Showing papers on "Indole alkaloid published in 1994"
123 citations
TL;DR: Results indicated that the in situ adsorption sequentially applied with permeabilization and fungal elicitation have a synergistic effect on the production and secretion of indole alkaloids.
67 citations
TL;DR: A new indole alkaloid and new C 19 and C 20 skeleton quassinoids were isolated from the wood of Ailanthus malabarica by spectroscopic and X-ray analysis.
25 citations
TL;DR: In this paper, two new corymine-related indole alkaloids, Na-demethylcorymine (2) and Na-denethyldeformylcorymin (4), were isolated from the leaves of Hunteria zeylanica native to Thailand and determined by spectroscopic analysis and chemical correlation.
Abstract: Two new corymine-related indole alkaloids, Na-demethylcorymine (2) and Na-demethyldeformylcorymine (4), were isolated from the leaves of Hunteria zeylanica native to Thailand. Their structures were determined by spectroscopic analysis and chemical correlation.
20 citations
TL;DR: Pamburus missionis root contained imperatorin and 7-hydroxy-8-(3′,7′-dimethyl octa-2′,6′-dien)ylcoumarin and a new natural product, 3-(3-methyl-1-oxo-2-butenyl) 1H indole.
17 citations
TL;DR: A new naturally occurring flavonoid, 3,5,7,3′,4′,5′-hexamethoxyflavone, and a new indole alkaloid, murrayaculatine, were isolated and characteriz
17 citations
TL;DR: Two cell lines of Tabernaemontana divaricata derived from the same suspension culture seem to have the same biotransformation potential, since all the alkaloids added were transformed the same way by both cultures.
17 citations
TL;DR: A stereocontrolled formal synthesis of (−)-eburnamonine, a tetracyclic indole alkaloid used as antihypertensive drug, has been achieved through the use of [3, 3]-sigmatropic rearrangement (Claisen rearrangements) of the enantiopure β-alkoxy acrylate 4, available from rac-3-ethly-cyclohexenol 3 via lipase-catalyzed transesterification.
17 citations
TL;DR: A novel glycosidic alkaloid, hunterioside, together with strictosidinic acid was isolated from Hunteria zeylanica, and the structure was found to be 6'-alpha-D-glucoside of strictosodinic acid, the first finding of a bioside congener of monoterpenoid indole alkaloids glucosides.
Abstract: A novel glycosidic alkaloid, hunterioside, together with strictosidinic acid was isolated from Hunteria zeylanica, and the structure was found to be 6'-α-D-glucoside of strictosidinic acid. This isolation is the first finding of a bioside congener of monoterpenoid indole alkaloid glucosides.
16 citations
TL;DR: In this article, a Gelsemium alkaloid, gelsemicine, was synthesized from a sarpagine-type indole alkalinoid, gardnerine via humantenine and gelselegine-and gelsenicine-type compounds.
Abstract: A Gelsemium alkaloid, gelsemicine is synthesized from a sarpagine-type indole alkaloid, gardnerine, via humantenine, gelselegine- and gelsenicine-type compounds.
15 citations
TL;DR: In this article, the synthesis of aldehyde intermediates suitable for the preparation of indole alkaloids of the tacamine (1) type is described, and four possible aldehydes 4-7 were prepared from methyl 5-ethylnicotinate (8) in a few simple steps using a base-catalyzed epimerization as the final step.
Abstract: The synthesis of aldehyde intermediates suitable for the preparation of indole alkaloids of the tacamine (1) type is described. The four possible aldehydes 4–7 were prepared from methyl 5-ethylnicotinate (8) in a few simple steps using a base-catalyzed epimerization as the final step (Schemes 1 and 2). The key aldehyde 4, which is an analogue of the important vincamine intermediate 3 (‘Oppolzer's aldehyde’), was finally converted into the indole alkaloid (±)-apotacamine (21).
TL;DR: The leaves of Rauwolfia sumatrana JACK collected in Thailand resulted in the isolation of three new bis-indole alkaloids, 11-methoxystrictamine (1), rausutrine (4), and Rausutranine (7), along with ten known bases, harman, tetraphyllicine, flexicorine, lanceomigine, perakine, β-carboline, peraksine, 10-hydroxystrictamines, cabufiline and compactinervine as mentioned in this paper
Abstract: Chemical investigation of the leaves of Rauwolfia sumatrana JACK. collected in Thailand resulted in the isolation of three new indole alkaloids, 11-methoxystrictamine (1), rausutrine (4) and rausutranine (7), along with ten known bases, harman, tetraphyllicine, flexicorine, lanceomigine, perakine, β-carboline, peraksine, 10-hydroxystrictamine, cabufiline and compactinervine. Rausutrine (4) and rausutranine (7) are novel bis-indole alkaloids composed of an akuammilane unit and a vincorane unit, the latter of which has a unique iminoquinone function.
TL;DR: In this article, the indole alkaloid (±)-tacamine was converted to indole acyclic intermediates via acid-catalyzed displacement of the dimethylamino group with the hydroxyl group via an iminium intermediate.
TL;DR: A new alkaloid was isolated from the leaves of Gardneria nutans, having a 4-quinolone nucleus corresponding to the monoterpenoid indole alkaloids, which substance is a plausible biogenetic precursor of gardnerine.
Abstract: A new alkaloid, gardquinolone [1], was isolated from the leaves of Gardneria nutans. Its unique structure, having a 4-quinolone nucleus corresponding to the monoterpenoid indole alkaloids, was determined by spectroscopic analysis and chemical transformation from the indole alkaloid, gardnerine [2], which substance is a plausible biogenetic precursor of 1
TL;DR: Two new indole alkaloids, 10-hydroxystrictamine (1) and alstomacrocine (2), have been isolated from Alstonia macrophylla wall and their structures were elucidated on the basis of modern spectroscopic techniques.
Abstract: Two new indole alkaloids, 10-hydroxystrictamine (1) and alstomacrocine (2), have been isolated from Alstonia macrophylla Wall and their structures were elucidated on the basis of modern spectroscopic techniques.
TL;DR: The first total synthesis of the indole alkaloid (+)-aristolone ((+)- 2 ) is described in this article, which uncovered the hitherto unknown relative and absolute configuration of this rare metabolite which had been isolated before by others in ppm-amounts from Aristotelia australasica.
Abstract: The first total synthesis of the highly functionalized monoterpenoid indole alkaloid (+)-aristolone ((+)- 2 ) is described. This investigation uncovered the hitherto unknown relative and absolute configuration of this rare metabolite which had been isolated before by others in ppm-amounts from Aristotelia australasica . Dehydration of synthetic (+)- 2 led to a readily separable mixture of the two alkaloids 11,12-didehydro-10-oxomakomakine ((+)- 3 ) and 11,12-didehydro-10-oxohobartine ((−)- 4 ) which had been isolated in 1988 from A. chilensis .
Patent•
02 Dec 1994TL;DR: Shearinines A, B and C, and 21-Isopentenylpaxilline are ascostromatal metabolites of the fungus Eupenicillium shearii.
Abstract: Shearinines A, B and C, and 21-Isopentenylpaxilline are ascostromatal metabolites of the fungus Eupenicillium shearii. These indole alkaloid compounds are effective for controlling Coleopteran and Lepidopteran insects and the fall armyworm, Spodoptera frugiperda.
TL;DR: A new type of Gelsemium alkaloid, 11-methoxygelsemamide (2), having a 1,2-secoindole system, was synthesized for the first time from a sarpagin this article.
TL;DR: The marine indole alkaloid villagorgin A was synthesized by reduction and cyclization of an indolylethylimidazopyridinium salt by oxidation with mercuric acetate.
Abstract: The marine indole alkaloid villagorgin A was synthesized by reduction and cyclization of an indolylethylimidazopyridinium salt. Its oxidation with mercuric acetate gave villagorgin B.
TL;DR: In this paper, a short total synthesis of crooksidine and demethoxycarbonyltetrahydrosecodine is described, and the synthesis is shown to be possible.
Abstract: A short total synthesis of crooksidine and demethoxycarbonyltetrahydrosecodine is described.
Patent•
29 Aug 1994TL;DR: Indole alkaloid compounds and their reduction products are useful as both UV protective and anti-inflammatory agents as discussed by the authors. But they are not suitable for use as anti-malignancy agents.
Abstract: Indole alkaloid compounds having the formula ##STR1## where R and R' are H, an alkyl group having up to 5 carbon atoms or --CO--(CH 2 ) n --CH 3 where n=0 to 16 The indole alkaloid compounds and their reduction products are useful as both UV protective and anti-inflammatory agents
TL;DR: In this paper, a Gelsemium alkaloid, gelsemicine, was synthesized from a sarpagine-type indole alkalinoid, gardnerine via humantenine and gelselegine-and gelsenicine-type compounds.
Abstract: A Gelsemium alkaloid, gelsemicine is synthesized from a sarpagine-type indole alkaloid, gardnerine, via humantenine, gelselegine- and gelsenicine-type compounds.
TL;DR: In this article, the synthesis of aldehyde intermediates suitable for the preparation of indole alkaloids of the tacamine (1) type is described, and four possible aldehydes 4-7 were prepared from methyl 5-ethylnicotinate (8) in a few simple steps using a base-catalyzed epimerization as the final step.
Abstract: The synthesis of aldehyde intermediates suitable for the preparation of indole alkaloids of the tacamine (1) type is described. The four possible aldehydes 4–7 were prepared from methyl 5-ethylnicotinate (8) in a few simple steps using a base-catalyzed epimerization as the final step (Schemes 1 and 2). The key aldehyde 4, which is an analogue of the important vincamine intermediate 3 (‘Oppolzer's aldehyde’), was finally converted into the indole alkaloid (±)-apotacamine (21).
TL;DR: A stereocontrolled formal synthesis of (−)-eburnamonine, a tetracyclic indole alkaloid used as antihypertensive drug, has been achieved through the use of [3, 3]-sigmatropic rearrangement (Claisen rearrangements) of the enantiopure β-alkoxy acrylate 4, available from rac-3-ethly-cyclohexenol 3 via lipase-catalyzed transesterification as discussed by the authors.
Abstract: A stereocontrolled formal synthesis of (−)-eburnamonine 1, a tetracyclic indole alkaloid used as antihypertensive drug, has been achieve through the use of [3,3]-sigmatropic rearrangement (Claisen rearrangement) of the enantiopure β-alkoxy acrylate 4, available from rac-3-ethly-cyclohexenol 3 via lipase-catalyzed transesterification