Stability of protoanemonin in plant extracts from Helleborus niger L. and Pulsatilla vulgaris Mill.

Müller, Melanie; Bertrams, Julia; Stintzing, Florian C.

doi:10.1016/j.jpba.2020.113370

Cited by 10 publications

(9 citation statements)

References 21 publications

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Section: Discussionmentioning

confidence: 99%

“…The Christmas Rose (H niger L.) 1 belongs to the subspecies Helleborus of the Ranunculaceae family and its rhizome and roots contain numerous medicinally active ingredidents [4][5][6][7] including potent cardiac glycosides, which possess similar pharmacological properties to those of the Digitalis glycosides. [12][13][14] Recently, we published a practical extraction method of ( + )-ranucoside 1 from the leaves of cultivated H niger L. plants and confirmed the structure by 500 MHz NMR spectroscopy and X-ray structure analysis.…”

Section: Discussionmentioning

confidence: 99%

“…Rhizome and roots (Radix Hellebori nigri) are used as medicine in allopathy and homeopathy. 3 Furthermore, pharmacological studies revealed that the root extracts contain numerous medicinally active ingredients [4][5][6][7] as well as the powerful cardiac glycoside hellebrin [8][9][10][11] which possesses similar pharmacological properties to those of the Digitalis glycosides. [12][13][14] Recent findings indicate that Helleborus root extracts are safe and possess the potential for cancer treatment.…”

Section: Introductionmentioning

confidence: 99%

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Biomimetic Total Synthesis of ( + )-Ranuncoside, a Unique Tricyclic Spiroacetal Glycoside of Christmas Rose (Helleborus niger L.)

Cuny

Fohrer

Klingler³

2022

Natural Product Communications

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Christmas Rose ( Helleborus niger L.) is an alpine plant belonging to the Ranunculaceae family. Typical for this popular ornamental plant are white flowers that appear during winter. Root extracts contain numerous medicinally active ingredients and potent cardiac glycosides. Recent findings indicate that Helleborus root extracts possess the potential for cancer treatment and inhibit the proliferation of tumor cells. In 2022, we published a practical extraction method of ( + )-ranucoside 1 from the dried leaves of H niger L. Here, we describe for the first time the total synthesis of 1. Starting from 5-hydroxylevulinic acid methyl ester 8 and acetobromo-α-D-glucose 13, the β-glycoside 14 is formed stereoselectively on the application of Koenigs-Knorr conditions. Subsequent cleavage of the acetyl-protecting groups and saponification of the ester function yields the pyrano dioxane derivative 17. Its lactonization gives ( + )-ranuncoside 1. The presented synthesis is practical and very efficient, consisting of 6 steps from D-glucose and giving 22% overall yield. Furthermore, it is biomimetic due to its concordance with the biosynthesis of ( + )-ranuncoside 1 in H foetidus.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Biomimetic Total Synthesis of ( + )-Ranuncoside, a Unique Tricyclic Spiroacetal Glycoside of Christmas Rose (Helleborus niger L.)

Cuny

Fohrer

Klingler³

2022

Natural Product Communications

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“…The Buttercup family (Ranunculaceae) is known for its use in both folk and traditional medicine [1]. The pharmaceutical importance of the buttercup family is reflected in the fact that a number of monographs describing various species of this family are a part of the pharmacopoeia.…”

Section: Introductionmentioning

confidence: 99%

Influence of Ranunculus acris Flower Extract on Allium cepa Root Meristem

Smirnova

Koygerova²,

Tsvetov³

2023

IJPB

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The plant Ranunculus acris (L.) is widespread. It is used in folk medicine. The use of herbal medicines can have adverse effects on humans and requires studies of herbal raw materials for genotoxicity. The goals of the study were to examine the toxic and genotoxic effects of aqueous solutions of R. acris flowers at concentrations of 0.625%, 1.25%, 2.5%, 5% and 10% using the Allium test and to determine the numbers of flavonoids and polyphenols and the antioxidant activity of the extracts. It has been shown that aqueous solutions of buttercup flower extract have a depressing effect on mitosis in the cells of the root meristem of Allium cepa (L.) and cause chromosomal abnormalities (chromosomal stickiness, chromosome lagging, nuclear buds and bridges in anaphase).

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“…8,11,12 Helleborus niger extracts are also used in anthroposophic medicine, 13 and clinical uses include the concomitant treatment of oncological diseases. 14 Helleborus niger extracts contain numerous active ingredients 8,[15][16][17] such as hellebrin [18][19][20][21] and helleborein, 22,23 which are powerful cardiac glycosides with pharmacological properties similar to those of the Digitalis glycosides. [24][25][26] Moreover, a recent preclinical evaluation showed that black hellebore extracts are safe and have potential for cancer treatment.…”

Section: Introductionmentioning

confidence: 99%

Efficient Isolation and Structure Analysis of (+)-Ranuncoside, a Unique Tricyclic Spiroacetal Glycoside, from Christmas Rose (Helleborus niger L.)

Cuny

Klingler²

2022

Natural Product Communications

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The use of medicinal herbs as remedies reaches back to the Stone Age, and their importance as a source of drugs has continuously increased since then. Herbal ingredients can serve as active pharmaceuticals themselves or as lead substances for the development of synthetic pharmaceuticals with less toxicity, higher effectiveness or with new properties. To date, only 6% of the ∼600,000 plants on earth have been tested pharmacologically. Among these, the medicinal plant Helleborus niger L. (Christmas rose) is especially promising because its leaves contain ( + )-ranuncoside 1, characterized by a spiroacetal ring system, a motif which is responsible for the biological activity of a multitude of natural products. Structure-activity relationship studies of ( + )-ranuncoside 1 are lacking and no synthesis of 1 has been described yet. Therefore, we developed a protocol for the rapid and efficient isolation of 1 from the leaves of cultivated Christmas rose. Crystals of high purity were obtained that enabled us to study the stereochemistry of 1 by NMR spectroscopy in solution for the first time. The spiro configuration, the absolute stereochemistry, and the geometry of all three rings was then confirmed by x-ray structure analysis. Our data will enable future structure-activity relationship studies to assess the potential of 1 as a lead substance for the development of novel antibiotics and anticancer agents.

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Stability of protoanemonin in plant extracts from Helleborus niger L. and Pulsatilla vulgaris Mill.

Cited by 10 publications

References 21 publications

Biomimetic Total Synthesis of ( + )-Ranuncoside, a Unique Tricyclic Spiroacetal Glycoside of Christmas Rose (Helleborus niger L.)

Biomimetic Total Synthesis of ( + )-Ranuncoside, a Unique Tricyclic Spiroacetal Glycoside of Christmas Rose (Helleborus niger L.)

Influence of Ranunculus acris Flower Extract on Allium cepa Root Meristem

Efficient Isolation and Structure Analysis of (+)-Ranuncoside, a Unique Tricyclic Spiroacetal Glycoside, from Christmas Rose (Helleborus niger L.)

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