Two clerodane diterpenes isolated from Polyalthia longifolia leaves: comparative structural features, anti-histaminic and anti-Helicobacter pylori activities

Abstract

Phytochemical studies of methylene chloride soluble fraction from the 70% aqueous-alcoholic extract of Polyalthia longifolia (leaves) resulted in the isolation of two known clerodane diterpenes, namely: 16α-hydroxycleroda-3,13(14)-dien-16,15-olide (1) and (4→2)-abeo-16-hydroxy-cleroda-2,13(14)-dien-15,16-olide-3-al (2). The isolated compounds were evaluated for their anti-histaminic and anti-Helicobacter pylori activities. Compound 1 was more potent than 2 with IC₅₀ 29.7 μg/mL and 189.2 μg/mL in the anti-histaminic assay and MIC equals to 31.25 μg/mL and 125 μg/mL in the anti-H. pylori assay, as compared with diclofenac (IC₅₀ = 17.9 μg/mL) and clarithromycin (MIC = 1.95 μg/mL), respectively. The differences in their structures, as well as their activity results, indicated important characteristic features necessary for activity. It was suggested that the decalin moiety in 1 was important for both activities. On the other hand, the (4→2)-abeo migration in 2 reduced both activities. The potent activities of 1 suggest its potential application as an anti-histaminic and antimicrobial agent.

Graphical Abstract

Keywords:

• Polyalthia longifolia
• anti-histaminic
• diterpenes
• anti-helicobacter pylori
• clerodane

Disclosure statement

The authors declare no conflicts of interest.

Additional information

Funding

The authors acknowledge Egyptian Science and Technology Development Funds (STDF) for its financial support entitled “Center for Drug Discovery and Development Research”, Faculty of Pharmacy, Ain Shams University.