Structure-activity relationships of bergenin derivatives effect on α-glucosidase inhibition

The α-glucosidase inhibitory activities of bergenin derivatives were evaluated. Bergenin derivatives were synthesized from bergenin which is a characteristic compound of B. ligulata. A new bergenin derivative, 11-O-(3′,4′-dimethoxybenzoyl)-bergenin showed the highest potent inhibitory activity among those of bergenin derivatives. The presence of substituents at 3′,4′-position in bergenin derivatives altered the α-glucosidase inhibitory activity. 11-O-(3′,4′-dimethoxybenzoyl)-bergenin was noncompetitive inhibitor for α-glucosidase. The present study reveals that bergenin derivatives could be classified as a new group of α-glucosidase inhibitors.     

藏药黑蕊虎耳草的化学成分

从黑蕊虎耳草(Saxifraga melanocentra)地上部分的乙醇提取物中分离得到10个化合物,通过波谱分析并与有关对照品比较,将其结构鉴定为山奈酚(1),槲皮素(2),山奈酚-3-O-β-D-葡萄糖苷(黄芪苷)(3),槲皮素-3-O-β-D-葡萄糖苷(4),山奈酚-3-O-芦丁糖苷(5),芦丁(6),2″-O-没食子酰芦丁(7),岩白菜素(8),没食子酸(9)和没食子酸甲酯(10),除化合物2、6、8和10外,其余6个化合物均为首次从虎耳草属植物中得到。这些成分的鉴定为该植物的药效学研究提供了新的化学依据。     

Cancer Chemopreventive Effect of Bergenin from Peltophorum pterocarpum Wood

The aqueous extract of Peltophorum pterocarpum (Fabaceae) wood exhibited potent inhibitory effects against Epstein? Barr virus early antigen (EBV‐EA) activation induced with 12‐O‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cells and against melanogenesis in α‐melanocyte‐stimulating hormone (α‐MSH)‐stimulated B16 melanoma cells, as well as potent 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) free radical‐scavenging activity. Two phenolic acid derivatives, bergenin ( 1 ) and gallic acid ( 2 ), were isolated from the ethyl acetate (AcOEt)‐soluble fraction obtained from the extract. Compound 1 exhibited potent inhibitory effect against EBV‐EA activation and against skin tumor promotion in an in vivo two‐stage mouse skin carcinogenesis test based on 7,12‐dimethylbenz[a]anthracene (DMBA) as initiator, and with TPA as promoter. Both compounds 1 and 2 exhibited melanogenesis‐inhibitory activities in α‐MSH‐stimulated B16 melanoma cells, and, in addition, compound 2 showed strong DPPH radical‐scavenging activity.     

朱砂根愈伤组织诱导及其岩白菜素含量的测定

取朱砂根(Ardisia crenota Sims．)幼苗不同部位作外植体,研究不同激素组合对愈伤组织诱导的影响,利用薄层层析(TLC)和高效液相色谱(HPLC)检测愈伤组织中岩白菜素含量。实验结果表明朱砂根幼苗的不同部位(胚根、下胚轴、茎及叶)均能诱导出愈伤组织,最高诱导率都在45％以上,以MS基本培养基添加2,4—D0．5mg L^-1和KT0．01mg L^-1时愈伤组织的诱导和生长最好。这些愈伤组织均有合成岩白菜素的能力,其中以胚根诱导的愈伤组织中岩白菜素含量最高,为干重的0．076％,相当于原植物根中含量的1／9。高效液相色谱定量测定法精密度高,专一性好,能准确检测朱砂根愈伤组织中岩白菜素的含量。     

Synthesis,antioxidant capacity,and structure–activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition

A series of tri-O-methylnorbergenin analogues 1–9 were synthesized and their antioxidant activities and inhibitory effects on tyrosinase were evaluated. Among tested analogues, compound 4 bearing cathechol moiety exhibited greater antioxidant activity and excellent inhibition on tyrosinase with IC₅₀ value of 9.1 μM, comparable to that of corresponding positive controls. The inhibition mechanism analysis of compound 4 demonstrated that it was a mixed-type inhibitor on tyrosinase. These results suggest that these compounds may serve as a useful clue for further designing and development of novel potential tyrosinase inhibitors.     

Synthesis and biological evaluation of bergenin-1,2,3-triazole hybrids as novel class of anti-mitotic agents

In continuation of our investigation of pharmacologically-motivated natural products, we have isolated bergenin (1) as a major compound from Mallotus philippensis, which is deployed in different Indian traditional systems of medicine. Here, a series of bergenin-1,2,3-triazole hybrids were synthesized and evaluated for their potentials against a panel of cancer cell lines. Several of the hybrid derivatives were found more potent in comparison to parent compound bergenin (1). Among them, 4j demonstrated potent activity against A-549 and HeLa cell lines with IC₅₀ values of 1.86 µM and 1.33 μM, respectively, and was equipotent to doxorubicin. Cell cycle analysis showed that 4j arrested HeLa cells at G2/M phase and lead to accumulation of Cyclin B1 protein. Cell based tubulin polymerization assays and docking studies demonstrated that 4j disrupts tubulin assembly by occupying colchicine binding pocket of tubulin.     

不同产地不同部位壮药大罗伞树定性和定量分析

该研究采用TLC方法,对不同产地大罗伞树进行定性鉴别,并采用HPLC方法对大罗伞树不同产地和不同部位的岩白菜素进行了含量测定。其中,色谱柱为Sino Chrom ODS-BP C18(250 mm×4.6,5μm),流动相为甲醇-水(23∶77),流速为1.0 m L·min~(-1),检测波长为275 nm。结果表明:10批不同产地大罗伞树药材的TLC均可检出岩白菜素斑点;10批不同产地大罗伞树药材中岩白菜素平均含量为1.67%,但产地间含量差异较大,最高含量可达2.58%,最低含量0.95%;大罗伞树不同部位中岩白菜素含量有所差异,地下部分(根及根茎)含量较高,平均值为4.05%,地上部分(茎枝和叶)含量较低,平均值为1.21%。所建立的大罗伞树药材TLC鉴别和岩白菜素含量测定方法操作简便、专属性强、重现性好、结果准确。该研究结果能准确鉴别大罗伞树药材真伪,并测定药材中岩白菜素的含量,为大罗伞树药材质量标准的建立提供了依据,对于控制壮药大罗伞树药材质量具有重要意义。     

Synthesis and antiglycation potentials of bergenin derivatives

Bergenin (1), major bioactive compound isolated from methanolic extract of Mallotus philippinensis, displayed moderate AGE inhibition activity (IC₅₀ = 186.73 μM). A series of derivatives of bergenin (3a-k) containing variety of aromatic acids were synthesized under mild conditions by modification of sugar part. Selective esterification of hydroxyl groups on the sugar part enhanced antiglycation potential of bergenin. Compounds 3j and 3k exhibited potent antiglycation activity with the IC₅₀ values of 60.75 and 12.28 μM, respectively.     

Bergenin glycosides from Rodgersia aesculifolia

Phytochemical investigation on Rodgersia aesculifolia afforded twenty-three compounds, including three bergenin glycosides, previously unknown in nature, together with twenty known compounds. Their structures were elucidated by the extensive use of 1D and 2D NMR experiments, along with IR and HRESIMS spectra. This is the first report of bergenin glycosides from nature.