Structure, anti-Phytophthora and anti-tumor activities of a nortriterpenoid from the rhizome of Phlomis purpurea (Lamiaceae)

Maria C Mateus; Dina Neves; Bruno Dacunha; Endre Laczko; Cristiana Maia; Rúben Teixeira; Alfredo Cravador

doi:10.1016/j.phytochem.2016.09.004

Structure, anti-Phytophthora and anti-tumor activities of a nortriterpenoid from the rhizome of Phlomis purpurea (Lamiaceae)

Phytochemistry. 2016 Nov:131:158-164. doi: 10.1016/j.phytochem.2016.09.004. Epub 2016 Sep 15.

Authors

Maria C Mateus¹, Dina Neves², Bruno Dacunha³, Endre Laczko⁴, Cristiana Maia², Rúben Teixeira², Alfredo Cravador⁵

Affiliations

¹ Chemistry Research Centre of Algarve (CIQA), Faculdade de Ciências e Tecnologia, Universidade do Algarve, Campus de Gambelas, 8005-139, Faro, Portugal.
² Faculdade de Ciências e Tecnologia, Universidade do Algarve, Campus de Gambelas, 8005-139, Faro, Portugal.
³ Unidade de Difraccion de RaiosX, RIAIDT, Edificio CACTUS, Campus Sur, 15782, Santiago de Compostela, A Coruña, Spain.
⁴ Functional Genomics Center, UZH / ETHZ, Winterthurerstr. 190, CH-8057, Zürich, Switzerland.
⁵ Centre for Mediterranean Bioresourses and Food, FCT, Universidade do Algarve, Campus de Gambelas, 8005-139, Faro, Portugal. Electronic address: acravad@ualg.pt.

PMID: 27641672
DOI: 10.1016/j.phytochem.2016.09.004

Abstract

To investigate bioactive compounds potentially involved in the biotic interactions exhibited by Phlomis purpurea (Lamiaceae) in rhizospheres infested with Phytophthora cinnamomi, the plant rhizome was chemically analysed. The nortriterpenoid (17S)-2α,3α,11α,23,24-pentahydroxy-19(18 → 17)-abeo-28-norolean-12-en-18-one, was isolated and its structure was elucidated by comprehensive spectroscopic analysis, chiefly using 2D NMR experiments, and X-ray analysis. It was shown to be exuded by roots and to exhibit anti-Phytophthora and antitumor activities.

Keywords: Anti-Phytophthora; Bioassays; Chemical structure; Cytotoxic activity; Exudate; Lamiaceae; Phlomis purpurea; Triterpene.

MeSH terms

Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification*
Antineoplastic Agents, Phytogenic / pharmacology*
Drug Screening Assays, Antitumor
Glycosides / chemistry
HeLa Cells
Humans
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Phlomis / chemistry*
Phytophthora / drug effects*
Plant Roots / chemistry
Portugal
Rhizome / chemistry
Triterpenes / chemistry
Triterpenes / isolation & purification*
Triterpenes / pharmacology*

Substances

Antineoplastic Agents, Phytogenic
Glycosides
Triterpenes