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1.
Chem Biodivers ; 19(12): e202200490, 2022 Dec.
Article in English | MEDLINE | ID: mdl-36266258

ABSTRACT

2-(2-Phenylethyl)chromone derivatives are regarded as key components in agarwood. An oxygen-containing heterocycle with a benzoannelated γ-pyrone moiety form the bioactive core of 2-(2-phenylethyl)chromones. With different substituents and positions, 2-(2-phenylethyl)chromone derivatives exhibit diverse biological properties, such as antioxidant, antimicrobial, neuroprotective, anti-inflammatory, and acetylcholinesterase inhibitory activities. In this review, we summarized the studies (from January 1976 to September 2021) on phytochemistry, bioactivity and quality control of 2-(2-phenylethyl)chromones. These studies aimed to clarify the chemical specificity, diversity and structure-activity relationship of 2-(2-phenylethyl)chromones. In addition, we assumed that diverse factors such as tree species, induction methods and formation time contribute to the chemical diversity of 2-(2-phenylethyl)chromones. Furthermore, this review contends that different types of 2-(2-phenylethyl)chromones should be utilized in the quality control methods of agarwood.


Subject(s)
Chromones , Thymelaeaceae , Chromones/chemistry , Acetylcholinesterase , Thymelaeaceae/chemistry , Flavonoids/pharmacology , Flavonoids/chemistry , Molecular Structure
2.
J Ethnopharmacol ; 250: 112465, 2020 Mar 25.
Article in English | MEDLINE | ID: mdl-31821851

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: Curcumae Rhizoma and Sparganii Rhizoma (CR-SR) are the classical herbal couple for activating blood circulation and treating tumor in clinics. AIM OF THE STUDY: To investigate the anti-tumor activity and to clarify the bioactive ingredients of herbal couple CR-SR and the single herbs Curcumae Rhizoma (CR) and Sparganii Rhizoma (SR). MATERIALS AND METHODS: The active fractions of CR-SR decoction were fractioned by column chromatography. And isolated compounds were characterized by IR, ESI-MS, 1D and 2D-NMR techniques. Detecting linear-diarylheptanoids in CR-SR, CR and SR was realized through UPLC-LTQ-Orbitrap MSn, based on the fragmentation pathways established in this study, comparison with MS data of isolated compounds and references. The anti-tumor activities of different solvent fractions from CR-SR, CR and SR, as well as isolated ingredients were tested by CCK-8 method. RESULTS: Ultimately, a new compound (1), having a sulfonic acid group at C-3, named demethoxyshogasulfonic acid, along with another structurally similar 17 known linear-diarylheptanoids were isolated. These linear-diarylheptanoids (1-18) were divided into 12 categories based on the differences of substituents at C-3 and C-5 on the straight chain of seven carbons. Six fragmentation pathways were established by summarizing MS data of the 18 isolated compounds collected from UPLC-MS. Based on that, and retention times and MS fragmentation ions, 47 linear-diarylheptanoids were identified in CR-SR and CR, in which 12 linear-diarylheptanoids were also detected in SR. Most importantly, 5 sulfonated linear-diarylheptanoids were new compounds detected in CR and CR-SR. And the biological assay indicated that compounds 1-4 and 12-15 significantly reduced the proliferation and inhibited colony formation of MCF-7 and HepG2 cells. CONCLUSION: The new compound (1) exhibited good anti-cancer activity, which suggests that a great effort has to be paid to investigate the bioactivity of sulfonated compounds. The fractions of CR-SR decoction exhibited stronger anti-tumor activities than that of CR and SR against 5 different cancer cells. As for chemical composition, it is the first time to report that diarylheptanoids are in Sparganiaceae and the sulfonated compounds in Zingiberaceae. Moreover, the linear-diarylheptanoids found in SR which being tested to possess good anti-tumor activity, plus those compounds in CR enhance the capacity of CR-SR. It shows importance of TCM compatibility.


Subject(s)
Antineoplastic Agents/pharmacology , Curcuma , Diarylheptanoids/pharmacology , Plant Extracts/pharmacology , Rhizome , Typhaceae , Cell Line, Tumor , Humans
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