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In the search for novel compounds with both survivin inhibitory activity and fluorescence properties, 18 novel longifolene-derived tetralin pyrimidine compounds were designed using survivin as the target and synthesized from the sustainable natural resource longifolene. Their structures were confirmed by IR, NMR, ESIMS, and elemental analysis. The in vitro antiproliferative activities of the target compounds were preliminarily evaluated using the standard MTT assay against MGC-803 (human gastric cancer cell), T24 (human bladder cancer cell), HepG2 (human liver cancer cell), and A549 (human lung adenocarcinoma cell). As a result, some of the target compounds showed better antiproliferative activities than the positive control drug 5-FU, in which, compound 5m had an IC50 of 1.42 mM against MGC-803 and compound 5l had an IC50 of 1.79 mM against T24, exhibiting excellent activity. Additionally, the target compounds display moderate or even low cytotoxicity toward human normal liver cells L02. Subsequently, a reasonable and effective 3D-QSAR model was established to study the relationship between the structure of the target compounds and antiproliferative activities and was employed to construct two new compounds with potentially better activity. Meanwhile, molecular docking was performed to study the interaction mode between the compound 5m and survivin protein. Furthermore, the target compounds with significant antiproliferative activity showed noticeable fluorescence properties. [ABSTRACT FROM AUTHOR]

In the course of a phytochemical and chemotaxonomical investigation of Castanopsis species (Fagaceae), three new phenolic compounds, (3R,1′S)-[1′-(6″-O-galloyl-β-d-gluco-pyranosyl)oxyethyl]-3-hydroxy-dihydrofuran-2(3H)-one (1), (2R,3S)-2-[2′-(galloyl)oxyethyl]-dihydroxybutanoic acid (2), and (3S,4S)-3-hydroxymethyl-3,4-dihydro-5,6,7-trihydroxy-4-(4′-hydroxy-3′-methoxyphenyl)-1H-[2]-benzopyran-1-one (3) were isolated from the fresh leaves of Castanopsis fargesii. In addition, a known phenolic glycoside, gentisic acid 5-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (4) was also isolated and identified. Their structures were elucidated by means of spectroscopic methods including one- and two-dimensional NMR techniques. [ABSTRACT FROM AUTHOR]

In this study, four new lignan glucosides, named difengpiosides A–D (1–4), were isolated from the stem barks of Illicium difengpi, together with seven known compounds 5–11. Their structures were identified on the basis of spectroscopic analyses (1D and 2D NMR, HRESIMS, CD) and a comparison with literature data. All the compounds were evaluated for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells. [ABSTRACT FROM AUTHOR]

Siamenoside I is the sweetest mogroside that has several kinds of bioactivities, and it is also a constituent of Siraitiae Fructus, a fruit and herb in China. Hitherto the metabolism of siamenoside I in human or animals remains unclear. To reveal its metabolic pathways, a high-performance liquid chromatography-electrospray ionization-ion trap-time of flight-multistage mass spectrometry (HPLC-ESI-IT-TOF-MSn) method was used to profile and identify its metabolites in rats. Altogether, 86 new metabolites were identified or tentatively identified, and 23 of them were also new metabolites of mogrosides. In rats, siamenoside I was found to undergo deglycosylation, hydroxylation, dehydrogenation, deoxygenation, isomerization, and glycosylation reactions. Among them, deoxygenation, pentahydroxylation, and didehydrogenation were novel metabolic reactions of mogrosides. The distributions of siamenoside I and its 86 metabolites in rat organs were firstly reported, and they were mainly distributed to intestine, stomach, kidney, and brain. The most widely distributed metabolite was mogroside IIIE. In addition, eight metabolites were bioactive according to literature. These findings would help to understand the metabolism and effective forms of siamenoside I and other mogrosides in vivo. [ABSTRACT FROM AUTHOR]

Fordiae Cauliflorae Radix (FC, the root of Fordia cauliflora Hemsl) and Millettiae Pulchrae Radix [MP, the root of Millettia pulchra (Benth.) Kurz var. laxior (Dunn) Z. Wei], which go under the same local name of "Daluosan", have long been used in Southern China for the treatment of stroke, paralysis, dementia in children, Alzheimer's disease and other diseases. The same local name and similar functions always confuse users. To further utilize these two ethnodrugs and identify them unambiguously, an HPLC-DAD-ESI-IT-TOF-MSn method was developed to separate and characterize the flavonoids in FC and MP. A total of 41 flavonoids were detected, of which six compounds were identified by comparing their retention time and MS data with those of the reference standards, and the others were tentatively identified based on their tandem mass spectrometry data obtained in the positive ion detection mode. Nineteen of these characterized compounds are reported from these two plants for the first time. [ABSTRACT FROM AUTHOR]

Four new triterpenoid saponins, godosides A - D ( 1 - 4 ), along with eight known saponins, have been isolated from the fresh aerial parts of Ilex godajam . Structure elucidation of 1 - 4 was based on NMR, MS, IR and chemical analyses. [ABSTRACT FROM AUTHOR]