Isolation and characterisation of bergenin derivatives from Macaranga peltata

Ramaiah, Parimi Atchuta; Row, L. Ramachandra; Reddy, D. Narasimha; Anjaneyulu, A. S. R.; Ward, Robert S.; Pelter, Andrew

doi:10.1039/p19790002313

Cited by 41 publications

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“…The absence of a 1 H NMR signal for the isoprenyl double bond and upfield shifts of H-2″ (δ 3.73 ppm), H-4″ (δ 1.33 ppm) and H-5″ (δ 1.23 ppm), and the appearance of H-1″ as doublet of doublets at δ 2.90 and 2.53 ppm, all indicated that the isoprenyl group was cyclized with one of the phenolic oxygens. The hydroxylation of C-2″ was also apparent from its 13 The data presented to this point demonstrate the relative stereochemistry of compounds 1 -4, but do not establish their absolute stereochemistry. Fortunately this can be established by a comparison of CD spectra and of optical rotations between these compounds and the enantiomers of schweinfurthin F (2).…”

Section: Resultsmentioning

confidence: 69%

“…The presence of an isoprenyl group was indicated by 13 C NMR signals at δ 131.1 (C-3″), 124.6 (C-2″), 26.0 (C-5″), 23.3 (C-1″), and 17.9 ppm (C-4″). 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.…”

Section: Resultsmentioning

confidence: 99%

“…The flavonoid alnifoliol (5) The known compounds vedelianin (6), 22 bonanniol A (7), 27 diplacol (8), 28 , 29 bonannione A (9), 27 and diplacone (10, also known as nymphaeol A) 30,31 were also isolated, and their structures were determined based upon comparison of their 1 H NMR, 13 C NMR, and HRFABMS spectra to literature values. 22,26-31…”

Section: Resultsmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 69%

Section: Resultsmentioning

confidence: 99%

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

et al. 2007

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“…A phytochemical review of literatures indicates the genus Macaranga to be a rich source of the isoprenylated, geranylated and farnesylated flavonoids (Schutz et al, 1995;Jang et al, 2002;Phormmart et al, 2005;Kawakami et al, 2008;Thanh et al, 2012) and stilbenes (Beutler et al, 1998;Yoder et al, 2007;Thanh et al, 2012). Furthermore, more classes of secondary metabolites like terpenes (Salah et al, 2003;Jang et al, 2004;Phormmart et al, 2005;Kawakami et al, 2008), tannins (Lin et al, 1990;Gunawan-Puteri and Kawabata, 2010;Ngoumfo et al, 2008), coumarins (Sutthivaiyakit et al, 2002;Darmawan et al, 2012) and other types of compounds (Ramaiah et al, 1979;Ngoumfo et al, 2008;Matsunami et al, 2009;Zakaria et al, 2010) are known to be isolated from different species of the genus Macaranga. Flavonoids and stilbenes are regarded as the major constituents and are most likely responsible for most of the activities found in the plants of this genus.…”

Section: Introductionmentioning

confidence: 99%

Phytochemistry and pharmacology of the genus Macaranga: A review

Magadula¹

2014

J. Med. Plants Res.

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“…Fraction eluted with EtOAc (100%), EtOAc/MeOH (10%) and EtOAc/MeOH (20%) were combined affording bergenin (1) (1.02 g). Bergenin was purified by recrystallization from methanol and identified by comparison of its physical and spectroscopic data (IR, 1H and 13C NMR) with those reported in the literature (Ramaiah et al, 1979).…”

Section: Extraction and Isolation Of Bergenin (1)mentioning

confidence: 99%

Anti-inflammatory and non ulcerogenic activities of acetylbergenin

Borges¹,

Aguiar²,

Sousa³

et al. 2017

Afr. J. Pharm. Pharmacol.

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Endopleura uchi (Huber) Cuatrec. (Humiriaceae), the Brazilian Amazon plant, is used in folk medicine to treat arthritis and gastric ulcer. Bergenin, one of the chemical constituents of E. uchi, has antiinflammatory properties. Its acetylation results in acetylbergenin, which is extracted to investigate its potential anti-inflammatory and antiulcer properties using an assay for croton oil-induced ear edema, rat paw edema induced by carrageenan and dextran, carragenin-induced peritonitis, and stress-induced gastric ulcer. In ear erythema induced by croton oil, acetylbergenin presented a significant 75.60% inhibition (p<0.001). The oral administration of 6.8 mg/kg of acetylbergenin significantly inhibited the carrageenan-induced edema formation by 35.09% (p<0.05) and the dextran-induced edema by 33% (p<0.05). The migration of neutrophils toward the peritoneal cavity was inhibited in acetylbergenin (6.8 mg/kg) treated animals by 70% (p<0.01). In the stress-induced gastric ulcer, acetylbergenin inhibited 78.55% of gastric lesions. The results suggest that, the anti-inflammatory action of acetylbergenin appears to be dependent on cyclooxygenase (COX-2) inhibition. Furthermore, although the antiinflammatory activity of acetylbergenin is a characteristic of nonsteroidal compounds, it causes little deleterious interference in the gastric mucosa.

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Isolation and characterisation of bergenin derivatives from Macaranga peltata

Cited by 41 publications

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

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

Phytochemistry and pharmacology of the genus Macaranga: A review

Anti-inflammatory and non ulcerogenic activities of acetylbergenin

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Isolation and characterisation of bergenin derivatives from Macaranga peltata

Cited by 41 publications

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

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

Phytochemistry and pharmacology of the genus Macaranga: A review

Anti-inflammatory and non ulcerogenic activities of acetylbergenin

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

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