Seung Ho Lee, Jong-Keun Son, Byeong Seon Jeong, Tae-Cheon Jeong, Hyeon Wook Chang, Eung-Seok Lee and Yurngdong Jahng *
College of Pharmacy, Yeungnam University, Gyeongsan 712-749 Korea
* Author to whom correspondence should be addressed; E-mail: ydjahng@ynu.ac.kr
Received: 1 January 2008; in revised form 1 February 2008 / Accepted: 2 February 2008 / Published: 6 February 2008
Review: Progress in the Studies on Rutaecarpine
Molecules 2008, 13, 272-300 (PDF format 1116 K)
Type of the paper: Review
Tentative Title: Analysis of Isoquinoline Alkaloids by Liquid Chromatography Methods
Author: Monika Waskmundzka-Hajnos
E-mail: monika.hajnos@am.lublin.pl
Type of the paper: Review
Tentative Title: Selective Accounts on Bioactive Alkaloids from Marine Organisms
Author: Phil Crews
E-mail: phil@chemistry.ucsc.edu
Department of Chemistry, University of California, 1156 High Street, Santa Cruz, CA 95064, USA
http://chemistry.ucsc.edu/faculty/crews.html
Molecules Manuscript ID: alkaloids-20071229-Palazon-es
Type of the paper: Review
Title: Application of Metabolic Engineering to the Production of Scopolamine
Authors: Prof. Javier Palazon
Laboratorio de Fisiologia Vegetal
Facultad de Farmacia
Universidad de Barcelona
AVD/ Diagonal 643. 08028 Barcelona. Spain
Tel. +34934024493; Fax. +34934024093
E-mail: javierpalazon@ub.edu
Abstract: Scopolamine is an alkaloid widely used in medicine for its anticholinergic activity. The aim of this review is to show that metabolic engineering techniques constitute a suitable tool to improve the production of tropane alkaloids, focusing in particular on scopolamine. We present an overview of results obtained by various research groups, including ourselves, who have studied the overexpression of genes involved in the biosynthesis of scopolamine in different plant species that produce tropane alkaloids. Experiments carried out to improve production in hairy root cultures will also be described, as well as those attempting to biotransform hyoscyamine into scopolamine in roots and transgenic tobacco cells.
Molecules Manuscript ID: alkaloids-20071203-Sultana-pk
Type of the paper: Review
Title: Pharmacological and spectral studies on Quinoline Alkaloids from Skimmia laureola
Authors: Nighat Sultana* and Ather Ata
E-mail: nighat2001us@yahoo.com
Abstract: This review covers the introduction, pharmacological activities, the spectral features and biosynthesis of quinoline alkaloids in Skimmia laureola. The aim of the present study is to describe the pharmacological and spectral features of constituents of Skimmia laureola. The pharmacological properties of quinoline alkaloids have been investigated to a limited degree and as a result evidence of cytotoxic, phototoxic, mutagenic, antibacterial and anti-viral (HIV) activity has been observed. Individual presentations on various aspects of quinoline alkaloids have also appeared as book chapters or articles in journals. These constituents have attracted considerable interest due to their biological activity but only few publications have appeared on the spectral features of chemical constituents of the plant S. laureola.
Molecules Manuscript ID: alkaloids-20071204-Andraos-ca
Type of the paper: Review
Title: A Critical Appraisal of Various Total Syntheses of the Woodward Alkaloids with Respect to Green Chemistry Metrics
Authors: John Andraos
York University, Department of Chemistry, 4700 Keele Street, Toronto, ON M3J 1P3, CANADA
E-mail: jandraos@yorku.ca
Abstract: This review gives a thorough up-to-date green metrics evaluation of the state-of-the-art in the achievement of total syntheses of the celebrated Woodward alkaloids quinine, lysergic acid, morphine, strychnine, reserpine, and colchicine by various research groups with respect to material efficiency and synthesis strategy parameters. In particular, synthesis plans are evaluated with respect to atom economy (AE), reaction mass efficiency (RME), molecular weight building up parameter, degree of convergence and degree of asymmetry using the synthesis tree algorithm. Simple template spreadsheet programs are introduced to calculate these parameters for linear and convergent plans using number of steps, number of input reagents, reaction yields and molecular weights of reagents, intermediates, and byproducts as the only input data. New concepts are introduced in this work which give a deeper understanding of synthesis strategy and design, namely hypsicity (oxidation level)
index, structure mapping, and fraction of sacrificial reagents.
Key references: Andraos, J. Org. Process Res. Develop. 2005, 9, 149
Andraos, J. Org. Process Res. Develop. 2005, 9, 404
Andraos, J. Org. Process Res. Develop. 2006, 10, 212
Andraos, J. Application of Green Metrics Analysis to Chemical Reactions and
Synthesis Plans in Green Chemistry Metrics (A. Lapkin and D.C. Constable, eds.)
Blackwell Scientific: Oxford, in press
Molecules Manuscript ID: alkaloids-20071206-Mauer-de
Type of the paper: Review
Tentative Title: Analysis of Toxic Alkaloids in Bodysamples
Authors: Dr. Jochen Beyer, Prof. Dr. Olaf Drummer and Prof.Dr.Dr.h.c. Hans H. Maurer
E-mails: jochenb@vifm.org, olaf@vifm.org, hans.maurer@uniklinikum-saarland.de
Molecules Manuscript ID: alkaloids-20071214-vandereycken-be
Type of the paper: Review
Title: An Overview of the Synthesis of Alkaloids and Alkaloid Analogues Bearing a 5,6,7,8-Tetrahydrodibenz[c,e]azocine Skeleton
Authors: Prasad Appukkuttan and Erik Van der Eycken*
E-mail: erik.vandereycken@chem.kuleuven.be, darpas@gmail.com
Abstract: During the last two decades Amarallydaceae alkaloids have attracted extensive interest in both synthetic organic and pharmaceutical chemistry, primarily due to the amazing structural diversity presented by these natural products. The name Amarallydaceae originated from the word Amaryllis, the name of a Greek shepherdess, and the plant extracts containing these alkaloids, were used for treating a variety of ailments as well as to induce hallucinations. Apogalanthamine, Buflavine and Aza-Steganacin analogues belonging to the Amarallydaceae alkaloid family feature a unique 5,6,7,8-tetrahydrodibenz[c,e]azocine skeleton, a biaryl subunit with a fused eight-membered ring-system bearing a nitrogen atom on the benzylic position with respect to the lower aromatic ring. These compound classes have raised significant attention i.a. due to their potent anti-serotonin, immunosuppressive and anti-tumor activities. In this contribution, we will provide a comprehensive overview of the synthesis of these alkaloids and their structural analogues bearing a 5,6,7,8-tetrahydrodibenz[c,e]azocine skeleton. We will cover both the early synthetic efforts as well as the recent developments on the synthesis of these fascinating alkaloid analogues, focusing mainly on Apogalanthamine, Buflavine, Steganacin- and Steganone-7-aza analogues.
Molecules Manuscript ID: alkaloids-20071219-Hattori-jp
Type of the paper: Review
Tentative Title: Pharmacology and pharmacokinetics of Berberine
Authors: Feng Zuo, Chao-Mei Ma, Masao Hattori*
Affiliation: Department of Pharmacology, National Engineering Research Center for R&D of TCM Multi-ingredient Drugs, Beijing 100075, PR China; Institute of Natural Medicine, University of Toyama, Toyama 930-0194, Japan; Fax: 86-10-87632617,
E-mails: zuofeng1229@hotmail.com, saibo421@inm.u-toyama.ac.jp
Abstract: Berberine (Ber) is an isoquinoline alkaloid of the protoberberine-type, with a long history of medicinal use in traditional eastern medicine. It is found in the roots, rhizomes and stem bark of many plant species, such as Coptis chinensis Franch., Coptis japonica Makino., Berberis thunbergii DC., Hydrastis canadensis L. and Thalictrum lucidum Ait.. Berberine extracts and decoctions have significant antimicrobial activities. Recent pharmacological studies have demonstrated that Ber also possesses antitumor, anti-HIV, antifungal, cardio-protective, immunoregulative, antimalarial, anti-inflammatory, anti-oxidative, cerebri-protective, antimutagenic, vasorelaxing, anxiolytic, antihyperglycaemic, analgesic, hepato-protective, antidepressant, ameliorating the spatial memory impairment of Alzheimer’ Disease and antihypercholesterolemic effects. The pharmacokinetics study of Ber have been examined by several investigators using a tritiated derivative or HPLC in early, because the plasma concentrations were very low, Ber was always thought to be poorly absorbed through the gut wall. In recent years, with the development of LC/MS-MS, the researchers have investigated the disposition process of Ber in vivo. There are four main metabolites, which were identified as berberrubine (M1), thalifendine (M2), demethyleneberberine (M3) and jatrorrhizine (M4), together with their respective glucuronide-conjugates using LC/MS-MS with an electrospray ionization (ESI) in rat plasma after oral Ber administration. Ber was absorbed quickly and great from gastrointestine, and metabolized rapidly in liver, and then the metabolites undertook the enterohepatic circulation through intestinal flora. Although the concentration of Ber was very low in the plasma, the metabolites remained a long time with high amount in the body, so these metabolites might be active components of Ber, as indicated by the range of pharmacological effects in vivo.
