The Experts below are selected from a list of 201 Experts worldwide ranked by ideXlab platform
Helmut Ripperger - One of the best experts on this subject based on the ideXlab platform.
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Steroidal Alkaloid Glycosides from Solanum suaveolens
Phytochemistry, 1997Co-Authors: Helmut Ripperger, Andrea PorzelAbstract:Abstract In addition to khasianine, solamargine, xylosylsolamargine and solasonine, three steroidal Alkaloid Glycosides, solasuaveoline, dihydrosolasuaveoline and isosolasuaveoline, have been isolated from aerial parts of Solanum suaveolens. The structures have been assigned by NMR investigations as (25R)-3β-{O-β- d -glucopyranosyl-(1 → 2)-O-β- d -glucopyranosyl-(1 → 4)-[O-α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-22αN-spirosol-5-ene, (25R)-3β-{O-β- d -glucopyranosyl-(1 → 2)-O-β- d -glucopyranosyl-(1 → 4)-[O-α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-5α,22αN-spirosolane and (25R)-3β-{O-β- d -glucopyranosyl-(1 → 6)-O-β- d -glucopyranosyl-(1 → 3)-[O-α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-22αN-spirosol-5-ene, respectively.
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Steroidal Alkaloid Glycosides from Solanum uporo
Phytochemistry, 1997Co-Authors: Helmut RippergerAbstract:In addition to solamargine, anguivine and isoanguivine, two new steroidal Alkaloid Glycosides, (23S)-23-hydroxyanguivine and (23S)-23-hydroxyisoanguivine, have been isolated from roots of Solanum uporo, the structures of which have been assigned by comparison with literature data as (23S,25R)-3 beta-[O-alpha-L-rhamnopyranosyl-(1-->2)-O- [beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyloxy]-22 alpha N-spirosol-5-en-23-ol and (23S,25R)-3 beta-[O-alpha-L-rhamnopyranosyl-(1-->2)-O-[beta-D- xylopyranosyl-(1-->3)]-beta-D-galactopyranosyloxy]-22 alpha N-spirosol-5-en-23-ol.
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steroid Alkaloid Glycosides from solanum coccineum
Phytochemistry, 1996Co-Authors: Susan Lorey, Andrea Porzel, Helmut RippergerAbstract:Abstract In addition to solamargine, isoanguivine and solasonine, two new steroid Alkaloid Glycosides, xylosyl-solamargine and xylosyl-β-solamarine, have been isolated from the aerial parts of Solanum coccineum, the structures of which have been elucidated as (25R)-3β-{O-β- d - xylopyranosyl -(1 → 2)-O-α- l - rhamnopyranosyl -(1 → 4)-O-[α- l - rhamnopyranosyl -(1 → 2)]-β- d - glucopyranosyloxy }-22αN- spirosol-5-ene and (25S)-3β-O-β- d - xylopyranosyl -(1 → 2)-O-α- l - rhamnopyranosyl -(1 → 4)-O-[α- l - rhamnopyranosyl -(1 → 2)]-β - d - glucopyranosyloxy }-22βN- spirosol-5-ene .
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steroid Alkaloid Glycosides from solanum robustum
Phytochemistry, 1995Co-Authors: Helmut RippergerAbstract:Solamargine, solasonine, N-hydroxyrobustine and a new glycoAlkaloid, N-hydroxysolamargine, has been isolated from the leaves of Solanum robustum, the structure of which has been elucidated as (25R)-3beta-{O-alpha-L-rhamnopyranosyl-(1-->2)-O-[alpha-L- rhamnopyranosyl- (1-->4)]-beta-D-glucopyranosyloxy}-22alphaN- spirosol-5-en-N-ol.
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solanum Alkaloids 128 steroid Alkaloid Glycosides from solanum robustum
European Journal of Organic Chemistry, 1994Co-Authors: Helmut Ripperger, Andrea PorzelAbstract:β1-Solamargine and three new glycoAlkaloids, robustine, N-hydroxyrobustine, and 25-acetoxyrobustine, have been isolated from the roots of Solanum robustum, the structures of which have been elucidated as 3-O-{O-α-L-arabinopyranosyl-(13)-O-[α-L-rhamnopyranosyl-(12)]- O-[α-L-rhamnopyranosyl-(14)]-(β-D-glucopyranosyl}solasodine (3)), its N-hydroxy, and its 25-acetoxy derivative. These compounds have characteristic structures in comparison with the hitherto known Solanum glycoAlkaloids.
Andrea Porzel - One of the best experts on this subject based on the ideXlab platform.
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Steroidal Alkaloid Glycosides from Solanum suaveolens
Phytochemistry, 1997Co-Authors: Helmut Ripperger, Andrea PorzelAbstract:Abstract In addition to khasianine, solamargine, xylosylsolamargine and solasonine, three steroidal Alkaloid Glycosides, solasuaveoline, dihydrosolasuaveoline and isosolasuaveoline, have been isolated from aerial parts of Solanum suaveolens. The structures have been assigned by NMR investigations as (25R)-3β-{O-β- d -glucopyranosyl-(1 → 2)-O-β- d -glucopyranosyl-(1 → 4)-[O-α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-22αN-spirosol-5-ene, (25R)-3β-{O-β- d -glucopyranosyl-(1 → 2)-O-β- d -glucopyranosyl-(1 → 4)-[O-α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-5α,22αN-spirosolane and (25R)-3β-{O-β- d -glucopyranosyl-(1 → 6)-O-β- d -glucopyranosyl-(1 → 3)-[O-α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-22αN-spirosol-5-ene, respectively.
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steroid Alkaloid Glycosides from solanum coccineum
Phytochemistry, 1996Co-Authors: Susan Lorey, Andrea Porzel, Helmut RippergerAbstract:Abstract In addition to solamargine, isoanguivine and solasonine, two new steroid Alkaloid Glycosides, xylosyl-solamargine and xylosyl-β-solamarine, have been isolated from the aerial parts of Solanum coccineum, the structures of which have been elucidated as (25R)-3β-{O-β- d - xylopyranosyl -(1 → 2)-O-α- l - rhamnopyranosyl -(1 → 4)-O-[α- l - rhamnopyranosyl -(1 → 2)]-β- d - glucopyranosyloxy }-22αN- spirosol-5-ene and (25S)-3β-O-β- d - xylopyranosyl -(1 → 2)-O-α- l - rhamnopyranosyl -(1 → 4)-O-[α- l - rhamnopyranosyl -(1 → 2)]-β - d - glucopyranosyloxy }-22βN- spirosol-5-ene .
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solanum Alkaloids 128 steroid Alkaloid Glycosides from solanum robustum
European Journal of Organic Chemistry, 1994Co-Authors: Helmut Ripperger, Andrea PorzelAbstract:β1-Solamargine and three new glycoAlkaloids, robustine, N-hydroxyrobustine, and 25-acetoxyrobustine, have been isolated from the roots of Solanum robustum, the structures of which have been elucidated as 3-O-{O-α-L-arabinopyranosyl-(13)-O-[α-L-rhamnopyranosyl-(12)]- O-[α-L-rhamnopyranosyl-(14)]-(β-D-glucopyranosyl}solasodine (3)), its N-hydroxy, and its 25-acetoxy derivative. These compounds have characteristic structures in comparison with the hitherto known Solanum glycoAlkaloids.
Jian-gong Shi - One of the best experts on this subject based on the ideXlab platform.
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Indole Alkaloid Glycosides with a 1'-(phenyl)ethyl unit from Isatis indigotica leaves.
Acta pharmaceutica Sinica. B, 2019Co-Authors: Qinglan Guo, Cheng-gen Zhu, Ying Guo, Xiaoliang Wang, Jian-gong ShiAbstract:Abstract Seven indole Alkaloid Glycosides containing a 1′-(4″-hydroxy-3″,5″-dimethoxyphenyl)ethyl unit (1–7) were isolated from an aqueous extract of Isatis indigotica leaves (da qing ye). Their structures were determined by spectroscopic data analysis combined with enzymatic hydrolysis as well as comparison of their experimental CD (circular dichroism) and calculated ECD (electrostatic circular dichroism) spectra. Based on analysis of [ α ] D 20 and/or Cotton effect (CE) data of 1–7, two simple roles to assign location and/or configuration of β-glycopyranosyloxy and 1′-(phenyl)ethyl units in the indole Alkaloid Glycosides are proposed. Stereoselectivity in plausible biosynthetic pathways of 1–7 is discussed. Compounds 3 and 4 and their mixture in a 3:2 ratio showed activity against KCNQ2 in CHO cells. The mixture of 5 and 6 (3:2) exhibited antiviral activity against influenza virus H1N1 PR8 with IC50 64.7 μmol/L (ribavirin, IC50 54.3 μmol/L), however, the individual 5 or 6 was inactive. Preliminary structure–activity relationships were observed.
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unprecedented c19 diterpenoid Alkaloid Glycosides from an aqueous extract of fu zi neoline 14 o l arabinosides with four isomeric l anabinosyls
Chinese Chemical Letters, 2017Co-Authors: Xianhua Meng, Qinglan Guo, Cheng-gen Zhu, Jian-gong ShiAbstract:Abstract Four structurally unprecedented aconitane-type C19-diterpenoid Alkaloid Glycosides with isomeric arabinosyls, named aconicarmichosides A–D (1–4), were isolated from an aqueous extract of “fu zi”, the lateral roots of Aconitum carmichaelii. Their structures were determined as neoline 14-O-α- and 14-O-β- l -arabinopyranosides (1 and 2) and 14-O-α- and 14-O-β- l -arabinofuranosides (3 and 4), by spectroscopic and chemical methods including 2D NMR experiments and acid hydrolysis. Compounds 1–4 represent the first examples of glycosidic diterpenoid Alkaloids.
Toshihiro Nohara - One of the best experts on this subject based on the ideXlab platform.
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A New Steroidal Glycoside and a New Phenyl Glycoside from a Ripe Cherry Tomato
Chemical & Pharmaceutical Bulletin, 2008Co-Authors: Yuki Shiono, Tsuyoshi Ikeda, Yukio Fujiwara, Yoshihiro Yanai, Toshihiro NoharaAbstract:A new steroidal glycoside and a new phenyl glycoside have been isolated from a ripe cherry tomato [Lycopersicon esculentum var. cerasiforme (DUNAL) ALEF., Solanaceae] along with two known steroidal Alkaloid Glycosides, esculeoisides A and B, and five aromatic compounds, zizibeoside I, benzyl alcohol β-gentiobioside, rutin, methyl caffeate, and phenylalanine. Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence.
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steroidal Alkaloid Glycosides esculeosides c and d from the ripe fruit of cherry tomato
Chemical & Pharmaceutical Bulletin, 2006Co-Authors: Yuuki Takara, Masamichi Egami, Koichi Uranaka, Tsuyoshi Ikeda, Yukio Fujiwara, Sayaka Matsushita, Hitoshi Yoshimitsu, Toshihiro NoharaAbstract:Two new steroidal Alkaloid Glycosides, esculeosides C and D, have been isolated from the ripe fruit of Cherry tomato [Lycopersicon esculentum var. cerasiforme (DUNAL) ALEF.], along with three known steroidal Alkaloid Glycosides, esculeoside A, esculeoiside B, and lycoperoside G. Their chemical structures were determined on the basis of spectroscopic data.
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Tomato new sapogenols, isoesculeogenin A and esculeogenin B.
Chemical & pharmaceutical bulletin, 2005Co-Authors: Miho Yoshizaki, Tsuyoshi Ikeda, Yukio Fujiwara, Sayaka Matsushita, Masateru Ono, Toshihiro NoharaAbstract:Two novel sapogenols, isoesculeogenin A (1) and esculeogenin B (2) of steroidal Alkaloid Glycosides, lycoperoside F and esculeoside B, respectively, isolated from the ripe tomato have been characterized as (5alpha,22R,23R,25S)-3beta,23,27-trihydroxyspirosolane and (5alpha,22S,23R,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane, respectively.
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Tomato steroidal Alkaloid Glycosides, esculeosides A and B, from ripe fruits
Tetrahedron, 2004Co-Authors: Yukio Fujiwara, Tsuyoshi Ikeda, Hitoshi Yoshimitsu, Ayumi Takaki, Yukie Uehara, Masafumi Okawa, Ken Yamauchi, Masateru Ono, Toshihiro NoharaAbstract:Abstract Major novel steroidal Alkaloid Glycosides, named esculeoside A ( 1 ) and esculeoside B ( 2 ), have been isolated from the pink color-type and the red color-type, respectively, of the ripe tomato fruits of Lycopersicon esculentum MILL. for the first time. The structures of 1 and 2 have been characterized as 3-O-β-lycotetraosyl (5S,22S,23S,25S)-23-acetoxy-3β,27-dihydroxyspirosolane 27-O-β- d -glucopyranoside and 3-O-β-lycotetraosyl (5S,22S,23R,25S)-22,26-epimino-16β,23-epoxy-3β,23,27-trihydroxycholestane 27-O-β- d -glucopyranoside, respectively.
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Lycoperosides A-C, three stereoisomeric 23-acetoxyspirosolan-3β-ol β-lycotetraosides from Lycopersicon esculentum
Phytochemistry, 1996Co-Authors: Shoji Yahara, Noriko Uda, Toshihiro NoharaAbstract:Abstract Three new steroidal Alkaloid Glycosides, lycoperosides A-C, were isolated from leaves and fruits of tomato, Lycopersicon esculentum, and structurally elucidated as the 3-O-β-lycotetraosides of (23R)-23-acetoxy-tomatidine, (23S)-23-acetoxysoladulcidine and (23S,25S)-23-acetoxy-5α,22αN-spirosolan-3β-ol. In addition to these Glycosides, leaves and fruits were found to contain the known major Alkaloid tomatine (tomatidine 3-O-β-lycotetraoside) and leaves a small amount of γ-tomatine (tomatidine 3-O-[β- d -glucopyranosyl -(1 → 4)-β- d -galactopyranoside ] , lycoperoside D).
William Gaffield - One of the best experts on this subject based on the ideXlab platform.
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Spirosolane-containing Solanum species and induction of congenital craniofacial malformations.
Toxicon, 2002Co-Authors: Richard F Keeler, Dale C. Baker, William GaffieldAbstract:Comparison by GC analysis of purified Alkaloid extracts of Solanum species revealed no measurable free solasodine, other spirosolanes, or any non-spirosolane steroidal Alkaloid aglycones in unhydrolyzed total Alkaloid fractions of fruit of Solanum elaeagnifolium Cav. (silverleaf nightshade), Solanum sarrachoides (S. villosum Lam.—hairy nightshade), Solanum dulcamara L. (European bittersweet nightshade) or Solanum melongena L. (eggplant). All Alkaloidal material was apparently present as glycoside. Conversely, sprouts of Solanum tuberosum L. (potato) contained 67% of its Alkaloids as Glycosides, which was freed only upon hydrolysis with the remaining 33% present as free solanidine. GC/MS analysis of hydrolysates of purified extracts of the test Solanum species revealed that solasodine was a principal or sole aglycone of the Alkaloid Glycosides in each of the test species except Solanum tuberosum. In the latter, solanidine was the sole aglycone. Among the test species, exclusive of S. tuberosum, only S. dulcamara contained aglycones other than solasodine. In addition to solasodine, S. dulcamara contained appreciable amounts of an unknown spirosolane, an aglycone provisionally identified as soladulcidine. The induction of congenital craniofacial malformations in hamsters by high oral doses of the four Solanum species that contained mainly solasodine Glycosides—S. elaeagnifolium, S. dulcamara, S. sarrachoides and S. melongena was compared to inductions of malformations by Solanum tuberosum, that contained mainly solanidane Glycosides. Compared to controls, Solanum elaeagnifolium and Solanum dulcamara fruit both induced a high percentage incidence of deformed litters (20.4 and 16.3, respectively) that was statistically significant (P < 0.001 level) while percentage incidence of deformed litters induced by Solanum sarrachoides and Solanum melongena fruit (9.5 and 7.6 respectively) were both higher than controls (3.4%), in neither case was the incidence statistically significant (P < .05). Deformed litter incidence induced by sprouts of Solanum tuberosum was 24.0%, (P < 0.001).
