Structure of pithecolobine. II

Wiesner, K.; Macdonald, D.D.; Bankiewicz, C.; Orr, D. E.

doi:10.1139/v68-312

Cited by 19 publications

(11 citation statements)

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(6 reference statements)

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“…A wide range biological activities of A. saman and pithecolobine have been reported previously (23,26,27). Pithecolobine isolated from S. saman demonstrated antimicrobial activity against B. subtilis and plant pathogenic molds (2).…”

Section: Discussionmentioning

confidence: 99%

“…The leaves are used in folk remedy for stomach cancer, common cold, diarrhoea, headache, intestinal ailments, sore throat, stomach ache, and wounds (18). Some biological activities of this plant have been reported in aqueous and solvent extracts (3-5, 10, 17, 19, 24), and phytochemical analysis of this species revealed pithecolobine as the main alkaloid (26,27). Some biological activities have been reported for pithecolobine (2).…”

Section: Bioactivities Of Pithecolobine Of a Saman 439mentioning

confidence: 99%

“…The IR spectrum of active compounds showed characteristic absorption peaks at (KBr) cm (27), the isolated compound was identified as pithecolobine.…”

Section: Identification Of Bioactive Compoundsmentioning

confidence: 99%

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Evaluation of Antimicrobial and Antioxidant Properties of Pithecolobine Isolated fromAlbizia saman

Thippeswamy

Mohana

Abhishek

et al. 2015

Journal of Herbs, Spices & Medicinal Plants

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Section: Discussionmentioning

confidence: 99%

Section: Bioactivities Of Pithecolobine Of a Saman 439mentioning

confidence: 99%

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Evaluation of Antimicrobial and Antioxidant Properties of Pithecolobine Isolated fromAlbizia saman

Thippeswamy

Mohana

Abhishek

et al. 2015

Journal of Herbs, Spices & Medicinal Plants

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“…We have shown in our second communication (1) that the Hofrnann degradation of pithecolobine yields besides a mixture of neutral unsaturated amides, the lactone 2 by internal displacement. Hydrogenation and hydrolysis of the unsaturated amides gave ndodecanoic acid contaminated by some n-tridecanoic and n-tetradecanoic acid.…”

mentioning

confidence: 82%

“…In the second communication (1) of this series we have shown that the "alkaloid pithecolobine" is in fact a mixture of homologues and analogues represented by the general formula 1.…”

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confidence: 98%

Structure of pithecolobine. III. The synthesis of the 1,5- and 1,3-desoxypithecolobines

Wiesner¹,

Valenta²,

Orr³

et al. 1968

Can. J. Chem.

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The second communication of ihis series has shown that "pithecolobine" is a family of closely related analogues represented by the general formula 1. In the present paper a crude semiquantitative estimate of the individual components is achieved by a combination of vapor-phase chromatography and chemical degradation.The synthesis of the desoxypithecolobines 3a and 30 and their tetratosylates l l a and 110 is described. A comparison of these compounds with the corresponding "natural" mixtures by thin-layer chromatography in several systems, infrared, nuclear magnetic resonance, and mass spectrometry was found to support strongly the conclusions reached by the previous degradative work. Canadian Journal of Chemistry, 46, 3617 (1968) In the second communication (1) of this series we have shown that the "alkaloid pithecolobine" is in fact a mixture of homologues and analogues represented by the general formula 1.In this mixture we have rigorously demonstrated the presence of l a and we have shown that a significant proportion of compounds with m = 1 is present., As a necessary prerequisite of the synthetic studies to be described in the sequel, we wished to have at least a semiuuantitative estimate of the obtained from the Hofmann degradation of pithecolobine. We have shown in our second communication (1) that the Hofrnann degradation of pithecolobine yields besides a mixture of neutral unsaturated amides, the lactone 2 by internal displacement. Hydrogenation and hydrolysis of the unsaturated amides gave ndodecanoic acid contaminated by some n-tridecanoic and n-tetradecanoic acid. We have now determined quantitatively the proportions of these three acids in the mixture by v.p.c. of the methyl esters. .The result was as follows: C-12 acid, 65%; C-13 acid, 4%; C-14 acid, 30%. The quantities of lactone 2 and unsaturated amides obtained in the experiment were 122 mg and 391 mg, respectively. CH3-(CH2)aQo 2main components in the pithecolobine mixture.' From these results it is clear that a minimum It was possible to achieve such a crude analysis by of 24% of the pithecolobines is c o m p o u n~ la ~a~o r -p h a s e (v.P.c.) of straight (m = 3, 11 = 6), a further 49% are other C-22 chain acids (in the form of their methyl esters) (in + = g) pithecolobines (including possibly some more l a which did not yield the lactone 'Vapor-phase chromatography and other methods of 2, but gave a normal ~~f~~~~~ degradation); separation on the alkaloids and their derivatives were repeatedly tried and failed. For personal use only.

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Die Struktur des Spermin‐Alkaloides Aphelandrin aus Aphelandra squarrosa NEES. 170. Mitteilung über organische Naturstoffe

Dätwyler

Bosshardt

Bernhard

et al. 1978

Helvetica Chimica Acta

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The structure of the spermine alkaloid aphelandrine from Aphelandra sguarrosa NEES SummaryThe new spermine alkaloid aphelandrine (2) has been isolated from Aphelandra squarrosa NEES. By oxidation of 2 with KMn04 followed by methylation (CH2N2) 12 and 14 could be prepared (Scheme 2). Fusion of 2 with KOH yielded spermine (1) whereas hydrolysis of 2 in hot hydrochloric acid results in lacton 17, the structure of which could be elucidated by comparison with a synthetically prepared model compound (Scheme 3). The benzylic bonds N (lo), C (1 1) as well as 0 (16), C (17) of 2 could be cleaved by hydrogenolysis (compare 23 and 26; Scheme 4). The elucidation of the correct linkage of the spermine moiety with the aromatic dicarboxylic acid is based mainly on chemical and spectroscopic evidence of the tetrahydro derivative 26, the Hofmann-degradation products 28,30 and 31 (Scheme 6) as well as the ester 35, prepared by partial hydrolysis of 2 (Scheme 7).

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Structure of pithecolobine. II

Abstract: The alkaloid of Samatzea satnatz Merr. Pithecolobine is shown to be a family of closely related anal logues of the general formula (13). The structure (9a) has been proved for one of these compounds.

Cited by 19 publications

References 3 publications

Evaluation of Antimicrobial and Antioxidant Properties of Pithecolobine Isolated fromAlbizia saman

Evaluation of Antimicrobial and Antioxidant Properties of Pithecolobine Isolated fromAlbizia saman

Structure of pithecolobine. III. The synthesis of the 1,5- and 1,3-desoxypithecolobines

Die Struktur des Spermin‐Alkaloides Aphelandrin aus Aphelandra squarrosa NEES. 170. Mitteilung über organische Naturstoffe

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