(+)- and (-)-Pestaloxazine A, a Pair of Antiviral Enantiomeric Alkaloid Dimers with a Symmetric Spiro[oxazinane-piperazinedione] Skeleton from Pestalotiopsis sp.
A pair of new enantiomeric alkaloid dimers, (+)- and (-)-pestaloxazine A (1), with an unprecedented symmetric spiro[oxazinane-piperazinedione] skeleton, consisting of 22 carbons and 12 heteroatoms, were isolated from a Pestalotiopsis sp. fungus derived from a soft coral. Separation of the enantiomeric alkaloid dimers was achieved by chiral HPLC. Their structures including absolute configurations were elucidated on the basis of a comprehensive analysis of their spectroscopic and X-ray diffraction data and CD calculations. (+)-Pestaloxazine A exhibited potent antiviral activity against EV71 with an IC50 value of 14.2 ± 1.3 μM, which was stronger than that of the positive control ribavirin (IC50 = 256.1 ± 15.1 μM).
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China , Qingdao, 266003, The People's Republic of China.|Shandong Institute for Product Quality Inspection, Jinan, 250102, The People's Republic of China.
Yan-Lai
YL
Jia
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China , Qingdao, 266003, The People's Republic of China.|School of Pharmacy, Guangdong Medical University , Dongguan, 523808, The People's Republic of China.
Mei-Yan
MY
Wei
School of Chemistry and Chemical Engineering, Guangxi University, Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Nanning, 530004, The People's Republic of China.
Hai-Yan
HY
Chen
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China , Qingdao, 266003, The People's Republic of China.
Fei-Fei
FF
Guan
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China , Qingdao, 266003, The People's Republic of China.
Chang-Yun
CY
Wang
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China , Qingdao, 266003, The People's Republic of China.
Chang-Lun
CL
Shao
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D029821:Enterovirus A, Human / Q000187:drug effects; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013237:Stereoisomerism; D013098:Xylariales / Q000737:chemistry
D000470:Alkaloids; D000998:Antiviral Agents; D010879:Piperazines; D013141:Spiro Compounds; C000603434:pestaloxazine A