Vedelianin, a hexahydroxanthene derivative isolated from Macaranga vedeliana

Thoison, Odile; Hnawia, Edouard; Guiéritte-Voegelein, Françoise; Sévenet, Thierry

doi:10.1016/0031-9422(92)80315-6

Cited by 51 publications

(52 citation statements)

References 4 publications

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“…The 1 H NMR spectrum of 3, C 25 H 26 O 6 [M] + 422, showed a monoterpene unit of a cyclized geranyl group. The proton signals appeared at H 0.88, 0.98, and 1.51 (each 3H, s), whereas resonances at H 1.16 (1H, m), 1.70 (1H, m), and 2.01 (2H, m) were attributed to a pair of aliphatic methylenes, and the signal of additional resonances H 2.28 (1H, t, J=7.0 Hz) corresponded to an allylic methine, H 2.66 (1H, dd, J=7.0, 13.5 Hz) and 2.87 (1H, dd, J=6.5, 13.5 Hz) resulted from a benzylic methylene, and the signal of H 5.23 (1H, br s) was for an olefinic methine (Thoison et al, 1992). An HMBC experiment ( Fig.…”

Section: Resultsmentioning

confidence: 98%

Antioxidant flavonoids from the rhizomes of Helminthostachys zeylanica

et al. 2003

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Section: Resultsmentioning

confidence: 98%

Antioxidant flavonoids from the rhizomes of Helminthostachys zeylanica

et al. 2003

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“…The three other methyl carbons resonated at δ 29.4 (C-12), 22.0 (C-13) and 16.5 ppm (C-11), and the methoxy carbon resonated at δ 56.5 ppm. Signals for three oxygenated sp 3 carbons (C-2, C-4a, and C-3) were present in the spectrum at δ 78.8, 78.1, and 71.8 ppm, respectively, and the carbons of the AA′ benzene ring of the stilbene were observed at δ 157.3 ppm for the hydroxylated carbons (C-5′ and C-7′) and δ 105.8 ppm for the hydrogenated carbons (C-4′ and C-8′).…”

Section: Resultsmentioning

confidence: 99%

Antiproliferative Prenylated Stilbenes and Flavonoids from Macaranga alnifolia from the Madagascar Rainforest^,1

et al. 2007

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Bioassay-guided fractionation of an extract of the fruit of Macaranga alnifolia from Madagascar led to the isolation of four new prenylated stilbenes, schweinfurthins E-H (1-4), and one new geranylated dihydroflavonol, alnifoliol (5). The known prenylated stilbene, vedelianin (6), and the known geranylated flavonoids, bonanniol A (7), diplacol (8), bonannione A (9) and diplacone (10), were also isolated. All ten compounds were tested for antiproliferative activity in the A2780 human ovarian cancer cell line assay. Vedelianin (IC 50 = 0.13 µM) exhibited the greatest activity among all isolates, while schweinfurthin E (IC 50 = 0.26 µM) was the most potent of the new compounds.The genus Macaranga is a large genus of the Euphorbiaceae family. Observation of Macaranga plants in their natural environment has revealed that they produce thread-like wax crystals on their ste ms, which make the slippery surfaces impassable for all insects except a species of ants known as "wax runners". Chemical analysis has indicated that terpenoids make up a majority of the wax bloom content that helps maintain this symbiotic relationship between plant and insect. 2 One of the more commonly studied species of this genus is M. tanarius, noted for its diterpenoid 3,4 and flavonoid 5-7 content. Work has also been performed on the isolation and characterization of terpenes from M. carolinensis ,8 flavonoids from M. conifera 9 and M. denticulate ,10 chromenoflavones from M. indica , 11 clerodane diterpenes from M. monandra , 12 bergenin derivatives and polyphenols from M. peltata , 13 , 14 prenylflavones from M. pleiostemona , 15 a geranyl flavanone from M. schweinfurthii ,16 tannins from M. sinensis ,17 a rotenoid and other compounds from M. triloba , 18 and a geranylflavonol from M. vedeliana. 19 No phytochemical studies have been previously reported for M. alnifolia.

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“…5 When tested in the National Cancer Institute screen of 60 human cancer cell lines, those containing a hexahydroxanthene substructure as the ABC ring system showed an intriguing pattern of biological activity. Their unique fingerprint of activity does not parallel that of any chemotherapeutic agent in current clinical use, and approximates those of only a few, far more complex natural products (notably cephalostatins, 6 OSW-1, 7 ritterazines, 8 and stellettins 9 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of amide isosteres of schweinfurthin-based stilbenes

Stockdale

Beutler

Wiemer

2017

Bioorganic & Medicinal Chemistry

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The schweinfurthins are plant-derived stilbenes with an intriguing profile of anti-cancer activity. To obtain analogues of the schweinfurthins that might preserve the biological activity but have greater water solubility, a formal replacement of the central olefin with an amide has been explored. Two pairs of amides have been prepared, each containing the same hexahydroxanthene “left half” joined through an amide linkage to two different “right halves.” In each series, the amide has been inserted in both possible orientations, placing the carbonyl group on the tricyclic ABC ring system and the amine on the D-ring, or placing the amine on the hexahydroxanthene and the carbonyl group on the D-ring. The four new schweinfurthin analogues have been tested in the NCI 60 cell line screen, and in both cases the more active isomer carried the carbonyl group on the C-ring.

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Vedelianin, a hexahydroxanthene derivative isolated from Macaranga vedeliana

Cited by 51 publications

References 4 publications

Antioxidant flavonoids from the rhizomes of Helminthostachys zeylanica

Antioxidant flavonoids from the rhizomes of Helminthostachys zeylanica

Antiproliferative Prenylated Stilbenes and Flavonoids from Macaranga alnifolia from the Madagascar Rainforest^,1

Synthesis of amide isosteres of schweinfurthin-based stilbenes

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Vedelianin, a hexahydroxanthene derivative isolated from Macaranga vedeliana

Cited by 51 publications

References 4 publications

Antioxidant flavonoids from the rhizomes of Helminthostachys zeylanica

Antioxidant flavonoids from the rhizomes of Helminthostachys zeylanica

Antiproliferative Prenylated Stilbenes and Flavonoids from Macaranga alnifolia from the Madagascar Rainforest,1

Synthesis of amide isosteres of schweinfurthin-based stilbenes

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Antiproliferative Prenylated Stilbenes and Flavonoids from Macaranga alnifolia from the Madagascar Rainforest^,1