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Four new glucosides from the aerial parts of Mediasia macrophylla

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Abstract

As part of our chemical studies on the medical plants in Uzbekistan aimed at searching for new drug leads, we have examined the aerial parts of Mediasia macrophylla. This has resulted in the isolation of four new glucosides, together with 30 known compounds. The structures of new compounds were elucidated as (1′S)-(4-hydroxyphenyl) ethane-1′,2′-diol 2′-O-β-glucopyranoside (1), 3-(4′-methoxyphenyl)-propanol 1-O-β-glucopyranoside (2), 2-methoxy-3-hydroxy-5-(E)-propenyl-phenol 1-O-β-glucopyranoside (3), 1-O-angeloyl-β-glucopyranose (4), on the basis of spectral analysis.

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References

  1. Chen B, Kawazoe K, Takaishi Y, Honda G, Itoh M, Takeda Y, Kodzhimatov OK, Ashurmetov O (2000) Prenylated benzoic acid derivatives from Ferula kuhistanica. J Nat Prod 63:362–365

    Article  CAS  PubMed  Google Scholar 

  2. Duan H, Takaishi Y, Tori M, Takaoka S, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O (2002) Polysulfide derivatives from Ferula foetida. J Nat Prod 65:1667–1669

    Article  CAS  PubMed  Google Scholar 

  3. Shikishima Y, Takaishi Y, Honda G, Ito M, Takeda Y, Tori M, Takaoka S, Kodzhimatov OK, Ashurmetov O (2002) Sesquiterpenes from Ferula penninervis. J Nat Prod 65:1897–1903

    Article  CAS  PubMed  Google Scholar 

  4. Su BN, Takaishi Y, Honda G, Itoh M, Takeda Y, Kodzhimatov OK, Ashurmetov O (2000) Sesquiterpene phenylpropanoid and sesquiterpene chromone derivatives from Ferula pallida. J Nat Prod 63:520–522

    Article  CAS  PubMed  Google Scholar 

  5. Su BN, Takaishi Y, Honda G, Itoh M, Takeda Y, Kodzhimatov OK, Ashurmetov O (2000) Sesquiterpene coumarins and related derivatives from Ferula pallida. J Nat Prod 63:436–440

    Article  CAS  PubMed  Google Scholar 

  6. Suzuki K, Okasaka M, Kashiwada Y, Takaishi Y, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O, Sekiya M, Ikeshiro Y (2007) Sesquiterpene lactones from the roots of Ferula varia and their cytotoxic activity. J Nat Prod 70:1915–1918

    Article  CAS  PubMed  Google Scholar 

  7. Tada Y, Shikishima Y, Takaishi Y, Shibata H, Higuti T, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O, Ohmoto Y (2002) Coumarins and γ-pyrone derivatives from Prangos pabularia: antibacterial activity and inhibition of cytokine release. Phytochemistry 59:649–654

    Article  CAS  PubMed  Google Scholar 

  8. Tamemoto K, Takaishi Y, Chen B, Kawazoe K, Shibata H, Higuti T, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O (2001) Sesquiterpenoids from the fruits of Ferula kuhistanica and antibacterial activity of the constituents of F. kuhistanica. Phytochemistry 58:763–767

    Article  CAS  PubMed  Google Scholar 

  9. Tamemoto K, Takaishi Y, Kawazoe K, Honda G, Ito M, Kiuchi F, Takeda Y, Kodzhimatov OK, Ashurmetov O, Shimizu K, Nagasawa H, Uto Y, Hori H (2002) An unusual sesquiterpene derivative from Ferula kuhistanica. J Nat Prod 65:1323–1324

    Article  CAS  PubMed  Google Scholar 

  10. Zhou P, Takaishi Y, Duan H, Chen B, Honda G, Itoh M, Takeda Y, Kodzhimatov OK, Lee KH (2000) Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release. Phytochemistry 53:689–697

    Article  CAS  PubMed  Google Scholar 

  11. Fu B, Su BN, Takaishi Y, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O (2001) A bis-sesquiterpene and sesquiterpenolides from Inula macrophylla. Phytochemistry 58:1121–1128

    Article  CAS  PubMed  Google Scholar 

  12. Su BN, Takaishi Y, Tori M, Takaoka S, Honda G, Itoh M, Takeda Y, Kodzhimatov OK, Ashurmetov O (2000) Macrophyllidimers A and B, two novel sesquiterpene dimers from the bark of Inula macrophylla. Tetrahedron Lett 41:1475–1479

    Article  CAS  Google Scholar 

  13. Su BN, Takaishi Y, Tori M, Takaoka S, Honda G, Itoh M, Takeda Y, Kodzhimatov OK, Ashurmetov O (2000) Macrophyllols A and B, two unusual novel sesquiterpene and monoterpene dimers from the bark of Inula macrophylla. Org Lett 2:493–496

    Article  CAS  PubMed  Google Scholar 

  14. Su BN, Takaishi Y, Yabuuchi T, Kusumi T, Tori M, Takaoka S, Honda G, Itoh M, Takeda Y, Kodzhimatov OK, Ashurmetov O (2001) Sesquiterpenes and monoterpenes from the bark of Inula macrophylla. J Nat Prod 64:466–471

    Article  CAS  PubMed  Google Scholar 

  15. Matsuhisa M, Shikishima Y, Takaishi Y, Honda G, Ito M, Takeda Y, Shibata H, Higuti T, Kodzhimatov OK, Ashurmetov O (2002) Benzoylphloroglucinol derivatives from Hypericum scabrum. J Nat Prod 65:290–294

    Article  CAS  PubMed  Google Scholar 

  16. Tanaka N, Takaishi Y, Shikishima Y, Nakanishi Y, Bastow K, Lee KH, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O (2004) Prenylated benzophenones and xanthones from Hypericum scabrum. J Nat Prod 67:1870–1875

    Article  CAS  PubMed  Google Scholar 

  17. Okasaka M, Takaishi Y, Kogure K, Fukuzawa K, Shibata H, Higuti T, Honda G, Ito M, Kodzhimatov OK, Ashurmetov O (2004) New stilbene derivatives from Calligonum leucocladum. J Nat Prod 67:1044–1046

    Article  CAS  PubMed  Google Scholar 

  18. Okasaka M, Takaishi Y, Kashiwada Y, Kodzhimatov OK, Ashurmetov O, Lin AJ, Consentino LM, Lee KH (2006) Terpenoids from Juniperus polycarpus var seravschanica. Phytochemistry 67:2635–2640

    Article  CAS  PubMed  Google Scholar 

  19. Okasaka M, Kashiwada Y, Kodzhimatov OK, Ashurmetov O, Takaishi Y (2008) Monoterpene glycosides from Paeonia hybrida. Phytochemistry 69:1767–1772

    Article  CAS  PubMed  Google Scholar 

  20. Chernenko TV, Glushenkova AI, Nigmatullaev AM (2002) Lipids from Mediasia macrophylla leaves. Chem Nat Compd 38:307–309

    Article  CAS  Google Scholar 

  21. Kurimoto S, Okasaka M, Kashiwada Y, Kodzhimatov OK, Takaishi Y (2010) A C14-polyacetylenic glucoside with an α-pyrone moiety and four C10-polyacetylenic glucosides from Mediasia macrophylla. Phytochemistry 71:688–692

    Article  CAS  PubMed  Google Scholar 

  22. Ishikawa T, Kondo K, Kitajima J (2003) Water-soluble constituents of coriander. Chem Pharm Bull 51:32–39

    Article  CAS  PubMed  Google Scholar 

  23. Uaui T, Sakata K, Watanabe S, Ishikami M, Oka N, Okada M, Yamagishi M, Oishi K, Ota T, Tozuka Y (2006) Jpn Kokai Tokkyo Koho JP 3765648 B2

  24. Lin HC, Ding HY, Wu TS, Wu PL (1996) Monoterpene glycosides from Paeonia suffruticosa. Phytochemistry 41:237–242

    Article  CAS  Google Scholar 

  25. Ishikawa T, Kitajima J, Tanaka Y (1998) Water-soluble constituents of fennel. III. Fenchane-type monoterpenoid glycosides. Chem Pharm Bull 46:1599–1602

    CAS  Google Scholar 

  26. Orihara Y, Furuya T (1994) Biotransformation of 1, 8-cineole by cultured cells of Eucalyptus perriniana. Phytochemistry 35:641–644

    Article  CAS  Google Scholar 

  27. Kong LD, Abliz Z, Zhou CX, Li LJ, Cheng CHK, Tan RX (2001) Glycosides and xanthine oxidase inhibitors from Conyza bonariensis. Phytochemistry 58:645–651

    Article  CAS  PubMed  Google Scholar 

  28. Ishikawa T, Tanaka Y, Kitajima J (1998) Water-soluble constituents of fennel VII. Acyclic monoterpenoid glycosides. Chem Pharm Bull 46:1748–1751

    CAS  Google Scholar 

  29. Lee AL, Ley SV (2003) The synthesis of the anti-malarial natural product polysphorin and analogues using polymer-supported reagents and scavengers. Org Biomol Chem 1:3957–3966

    Article  CAS  PubMed  Google Scholar 

  30. Matsuura H, Miyazaki H, Asakawa C, Amano M, Yoshihara T, Mizutani J (2004) Isolation of α-glucosidase inhibitors from hyssop (Hyssopus officinalis). Phytochemistry 65:91–97

    Article  CAS  PubMed  Google Scholar 

  31. Cheninat A, Zawatzky R, Becker H, Brouillard R (1988) Caffeoyl conjugates from Echinacea species: structures and biological activity. Phytochemistry 27:2787–2794

    Article  Google Scholar 

  32. Ida Y, Satoh Y, Ohtsuka M, Nagasao M, Shoji J (1994) Phenolic constituents of Phellodendron amurense bark. Phytochemistry 35:209–215

    Article  CAS  Google Scholar 

  33. Kitajima J, Ishikawa T, Tanaka Y, Ono M, Ito Y, Nohara T (1998) Water-soluble constituents of fennel V. Glycosides of aromatic compounds. Chem Pharm Bull 46:1587–1590

    CAS  Google Scholar 

  34. Achenbach H, Stoecker M, Constenla MA (1988) Flavonoid and other constituents of Bauhinia manca. Phytochemistry 27:1835–1841

    Article  CAS  Google Scholar 

  35. Inoshiri S, Sasaki M, Kohda H, Otsuka H, Yamasaki K (1987) Aromatic glycosides from Berchemia racemosa. Phytochemistry 26:2811–2814

    Article  CAS  Google Scholar 

  36. Yousef GG, Grace MH, Cheng DM, Belolipov IV, Raskin I, Lila MA (2006) Comparative phytochemical characterization of three Rhodiola species. Phytochemistry 67:2380–2391

    Article  CAS  PubMed  Google Scholar 

  37. Schwab W, Schreier P (1988) Aryl β-d-glucosides from Carica papaya fruit. Phytochemistry 27:1813–1816

    Article  CAS  Google Scholar 

  38. Miyase T, Ueno A, Takizawa N, Kobayashi H, Oguchi H (1989) Ionone and lignan glycosides from Epimedium diphyllum. Phytochemistry 28:3483–3485

    Article  CAS  Google Scholar 

  39. Matsumura T, Ishikawa T, Kitajima J (2002) Water-soluble constituents of caraway: aromatic compound, aromatic compound glucoside and glucosides. Phytochemistry 61:455–459

    Article  CAS  PubMed  Google Scholar 

  40. Sumarah MW, Puniani E, Blackwell BA, Miller JD (2008) Characterization of polyketide metabolites from foliar endophytes of Picea glauca. J Nat Prod 71:1393–1398

    Article  CAS  PubMed  Google Scholar 

  41. Fujiwara T, Honjo T (1995) Determination of constituents in fruit juice by near infrared spectroscopy Part I. Determination of sugar and acid contents in fruit juice of satsuma mandarin by near infrared spectroscopy. Nippon Shokuhin Kagaku Kogaku Kaishi 42:109–117

    Google Scholar 

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

    Article  CAS  Google Scholar 

  43. Tsukamoto H, Hisada S, Nishibe S (1985) Coumarin and secoiridoid glucosides from bark of Olea africana and Olea capensis. Chem Pharm Bull 33:396–399

    CAS  Google Scholar 

  44. Abe F, Yamauchi T (1988) 9α-Hydroxypinoresinol, 9α-hydroxymedioresinol and related lignans from Allamanda neriifolia. Phytochemistry 27:75–77

    Google Scholar 

  45. Sugiyama M, Kikuchi M (1993) Characterization of lariciresinol glucosides from Osmanthus asiaticus. Heterocycles 36:117–121

    Article  Google Scholar 

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Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima, 770-8505, Japan

    Shin-ichiro Kurimoto, Mamoru Okasaka, Yoshiki Kashiwada & Yoshihisa Takaishi

  2. Institute of Botany and Botanical Garden, F. Khodzhaev, st. 32, 700143, Tashkent, Uzbekistan

    Olimjon K. Kodzhimatov

Authors
  1. Shin-ichiro Kurimoto
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  2. Mamoru Okasaka
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  3. Yoshiki Kashiwada
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  4. Olimjon K. Kodzhimatov
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  5. Yoshihisa Takaishi
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Correspondence to Yoshiki Kashiwada.

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Kurimoto, Si., Okasaka, M., Kashiwada, Y. et al. Four new glucosides from the aerial parts of Mediasia macrophylla . J Nat Med 65, 180–185 (2011). https://doi.org/10.1007/s11418-010-0444-3

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  • DOI: https://doi.org/10.1007/s11418-010-0444-3

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