016/j.phytochem.2016.06.011
  21. 21.
    Brophy JJ, Goldsack RJ, Forster PI (2004) The leaf oils of the Australian species of Medicosma (Rutaceae). J Essent Oil Res 16:161–166. doi: 10.1080/10412905.2004.9698683 CrossRefGoogle Scholar
  22. 22.
    Baldwin ME, Bick IRC, Komzak AA, Price JR (1961) Some ketones from Acradenia franklinii. Tetrahedron 16:206–211. doi: 10.1016/0040-4020(61)80072-0 CrossRefGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan 2016

Authors and Affiliations

  1. 1.Laboratory of Medicinal Resources, School of PharmacyAichi Gakuin UniversityNagoyaJapan
  2. 2.Department of Bioactive Molecules, Laboratory of PharmacognosyGifu Pharmaceutical UniversityGifuJapan
  3. 3.Graduate Institute of Natural Products, College of PharmacyKaohsiung Medical UniversityKaohsiungTaiwan

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