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Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus.

ABSTRACT: Callisalignenes G-I (1-3), three new meroterpenoids of β-triketone and monoterpene, along with two known analogues (4 and 5), were isolated from Callistemon salignus. Their structures and absolute configurations were unambiguously established by a combination of NMR and MS analysis and electronic circular dichroism (ECD) evidence. Callisalignenes H (2) and I (3) have a rare sec-butyl moiety at C-7. Meroterpenoids 1-3 exhibited cytotoxicity against HCT116 cells with IC₅₀ values of 8.51 ± 1.8, 9.12 ± 0.3, and 16.33 ± 3.3 μM, respectively. Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus.

SUBMITTER: Qin XJ

PROVIDER: S-EPMC5507812 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus.

Qin Xu-Jie XJ Shu Tong T Yu Qian Q Yan Huan H Ni Wei W An Lin-Kun LK Li Pan-Pan PP Zhi Yin-E YE Khan Afsar A Liu Hai-Yang HY

Natural products and bioprospecting 20170615 4

Callisalignenes G-I (1-3), three new meroterpenoids of β-triketone and monoterpene, along with two known analogues (4 and 5), were isolated from Callistemon salignus. Their structures and absolute configurations were unambiguously established by a combination of NMR and MS analysis and electronic circular dichroism (ECD) evidence. Callisalignenes H (2) and I (3) have a rare sec-butyl moiety at C-7. Meroterpenoids 1-3 exhibited cytotoxicity against HCT116 cells with IC<sub>50</sub> values of 8.51 ...[more]

PMID: 28620873

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Project description:Platelets are an important component of the initial response to vascular endothelial injury; however, platelet dysfunction induces the acute clinical symptoms of thrombotic disorders, which trigger severe cardiovascular diseases such as myocardial infarction, ischemia, and stroke. In this study, we investigated the Dryopteris crassirhizoma's antiplatelet activity. A water extract of D.crassirhizoma (WDC) was partitioned into dichloromethane (DCM), ethyl acetate, n-butyl alcohol, and water. Among these four fractions, the DCM fraction potently inhibited the collagen-stimulated platelet aggregation in a concentration-dependent manner. From this fraction, five different acylphloroglucinol compounds and one flavonoid were isolated by activity-guided column chromatography. They were identified by comparing their mass, 1H-, and 13C-NMR spectral data with those reported in the literature. Quantifying the six compounds in WDC and its DCM fraction by high-performance liquid chromatography (HPLC) revealed that butyryl-3-methylphloroglucinol (compound 4) was the most abundant in these samples. Additionally, butyryl-3-methylphloroglucinol showed the strongest inhibitory activity in the collagen- and arachidonic acid (AA)-induced platelet aggregation, with inhibition ratios of 92.36% and 89.51% in the collagen and AA-induced platelet aggregation, respectively, without cytotoxicity. On the active concentrations, butyryl-3-methylphloroglucinol significantly suppressed the convulxin-induced platelet activation. Regarding the structure-activity relationships for the five acylphloroglucinol compounds, our results demonstrated that the functional butanonyl, methoxy, and hydroxy groups in butyryl-3-methylphloroglucinol play important roles in antiplatelet activity. The findings indicate that acylphloroglucinols, including butyryl-3-methylphloroglucinol from D.crassirhizom, possess an antiplatelet activity, supporting the use of this species for antiplatelet remedies.

Dataset Information

Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus.

Publications

Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus.

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