Trennung des Aloins in Diastereomere und deren Charakterisierung

Auterhoff, H.; Graf, Eva-Maria; Eurisch, Gunther; Alexa, Mihai

doi:10.1002/ardp.19803130204

Cited by 29 publications

(7 citation statements)

References 4 publications

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“…The retention time and UV spectral data of compound 6 were the same as those of aloin B (C 21 H 22 O 9 ) obtained by HSCCC (Cao et al ., ). Meanwhile, as aloin A is easily subject to interconversion via the tautomeric anthranol (Rauwald, ) and aloin B is eluted out ahead of aloin A in reverse HPLC (Auterhoff et al ., ), compound 6 was identified as aloin B. Compound 7 was known to be the reference substance of aloin A (C 21 H 22 O 9 ).…”

Section: Resultsmentioning

confidence: 99%

Effects of temperature, pH and light on the stability of aloin A and characterisation of its major degradation products

Ding

Zhong

et al. 2014

Int J of Food Sci Tech

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Summary This study explored the stability and degradation products of aloin A under varying pH, temperature and light conditions usually encountered in processing. The stability of aloin A was significantly affected by temperature and pH. The content of aloin A decreased by more than 90% within 12 h at 50 °C and within 6 h at 70 °C, respectively. A significant decrease in stability was also observed at higher pHs. At pH 8.0, less than 2% of aloin A remained within 12 h. However, aloin A exhibited good stability at acidic pH levels with 94% remaining at pH 2.0 for 14 days. Light exerted no influence on the stability during the experimental period (14 days). Aloe‐emodin, elgonica‐dimers A and B were characterised as major degradation products of aloin A at pH 5.0 or below, and elgonica‐dimers were mainly formed at 4 °C as well. 10‐hydroxyaloins A and B were found under any condition except at pH 2.0 and 3.0, and they were mainly formed under high temperature, neutral‐basic and any light conditions.

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Section: Resultsmentioning

confidence: 99%

Effects of temperature, pH and light on the stability of aloin A and characterisation of its major degradation products

Ding

Zhong

et al. 2014

Int J of Food Sci Tech

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“…As aloin A is less polar than aloin B, it is eluted out after aloin B in reverse HPLC. [17] According to the similar data with aloin A except the retention time, compound 1b was identified as the isomer of aloin A, named aloin B. The above data implied that peak 1 was a mixture of aloin diastereoisomers.…”

Section: Confirmation Of Chemical Structuresmentioning

confidence: 77%

“…[17] UV (MeOH) k max nm: 223.3, 268.3, 296.5, 355.0; IR (KBr) n max cm À1 : 3385, 1636, 1618, were of congruent UV and IR spectral data and molecular weight, i.e., 418, implying that they were two isomers. As shown in Figure 3, compound 1a had similar retention time in HPLC with the reference substance of aloin A, so compound 1a was identified as aloin A.…”

Section: Confirmation Of Chemical Structuresmentioning

confidence: 91%

ISOLATION AND PURIFICATION OF ALOIN, ISOALOERESIN D AND ALOENIN-2′-p-COUMAROYL ESTER FROM Aloe barbadensis MILL BY HIGH-SPEED COUNTER-CURRENT CHROMATOGRAPHY

Zhong

Xie

et al. 2013

Journal of Liquid Chromatography & Related Technologies

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& Aloin, isoaloeresin D, and aloenin-2 0 -p-coumaroyl ester were separated and purified from Aloe barbadensis Mill by one step of high-speed counter-current chromatography for the first time. The separation was performed with an optimized two-phase solvent system composed of hexane-ethyl acetate-acetone-water (0.2:5:1.5:5, v=v=v=v), using the lower phase as the mobile phase in the head-to-tail elution mode. The revolution speed of the separation column, flow rate of the mobile phase, and UV detection wavelength were 860 rpm, 1.5 mL Á min À1 , and 300 nm, respectively. In a one-step operation, 51.9 mg of aloin, 23.1 mg of isoaloeresin D, and 6.5 mg of aloenin-2 0 -p-coumaroyl ester could be obtained from 161.7 mg of dried acetone extract at purities of 99.2%, 98.5%, and 95.6%, respectively, as determined by HPLC using area normalization method. The partial separation of aloin A and aloin B was also obtained. The structures of these compounds were identified by high resolution mass spectroscopy (HRMS), UV, IR, and NMR.

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“…Barbaloin peaks were detected by absorbence at 375 nm and retention times and peak areas compared with a calibration curve prepared from standard barbaloin solutions. Under these solvent conditions the two diastereoisomers (15,16) were not separated so that the barbaloin peak was estimated as a single entity.…”

Section: Determination Of Barbaloin In Leaf Exudatesmentioning

confidence: 99%

Barbaloin inAloeSpecies

Groom

Reynolds²

1987

Planta Med

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Barbaloin levels in the exudates from the leaves of 68 species of ALOE in the Kew collection have been determined by light absorption at 375 nm following separation by HPLC. The exudates from most species contained between 10-20% although a few concentrations of around 30% were found. The level in the leaf was usually around 1% of thedry weight in plants grown in glasshouses at Kew although some species were found to contain up to 5%. The highest concentrations of barbaloin were found in exudates from young mature leaves just below the apex and the level decreased in older leaves towards the base of the plant. Species in the natural groupings of the genus, Section ANGUIALOE and Group 4, all had appreciable concentrations of barbaloin in the leaf exudates. Species containing barbaloinwere distributed throughout the large heterogeneous Sections EUALOE and PACHYDENDRON with no apparent taxonomic significance.

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Trennung des Aloins in Diastereomere und deren Charakterisierung

Cited by 29 publications

References 4 publications

Effects of temperature, pH and light on the stability of aloin A and characterisation of its major degradation products

Effects of temperature, pH and light on the stability of aloin A and characterisation of its major degradation products

ISOLATION AND PURIFICATION OF ALOIN, ISOALOERESIN D AND ALOENIN-2′-p-COUMAROYL ESTER FROM Aloe barbadensis MILL BY HIGH-SPEED COUNTER-CURRENT CHROMATOGRAPHY

Barbaloin inAloeSpecies

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