Anti-HIV Ermiasolides from Croton megalocarpus

Ermias Mergia Terefe; Faith Apolot Okalebo; Solomon Derese; Moses K. Langat; Eduard Mas-Claret; Kamal A. Qureshi; Mariusz Jaremko; Joseph Muriuki

doi:10.3390/molecules27207040

Anti-HIV Ermiasolides from Croton megalocarpus

Ermias Mergia Terefe, Faith Apolot Okalebo, Solomon Derese, Moses K. Langat, Eduard Mas-Claret, Kamal A. Qureshi, Mariusz Jaremko, Joseph Muriuki

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

In recent years, elucidation of novel anti-HIV bioactive compounds from natural products is gaining importance rapidly, not only from the research and publications, but also from controlled clinical studies. Here we report three new anti-HIV eudesmane-type sesquiterpenes, 5β-Hydroxy-8α-methoxy eudesm-7(11)-en-12,8-olide (1), 5β,8α-Dihydroxy eudesm-7(11)-en-12,8-olide (2) and 5β-Hydroxy-8H-β-eudesm-7(11)-en-12,8-olide (3). These are trivially named ermiasolide A-C and were isolated from the bark of Croton megalocarpus. 5β-Hydroxy-8α-methoxy eudesm-7(11)-en-12,8-olide (1), showed the highest anti-HIV activity by inhibiting 93% of the viral replication with an IC50 = 0.002 µg/mL. On the other hand, 5β-Hydroxy-8H-β-eudesm-7(11)-en-12,8-olide (3) and 5β,8α-dihydroxy eudesm-7(11)-en-12,8-olide (2), inhibited viral replication by 77.5% at IC50 = 0.04 µg/mL and 69.5% at IC50 = 0.002 µg/mL, respectively. Molecular docking studies showed that the proposed mechanism of action leading to these results is through the inhibition of HIV-protease.

Original language	English (US)
Pages (from-to)	7040
Journal	Molecules
Volume	27
Issue number	20
DOIs	https://doi.org/10.3390/molecules27207040
State	Published - Oct 19 2022

Bibliographical note

KAUST Repository Item: Exported on 2022-10-21
Acknowledgements: This research was funded by the King Abdullah University of Science and Technology, Thuwal, Jeddah, Saudi Arabia and United States International University, Nairobi, Kenya. EMT acknowledges United States International University-Africa Internal Grant No. 10-2854, and University of Nairobi, Kenya Medical Research institute, the Institute of Primate Research and King Abdullah University of Science and Technology for their support toward the successful completion of the research work.

ASJC Scopus subject areas

Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/molecules27207040

https://repository.kaust.edu.sa/bitstream/10754/685041/1/molecules-27-07040.pdf

Cite this

@article{490e110bb9d44d5db64e7691a2cc740b,

title = "Anti-HIV Ermiasolides from Croton megalocarpus",

abstract = "In recent years, elucidation of novel anti-HIV bioactive compounds from natural products is gaining importance rapidly, not only from the research and publications, but also from controlled clinical studies. Here we report three new anti-HIV eudesmane-type sesquiterpenes, 5β-Hydroxy-8α-methoxy eudesm-7(11)-en-12,8-olide (1), 5β,8α-Dihydroxy eudesm-7(11)-en-12,8-olide (2) and 5β-Hydroxy-8H-β-eudesm-7(11)-en-12,8-olide (3). These are trivially named ermiasolide A-C and were isolated from the bark of Croton megalocarpus. 5β-Hydroxy-8α-methoxy eudesm-7(11)-en-12,8-olide (1), showed the highest anti-HIV activity by inhibiting 93% of the viral replication with an IC50 = 0.002 µg/mL. On the other hand, 5β-Hydroxy-8H-β-eudesm-7(11)-en-12,8-olide (3) and 5β,8α-dihydroxy eudesm-7(11)-en-12,8-olide (2), inhibited viral replication by 77.5% at IC50 = 0.04 µg/mL and 69.5% at IC50 = 0.002 µg/mL, respectively. Molecular docking studies showed that the proposed mechanism of action leading to these results is through the inhibition of HIV-protease.",

author = "Terefe, {Ermias Mergia} and Okalebo, {Faith Apolot} and Solomon Derese and Langat, {Moses K.} and Eduard Mas-Claret and Qureshi, {Kamal A.} and Mariusz Jaremko and Joseph Muriuki",

note = "KAUST Repository Item: Exported on 2022-10-21 Acknowledgements: This research was funded by the King Abdullah University of Science and Technology, Thuwal, Jeddah, Saudi Arabia and United States International University, Nairobi, Kenya. EMT acknowledges United States International University-Africa Internal Grant No. 10-2854, and University of Nairobi, Kenya Medical Research institute, the Institute of Primate Research and King Abdullah University of Science and Technology for their support toward the successful completion of the research work.",

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month = oct,

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doi = "10.3390/molecules27207040",

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AU - Terefe, Ermias Mergia

AU - Okalebo, Faith Apolot

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AU - Langat, Moses K.

AU - Mas-Claret, Eduard

AU - Qureshi, Kamal A.

AU - Jaremko, Mariusz

AU - Muriuki, Joseph

N1 - KAUST Repository Item: Exported on 2022-10-21 Acknowledgements: This research was funded by the King Abdullah University of Science and Technology, Thuwal, Jeddah, Saudi Arabia and United States International University, Nairobi, Kenya. EMT acknowledges United States International University-Africa Internal Grant No. 10-2854, and University of Nairobi, Kenya Medical Research institute, the Institute of Primate Research and King Abdullah University of Science and Technology for their support toward the successful completion of the research work.

PY - 2022/10/19

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N2 - In recent years, elucidation of novel anti-HIV bioactive compounds from natural products is gaining importance rapidly, not only from the research and publications, but also from controlled clinical studies. Here we report three new anti-HIV eudesmane-type sesquiterpenes, 5β-Hydroxy-8α-methoxy eudesm-7(11)-en-12,8-olide (1), 5β,8α-Dihydroxy eudesm-7(11)-en-12,8-olide (2) and 5β-Hydroxy-8H-β-eudesm-7(11)-en-12,8-olide (3). These are trivially named ermiasolide A-C and were isolated from the bark of Croton megalocarpus. 5β-Hydroxy-8α-methoxy eudesm-7(11)-en-12,8-olide (1), showed the highest anti-HIV activity by inhibiting 93% of the viral replication with an IC50 = 0.002 µg/mL. On the other hand, 5β-Hydroxy-8H-β-eudesm-7(11)-en-12,8-olide (3) and 5β,8α-dihydroxy eudesm-7(11)-en-12,8-olide (2), inhibited viral replication by 77.5% at IC50 = 0.04 µg/mL and 69.5% at IC50 = 0.002 µg/mL, respectively. Molecular docking studies showed that the proposed mechanism of action leading to these results is through the inhibition of HIV-protease.

AB - In recent years, elucidation of novel anti-HIV bioactive compounds from natural products is gaining importance rapidly, not only from the research and publications, but also from controlled clinical studies. Here we report three new anti-HIV eudesmane-type sesquiterpenes, 5β-Hydroxy-8α-methoxy eudesm-7(11)-en-12,8-olide (1), 5β,8α-Dihydroxy eudesm-7(11)-en-12,8-olide (2) and 5β-Hydroxy-8H-β-eudesm-7(11)-en-12,8-olide (3). These are trivially named ermiasolide A-C and were isolated from the bark of Croton megalocarpus. 5β-Hydroxy-8α-methoxy eudesm-7(11)-en-12,8-olide (1), showed the highest anti-HIV activity by inhibiting 93% of the viral replication with an IC50 = 0.002 µg/mL. On the other hand, 5β-Hydroxy-8H-β-eudesm-7(11)-en-12,8-olide (3) and 5β,8α-dihydroxy eudesm-7(11)-en-12,8-olide (2), inhibited viral replication by 77.5% at IC50 = 0.04 µg/mL and 69.5% at IC50 = 0.002 µg/mL, respectively. Molecular docking studies showed that the proposed mechanism of action leading to these results is through the inhibition of HIV-protease.

UR - http://hdl.handle.net/10754/685041

UR - https://www.mdpi.com/1420-3049/27/20/7040

U2 - 10.3390/molecules27207040

DO - 10.3390/molecules27207040

M3 - Article

C2 - 36296633

SN - 1420-3049

VL - 27

SP - 7040

JO - Molecules

JF - Molecules

IS - 20

ER -

Anti-HIV Ermiasolides from Croton megalocarpus

Abstract

Bibliographical note

ASJC Scopus subject areas

UN SDGs

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