Linear Triquinane Sesquiterpenoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

被引:43
作者
Qiu, Yi [1 ]
Lan, Wen-Jian [2 ]
Li, Hou-Jin [1 ]
Chen, Liu-Ping [1 ]
机构
[1] Sun Yat Sen Univ, Sch Chem, Guangzhou 510275, Guangdong, Peoples R China
[2] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
来源
MOLECULES | 2018年 / 23卷 / 09期
基金
中国国家自然科学基金;
关键词
linear triquinane sesquiterpenoid; hirsutane; capnellene; isolation; structure; biological activity; synthesis; NATURALLY-OCCURRING (-)-DELTA-9(12)-CAPNELLENE; STEREOCONTROLLED TOTAL-SYNTHESIS; HIRSUTANE-TYPE SESQUITERPENOIDS; ASYMMETRIC TOTAL-SYNTHESIS; FUNGUS CHONDROSTEREUM SP; SQUARATE ESTER CASCADE; 1ST TOTAL-SYNTHESIS; CYCLOPENTANOID ALLYLSILANES; NATURAL-PRODUCTS; STEREOSELECTIVE-SYNTHESIS;
D O I
10.3390/molecules23092095
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
Linear triquinane sesquiterpenoids represent an important class of natural products. Most of these compounds were isolated from fungi, sponges, and soft corals, and many of them displayed a wide range of biological activities. On account of their structural diversity and complexity, linear triquinane sesquiterpenoids present new challenges for chemical structure identification and total synthesis. 118 linear triquinane sesquiterpenoids were classified into 8 types, named types I-VIII, based on the carbon skeleton and the position of carbon substituents. Their isolation, structure elucidations, biological activities, and chemical synthesis were reviewed. This paper cited 102 articles from 1947 to 2018.
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页数:33
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共 102 条
  • [1] ANTIMICROBIAL METABOLITES FROM LENTINUS-CRINITUS
    ABATE, D
    ABRAHAM, WR
    [J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (11) : 1348 - 1350
  • [2] ANTIFUNGAL SESQUITERPENOIDS FROM AN ARTHROCONIDIAL FUNGUS
    AMOUZOU, E
    AYER, WA
    BROWNE, LM
    [J]. JOURNAL OF NATURAL PRODUCTS, 1989, 52 (05): : 1042 - 1054
  • [3] AN ENANTIOSELECTIVE ROUTE TO (-)-DELTA(9(12))-CAPNELLENE EMPLOYING SILYL GROUP DIRECTED STEREO CONTROL
    ASAOKA, M
    OBUCHI, K
    TAKEI, H
    [J]. TETRAHEDRON, 1994, 50 (03) : 655 - 660
  • [4] Augusto G., 1992, TETRAHEDRON, V48, P4459
  • [5] TOTAL SYNTHESIS OF THE TRIQUINANE MARINE SESQUITERPENE (PLUS-OR-MINUS)DELTA(9(12)) CAPNELLENE USING A PALLADIUM-CATALYZED BIS-CYCLIZATION STEP
    BALME, G
    BOUYSSI, D
    [J]. TETRAHEDRON, 1994, 50 (02) : 403 - 414
  • [6] Total synthesis of the tricyclic sesquiterpene (+/-)-ceratopicanol. An illustration of the holosynthon concept
    Baralotto, C
    Chanon, M
    Julliard, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3576 - 3577
  • [7] From toluene to triquinanes: formal total syntheses of the sesquiterpenoid natural products (-)-hypnophilin and (-)-coriolin
    Bon, David J. -Y. D.
    Banwell, Martin G.
    Ward, Jas S.
    Willis, Anthony C.
    [J]. TETRAHEDRON, 2013, 69 (04) : 1363 - 1368
  • [8] The total synthesis of (-)-connatusin A, a hirsutane-type sesquiterpene isolated from the fungus Lentinus connatus BCC8996
    Bon, David J. -Y. D.
    Banwell, Martin G.
    Cade, Ian A.
    Willis, Anthony C.
    [J]. TETRAHEDRON, 2011, 67 (43) : 8348 - 8352
  • [9] A chemoenzymatic total synthesis of the hirsutene-type sesquiterpene (+)-connatusin B from toluene
    Bon, David J. -Y. D.
    Banwell, Martin G.
    Willis, Anthony C.
    [J]. TETRAHEDRON, 2010, 66 (39) : 7807 - 7814
  • [10] ASYMMETRIC APPROACH TO PAUSON-KHAND BICYCLIZATION - ENANTIOSELECTIVE FORMAL SYNTHESIS OF HIRSUTENE
    CASTRO, J
    SORENSEN, H
    RIERA, A
    MORIN, C
    MOYANO, A
    PERICAS, MA
    GREENE, AE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) : 9388 - 9389