Another two novel ceramides from Zephyranthes candida

Wu, Zhiyong; Chen, Yu; Xu, Feng; Xia, Bing; Wang, Ming; Dong, Yang

doi:10.1007/s10600-010-9564-y

Cited by 4 publications

(4 citation statements)

References 16 publications

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“…The whole plants of Z. candida are used to treat infantile convulsions, epilepsy, and tetanus. 2 Previous phytochemical studies on Z. candida have focused on the bulbs, leading to reports of four ceramides 3,4 and nine alkaloids. 5–9 Among these, trans -dihydronarciclasine was obtained as a cytostatic agent with an IC 50 value of 3.2 ng/mL.…”

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“…The whole plants of Z. candida are used to treat infantile convulsions, epilepsy, and tetanus . Previous phytochemical studies on Z. candida have focused on the bulbs, leading to reports of four ceramides , and nine alkaloids. − Among these, trans -dihydronarciclasine was obtained as a cytostatic agent with an IC 50 value of 3.2 ng/mL . Expecting the other plant parts to be chemically distinct from the previously well-studied bulbs, the whole plant extract of Z. candida was investigated, leading to the isolation of seven new alkaloids, compounds 1 and 5 – 10 , and eight known alkaloids ( 2 – 4 , 11 – 15 ).…”

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Cytotoxic Alkaloids from the Whole Plants of Zephyranthes candida

et al. 2012

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Seven new alkaloids, N-methylhaemanthidine chloride (1), N-methyl-5,6-dihydroplicane (5), O-methylnerinine (6), N-ethoxycarbonylethylcrinasiadine (7), N-ethoxycarbonylpropylcrinasiadine (8), N-phenethylcrinasiadine (9) and N-isopentylcrinasiadine (10), together with eight known alkaloids, haemanthamin (2), 3-epimacronine (3), (+)-tazettine (4), N-methylcrinasiadine (11), trisphaeridine (12), 5,6-dihydrobicolorine (13), lycorine (14), and nigragillin (15), were isolated from the whole plants of Zephyranthes candida. The structures of the new compounds were established by spectroscopic data interpretation, with single-crystal X-ray diffraction analysis performed on 1. The absolute configuration of 3-epimacronine (3) was determined by single-crystal X-ray diffraction analysis with CuKα irradiation. Compounds 1–15 were evaluated for their in vitro cytotoxicity against five human cancer cell lines and the Beas-2B immortalized (non-cancerous) human bronchial epithelial cell line. Compounds 1, 2, 9, and 14 exhibited cytotoxicity with IC50 values ranging from 0.81 to 13 μM with selectivity indices as high as 10 when compared to the Beas-2B cell line.

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Cytotoxic Alkaloids from the Whole Plants of Zephyranthes candida

et al. 2012

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“…In comparison, the most abundant compounds were b-sitosterol (200) (207 mg) and lycorine (1) (79 mg) (Wu et al 2009b). Another four new ceramides (196)(197)(198)(199) were reported by the same group while scaling up the primary quantity to 3.5 kg (Wu et al 2009a) and 10.2 kg (Wu et al 2010).…”

Section: Brown 1968amentioning

confidence: 98%

Specialized metabolites of the genus Zephyranthes Herb.: a critical review on taxonomy and phytochemistry

Šafratová,

Vrabec,

Blunden

et al. 2024

Phytochem Rev

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This article is a critical review of the taxonomy and phytochemistry of the genus Zephyranthes Herb., a group of plants known for their beautiful flowers and traditional medicinal uses. The present review summarizes the occurrence, isolation, and identification of specialized metabolites, which have recently been frequently studied because of their important biological activities. Among the accepted 203 species, only 27 have been phytochemically investigated. This paper provides an overview of the different types of specialized metabolites identified in these plants and considers problematic taxonomic evolution within this species. The differences between two internationally recognized databases, which classify only 41% of the species in the same way, are briefly summarized. In addition, there are many reports on their metabolites, especially alkaloids, but some of the data in the literature are occasionally inaccurate and sometimes even erroneous. This critical review aims to discuss, summarize, and evaluate up-to-date (up to July of 2023) information about metabolites of the genus Zephyranthes, focusing on phytochemistry and taxonomy. Graphical abstract

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“…In 1980s Pettit et al, and Ghosal et al, reported alkaloids, pancratistatin, (+)-epimaritidine, crinamine and haemanthamine, maritidine, ungeremine, criasbetaine, zefbetaine, zeflabetaine, alkaloidal phospholipids, two lactam alkaloid, three glucosyloxy alkaloid; flavans, 7-hydroxy-3',4'-methylenedioxyflavan and its glycoside, 7,4'-dihydroxy-3'-methoxyflavan and 7-methoxy-2'-hydroxy-4',5'-methylenedioxyflavan from bulbs and flowers of different species [28][29][30][31][32] 3-epimacronine, N-methylcrinasiadine, trisphaeridine, 5,6-dihydrolycorine, nigragillin, 2-hydroxy albomaculine, 6α-hydroxyhippeastidine, 10-deoxy-6α-hydroxyhippeastidine, 6β-hydroxyhippeastidine, 7-hydroxy-3',4'-methylenedioxyflavan 7-hydroxy-3',4'-methylenedioxyflavan and its glycoside, 7,4'-dihydroxy-3'-methoxyflavan and 7-methoxy-2'-hydroxy-4',5'-methylenedioxyflavan, maritidine, 2-O-glycerophosphoryllycorine, phosphatidyllycorines, phosphatidylpseudolycorines, phosphatidyllycoriniium methocation, 2-oxy phenanthridinium, zefbetaine, zeflabetaine, crinamine, haemanthamine, lycorine, pseudolycorine, narciclassine, protorimine, kalbreclassine, lycorine-1-O-β-D-glucoside, pseudolycorine-1-O-β-Dglucoside, criasbetaine, ungeremine [29,30] [39][40][41]. During this decade flavans, sterols were also reported from the same species [39].…”

Section: Traditional Usagementioning

confidence: 99%