Occurrence, biological activities and synthesis of kaurane diterpenes and their glycosides

被引:125
作者
Anselmo Garcia, Pablo [1 ]
Braga de Oliveira, Alaide [1 ]
Batista, Ronan [1 ]
机构
[1] Univ Estadual Sudoeste Bahia, Dept Estudios Basicos & Instrumentais, BR-45700000 Itapetinga, BA, Brazil
关键词
kaurane diterpenes; synthesis; kaurane glycosides; biological activities;
D O I
10.3390/12030455
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 [生物化学与分子生物学]; 081704 [应用化学];
摘要
This paper presents a review on kaurane diterpenes and their glycoside derivatives, covering aspects of their occurrence, biological activities and the synthesis of these natural products and their analogues. First, it shows and classifies diterpenes, in accordance with the already established structural criteria in the literature. Then, kaurane diterpenes are presented, focusing on their chemical structures, occurrence in the plant kingdom and their main, recently described, biological activities. Moreover, the most significant works, published between 1964 and November 2006, which describe the total synthesis or structural transformations of some kaurane diterpenes, including either semisynthetic and/or microbiological methodologies, are consisely reviewed. At this point, some general considerations on glycosides are introduced, and kaurane glycosides are presented and discussed on the basis of their toxic importance and occurrence in the plant kingdom, having focused on related aspects of their biological activities and the relationships between these activities and the structural factors of their molecules. Finally, the principal methods of glycosidation by enzymatic and chemical processes are both presented, and a few papers on the synthesis of kaurane glycosides are succinctly discussed.
引用
收藏
页码:455 / 483
页数:29
相关论文
共 168 条
[1]
SESQUITERPENE LACTONES AND KAURANE GLYCOSIDES FROM FRANCOEURIA-CRISPA [J].
ABDELMOGIB, M ;
JAKUPOVIC, J ;
DAWIDAR, AM ;
METWALLY, MA ;
ABOUELZAHAB, M .
PHYTOCHEMISTRY, 1990, 29 (08) :2581-2584
[2]
Cytostatic and cytotoxic activity of synthetic diterpene derivatives obtained from (-)-Kaur-9(11),16-dien-19-oic acid against human cancer cell lines [J].
Alonso, R ;
Gomis, H ;
Taddei, A ;
Sajo, C .
LETTERS IN DRUG DESIGN & DISCOVERY, 2005, 2 (04) :255-259
[3]
A general survey and some taxonomic implications of diterpenes in the Asteraceae [J].
Alvarenga, SAV ;
Ferreira, MJP ;
Rodrigues, GV ;
Emerenciano, VP .
BOTANICAL JOURNAL OF THE LINNEAN SOCIETY, 2005, 147 (03) :291-308
[4]
A DITERPENE FROM MIKANIA-OBTUSATA ACTIVE ON TRYPANOSOMA-CRUZI [J].
ALVES, TMA ;
CHAVES, PPG ;
SANTOS, LMST ;
NAGEM, TJ ;
MURTA, SMF ;
CERAVOLO, IP ;
ROMANHA, AJ ;
ZANI, CL .
PLANTA MEDICA, 1995, 61 (01) :85-87
[5]
Kaurane and pimarane-type diterpenes from the Viguiera species inhibit vascular smooth muscle contractility [J].
Ambrosio, Sergio R. ;
Tirapelli, Carlos R. ;
da Costa, Fernando B. ;
de Oliveira, Ana M. .
LIFE SCIENCES, 2006, 79 (10) :925-933
[6]
[Anonymous], 1995, MONOSACCHARIDES THEI
[7]
Synthesis of 1-O-monoacyl or 12-O-monoacyl, 1-,12-O-diacyl-, and 11,12-dehydrated excisanin A 7,14-acetonides and their cytotoxic activity [J].
Aoyagi, Yutaka ;
Nishioka, Yumi ;
Tobe, Fukuya ;
Hasuda, Tomoyo ;
Takeya, Koichi ;
Gui, Ming-Yu ;
Jin, Yong-Ri ;
Li, Xu-Wen .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (17) :5802-5811
[8]
Toxicity of acetone extract of Sideritis trojana and 7-epicandicandiol, 7-epic andicandiol diacetate and 18-acetylsideroxol against stored pests Acanthoscelides obtectus (Say), Sitophilus granarius (L.) and Ephestia kuehniella (Zell.) [J].
Aslan, I ;
Kiliç, T ;
Gören, AC ;
Topçu, G .
INDUSTRIAL CROPS AND PRODUCTS, 2006, 23 (02) :171-176
[9]
Babu BS, 2000, TETRAHEDRON LETT, V41, P1271
[10]
ENT-KAURANES AND OLEANANES FROM CROTON-LACCIFERUS [J].
BANDARA, BMR ;
WIMALASIRI, WR ;
MACLEOD, JK .
PHYTOCHEMISTRY, 1988, 27 (03) :869-871