A C14-polyacetylenic glucoside with an α-pyrone moiety and four C10-polyacetylenic glucosides from Mediasia macrophylla

Phytochemistry

Volumn 71, Issue 5-6, 2010, Pages 688-692

  Kurimoto, Shin ichiro ^a   Okasaka, Mamoru ^a   Kashiwada, Yoshiki ^a   Kodzhimatov, Olimjon K ^b   Takaishi, Yoshihisa ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b Academy of Sciences of the Republic of Uzbekistan   (Uzbekistan)

Author keywords

Pyrone; Mediasia macrophylla; Polyacetylene; Umbelliferae

Indexed keywords

APIACEAE; MEDIASIA MACROPHYLLA;

ALKYNE; GLUCOSIDE; PLANT EXTRACT; PYRONE DERIVATIVE;

APIALES; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; PLANT;

ALKYNES; APIACEAE; GLUCOSIDES; MOLECULAR STRUCTURE; PLANT COMPONENTS, AERIAL; PLANT EXTRACTS; PYRONES;

EID: 77949820632     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2009.12.007     Document Type: Article

References (35)

1. Baser K.H.C., Ozek T., Nuriddinov K.R., Nigmatullaev A.M., Khadzimatov K.K., and Aripov K.N. Essential oils of Mediasia macrophylla (Regel et Schmalh.) Pimen. and Foeniculum vulgare Mill. from Uzbekistan. Journal of Essential Oil Research 9 (1997) 249-250
2. Chang S.L., Chang C.L., Chiang Y.M., Hsieh R.H., Tzeng C.R., Wu T.K., Sytwu H.K., Shyur L.F., and Yang W.C. Polyacetylenic compounds and butanol fraction from Bidens pilosa can modulate the differentiation of helper T cells and prevent autoimmune diabetes in non-obese diabetic mice. Planta Medica 70 (2004) 1045-1051
3. Chang C.L., Kuo H.K., Chang S.L., Chiang Y.M., Lee T.H., Wu W.M., Shyur L.F., and Yang W.C. The distinct effects of a butanol fraction of Bidens pilosa plant extract on the development of Th1-mediated diabetes and Th2-mediated airway inflammation in mice. Journal of Biomedical Science 12 (2005) 79-89
4. Chen B., Kawazoe K., Takaishi Y., Honda G., Itoh M., Takeda Y., Kodzhimatov O.K., and Ashurmetov O. Prenylated benzoic acid derivatives from Ferula kuhistanica. Journal of Natural Products 63 (2000) 362-365
5. Chernenko T.V., and Glushenkova A.I. Unsaponified compounds and unsaturated fatty acids of lipids from Mediasia macrophylla leaves. Chemistry of Natural Compounds 39 (2003) 158-160
6. Chernenko T.V., Glushenkova A.I., and Nigmatullaev A.M. Lipids from Mediasia macrophylla leaves. Chemistry of Natural Compounds 38 (2002) 307-309
7. Chiang Y.M., Chang C.L., Chang S.L., Yang W.C., and Shyur L.F. Cytopiloyne, a novel polyacetylenic glucoside from Bidens pilosa, functions as a T helper cell modulator. Journal of Ethnopharmacology 110 (2007) 532-538
8. Christensen L.P., and Brand K. Bioactive polyacetylenes in food plants of the Apiaceae family: occurrence, bioactivity and analysis. Journal of Pharmaceutical and Biomedical Analysis 41 (2006) 683-693
9. Duan H., Takaishi Y., Tori M., Takaoka S., Honda G., Ito M., Takeda Y., Kodzhimatov O.K., Kodzhimatov K., and Ashurmetov O. Polysulfide derivatives from Ferula foetida. Journal of Natural Products 65 (2002) 1667-1669
10. Fu B., Su B.N., Takaishi Y., Honda G., Ito M., Takeda Y., Kodzhimatov O.K., and Ashurmetov O. A bis-sesquiterpene and sesquiterpenolides from Inula macrophylla. Phytochemistry 58 (2001) 1121-1128
11. Ishimaru K., Osabe M., Yan L., Fujioka T., Mihashi K., and Tanaka N. Polyacetylene glycosides from Pratia nummularia cultures. Phytochemistry 62 (2003) 643-646
12. Kamilov K.M., and Nikonov G.K. Chemistry study of Athamanta macrophylla fruits. Prir. Soedin. 5 (1971) 663-664
13. Kitajima J., Kamoshita A., Ishikawa T., Takano A., Fukuda T., Isoda S., and Ida Y. Glycosides of Atractylodes lancea. Chemical & Pharmaceutical Bulletin 51 (2003) 673-678
14. Li S., Kuang H.X., Okada Y., and Okuyama T. New acetylenic glucosides from Bidens bipinnata LINNE. Chemical & Pharmaceutical Bulletin 52 (2004) 439-440
15. Matsuhisa M., Shikishima Y., Takaishi Y., Honda G., Ito M., Takeda Y., Shibata H., Higuti T., Kodzhimatov O.K., and Ashurmetov O. Benzoylphloroglucinol derivatives from Hypericum scabrum. Journal of Natural Products 65 (2002) 290-294
16. Okasaka M., Takaishi Y., Kogure K., Fukuzawa K., Shibata H., Higuti T., Honda G., Ito M., Kodzhimatov O.K., and Ashurmetov O. New stilbene derivatives from Calligonum leucocladum. Journal of Natural Products 67 (2004) 1044-1046
17. Okasaka M., Takaishi Y., Kashiwada Y., Kodzhimatov O.K., Ashurmetov O., Lin A.J., Consentino L.M., and Lee K.H. Terpenoids from Juniperus polycarpus var. seravschanica. Phytochemistry 67 (2006) 2635-2640
18. Okasaka M., Kashiwada Y., Kodzhimatov O.K., Ashurmetov O., and Takaishi Y. Monoterpene glycosides from Paeonia hybrida. Phytochemistry 69 (2008) 1767-1772
19. Park J.Y., Min B.S., Jung H.J., Kim Y.H., Lee H.K., and Bae K.H. Polyacetylene glycosides from Gymnaster koraiensis. Chemical & Pharmaceutical Bulletin 50 (2002) 685-687
20. Shikishima Y., Takaishi Y., Honda G., Ito M., Takeda Y., Tori M., Takaoka S., Kodzhimatov O.K., and Ashurmetov O. Sesquiterpenes from Ferula penninervis. Journal of Natural Products 65 (2002) 1897-1903
21. Su B.N., Takaishi Y., Tori M., Takaoka S., Honda G., Itoh M., Takeda Y., Kodzhimatov O.K., and Ashurmetov O. Macrophyllidimers A and B, two novel sesquiterpene dimers from the bark of Inula macrophylla. Tetrahedron Letters 41 (2000) 1475-1479
22. Su B.N., Takaishi Y., Honda G., Itoh M., Takeda Y., Kodzhimatov O.K., and Ashurmetov O. Sesquiterpene phenylpropanoid and sesquiterpene chromone derivatives from Ferula pallida. Journal of Natural Products 63 (2000) 520-522
23. Su B.N., Takaishi Y., Tori M., Takaoka S., Honda G., Itoh M., Takeda Y., Kodzhimatov O.K., Ashurmetov O., and Macrophyllols A. A and B, two unusual novel sesquiterpene and monoterpene dimers from the bark of Inula macrophylla. Organic Letters 2 (2000) 493-496
24. Su B.N., Takaishi Y., Honda G., Itoh M., Takeda Y., Kodzhimatov O.K., and Ashurmetov O. Sesquiterpene coumarins and related derivatives from Ferula pallida. Journal of Natural Products 63 (2000) 436-440
25. Su B.N., Takaishi Y., Yabuuchi T., Kusumi T., Tori M., Takaoka S., Honda G., Itoh M., Takeda Y., Kodzhimatov O.K., and Ashurmetov O. Sesquiterpenes and monoterpenes from the bark of Inula macrophylla. Journal of Natural Products 64 (2001) 466-471
26. Suzuki K., Okasaka M., Kashiwada Y., Takaishi Y., Honda G., Ito M., Takeda Y., Kodzhimatov O.K., Ashurmetov O., Sekiya M., and Ikeshiro Y. Sesquiterpene lactones from the roots of Ferula varia and their cytotoxic activity. Journal of Natural Products 70 (2007) 1915-1918
27. Tada Y., Shikishima Y., Takaishi Y., Shibata H., Higuti T., Honda G., Ito M., Takeda Y., Kodzhimatov O.K., Ashurmetov O., and Ohmoto Y. Coumarins and g -pyrone derivatives from Prangos pabularia: antibacterial activity and inhibition of cytokine release. Phytochemistry 59 (2002) 649-654
28. Tamemoto K., Takaishi Y., Chen B., Kawazoe K., Shibata H., Higuti T., Honda G., Ito M., Takeda Y., Kodzhimatov O.K., and Ashurmetov O. Sesquiterpenoids from the fruits of Ferula kuhistanica and antibacterial activity of the constituents of F. kuhistanica. Phytochemistry 58 (2001) 763-767
29. Tamemoto K., Takaishi Y., Kawazoe K., Honda G., Ito M., Kiuchi F., Takeda Y., Kodzhimatov O.K., Ashurmetov O., Shimizu K., Nagasawa H., Uto Y., and Hori H. An unusual sesquiterpene derivative from Ferula kuhistanica. Journal of Natural Products 65 (2002) 1323-1324
30. Tanaka N., Takaishi Y., Shikishima Y., Nakanishi Y., Bastow K., Lee K.H., Honda G., Ito M., Takeda Y., Kodzhimatov O.K., and Ashurmetov O. Prenylated benzophenones and xanthones from Hypericum scabrum. Journal of Natural Products 67 (2004) 1870-1875
31. Ubillas R.P., Mendez C.D., Jolad S.D., Luo J., King S.R., Carlson T.J., and Fort D.M. Antihyperglycemic acetylenic glucosides from Bidens pilosa. Planta Medica 66 (2000) 82-83
32. Wang N., Yao X., Ishii R., and Kitanaka S. Antiallergic agents from natural sources. 3. Structures and inhibitory effects on nitric oxide production and histamine release of five novel polyacetylene glucosides from Bidens parviflora Willd. Chemical & Pharmaceutical Bulletin 49 (2001) 938-942
33. Yamanaka M., Ishibashi K., Shimomura K., and Ishimaru K. Polyacetylene glucosides in hairy root culture of Lobelia cardinalis. Phytochemistry 41 (1996) 183-185
34. Zhou P., Takaishi Y., Duan H., Chen B., Itoh M., Takeda Y., Kodzhimatov O.K., and Lee K.H. Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release. Phytochemistry 53 (2000) 689-697
35. Zhou Y.Z., Ma H.Y., Chen H., Qia L., Yao Y., Cao J.Q., and Pei Y.H. New acetylenic glucosides from Carthamus tinctoriu. Chemical & Pharmaceutical Bulletin 54 (2006) 1455-1456