Phenol oxidation and biosynthesis. Part IX. The biosynthesis of norpluviine and galanthine

Kirby, G. W.; Tiwari, H. P.

doi:10.1039/j39660000676

Cited by 18 publications

(11 citation statements)

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“…Benzylamine O -methylnorbelladine ( 9 ) was also shown to be a precursor of norpluviine ( 27 ), which is known to be integral to lycorine-type alkaloid metabolization [28]. Apart from this, the transformation of caranine ( 5 ) into lycorine ( 15 ) has been observed in both Zephyranthes candida and Clivia miniata [29,30].…”

Section: Resultsmentioning

confidence: 99%

Alkaloid Constituents of the Amaryllidaceae Plant Amaryllis belladonna L

et al. 2017

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The plant family Amaryllidaceae is well-known for its unique alkaloid constituents, which exhibit a wide range of biological activities. Its representative, Amaryllis belladonna, has a geographical distribution covering mainly southern Africa, where it has significant usage in the traditional medicine of the native people. In this study, A. belladonna samples collected in Brazil were examined for alkaloid content. Alkaloid profiles of A. belladonna bulbs were generated by a combination of chromatographic, spectroscopic and spectrometric methods, including GC–MS and 2D NMR. In vitro screening against four different parasitic protozoa (Trypanosoma cruzi, T. brucei rhodesiense, Leishmania donovani and Plasmodium falciparum) was carried out using the A. belladonna crude methanol extract, as well as three of its alkaloid isolates. Twenty-six different Amaryllidaceae alkaloids were identified in the A. belladonna bulb samples, and three of them were isolated. Evidence for their respective biosynthetic pathways was afforded via their mass-spectral fragmentation data. Improved data for 1-O-acetylcaranine was provided by 2D NMR experiments, together with new 1H-NMR data for buphanamine. The crude extract and 3-O-acetylhamayne exhibited good antiprotozoal activity in vitro, although both with a high cytotoxic index.

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Section: Resultsmentioning

confidence: 99%

Alkaloid Constituents of the Amaryllidaceae Plant Amaryllis belladonna L

et al. 2017

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“…This mechanism is supported by the studies involving appropriately labelled precursors. [88][89][90] Lycorine is the precursor of hippeastrine (10) and the plausible intermediates are 62 and 63 ( Figure 11).…”

Section: Biosynthesis Of Amaryllidaceae Alkaloidsmentioning

confidence: 99%

Chemistry, Biology, and Medicinal Potential of Narciclasine and its Congeners

2008

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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

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“…In the conversion of O-methylnorbelladine (87) into lycorine (1), the labeling position [3-3 H] on the aromatic ring of L-tyr afterward appears at C-2 of norpluviine (12), which is formed as an intermediate, the configuration of the tritium apparently being b (176). This tritium is retained in subsequently formed lycorine (1), which means that hydroxylation at C-2 proceeds with an inversion of configuration (188) by a mechanism involving an epoxide, with ring opening followed by allylic rear rangement of the resulting alcohol (Fig.…”

Section: Lycorine and Homolycorine Typesmentioning

confidence: 99%