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001-es BibID:BIBFORM096035
035-os BibID:(WoS)000669624100001 (Scopus)85112673062
Első szerző:Jiang, Zhong-Ping
Cím:Discovery of benthol A and its challenging stereochemical assignment: opening up a new window for skeletal diversity of super-carbon-chain compounds / Zhong-Ping Jiang, Shi-Hao Sun, Yi Yu, Attila Mándi, Jiao-Yang Luo, Mei-Hua Yang, Tibor Kurtán, Wen-Hua Chen, Li Shen, Jun Wu
Dátum:2021
ISSN:2041-6520 2041-6539
Megjegyzések:Super-carbon-chain compounds (SCCCs) are marine organic molecules featuring long polyol carbon chains with numerous stereocenters. Polyol?polyene compounds (PPCs) and ladder-frame polyethers (LFPs) are two major families. It is highly challenging to establish the absolute configurations of SCCCs. In this century, few new SCCC families have been reported. Benthol A, an aberrant SCCC, was obtained from a South China Sea benthic dinoflagellate that should belong to a new taxon. Its planar structure and absolute configuration, containing thirty-five carbon stereocenters, were unambiguously established by a combination of extensive NMR spectroscopic investigations, periodate degradation of the 1,2-diol groups, ozonolysis of the carbon-carbon double bonds, J-based configurational analysis, NOE interactions, modified Mosher's MTPA ester method, and DFT-NMR 13C chemical-shift calculations aided by DP4+ statistical analysis. Benthol A displayed potent antimalarial activity against Plasmodium falciparum 3D7 parasites. This new molecule combines extraordinary structural features, particularly eight scattered ether rings on a C72 backbone chain, which places it within a new SCCC family between PPCs and LFPs, herein termed polyol?polyether compounds. This suggestion was strongly supported by principal component analysis. The discovery of benthol A does not only provide new insights into the untapped biosynthetic potential of marine dinoflagellates, but also opens up a new window for skeletal diversity of SCCCs.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
folyóiratcikk
Megjelenés:Chemical Science. - 12 : 30 (2021), p. 10197-10206. -
További szerzők:Sun, Shi-Hao Yu, Yi Mándi Attila (1981-) (vegyész, német szakfordító) Luo, Jiao-Yang Yang, Mei-Hua Kurtán Tibor (1973-) (vegyész, angol szakfordító) Chen, Wen-Hua Shen, Li Wu, Jun
Pályázati támogatás:GINOP-2.3.2-15-2016-00008
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NKFI K120181
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NKFI FK134653
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