Isoindolinone-type alkaloids from the sponge-derived fungus Stachybotrys chartarum

被引：45

作者：

Li, Yong ^{[1
]}

Liu, Dong ^{[1
]}

Cen, Shan ^{[2
]}

Proksch, Peter ^{[3
]}

Lin, Wenhan ^{[1
]}

机构：

[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

[2] Chinese Acad Med Sci, Inst Med Biotechnol, Beijing 100050, Peoples R China

[3] Univ Dusseldorf, Inst Pharmaceut Biol & Biotechnol, D-40225 Dusseldorf, Germany

来源：

TETRAHEDRON | 2014年 / 70卷 / 39期

关键词：

Isoindolinone-type Alkaloids; Chartarutines A-H; Structural elucidation; Anti-HIV activity; Structure-activity relationship; ABSOLUTE-CONFIGURATION; DERIVATIVES; SPIRODIHYDROBENZOFURANLACTAMS; PHENYLSPIRODRIMANES; MO-2(OAC)(4); ANTAGONISTS; ENDOTHELIN; INHIBITORS; 1,2-DIOLS;

D O I：

10.1016/j.tet.2014.07.047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Eight new isoindolinone-type alkaloids named chartarutines A-H (1-8) and a known analogue (9) were isolated from the sponge-associated fungus Stachybotrys chartarum. Their structures were elucidated by extensive spectroscopic (IR, MS, 1D, and 2D NMR) data analyses, in addition to the Mosher method and CD effects for the assignment of their absolute configurations. All compounds were evaluated for the inhibition against HIV-1 virus, while chartarutines B, G, and H exhibited significant inhibitory effects. Primary structure activity relationship was discussed. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：7010 / 7015

页数：6

共 20 条

[1]

[Anonymous], [No title captured]

[2] Formamidobisabolene-based derivatives from a sponge Axinyssa sp. [J].

Cheng, Wei ;

Liu, Dong ;

Zhang, Fengying ;

Zhang, Qingying ;

Pedpradab, Patchara ;

Proksch, Peter ;

Liang, Hong ;

Lin, Wenhan .

TETRAHEDRON, 2014, 70 (22) :3576-3583

[3]

CRABBE P, 1969, CHEM IND-LONDON, P917

[4] Determination of absolute configuration of acyclic 1,2-diols with Mo2(OAc)4.: 1.: Snatzke's method revisited [J].

Di Bari, L ;

Pescitelli, G ;

Pratelli, C ;

Pini, D ;

Salvadori, P .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) :4819-4825

[5] Practical method for the absolute configuration assignment of tert/tert 1,2-diols using their complexes with Mo2(OAc)4 [J].

Gorecki, Marcin ;

Jablonska, Ewa ;

Kruszewska, Anna ;

Suszczynska, Agata ;

Urbanczyk-Lipkowska, Zofia ;

Gerards, Michael ;

Morzycki, Jacek W. ;

Szczepek, Wojciech J. ;

Frelek, Jadwiga .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (08) :2906-2916

[6] Atranones:: Novel diterpenoids from the toxigenic mold Stachybotrys atra [J].

Hinkley, SF ;

Jiang, J ;

Mazzola, EP ;

Jarvis, BB .

TETRAHEDRON LETTERS, 1999, 40 (14) :2725-2728

[7] A DITERPENE RELATED TO CLADIELLIN FROM A PACIFIC SOFT CORAL [J].

HOCHLOWSKI, JE ;

FAULKNER, DJ .

TETRAHEDRON LETTERS, 1980, 21 (42) :4055-4056

[8] Structures and histamine release inhibitory effects of prenylated orcinol derivatives from Rhododendron dauricum [J].

Iwata, N ;

Wang, NL ;

Yao, XS ;

Kitanaka, S .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (07) :1106-1109

[9]

Jarvis Bruce B., 1995, Natural Toxins, V3, P10, DOI 10.1002/nt.2620030104

[10] Chartarlactams A-P, Phenylspirodrimanes from the Sponge-Associated Fungus Stachybotrys chartarum with Antihyperlipidemic Activities [J].

Li, Yong ;

Wu, Chongming ;

Liu, Dong ;

Proksch, Peter ;

Guo, Peng ;

Lin, Wenhan .

JOURNAL OF NATURAL PRODUCTS, 2014, 77 (01) :138-147

← 1 2 →