- Revision of the Structure of N, O-Diacetylsolasodine. Unusual Epimerization at the Spiro Carbon Atom during Acetylation of Solasodine
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The steroidal alkaloid solasodine (1) undergoes inversion of configuration at the C-22 spiro atom when treated with acetic anhydride-pyridine at ambient temperature. The basic solvolysis of the N,O-diacetyl derivative (2) reverses the reaction, yielding the starting solasodine (1). The mechanisms of both processes (acetylation and deacetylation) were studied in terms of possible reaction pathways.
- Czajkowska-Szczykowska, Dorota,Jastrzebska, Izabella,Rode, Joanna E.,Morzycki, Jacek W.
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- Direct amination of EF spiroketal in steroidal sapogenins: An efficient synthetic strategy and method for related alkaloids
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Herein a direct amination of the EF spiroketal in steroidal sapogenins is reported for the first time. This reaction provides a new strategy and method for the synthesis of steroidal alkaloids, which are generally isolated from Chinese medicinal herbs and pharmaceutically attractive. Solasodine, a steroidal alkaloid with good antitumor bioactivities, is synthesized in three steps and 43% overall yield.
- Wu, Jing-Jing,Gao, Ran,Shi, Yong,Tian, Wei-Sheng
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- ANTIFUNGAL STRESS METABOLITES FROM SOLANUM AVICULARE
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The steroidal alkaloids 5β-solasodan-3-one and solasodenone were isolated as antifungal stress metabolites from leaves of Solanum aviculare stressed by vacuum infiltration with water.The constitutive leaf alkaloids, solasodine and solamargine, also showed antifungal activity.Key Word Index-Solanum aviculare; Solanaceae; solasodine; Solanum alkaloids; stress metabolites; vacuum infiltration.
- Rowan, Daryl D.,Macdonald, Pauline E.,Skipp, Robert A.
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- spiral steroid alkali alkane xylosides alkloids method for the synthesis of (by machine translation)
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The invention discloses a convergent spiral steroid alkali alkane xylosides alkaloid chemical synthesis method, the method comprises the following steps: (a) the 3?Hydroxy acyl silicon-based or for the protection of sapogenin spiral steroid (II) into the corresponding 16?Acetoxy?22?Carbonyl?26?(III) hydroxyl gallbladder gonanes; (b) 3?Hydroxy silicon-based or acyl group protection for 16?Acetoxy?22?Carbonyl?26?Preparation of sulfonic acid ester gallbladder gonanes (IV); (c) 3?Hydroxy silicon-based or acyl group protection for 16?Acetoxy?22?Carbonyl?26?Preparation of azide interior gonanes (V); (d) (VI) spiral steroid alkali alkane sapogenin the preparation; (e) acyl protecting spiral steroid alkali alkane xylosides alkloids preparation (VII); (f) spiral steroid alkali alkane xylosides alkloids (I) of the preparation. The preparation method of this invention simple process, high yield, has strong utility value. (by machine translation)
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- Facile synthesis of solasodine based on a mild halogenation-ring opening reaction of spiroketals in steroidal sapogenins
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Herein we report a halogenation-ring opening reaction of spiroketals in steroidal sapogenins at room temperature to gain highly valuable ω-halo enol ethers in excellent yields. Boosted by this method, we have prepared solasodine, an antitumor steroidal alkaloid, from diosgenin acetate in three steps with an overall yield of 50%.
- Wu, Jing-Jing,Shi, Yong,Tian, Wei-Sheng
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supporting information
p. 1215 - 1217
(2015/03/04)
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- Antifungal activity and fungal metabolism of steroidal glycosides of Easter lily (Lilium longiflorum Thunb.) by the plant pathogenic fungus, Botrytis cinerea
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Botrytis cinerea Pers. Fr. is a plant pathogenic fungus and the causal organism of blossom blight of Easter lily (Lilium longiflorum Thunb.). Easter lily is a rich source of steroidal glycosides, compounds which may play a role in the plant-pathogen interaction of Easter lily. Five steroidal glycosides, including two steroidal glycoalkaloids and three furostanol saponins, were isolated from L. longiflorum and evaluated for fungal growth inhibition activity against B. cinerea, using an in vitro plate assay. All of the compounds showed fungal growth inhibition activity; however, the natural acetylation of C-6′′′ of the terminal glucose in the steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-l-rhamnopyranosyl-(1→2)-[6-O- acetyl-β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (2), increased antifungal activity by inhibiting the rate of metabolism of the compound by B. cinerea. Acetylation of the glycoalkaloid may be a plant defense response to the evolution of detoxifying mechanisms by the pathogen. The biotransformation of the steroidal glycoalkaloids by B. cinerea led to the isolation and characterization of several fungal metabolites. The fungal metabolites that were generated in the model system were also identified in Easter lily tissues infected with the fungus by LC-MS. In addition, a steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-l-rhamnopyranosyl- (1→2)-β-d-glucopyranoside (6), was identified as both a fungal metabolite of the steroidal glycoalkaloids and as a natural product in L. longiflorum for the first time.
- Munafo, John P.,Gianfagna, Thomas J.
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p. 5945 - 5954
(2012/02/03)
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- A facile and efficient method for the synthesis of solasodine from diosgenin
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A facile and high-yielding route for the synthesis of solasodine from diosgenin is devised. Ring opening of steroidal spiroketal under mild conditions with trifluoroacetyl trifluoromethanesulfonate (TFAT) provides an applicable protocol to prepare key intermediates 4 or 3-Ac-solasodine, which can potentially serve as a platform for the selective functionalization of C(3)-OH and N-H of solasodine. The simple operations without purification by column chromatography make this method suitable to scale up.
- Zhang, Gui-Ping,Shen, Si-Da,Lei, Min,Hu, Li-Hong
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p. 5894 - 5896
(2011/09/19)
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- Total synthesis of solamargine
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Solamargine, (25R)-3β-{O-α-l-rhamnopyranosyl-(1→2)-[O- α-l-rhamnopyranosyl-(1→4)]-β-d-glucopyranosyloxy} -22α-N-spirosol-5-ene, has been synthesized in 13 steps in a 10.5% overall yield starting from the naturally abundant diosgenin. Condensation of a partially protected glucopyranosyl donor with an oxaza-spiro moiety, which was formed in one-pot azido reduction, significantly improved the synthesis of desired molecule. The target compound exhibited good cytotoxic activities against tumor cells HeLa, A549, MCF-7, K562, HCT116, U87, and HepG2 with IC 50 ranging from 2.1 to 8.0 μM.
- Wei, Guohua,Wang, Jing,Du, Yuguo
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p. 2930 - 2933
(2011/06/26)
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- Synthesis and evaluation of in vitro anticancer activity of novel solasodine derivatives
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Solasodine 11 is a steroidal alkaloid with various biological activities. Herein, 8 novel solasodine derivatives were synthesized and their effect on prostate cancer cell proliferation was assessed in vitro. Significant improvement in antiproliferative activity was achieved among some of the synthetic analogs. In particular, 19 exhibited the most potent inhibitory effect against the proliferation of PC-3 cell line (IC50=3.91μmol/L).
- Zha, Xiao Ming,Zhang, Fei Ran,Shan, Jia Qi,Zhang, Yi Hua,Liu, Jun O.,Sun, Hong Bin
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p. 1087 - 1090
(2011/10/05)
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- Further syntheses of cyproterone acetate
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The present invention relates to improved methods for synthesising cyproterone acetate (17α-Acetoxy-6-chloro-1α, 2α-methylene-4,6-pregnadiene-3,20-dione) from solasodine. The methods of the invention are shorter as those of the prior art and therefore more economic.
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Page/Page column 9
(2010/02/07)
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- Partial Synthesis of the Steroid Alkaloids Teinemine, 22-Isoteinemine, Etioline, and 25-Isoetioline
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The rare 16α-hydroxylated steroid alkaloids teinemine , 22-isoteinemine , etioline , and 25-isoetioline are synthesized from the abundant spirosolane alkaloids tomatid-5-en-3β-ol and solasodine , respectively.The crucial stages of these syntheses are the conversion of 1 or 15 into the N-protected (22S,25S)-, (22R,25S)-, and (22S,25R) -22,26-epimino-3β-hydroxycholest-5-en-16-ones 6, 7, and 18 as well as their reductions with sodium/2-propanol to the 16α-hydroxy compounds teinemine (8), 22-isoteinemine (10), and (22S,25R)-22,26-epiminocholest-5-ene-3β,16α-diol (19), respectively.By treatment with sodium methanolate the N-chloro derivatives 9 and 11 of 8 and 10 afford etioline (12).In an analogous manner, the N-chloro derivative 20 of 19 is converted into 25-isoetioline (21).
- Quyen, Le thi,Ripperger, Helmut,Schreiber, Klaus
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p. 143 - 149
(2007/10/02)
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- ACTIVE MANGANASE DIOXIDE: A REAGENT FOR A BIOMIMETIC CYCLIZATION OF 16β-HYDROXYLATED 22.26-EPIMINOCHOLESTANES TO SPIROSOLANE ALKALOIDS
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Treatment of the 16β-hydroxylated 22.26-epiminocholestanes 1 - 4 with activated MnO2 leads in a biogenetically remarkable cyclization directly and in good yields to the corresponding spirosolane alkaloids 5 - 8.
- Adam, G.,Huong, H. Th.
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p. 1931 - 1932
(2007/10/02)
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