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Authors Wang, P; Kong, FD; Wei, JJ; Wang, Y; Wang, W; Hong, K; Zhu, WM
Author Full Name Wang, Pei; Kong, Fandong; Wei, Jingjing; Wang, Yi; Wang, Wei; Hong, Kui; Zhu, Weiming
Title Alkaloids from the Mangrove-Derived Actinomycete Jishengella endophytica 161111
Source MARINE DRUGS
Language English
Document Type Article
Author Keywords mangrove; actinomycete; Jishengella endophytica 161111; pyrazine derivative; anti-H1N1 virus activity
Keywords Plus BETA-CARBOLINE ALKALOIDS; NITROGEN-CONTAINING COMPOUNDS; TUNICATE EUDISTOMA SP; TETRACYCLIC EUDISTOMINS; NATURAL-PRODUCTS; SPONGE; AGENTS; INDOLE; ACID; FLAZINAMIDE
Abstract A new alkaloid, 2-(furan-2-yl)-6-(2S,3S,4-trihydroxybutyl) pyrazine (1), along with 12 known compounds, 2-(furan-2-yl)-5-(2S,3S,4-trihydroxybutyl) pyrazine (2), (S)-4-isobutyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (3), (S)-4-isopropyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (4), (4S)-4-(2-methylbutyl)-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (5), (S)-4-benzyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (6), flazin (7), perlolyrine (8), 1-hydroxy-beta-carboline (9), lumichrome (10), 1H-indole-3-carboxaldehyde (11), 2-hydroxy-1-(1H-indol-3-yl)ethanone (12), and 5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde (13), were isolated and identified from the fermentation broth of an endophytic actinomycetes, Jishengella endophytica 161111. The new structure 1 and the absolute configurations of 2-6 were determined by spectroscopic methods, J-based configuration analysis (JBCA) method, lactone sector rule, and electronic circular dichroism (ECD) calculations. Compounds 8-11 were active against the influenza A virus subtype H1N1 with IC50 and selectivity index (SI) values of 38.3(+/- 1.2)/25.0(+/- 3.6)/39.7(+/- 5.6)/45.9(+/- 2.1) mu g/mL and 3.0/16.1/3.1/11.4, respectively. The IC50 and SI values of positive control, ribavirin, were 23.1(+/- 1.7) mu g/mL and 32.2, respectively. The results showed that compound 9 could be a promising new hit for anti-H1N1 drugs. The absolute configurations of 2-5, C-13 nuclear magnetic resonance (NMR) data and the specific rotations of 3-6 were also reported here for the first time.
Author Address [Wang, Pei; Kong, Fandong; Wang, Yi; Wang, Wei; Zhu, Weiming] Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Minist Educ China, Qingdao 266003, Peoples R China; [Wei, Jingjing; Hong, Kui] Wuhan Univ, Sch Pharmaceut Sci, Key Lab Combinatorial Biosynth & Drug Discovery, Minist Educ, Wuhan 430071, Peoples R China
Reprint Address Hong, K (corresponding author), Wuhan Univ, Sch Pharmaceut Sci, Key Lab Combinatorial Biosynth & Drug Discovery, Minist Educ, Wuhan 430071, Peoples R China.
E-mail Address wangpei850212@163.com; kongfandong501@126.com; rxwzq@163.com; wangyi0213@ouc.edu.cn; wwwakin@ouc.edu.cn; kuihong31@whu.edu.cn; weimingzhu@ouc.edu.cn
ResearcherID Number Wang, Wei/W-8492-2019
Funding Agency and Grant Number 973 Program of ChinaNational Basic Research Program of China [2010CB833804]; NSFCNational Natural Science Foundation of China (NSFC) [41376148, 21172204, 81373298, 31170467]; 863 Program of ChinaNational High Technology Research and Development Program of China [2013AA092901, 2012AA092104, 2011AA09070106]; Special Fund for Marine Scientific Research in the Public Interest of China [2010418022-3]
Funding Text This work was financially supported by the grants from 973 Program of China (No. 2010CB833804), from NSFC (Nos. 41376148, 21172204, 81373298 & 31170467), from 863 Program of China (Nos. 2013AA092901, 2012AA092104 and 2011AA09070106), and from the Special Fund for Marine Scientific Research in the Public Interest of China (No. 2010418022-3). The authors are grateful to Haipeng Lin (Institute of Tropical Biosiences and Biotechnology) for his help on preparing the crude extracts from the 100 L fermentation broth.
Times Cited 36
Total Times Cited Count (WoS, BCI, and CSCD) 43
Publisher MDPI
Publisher City BASEL
Publisher Address ST ALBAN-ANLAGE 66, CH-4052 BASEL, SWITZERLAND
ISSN 1660-3397
29-Character Source Abbreviation MAR DRUGS
ISO Source Abbreviation Mar. Drugs
Publication Date JAN
Year Published 2014
Volume 12
Issue 1
Beginning Page 477
Ending Page 490
Digital Object Identifier (DOI) 10.3390/md12010477
Page Count 14
Web of Science Category Chemistry, Medicinal; Pharmacology & Pharmacy
Subject Category Pharmacology & Pharmacy
Document Delivery Number AH4HH
Unique Article Identifier WOS:000336087500025
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