A New Diels−Alder-Type Adduct Flavonoid from <i>Dorstenia barteri</i>

Tsopmo, Apollinaire; Téné, Mathieu; Kamnaing, Pierre; Ayafor, J. Foyere; Sterner, Olov

doi:10.1021/np990109o

Cited by 20 publications

(11 citation statements)

References 9 publications

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“…Phytochemical screening of the extracts showed the occurrence of flavonoids, terpenes and sterols. Flavonoids and polyphenolic compounds have been reported from many Dorstenia species (Tsopmo et al, 1998(Tsopmo et al, ,1999Dufall et al, 2003;Kansci et al, 2003;Abegaz et al, 2004;Ngameni et al, 2004). They occur as monoprenylated, diprenylated and geranylated derivatives including chalcones and other flavonoids.…”

Section: Discussionmentioning

confidence: 99%

Antinociceptive and anti-inflammatory effects of Dorstenia barteri (Moraceae) leaf and twig extracts in mice

Omisore

Adewunmi

Iwalewa

et al. 2004

Journal of Ethnopharmacology

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Section: Discussionmentioning

confidence: 99%

Antinociceptive and anti-inflammatory effects of Dorstenia barteri (Moraceae) leaf and twig extracts in mice

Omisore

Adewunmi

Iwalewa

et al. 2004

Journal of Ethnopharmacology

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“…These were subjected to further purification by MPLC. Eventually, 150 mg of 1 were isolated after additional purification by Sephadex LH‐20 GPC 19. Similarly, Boyom and co‐workers isolated 15 mg from 450 g of powdered twigs,20 and Akihisa et al isolated 30 mg from 300 g of dried plant material 16.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Isobavachalcone and Some Organometallic Derivatives

et al. 2012

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Isobavachalcone [2′,4,4′‐trihydroxy‐3′‐(3″‐methyl‐2″‐butenyl)chalcone, 1] is a prenylated chalcone that has broad biological activity, in particular against neuroblastomas, the most common cancer in infancy. It is currently commercially available at a cost of $190/mg by extraction from Psoralea corylifolia and a number of other African and Asian plants. Several synthetic routes have been explored, and the most efficient procedure involves the palladium‐catalysed Stille coupling of 3‐iodo‐2,4‐bis(methoxymethoxy)acetophenone (25) with prenyltributyltin, Claisen–Schmidt condensation with 4‐(methoxymethoxy)benzaldehyde to form the triply MOM‐protected prenylchalcone 27 and finally deprotection with 2 M HCl in methanol to form isobavachalcone in an overall yield of 15 % over five steps. The X‐ray crystal structures of 2,4‐dihydroxy‐3‐iodoacetophenone (21) and of several prenylated chalcones are reported, including the elucidation of their hydrogen‐bonding networks in the solid state. The synthetic route has been extended to include organometallic derivatives in which the 4‐(methoxymethoxy)benzaldehyde used in the Claisen–Schmidt condensation has been replaced by formylferrocene, formylruthenocene or (η5‐formylcyclopentadienyl)(η4‐tetraphenylcyclobutadiene)cobalt to form the corresponding analogues of isobavachalcone containing organometallic sandwich moieties.

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“…23 To the best of our knowledge, no pharmacological studies have yet been made on this plant. While a previous phytochemical investigation of the same taxon afforded: 5,7,4'-trihydroxy-8-prenylflavone, isobavachalcone (1), stipulin (5) and bichalcone, 12 only isobavachalcone (1) and stipulin (5) were isolated again from this species in our study, and this variation observed in the chemical constitution may potentially be accounted for by the climatic condition, the period and area of plant collection.…”

Section: Introductionmentioning

confidence: 41%

“…Flavonoids, particularly 4-hydroxylonchocarpin (2) isolated from D. mannii, 10 are good chemopreventive molecules against ovarian cancer cell growth. Recently, isobavachalcone (1) and dorsmannin A (6) isolated from D. barteri Bureau 12 and D. mannii, 10 exhibited inhibitory effects on skin tumor promotion in an in vivo two-stage mouse skin carcinogenesis test. 13 As part of a screening program on active ingredients isolated from Dorstenia species and other natural products having antitumor properties, the aim of the present investigation is to explore the potential inhibitory effect of chalcones isolated from the twigs of D. barteri var.…”

Section: Introductionmentioning

confidence: 99%

Inhibition of matrix metalloproteinase-2 secretion by chalcones from the twigs of Dorstenia barteri Bureau

Ngameni¹,

Touaibia²,

Belkaid³

et al. 2006

Arkivoc

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Chalcones and their analogs were extracted from the twigs of Dorstenia barteri and investigated for their capacity to inhibit matrix metalloproteinase (MMP)-2 secretion from brain tumorderived U87 glioblastoma cells. Among all tested compounds, potent inhibitory activities were recorded for chalcones 1, 4, 5, and 6 and to a lesser extent for 2 and 3. Semi-synthetic derivatives 7-9 displayed low (<30%) MMP-2 secretion inhibitory activity at concentrations ranging from 0.025 to 250 µM. Chalcones 1, 4, 5, and 6 were found to be more active in comparison to the documented MMP secretion inhibitors chlorogenic acid (CHL) and epigallocatechin-3-gallate (EGCg). Hydrogenation of 1 and acid-catalyzed cyclization of 3 were performed, thus generating three semi-synthetic derivatives (7-9). The newly synthesized flavanone 7 (cycloglabrol) and its chalcone analog 8 (isocycloglabrol) exhibited low MMP-2 secretion inhibitory activity with 30% inhibition at 250 µM. The activity of Dorstenia barteri crude extracts could be attributable to the high concentration of prenylated chalcones and more specifically to stipulin 5. Altogether, the structure-activity relationships established indicated that the hydroxyl, 2,3-double bond, the prenyl group, and its positioning could account for their role in inhibiting MMP-2 secretion, a process involved in extracellular matrix degradation and brain tumor progression.

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A New Diels−Alder-Type Adduct Flavonoid from Dorstenia barteri

Cited by 20 publications

References 9 publications

Antinociceptive and anti-inflammatory effects of Dorstenia barteri (Moraceae) leaf and twig extracts in mice

Antinociceptive and anti-inflammatory effects of Dorstenia barteri (Moraceae) leaf and twig extracts in mice

Synthesis of Isobavachalcone and Some Organometallic Derivatives

Inhibition of matrix metalloproteinase-2 secretion by chalcones from the twigs of Dorstenia barteri Bureau

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