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

Research output: Contribution to journalArticle

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 languageEnglish
JournalNatural Product Research
DOIs
Publication statusAccepted/In press - Jan 1 2019

Fingerprint

Chrozophora
Ellagic Acid
Euphorbiaceae
ellagic acid
Diterpenes
hydroperoxides
diterpenoids
Hydrogen Peroxide
Inhibitory Concentration 50
inhibitory concentration 50
bark
Cells
Nuclear magnetic resonance
fluorouracil
Methylene Chloride
MCF-7 Cells
methylene chloride
Metabolites
Fluorouracil
breast neoplasms

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Plant Science
  • Organic Chemistry

Cite this

Ent-trachylobane-3β-hydroperoxide, a new diterpene from the root bark of Chrozophora oblongifolia (Fam.; Euphorbiaceae). / Kamel, Mohamed R.; Nafady, Alaa M.; Hassanein, Ahmed M.M.; Hassan, Ahmed R.; Shimizu, Kuniyoshi; Ibrahim, Reham R.; Haggag, Eman G.

In: Natural Product Research, 01.01.2019.

Research output: Contribution to journalArticle

Kamel, Mohamed R. ; Nafady, Alaa M. ; Hassanein, Ahmed M.M. ; Hassan, Ahmed R. ; Shimizu, Kuniyoshi ; Ibrahim, Reham R. ; Haggag, Eman G. / Ent-trachylobane-3β-hydroperoxide, a new diterpene from the root bark of Chrozophora oblongifolia (Fam.; Euphorbiaceae). In: Natural Product Research. 2019.
@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",
month = "1",
day = "1",
doi = "10.1080/14786419.2019.1687477",
language = "English",
journal = "Natural Product Research",
issn = "1478-6419",
publisher = "Taylor and Francis Ltd.",

}

TY - JOUR

T1 - Ent-trachylobane-3β-hydroperoxide, a new diterpene from the root bark of Chrozophora oblongifolia (Fam.; Euphorbiaceae)

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.

UR - http://www.scopus.com/inward/record.url?scp=85074849041&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85074849041&partnerID=8YFLogxK

U2 - 10.1080/14786419.2019.1687477

DO - 10.1080/14786419.2019.1687477

M3 - Article

C2 - 31691590

AN - SCOPUS:85074849041

JO - Natural Product Research

JF - Natural Product Research

SN - 1478-6419

ER -