Prenylated compounds from Atalantia racemosa: isolation and synthesis of two pyranoflavones

Banerji, Asoke; Luthria, Devanand L.; Prabhu, Bharathi R.

doi:10.1016/0031-9422(88)80782-9

Cited by 29 publications

(14 citation statements)

References 7 publications

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“…From a more polar fraction of the leaf extract, another flavone (6) with similar UV and NMR spectra was isolated, with the only difference being the replacement of the methoxyl group by a hydroxyl group. Compound 6 turned out to be the already known atalantoflavone, isolated from different sources of the Aurantioideae, like Atalantia racemosa, [25] and Citrus limonia [26] (in this paper called limonianin), but also from the legume Ulex europaeus ssp. europaeus.…”

Section: Resultsmentioning

confidence: 98%

Complete ¹H and ¹³C NMR data assignment of new constituents from Severinia buxifolia

Bacher

Brader

Greger

et al. 2009

Magnetic Reson in Chemistry

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Section: Resultsmentioning

confidence: 98%

Complete ¹H and ¹³C NMR data assignment of new constituents from Severinia buxifolia

Bacher

Brader

Greger

et al. 2009

Magnetic Reson in Chemistry

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“…Based on 1 H-, 13 C-NMR and EI-MS data as well as comparison to spectral data from the literature these compounds were identified as 3,5,4'-trimethoxy-4-prenylstilbene (1) [11], 4-methoxyderricidine (2) [11], 4-hydroxylonchocarpine (4) [11], 4-methoxylonchocarpine (5) [11], 4'-hydroxyisolonchocarpine (7) [12], 4'-methoxyisolonchocarpine (8) [13], 3',4'-methylenedioxy-7-methoxyflavone (10) [14] and 2,2-dimethylchromone-5,4'-dihydroxy-5'-methoxyflavone (11) [15]. The hexane extract from branches yielded two known flavonoids which were identified by the methods mentioned above as lonchocarpine (3) [11] and 3',4',7-trimethoxyflavone (9) [16].…”

Section: Isolation and Identification Of Flavonoids From D Duckeana mentioning

confidence: 99%

Isolation of Flavonoids from Deguelia duckeana and Their Effect on Cellular Viability, AMPK, eEF2, eIF2 and eIF4E

et al. 2016

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Preparations of Deguelia duckeana, known in Brazil as timbó, are used by indigenous people to kill fish. Reinvestigation of its extracts resulted in the isolation and identification of 11 known flavonoids identified as 3,5,4'-trimethoxy-4-prenylstilbene (1), 4-methoxyderricidine (2), lonchocarpine (3), 4-hydroxylonchocarpine (4), 4-methoxylonchocarpine (5), 5-hydroxy-4',7-dimethoxy-6-prenylflavanone (6), 4'-hydroxyisolonchocarpine (7), 4'-methoxyisolonchocarpine (8), 3',4',7-trimethoxyflavone (9), 3',4'-methylenedioxy-7-methoxyflavone (10), and 2,2-dimethyl-chromone-5,4'-hydroxy-5'-methoxyflavone (11). Except for 1, 3, and 4 all of these flavonoids have been described for the first time in D. duckeana and the flavanone 6 for the first time in nature. Compounds 2, 3, 4, 7, 9, and 10 were studied for their potential to induce cell death in neuronal SK-N-SH cells. Only the chalcone 4 and the flavanone 7 significantly induced lactate dehydrogenase (LDH) release, which was accompanied by activation of caspase-3 and impairment of energy homeostasis in the MTT assay and may explain the killing effect on fish. Interestingly, the flavone 10 reduced cell metabolism in the MTT assay without inducing cytotoxicity in the LDH assay. Furthermore, the flavonoids 2, 3, 4, 7, and 10 induced phosphorylation of the AMP-activated protein kinase (AMPK) and the eukaryotic elongation factor 2 (eEF2). The initiation factor eIF4E was dephosphorylated in the presence of these compounds. The initiation factor eIF2alpha was not affected. Further studies are needed to elucidate the importance of the observed effects on protein synthesis and potential therapeutic perspectives.

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“…2 Pyranoflavones 5-6 were isolated from Atalantia racemosa. 3 Pyranoflavones 7-8 were isolated from Artocarpus chama or communis, evergreen trees distributed over tropical regions of Asia. 4 Pyranochalcones 9-13 have been isolated from Lonchocarpus utilus or subglaucescens distributed in tropical America, Africa, and the Caribbean islands.…”

mentioning

confidence: 99%

A New Route to the Synthesis of Pyranoflavone and Pyranochalcone Natural Products and their Derivatives

Lee¹,

Kim²

2006

Synthesis

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S y n t h e s i s o f P y r a n o f l a v o n e a n d P y r a n o c h a l c o n e N a t u r a l P r o d u c t s a n d t h e i r D e r i v a t i v e s Abstract: The total synthesis of biologically active pyranoflavone natural products 1 and 2 was carried out starting from 2H-pyran. The synthesis of pyranochalcone natural products, lonchocarpin (9) and 4-hydroxylonchocarpin (10), and their derivatives 30-32 is described. This synthetic route also provides biologically interesting materials such as b-tubaic acid (24), desmethyl isoencecalin (25), and isoencecalin (27).

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Prenylated compounds from Atalantia racemosa: isolation and synthesis of two pyranoflavones

Cited by 29 publications

References 7 publications

Complete ¹H and ¹³C NMR data assignment of new constituents from Severinia buxifolia

Complete ¹H and ¹³C NMR data assignment of new constituents from Severinia buxifolia

Isolation of Flavonoids from Deguelia duckeana and Their Effect on Cellular Viability, AMPK, eEF2, eIF2 and eIF4E

A New Route to the Synthesis of Pyranoflavone and Pyranochalcone Natural Products and their Derivatives

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Prenylated compounds from Atalantia racemosa: isolation and synthesis of two pyranoflavones

Cited by 29 publications

References 7 publications

Complete 1H and 13C NMR data assignment of new constituents from Severinia buxifolia

Complete 1H and 13C NMR data assignment of new constituents from Severinia buxifolia

Isolation of Flavonoids from Deguelia duckeana and Their Effect on Cellular Viability, AMPK, eEF2, eIF2 and eIF4E

A New Route to the Synthesis of Pyranoflavone and Pyranochalcone Natural Products and their Derivatives

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Complete ¹H and ¹³C NMR data assignment of new constituents from Severinia buxifolia

Complete ¹H and ¹³C NMR data assignment of new constituents from Severinia buxifolia