Unusual sesquiterpene lactones with a new carbon skeleton and new acetylenes from Ajania przewalskii

Food Chemistry

Volumn 118, Issue 2, 2010, Pages 228-238

  Zhu, Ying ^a   Zhang, Li Xia ^a   Zhao, Yan ^a   Huang, Guo Du ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Acetylenes; Ajania prewalskii; Antioxidation; Asteraceae; Cytotoxicity; Eudesmane; Guaianolide

Indexed keywords

1BETA ACETOXYOXYL 2 NOREUDESM 4(15) EN 5ALPHA,6BETA,7ALPHA,11ALPHAH 12,6 OLIDE; 1BETA HYDROXYEUDESM 3 OXO 4BETA,5ALPHA,6BETA,7ALPHA,11ALPHAH 12,6 OLIDE; 1BETA HYDROXYL 2 NOREUDESM 4(15) EN 5ALPHA,6BETA,7ALPHA,11ALPHAH 12,6 OLIDE; 2 HYDROXYL 2 (1ALPHA,2BETA,3 TRIHYDROXYL 3 NONAENE 5,7 DIYNE) 4H PYRAN; 3BETA,4ALPHA HYDROXYL 2 (2',4' HEXADIYNYLIDENE) 1,6 DIOXASPIRO[4,5]DECANE; 4 HYDROXYL 3,5 DIMETHOXYL 6 O BETA DEXTRO GLUCOSEBENZENE; 8ALPHA ANGELOYLOXYL 3ALPHA,4ALPHA DIHYDROXYGUAIA 1,9,11(13) TRIEN 6,12 OLIDE; ACETYLENE DERIVATIVE; CAFFEIC ACID; CAFFEIC ACID METHYL ESTER; CARBON; CHLOROGENIC ACID BUTYL ESTER; GUAIANOLIDE DERIVATIVE; ISOSCOPOLETIN; NOREUDESMANOLIDE DERIVATIVE; SABANDININ; SESQUITERPENE LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

AJANIA PRZEWALSKII; ANTIOXIDANT ACTIVITY; ARTICLE; ASTERACEAE; CANCER CELL CULTURE; CELL STRAIN HEPG2; CELL STRAIN K 562; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; IC 50; STRUCTURE ANALYSIS;

AJANIA; ASTERACEAE;

EID: 69049089724     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2009.04.112     Document Type: Article

References (33)

1. Adekenov S.M., Kulyjasov A.T., Raldugin V.A., Bagryanskaya I.Y., Gatilov Y.V., and Shakirov M.M. Ajanolide A, a new germacranolide from Ajania fruticulosa. Russian Chemical Bulletin 47 1 (1998) 169-172
2. Ahmed A.A., Gáti T., Hussein T.A., Ali A.T., Tzakou O.A., Couladis M.A., et al. Ligustolide A and B, two novel sesquiterpenes with rare skeletons and three 1,10-seco-guaianolide derivatives from Achillea ligustica. Tetrahedron 59 21 (2003) 3729-3735
3. Barla A., Topçu G., Öksüz S., Tümen G., and Kingston D. Identification of cytotoxic sesquiterpenes from Laurus nobilis L. Food Chemistry 104 4 (2007) 1478-1484
4. Belenovskaya L.M., and Markova L.P. Phenol compounds of Ajania achilleoids. Khiiya Prirodnykh Soedinenii 2 (1979) 232-233
5. Birnecker W., Wallnöfer B., Hofer O., and Greger H. Relative and absolute configurations of two naturally occurring acetylenic spiroketal enol ether epoxides. Tetrahedron 44 1 (1988) 267-276
6. Bolzani V.d.S., Trevisan L.M.V., and Young M.C.M. Caffeic acid esters and triterpenes of Alibertia macrophylla. Phytochemistry 30 6 (1991) 2089-2091
7. Chumbalov T.K., Glyzin V.I., and Zhubaeva R.A. Flavonoids of Ajania fastigiata. Khimiya Prirodnykh Soedinenii 6 (1974) 791-792
8. Cui C.B., Yezuka Y., Kikuchi K., Nakano H., Tamaoki T., and Park J.H. Constituents of a fern, Davallia mariesii Moore. I. Isolation and structures of davallialactone and a new flavanone glucuronide. Chemical and Pharmaceutical Bulletin 38 12 (1990) 3218-3225
9. De Rosa S., Mitova M., Handjieva N., and Calis I. Coumarin glucosides from Cruciata taurica. Phytochemistry 59 4 (2002) 447-450
10. Debenedetti S.L., Nadinic E.L., Coussio J.D., De Kimpe N., and Boeykens M. Two 6,7-dioxygenated coumarins from Pterocaulon virgatum. Phytochemistry 48 4 (1998) 707-710
11. Editorial Committee for Flora of the Chinese Academy of Science (1983). In Y. Ling, C. Shih (Eds.), Flora of China. Science Press, Beijing, 76(1), 105-125.
12. Gomes C.A., da Cruz T.G., Andrade J.L., Milhazes N., Borges F., and Marques M.P.M. Anticancer activity of phenolic acids of natural or synthetic origin: A structure-activity study. Journal of Medicinal Chemistry 46 25 (2003) 5395-5401
13. Gomes Jr. M., and Antunes O.A.C. Upjohn catalytic osmium tetroxide oxidation process: diastereoselective dihydroxylation of monoterpenes. Catalysis Communications 2 6-7 (2001) 225-227
14. Hussain R.F., Nouri A.M.E., and Oliver R.T.D. A new approach for measurement of cytotoxicity using colorimetric assay. Journal of Immunological Methods 160 1 (1993) 89-96
15. Jequier C., Nicollier G., Tabacchi R., and Garnero J. Constituents of the essential oil of Salvia stenophylla. Phytochemistry 19 3 (1980) 461-462
16. Kuroyanagi M., Shiotsu M., Ebihara T., Kawai H., Ueno A., and Fukushima S. Chemical studies on Viburnum awabuki K. Koch. Chemical and Pharmaceutical Bulletin 34 10 (1986) 4012-4017
17. Kampa M., Alexaki V.I., Notes G., Nifli A.P., Nistikaki A., Hatzoglou A., et al. Antiproliferative and apoptotic effects of selective phenolic acids on T47D human breast cancer cells: Potential mechanism of action. Breast Cancer Research 6 (2004) 63-74
18. Li H., Meng J.-C., Cheng C.-H.-K., Higa T., Tanaka J., and Tan R.-X. New guaianolides and xanthine oxidase inhibitory flavonols from Ajania fruticulosa. Journal of Natural Products 62 7 (1999) 1053-1055
19. Marco J.A. Sesquiterpene lactones from Artemisia herba-alba subsp. Herba-alba. Phytochemistry 28 11 (1989) 3121-3126
20. Matsuo A., Uchio Y., Nakayama M., and Hayashi S. Two new acetylenic compounds from Chrysanthemum boreale. Tetrahedron Letters 22 (1974) 1885-1888
21. Meng J.-C., Hu Y.-F., Chen J.-H., and Tan R.-X. Antifungal highly oxygenated guaianolides and other constituents from Ajania fruticulosa. Phytochemistry 58 7 (2001) 1141-1145
22. Re R., Pellegrini N., Proteggente A., Pannala A., Yang M., and Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine 26 9-10 (1999) 1231-1237
23. Rumbero-Sanchez A., and Vazquez P. Quinic acid esters from Isertia haenkana. Phytochemistry 30 1 (1991) 311-313
24. Sarker S.D., Gray A.I., Waterman P.G., and Armstrong J.A. Coumarins from Asterolasia trymalioides. Journal of Natural Products 57 11 (1994) 1549-1551
25. Tan R.-X., Jia Z.-J., Zhao Y., and Feng S.-L. Sesquiterpenes and acetylenes from Artemisia feddei. Phytochemistry 31 9 (1992) 3135-3138
26. Tsukamoto H., Hisada S., Nishibe S., Roux D.G., and Rourke J.P. Coumarins from Olea africana and Olea capensis. Phytochemistry 23 3 (1984) 699-711
27. Tsukamoto H., Hisada S., and Nishibe S. Coumarins from bark of Fraxinus japonica and F. mandshurica var. japonica. Chemical and Pharmaceutical Bulletin 33 9 (1985) 4069-4073
28. Van den Berg R., Haenen G.R.M.M., Van den Berg H., and Bast A. Applicability of an improved Trolox equivalent antioxidant capacity (TEAC) assay for evaluation of antioxidant capacity measurements of mixtures. Food Chemistry 66 4 (1999) 511-517
29. Von Gadow A., Joubert E., and Hansmann C.F. Comparison of the antioxidant activity of aspalathin with that of other plant phenols of rooibos tea (Aspalathus linearis), α-Tocopherol, BHT, and BHA. Journal of Agricultural and Food Chemistry 45 3 (1997) 632-638
30. Wu Q.-X., Shi Y.-P., and Jia Z.-J. Eudesmane sesquiterpenoids from the Asteraceae family. Natural Product Reports 23 5 (2006) 699-734
31. Yusupov M.I., Kasimov S.Z., and Abdullaev N.D. Rupicolin B oxide and isochrysartemin B-new guaianolides from Ajania fastigiata. Khimiya Prirodnykh Soedinenii 2 (1982) 260-261
32. Zdero C., Bohlmann F., and Huneck S. Guaianolides and glaucolides from Ajania achilleoides. Phytochemistry 29 2 (1990) 1585-1588
33. Zhang L.-X., He Z.-W., and Zhu Y. The lipophilic constituents from Ajania prewalskii. Journal of Lanzhou University (Natural Sciences) 42 6 (2006) 1-4