Four New Crinine-Type Alkaloids from Sternbergia Species

Pabuççuoğlu, Varol; Richomme, Pascal; Gözler, Tekant; Kıvçak, Bijen; Freyer, Alan J.; Shamma, Maurice

doi:10.1021/np50064a020

Cited by 54 publications

(31 citation statements)

References 7 publications

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“…Although the enantiomeric forms of noroxomaritidine have not been isolated, assays suggest a preference of NR for one of these forms. Depending on the enantiomer being reduced this activity could contribute to the biosynthesis of either maritinamine or elwesine (32,33). Both of these compounds share a reduced carbon-carbon double bond, but are derived from the (10bR,4aS)-noroxomaritidine and (10bS,4aR)-noroxomaritidine skeletons, respectively.…”

Section: Discussionmentioning

confidence: 99%

Identification of a Noroxomaritidine Reductase with Amaryllidaceae Alkaloid Biosynthesis Related Activities

Kilgore

Holland

Jez

et al. 2016

Journal of Biological Chemistry

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Amaryllidaceae alkaloids are a large group of plant natural products with over 300 documented structures and diverse biological activities. Several groups of Amaryllidaceae alkaloids including the hemanthamine-and crinine-type alkaloids show promise as anticancer agents. Two reduction reactions are required for the production of these compounds: the reduction of norcraugsodine to norbelladine and the reduction of noroxomaritidine to normaritidine, with the enantiomer of noroxomaritidine dictating whether the derivatives will be the crinine-type or hemanthamine-type. It is also possible for the carbon-carbon double bond of noroxomaritidine to be reduced, forming the precursor for maritinamine or elwesine depending on the enantiomer reduced to an oxomaritinamine product. In this study, a short chain alcohol dehydrogenase/reductase that co-expresses with the previously discovered norbelladine 4-Omethyltransferase from Narcissus sp. and Galanthus spp. was cloned and expressed in Escherichia coli. Biochemical analyses and x-ray crystallography indicates that this protein functions as a noroxomaritidine reductase that forms oxomaritinamine from noroxomaritidine through a carbon-carbon double bond reduction. The enzyme also reduces norcraugsodine to norbelladine with a 400-fold lower specific activity. These studies identify a missing step in the biosynthesis of this pharmacologically important class of plant natural products.

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Section: Discussionmentioning

confidence: 99%

Identification of a Noroxomaritidine Reductase with Amaryllidaceae Alkaloid Biosynthesis Related Activities

Kilgore

Holland

Jez

et al. 2016

Journal of Biological Chemistry

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“…18 NMR data for the known alkaloids described herein closely matched those reported elsewhere. [18][19][20][21][22][23][24][25][26] Mass spectra were deconvoluted using AMDIS 2.64 software (NIST) (WA, USA) and RIs recorded using a standard n-hydrocarbon calibration mixture (C9-C36). The proportion of individual components in the alkaloid fractions are expressed as a percentage of total alkaloid content.…”

Section: Identification Of Alkaloids By Cgc-msmentioning

confidence: 99%

“…Phytochemical procedure and NMR data of haemanthamine N-oxide (1) In the course of the phytochemical procedure, the known Amaryllidaceae alkaloids haemanthamine (16), 19,23 Table 3 shows measured m/z values, mass error (ppm), DBE and molecular formula of the main compounds detected by the LS(+)-MS technique, where 10 and 8 species were identified in bulb and leaf, respectively. The ions of m/z 302, 318, 320, 332 and 348 are the most abundant species found, having double bond equivalents (DBEs) of 7-9.…”

Section: Cgc-ms Dereplicationmentioning

confidence: 99%

Identification of Alkaloids from Hippeastrum aulicum (Ker Gawl.) Herb. (Amaryllidaceae) Using CGC-MS and Ambient Ionization Mass Spectrometry (PS‑MS and LS-MS)

Bessa

Andrade

Domingos

et al. 2016

J. Braz. Chem. Soc.

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Amaryllidaceae alkaloids are well-known isoquinolines which have demonstrated a wide range of biological activities such as antiviral, anticancer, acetylcholinesterase inhibition, antimalarial, among others. Mass spectrometry (MS) studies based on capillary gas chromatography (CGC), paper spray (PS), and leaf spray (LS) ionization were carried out for alkaloid investigation of the native Brazilian species Hippeastrum aulicum, along with nuclear magnetic resonance (NMR) techniques. Thirty-one alkaloids were identified including the new compound haemanthamine N-oxide. The results from PS-and LS-MS techniques were consistent with those observed in CGC-MS analysis. To the best of our knowledge, it is the first study combining NMR, CGC-MS and the ambient ionization-mass spectrometry (PS-and LS-MS) on Amaryllidaceae plants.

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“…The presence of α -ethanobridge in addition to the quasi-axial β -oriented disposition of the C-3 hydroxyl were deduced from the coupling constants, J 2, 3 = 5, J 3, 4 α =small undetetectable and the absence of allylic coupling between H-1 and H-3 (13). The large coupling between H-4a and H-4α (12.7 Hz) proves their trans/diaxial position characteristic for the haemanthamine series series (14-16). Each of the protons H-11 α , H-11 β , H-12 α and H-12 β is observed as ddd or m, which indicates a non-substituted ethanobridge (17).…”

Section: Resultsmentioning

confidence: 75%

Phytochemical and Biological Investigation of Narcissus pseudonarcissus Cultivated in Egypt

Shawky

Hammoda

Donia

et al. 2018

Records of Pharmaceutical and Biomedical Sciences

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Amaryllidaceae is a well-known family for its high alkaloidal content. These alkaloids comprise a unique group of bases that have been found to occur in this family. The Amaryllidaceae alkaloids represent a large and still expanding group of isoquinoline alkaloids, the majority of which are not known to occur in any other family of plants. This article reports on the phytochemical investigation of the alkaloidal content of the flowers of clivia nobilis cultivated in Egypt which resulted in the isolation of four alkaloids; lycorine with pyrrolo{de}phenanthridine nucleus (lycorine-type) which is the common alkaloid of the amaryllidaceae family, clivatine and nobilisine, both with [2]benzopyrano (3,4-g) indole nucleus (lycorenine-type) and (+) 8-O-demethylmaritidine with 5,10b-ethanophenanthridine nucleus (crinine-type). Furthermore, the antimicrobial activity of the chloroform extract of the flowers of c. nobilis along with some of the isolated alkaloids has been studied.

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Four New Crinine-Type Alkaloids from Sternbergia Species

Abstract: ABsrFucT.-"he crinine-type alkaloids (+)-buphanisine [l] and (-)-siculine E21 have been obtained from Sternbwgia sicula, while (-)-epimaritinarnine 131 and (-kmaritinarnine [4]were found in Sternbergia lutea.

Cited by 54 publications

References 7 publications

Identification of a Noroxomaritidine Reductase with Amaryllidaceae Alkaloid Biosynthesis Related Activities

Identification of a Noroxomaritidine Reductase with Amaryllidaceae Alkaloid Biosynthesis Related Activities

Identification of Alkaloids from Hippeastrum aulicum (Ker Gawl.) Herb. (Amaryllidaceae) Using CGC-MS and Ambient Ionization Mass Spectrometry (PS‑MS and LS-MS)

Phytochemical and Biological Investigation of Narcissus pseudonarcissus Cultivated in Egypt

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