Bisbenzylisoquinoline and hasubanane alkaloids from Stephania abyssinica (Dillon & A. Rich) (Menispermeceae)

Ruth A Omole; Jeremiah Gathirwa; Hosea Akala; Hamisi M Malebo; Alex K Machocho; Ahmed Hassanali; Isaiah O Ndiege

doi:10.1016/j.phytochem.2014.03.026

Bisbenzylisoquinoline and hasubanane alkaloids from Stephania abyssinica (Dillon & A. Rich) (Menispermeceae)

Phytochemistry. 2014 Jul:103:123-128. doi: 10.1016/j.phytochem.2014.03.026. Epub 2014 Apr 12.

Authors

Ruth A Omole¹, Jeremiah Gathirwa², Hosea Akala³, Hamisi M Malebo⁴, Alex K Machocho⁵, Ahmed Hassanali⁶, Isaiah O Ndiege⁷

Affiliations

¹ Department of Chemistry, Kenyatta University, P.O. Box 43844, Nairobi 00100, Kenya; Department of Chemical Science and Technology, Technical University of Kenya, P.O Box 52428, Nairobi 00200, Kenya. Electronic address: oruth2002@yahoo.com.
² Centre for Traditional Medicine & Drug Research, Kenya Medical Research Institute (KEMRI), P.O Box 54840, Nairobi 00200, Kenya. Electronic address: jgathirwa@gmail.com.
³ Department of Emerging Infectious Diseases-Global Emerging Infections Surveillance and Response System (DEID-GEIS) Program, United States Army Medical Research Unit-Kenya (USAMRU-K), Kenya Medical Research Institute (KEMRI)-Walter Reed Project, P.O. Box 54, 40100 Kisumu, Kenya. Electronic address: hoseaakala@yahoo.com.
⁴ Department of Traditional Medicine Research, National Institute for Medical Research (NIMR), P.O. Box 9653, Dar es Salaam, Tanzania. Electronic address: malebo@hotmail.com.
⁵ Department of Chemistry, Kenyatta University, P.O. Box 43844, Nairobi 00100, Kenya. Electronic address: machochoalex@hotmail.com.
⁶ Department of Chemistry, Kenyatta University, P.O. Box 43844, Nairobi 00100, Kenya; Behavioural & Chemical Ecology Department, International Centre for Insect Physiology & Ecology (ICIPE), P.O. Box 30772, Nairobi 00100, Kenya. Electronic address: ahmedhassanali786@gmail.com.
⁷ Department of Chemistry, Kenyatta University, P.O. Box 43844, Nairobi 00100, Kenya; Office of the Vice Chancellor, Kyambogo University, P.O. Box 1, Kyambogo, Kampala, Uganda. Electronic address: indiege@yahoo.com.

PMID: 24735823
DOI: 10.1016/j.phytochem.2014.03.026

Abstract

Two bisbenzylisoquinoline and one hasubanane alkaloids: (-)-pseudocurine (1), (-)-pseudoisocurine (2) and (-)-10-oxoaknadinine (3), were isolated from leaf extract of Stephania abyssinica, a plant used in traditional medicine in South Nyanza region of Kenya. They were characterized using 1D ((1)H, (13)C and DEPT) and 2D (COSY, NOESY, HMQC and HMBC) NMR techniques. (-)-Pseudocurine (1) and (-)-pseudoisocurine (2) exhibited strong to moderate anti-plasmodial activity while (-)-10-oxoaknadinine (3) showed moderate to mild activity.

Keywords: (−)-10-oxoaknadinine anti-plasmodial activity; (−)-Pseudocurine and (−)-pseudoisocurine; Alkaloids; Bisbenzylisoquinoline; Hasubanane; Menispermerceae; Stephania abyssinica.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry*
Alkaloids / pharmacology*
Antimalarials / chemistry*
Antimalarials / pharmacology*
Benzylisoquinolines / chemistry*
Benzylisoquinolines / pharmacology*
Magnetic Resonance Spectroscopy
Molecular Structure
Plasmodium falciparum / drug effects
Stephania / chemistry*

Substances

Alkaloids
Antimalarials
Benzylisoquinolines