New anti-trypanosomal active tetracyclic iridoid isolated from Morinda lucida Benth.

Mitsuko Suzuki, Nguyen Huu Tung, Kofi D. Kwofie, Richard Adegle, Michael Amoa-Bosompem, Maxwell Sakyiamah, Frederick Ayertey, Kofi Baffour Awuah Owusu, Isaac Tuffour, Philip Atchoglo, Kwadwo Kyereme Frempong, William K. Anyan, Takuhiro Uto, Osamu Morinaga, Taizo Yamashita, Frederic Aboagye, Alfred Ampomah Appiah, Regina Appiah-Opong, Alexander K. Nyarko, Shoji YamaokaYasuchika Yamaguchi, Dominic Edoh, Kwadwo Koram, Nobuo Ohta, Daniel A. Boakye, Irene Ayi, Yukihiro Shoyama

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

Human African trypanosomiasis (HAT), commonly known as sleeping sickness has remained a serious health problem in many African countries with thousands of new infected cases annually. Chemotherapy, which is the main form of control against HAT has been characterized lately by the viewpoints of toxicity and drug resistance issues. Recently, there have been a lot of emphases on the use of medicinal plants world-wide. Morinda lucida Benth. is one of the most popular medicinal plants widely distributed in Africa and several groups have reported on its anti-protozoa activities. In this study, we have isolated one novel tetracyclic iridoid, named as molucidin, from the CHCl3 fraction of the M. lucida leaves by bioassay-guided fractionation and purification. Molucidin was structurally elucidated by 1H and 13C NMR including HMQC, HMBC, H-H COSY and NOESY resulting in tetracyclic iridoid skeleton, and its absolute configuration was determined. We have further demonstrated that molucidin presented a strong anti-trypanosomal activity, indicating an IC50 value of 1.27 μM. The cytotoxicity study using human normal and cancer cell lines indicated that molucidin exhibited selectivity index (SI) against two normal fibroblasts greater than 4.73. Furthermore, structure-activity relationship (SAR) study was undertaken with molucidin and oregonin, which is identical to anti-trypanosomal active components of Alnus japonica. Overlapping analysis of the lowest energy conformation of molucidin with oregonin suggested a certain similarities of aromatic rings of both oregonin and molucidin. These results contribute to the future drug design studies for HAT.

Original languageEnglish
Pages (from-to)3030-3033
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume25
Issue number15
DOIs
Publication statusPublished - Jun 11 2015
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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