Cancer chemopreventive diterpenes from Salvia corrugata

被引:25
作者
Giacomelli, Emanuela [1 ]
Bertrand, Samuel [2 ]
Nievergelt, Andreas [2 ]
Zwick, Vincent [2 ]
Simoes-Pires, Claudia [2 ]
Marcourt, Laurence [2 ]
Rivara-Minten, Elisabeth [2 ]
Cuendet, Muriel [2 ]
Bisio, Angela [1 ]
Wolfender, Jean-Luc [2 ]
机构
[1] Univ Genoa, Dept Pharm, I-16147 Genoa, Italy
[2] Univ Geneva, Sch Pharmaceut Sci, CH-1211 Geneva 4, Switzerland
关键词
Salvia corrugata; Diterpenes; Abietane; Icetexane; Fruticulin C; Quinone reductase; Histone deacetylase; REDUCTASE-INDUCING ACTIVITY; MORINDA-CITRIFOLIA NONI; QUINONE REDUCTASE; ABIETANE DITERPENOIDS; ICETEXANE DITERPENOIDS; DEMETHYL FRUTICULIN; INDUCTION; CHROMATOGRAPHY; CONSTITUENTS; GILLIESSI;
D O I
10.1016/j.phytochem.2013.09.011
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
NMR and NP-HPLC-UV profiling of the exudate of Salvia corrugata revealed that its secondary metabolite composition was largely dominated by alpha-hydroxy-beta-isopropyl-benzoquinone diterpenoids. Among them, four diterpenes not described previously were isolated and identified as fruticulin C (3), 7 alpha-methoxy-19-acetoxy-royleanone (4), 7 alpha,19-diacetoxy-royleanone (5), and 7-dehydroxy-conacytone (7). In addition, the known diterpenes fruticulin A (1), demethyl-fruticulin A (2) and 7 alpha-O-methyl-conacytone (6) were also obtained. The isolated compounds were evaluated for their cancer chemopreventive activity by measuring quinone reductase induction activity and histone deacetylase inhibition. Three compounds (1, 2 and 5) showed promising activity. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:257 / 264
页数:8
相关论文
共 48 条
  • [1] Acylated pregnane glycosides from Caralluma sinaica
    Al-Massarani, Shaza M.
    Bertrand, Samuel
    Nievergelt, Andreas
    El-Shafae, Azza M.
    Al-Howiriny, Tawfeq A.
    Al-Musayeib, Nawal M.
    Cuendet, Muriel
    Wolfender, Jean-Luc
    [J]. PHYTOCHEMISTRY, 2012, 79 : 129 - 140
  • [2] The Role of HDAC6 in Cancer
    Aldana-Masangkay, Grace I.
    Sakamoto, Kathleen M.
    [J]. JOURNAL OF BIOMEDICINE AND BIOTECHNOLOGY, 2011,
  • [3] Two-step mechanism of induction of the gene expression of a prototypic cancer-protective enzyme by diphenols
    Bensasson, Rene V.
    Zoete, Vincent
    Dinkova-Kostova, Albena T.
    Talalay, Paul
    [J]. CHEMICAL RESEARCH IN TOXICOLOGY, 2008, 21 (04) : 805 - 812
  • [4] Alkane effect in the Arizona liquid systems used in countercurrent chromatography
    Berthod, A
    Hassoun, M
    Ruiz-Angel, MJ
    [J]. ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 2005, 383 (02) : 327 - 340
  • [5] Antimicrobial Activity of the Ornamental Species Salvia corrugata, a Potential New Crop for Extractive Purposes
    Bisio, Angela
    Romussi, Giovanni
    Russo, Eleonora
    Cafaggi, Sergio
    Schito, Anna Maria
    Repetto, Barbara
    De Tommasi, Nunziatina
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (22) : 10468 - 10472
  • [6] ABIETANE AND ICETEXANE DITERPENOIDS FROM SALVIA CANDICANS
    CARDENAS, J
    RODRIGUEZHAHN, L
    [J]. PHYTOCHEMISTRY, 1995, 38 (01) : 199 - 204
  • [7] Anthraquinones with quinone reductase-inducing activity and Benzophenones from Morinda citrifolia (Noni) roots
    Deng, Ye
    Chin, Young-Won
    Chai, Heebyung
    Keller, William J.
    Kinghorn, A. Douglas
    [J]. JOURNAL OF NATURAL PRODUCTS, 2007, 70 (12): : 2049 - 2052
  • [8] Abietane Diterpenoids from Salvia sahendica - Antiprotozoal Activity and Determination of Their Absolute Configurations
    Ebrahimi, Samad N.
    Zimmermann, Stefanie
    Zaugg, Janine
    Smiesko, Martin
    Brun, Reto
    Hamburger, Matthias
    [J]. PLANTA MEDICA, 2013, 79 (02) : 150 - 156
  • [9] Lanigerol: A new antimicrobial icetexane diterpene from Salvia lanigera
    ElLakany, AM
    Abdelkader, MS
    Sabri, NN
    Stermitz, FR
    [J]. PLANTA MEDICA, 1995, 61 (06) : 559 - 560
  • [10] Epling C, 1939, Repertorium Specierum Novarum Regni Vegetabilis