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1. (Article ID: 11466)
Kinghorn AD, Kaneda N, Baek NI, Kennelly EJ, Soejarto DD
Noncariogenic intense natural sweeteners
Medicinal Research Reviews 18(5) (1998)
347-360
There is a definite relationship between the dietary consumption of sucrose and the incidence of dental caries. Noncaloric sucrose substitutes for use in the sweetening of foods, beverages, and medicines may be either synthetic compounds or natural products. In the United States, four potently sweet artificial sweeteners are approved, namely, saccharin, aspartame, acesulfame potassium, and sucralose. Highly sweet plant constituents are used in Japan and some other countries, including the diterpene glycoside stevioside and-the protein thaumatin. Recent progress in a research project oriented towards the discovery and evaluation of novel potentially noncariogenic sweeteners from plants has focused on substances in the sesquiterpenoid, diterpenoid, triterpenoid, steroidal saponin, and proanthocyanidin structural classes. The feasibility of using Mongolian gerbil electrophysiological and behavioral assays to monitor the sweetness of plant extracts, chromatographic fractions, and pure isolates has been investigated. An in vivo cariogenicity study on the commercially available natural sweeteners stevioside and rebaudioside A has been carried out.
plant constituents, sucrose substitutes, isoprenoids, phenols, biological evaluation
The publication contains the following compound(s):
- Compound ID: 29268
|
/Variants 0/-b-D-Glcp-(1-3)-Subst
/Variants 0/ is:
?%b-D-GlcpA-(1-2)-
OR (exclusively)
?%b-D-Glcp-(1-2)-
Subst = abrusogenin = SMILES C/C6=C/C[C@@H]([C@@H](C)C4CC[C@@]5(C)C2CCC1[C@](C)({28}C(=O)O){3}[C@@H](O)CC[C@@]13C[C@@]23CC[C@]45C)OC6=O |
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Structure type: oligomer
Trivial name: abrusoside A, abrusoside C, abrusoside E
Compound class: triterpenoid glycoside
- Compound ID: 29269
|
b-D-Glcp-(1-2)-b-D-GlcpA6(%)Me-(1-3)-Subst
Subst = abrusogenin = SMILES C/C6=C/C[C@@H]([C@@H](C)C4CC[C@@]5(C)C2CCC1[C@](C)({28}C(=O)O){3}[C@@H](O)CC[C@@]13C[C@@]23CC[C@]45C)OC6=O |
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Structure type: oligomer
Trivial name: abrusoside B, abrusoside D
Compound class: triterpenoid glycoside
- Compound ID: 29270
|
b-D-GlcpA6Me-(1-2)-b-D-Glcp-(1-3)-Subst28(%)Me
Subst = abrusogenin = SMILES C/C6=C/C[C@@H]([C@@H](C)C4CC[C@@]5(C)C2CCC1[C@](C)({28}C(=O)O){3}[C@@H](O)CC[C@@]13C[C@@]23CC[C@]45C)OC6=O |
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Structure type: oligomer
Trivial name: abrusoside E 6''-methyl ester, abrusoside E dimethyl ester
Compound class: triterpenoid glycoside
- Compound ID: 26879
|
a-L-Rhap-(1-26)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = osladin aglycon = SMILES C[C@H]({26}[C@H](O)O1)CC[C@@H]1[C@@H](C)[C@H]2CC[C@@]3([H])[C@]4([H])CC([C@@]5([H])C{3}[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]23C)=O |
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Structure type: oligomer
Trivial name: osladin
Compound class: saponin glycoside, triterpenoid glycoside
Reference(s) to other database(s): CCSD:
43358, CBank-STR:21992
- Compound ID: 29265
|
a-L-Rhap-(1-3)-+
|
a-L-Rhap-(1-2)-a-D-Glcp-(1-1)-+
|
a-L-Rhap-(1-3)-+ |
| |
a-L-Rhap-(1-2)-a-D-Glcp-(1-12)-Subst
Subst = 12-hydroxy-all-trans-farnesol = SMILES C/C(CC/C=C(CC/C=C({12}CO)\C)\C)=C\{1}CO |
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Structure type: oligomer
Trivial name: mukurozioside IIb
Compound class: glycoside
- Compound ID: 29266
|
/Variants 0/-a-L-Arap
/Variants 0/ is:
Subst3-(6-1)-
OR (exclusively)
Subst2-(6-1)-
OR (exclusively)
Subst1-(6-1)-
Subst1 = gaudichaudioside A aglycone = SMILES C/C(=C\{15}CO)CC/C1=C(C=O)/C{6}[C@H](O)C2[C@@](C)({16}CO)CCC[C@]12C;
Subst2 = gaudichaudioside B aglycone = SMILES C/C(=C\{15}CO)CC/C1=C(CO)/C{6}[C@H](O)C2[C@@](C)({16}CO)CCC[C@]12C;
Subst3 = gaudichaudioside C aglycone = SMILES C/C(=C\{15}CO)CC/C1=C(CO)/C{6}[C@H](O)C2[C@@](C)({16}CO)C[C@H](O)C[C@]12C |
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Structure type: monomer
Trivial name: gaudichaudioside A, gaudichaudioside B, gaudichaudioside C
Compound class: glycoside
- Compound ID: 29267
|
/Variants 0/-a-L-Arap
/Variants 0/ is:
Subst2-(6-1)-
OR (exclusively)
Subst1-(6-1)-
Subst1 = gaudichaudioside D aglycone = SMILES C/C(=C\{15}CO)CCC1{8}[C@](C)(O)C{6}[C@H](O)C2[C@@](C)({16}CO)CCC[C@]12C;
Subst2 = gaudichaudioside E aglycone = SMILES C/C(=C\{15}CO)CCC1{8}[C@](C)(O)C{6}[C@H](O)C2[C@@](C)(C)C{3}[C@H](O)C[C@]12C |
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Structure type: monomer
Trivial name: gaudichaudioside D, gaudichaudioside E
Compound class: glycoside
- Compound ID: 29271
|
/Variants 0/-b-D-GlcpA-(1-3)-Subst
/Variants 0/ is:
b-D-Xylp-(1-2)-
OR (exclusively)
b-D-GlcpA-(1-2)-
Subst = 25-al-olean-18-en-30-oic acid = SMILES C[C@]1(C){3}[C@@H](O)CC[C@@]2(C=O)C1CC[C@]5(C)C2CCC4/C3=C/[C@@](C){30}(C(=O)O)CC[C@]3(C)CC[C@]45C |
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Structure type: oligomer
Trivial name: periandrin I, periandrin V
Compound class: triterpenoid glycoside
- Compound ID: 29272
|
/Variants 0/-Subst
/Variants 0/ is:
b-D-Qui-(1-12)-
OR (exclusively)
a-L-Arap-(1-12)-
Subst = 20,25-dihydroxy-3,4-seco-5α-dammar-4(28),23-dien-3-oic acid = SMILES C=C(C)[C@@H]3CC[C@]2(C)C(C{12}[C@@H](O)C1C{20}([C@@](C)(O)C/C=C/C{25}(C)(C)O)CC[C@]12C)[C@@]3(C)CC{3}C(=O)O |
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Structure type: monomer
Trivial name: pterocaryoside A, pterocaryoside B
Compound class: triterpenoid glycoside
- Compound ID: 29273
|
a-L-Rhap-(1-26)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = 5α,22R,25S-6-oxo-22,26-epoxycholestan-7-en-3β,26R-diol = SMILES C[C@H]5CC[C@H]([C@@H](C)[C@H]4CC[C@H]3/C2=C/C(=O)[C@H]1C{3}[C@@H](O)CC[C@]1(C)[C@H]2CCC34C)O{26}[C@H]5O |
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Structure type: oligomer
Trivial name: polypodoside A
Compound class: triterpenoid glycoside
- Compound ID: 29274
|
b-D-Glcp-(1-3)-+
|
a-L-Rhap3(%)Me-(1-26)-Subst
Subst = 5α,22R,25S-6-oxo-22,26-epoxycholestan-7-en-3β,26R-diol = SMILES C[C@H]5CC[C@H]([C@@H](C)[C@H]4CC[C@H]3/C2=C/C(=O)[C@H]1C{3}[C@@H](O)CC[C@]1(C)[C@H]2CCC34C)O{26}[C@H]5O |
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Structure type: oligomer
Trivial name: polypodoside B, polypodoside C
Compound class: triterpenoid glycoside
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