Polycyclic polyprenylated acylphloroglucinols

被引:510
作者
Ciochina, Roxana [1 ]
Grossman, Robert B. [1 ]
机构
[1] Univ Kentucky, Dept Chem, Lexington, KY 40506 USA
关键词
D O I
10.1021/cr0500582
中图分类号
O6 [化学];
学科分类号
0703 [化学];
摘要
The plant family Guttiferae comprises a large number of widely distributed species. The antidepressant activity of one such species Hypericum perforatum has generated interest in the metabolites from this family. Over 100 biologically active polycyclic polyprenylated acylphloroglucinols (PPAPs) in either or both enantiomeric forms have been isolated from Guttiferae plants in the past few decades. These compounds share highly oxygenated and densely substituted bicyclo[3.3.1]nonane-2,4,6-trione core adorned with prenyl or geranyl side chains. This review covers the structure and chemical synthesis of PPAPs. Topics discussed include the biological activity of PPAPs, biosynthesis of PPAPs and synthetic efforts toward PPAPs.
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收藏
页码:3963 / 3986
页数:24
相关论文
共 123 条
[1]
Biosynthesis of hyperforin in Hypericum perforatum [J].
Adam, P ;
Arigoni, D ;
Bacher, A ;
Eisenreich, W .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (21) :4786-4793
[2]
Alves TMD, 1999, J NAT PROD, V62, P369, DOI 10.1021/np9803833
[3]
Bioactive benzophenones from Garcinia xanthochymus fruits [J].
Baggett, S ;
Protiva, P ;
Mazzola, EP ;
Yang, H ;
Ressler, ET ;
Basile, MJ ;
Weinstein, IB ;
Kennelly, EJ .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (03) :354-360
[4]
Polyisoprenylated benzophenone, garcinol, a natural histone acetyltransferase inhibitor, represses chromatin transcription and alters global gene expression [J].
Balasubramanyam, K ;
Altaf, M ;
Varier, RA ;
Swaminathan, V ;
Ravindran, A ;
Sadhale, PP ;
Kundu, TK .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (32) :33716-33726
[5]
Bankova VS, 2000, APIDOLOGIE, V31, P3, DOI 10.1051/apido:2000102
[6]
St John's wort (Hypericum perforatum L.):: a review of its chemistry, pharmacology and clinical properties [J].
Barnes, J ;
Anderson, LA ;
Phillipson, JD .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 2001, 53 (05) :583-600
[7]
Laxifloranone, a new phloroglucinol derivative from Marila laxiflora [J].
Bokesch, HR ;
Groweiss, A ;
McKee, TC ;
Boyd, MR .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (08) :1197-1199
[8]
The first prenylation step in hyperforin biosynthesis [J].
Boubakir, Z ;
Beuerle, T ;
Liu, B ;
Beerhues, L .
PHYTOCHEMISTRY, 2005, 66 (01) :51-57
[9]
THE ABSOLUTE-CONFIGURATION OF HYPERFORIN, AN ANTIBIOTIC FROM HYPERICUM-PERFORATUM-L, BASED ON THE CRYSTAL-STRUCTURE DETERMINATION OF ITS PARA-BROMOBENZOATE ESTER [J].
BRONDZ, I ;
GREIBROKK, T ;
GROTH, P ;
AASEN, AJ .
ACTA CHEMICA SCANDINAVICA SERIES A-PHYSICAL AND INORGANIC CHEMISTRY, 1983, 37 (03) :263-265
[10]
Butkus E, 2001, SYNLETT, P1827