Laevifins A–G, clerodane diterpenoids from the Bark of Croton oblongus Burm.f.

Ahmad Nazif Aziz; Nor Hadiani Ismail; Siti Nadiah Abdul Halim; Chung Yeng Looi; El Hassane Anouar; Moses K. Langat; Dulcie Mulholland; Khalijah Awang

doi:10.1016/j.phytochem.2018.10.002

Laevifins A–G, clerodane diterpenoids from the Bark of Croton oblongus Burm.f.

Ahmad Nazif Aziz, Nor Hadiani Ismail, Siti Nadiah Abdul Halim, Chung Yeng Looi, El Hassane Anouar, Moses K. Langat, Dulcie Mulholland, Khalijah Awang

Chemistry

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

8 Scopus citations

Abstract

A phytochemical investigation of the stem barks of the Malaysian Croton oblongus Burm.f. (Syn. Croton laevifolius Blume) (Euphorbiaceae) yielded seven previously undescribed ent-neo-clerodane diterpenoids, laevifins A - G and the known crovatin (3). Structures were established by a combination of spectroscopic methods including HRESIMS, NMR spectroscopy and X-ray crystallography. The absolute configuration of crovatin and laevifins A-G was established by comparison of experimental ECD and theoretical TDDFT ECD calculated spectra. This is the first report on the occurrence of the sesquiterpenoid cryptomeridiol in a Croton species. In vitro cytotoxicity assays on laevifins A, B and G showed moderate activities against the MCF-7 cancer cell line (IC₅₀ 102, 115 and 106 μM, respectively) while β-amyrin and acetyl aleuritolic acid showed good anti-inflammatory activity on the LPS-induced NF-κB translocation inhibition in RAW 264.7 cells assay with IC₅₀ values of 23.5 and 35.4 μg/mL, respectively.

Original language	English
Pages (from-to)	193-200
Number of pages	8
Journal	Phytochemistry
Volume	156
DOIs	https://doi.org/10.1016/j.phytochem.2018.10.002
State	Published - Dec 2018

Keywords

Croton oblongus
Cytotoxicity
Euphorbiaceae
Laevifins A – G

UN SDGs

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10.1016/j.phytochem.2018.10.002

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title = "Laevifins A–G, clerodane diterpenoids from the Bark of Croton oblongus Burm.f.",

abstract = "A phytochemical investigation of the stem barks of the Malaysian Croton oblongus Burm.f. (Syn. Croton laevifolius Blume) (Euphorbiaceae) yielded seven previously undescribed ent-neo-clerodane diterpenoids, laevifins A - G and the known crovatin (3). Structures were established by a combination of spectroscopic methods including HRESIMS, NMR spectroscopy and X-ray crystallography. The absolute configuration of crovatin and laevifins A-G was established by comparison of experimental ECD and theoretical TDDFT ECD calculated spectra. This is the first report on the occurrence of the sesquiterpenoid cryptomeridiol in a Croton species. In vitro cytotoxicity assays on laevifins A, B and G showed moderate activities against the MCF-7 cancer cell line (IC50 102, 115 and 106 μM, respectively) while β-amyrin and acetyl aleuritolic acid showed good anti-inflammatory activity on the LPS-induced NF-κB translocation inhibition in RAW 264.7 cells assay with IC50 values of 23.5 and 35.4 μg/mL, respectively.",

keywords = "Croton oblongus, Cytotoxicity, Euphorbiaceae, Laevifins A – G",

author = "Aziz, \{Ahmad Nazif\} and Ismail, \{Nor Hadiani\} and Halim, \{Siti Nadiah Abdul\} and Looi, \{Chung Yeng\} and Anouar, \{El Hassane\} and Langat, \{Moses K.\} and Dulcie Mulholland and Khalijah Awang",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = dec,

doi = "10.1016/j.phytochem.2018.10.002",

language = "English",

volume = "156",

pages = "193--200",

journal = "Phytochemistry",

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T1 - Laevifins A–G, clerodane diterpenoids from the Bark of Croton oblongus Burm.f.

AU - Aziz, Ahmad Nazif

AU - Ismail, Nor Hadiani

AU - Halim, Siti Nadiah Abdul

AU - Looi, Chung Yeng

AU - Anouar, El Hassane

AU - Langat, Moses K.

AU - Mulholland, Dulcie

AU - Awang, Khalijah

PY - 2018/12

Y1 - 2018/12

N2 - A phytochemical investigation of the stem barks of the Malaysian Croton oblongus Burm.f. (Syn. Croton laevifolius Blume) (Euphorbiaceae) yielded seven previously undescribed ent-neo-clerodane diterpenoids, laevifins A - G and the known crovatin (3). Structures were established by a combination of spectroscopic methods including HRESIMS, NMR spectroscopy and X-ray crystallography. The absolute configuration of crovatin and laevifins A-G was established by comparison of experimental ECD and theoretical TDDFT ECD calculated spectra. This is the first report on the occurrence of the sesquiterpenoid cryptomeridiol in a Croton species. In vitro cytotoxicity assays on laevifins A, B and G showed moderate activities against the MCF-7 cancer cell line (IC50 102, 115 and 106 μM, respectively) while β-amyrin and acetyl aleuritolic acid showed good anti-inflammatory activity on the LPS-induced NF-κB translocation inhibition in RAW 264.7 cells assay with IC50 values of 23.5 and 35.4 μg/mL, respectively.

AB - A phytochemical investigation of the stem barks of the Malaysian Croton oblongus Burm.f. (Syn. Croton laevifolius Blume) (Euphorbiaceae) yielded seven previously undescribed ent-neo-clerodane diterpenoids, laevifins A - G and the known crovatin (3). Structures were established by a combination of spectroscopic methods including HRESIMS, NMR spectroscopy and X-ray crystallography. The absolute configuration of crovatin and laevifins A-G was established by comparison of experimental ECD and theoretical TDDFT ECD calculated spectra. This is the first report on the occurrence of the sesquiterpenoid cryptomeridiol in a Croton species. In vitro cytotoxicity assays on laevifins A, B and G showed moderate activities against the MCF-7 cancer cell line (IC50 102, 115 and 106 μM, respectively) while β-amyrin and acetyl aleuritolic acid showed good anti-inflammatory activity on the LPS-induced NF-κB translocation inhibition in RAW 264.7 cells assay with IC50 values of 23.5 and 35.4 μg/mL, respectively.

KW - Croton oblongus

KW - Cytotoxicity

KW - Euphorbiaceae

KW - Laevifins A – G

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U2 - 10.1016/j.phytochem.2018.10.002

DO - 10.1016/j.phytochem.2018.10.002

M3 - Article

C2 - 30316148

AN - SCOPUS:85054462501

SN - 0031-9422

VL - 156

SP - 193

EP - 200

JO - Phytochemistry

JF - Phytochemistry

ER -

Laevifins A–G, clerodane diterpenoids from the Bark of Croton oblongus Burm.f.

Abstract

Keywords

UN SDGs

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