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Structure Database (LMSD)

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Common Name

Quillaic acid

Systematic Name

3β,16α-dihydroxy-23-oxoolean-12-en-28-oic acid

Synonyms

LM ID

LMPR0106150037

Formula

C₃₀H₄₆O₅

Exact Mass

Calculate m/z

486.334525

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Quillaic acid is a triterpene saponin that has been found in Q. saponaria bark and has diverse biological activities.^1,2,3 It is cytotoxic to SNU-1 and KATO III gastric cancer cells (IC50s = 13.6 and 67 µM, respectively).¹ Quillaic acid induces hot plate analgesia in mice (ED50 = 20.7 mg/kg).² It reduces ear edema induced by arachidonic acid or phorbol 12-myristate 13-acetate (TPA) in mice when administered topically at doses of 0.7 and 1.6 mg/ear, respectively.³

This information has been provided by Cayman Chemical

References

1. Guzmán, L., Villalón, K., Marchant, M.J., et al. In vitro evaluation and molecular docking of QS-21 and quillaic acid from Quillaja saponaria Molina as gastric cancer agents. Sci. Rep. 10(1), 10534 (2020).

2. Arrau, S., Delporte, C., Cartagena, C., et al. Antinociceptive activity of Quillaja saponaria Mol. saponin extract, quillaic acid and derivatives in mice. J. Ethnaopharmacol. 133(1), 164-167 (2011).

3. Rodríguez-Díaz, M., Delporte, C., Cartagena, C., et al. Topical anti-inflammatory activity of quillaic acid from Quillaja saponaria Mol. and some derivatives. J. Pharm. Pharmacol. 63(5), 718-724 (2011).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Quillaja saponaria (#32244)

Magnoliopsida (#3398)

Chemical synthesis of quillaic acid, the aglycone of QS-21,
Org. Chem. Front., 2021

DOI: 10.1039/D0QO01356K

String Representations

InChiKey (Click to copy)

MQUFAARYGOUYEV-UAWZMHPWSA-N

InChi (Click to copy)

InChI=1S/C30H46O5/c1-25(2)13-14-30(24(34)35)19(15-25)18-7-8-21-26(3)11-10-22(32)27(4,17-31)20(26)9-12-28(21,5)29(18,6)16-23(30)33/h7,17,19-23,32-33H,8-16H2,1-6H3,(H,34,35)/t19-,20+,21+,22-,23+,26-,27-,28+,29+,30+/m0/s1

SMILES (Click to copy)

[C@]12([C@H](O)C[C@@]3(C)[C@]4(C)CC[C@@]5([H])[C@](C)(C=O)[C@@H](O)CC[C@]5(C)[C@@]4([H])CC=C3[C@]1([H])CC(C)(C)CC2)C(=O)O