Showing papers on "Amaryllidaceae Alkaloids published in 2008"

Chemistry, biology, and medicinal potential of narciclasine and its congeners.

Abstract: Ornamental flower growers know that placing a cut daffodil (a.k.a. narcissus) in a vase with other flowers has a negative effect on the quality of those flowers and significantly shortens their vase life. Furthermore, a common horticultural practice for the cultivation of narcissus flowers involves the introduction of cuts on the bulbs before immersing them into water. The mucilage that leaches out from the cuts is constantly removed by frequent changing of water and this leads to sprouting. These observations raise speculation that specific components in the mucilage of the narcissus bulbs may have powerful growth-inhibitory effects. Historical use of narcissus flowers, as well as at least thirty other plants of the Amaryllidaceae family, in folk medicine for the management of cancer1 speaks volumes to validate this conjecture. Indeed, powerful anticancer properties of Narcissus poeticus L. were already known to the Father of Medicine, Hippokrates of Kos (ca. B.C. 460–370), who recommended a pessary prepared from narcissus oil for the treatment of uterine tumors.2 His successors, the ancient Greek physicians Pedanius Dioscorides (ca. A.D. 40–90) and Soranus of Ephesus (A.D. 98–138) continued using this therapy in the first and second centuries A.D.3,4 In addition, the topical anticancer uses of extracts from this plant5,6 as well as from N. pseudonarcissus7–9 were recorded in the first century A.D. by the Roman natural philosopher Gaius Plinius Secundus, (A.D. 23–79), better known as Pliny the Elder.10 Even the Bible provides multiple references to the Mediterranean N. tazetta L., which has a long history of use against cancer.11 The applications of narcissus oil in cancer management continued in the middle ages in Chinese, North African, Central American and Arabian medicine.1,12 The uses of other genera of the Amaryllidaceae family were also common, e. g. Hymenocallis caribaea (L. emend Gawler) Herbert, utilized by early European medical practitioners for inflammatory tumors.13 More recently, the plants of the Amaryllidaceae have been under intense scrutiny for the presence of the specific metabolites responsible for the medicinal properties associated with this plant family. The study began in 1877 with the isolation of alkaloid lycorine from Narcissus pseudonarcissus14 and since then more than 100 alkaloids, exhibiting diverse biological activities, have been isolated from the Amaryllidaceae plants. Based on the present scientific evidence, it is likely that isocarbostyril constituents of the Amaryllidaceae, such as narciclasine, pancratistatin and their congeners, are the most important metabolites responsible for the therapeutic benefits of these plants in the folk medical treatment of cancer. Notably, N. poeticus L. used by the ancient Greek physicians, as was eluded before, is now known to contain some 0.12 g of narciclasine per kg of fresh bulbs.15 Continuing along this intriguing path, the focus of the present review is a comprehensive literature survey and discussion of the chemistry and biology of these compounds as specifically relevant to their potential use in medicine. The examination of the synthetic organic chemistry, more specifically the total synthesis efforts inspired by the challenging chemical structures of narciclasine, pancratistatin and their congeners, will be reduced to a minimum in view of the two very recent excellent reviews published on this subject.16,17

Analysis of galanthamine-type alkaloids by capillary gas chromatography–mass spectrometry in plants

Abstract: Galanthamine, an acetylcholinesterase inhibitor used for the treatment of Alzheimer's disease, and galanthamine-type alkaloids are synthesised in different plants of the family Amaryllidaceae. A capillary gas chromatographic-mass spectroscopic (CGC-MS) method for the separation of 7 galanthamine type alkaloids, including galanthamine and epigalanthamine, is described in the present paper. A simple method for the routine quantification of galanthamine in plants was developed using pre-packed columns with diatomaceous earth (Isolute HM-N), allowing simultaneous preparation of a large number of samples. Galanthamine showed excellent linearity in the range from 50 to 1000 microg/mL and the limit of quantification was 5 microg/mL in total ion current mode and 1.6 ng/mL in selected ion monitoring mode. The recovery of galanthamine was more than 90%. Interday reproducibility (RSD) of the extraction was 2.74%. A method to find and to microextract Amaryllidaceae alkaloids in low-mass plant samples is also described.

First Total Synthesis of (±)-Powelline

Abstract: The first total synthesis of (±)-powelline is reported in 10% overall yield over eight steps using an intramolecular oxidative phenolic coupling reaction as the key reaction.