Occurrence of non-basic metabolites in Amaryllidaceae

Piozzi, Franco; Marino, Maria Luisa; Fuganti, Claudio; Martino, Andrea

doi:10.1016/s0031-9422(00)85963-4

Cited by 37 publications

(24 citation statements)

References 3 publications

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“…Narciclasine is crystallized from acetic acid (Evidente 1991). When this procedure was applied to S. lutea Ker-Gawl bulbs, narciclasine was obtained in higher yield (20 mg/kg) than that (\5 mg/kg) obtained using the classical ethanolic extraction method (Evidente 1991;Piozzi et al 1969). A study to completely assign …”

Section: Lycorine Derivativesmentioning

confidence: 95%

Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives

Evidente

Kornienko

2009

Phytochem Rev

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Plants of the Amaryllidaceae family have been under intense scrutiny for the presence of the specific metabolites responsible for the medicinal properties associated with them. The study began in 1877 with the isolation of alkaloid lycorine from Narcissus pseudonarcissus 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 plant species in the folk medical treatment of cancer. Notably, Narcissus poeticus L., used by the ancient Greek physicians, is now known to contain about 0.12 g of narciclasine per kg of fresh bulbs. The focus of the present research work is the chemistry and biology of these compounds as specifically relevant to their potential use in medicine. In particular, the anticancer evaluation of lycorine, narciclasine as well as of other Amaryllidaceae alkaloids and their synthetic derivatives are presented in this paper. The structure-activity relationships among some groups of Amaryllidaceae alkaloids will be discusse

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Section: Lycorine Derivativesmentioning

confidence: 95%

Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives

Evidente

Kornienko

2009

Phytochem Rev

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“…In the fourth century BC, Hippocrates of Cos (the 'Father of Medicine') recommended a pessary prepared from Narcissus oil (probably N. poeticus) for the management of uterine tumors (388). It is now known that N. poeticus contains 0.012% of the antineoplastic agent narciclasine (68) in the fresh bulb (14,101). It is now known that N. poeticus contains 0.012% of the antineoplastic agent narciclasine (68) in the fresh bulb (14,101).…”

Section: Traditional Medicinal Usagementioning

confidence: 99%

Chapter 3 Chemical and Biological Aspects of Narcissus Alkaloids

Bastida

Lavilla

Viladomat

2006

The Alkaloids: Chemistry and Biology

182

273

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“…However, information regarding the allelopathic activity in the field and in laboratory studies is limited (Lallemand et al 2009). Narciclasine (NCS) is a bioactive secondary metabolite (Amaryllidaceae alkaloid) isolated from Narcissus tazetta bulbs and also widely exists in the genera Galanthus, Haemanthus, Leucojum, Pancratium, Sprekelia, Sternbergia and Vallota (Piozzi et al 1969). Previous studies showed that NCS possesses antimitotic (Ceriotti 1967), antiviral functions (Gabrielsen et al 1992) and antitumor activities (Lefranc et al 2009).…”

Section: Introductionmentioning

confidence: 99%

Narciclasine, a potential allelochemical, affects subcellular trafficking of auxin transporter proteins and actin cytoskeleton dynamics in Arabidopsis roots

et al. 2015

Planta

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The present study documented the action of a potential allelochemical, narciclasine, on auxin transport in Arabidopsis by mainly affecting subcellular trafficking of PIN and AUX1 proteins and through interfering actin cytoskeletal organization. Narciclasine (NCS), an Amaryllidaceae alkaloid isolated from Narcissus tazetta bulbs, has potential allelopathic activity and affects auxin transport. However, little is known about the cellular mechanism of this inhibitory effect of NCS on auxin transport. The present study characterizes the effects of NCS at the cellular level using transgenic Arabidopsis plants harboring the promoters of PIN, in combination with PIN-GFP proteins or AUX1-YFP fusions. NCS treatment caused significant reduction in the abundance of PIN and AUX1 proteins at the plasma membrane (PM). Analysis of the subcellular distribution of PIN and AUX1 proteins in roots revealed that NCS induced the intracellular accumulation of auxin transporters, including PIN2, PIN3, PIN4, PIN7 and AUX1. However, other PM proteins, such as PIP2, BRI1, and low temperature inducible protein 6b (LTI6b), were insensitive to NCS treatment. NCS-induced PIN2 compartments were further defined using endocytic tracer FM 4-64 labeled early endosomes and suggested that this compound affects the endocytosis trafficking of PIN proteins. Furthermore, pharmacological analysis indicated that the brefeldin A (BFA)-insensitive pathway is employed in the cellular effects of NCS on PIN2 trafficking. Although NCS did not alter actin dynamics in vitro, it resulted in the depolymerization of the actin cytoskeleton in vivo. This disruption of actin filaments by NCS subsequently influences the actin-based vesicle motility. Hence, the elucidation of the specific role of NCS is useful for further understanding the mechanisms of allelopathy at the phytohormone levels.

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Occurrence of non-basic metabolites in Amaryllidaceae

Cited by 37 publications

References 3 publications

Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives

Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives

Chapter 3 Chemical and Biological Aspects of Narcissus Alkaloids

Narciclasine, a potential allelochemical, affects subcellular trafficking of auxin transporter proteins and actin cytoskeleton dynamics in Arabidopsis roots

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