Quinolizidine Alkaloids from Cylicomorpha solmsii.

Five new quinolizidine alkaloids were isolated from the leaves of Cylicomorpha solmstii (Urb.) Urb. (Caricaceae) and named cylicomorphins A-E (1-5). They all are ester derivatives of the same basic quinolizidine skeleton bearing hydroxy, methyl, and ethanoic acid substituents. Their structures were mainly established by NMR spectroscopy, and the absolute configuration is proposed on the basis of VCD data and Mosher ester derivatization. Compound 5 displayed cytotoxicity in the 10 μM range against an HCT-116 cell line.

[1]  C. Merten,et al.  Explicit Solvation of Carboxylic Acids for Vibrational Circular Dichroism Studies: Limiting the Computational Efforts without Losing Accuracy. , 2018, The journal of physical chemistry. B.

[2]  Kazuki Saito,et al.  Quinolizidine alkaloid biosynthesis: recent advances and future prospects , 2012, Front. Plant Sci..

[3]  P. Polavarapu,et al.  Chiroptical spectroscopy of natural products: avoiding the aggregation effects of chiral carboxylic acids. , 2012, Journal of natural products.

[4]  A. Fongod,et al.  Ethnobotany survey and uses of plants in the Lewoh- Lebang communities in the Lebialem highlands, South West Region, Cameroon , 2012 .

[5]  W. Vilegas,et al.  Absolute configuration and selective trypanocidal activity of gaudichaudianic acid enantiomers. , 2011, Journal of natural products.

[6]  P. Dewick Comprar Medicinal Natural Products: A Biosynthetic Approach | Paul M. Dewick | 9780470741672 | Wiley , 2009 .

[7]  S. Blechert,et al.  Concise total synthesis of (+)-carpamic acid , 2004 .

[8]  R. Kiss,et al.  Enantioselective Synthesis of Clavepictine Analogues and Evaluation of Their Cytotoxic Activity , 2003 .

[9]  J. Pezzuto,et al.  New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient Mosher ester procedure carried out in NMR tubes. , 2002, Journal of natural products.

[10]  G. Kusano,et al.  Five new nortropane alkaloids and six new amino acids from the fruit of Morus alba LINNE growing in Turkey. , 2002, Chemical & pharmaceutical bulletin.

[11]  N. Toyooka,et al.  Highly stereoselective construction of 4,6-cis-substituted quinolizidine ring core: an application to enantioselective total synthesis of the marine alkaloid clavepictines A, B and pictamine , 1999 .

[12]  J. Cha,et al.  Total Synthesis of Clavepictines A and B. Diastereoselective Cyclization of δ-Aminoallenes , 1999 .

[13]  N. Toyooka,et al.  Enantioselective Total Synthesis of the Marine Alkaloid Clavepictines A and B , 1996 .

[14]  D. Kingston,et al.  BIOACTIVE AND OTHER PIPERIDINE ALKALOIDS FROM CASSIA-LEPTOPHYLLA , 1995 .

[15]  D. Faulkner,et al.  Pictamine, a quinolizidine alkaloid from the tunicate Clavelina picta , 1991 .

[16]  J. Clardy,et al.  Clavepictines A and B: Cytotoxic Quinolizidines from the Tunicate Clavelina picta , 1991 .

[17]  G. Massiot,et al.  Synthesis of (–)-ajmalicine from (–)-tryptophan , 1984 .

[18]  J. Winkler,et al.  STEREOCHEMICAL CONTROL OF THE INTERNAL MICHAEL REACTION. A NEW CONSTRUCTION OF TRANS-HYDRINDAN SYSTEMS , 1982 .

[19]  I. Christofidis,et al.  Spectaline and iso-6 cassine, two new piperidin 3-ol alkaloids from the leaves of cassia spectabilis , 1977 .