Rubrumazines A-C, Indolediketopiperazines of the Isoechinulin Class from Eurotium rubrum MA-150, a Fungus Obtained from Marine Mangrove-Derived Rhizospheric Soil.
Three new indolediketopiperazine alkaloids of the isoechinulin type, rubrumazines A-C (1-3), each possessing an oxygenated prenyl group either at C-7 (1 and 2) or at C-5 (3), along with 13 related analogues (4-16), were isolated and identified from a culture extract of Eurotium rubrum MA-150, a fungus obtained from mangrove-derived rhizospheric soil collected from the Andaman Sea coastline, Thailand. Their structures were established by detailed interpretation of NMR spectroscopic and mass spectrometry data analysis. The structure and absolute configuration of compound 1 were confirmed by X-ray crystallographic analysis, thus providing the first characterized crystal structure of an isoechinulin-type alkaloid. All isolated compounds were evaluated for brine shrimp lethality and antibacterial activity.
†Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.|‡University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, People's Republic of China.
Ling-Hong
LH
Meng
†Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.
Feng-Yu
FY
Du
†Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.
Xiao-Ming
XM
Li
⊥Aquatic Animal Health Management Research Unit, Faculty of Sciences and Fishery Technology, RMUTSV, Trang Campus Sikao District, Trang Province 92150, Thailand.
Patchara
P
Pedpradab
†Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.
Gang-Ming
GM
Xu
†Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.
Bin-Gui
BG
Wang
D000818:Animals; D018360:Crystallography, X-Ray; D055325:Eurotium / Q000737:chemistry*; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D043982:Rhizophoraceae / Q000382:microbiology*; D013785:Thailand
D026121:Indole Alkaloids; C000600431:rubrumazine A; C000600432:rubrumazine B; C000600433:rubrumazine C