Bioactive steroidal alkaloid glycosides from Solanum aculeastrum

Wanyonyi, A. W.; Chhabra, S. C.; Mkoji, Gerald M.; Eilert, U.; Njue, Wilson

doi:10.1016/s0031-9422(01)00424-1

Cited by 80 publications

(77 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[26][27][28][29][30] In order to compare the relative stabilities of the epimeric structures 13/14, a molecular modeling study was implemented using the Spartan 06 for Linux program (Wavefunction, Inc.), see Supplementary Information. 31 The complete 1 H and 13 C chemical shift assignments of the signals of CH 3 , CH 2 , CH and C observed in the 1 H (including 1 H-1 H-COSY) and 13 C ({ 1 H} and DEPT) NMR spectra (including 2D experiments HMQC and HMBC) (Tables 1, 2, 3 and 4) and comparison with values described in the literature for solamargine (13) 26-29 and solasonine (16) 28,31 led to the proposition of the structures (25R) , 16) for the three steroidal glycoalkaloids isolated from this plant (Figure 1). Vol.…”

Section: Resultsmentioning

confidence: 99%

“…Comparative analysis of these data was used to suggest the two stereoisomers H-20b (13) and H-20a (14), since the 22aN and 22bN possibilities were eliminated considering the absence of 13 C signal corresponding to a methylene carbon CH 2 -23 at about d C 27 which is consistent with the 13 . [26][27][28][29][30] In order to compare the relative stabilities of the epimeric structures 13/14, a molecular modeling study was implemented using the Spartan 06 for Linux program (Wavefunction, Inc.), see Supplementary Information. 31 The complete 1 H and 13 28,31 led to the proposition of the structures (25R) , 16) for the three steroidal glycoalkaloids isolated from this plant (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

“…[26][27][28][29][30] In order to compare the relative stabilities of the epimeric structures 13/14, a molecular modeling study was implemented using the Spartan 06 for Linux program (Wavefunction, Inc.), see Supplementary Information. 31 The complete 1 H and 13 28,31 led to the proposition of the structures (25R) , 16) for the three steroidal glycoalkaloids isolated from this plant (Figure 1). The natural alkaloids 14 and 16 were treated with Ac 2 O/pyridine to yield the peracetyl derivatives 15 and 17.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Other chemical constituents isolated from Solanum crinitum Lam. (Solanaceae)

Cornelius

Carvalho

Alves

et al. 2010

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

(7), ácido 4-hidroxibenzoico (12), e quatro derivados do ácido cinâmico: cis-e trans-cumárico (10 e 11), cis-e trans-cumarato de etila (8 e 9), isolados de tricomas do fruto. Do extrato metanólico de frutos verdes foram isolados três alcalóides esteroidais glicosilados: solamargina (13), 20-epi-solamargina (14) e solasonina (16). Os derivados 3,5,7,4'-tetra-O-metil-kaempferol (4), 3,7,4'-tri-O-metil-kaempferol (5), 3,7,4'-tri-O-metil-5-Oacetil-kaempferol (6), peracetil-epi-solamargina (15) e peracetil-solasonina (17) foram sintetizados e estão sendo registrados pela primeira vez na literatura. As estruturas foram definidas através de análise de dados espectrométricos.The phytochemical investigation of Solanum crinitum Lam led to the isolation from the fruit trichomes of four flavonoids, tiliroside (1), astragalin (2), kaempferol (3), biochanin A-7- O-b-D-apiofuranosyl-(1→5)-b-D-apiofuranosyl-(1→6)-b-D-glucopyranoside (7), along with 4-hydroxybenzoic acid (12), and four cinnamic acid derivatives, cis-and trans-coumaric acids (10 and 11) and cis-and trans-ethyl coumarate (8 and 9). Three tri-glycosyl-steroidal alkaloids, solamargine (13), 20-epi-solamargine (14) and solasonine (16) were isolated from the methanolic extract of the green fruits. The derivatives 3,5,7,4'-tretra-O-methyl-kaempferol (4), 3,7,4'-tri-O-methyl-kaempferol (5), 3,7,4'-tri-O-methyl-5-O-acetyl-kaempferol (6), the peracetyl-episolamargine (15) and peracetyl-solasonine (17) were prepared. The structures were established through the analysis of their spectral data. The complete 1 H and 13 C NMR data assignments of the new peracetyl derivatives of the alkaloids were made.Keywords: Solanum crinitum, Solanaceae, steroidal glycoalkaloids, flavonoids, cinnamic acids Introduction Solanum (L) is the most representative genus of Solanaceae, containing about 1,500 species, and 5,000 epithets. It is widespread in tropical and subtropical regions of all the world, but its highest diversity occurs in South America. 1 Solanum species are a rich source of steroidal alkaloids, flavonoids and their glycosides which are known to possess a variety of biological activities. The glycoalkaloids are natural toxins with ecological and human health importance, such as the allelopathic effect against herbivores, against pathogenic microorganism 2,3 and molluscicidal activity, 4 and are also of interest as starting material for anabolic, anti-fertility, anti-inflammatory, anti-allergic drugs. 5 As the alkaloids, the flavonoids are a frequent group of compounds in Solanum species, and can be used as systematic markers for the family taxons. [6][7][8] Solanum crinitum Lam (Solanaceae), popularly known as "jurubeba" and "fruto-de-lobo", is a shrub or small tree in South America, including southern Brazil and Colombia. 9,10 In the course of our pharmacological and phytochemical investigations of Solanum species, 3,4,8,[11][12][13] we have reported the cytotoxic and antitumoral activities of flavonoids isolated from trichomes of young branches Other Chemical Constituents Is...

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…[26][27][28][29][30] In order to compare the relative stabilities of the epimeric structures 13/14, a molecular modeling study was implemented using the Spartan 06 for Linux program (Wavefunction, Inc.), see Supplementary Information. 31 The complete 1 H and 13 28,31 led to the proposition of the structures (25R) , 16) for the three steroidal glycoalkaloids isolated from this plant (Figure 1). The natural alkaloids 14 and 16 were treated with Ac 2 O/pyridine to yield the peracetyl derivatives 15 and 17.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Other chemical constituents isolated from Solanum crinitum Lam. (Solanaceae)

Cornelius

Carvalho

Alves

et al. 2010

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…1 Pharmacological studies have indicated that solamargine and its derivatives show anti-tumor activities through inhibition of tumor cell growth, such as colon (HT-29, HCT-15), prostate (LNCap, PC-3), breast (T47D, MDA-MB-231), and human hepatoma (PLC/PRF/5) cells. 2 Despite its widespread occurrence and biological importance, there are surprisingly few reports of the total synthesis of solamargine or structurally related compounds.…”

Section: Abstract Solamargine (25r)-3b-{o-a-l-rhamnopyranosylmentioning

confidence: 99%

Total synthesis of solamargine

Wei

Wang

2011

Bioorganic & Medicinal Chemistry Letters

View full text Add to dashboard Cite

“…[1 -5] Found particularly in wild-type members of the genus Solanum, such as varieties of tomato, potato, and eggplant, [2] these compounds are regarded as toxic. [6 -8] However, researchers have also reported and referenced the use of certain glycoalkaloids for use in anti-cancer medications, [9 -14] for their medicinal or bioactive properties, [15,16] for their utility as precursors to the synthesis of useful pharmaceuticals, [5] and for their anti-fungal properties. [17] The interest in extracting these compounds and using them for medicinal purposes is shown, as well, in the form of several patents or patent applications.…”

Section: Introductionmentioning

confidence: 99%

Development of Practical HPLC Methods for the Separation and Determination of Eggplant Steroidal Glycoalkaloids and their Aglycones

Eanes

Tek

Kirsoy

et al. 2008

Journal of Liquid Chromatography & Related Technologies

View full text Add to dashboard Cite

A practical set of HPLC methods was developed for the separation and determination of the eggplant steroidal glycoalkaloids, solanine, chaconine, solasonine, solamargine, and their aglycones, solasodine and solanidine. A gradient method was initially developed, but proved to be neither robust nor practical. Three separate isocratic methods using acetonitrile and ammonium dihydrogen phosphate were developed and shown to be more repeatable, less subject to fluctuations in mobile phase composition, and less time consuming. The effect of adjusting buffer pH, column temperature, and buffer type (triethylammonium phosphate vs. ammonium dihydrogen phosphate) were evaluated. It was also discovered that, by addition of 10% methanol to the acetonitrile portion of the mobile phase, more control over the separations was possible. The use of methanol as a mobile phase entrainer greatly improved separations in some cases and its effectiveness was also dependent upon column temperature. Assessments of the method recovery, limit of detection, and limit of quantitation were made using extracts from S. melongena and S. linnaeanum.

show abstract

Bioactive steroidal alkaloid glycosides from Solanum aculeastrum

Cited by 80 publications

References 15 publications

Other chemical constituents isolated from Solanum crinitum Lam. (Solanaceae)

Other chemical constituents isolated from Solanum crinitum Lam. (Solanaceae)

Total synthesis of solamargine

Development of Practical HPLC Methods for the Separation and Determination of Eggplant Steroidal Glycoalkaloids and their Aglycones

Contact Info

Product

Resources

About