α-Hydroxydihydrochalcones and related 1,3-diarylpropan-2-ones from Xanthocercis zambesiaca

Bezuidenhout, S. Catherine; Bezuidenhoudt, Barend C. B.; Ferreira, Daneel

doi:10.1016/0031-9422(88)80154-7

Cited by 12 publications

(5 citation statements)

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“…The 1 H-NMR spectrum of the acetyl derivative, 13a , showed three singlets at δ 2.29, 2.36 and 2.42 corresponding to the tri- O -acetyl derivative. Other 1 H-NMR data for 13a ( Table 3 ) were in good agreement with those reported for an isoflavone isolated as acetate from Xanthocercis zambesiaca [ 17 ].…”

Section: Resultssupporting

confidence: 85%

“…The triterpenoids were readily identified as lupeol ( 1 ), lupenone ( 2 ), 28-hydroxylup-20(29)-en-3-one ( 3 ) and betulin ( 4 ) [ 4 , 6 , 7 , 8 ] by a GC-MS library search. Isoflavonoids were identified by comparison with literature data and descriptions as 8- O -methylretusin (7-hydroxy-8,4’-dimethoxyisoflavone) ( 5 ) [ 9 , 10 ], 7-hydroxy-5,6,4’-trimethoxyisoflavone ( 6 ) [ 11 , 12 ], afrormosin (7-hydroxy-6,4’-dimethoxyisoflavone) ( 8 ) [ 13 ], 7-hydroxy-8,3’,4’-trimethoxyisoflavone ( 9 ) [ 14 ], 7,3’-dihydroxy-8,4’-dimethoxyisoflavone ( 10 ) [ 14 , 15 ], odoratin (7,3’-dihydroxy-6,4’-dimethoxyisoflavone) ( 11 ) [ 16 ], 7,8,3’-trihydroxy-4’-methoxyisoflavone ( 13 ) [ 17 ], 7,8,3’-trihydroxy-6,4’-dimethoxy-isoflavone ( 15 ) [ 18 ], dipteryxin (7,8-dihydroxy-6,4’-dimethoxyisoflavone) ( 17 ) [ 15 ]. The chalcone was identified as isoliquiritigenin (4,2’,4’-trihydroxychalcone) ( 7 ) [ 19 ], the aurone as sulfuretin (6,3’,4’-trihydroxyaurone) ( 14 ) [ 20 ], and the phenolic compounds as vanillic acid ( 12 ) [ 21 ], vanillin ( 16 )[ 21 ], and protocatechuic acid ( 18 ) [ 22 ].…”

Section: Resultsmentioning

confidence: 99%

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Chemical Constituents of the Bark of Dipteryx alata Vogel, an Active Species against Bothrops jararacussu Venom

et al. 2010

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The effect of four sub-extracts prepared from the lyophilized hydroalcoholic bark of Dipteryx alata (Leguminosae-Papilionoideae) dissolved in a methanol-water (80:20) mixture through a liquid-liquid partition procedure has been investigated against the neuromuscular blockade of the venom of the snake Bothrops jararacussu. The active CH2Cl2 sub-extract has been extensively analyzed for its chemical constituents, resulting in the isolation of four lupane-type triterpenoids: lupeol (1), lupenone (2), 28-hydroxylup-20(29)-en-3-one (3), betulin (4), nine isoflavonoids: 8-O-methylretusin (5), 7-hydroxy-5,6,4’-trimethoxyisoflavone (6), afrormosin (8), 7-hydroxy-8,3’,4’-trimethoxyisoflavone (9), 7,3’-dihydroxy-8,4’-dimethoxyisoflavone (10), odoratin (11), 7,8,3’-trihydroxy-4’-methoxyisoflavone (13), 7,8,3’-trihydroxy-6,4’-dimethoxyisoflavone (15), dipteryxin (17), one chalcone: isoliquiritigenin (7), one aurone: sulfuretin (14) and three phenolic compounds: vanillic acid (12), vanillin (16), and protocatechuic acid (18). Their chemical structures were elucidated on the basis of spectroscopic analysis, including HRMS, 1D- and 2D-NMR techniques.

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Section: Resultssupporting

confidence: 85%

Section: Resultsmentioning

confidence: 99%

Chemical Constituents of the Bark of Dipteryx alata Vogel, an Active Species against Bothrops jararacussu Venom

et al. 2010

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“…Biosynthetically, substitution at the 5 and 7 positions occur readily because of the polyketide pathway, however species within the Sophoreae have also been popularly substituted at the 7 and 8 positions as well as at the 3' and 4' positions on the phenyl ring (Harper et al, 1976;Albuquerque et al, 1981;Bezuidenhout et al, 1988), consistent with the isoflavones isolated from C. aurea in this work. It is highly likely that the isoflavones 3-5 follow the same biosynthetic pathway and most probable that 1 and 2 is also linked to this pathway prior to dehydroxylations and demethoxylations taking place en route to 3-5.…”

Section: Resultssupporting

confidence: 73%

Isoflavones from <i>Calpurnia aurea</i> subsp. <i>Aurea</i> and their Anticancer Activity

Korir¹,

Kiplimo²,

Crouch³

et al. 2014

Afr. J. Trad. Compl. Alt. Med.

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Background: Calpurnia aurea is an African medicinal plant used in many countries in Africa to treat a range of medical conditions or disorders. Extracts of the plant were shown to be active in antibacterial and antioxidant assays as well as against lice, ticks and maggots. The aim of the study was to isolate the phytochemical constituents from the plant and to test them in appropriate bioassays dependent on the compounds isolated in order to provide a rationale for the use of the plant in ethno-medicine or to provide some information on its constituents. Materials and methods:The stem and bark of the plant was extracted with organic solvents of varying polarity and the extracts separated and purified using column chromatography. The isolated compounds were identified by NMR spectroscopy and the compounds were tested for their in vitro anticancer activity against breast (MCF7), renal (TK10) and melanoma (UACC62) human cell lines using an in house method developed at the CSIR, South Africa. Results: The isoflavones, 4′,5,7-trihydroxyisoflavone (1), 7,3′-dihydroxy-5′-methoxyisoflavone (2), 7-hydroxy-4′,8-dimethoxyisoflavone (3), 7-acetoxy-4′,8-dimethoxyisoflavone (4) and 3',7-dihydroxy-4′,8-dimethoxyisoflavone (5), a pterocarpan (3-acetoxy-9-methoxypterocarpan) and a quinolizidine alkaloid (calpurnine) were isolated from the stem and bark of Calpurnia aurea. The tetrasubstituted isoflavone 5 was found to be the most active in the three cell lines amongst all the compounds tested. This was followed by trisubstituted isoflavone 2. Conclusion: The isoflavones showed moderate activity against the renal, melanoma and breast cancer cell lines tested against, with the isoflavones 2 and 5 showing the best activity of the compounds tested. These isoflavones may have a synergistic effect with other anticancer drugs.

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“…Figure 1 shows the chemical structure of TM from D. alata [32], a compound also found in Xanthocercis zambesiaca (Baker) plant extract [34].…”

Section: Resultsmentioning

confidence: 99%

An Isoflavone from Dipteryx alata Vogel is Active against the in Vitro Neuromuscular Paralysis of Bothrops jararacussu Snake Venom and Bothropstoxin I, and Prevents Venom-Induced Myonecrosis

et al. 2014

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Snakebite is a neglected disease and serious health problem in Brazil, with most bites being caused by snakes of the genus Bothrops. Although serum therapy is the primary treatment for systemic envenomation, it is generally ineffective in neutralizing the local effects of these venoms. In this work, we examined the ability of 7,8,3'-trihydroxy-4'-methoxyisoflavone (TM), an isoflavone from Dipteryx alata, to neutralize the neurotoxicity (in mouse phrenic nerve-diaphragm preparations) and myotoxicity (assessed by light microscopy) of Bothrops jararacussu snake venom in vitro. The toxicity of TM was assessed using the Salmonella microsome assay (Ames test). Incubation with TM alone (200 μg/mL) did not alter the muscle twitch tension whereas incubation with venom (40 μg/mL) caused irreversible paralysis. Preincubation of TM (200 μg/mL) with venom attenuated the venom-induced neuromuscular blockade by 84% ± 5% (mean ± SEM; n = 4). The neuromuscular blockade caused by bothropstoxin-I (BthTX-I), the major myotoxic PLA 2 of this venom, was also attenuated by TM. Histological analysis of diaphragm muscle incubated with TM showed that most fibers were preserved (only 9.2% ± 1.7% were damaged; n = 4) compared to venom alone (50.3% ± 5.4% of fibers damaged; n = 3), and preincubation of TM with venom significantly attenuated the venom-induced damage (only 17% ± 3.4% of fibers damaged; n = 3; p < 0.05 compared to venom alone). TM showed no mutagenicity in the Ames test using Salmonella strains TA98 and TA97a with (+S9) and without (−S9) metabolic activation. These findings indicate that TM is a potentially useful compound for antagonizing the neuromuscular effects (neurotoxicity and myotoxicity) of B. jararacussu venom.

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α-Hydroxydihydrochalcones and related 1,3-diarylpropan-2-ones from Xanthocercis zambesiaca

Cited by 12 publications

References 13 publications

Chemical Constituents of the Bark of Dipteryx alata Vogel, an Active Species against Bothrops jararacussu Venom

Chemical Constituents of the Bark of Dipteryx alata Vogel, an Active Species against Bothrops jararacussu Venom

Isoflavones from <i>Calpurnia aurea</i> subsp. <i>Aurea</i> and their Anticancer Activity

An Isoflavone from Dipteryx alata Vogel is Active against the in Vitro Neuromuscular Paralysis of Bothrops jararacussu Snake Venom and Bothropstoxin I, and Prevents Venom-Induced Myonecrosis

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