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 cancer 1 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 pseudonarcissus 14 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

Novel Lycorine Derivatives as Anticancer Agents: Synthesis and In Vitro Biological Evaluation

“…Many of these plants have been used historically for the treatment of cancer, since the oil of the daffodil Narcissus poeticus L. was used by Hippocrates of Kos [5]. The application of narcissus oil in cancer management continued during the middle ages in China, North Africa and Central America [6]. The major components isolated from the Amaryllidaceae plant family are alkaloids.…”

Effect of Rosehip (<i>Rosa Canina</i>) Extracts on Human Brain Tumor Cell Proliferation and Apoptosis

“…Despite recent advances in chemotherapy, radiotherapy and surgical interventions, the clinical outcome of GBMs is poor and a better understanding of glioma biology is needed in order to develop better therapeutic options. Recent studies have investigated the anti-oncogenic properties of natural products and several of these studies have shown that natural product extracts exhibit anti-oncogenic properties against various types of cancer [3][4][5][6][7]. Specifically, there has been a renewed effort to examine the anti-oncogenic properties of natural products for the treatment of GBM cells [8][9][10][11][12][13].…”

Phytochemistry and Pharmacology of Genus Zephyranthes

“…treatment of diabetes, for ear and chest ailments and against viral infections. Traditional usage of this genus from very simple health problems like head ache, cough and cold, boils to very complicated diseases like breast cancer, tuberculosis, rheumatism, tumors shows its importance in treatment of various diseases [2,11,12].…”