New Safrole Oxide Derivatives: Synthesis and in vitro Antiproliferative Activities on A549 Human Lung Cancer Cells

Wang, Liying; Wang, Xiuhua; Tan, Jia‐Lian; Xia, Shuai; Sun, Hengzhi; Shi, Jinwen; Jiang, Mingdong; Fang, Liang; Zuo, Hua; Dupati, Gautam; Jang, Kiwan; Shin, Dong‐Soo

doi:10.5012/bkcs.2012.33.11.3571

Cited by 4 publications

(4 citation statements)

References 9 publications

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“…Several of these compounds, have been present a potent cytotoxic activity against two breast cancer cell lines, MCF-7, MDA-MB231 7,8 , including safrole oxide and 1-ethoxy-3-(3,4-methylenedioxyphenyl)-2-propanol (EOD), have been found to inhibit angiogenesis 9 and to arrest the growth and induce death of human tumor cells in vitro 10 . Molecular mechanisms of cancer cell death are associated with structural characteristics of safrole derivates 11 . Transformation of side chain of safrole is a crucial step in achieving cancer prevention through induction of apoptosis and decreased proliferation of pre-malignant cells 11 .…”

Section: Introductionmentioning

confidence: 99%

“…Molecular mechanisms of cancer cell death are associated with structural characteristics of safrole derivates 11 . Transformation of side chain of safrole is a crucial step in achieving cancer prevention through induction of apoptosis and decreased proliferation of pre-malignant cells 11 . Such structural changes are directly related to free radical scavenging activity and the cytotoxic activity 12 .…”

Section: Introductionmentioning

confidence: 99%

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Antioxidant and Toxicity Activity in Vitro of Twelve Safrole Derivatives

Madrid

Espinoza

Pavéz

et al. 2014

J. Chil. Chem. Soc.

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The aim of this study was to determine the influence of substituents in aromatic ring and the side chain of safrole on the antioxidant capacity and toxicity of twelve synthetic derivatives of safrole (S1-S12). Each compound was analyzed by two antioxidant methods: DPPH and bleaching of β-carotene (DBC). Among the derivates of safrol assayed, S5, S6, S9, S10 and S11 showed the strongest antioxidant capacity: DPPH method, first order specific rate constant (0.0152, 0.0211, 0.0432, 0.0317 and 0.0072) and DBC (22.41 + 0.13%, 10.71 + 0.05 %, 9.12 + 0.89 %, 30.97 + 0.92 % and 19.08 + 0.31 %), respectively. The toxicity of the active compounds was evaluated by means of two techniques, Artemia salina, LD 50 (4466 ± 1057 ppm, 630 ± 108 ppm, 1513 ± 797 ppm, 1585 ± 317 ppm, 1259 ± 242 ppm) and red cells, Haemolysis (1.58 + 0.98%, 4.02 + 2.03%, 8.42 + 1.38%, 2.59+ 2.31%, 2.92 + 0.52%), to provide preliminary information that can be used as a basis for further studies to contribute to the search for new antioxidants.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antioxidant and Toxicity Activity in Vitro of Twelve Safrole Derivatives

Madrid

Espinoza

Pavéz

et al. 2014

J. Chil. Chem. Soc.

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“…Hydroboration of olefin can lead to terminal hydroxylation ( 15 ), whereas alkoxymercuration‐demercuration can be employed for internal hydroxylation ( 16 ) . Peracid‐mediated epoxidation yielded safrole epoxide ( 6 ), which upon ring opening followed by elimination produced hydroxylated isosafrole ( 17 ) . Aromatic electrophilic substitution occurred at C6, as evident from the formation of the 6‐nitro derivative ( 18 ) .…”

Section: Chemistry Of Safrolementioning

confidence: 99%

“…140,141 Peracid-mediated epoxidation yielded safrole epoxide (6), which upon ring opening followed by elimination produced hydroxylated isosafrole (17). 142 Aromatic electrophilic substitution occurred at C6, as evident from the formation of the 6-nitro derivative (18). 143 Safrole has also been used as the ligand for synthesizing cis-Pt complexes.…”

Section: Chemis Try Of Safrolementioning

confidence: 99%

Review on safrole: identity shift of the ‘candy shop’ aroma to a carcinogen and deforester

Kemprai

Mahanta

Sut

et al. 2019

Flavour & Fragrance J

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Safrole, a phenylpropene with a ‘candy shop’ aroma, is abundant in nature among diverse plant genera such as Sassafras, Ocotea, Cinnamomum, Myristica, and Piper. Sassafras oil has been used extensively for a long time, first by Native Americans and later by European settlers in traditional medicine and as a flavouring agent. Until 1960 the consumption of safrole by the western population, as a flavouring agent in beer, meat, and soft drinks, was unregulated. Later, the recognition of this phytochemical as a weak hepatocarcinogen with demonstrated genotoxicity in rodents led to strict restrictions on its use in food by various regulatory bodies globally. Moreover, in Asian countries oral carcinogenesis has been linked to safrole through the habit of chewing betel quid. As a separate issue, safrole is an inexpensive synthetic precursor to the illicit recreational drug Ecstasy. Accelerating demand for this party drug during the last few decades has encouraged the unscientific harvesting, illegal production, and trading of safrole‐rich oils, leading to massive deforestation. Recently, many government authorities have enforced laws to restrict the production and harvesting of safrole‐bearing plants. Thus, the identity of safrole has altered with time from a pleasant flavouring agent to a hepatocarcinogen, and more recently as a driver of the destruction of biodiversity. Law enforcement has not only hampered its availability but has also extensively affected industrial use. Our review describes the research progress (1960–2018) on its natural distribution, carcinogenicity, usage as a natural synthon, and the regulations imposed on safrole and safrole‐rich oils worldwide. Finally, we draw our readers’ attention to the sustainable use of this phytochemical for a better future.

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Collagen modified with epoxidized safrole for improving antibacterial activity

Chang

Zhang

et al. 2017

RSC Adv.

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An epoxidized safrole, 5-(oxiran-2-ylmethyl)-benzo [d] [1,3]dioxole (OYBD), was synthesized and employed to modify collagen for improving its antibacterial activity. The interaction between collagen and OYBD, and the structure/properties of the modified collagen were investigated in detail. The results indicated that the OYBD-modified collagen showed a higher de-nature temperature (Td, 90.2 C), improved hydrophobic properties (contact angle from 84.2 to 89.1 ) and enhanced tensile strength (6.2-11.0%) without destroying its triple helix structure. From observation of scanning electron microscopy (SEM), a higher density of intertwining morphology and a more stable network structure were observed, which was consistent with improved tensile strength and reduced breaking extension stress. The antibacterial test and LIVE/DEAD Baclight bacterial viability assay illustrated that the modified collagen exhibited excellent antibacterial activity to both Gram-negative and Grampositive bacteria. Furthermore, the OYBD-modified collagen still exhibited cytocompatibility, supporting human fibroblast proliferation, which holds a great potential for developing antibacterial collagen-based biomaterials.

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New Safrole Oxide Derivatives: Synthesis and in vitro Antiproliferative Activities on A549 Human Lung Cancer Cells

Cited by 4 publications

References 9 publications

Antioxidant and Toxicity Activity in Vitro of Twelve Safrole Derivatives

Antioxidant and Toxicity Activity in Vitro of Twelve Safrole Derivatives

Review on safrole: identity shift of the ‘candy shop’ aroma to a carcinogen and deforester

Collagen modified with epoxidized safrole for improving antibacterial activity

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