Isolation, structure, and synthesis of hermidin, a chromogen from Mercurialis perennis L.

Swan, G. A.

doi:10.1039/p19850001757

Cited by 24 publications

(23 citation statements)

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“…Crawley (2005) suggested that the leaves lose much of their toxicity on senescence. A chromogen (hermidin), which turns blue on exposure to oxygen, has been extracted from the plant (Swan 1984).…”

Section: Structure and Physiologymentioning

confidence: 99%

Biological Flora of the British Isles: Mercurialis perennis L.

Jefferson

2008

Journal of Ecology

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Summary1. This account reviews information on all aspects of the biology of Mercurialis perennis that are relevant to understanding its ecological characteristics and behaviour. The main topics are presented within the standard framework of the Biological Flora of the British Isles : distribution, habitat, communities, responses to biotic factors, responses to environment, structure and physiology, phenology, floral and seed characters, herbivores and disease, history and conservation. 2. Mercurialis perennis is a dioecious, clonal, perennial forb of woodland, hedgerows, limestone pavement, screes and tall-herb communities. It is very tolerant of low light; it can also grow in unshaded conditions, although higher light flux densities result in lower shoot biomass. It is Eurocaucasic, occurring throughout temperate areas of Europe as far east as the Russian border. 3. Mercurialis perennis occurs on a wide variety of soil types over a pH range from 4.3 to 8.5, although it is most abundant on more base-rich clay or loam soils with a low organic content. It seldom occurs on peat or very sandy soils. It can grow in soils with low availability of macronutrients but it responds positively to nutrient addition from atmospheric or agricultural sources. It is intolerant of waterlogging, mainly because of poor aerenchyma development; its limited capacity to oxygenate the root environment can lead to ferrous ion toxicity. The resulting superficial root development on heavy soils may confer drought susceptibility in summer. 4. Mercurialis perennis is predominantly wind-pollinated. Ants are the main dispersal agents and the seed bears an elaiosome which offers them a lipid-rich reward. Establishment from seed is uncommon and vegetative propagation is the main means of expansion, often leading to dense clonal stands of aerial shoots. 5. Mercurialis perennis has been described as a stress-tolerant competitor. The persistence of its clones and slow dispersal have led to it being regarded an as indicator of ancient, semi-natural woodland.

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Section: Structure and Physiologymentioning

confidence: 99%

Biological Flora of the British Isles: Mercurialis perennis L.

Jefferson

2008

Journal of Ecology

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“…Cyanohermidin dimerises spontaneously into a product that is further oxidised with molecular oxygen to the yellow-brown-colored chrysohermidin (Haas and Hill, 1925;Cannan, 1926;Swan, 1985). As reported earlier by Swan (1985), hermidin is present in Mercurialis in relatively high concentration. Nothing appears to be known about its biosynthesis.…”

Section: Introductionmentioning

confidence: 79%

“…Table 3), and for ions comprising the carbon atoms of the original (Swan, 1984;Boger and Baldino, 1993). amino acids without the carboxylic acid atom (m/z = 158 or 232 from TBDMS-alanine).…”

Section: Experiments With [U-13 C 6 ]Glucosementioning

confidence: 99%

“…Since only 1 H NMR assignments for hermidin were available from the literature (Swan, 1984), the 13 C signals were assigned by HMQC and HMBC experiments. Moreover, multiply 13 C-labelled samples from the labelling experiments afforded 13 C 13 C coupling constants that confirmed the assignments and were required for the subsequent biosynthetic studies.…”

Section: Nmr Signal Assignmentsmentioning

confidence: 99%

“…The emergence of blue coloration upon addition of ammonium carbonate to Mercurialis extract had already been reported by Darwin (1882). More recently, the blue material was identified as a radical anion, cyanohermidin, that is formed from hermidin by reaction with molecular oxygen (Forrester, 1984;Swan, 1984;Boger and Baldino, 1993) (Fig. 1).…”

Section: Introductionmentioning

confidence: 98%

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Biosynthesis of the chromogen hermidin from Mercurialis annua L.

et al. 2007

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The Persulfate Oxidation of Phenols and Arylamines (TheElbs and theBoyland–Sims Oxidations)

Behrman

1988

Organic Reactions

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A phenolate anion reacts with persulfate ion in alkaline solution to yield a product in which a sulfate group enters the ring para or ortho to the phenolic group. Para substitution predominates. Subsequent acid‐catalyzed hydrolysis yields the dihydric phenol. The reaction was discovered by Karl Elbs in 1893 and named the Elbs persulfate oxidation . The reaction is generally applicable to ortho ‐, meta ‐, and para ‐substituted phenols with isomer distributions. The yields are not very high, particularly from para ‐substituted phenols, but the major contaminant is usually unchanged starting material that can be separated easily from the intermediate sulfate ester by solvent extraction. Other generally oxidizable groups such as an aldehyde or a double bond are usually not affected under the reaction conditions. The reaction was last thoroughly reviewed in 1951. T. R. Seshadri has made major contributions to the development of the Elbs oxidation. Nearly 30% of the references in this chapter are due to him and his colleagues. By analogy with the Elbs persulfate oxidation of phenols, it might be expected that aromatic amines would react with persulfate to give p ‐aminoaryl sulfates. Although the Elbs reaction had been known since 1893, it was not until 60 years later that Boyland et al. reported the extension of this reaction to aromatic amines. In accordance with expectations, aminoaryl sulfates were indeed the major products of the reaction, but, unexpectedly, the substitution took place exclusively ortho to the amino group rather than predominantly in the para position as in the phenol oxidation. Para substitution takes place only if the ortho positions are occupied by substituents other than hydrogen. Boyland and Sims explored the preparative aspects of this reaction in a series of papers. It seems appropriate to name the reaction the Boyland–Sims oxidation. Primary, secondary, and tertiary aromatic amines are all converted to the corresponding o ‐aminoaryl sulfates under conditions similar to those used for the Elbs oxidation, that is, room temperature or below, aqueous alkali, and equimolar quantities of amine and persulfate.

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Isolation, structure, and synthesis of hermidin, a chromogen from Mercurialis perennis L.

Cited by 24 publications

References 4 publications

Biological Flora of the British Isles: Mercurialis perennis L.

Biological Flora of the British Isles: Mercurialis perennis L.

Biosynthesis of the chromogen hermidin from Mercurialis annua L.

The Persulfate Oxidation of Phenols and Arylamines (TheElbs and theBoyland–Sims Oxidations)

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