Ent-trachylobane-3β-hydroperoxide, a new diterpene from the root bark of Chrozophora oblongifolia (Fam.; Euphorbiaceae)

Mohamed R. Kamel; Alaa M. Nafady; Ahmed M.M. Hassanein; Ahmed R. Hassan; Kuniyoshi Shimizu; Reham R. Ibrahim; Eman G. Haggag

doi:10.1080/14786419.2019.1687477

Ent-trachylobane-3β-hydroperoxide, a new diterpene from the root bark of Chrozophora oblongifolia (Fam.; Euphorbiaceae)

Mohamed R. Kamel, Alaa M. Nafady, Ahmed M.M. Hassanein, Ahmed R. Hassan, Kuniyoshi Shimizu, Reham R. Ibrahim, Eman G. Haggag

Sustainable Bioresources Science

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

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Abstract

New ent-trachylobane-3β-hydroperoxide (5) together with four known compounds, ricinine (1), trimethoxy ellagic acid (2), dimethoxy ellagic acid (3) and aleurotolic acid (4) were isolated from the methylene chloride fraction of the root bark of Chrozophora oblongifolia. The structures of these secondary metabolites were elucidated by using different spectroscopic techniques, ¹H NMR, ¹³C NMR, HSQC, HMBC, ¹H-¹H COSY, NOESY, HR-ESI-MS, EI-MS and comparison with published data. Ent-trachylobane-3β-hydroperoxide showed moderate cytotoxic activity by MTT assay method against human breast cancer cells (MCF-7) and human hepatocyte-derived carcinoma cells (Huh-7) with IC₅₀ values of 24.53 and 34.13 µM, in comparison with IC₅₀ values of 23.47 µM and 15.82 µM for 5-fluorouracil respectively.

Original language	English
Journal	Natural Product Research
DOIs	https://doi.org/10.1080/14786419.2019.1687477
Publication status	Accepted/In press - Jan 1 2019

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Biochemistry
Plant Science
Organic Chemistry

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@article{f0f6c89d024f4c769de446d66c6d76f6,

title = "Ent-trachylobane-3β-hydroperoxide, a new diterpene from the root bark of Chrozophora oblongifolia (Fam.; Euphorbiaceae)",

abstract = "New ent-trachylobane-3β-hydroperoxide (5) together with four known compounds, ricinine (1), trimethoxy ellagic acid (2), dimethoxy ellagic acid (3) and aleurotolic acid (4) were isolated from the methylene chloride fraction of the root bark of Chrozophora oblongifolia. The structures of these secondary metabolites were elucidated by using different spectroscopic techniques, 1H NMR, 13C NMR, HSQC, HMBC, 1H-1H COSY, NOESY, HR-ESI-MS, EI-MS and comparison with published data. Ent-trachylobane-3β-hydroperoxide showed moderate cytotoxic activity by MTT assay method against human breast cancer cells (MCF-7) and human hepatocyte-derived carcinoma cells (Huh-7) with IC50 values of 24.53 and 34.13 µM, in comparison with IC50 values of 23.47 µM and 15.82 µM for 5-fluorouracil respectively.",

author = "Kamel, {Mohamed R.} and Nafady, {Alaa M.} and Hassanein, {Ahmed M.M.} and Hassan, {Ahmed R.} and Kuniyoshi Shimizu and Ibrahim, {Reham R.} and Haggag, {Eman G.}",

year = "2019",

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doi = "10.1080/14786419.2019.1687477",

language = "English",

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AU - Kamel, Mohamed R.

AU - Nafady, Alaa M.

AU - Hassanein, Ahmed M.M.

AU - Hassan, Ahmed R.

AU - Shimizu, Kuniyoshi

AU - Ibrahim, Reham R.

AU - Haggag, Eman G.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - New ent-trachylobane-3β-hydroperoxide (5) together with four known compounds, ricinine (1), trimethoxy ellagic acid (2), dimethoxy ellagic acid (3) and aleurotolic acid (4) were isolated from the methylene chloride fraction of the root bark of Chrozophora oblongifolia. The structures of these secondary metabolites were elucidated by using different spectroscopic techniques, 1H NMR, 13C NMR, HSQC, HMBC, 1H-1H COSY, NOESY, HR-ESI-MS, EI-MS and comparison with published data. Ent-trachylobane-3β-hydroperoxide showed moderate cytotoxic activity by MTT assay method against human breast cancer cells (MCF-7) and human hepatocyte-derived carcinoma cells (Huh-7) with IC50 values of 24.53 and 34.13 µM, in comparison with IC50 values of 23.47 µM and 15.82 µM for 5-fluorouracil respectively.

AB - New ent-trachylobane-3β-hydroperoxide (5) together with four known compounds, ricinine (1), trimethoxy ellagic acid (2), dimethoxy ellagic acid (3) and aleurotolic acid (4) were isolated from the methylene chloride fraction of the root bark of Chrozophora oblongifolia. The structures of these secondary metabolites were elucidated by using different spectroscopic techniques, 1H NMR, 13C NMR, HSQC, HMBC, 1H-1H COSY, NOESY, HR-ESI-MS, EI-MS and comparison with published data. Ent-trachylobane-3β-hydroperoxide showed moderate cytotoxic activity by MTT assay method against human breast cancer cells (MCF-7) and human hepatocyte-derived carcinoma cells (Huh-7) with IC50 values of 24.53 and 34.13 µM, in comparison with IC50 values of 23.47 µM and 15.82 µM for 5-fluorouracil respectively.

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