Chemical structures, biosynthesis, bioactivities, biocatalysis and semisynthesis of tobacco cembranoids: An overview

被引:39
作者
Yan, Ning [1 ]
Du, Yongmei [1 ]
Liu, Xinmin [1 ]
Zhang, Hongbo [1 ]
Liu, Yanhua [1 ]
Zhang, Peng [1 ]
Gong, Daping [1 ]
Zhang, Zhongfeng [1 ]
机构
[1] Chinese Acad Agr Sci, Tobacco Res Inst, Qingdao 266101, Peoples R China
关键词
Tobacco cembranoids; Chemical structures; Biosynthesis; Bioactivities; Biocatalysis; Semisynthesis; CELL-FREE-EXTRACTS; ACUTE HIPPOCAMPAL SLICES; LEAF SURFACE CHEMICALS; CHEMISTRY; TRICHOMES; BIOTRANSFORMATIONS; NEUROTOXICITY; GENE; CEMBRATRIENE-4,6-DIOL; CEMBRATRIENETRIOLS;
D O I
10.1016/j.indcrop.2015.12.031
中图分类号
S2 [农业工程];
学科分类号
0828 ;
摘要
Cembranoids, 14-membered carbocyclic diterpenes composed of four isoprene units, are mainly found in plants of the Nicotiana and Pinus genera, as well as in soft coral and other marine organisms. We summarise the chemical structures of the eighty-seven naturally occurring tobacco cembranoids (1-52), nor-cembranoids (53-74), seco-cembranoids (75-82) and cyclised cembranoids (83-87) reported to date. The most prevalent cembranoids in tobacco are (1S,2E,4S,7E,11E)-cembra-2,7,11-triene-4,6-diol (1) and (1S,2E,412,7E,11E)-cembra-2,7,11-triene-4,6-diol (2), which are biosynthesised in the plastid from the reactions of geranylgeranyl diphosphate with cembrantrien-ol synthase and cytochrome P450 hydroxylase via the 2-C-methyl-D-erythritol-4-phosphate metabolic pathway. The accumulation of cembranoids in tobacco is affected by genetic and environmental factors, including fertiliser, water and light exposure, soil-type and temperature. Tobacco-derived cembranoids are known to display antifungal, antibacterial, anti-human immunodeficiency virus, anti-tumour and neuroprotective properties. A large number of biologically active (primarily anti-invasive, anti-prolifeiative, anti-migratory and neuroprotective) compounds have been prepared from the semisynthesis of tobacco cembranoids, many via biocatalytic methods. The documented bioactivities of tobacco cembranoids make them excellent templates for the future development of drugs to treat cancer, AIDS, Alzheimer's disease, Parkinson's disease, stroke and other neurodegenerative diseases. These findings indicated that although tobacco has long been associated with negative effects on human health, it may ultimately be able to play a therapeutic role. (c) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:66 / 80
页数:15
相关论文
共 92 条
[1]   Antimicrobial, antioxidant, and antimutagenic activities of selected marine natural products and tobacco cembranoids [J].
Aqil, Farrukh ;
Zahin, Maryam ;
El Sayed, Khalid A. ;
Ahmad, Iqbal ;
Orabi, Khaled Y. ;
Arif, Jamal M. .
DRUG AND CHEMICAL TOXICOLOGY, 2011, 34 (02) :167-179
[2]   TOBACCO CHEMISTRY .76. BIOTRANSFORMATIONS OF TOBACCO ISOPRENOIDS USING PLANT-CELL CULTURES OF TRIPTERYGIUM-WILFORDII [J].
ARNARP, J ;
CHU, WLA ;
ENZELL, CR ;
HEWITT, GM ;
KUTNEY, JP ;
LI, K ;
MILANOVA, RK ;
NAKATA, H ;
NASIRI, A ;
OKADA, Y .
ACTA CHEMICA SCANDINAVICA, 1993, 47 (07) :683-688
[3]   TOBACCO CHEMISTRY .77. BIOTRANSFORMATIONS OF A MAJOR TOBACCO CEMBRATRIENEDIOL USING PLANT-CELL CULTURES OF NICOTIANA-SYLVESTRIS [J].
ARNARP, J ;
CHU, WLA ;
ENZELL, CR ;
HEWITT, GM ;
KUTNEY, JP ;
LI, K ;
MILANOVA, RK ;
NAKATA, H ;
NASIRI, A ;
TSUDA, T .
ACTA CHEMICA SCANDINAVICA, 1993, 47 (07) :689-694
[4]   Bioactive Natural, Biocatalytic, and Semisynthetic Tobacco Cembranoids [J].
Baraka, Hany N. ;
Khanfar, Mohammad A. ;
Williams, John C. ;
El-Giar, Emad M. ;
El Sayed, Khalid A. .
PLANTA MEDICA, 2011, 77 (05) :467-476
[5]   TOBACCO CHEMISTRY .51. NEW CEMBRANIC DITERPENOIDS FROM GREEK TOBACCO [J].
BEHR, D ;
WAHLBERG, I ;
NISHIDA, T ;
ENZELL, CR ;
BERG, JE ;
PILOTTI, AM .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1980, 34 (03) :195-202
[6]   Biotransformation of monoterpenoids and their antimicrobial activities [J].
Bhattia, Haq Nawaz ;
Khan, Saleha Suleman ;
Khan, Ajmal ;
Rani, Mubeen ;
Ahmad, Viqar Uddin ;
Choudhary, Muhammad Iqbal .
PHYTOMEDICINE, 2014, 21 (12) :1597-1626
[7]  
BYLOV AM, 1983, Z NATURFORSCH C, V38, P515
[8]   Molecular-genetic analysis of plant cytochrome P450-dependent monooxygenases [J].
Chapple, C .
ANNUAL REVIEW OF PLANT PHYSIOLOGY AND PLANT MOLECULAR BIOLOGY, 1998, 49 :311-343
[9]  
[程君奇 CHENG Junqi], 2011, [中国烟草学报, Acta Tabacaria Sinica], V17, P18
[10]  
Court W.A., 1984, TOBACCO SCI, V28, P59