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Structure Database (LMSD)

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Common Name

Ganodermanontriol

Systematic Name

3-oxo-lanosta-7,9(11)-dien-24S,25R,26-triol

Synonyms

LM ID

LMPR0106050005

Formula

C₃₀H₄₈O₄

Exact Mass

Calculate m/z

472.355261

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Ganodermanontriol is a triterpene that has been found in G. lucidum and has diverse biological activities.^1,2,3,4 It inhibits the activity of HIV-1 protease (IC50 = 70 µM), as well as reduces the activity of 5α-reductase by 32% when used at a concentration of 667 µM.^1,2 Ganodermanontriol (25 and 50 µM) inhibits proliferation, colony formation, invasion, and migration of MDA-MB-231 human breast cancer cells.³ It reduces hepatocyte necrosis and increases in hepatic TNF-α and IL-6 levels in a mouse model of LPS/D-galactosamine-induced acute liver injury when administered at a dose of 5 mg/kg.⁴

This information has been provided by Cayman Chemical

References

1. Hu, Z., Du, R., Xiu, L., et al. Protective effect of triterpenes of Ganoderma lucidum on lipopolysaccharide-induced inflammatory responses and acute liver injury. Cytokine 127, 154917 (2020).

2. Jiang, J., Jedinak, A., and Silva, D. Ganodermanontriol (GDNT) exerts its effect on growth and invasiveness of breast cancer cells through the down-regulation of CDC20 and uPA. Biochem. Biophys. Res. Commun. 415(2), 325-329 (2011).

3. Liu, J., Kurashiki, K., Shimizu, K., et al. Structure–activity relationship for inhibition of 5α-reductase by triterpenoids isolated from Ganoderma lucidum. Bioorg. Med. Chem. 14(24), 8654-8660 (2006).

4. Min, B.-S., Nakamura, N., Miyashiro, H., et al. Triterpenes from the spores of Ganoderma lucidum and their inhibitory activity against HIV-1 protease. Chem. Pharm. Bull. 46(10), 1607-1612 (1998).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Ganoderma weberianum (#34468)

Agaricomycetes (#155619)

Ganoweberianones A and B, Antimalarial Lanostane Dimers from Cultivated Fruiting Bodies of the Basidiomycete Ganoderma weberianum.,
J Nat Prod, 2020

Pubmed ID: 33107297

String Representations

InChiKey (Click to copy)

KASALCUNLBTNAA-LIPCCPSCSA-N

InChi (Click to copy)

InChI=1S/C30H48O4/c1-19(8-11-25(33)30(7,34)18-31)20-12-16-29(6)22-9-10-23-26(2,3)24(32)14-15-27(23,4)21(22)13-17-28(20,29)5/h9,13,19-20,23,25,31,33-34H,8,10-12,14-18H2,1-7H3/t19-,20-,23+,25+,27-,28-,29+,30-/m1/s1

SMILES (Click to copy)

C1CC(=O)C(C)(C)[C@]2([H])CC=C3[C@]4([C@@]([C@](CC4)([C@@H](CC[C@@H]([C@](CO)(C)O)O)C)[H])(CC=C3[C@]21C)C)C