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Structure Database (LMSD)

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Common Name

Quassin

Systematic Name

2,12-Dimethoxypicrasa-2,12-diene-1,11,16-trione

Synonyms

LM ID

LMPR0106110002

Formula

C₂₂H₂₈O₆

Exact Mass

Calculate m/z

388.188591

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Quassin is a quassinoid that has been found in Q. amara and has diverse biological activities.^1,2,3 It is active against chloroquine-sensitive and -resistant strains of P. falciparum (IC50 = 0.15 µM for both).¹ Quassin has antifeedant and insecticidal activity against the diamondback moth (P. xylostella) when applied to dietary cabbage leaf discs at 16, 31.9, or 63.7 µg/cm2.2 It increases viability of SH-SY5Y cells in a model of hydrogen peroxide-induced neuronal injury when used at concentrations of 25, 50, or 100 µM.³

This information has been provided by Cayman Chemical

References

1. Mishra, K., Chakraborty, D., Pal, A., et al. Plasmodium falciparum: in vitro interaction of quassin and neo-quassin with artesunate, a hemisuccinate derivative of artemisinin. Exp. Parasitol. 124(4), 421-427 (2010).

2. Daido, M., Fukamiya, N., Okano, M., et al. Antifeedant and insecticidal activity of quassinoids against diamondback moth (Plutella xylostella). Biosci. Biotechnol. Biochem. 57(2), 2440246 (1993).

3. He, C., Wang, Y., Yang, T., et al. Quassinoids with insecticidal activity against Diaphorina citri Kuwayama and neuroprotective activities from Picrasma quassioides. J. Agric. Food. Chem. 68(1), 117-127 (2020).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Quassia amara (#43725)

Magnoliopsida (#3398)

Quassin and Neoquassin,
Tetrahedron, 1961

DOI: 10.1016/0040-4020(61)80013-6

String Representations

InChiKey (Click to copy)

IOSXSVZRTUWBHC-LBTVDEKVSA-N

InChi (Click to copy)

InChI=1S/C22H28O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15,19H,8-9H2,1-6H3/t10-,12+,13+,15-,19+,21-,22+/m1/s1

SMILES (Click to copy)

[C@@]12(C)[C@@]3([H])CC(=O)O[C@]1([H])C[C@@]1([H])[C@H](C)C=C(OC)C(=O)[C@]1(C)[C@@]2([H])C(=O)C(=C3C)OC