Chloranthones A – D: Minor and Unprecedented Dinor‐Eudesmenes from Chloranthus elatior

Four novel naturally occurring diastereoisomers of dinor‐eudesmenes, named chloranthones A–D (1–4, resp.), were isolated as minor components from the EtOH extract of the aerial parts of Chloranthus elatior. The unprecedented framework was established using extensive 2D‐NMR techniques. Their absolute configurations were deduced from the observed Cotton effects in their circular dichroism (CD) spectra. A plausible biosynthetic pathway to the dinor‐eudesmenes is proposed.

[1]  J. Xiong,et al.  Sesquiterpenoids from the aerial parts of Chloranthus elatior , 2013 .

[2]  J. Xiong,et al.  Fomentarols A-D, sterols from the polypore macrofungus Fomes fomentarius. , 2013, Phytochemistry.

[3]  A. Maier,et al.  Kandenols A-E, eudesmenes from an endophytic Streptomyces sp. of the mangrove tree Kandelia candel. , 2012, Journal of natural products.

[4]  J. Xiong,et al.  Sesquiterpene lactones from the aerial parts of Xanthium sibiricum and their cytotoxic effects on human cancer cell lines , 2012 .

[5]  Haiyang Liu,et al.  Terpenoids from Chloranthus elatior , 2012, Natural Products and Bioprospecting.

[6]  Guozhu Wei,et al.  Chlorantholides A-F, eudesmane-type sesquiterpene lactones from Chloranthus elatior. , 2012, Phytochemistry.

[7]  Jin-Feng Hu,et al.  Antiproliferative and apoptotic sesquiterpene lactones from Carpesium faberi. , 2011, Bioorganic & medicinal chemistry letters.

[8]  R. Utsumi,et al.  Diversity, regulation, and genetic manipulation of plant mono- and sesquiterpenoid biosynthesis , 2009, Cellular and Molecular Life Sciences.

[9]  X. Yao,et al.  Two new eremophilanolides from Xanthium sibiricum , 2006, Natural product research.

[10]  E. Garo,et al.  Cyclolignans from Scyphocephalium ochocoa via high-throughput natural product chemistry methods. , 2005, Phytochemistry.

[11]  M. O'Neil-Johnson,et al.  Application of capillary-scale NMR for the structure determination of phytochemicals. , 2005, Phytochemical analysis : PCA.

[12]  E. Garo,et al.  Miniaturization of the Structure Elucidation of Novel Natural Products - Two Trace Antibacterial Acylated Caprylic Alcohol Glycosides from Arctostaphylos pumila , 2005, Planta medica.

[13]  M. O'Neil-Johnson,et al.  Suaveolindole, a new mass-limited antibacterial indolosesquiterpene from Greenwayodendron suaveolens obtained via high-throughput natural products chemistry methods. , 2005, Journal of natural products.

[14]  Jin-Feng Hu,et al.  Eudesmane sesquiterpenes from Artemisia eriopoda , 1996 .

[15]  T. Takemoto,et al.  Structure and absolute configuration of α-rotunol and β-rotunol, sesquiterpenoids of Cyperus rotundus , 1971 .