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Research Project: Biobased Pesticide Discovery and Product Optimization and Enhancement from Medicinal and Aromatic Crops

Location: Natural Products Utilization Research

Title: Antiplasmodial and antimicrobial activities of ent-abietane diterpenoids from the roots of Suregada zanzibariensis

item MATUNDURA, JACKSON - University Of Nairobi
item MIDIWO, JACOB - University Of Nairobi
item YENESEW, ABIY - University Of Nairobi
item OMOSA, LEONIDAH - University Of Nairobi
item KUMARIHAMY, MALLIKA - University Of Mississippi
item ZHAO, JIANPING - University Of Mississippi
item Wang, Mei
item TRIPATHI, SIDDHARTH - University Of Mississippi
item KHAN, SHABANA - University Of Mississippi
item MASILA, VERONICA - University Of Nairobi
item MUHAMMAD, ILIAS - University Of Mississippi

Submitted to: Natural Product Research
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 12/9/2022
Publication Date: 12/28/2022
Citation: Matundura, J.O., Midiwo, J.O., Yenesew, A., Omosa, L., Kumarihamy, M., Zhao, J., Wang, M., Tripathi, S., Khan, S., Masila, V.M., Nchiozem-Ngnitedem, V., Muhammad, I. 2022. Antiplasmodial and antimicrobial activities of ent-abietane diterpenoids from the roots of Suregada zanzibariensis. Natural Product Research.

Interpretive Summary: Mosquito-borne diseases are major challenges and significant health concern in many African countries. Among them, malaria is the most widespread that affects mostly children under the age of 5 years. Fungal and bacterial infections by opportunistic pathogens are the principal causes of various chronic diseases, especially in patients with compromised immunity such as cancer and human immunodefeciency virus. In continuation to our investigation of anti-infective agents from medicinal plants, phytochemical investigation of the roots of Suregada zanzibariensis was undertaken. Nine compounds were isolated and characterized. The significance of antiplasmodial, antifungal and antibacterial activities of the isolated compounds were reported.

Technical Abstract: The roots extract of Suregada zanzibariensis afforded six previously described ent-abietane diterpenoids, namely 7-oxo-ent-abieta-5(6),8(14),13(15)-trien-16,12-olide (1), mangiolide (2), 8,14ß:11,12a-diepoxy-13(15)-abietane-16,12-olide (3), 7ß,11ß,12ß-trihydroxy-ent–abieta-8(14),13(15)-diene-16,12-olide (4), 8a,14-dihydro-7-oxo-jolkinolide E (5), jolkinolide A (6), together with 3ß-sitosterol (7), scopoletin (8) and vanillin (9). All compounds, except 2, are reported from S. zanzibariensis for the first time. The chemophenetic significance of these isolates is also discussed. Their structures were deduced through 1D and 2D NMR spectroscopic techniques, and HRESIMS, as well as by comparison of the NMR data with those reported in the literature. The crude extract and compounds 1 – 9 were evaluated for their antiplasmodial, antifungal and antibacterial activities. Among diterpenes (1 – 6), mangiolide (2) showed strong in vitro antiplasmodial activity against chloroquine sensitive (D6) and resistant (W2) strains of Plasmodium falciparum with IC50 values of 0.79 and 0.87 µg/mL, respectively, while 3 (IC50 1.24 and 1.17 µg/mL) was less active than 2. Compound 2 also displayed antimicrobial activity against Cryptococcus neoformans, methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VRE) with IC50 values of 1.20, 3.90 and 7.20 µg/mL, respectively.