Alterbrassinoids A-D: Fusicoccane-Derived Diterpenoid Dimers Featuring Different Carbon Skeletons from Alternaria brassicicola

被引：33

作者：

Li, Fengli ^{[1
]}

Lin, Shuang ^{[1
]}

Zhang, Sitian ^{[1
]}

Hao, Xincai ^{[2
]}

Li, Xiao-Nian ^{[3
]}

Yang, Beiye ^{[1
]}

Liu, Junjun ^{[1
]}

Wang, Jianping ^{[1
]}

Hu, Zhengxi ^{[1
]}

Zhane, Yonghui ^{[1
]}

机构：

[1] Huazhong Univ Sci & Technol, Tongji Med Coll, Sch Pharm, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Hubei, Peoples R China

[2] Hubei Univ Med, Coll Pharm, Shiyan 442000, Peoples R China

[3] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 20期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1021/acs.orglett.9b03133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alterbrassinoids A-D (1-4), the first examples of fusicoccane-derived diterpenoid dimers furnished by forming an undescribed C-12-C-18' linkage, were isolated from modified cultures of Alternaria brassicicola. Compounds 1 and 2 represent unprecedented heterodimers, whereas 3 and 4 represent unprecedented homodimers, and 4 also features an undescribed anhydride motif. Their structures were assigned via spectroscopic methods, electronic circular dichroism calculations, and single -crystal X-ray diffraction. Putative biosynthetic pathways and a bioactivity evaluation for 1-4 were discussed.

引用

页码：8353 / 8357

页数：5

共 14 条

[1]

Bode HB, 2002, CHEMBIOCHEM, V3, P619, DOI 10.1002/1439-7633(20020703)3:7<619::AID-CBIC619>3.0.CO

[2]

2-9

[3] Fusicoccane-Derived Diterpenoids from Alternaria brassicicola: Investigation of the Structure-Stability Relationship and Discovery of an IKKβ Inhibitor [J].

Hu, Zhengxi ;

Sun, Weiguang ;

Li, Fengli ;

Guan, Jiankun ;

Lu, Yuanyuan ;

Liu, Junjun ;

Tang, Ying ;

Du, Guang ;

Xue, Yongbo ;

Luo, Zengwei ;

Wang, Jianping ;

Zhu, Hucheng ;

Zhang, Yonghui .

ORGANIC LETTERS, 2018, 20 (17) :5198-5202

[4] Phomopsterones A and B, Two Functionalized Ergostane-Type Steroids from the Endophytic Fungus Phomopsis sp TJ507A [J].

Hu, Zhengxi ;

Wu, Ye ;

Xie, Shuangshuang ;

Sun, Weiguaug ;

Guo, Yi ;

Li, Xiao-Nian ;

Liu, Junjun ;

Li, Hua ;

Wang, Jianping ;

Luo, Zengwei ;

Xue, Yongbo ;

Zhang, Yonghui .

ORGANIC LETTERS, 2017, 19 (01) :258-261

[5] Activation of the plant plasma membrane H+-ATPase by phosphorylation and binding of 14-3-3 proteins converts a dimer into a hexamer [J].

Kanczewska, J ;

Marco, S ;

Vandermeeren, C ;

Maudoux, O ;

Rigaud, JL ;

Boutry, M .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (33) :11675-11680

[6] Alterbrassicicene A, a Highly Transformed Fusicoccane-Derived Diterpenoid with Potent PPAR-γ Agonistic Activity from Alternaria brassicicola [J].

Li, Fengli ;

Sun, Weiguang ;

Guan, Jiankun ;

Lu, Yuanyuan ;

Zhang, Sitian ;

Lin, Shuang ;

Liu, Junjun ;

Gao, Weixi ;

Wang, Jianping ;

Hu, Zhengxi ;

Zhang, Yonghui .

ORGANIC LETTERS, 2018, 20 (24) :7982-7986

[7]

Li FL, 2018, ORG BIOMOL CHEM, V16, P8751, DOI [10.1039/c8ob02353k, 10.1039/C8OB02353K]

[8] Modulators of 14-3-3 Protein-Protein Interactions [J].

Stevers, Loes M. ;

Sijbesma, Eline ;

Botta, Maurizio ;

MacKintosh, Carol ;

Obsil, Tomas ;

Landrieu, Isabelle ;

Cau, Ylenia ;

Wilson, Andrew J. ;

Karawajczyk, Anna ;

Eickhoff, Jan ;

Davis, Jeremy ;

Hann, Michael ;

O'Mahony, Gavin ;

Doveston, Richard G. ;

Brunsveld, Luc ;

Ottmann, Christian .

JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (09) :3755-3778

[9] Phosphopeptide-Dependent Labeling of 14-3-3?? Proteins by Fusicoccin-Based Fluorescent Probes [J].

Takahashi, Michiko ;

Kawamura, Akie ;

Kato, Nobuo ;

Nishi, Tsuyoshi ;

Hamachi, Itaru ;

Ohkanda, Junko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (02) :509-512

[10] Structural Revisions of a Class of Natural Products: Scaffolds of Aglycon Analogues of Fusicoccins and Cotylenins Isolated from Fungi [J].

Tang, Ying ;

Xue, Yongbo ;

Du, Guang ;

Wang, Jianping ;

Liu, Junjun ;

Sun, Bin ;

Li, Xiao-Nian ;

Yao, Guangmin ;

Luo, Zengwei ;

Zhang, Yonghui .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (12) :4069-4073

← 1 2 →