Diterpenoids from the roots of Croton dichogamus Pax

Areej Aldhaher; Moses Langat; Beth Ndunda; Denis Chirchir; Jacob O Midiwo; Alice Njue; Sianne Schwikkard; Mark Carew; Dulcie Mulholland

doi:10.1016/j.phytochem.2017.08.014

Diterpenoids from the roots of Croton dichogamus Pax

Phytochemistry. 2017 Dec:144:1-8. doi: 10.1016/j.phytochem.2017.08.014. Epub 2017 Sep 1.

Authors

Areej Aldhaher¹, Moses Langat², Beth Ndunda³, Denis Chirchir⁴, Jacob O Midiwo⁵, Alice Njue⁶, Sianne Schwikkard⁷, Mark Carew⁷, Dulcie Mulholland⁸

Affiliations

¹ Natural Products Research Group, Department of Chemistry, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, GU2 7XH, United Kingdom; Department of Biology, College of Science, Basrah University, Basrah, Iraq.
² Natural Products Research Group, Department of Chemistry, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, GU2 7XH, United Kingdom; School of Chemistry and Physics, University of Natal, Durban, 4041, South Africa.
³ Natural Products Research Group, Department of Chemistry, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, GU2 7XH, United Kingdom; Department of Chemistry, University of Nairobi, P Bag 30197-00100, Nairobi, Kenya.
⁴ Department of Chemistry, Egerton University, P.O. Box 536, Njoro, 20115, Kenya.
⁵ Department of Chemistry, University of Nairobi, P Bag 30197-00100, Nairobi, Kenya.
⁶ Natural Products Research Group, Department of Chemistry, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, GU2 7XH, United Kingdom; Department of Chemistry, Egerton University, P.O. Box 536, Njoro, 20115, Kenya.
⁷ Department of Chemistry, School of Life Sciences, Pharmacy and Chemistry, Kingston University, Penrhyn Road, Kingston, KT1 2EE, United Kingdom.
⁸ Natural Products Research Group, Department of Chemistry, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, GU2 7XH, United Kingdom; School of Chemistry and Physics, University of Natal, Durban, 4041, South Africa. Electronic address: d.mulholland@surrey.ac.uk.

PMID: 28863305
DOI: 10.1016/j.phytochem.2017.08.014

Abstract

Four previously undescribed diterpenoids including two crotofolanes, crotodichogamoin A and B, and two halimanes, crothalimene A and B, a new sesquiterpenoid, and fifteen previously reported compounds, including the crotofolane, crotohaumanoxide, the casbane, depressin, a further seven furanohalimane diterpenoids, three patchoulane and two further cadinane sesquiterpenoids and aleuritolic acid were isolated from the root of Croton dichogamus. Crotodichogamoin B is an important biosynthetic intermediate of the crotofolane class and this is the first report of patchoulene sesquiterpenoids from the genus. Compounds were tested at one concentration, 1 × 10^-5 M, in the NCI59 cell one-dose screen but did not show significant activity snd were also evaluated for their cytotoxicity against Caco-2 cell lines using the neutral red assay. 10-epi-Maninsigin D reduced Caco-2 cell viability at 10, 30 and 100 μM, with values of decreased viability of 28%, 48% and 43% respectively. None of the other tested compounds showed significant activity.

Keywords: Caco-2 cell viability; Crothalimene A; Crothalimene B; Crotodichogamoin B; Crotofolane; Croton dichogamus; Euphorbiaceae; Patchoulane.

MeSH terms

Caco-2 Cells
Cell Survival / drug effects
Croton / chemistry*
Diterpenes / chemistry
Diterpenes / isolation & purification
Diterpenes / pharmacology*
Dose-Response Relationship, Drug
Humans
Molecular Conformation
Plant Roots / chemistry*
Structure-Activity Relationship

Substances

Diterpenes