Piliostigmin, a 2-phenoxychromone, and C-methylflavonols from Piliostigma thonningii

Ibewuike, Joseph C.; Ogundaini, A. O.; Ogungbamila, Francis O.; Martin, Marie‐Thérèse; Gallard, Jean‐François; Bohlin, Lars; Païs, M.

doi:10.1016/0031-9422(96)00367-6

Cited by 54 publications

(50 citation statements)

References 10 publications

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“…Caesalpiniaceae (Ajaiyeoba et al, 2008) or lupeol-based libraries from triterpenoid lupeol (Srinivasan et al, 2002) have been shown to display antimalarial activity. In addition, piliostigmin, a 2-phenoxychromone, quercetin, quercitrin, 6-C-methylquercetin 3-methyl ether, 6-C-methylquercetin 3,7,3'-trimethyl ether, 6,8-di-C-methylkaempferol 3-methyl ether and 6,8-di-C-methylkaempferol 3,7-dimethyl ether were isolated from the leaves of P. thonningii (Ibewuike et al, 1996). Similar C-methylated flavonols and the oxychromonol isolated from Piliostigma reticulatum showed antimicrobial activity and toxicity in brine shrimp lethality assay (Babajide et al, 2008).…”

Section: Resultsmentioning

confidence: 99%

In vitroantiplasmodial activity and toxicity assessment of some plants from Nigerian ethnomedicine

Abiodun

Gbotosho

Ajaiyeoba

et al. 2010

Pharmaceutical Biology

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Section: Resultsmentioning

confidence: 99%

In vitroantiplasmodial activity and toxicity assessment of some plants from Nigerian ethnomedicine

Abiodun

Gbotosho

Ajaiyeoba

et al. 2010

Pharmaceutical Biology

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“…The IR spectrum showed absorption bands for hydroxyl (3377 cm -1 ) and carbonyl (1633 cm -1 ) groups and aromatic functionalities (1599 and 1488 cm -1 , respectively). The 13 C NMR spectra ( 13 C NMR data revealed that compound 1 was composed of two 6-C-methylquercetin [10,11] moieties and a hexosyl residue.…”

Section: Esi-ms Exhibited a [M-h]mentioning

confidence: 99%

“…2) [10,11] Inspection of the signals of segment 2 revealed some structural characteristics of segment 1 and also suggested the presence of rings A and B. The major differences between segments 1 and 2 were in the ring C. Particularly, the signals assigned to two quaternary carbons [d C = 100.0 (C-2) and 90.6 (C-3)] and a carbonyl carbon [d C = 188.0 (C-4)] were observed, which indicated that the carbon skeleton of the ring C was converted into a dihydropyrone ring from a pyrone ring and new substituents were bound to C-2 and C-3 positions (both of them bearing oxygen atoms).…”

Section: Esi-ms Exhibited a [M-h]mentioning

confidence: 99%

Structure determination of baeckeins C and D from the roots of Baeckea frutescens

Jia

Zhou

Chen

et al. 2011

Magnetic Reson in Chemistry

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Baeckeins C (compound 1) and D (compound 2), a pair of new diastereomeric biflavonoids, were isolated from the roots of Baeckea frutescens. Their structures were elucidated on the basis of spectroscopic analysis, including HR-ESI-MS and one- and two-dimensional NMR spectra ((1)H and (13)C NMR, HSQC, HMBC, and ROESY). The absolute configurations of the 2,3-epoxide moiety for compounds 1 and 2 were determined by circular dichroism spectrometry combined with quantum chemical calculations.

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“…Mass spectrum [8]: 385 (26), 384 (100) [M] + , 369 (11), 341 (76), 330 (15), 329 (73), 328 (13), 311 (18), 297 (6), 275 (7), 260 (14), 259 (61), 245 (11), 233 (12), 232 (15), 217 (11), 203 (10), 179 (20), 150 (10), 110 (16), 97 (10), 69 (12). HRMS [8] HMBC, NOESY [10].…”

Section: Glyasperin Ementioning

confidence: 99%

“…Such unusual flavonoids have been isolated from plants of various families. Thus, 2-phenoxychromones are produced by plants of the Compositae [1, 2], Rosaceae [3,4], Berberidaceae [5], Caesalpiniaceae [6], and Fabaceae [7] families. Reports of 3-aryloxychromones isolated from natural sources are much less common.…”

Section: Natural Distributionmentioning

confidence: 99%

3-Phenoxychromones: Natural distribution, synthetic and modification methods, biological properties

2006

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UDC 547.972The literature on the natural distribution, synthetic and chemical transformation methods, and pharmacological properties of 3-phenoxychromones were reviewed.Flavonoids are one of the most widely distributed groups of phenolic compounds that have C 6 -C 3 -C 6 structural fragment in common. The flavonoid molecule consists of two phenyl rings joined by a three-carbon aliphatic chain. Most flavonoids can be viewed as chromone or chromane derivatives that contain aryl radicals in the 2-, 3-, or 4-position.Compounds in which the aryl substituent is bonded to the chromone nucleus through an O atom and that are called phenoxychromones are sometimes encountered among the natural flavonoids. The phenoxyl substituent can be located in the 2-or 3-position of the chromone system. Derivatives of 3-aryloxychromone with structures close to those of isoflavones are interesting because they have a variety of pharmacological properties.Although such compounds are certainly interesting, reviews of synthetic methods and chemical and pharmacological properties have not appeared. NATURAL DISTRIBUTIONCompounds based on both 2-and 3-phenoxychromone have been isolated from natural sources. Such unusual flavonoids have been isolated from plants of various families. Thus, 2-phenoxychromones are produced by plants of the Compositae [1, 2], Rosaceae [3, 4], Berberidaceae [5], Caesalpiniaceae [6], and Fabaceae [7] families. Reports of 3-aryloxychromones isolated from natural sources are much less common. In contrast with 2-phenoxychromones, derivatives of 3-phenoxychromone are rarely encountered secondary metabolites and are synthesized only by plants of the Fabaceae family. At present only five comopunds based on the 3-phenoxychromone skeleton have been isolated from natural sources.Glyasperin E (1) was the first natural 3-phenoxychromone to be isolated and was a minor component from Glycyrrhiza aspera (Fabaceae) roots. It is widely used in Chinese folk medicine [8,9]. Extracts of Erythrina variegata (Fabaceae) roots contained two derivatives of 3-phenoxychromone, eryvarins F (2) and G (3) [10].The 3-phenoxychromone skeleton provides the basis for (-)-13-homo-13-oxa-6a,12a-dehydrorotenone (4) and 13-homo-13-oxa-6a,12a-dehydrodeguelin (5), which were isolated from Lonchocarpus utilis and L. urucu (Fabaceae) root resin that has insecticidal activity and have structures similar to rotenoids [11].

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Piliostigmin, a 2-phenoxychromone, and C-methylflavonols from Piliostigma thonningii

Cited by 54 publications

References 10 publications

In vitroantiplasmodial activity and toxicity assessment of some plants from Nigerian ethnomedicine

In vitroantiplasmodial activity and toxicity assessment of some plants from Nigerian ethnomedicine

Structure determination of baeckeins C and D from the roots of Baeckea frutescens

3-Phenoxychromones: Natural distribution, synthetic and modification methods, biological properties

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