C ring may be dispensable for β-carboline: Design, synthesis, and bioactivities evaluation of tryptophan analog derivatives based on the biosynthesis of β-carboline alkaloids

被引：17

作者：

Huang, Yuanqiong ^{[1
]}

Liu, Yongxian ^{[1
]}

Liu, Yuxiu ^{[1
]}

Song, Hongjian ^{[1
]}

Wang, Qingmin ^{[1
]}

机构：

[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Res Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2016年 / 24卷 / 03期

基金：

中国国家自然科学基金;

关键词：

beta-Carboline; Tryptophan; Biosynthesis; Anti-TMV; Fungicide; BIOLOGICAL-ACTIVITIES; PATHWAY;

D O I：

10.1016/j.bmc.2015.08.016

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：

According to our previous work and the latest research on the biosynthesis of beta-carboline, and using the reverse thinking strategy, tryptophan, the biosynthesis precursor of beta-carboline alkaloids, and their derivatives were synthesized, and their biological activities and structure-activity relationships were studied. This bioassay showed that these compounds exhibited good inhibitory activities against tobacco mosaic virus (TMV); especially (S)-2-amino-3-(1H-indol-3-yl)-N-octylpropanamide (4) (63.3 +/- 2.1%, 67.1 +/- 1.9%, 68.7 +/- 1.3%, and 64.5 +/- 3.1%, 500 mu g/mL) exhibited the best antiviral activity both in vitro and in vivo. Compound 4 was chosen for the field trials and the acute oral toxicity test, the results showed that the compound exhibited good anti-TMV activity in the field and low acute oral toxicity. We also found that these compounds showed antifungal activities and insecticidal activities. (C) 2016 Published by Elsevier Ltd.

引用

页码：462 / 473

页数：12

共 21 条

[1] Design of antimicrobial compounds based on peptide structures [J].

Appelt, Christian ;

Schrey, Anna K. ;

Soederhaell, J. Arvid ;

Schmieder, Peter .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (08) :2334-2337

[2] Discovery of McbB, an Enzyme Catalyzing the β-Carboline Skeleton Construction in the Marinacarboline Biosynthetic Pathway [J].

Chen, Qi ;

Ji, Changtao ;

Song, Yongxiang ;

Huang, Hongbo ;

Ma, Junying ;

Tian, Xinpeng ;

Ju, Jianhua .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) :9980-9984

[3]

Kang G. Y., 2015, CARCINOG TERATOGENES, V25, P272

[4] A concise preparation of the non-proteinogenic amino acid L-kynurenine [J].

Kleijn, Laurens H. J. ;

Muskens, Frederike M. ;

Oppedijk, Sabine F. ;

de Bruin, Gerjan ;

Martin, Nathaniel I. .

TETRAHEDRON LETTERS, 2012, 53 (47) :6430-6432

[5]

Kohki T., 1981, [No title captured], Patent No. [EP 0032708 A1, 0032708]

[6] Design, Synthesis, and Biological Activities of Aromatic Gossypol Schiff Base Derivatives [J].

Li, Ling ;

Li, Zheng ;

Wang, Kailiang ;

Zhao, Sheng ;

Feng, Jiming ;

Li, Jiarui ;

Yang, Peiwen ;

Liu, Yuxiu ;

Wang, Lizhong ;

Li, Yongqiang ;

Shang, Hui ;

Wang, Qingmin .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2014, 62 (46) :11080-11088

[7]

Li WM, 2009, CHEM J CHINESE U, V30, P728

[8] Elucidation of the Concise Biosynthetic Pathway of the Communesin Indole Alkaloids [J].

Lin, Hsiao-Ching ;

Chiou, Grace ;

Chooi, Yit-Heng ;

McMahon, Travis C. ;

Xu, Wei ;

Garg, Neil K. ;

Tang, Yi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (10) :3004-3007

[9] Design, Synthesis, and Antiviral, Fungicidal, and Insecticidal Activities of Tetrahydro-β-carboline-3-carbohydrazide Derivatives [J].

Liu, Yongxian ;

Song, Hongjian ;

Huang, Yuanqiong ;

Li, Jiarui ;

Zhao, Sheng ;

Song, Yuchuan ;

Yang, Peiwen ;

Xiao, Zhixin ;

Liu, Yuxiu ;

Li, Yongqiang ;

Shang, Hui ;

Wang, Qingmin .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2014, 62 (41) :9987-9999

[10]

Lobb K. L., 1998, [No title captured], Patent No. [US 005792760 A, 005792760, 5792760]

← 1 2 3 →