The caulindoles: dimeric prenylindoles from Isolona cauliflora

Makangara, John J.; Henry, Leonia; Jonker, Stephan A.; Nkunya, Mayunga H.H.

doi:10.1016/j.phytochem.2003.10.010

Cited by 34 publications

(21 citation statements)

References 13 publications

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“…The caulindoles can be perceived as products of Diels-Alder-type cycloaddition reactions between the presumed monomeric prenyled indoles acting as the diene and dienophile [50]. Apparently, the regiochemistry of the caulindoles indicates that biosynthetically these compounds would indeed have been formed through Diels-Alder-type cycloaddition reactions involving simpler prenylated indoles as dienes and dienophiles, in accordance with Frontier Orbital Theory (FOT) predictions [53].…”

Section: Prenylated Indolessupporting

confidence: 54%

“…These compounds have been isolated from the Annonaceae genera Annonidium [46], Asteranthe [47], Hexalobus [48], Isolona [49][50][51], Monodora [51], and Uvaria [52]. They consist of mono-and bis-prenylated isomers, as well as dimeric bis-prenylated indoles, some of the compounds having interesting antifungal and other biological activities.…”

Section: Prenylated Indolesmentioning

confidence: 99%

“…Diprenylated indoles that are collectively referred to as the hexalobines have been isolated from I. maitlandii as isomeric pairs [49], the compounds for the first time having been isolated from Hexalobus species (Annonaceae) [48]. From I. cauliflora, we recently isolated the bis-prenylated indole caulidine A (52), the partially oxidized bis-prenylated indole caulidine B (53) and the prenylated formylindole 54, and four dimeric prenyl indoles that occurred as diastereomeric pairs, namely, the caulindole A-D (55-58), some of which exhibited antifungal activity [50].…”

Section: Prenylated Indolesmentioning

confidence: 99%

“…However, it is interesting to note that both the exo (caulindole A and caulindole C) and endo products (caulindole B and caulindole D) were obtained from I. cauliflora in nearly the same proportions [50]. This and the fact that caulindole A was obtained as an optically active compound ([α]D = +13.95°, c = 0.17, CHCl 3 ) complicates further the presumed biosynthesis of caulindoles.…”

Section: Prenylated Indolesmentioning

confidence: 99%

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Unusual metabolites from some Tanzanian indigenous plant species

Nkunya

2005

Pure and Applied Chemistry

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In this paper, the chemistry of some unusual natural products that were isolated from various Tanzanian indigenous plant species during the past 20 years is reviewed. Among the compounds covered in this review are cyclohexane epoxides; heptane derivatives; oxygenated pyrenes; phenanthrene derivatives; flavonoids with uncommon structural frameworks; mono-, bis-, and dimeric prenylated indoles; and variously substituted mono-, sesqui-, and diterpenoids.

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Section: Prenylated Indolessupporting

confidence: 54%

Section: Prenylated Indolesmentioning

confidence: 99%

Section: Prenylated Indolesmentioning

confidence: 99%

Section: Prenylated Indolesmentioning

confidence: 99%

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Unusual metabolites from some Tanzanian indigenous plant species

Nkunya

2005

Pure and Applied Chemistry

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“…The structural assignment was also supported by comparison of its 13 C NMR spectrum with that of 4-hydroxy-2-methoxy-cinnamic acid. 20 A number of 3,5-and 3,6-diprenylated indoles have been reported for the Annonaceae genera Isolona, [21][22][23] Uvaria, 22 Annonidium, 24 Monodora, 25 Hexalobus, 26 Asteranthe, 27 Greenwayodendron, 28 and Polyalthia. 29 However, there are only a few examples of 3-, 5-, 6-and 7-and 3,7-prenylated indoles reported in the Rutaceae genera Raputia, 14 Esenbeckia, 30,31 Murraya, [32][33][34] Merrillia 35 and Glycosmis.…”

Section: Resultsmentioning

confidence: 99%

Prenylindole alkaloids from Raputia praetermissa (Rutaceae) and their chemosystematic significance

Rosas¹,

Veiga²,

Fernandes³

et al. 2011

J. Braz. Chem. Soc.

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O extrato diclorometano do caule de Raputia praetermissa levou ao isolamento de quatro compostos novos, 4-desóxi-raputindol C (1), raputimonoindol A-B (2, 3) e hexadecanil 2-hidróxi-4-metóxi-cinnamato (5), juntamente com os alcalóides 5-(4-metóxi-metilfuran-2-il)-1H-indol (raputimonoindol C), furoquinolinos maculosidine, robustine, evolitrine e dictamnine. O estudo do extrato hexano levou ao isolamento de N-metil-4-metóxi-quinolin-2(1H)-ona, skimmianina, cicloartenona, sitosterol, stigmasterol e sitostenona. Os alcalóides antranílicos isolados indicam que o gênero possui afinidade química relevante com aqueles da tribo Cusparieae, mas difere de Neoraputia devido à ausência de alcalóides prenilindois neste último, cujas espécies foram anteriormente incluídas em Raputia.The dichloromethane extract from the stems of Raputia praetermissa afforded four new compounds, 4-deoxyraputindole C (1), raputimonoindole A-B (2, 3), and hexadecanyl 2-hydroxy-4-methoxy-cinnamate (5), besides the alkaloids 5-(4-methoxymethylfuran-2-yl)-1H-indole (raputimonoindole C), furoquinolines maculosidine, robustine, evolitrine and dictamnine. The hexane extract yielded N-methyl-4-methoxyquinolin-2(1H)-one, skimmianine, cycloartenone, sitosterol, stigmasterol and sitostenone. The anthranilate alkaloid content indicates that the genus is strongly related to those included in Cusparieae tribe, but differs from Neoraputia by the absence of prenylindole alkaloids in the late, whose species have previously been placed in Raputia. Previous investigations of Neoraputia reported the presence of eleven polymethoxylated flavonoids, six flavones, three 5,6-(2",2"-dimethylpyrano)flavones, one 6,7-(2",2"-dimethylpyrano)flavone and one flavanone from N. alba (Engler) Emmerich; 6,7 five polymethoxylated flavones and two flavanones, 2'-hydroxy-3,4,4',5,6'-pentamethoxychalcone, three 5',6'-(2",2"-dimethylpyrano)-polymethoxylated chalcones from N. magnifica var. magnifica (Engler) Emmerich; 8,9 ten polymethoxylated flavonoids, six flavones, three 6,7-(2",2"-dimethylpyrano) flavones and one 6-(3"-hydroxy,3"-methyl-trans-but-1"-enyl)flavone from N. paraensis. Keywords10,11 A reinvestigation of N. paraensis searching for alkaloids afforded flindersine, skimmianine, 8-methoxyflindersine and dictamnine.12 Rosas et al. 1347 Vol. 22, No. 7, 2011 C-glycosylflavones were also reported from N. paraensis, 13 which was cited as Raputia paraensis, but this species was transferred to Neoraputia by Emmerich. 1The first investigation about the chemistry of Raputia reported the presence of cyclopentyl bisindole alkaloids raputiindoles A-D from R. simulans Kllunki. 14 In this paper we report a phytochemical study on R. praetermissa Pirani & Kallunki, and the chemosystematic significance of isolated compounds is discussed in order to clarify the relationships between Raputia and Neoraputia. Results and DiscussionThe dichloromethane extract from the stems of Raputia praetermissa afforded four prenylindole alkaloids (1-4), a cinnamic acid derivative (5) (Figure 1 -5b), a...

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Rare Bisindole Alkaloids from the Amazonian Tree Raputia simulans

Vougogiannopoulou

Travasarou

Fokialakis

et al. 2014

Chemistry & Biodiversity

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The stem bark of Raputia simulans (Rutaceae) has been reported to contain simple and dimeric indole alkaloids. Further phytochemical investigation of R. simulans stem bark resulted in the isolation of three new alkaloids. These compounds represent a relatively new category of dimeric indole alkaloids with a cyclohexene moiety in their core. Their structure elucidations were based on NMR and HR-MS techniques, while structural aspects concerning their relative configuration were investigated using molecular mechanics calculations and NOESY experiments.

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The caulindoles: dimeric prenylindoles from Isolona cauliflora

Cited by 34 publications

References 13 publications

Unusual metabolites from some Tanzanian indigenous plant species

Unusual metabolites from some Tanzanian indigenous plant species

Prenylindole alkaloids from Raputia praetermissa (Rutaceae) and their chemosystematic significance

Rare Bisindole Alkaloids from the Amazonian Tree Raputia simulans

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