605. The aloins. Part I. The structure of barbaloin

Hay, John; Haynes, Lee

doi:10.1039/jr9560003141

Cited by 65 publications

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“…var. natalensis BERGER (Liliaceae), 8,9) Rheum palumatum L. (Poligonaceae), 10,11) Cassia tora L. (Leguminosae), 12) and so on. This anthraquinone derivative has two phenolic hydroxyl groups at the 1 and 8 positions and one aliphatic hydroxyl group at the 15 position.…”

Section: Resultsmentioning

confidence: 99%

Preparation of 1,8-Di-O-alkylaloe-emodins and 15-Amino-, 15-Thiocyano-, and 15-Selenocyanochrysophanol Derivatives from Aloe-Emodin and Studying Their Cytotoxic Effects

et al. 2008

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Previously, we reported that when the cytotoxic effects of 4Ј-O-alkylaloenin derivatives (from methyl to hexadecyl) derived from aloenin (1) are compared, the longer the alkyl chain of the 4Ј-O-alkylaloenin derivatives, the greater is the enhancement in the cytotoxic effects on human colorectal (HCT 116) and human hepatoma (Hep G2) cancer cell lines.1) Furthermore, we reported that pseudodiosgenone derivatives having various amino groups, thiocyano (SCN), and selenocyano (SeCN) groups at the 26 position derived from diosgenin (2) exhibited the potent cytotoxic activities against the same cancer cell lines, 2) while compounds 1 and 2 have not been known to exhibit cytotoxic activity yet. In our preliminary investigation, these compounds also showed no marked cytotoxicity in less than 500 mM of the IC 50 valuethe concentration at which 50% of the cells are inhibited from growing. However, from the both above-mentioned reports, it is evident that a compound that possessed an alkyl chain with an appropriate length or that introduced appropriate substituents such as amino, thiocyano, and selecocyano groups in the molecule seemed to exhibit potent cytotoxic activity.In the present study, we investigate the preparation of 1,8-di-O-alkylaloe-emodins and 15-amino-, 15-thiocyano-, and 15-selenocyanochrysophanol derivatives from aloe-emodin (3) which has been known to have several pharmacological activities such as cytotoxic activity, [3][4][5] antifungal activity, 6) antibacterial activity, 7) and so on, and further we evaluate the cytotoxic effects of the synthetic derivatives on HCT 116 and Hep G2 cancer cell lines. Results and DiscussionAloe-emodin 3 is an anthraquinone derivative isolated from many Chinese herbal medicines such as Aloe arborensces MILL. var. natalensis BERGER (Liliaceae), 8,9) Rheum palumatum L. (Poligonaceae), 10,11) Cassia tora L. (Leguminosae), 12) and so on. This anthraquinone derivative has two phenolic hydroxyl groups at the 1 and 8 positions and one aliphatic hydroxyl group at the 15 position. In this study, the alkylations of the phenolic hydroxyl groups and the substitution reactions with various amino groups and thiocyano and selenocyano groups at the 15 position of 3 were performed to compare their cytotoxic activities. First, several alkyl derivatives were prepared from 3. The methylation of 3 with dimethylsulfate in the presence of K 2 CO 3 was done according to the method reported by Ross and Mitali. 13) to give 1,8-di-O-methylaloe-emodin 4 in a 61.6% yield. Other alkylations were performed according to the method of MacTough et al. 14) Compound 3 was reacted with propyl iodide, hexyl bromide, dodecyl iodide, and octadecyl iodide in the presence of K 2 CO 3 to give 1, Sciences, Josai International University; 1 Gumyo, Togane, Chiba 283-8555, Japan: and c Faculty of Pharmaceutical Sciences, Himeji Dokkyo University; 7-2-1 Kami Ohno, Himeji, Hyogo 670-8524, Japan. Received November 9, 2007; accepted February 6, 2008 1,8-Di-O-alkylaloe-emodin derivatives (namely, methyl-, propyl-, ...

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Section: Resultsmentioning

confidence: 99%

Preparation of 1,8-Di-O-alkylaloe-emodins and 15-Amino-, 15-Thiocyano-, and 15-Selenocyanochrysophanol Derivatives from Aloe-Emodin and Studying Their Cytotoxic Effects

et al. 2008

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“…We recently isolated a new bitter glucoside, named aloenin (1 ), as a m ajor constituent from the leaf juice of this plant, and elucidated its struc ture 8' 10" 14,17 and biosynthetic pathway 18. Nishioka et al, on the other hand, found 2 , -0-feruloylaloesin ( 2 ) 12, 2 //-0-p-coumaloylaloesin ( 3 ) 12, and aloearbonaside 9 in the leaves of the plant; the last compound was identified with aloenin (1 ). Since chemical con stituents other than these compounds, 1, 2, and 3, have not been examined yet with the A loe arbo rescens, we have now investigated the constituents of the leaves and the roots to clarify whether the Aloe plants contain the biologically active substances which are effective for the folk remedies materials.…”

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Biologically Active Constituents of Leaves and Roots of Aloe arborescens var. natalensis

Hirata

Suga

1977

Zeitschrift Für Naturforschung C

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Aloe Plant (Liliaceae), Biologically Active Substances, Inhibitory Activity on Gastric Juice SecretionSeveral biologically active substances, such as aloenin (1), magnesium lactate, aloe-emodin (4), barbaloin (5), and succinic acid, were found to be contained in the leaf juice of A loe arborescens Mill. var. n atalensis Berger, which has widely been used in domestic medicines. Aloenin (1) and magnesium lactate were elucidated to exhibit an inhibitory action on the gastric juice secretion of rats. Various constituents other than the above bioactive substances were found in the leaves and the roots of the plant.The chemical constituents of the plants of Aloe species used widely in domestic medicines have been investigated by several groups of w o rkers1-16, and the anthraquinone derivatives of the constituents have been reported to be effective as a peptic or a laxative ^ 2. In this country, A loe arborescens Mill, var. natalensis Berger (Japanese name: Kidachirokai or Kidachiaroe) has traditionally been used as the m aterials for folk remedies for gastro-intestinal disturbances, burns, insect bites, athlet's foot, and etc. We recently isolated a new bitter glucoside, named aloenin (1 ), as a m ajor constituent from the leaf juice of this plant, and elucidated its struc ture 8' 10" 14,17 and biosynthetic pathway 18. Nishioka et al., on the other hand, found 2 , -0-feruloylaloesin ( 2 ) 12, 2 //-0-p-coumaloylaloesin ( 3 ) 12, and aloearbonaside 9 in the leaves of the plant; the last compound was identified with aloenin (1 ). Since chemical con stituents other than these compounds, 1, 2, and 3, have not been examined yet with the A loe arbo rescens, we have now investigated the constituents of the leaves and the roots to clarify whether the Aloe plants contain the biologically active substances which are effective for the folk remedies materials. emodin (4) x, barbaloin (5) 1, aloesin (6) 6, suc cinic acid, D-glucose, and magnesium lactate. Al though the anthraquinone derivatives, (4) and (5 ), and aloesin (6) have been reported to be present in other Aloe species 11 6, this has not been the case for A loe arborescens. The dry-incinerated sample of the leaf juice was further found to contain the metal ions composed mainly of potassium and sodium atoms on spectroscopic analyses. In addition, a methanol extract of the leaf residue consisted of n-alkanes, n-triacontanol, n-dotriacontanol, sito sterol, free fatty acids, and fatty acid methyl esters. On the other hand, a methanol extract of the roots was found to be composed of n-alkanes, aloe-emodin (4 ), sitosterol, 1-linoleyl monoglyceride, fatty acids, fatty acid methyl esters, 3-0-[/?-D-glucopyranosyl] -sitosterol, D-glucose, and magnesium lactate.Since the leaf materials of the Aloe plant are fre quently used as the folk remedies materials for gastro-intestinal disturbance, an effect of the con stituents on the gastric juice secretion was tested fol lowing Shay's method 19. As the result, aloenin (1) R esults and D iscussionThe leaves of the Aloe plant were minced a...

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“…In the spectrum of aloe-emodin two C=O stretching frequencies are observed at 1,674 and 1,626 cm.-l. These are assigned to the free and the bonded carbonyl groups respectively (13). Aloeemodin monoacetate exhibits the two quinonoid carbonyl frequencies in essentially the same positions uiz., 1,670 and 1,620 cm.-l (Fig.…”

Section: Resultsmentioning

confidence: 99%

Anthraquinone Drugs II: Inadvertent Acetylation of Aloe-Emodin During Preparation of Aglycones From Crude Drugs–UV, IR, and NMR Spectra of the Products

Gyanchandani¹,

Nigam²

1969

Journal of Pharmaceutical Sciences

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605. The aloins. Part I. The structure of barbaloin

Cited by 65 publications

References 0 publications

Preparation of 1,8-Di-O-alkylaloe-emodins and 15-Amino-, 15-Thiocyano-, and 15-Selenocyanochrysophanol Derivatives from Aloe-Emodin and Studying Their Cytotoxic Effects

Preparation of 1,8-Di-O-alkylaloe-emodins and 15-Amino-, 15-Thiocyano-, and 15-Selenocyanochrysophanol Derivatives from Aloe-Emodin and Studying Their Cytotoxic Effects

Biologically Active Constituents of Leaves and Roots of Aloe arborescens var. natalensis

Anthraquinone Drugs II: Inadvertent Acetylation of Aloe-Emodin During Preparation of Aglycones From Crude Drugs–UV, IR, and NMR Spectra of the Products

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