Bioactive sesquiterpenes from Santolina rosmarinifolia subsp, Canescens.: A conformational analysis of the germacrane ring

被引:45
作者
Barrero, AF
Herrador, MM
Quilez, JF
Alvarez-Manzaneda, R
Portal, D
Gavin, JA
Gravalos, DG
Simmonds, MSJ
Blaney, WM
机构
[1] Univ Granada, Inst Biotecnol, Fac Ciencias, Dept Quim Organ, E-18071 Granada, Spain
[2] Univ Almeria, Fac Ciencias Expt, Dept Quim Organ, Almeria 04120, Spain
[3] Inst Univ Bioorgan Antonio Gonzalez, Tenerife, Spain
[4] Pharma Mar SA, Madrid 28760, Spain
[5] Royal Bot Gardens, Jodrell Lab, Richmond, Surrey, England
[6] Birkbeck Coll, Dept Biol, London, England
关键词
Santolina rosmarinifolia subsp canescens; compositae; sesquiterpenes; conformational study; biological activities; antifeedants;
D O I
10.1016/S0031-9422(99)00047-3
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The hexane extract of aerial parts of Santolina rosmarinifolia subsp. canescens afforded eight new sesquiterpenes in addition to known compounds. Their structures were determined by spectroscopic methods and chemical transformations. The conformational analysis of the germacrane constituents was carried out by spectroscopic methods, including NMR at varying temperature and by molecular mechanics calculations. The antifeedant, antibacterial and antitumoral activity of selected compounds has been tested. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:529 / 541
页数:13
相关论文
共 28 条
  • [1] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS
    ALLINGER, NL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) : 8127 - 8134
  • [2] CALCULATION OF STRUCTURES OF HYDROCARBONS CONTAINING DELOCALIZED ELECTRONIC SYSTEMS BY MOLECULAR MECHANICS METHOD
    ALLINGER, NL
    SPRAGUE, JT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (12) : 3893 - 3907
  • [3] REMARKABLE DIFFERENCES IN THE REACTIVITY OF ECHINADIOL AND SHIROMODIOL, BIOLOGICALLY-ACTIVE EPIMERIC GERMACRANE DERIVATIVES
    APPENDINO, G
    TETTAMANZI, P
    GARIBOLDI, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (07): : 2139 - 2144
  • [4] BISABOLENE DERIVATIVES AND OTHER CONSTITUENTS FROM ACHILLEA-ODORATA
    BARRERO, AF
    ALVAREZMANZANEDA, EJ
    ALVAREZMANZANEDA, R
    [J]. PHYTOCHEMISTRY, 1990, 29 (10) : 3213 - 3216
  • [5] STEREOCHEMISTRY OF 14-HYDROXY-BETA-CARYOPHYLLENE AND RELATED-COMPOUNDS
    BARRERO, AF
    MOLINA, J
    OLTRA, JE
    ALTAREJOS, J
    BARRAGAN, A
    LARA, A
    SEGURA, M
    [J]. TETRAHEDRON, 1995, 51 (13) : 3813 - 3822
  • [6] GERMACRANOLIDES FROM SANTOLINA-ROSMARINIFOLIA SUBSP CANESCENS
    BARRERO, AF
    SANCHEZ, JF
    ARANA, E
    [J]. PHYTOCHEMISTRY, 1988, 27 (12) : 3969 - 3970
  • [7] ALPHA-LONGIPINENE DERIVATIVES FROM SANTOLINA-VISCOSA - A CONFORMATIONAL-ANALYSIS OF THE CYCLOHEPTANE RING
    BARRERO, AF
    HERRADOR, MM
    MOLINA, JM
    QUILEZ, JF
    QUIROS, M
    [J]. JOURNAL OF NATURAL PRODUCTS, 1994, 57 (07): : 873 - 881
  • [8] Sesquiterpenes from Santolina chamaecyparissus subsp. squarrosa
    Barrero, AF
    Alvarez-Manzaneda, R
    Quilez, JF
    Herrador, MH
    [J]. PHYTOCHEMISTRY, 1998, 48 (05) : 807 - 813
  • [9] ANTINEOPLASTIC AND ANTIHERPETIC ACTIVITY OF SPERMIDINE CATECHOLAMIDE IRON CHELATORS
    BERGERON, RJ
    CAVANAUGH, PF
    KLINE, SJ
    HUGHES, RG
    ELLIOTT, GT
    PORTER, CW
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1984, 121 (03) : 848 - 854
  • [10] POLYACETYLENE COMPOUNDS .152. ACETYLENE COMPOUNDS FROM SANTOLINA CHAMAECYPARISSUS L
    BOHLMANN, F
    ZDERO, C
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (06): : 2062 - &