Taxonomic Insights and Its Type Cyclization Correlation of Volatile Sesquiterpenes in Vitex Species and Potential Source Insecticidal Compounds: A Review

被引:17
作者
Barreto, Ighor C. [1 ,2 ]
de Almeida, Anderson S. [2 ]
Sena Filho, Jose G. [3 ]
机构
[1] Univ Fed Bahia, Coordenacao Meio Ambiente, Av Adhemar Barros, BR-40170110 Salvador, BA, Brazil
[2] Univ Fed Sergipe, Programa Posgrad Ciencias Farmaceut, Av Marechal Rondon, BR-49100000 Sao Cristovao, SE, Brazil
[3] Empresa Brasileira Pesquisa Agr EMBRAPA Coastal T, Av Beira Mar 3250, BR-49025040 Aracaju, SE, Brazil
关键词
Vitex; biosynthesis; sesquiterpenes synthases; cyclization; AGNUS-CASTUS L; ESSENTIAL OIL COMPOSITION; BIOLOGICAL-CONTROL AGENT; DELTA-GUAIENE SYNTHASE; E-BETA-FARNESENE; CHEMICAL-COMPOSITION; FUNCTIONAL-CHARACTERIZATION; (E)-BETA-CARYOPHYLLENE SYNTHASE; (+)-DELTA-CADINENE SYNTHASE; (E)-BETA-FARNESENE SYNTHASE;
D O I
10.3390/molecules26216405
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
070307 [化学生物学]; 071010 [生物化学与分子生物学];
摘要
Sesquiterpenes (SS) are secondary metabolites formed by the bonding of 3 isoprene (C5) units. They play an important role in the defense and signaling of plants to adapt to the environment, face stress, and communicate with the outside world, and their evolutionary history is closely related to their physiological functions. This review considers their presence and extensively summarizes the 156 sesquiterpenes identified in Vitex taxa, emphasizing those with higher concentrations and frequency among species and correlating with the insecticidal activities and defensive responses reported in the literature. In addition, we classify the SS based on their chemical structures and addresses cyclization in biosynthetic origin. Most relevant sesquiterpenes of the Vitex genus are derived from the germacredienyl cation mainly via bicyclogermacrene and germacrene C, giving rise to aromadrendanes, a skeleton with the highest number of representative compounds in this genus, and 6,9-guaiadiene, respectively, indicating the production of 1.10-cyclizing sesquiterpene synthases. These enzymes can play an important role in the chemosystematics of the genus from their corresponding routes and cyclizations, constituting a new approach to chemotaxonomy. In conclusion, this review is a compilation of detailed information on the profile of sesquiterpene in the Vitex genus and, thus, points to new unexplored horizons for future research.
引用
收藏
页数:29
相关论文
共 206 条
[41]
Cincotta F., 2015, Chromatography, V2, P410, DOI DOI 10.3390/CHROMATOGRAPHY2030410
[42]
Isolation and bacterial expression of a sesquiterpene synthase cDNA clone from peppermint (Mentha x piperita, L.) that produces the aphid alarm pheromone (E)-beta-farnesene [J].
Crock, J ;
Wildung, M ;
Croteau, R .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (24) :12833-12838
[43]
Terpene synthases of oregano (Origanum vulgare L.) and their roles in the pathway and regulation of terpene biosynthesis [J].
Crocoll, Christoph ;
Asbach, Julia ;
Novak, Johannes ;
Gershenzon, Jonathan ;
Degenhardt, Joerg .
PLANT MOLECULAR BIOLOGY, 2010, 73 (06) :587-603
[44]
E-β-farnesene synergizes the influence of an insecticide to improve control of cabbage aphids in China [J].
Cui, Liang-Liang ;
Dong, Jie ;
Francis, Frederic ;
Liu, Ying-Jie ;
Heuskin, Stephanie ;
Lognay, Georges ;
Chen, Ju-Lian ;
Bragard, Claude ;
Tooker, John F. ;
Liu, Yong .
CROP PROTECTION, 2012, 35 :91-96
[45]
Sesquiterpene lactone-based classification of three Asteraceae tribes: a study based on self-organizing neural networks applied to chemo systematics [J].
Da Costa, FB ;
Terfloth, L ;
Gasteiger, J .
PHYTOCHEMISTRY, 2005, 66 (03) :345-353
[46]
Study on essential oils from the leaves of two Vietnamese plants: Jasminum subtriplinerve CL Blume and Vitex quinata (Lour) FN Williams [J].
Dai, Do N. ;
Thang, Tran D. ;
Ogunwande, Isiaka A. ;
Lawal, Oladipupo A. .
NATURAL PRODUCT RESEARCH, 2016, 30 (07) :860-864
[47]
Purification of (+)-delta-cadinene synthase, a sesquiterpene cyclase from bacteria-inoculated cotton foliar tissue [J].
Davis, EM ;
Tsuji, J ;
Davis, GD ;
Pierce, ML ;
Essenberg, M .
PHYTOCHEMISTRY, 1996, 41 (04) :1047-1055
[48]
Davis EM, 2000, TOP CURR CHEM, V209, P53
[49]
Composition and antioxidant capacity of the essential oil of leaves of Vitex megapotamica (Sprengel) Moldenke [J].
de Brum, Thiele Faccim ;
Boligon, Aline Augusti ;
Frohlich, Janaina Kieling ;
Schwanz, Thiago Guilherme ;
Zadra, Marina ;
Piana, Mariana ;
Forbrig Froeder, Amanda Luana ;
Athayde, Margareth Linde .
NATURAL PRODUCT RESEARCH, 2013, 27 (08) :767-770
[50]
(+)-Germacrene A biosynthesis -: The committed step in the biosynthesis of bitter sesquiterpene lactones in chicory [J].
de Kraker, JW ;
Franssen, MCR ;
de Groot, A ;
König, WA ;
Bouwmeester, HJ .
PLANT PHYSIOLOGY, 1998, 117 (04) :1381-1392