Diterpene alkaloids with an aza-ent-kaurane skeleton from Isodon rubescens.

Two compounds belonging to a new group of diterpene alkaloids, kaurines A and B (1 and 2), and an alkaloid bearing a succinimide moiety (3) were obtained from Isodon rubescens. Their structures and absolute configurations were determined by spectroscopy and quantum-chemical computational (13)C NMR and ECD data analysis. These alkaloids differ from known diterpene alkaloids and diterpenoids and are presumably biosynthesized from ent-kaurane diterpenoids.

[1]  Jie Cao,et al.  Feeding deterrents from Aconitum episcopale roots against the red flour beetle, Tribolium castaneum. , 2011, Journal of agricultural and food chemistry.

[2]  Yan Li,et al.  Laxiflorolides A and B, epimeric bishomoditerpene lactones from Isodon eriocalyx. , 2012, Journal of natural products.

[3]  Stefan Grimme,et al.  Systematic Investigation of Modern Quantum Chemical Methods to Predict Electronic Circular Dichroism Spectra , 2003 .

[4]  P. Gerner,et al.  Bulleyaconitine A Isolated from Aconitum Plant Displays Long-acting Local Anesthetic Properties In Vitro and In Vivo , 2007, Anesthesiology.

[5]  J. MacMillan,et al.  Erythrazoles A-B, cytotoxic benzothiazoles from a marine-derived Erythrobacter sp. , 2011, Organic letters.

[6]  J. Bonjoch,et al.  Total synthesis of (-)-anominine. , 2010, Journal of the American Chemical Society.

[7]  D A Scudiero,et al.  Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. , 1988, Cancer research.

[8]  D. Christianson.  Roots of Biosynthetic Diversity , 2007, Science.

[9]  Wei‐Lie Xiao,et al.  Cytotoxic ent-kauranoid derivatives from Isodon rubescens , 2006 .

[10]  Chen-chen Zhu,et al.  Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii. , 2012, Journal of natural products.

[11]  Han-Dong Sun,et al.  Rubescensins S and T: Seco-ent-Kaurane Diterpenoids from Isodon rubescens var. taihangensis , 2004 .

[12]  Hong-ping He,et al.  Approach to the biosynthesis of atisine-type diterpenoid alkaloids. , 2009, Journal of natural products.

[13]  B. Potter,et al.  Nudicauline and elatine as potent norditerpenoid ligands at rat neuronal alpha-bungarotoxin binding sites: importance of the 2-(methylsuccinimido)benzoyl moiety for neuronal nicotinic acetylcholine receptor binding. , 1996, Journal of medicinal chemistry.

[14]  B. Moore,et al.  Merochlorins A–D, Cyclic Meroterpenoid Antibiotics Biosynthesized in Divergent Pathways with Vanadium-Dependent Chloroperoxidases , 2012 .

[15]  C. Afonso,et al.  Isolation, chemical, and biotransformation routes of labdane-type diterpenes. , 2011, Chemical reviews.

[16]  Han-Dong Sun,et al.  Diterpenoids from Isodon species and their biological activities. , 2006, Natural product reports.

[17]  Cuirong Sun,et al.  Isolation and purification of oridonin from Rabdosia rubescens using upright counter-current chromatography. , 2006, Journal of separation science.

[18]  Ikuo Kashiwakura,et al.  Inhibitory effects of diterpenoid alkaloids on the growth of A172 human malignant cells. , 2007, Journal of natural products.