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Structure Database (LMSD)

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Common Name

(+)-Tirucallol

Systematic Name

(20S)-(+)-triucalla-8,24-diene-3β-ol

Synonyms

LM ID

LMPR0106090001

Formula

C₃₀H₅₀O

Exact Mass

Calculate m/z

426.386166

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Tirucallol is a triterpenoid that has been found in Camellia and has reverse transcriptase inhibitory and anti-inflammatory activities.^1,2 It inhibits HIV-1 reverse transcriptase (IC50 = 3.8 µM).¹ Tirucallol (25, 50, and 100 µM) reduces nitric oxide (NO) and prostaglandin E2 (PGE2) production in LPS-stimulated isolated mouse peritoneal macrophages.² Topical application of tirucallol (0.25, 0.5, and 1 mg/ear) reduces ear edema induced by phorbol 12-myristate 13-acetate (TPA) in mice.

This information has been provided by Cayman Chemical

References

1. Akihisa, T., Ogihara, J., Kato, J., et al. Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase. Lipids 36(5), 507-512 (2001).

2. Fernandez-Arche, A., Saenz, M.T., Arroyo, M., et al. Topical anti-inflammatory effect of tirucallol, a triterpene isolated from Euphorbia lactea latex. Phytomedicine 17(2), 146-148 (2010).

References

Reference

Breitmaier, E. Terpenes: flavors, fragrances, pharmaca, pheromones. Weinheim, Germany: WILEY-VCH, 2006.

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Euphorbia tirucalli (#142860)

Magnoliopsida (#3398)

Rotational isomerism about the 17(20)-bond of steroids and euphoids as shown by the crystal structures of euphol and tirucallol.,
Proc Natl Acad Sci U S A, 1984

Pubmed ID: 6592593

String Representations

InChiKey (Click to copy)

CAHGCLMLTWQZNJ-HGKXYCPESA-N

InChi (Click to copy)

InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25-,26-,28+,29-,30+/m0/s1

SMILES (Click to copy)

C1C[C@]2(C)C3CC[C@@]4(C)[C@]([H])([C@@]([H])(C)CC/C=C(\C)/C)CC[C@]4(C)C=3CC[C@@]2([H])C(C)(C)[C@H]1O