| 词条 | Esculeoside A |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 432918792 | ImageFile = Esculeoside A.svg | ImageSize = 250px | ImageAlt = | IUPACName = (2aS,2'S,3'S,4S,5'S,6aS,6bS,8aS,8bR,9S,11aS,12bR)-4-(((2R,3R,4R,5R,6R)-3,4-dihydroxy-5-(((2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6a,8a,9-trimethyl-5'-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)octadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-piperidin]-3'-yl acetate | OtherNames = | Section1 = {{Chembox Identifiers | CASNo = 532387-86-3 | CASNo_Ref = {{cascite|correct|??}} | PubChem = 10887728 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 9062993 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 65866 | SMILES = C[C@@]12[C@](CC[C@]3([H])[C@]2([H])CC[C@@]4(C)C3C[C@@]5([H])[C@]4([H])[C@H](C)[C@]6(NC[C@@H](CO[C@H]7[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O7)C[C@@H]6OC(C)=O)O5)([H])C[C@@H](O[C@]8([H])O[C@H](CO)[C@H](O[C@@]9([H])[C@H](O[C@@]%10([H])[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O%10)[C@@H](O[C@@]%11([H])[C@H](O)[C@@H](O)[C@H](O)CO%11)[C@H](O)[C@@H](CO)O9)[C@H](O)[C@H]8O)CC1 | InChI = 1/C58H95NO29/c1-21-36-30(88-58(21)35(79-22(2)64)11-23(14-59-58)19-77-51-45(74)41(70)38(67)31(15-60)81-51)13-28-26-6-5-24-12-25(7-9-56(24,3)27(26)8-10-57(28,36)4)80-53-47(76)43(72)48(34(18-63)84-53)85-55-50(87-54-46(75)42(71)39(68)32(16-61)82-54)49(40(69)33(17-62)83-55)86-52-44(73)37(66)29(65)20-78-52/h21,23-55,59-63,65-76H,5-20H2,1-4H3/t21-,23-,24-,25-,26+,27-,28-,29+,30-,31+,32+,33+,34+,35-,36-,37-,38+,39+,40+,41-,42-,43+,44+,45+,46+,47+,48-,49-,50+,51+,52-,53+,54-,55-,56-,57-,58-/m0/s1 | InChIKey = VSQBWNYALURFOT-ZSFCQSFNBT | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C58H95NO29/c1-21-36-30(88-58(21)35(79-22(2)64)11-23(14-59-58)19-77-51-45(74)41(70)38(67)31(15-60)81-51)13-28-26-6-5-24-12-25(7-9-56(24,3)27(26)8-10-57(28,36)4)80-53-47(76)43(72)48(34(18-63)84-53)85-55-50(87-54-46(75)42(71)39(68)32(16-61)82-54)49(40(69)33(17-62)83-55)86-52-44(73)37(66)29(65)20-78-52/h21,23-55,59-63,65-76H,5-20H2,1-4H3/t21-,23-,24-,25-,26+,27-,28-,29+,30-,31+,32+,33+,34+,35-,36-,37-,38+,39+,40+,41-,42-,43+,44+,45+,46+,47+,48-,49-,50+,51+,52-,53+,54-,55-,56-,57-,58-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = VSQBWNYALURFOT-ZSFCQSFNSA-N}} | Section2 = {{Chembox Properties | C=58|H=95|N=1|O=29 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} Esculeoside A is a spirosolane-type glycoside with the molecular formula C58H95NO29.[1] The structure of this product is 3-Ο-β-lycotetraosyl (22S,23S,25S)-23-acetoxy-3β,27-dihydroxy-5α-spirosolane 27-Ο-β-D-glucopyranoside.[1] Fujiwara and colleagues were the first to isolate esculeoside A from the ripe fruit of the Cherry tomato in 2002. Esculeoside A, along with many other steroidal alkaloid glycosides, have been shown to possess cytotoxic activity that could result in a variety of potential health benefits for humans. SynthesisThis natural product can be obtained using column chromatographies of high-porous polystyrene gels and reversed silica gels from a methanolic extract of many varieties of tomatoes.[1] It will appear as colorless needles when synthesized using this method. Evidence suggests that α-tomatine is a precursor of esculeoside A.[2] In order for alpha tomatine to be converted to esculeoside A, isomerization of the F-ring is required. The mechanism for this reaction is unclear at this time but research from Iijima and colleagues in 2009 suggest a glycosylation step in the putative pathway from α-tomatine to esculeoside A depends on the plant hormone ethylene.[2][6] OccurrencePotatoes, eggplant, and tomatoes are all solanaceous plants that contain unique glycoalkaloids.[6] In the case of tomatoes, one of those unique glycoalkaloids is esculeoside A. A tomato saponin, esculeoside A, is found in quantities four times that of lycopene in ripe tomatoes.[3] Potential health benefitsStudies have shown esculeoside A may be metabolized into derivatives that perform various beneficial activities in the human body including anti-osteoporosis, anti-menopausal disorder and anti-tumor activities.[3] Recent studies in mice have shown a potential link between esculeoside A and cholesterol levels. In one study, esculeoside A administered to mice reduced serum levels of LDL cholesterol and triglycerides by 25-45% without impacting the rates of HDL cholesterol.[4] The potential health benefits of esculeoside A appear to change with factors such as the age of the tomato fruit, the heat used in processing tomatoes, and the pH used in processing.[5] The highest amounts of esculeoside A were found in the outer skin and wall (pericarp wall) of the tomato fruit. Mature tomatoes tended to show higher amounts of esculeoside A than extracts taken from immature tomatoes. Extracts of esculeoside A in the Katsumata study were shown to be stable when heated until the point of 225 °C. This same study found esculeoside A extracts in water at pH 7-11 were stable throughout the heat sterilization process but unstable under acidic conditions.[5] Research has also shown esculeoside A amounts increase when tomatoes are treated with the phytohormone, ethylene.[6] Collectively, research suggests daily intake of esculeoside A from tomatoes could have many benefits. References1. ^{{cite journal|last=Fujiwara|first=Y.|author2=Takaki, A. |author3=Uehara, Y. |author4=Ikeda, T. |author5=Okawa, M. |author6=Yamauchi, K. |author7=Ono, M. |author8=Yoshimitsu, H. |author9=Nohara, T. |title=Tomato steroidal alkaloid glycosides, esculeosides A and B, from ripe fruits|journal=Tetrahedron|year=2004|volume=60|pages=4915–4920|doi=10.1016/j.tet.2004.03.088}} 2. ^1 {{cite journal|last=Yamanaka|first=T.|author2=Vincken, J. |author3=Zuilhof, H. |author4=Legger, A. |author5=Takada, N. |author6=Gruppen, H. |title=C22 Isomerization in a-Tomatine-to-Esculeoside A Conversion during Tomato Ripening Is Driven by C27 Hydroxylation of Triterpenoidal Skeleton|journal=Journal of Agricultural and Food Chemistry|year=2009|volume=57|pages=3786–3791|doi=10.1021/jf900017n |pmid=19415927}} 3. ^1 {{cite journal|last=Manabe|first=H.|author2=Murakami, Y. |author3=El-Aasr, M. |author4=Ikeda, T. |author5=Fujiwara, Y. |author6=Ono, M. |author7=Nohara, T. |title=Content variations of the tomato saponin Esculeoside A in various processed tomatoes|journal=Journal of Natural Medicine|year=2010|doi=10.1007/s11418-010-0443-4 |volume=65 |pages=176–179}} 4. ^1 2 {{cite journal|last=Nohara|first=Toshihiro|author2=Ono, M. |author3=Ikeda, T. |author4=Fujiwara, Y. |author5=El-Aasr, M. |title=The Tomato Saponin, Esculeoside A|journal=Journal of Natural Products|year=2010|volume=73|pages=1734–1741|doi=10.1021/np100311t}} 5. ^1 {{cite journal|last=Katsumata|first=A.|author2=Kimura, M. |author3=Saigo, H. |author4=Aburaya, K. |author5=Nakano, M. |author6=Ikeda, T. |author7=Fujiwara, Y. |author8=Nagai, R. |title=Changes in Esculeoside A Content in Different Regions of the Tomato Fruit during Maturation and Heat Processing|journal=Journal of Agricultural and Food Chemistry|year=2011|volume=59|pages=4104–4110|doi=10.1021/jf104025p |pmid=21395308}} 6. ^1 2 {{cite journal|last=Iijima|first=Y.|author2=Fujiwara, Y. |author3=Tokita, T. |author4=Ikeda, T. |author5=Nohara, T. |author6=Aoki, K. |author7=Shibata, D. |title=Involvement of Ethylene in the Accumulation of Esculeoside A during Fruit Ripening of Tomato (Solanum lycopersicum)|journal=Journal of Agricultural and Food Chemistry|year=2009|volume=57|pages=3247–3252|doi=10.1021./jf8037902}} 3 : Steroidal glycosides|Alkaloid glycosides|Saponins |
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