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

9 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

This output contributes to the following UN Sustainable Development Goals (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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TY - JOUR

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

UR - https://www.scopus.com/pages/publications/85054462501

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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