LIPID MAPS

Structure Database (LMSD)

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Common Name

Yemuoside YM10

Systematic Name

(3β)-3-[[2-O-(6-deoxy-α-L-mannopyranosyl)-α-L-arabinopyranosyl]oxy]-30-noroleana-12,20(29)-dien-28-oic acid, O-6-deoxy-α-L-mannopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl ester

Synonyms

Ciwujianoside B

LM ID

LMPR0106150076

Formula

C₅₈H₉₂O₂₅

Exact Mass

Calculate m/z

1188.592777

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Ciwujianoside B is a triterpenoid saponin that has been found in A. senticosus and has diverse biological activities.^1,2,3 It inhibits α-glucosidase and scavenges peroxynitrite radicals in cell-free assays (IC50s = 0.74 and 34.8 µM, respectively).¹ Ciwujianoside B (40 mg/kg) increases survival and reverses radiation-induced decreases in the number of peripheral blood leukocytes in irradiated mice.² It improves memory in the novel object recognition test in mice when administered at a dose of 0.5 mg/kg.³

This information has been provided by Cayman Chemical

References

1. Kwon, R.H., Na, H., Kim, J.H., et al. Comprehensive profiling of phenolic compounds and triterpenoid saponins from Acanthopanax senticosus and their antioxidant, α-glucosidase inhibitory activities. Sci. Rep. 14(1), 26330 (2024).

2. Li, Y.-R., Cao, W., Guo, J., et al. Comparative investigations on the protective effects of rhodioside, ciwujianoside-B and astragaloside IV on radiation injuries of the hematopoietic system in mice. Phytother. Res. 25(5), 644-653 (2011).

3. Yamauchi, Y., Ge, Y.-W., Yoshimatsu, K., et al. Memory enhancement by oral administration of extract of Eleutherococcus senticosus leaves and active compounds transferred in the brain. Nutrients 11(5), 1142 (2019).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Stauntonia chinensis (#161269)

Magnoliopsida (#3398)

[The structures of yemuoside YM10 and YM12 from Stauntonia chinensis].,
Yao Xue Xue Bao, 1989

Pubmed ID: 2609984

String Representations

InChiKey (Click to copy)

UPROOJBJZLZCGS-CHTHVDMYSA-N

InChi (Click to copy)

InChI=1S/C58H92O25/c1-23-11-16-58(53(73)83-51-44(71)40(67)37(64)30(79-51)22-75-48-45(72)41(68)46(29(20-59)78-48)81-49-42(69)38(65)34(61)24(2)76-49)18-17-56(7)26(27(58)19-23)9-10-32-55(6)14-13-33(54(4,5)31(55)12-15-57(32,56)8)80-52-47(36(63)28(60)21-74-52)82-50-43(70)39(66)35(62)25(3)77-50/h9,24-25,27-52,59-72H,1,10-22H2,2-8H3/t24-,25-,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-,55-,56+,57+,58-/m0/s1

SMILES (Click to copy)

[H][C@@]12CC(=C)CC[C@@]1(CC[C@]1([C@]3([C@@]([C@]4(CC[C@@H](C([C@@]4(CC3)[H])(C)C)O[C@@H]3OC[C@@H]([C@@H]([C@H]3O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O)O)O)O)O)C)(CC=C21)[H])C)C)C(=O)O[C@@H]1O[C@H](CO[C@H]2[C@H](O)[C@@H](O)[C@H](O[C@@H]3O[C@H]([C@@H]([C@H]([C@H]3O)O)O)C)[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@H]1O