Cripowellin A and B, a novel type of amaryllidaceae alkaloid from Crinum powellii

Velten, Robert; Erdelen, Christoph; Gehling, Matthias; Göhrt, Axel; Gondol, Daniel; Lenz, J.; Lockhoff, Oswald; Wachendorff, Ulrike; Wendisch, Detlef

doi:10.1016/s0040-4039(98)00057-4

Cited by 35 publications

(28 citation statements)

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“…Optical rotations of cripowellins A and B matched the published values, 7 and the measured optical rotations for cripowellins C and D were very similar to those of cripowellins A and B. This observation combined with the NOESY data provided evidence to support the indicated stereochemistry for cripowellins C and D. To further support this claim ECD spectra were obtained on cripowellins A – D in methanol and it was observed that all four compounds had very similar spectra.…”

Section: Resultssupporting

confidence: 77%

“…7 The structure of 2 (Figure 1) was elucidated as the known compound cripowellin B from the HRESIMS data ( m/z 524.2127 [M+H] + , calcd for C 25 H 34 NO 11 + , 524.2126) and comparison of its 1 H NMR data (Table 1) to the published literature values. 7 Both 1 and 2 possessed an intense fragment in their HRESIMS data at 320.1119 m/z, corresponding to the [Aglycone+H] + fragment.…”

Section: Resultsmentioning

confidence: 98%

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New potently bioactive alkaloids from Crinum erubescens

Presley

Krai

Dalal

et al. 2016

Bioorganic & Medicinal Chemistry

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Antimalarial bioassay-guided fractionation of the swamp lily Crinum erubescens led to the isolation of four compounds with potent antiplasmodial activity. Compounds 1 and 2 were determined from their spectroscopic data to be the known pesticidal compound cripowellin A and the known pesticidal and antiproliferative compound cripowellin B. 1D and 2D-NMR techniques were used to determine the identities of 3 and 4 as the new compounds cripowellin C and D. A fifth compound was identified as the known alkaloid hippadine, which was inactive against Plasmodium falciparum. The antiplasmodial IC50 values of compounds 1 – 4 were determined to be 30 ± 2, 180 ± 20, 26 ± 2, and 260 ± 20 nM, respectively, and their antiproliferative IC50 values against the A2780 human ovarian cancer cell line were 11.1 ± 0.4, 16.4 ± 0.1, 25 ± 2, and 28 ± 1 nM.

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Section: Resultssupporting

confidence: 77%

Section: Resultsmentioning

confidence: 98%

New potently bioactive alkaloids from Crinum erubescens

Presley

Krai

Dalal

et al. 2016

Bioorganic & Medicinal Chemistry

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“…In 1997 researchers at Bayer AG reported on two new Amaryllidaceae alkaloids,1 cripowellins A ( 1 ) and B ( 2 ), which had been isolated from the bulbs and roots of Crinum powellii , a popular ornamental plant in Europe 2. 3 The two compounds differ only in their glycosidic parts. The assumption that both of these sugar moieties are derived biogenically from β‐ D ‐glucose accounts for the depicted absolute stereochemistry.…”

Section: Methodsmentioning

confidence: 99%

Asymmetric Synthesis of the 1‐epi Aglycon of the Cripowellins A and B

2005

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The unusual [5.3.2]bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellins A and B has been synthesized for the first time by a sequence of Sharpless dihydroxylation, ring‐closing metathesis (RCM), and intramolecular Heck reaction (see scheme). The asymmetric synthesis of the 1‐epi aglycon proceeds with virtually complete diastereo‐ and enantioselectivity (≥98 % de, ≥98 % ee) in 13 steps and an overall yield of 5.6 %.

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“…Another reaction of special mechanistic interest occurs during the biosynthesis of cripowellin. The cripowellin skeleton was discovered in 1998 in Crinum powellii and resembles a highly oxidized version of the haemanthamine skeleton that has had the 10b-4a carbon-carbon bond severed and replaced with a ketone on the 4a position (Velten et al, 1998) (see Figure 3 for structure). If this is the pathway for generating this alkaloid, it is possible that carbon bond cleavage leading to the formation of a ketone is catalyzed by a cytochrome P450 similar to secologanin synthase that converts loganin into secologanin in an analogous manner with a ketone product (Irmler et al, 2000).…”

Section: Amaryllidaceae Alkaloidsmentioning

confidence: 99%

The Amaryllidaceae alkaloids: biosynthesis and methods for enzyme discovery

Kilgore

Kutchan

2015

Phytochem Rev

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Amaryllidaceae alkaloids are an example of the vast diversity of secondary metabolites with great therapeutic promise. The identification of novel compounds in this group with over 300 known structures continues to be an area of active study. The recent identification of norbelladine 4′-O-methyltransferase (N4OMT), an Amaryllidaceae alkaloid biosynthetic enzyme, and the assembly of transcriptomes for Narcissus sp. aff. pseudonarcissus and Lycoris aurea highlight the potential for discovery of Amaryllidaceae alkaloid biosynthetic genes with new technologies. Recent technical advances of interest include those in enzymology, next generation sequencing, genetic modification, nuclear magnetic resonance spectroscopy (NMR), and mass spectrometry (MS).

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Cripowellin A and B, a novel type of amaryllidaceae alkaloid from Crinum powellii

Cited by 35 publications

References 1 publication

New potently bioactive alkaloids from Crinum erubescens

New potently bioactive alkaloids from Crinum erubescens

Asymmetric Synthesis of the 1‐epi Aglycon of the Cripowellins A and B

The Amaryllidaceae alkaloids: biosynthesis and methods for enzyme discovery

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