Indole Alkaloids of Ailanthus altissima

Varga, E.; Szendrei, K.; Reisch, J.; Maróti, Gergely

doi:10.1055/s-2008-1074981

Cited by 19 publications

(13 citation statements)

References 3 publications

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“…malabarica (wood) Aono et al (1994), Said et al (2006), Ohmoto et al (1976Ohmoto et al ( , 1981, Varga et al (1980), Souleles and Waigh (1984), Cordell et al (1978) and Koike and Ohmoto (1985) 17…”

Section: Chemical Constituentsmentioning

confidence: 92%

“…Most of the alkaloids have basic b-Carboline skeleton like Skeleton-I (1-15), six (16-21) may be represented by Canthin-6-one skeleton (Skeleton-II), two (22, 23) by Canthin-6-one-3 N-oxide skeleton (Skeleton-III) and residual two (24 and 25) have individual structures. Aono et al (1994), Ohmoto et al (1981), Joshi et al (1977) and Ohmoto and Koike (1983) 3 b-Carboline-1-propionic acid A. altissima (root bark), A. malbarica (wood) Aono et al (1994) and Ohmoto and Koike (1984) 4 Methyl-4-methoxy-b-caboline carboxylate A. altissima (root bark) Varga et al (1980) …”

Section: Chemical Constituentsmentioning

confidence: 98%

“…altissima (root bark, dried leaves, wood) Ohmoto et al (1981), Varga et al (1980), Souleles and Waigh (1984), Cordell et al (1978) and Ohmoto et al (1976) 19 8-Hydroxycanthine-6-one A. excelsa (root bark) Cordell et al (1978) 20 5-Methoxycanthine-6-one A. excelsa (root bark) Cordell et al (1978) 21 5-Hydroxymethylcanthine-6-one A. altissima (root bark) Ohmoto and Koike (1984) 22 Canthine-6-one-3-N-oxide A. altissima (wood),…”

Section: Chemical Constituentsmentioning

confidence: 99%

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A brief resume on the genus Ailanthus: chemical and pharmacological aspects

Kundu

Laskar

2009

Phytochem Rev

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Over the past decade, herbal medicine has become an item of global importance, with both medicinal and economic implications. Thus, accurate scientific assessment has become a prerequisite for acceptance of herbal health claims. The plants of genus Ailanthus, belong to the family Simaroubaceae, is widely used in Ayurveda and evidence-based phytotherapy. Several species of the genus Ailanthus are widely distributed over Asia and north Australia and studied extensively over the last few decades. A compilation of the constituents isolated from different Ailanthus species covering the literature up to December 2008 is presented in the review. The botanical classification and ethno-pharmacology of Ailanthus plants, as well as the biological activities and pharmacological applications of both distinct phytochemicals and active plant materials (formulations, extracts etc.), are discussed in detail.

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Section: Chemical Constituentsmentioning

confidence: 92%

Section: Chemical Constituentsmentioning

confidence: 98%

Section: Chemical Constituentsmentioning

confidence: 99%

See 1 more Smart Citation

A brief resume on the genus Ailanthus: chemical and pharmacological aspects

Kundu

Laskar

2009

Phytochem Rev

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“…(Simaroubaceae) is used in Chinese traditional medicine as a bitter-aromatic drug, in the treatment of cold and gastric diseases and as an antitumoral. Previous phytochemical studies have demonstrated the presence in the plant of quassinoids (Casinovi et al, 1983;Chiarlo and Pinca, 1965;Kubota et al, 1996;Lu et al, 2002;Niimi et al, 1987) as well as indole and β-carboline alkaloids (Ohmoto et al, 1981;Ohmoto and Koike, 1984;Souleles and Kokkalou, 1989;Varga et al, 1981).…”

Section: Introductionmentioning

confidence: 97%

Antiproliferative effects of tree-of-heaven (Ailanthus altissima Swingle)

et al. 2005

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Tree-of-heaven (Ailanthus altissima Swingle) was evaluated for its cytotoxic and antiproliferative activities by a bioassay-oriented study. Cytotoxicity observed in HeLa cells was time-dependent; the treatment with 10 microg/mL of the root chloroform extract reduced cell viability by 56% at 24 h and 29% at 48 h of exposure, whereas no effect was recorded in the controls. Significant effects were observed also for chromatographic fractions and the pure isolated alkaloid 1-methoxy-canthin-6-one. After 72 h of incubation cell viability was less than 10% for all treatments. A possible apoptotic effect was evaluated by monitoring the presence of hypodiploid elements in HeLa cells as well as in SAOS, U87MG and U-937 tumor cell lines. The cells incubated for different times with the active extract, fraction and pure alkaloid isolated from A. altissima showed a remarkable increase in the apoptosis.

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“…Swingle, Simaroubaceae, is a large tree («Tree of Heaven») distributed from Southeast Asia to China and Taiwan, but is also grown in cities in Europe and North America. It is employed as an antibacterial, anthelmintic, amoebicide, and insecticide [1][2][3]. Its biological activities depend mainly on quassinoids as well as on indole alkaloids, either the simple β-carbolines or the canthin-6-ones [4,5].…”

mentioning

confidence: 99%

Sterones and indole alkaloid from Ailanthus altissima callus cultures

2007

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UDC 543:547.9Ailanthus altissima (Mill.) Swingle, Simaroubaceae, is a large tree («Tree of Heaven») distributed from Southeast Asia to China and Taiwan, but is also grown in cities in Europe and North America. It is employed as an antibacterial, anthelmintic, amoebicide, and insecticide [1][2][3]. Its biological activities depend mainly on quassinoids as well as on indole alkaloids, either the simple β-carbolines or the canthin-6-ones [4,5]. Quassinoids from A. altissima have been shown to possess antiplasmodial activity [6,7]. Canthin-6-one alkaloids from A. altissima have proven cytotoxic activity as well as anti-proliferative and antiprotozoal effects [5,8,9]. Cell cultures of A. altissima have been of particular interest for their remarkable ability to produce high yields of the canthin-6-one alkaloids normally found as very minor constituents [5]. The purpose of this study was to look at the secondary metabolites produced by callus cultures of A. altissima in more detail.In the present investigation, freeze dried callus cultures of A. altissima were extracted subsequently with petroleum ether and chloroform. From the crude chloroform by CC on silica gel and using reverse phase HPLC, 6-β-OH-stigmasta-4-en-3-one (1) [10] and 6-β-OH-stigmasta-4,22-dien-3-one (2) [11] were obtained as amorphous white powders.Petroleum ether and CHCl 3 extracts were also checked for alkaloids. TLC control of the petroleum ether fraction showed only minor amounts of alkaloids. However, from the chloroform extract several indole alkaloids could be isolated. Besides canthin-6-one, 1-methoxycanthin-6-one, 1-hydroxycanthin-6-one, canthin-6-one-3-N-oxide, and 4-methoxy-β-carboline-1-carboxylic acid methyl ester, already previously reported as constituents in callus and cell suspension cultures of A. altissima [5,7], 4,8-dimethoxy-β -carboline-1-carboxylic acid methyl ester (3) was found. For 1 H NMR see [20]; 13 C NMR data of 3 are presented here for the first time.So far, no reports could be found on the occurrence of 1 and 2 in cell cultures. 6-β-OH-Stigmasta-4-en-3-one (1) was previously detected aside from other plant sources in the fruits of A. altissima [12], 2 in different plants like Phaseolus vulgaris roots [13] and stems of Annona cherimola [14]. Both compounds were obtained by microbiological transformation of β-sitosterine and stigmasterine, respectively [15,16]. Stigmast-4-en-3-one (β-sitosterone) was isolated from the heartwood of Quassia amara, also belonging to the Simaroubaceae family [17]. Compound 2 and the related diketone stigmasta-4,22-dien-3,6-dione are regarded as potent allelochemicals [18,19]. So far only the β-carboline 3 was detected in the leaves of A. altissima [20].Due to our investigations the production of a range of β-carboline and canthin-6-one alkaloids in callus cultures of A. altissima could be confirmed. The production of sterones in plant cell cultures has not been studied well before and in further investigations on their biosynthesis and biological functions plant tissue cultures of A. altissim...

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Indole Alkaloids of Ailanthus altissima

Abstract: From the root bark of Ailanthus altissima four simple indole alkaloids have been isolated: Cathin-6-one (I), 1-methoxy-cathin-6-one (11), Methyl 6-methoxy-P-carboline-I-carboxylate (111) and an unidentified alkaloid.

Cited by 19 publications

References 3 publications

A brief resume on the genus Ailanthus: chemical and pharmacological aspects

A brief resume on the genus Ailanthus: chemical and pharmacological aspects

Antiproliferative effects of tree-of-heaven (Ailanthus altissima Swingle)

Sterones and indole alkaloid from Ailanthus altissima callus cultures

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