樟树叶化学成分的研究

本文研究了樟树叶的化学成分。主要采用硅胶、Sephadex LH-20凝胶和聚酰胺等柱层析方法对樟树叶的化学成分进行分离纯化,并根据理化性质、波谱数据(1H NMR,13C NMR)鉴定化合物的结构。从樟树叶的甲醇提取物中分离鉴定出9个化合物,分别为山柰酚-3-O-β-D-葡萄糖苷(1)、槲皮素-3-O-β-D-鼠李糖苷(2)、槲皮素-3-O-β-D-葡萄糖苷(3)、异鼠李素-3-O-β-D-葡萄糖苷(4)、黑色五味子单体苷(5)、山奈酚-3-O-β-D-芸香糖苷(6)、异鼠李素-3-O-β-D-芸香糖苷(7)、新芝麻脂素(8)和maculatin(9)。化合物1为首次从樟属中分离得到,化合物4、5、8为首次从樟科植物中分离得到。     

蒙古香蒲,宽叶香蒲和长苞香蒲花粉的黄酮类化合物的研究

蒙古香蒲(Typha davidiana Hand.-Mazz.)宽叶香蒲(Typha latifolia L.)和长苞香蒲(Typha angustata Bory et Chaub)的干燥花粉中分别分离得到柚皮素(Ⅰ),异鼠李素(Ⅱ),檞皮素(Ⅲ),异鼠李素-3-O-(2~G-α-L-鼠李糖基)-芸香糖甙(Ⅳ),檞皮素-3-O-(2~G-α-L-鼠李糖基)-芸香糖甙(Ⅴ),异鼠李素-3-O-芸香糖甙(Ⅵ),异鼠李素-3-O-新橙皮糖甙(Ⅶ)和山奈酚-3-O-新橙皮糖甙(Ⅷ)。     

重楼排草的化学成分研究

从报春花科植物重楼排草（L.Paridiformis Frach）的全株中分离得到了7个化合物。应用各种理化方法及光谱分析鉴定其化学结构。分别鉴定为：希克拉敏A-3-O-｜β-D-吡喃木糖基．（1→2）-β-D-吡喃葡萄糖基-（1→4）-[β-D-吡喃葡萄糖基-（1→2）]｜}-α-L-吡喃阿拉伯糖苷（1）、3β-O-[β-D-吡喃木糖基-（1→2）-β-D-吡喃葡萄糖基-（1→4）]。[β-D-吡喃葡萄糖基-（1→2）]-α-L-吡喃阿拉伯糖基-16α-羟基-13β,28-环氧-齐墩果烷（2）、异鼠李素-3-O-[β-D-吡喃鼠李糖基-（1→）β-D-吡喃阿拉伯糖苷]（3）、槲皮素-3-O-[β-D-吡喃鼠李基-（1→4）-β-D-吡喃阿拉伯糖苷]（4）、β-香树素（5）、β-香树素乙酸酯（6）、三十二烷醇（7）。其中1、2、3、4均为首次从本植物中分离得到。     

布渣叶中三萜和黄酮类成分的研究

从布渣叶(Microcos paniculata L.)的叶中分离得到10个化合物.通过光谱和波谱分析,分别鉴定为无羁萜(1)、阿江榄仁树葡糖苷Ⅱ(2)、山柰酚-3-O-β-D-[3,6-二(对羟基桂皮酰)]-葡萄糖苷(3)、山柰酚-3-O-β-D-葡萄糖苷(4)、异鼠李素3-O-β-D-葡萄糖苷(5)、异鼠李素3-O-β-D-芸香糖苷(6)、牡荆苷(7)、佛来心苷(8)、异佛来心苷(9)、异牡荆苷(10).10个化合物均为首次从布渣叶中分离得到.     

唐古特白刺黄酮类化合物的研究

唐古特白刺(Nitraria tangutorum Boler)系蒺藜科白刺属植物,民间用于治疗脾胃虚弱,消化不良,神经衰弱,感冒等症,其化学成分研究尚未见文献报道。本文报道从唐古特白刺种子中分得6个黄酮类化合物:异鼠李素-7-O-α-L-鼠李糖甙、山奈素-7-O-α-L-鼠李糖甙、异鼠李素-7-O-β-D-葡萄糖甙、槲皮素-7-O-α-L-鼠李糖甙、异鼠李糖、槲皮素。前4个化合物首次从该属植物中分得,它们的存在对我国白刺属植物分类将有一定意义。     

芍药黄色花瓣中黄酮醇及其糖苷类化合物组成分析

本研究以3个托桂型芍药品种为研究对象,利用高效液相色谱-光电二极管阵列检测(HPLC-DAD)和高效液相色谱-电喷雾离子化-二级质谱联用技术(HPLC-ESI-MS2)鉴定黄色内瓣中黄酮醇及其糖苷类化合物组成,并对其峰面积进行分析。共鉴定出11种黄酮醇及其糖苷类化合物(槲皮素-3,7-O-二葡萄糖苷、山奈酚-3,7-O-二葡萄糖苷、异鼠李素-3,7-O-二葡萄糖苷、槲皮素-3-O-葡萄糖苷-6″-没食子酸酯、槲皮素-3-O-没食子酰葡萄糖苷、山奈酚-3-O-葡萄糖苷-7-O-鼠李糖苷、槲皮素-3-O-β-D-葡萄糖苷、山奈酚-3-O-葡萄糖苷-6″-没食子酸酯、山奈酚-3-O-β-D-葡萄糖苷、异鼠李素-3-O-β-D-葡萄糖苷和山奈酚)。其中,10种成分在3个品种中均被检测出,只有槲皮素-3-O-没食子酰葡萄糖苷在‘向阳奇花’中未检测到,除了山奈酚-3-O-葡萄糖苷-7-O-鼠李糖苷以外,其他成分的峰面积在3个品种黄色内瓣中的差异性较大。本研究为托桂型芍药品种中黄色内瓣的形成机理提供一定的理论依据和黄酮类物质的进一步开发利用等研究奠定基础。     

香樟叶化学成分的研究

采用硅胶色谱柱层析、聚酰胺色谱柱层析、制备薄层色谱及其它分离手段从香樟叶(Cinnamomum camphora Leaves)70%乙醇提取中分离得到9个化合物,根据化合物理化性质和波谱数据分别鉴定为:邻苯二甲酸二丁酯(1)、l-细辛脂素(2)、(8R,8'R)-3,3',4,4'-四甲氧基-9-氧代-8-8',9-O-9'-木脂素(3)、槲皮素-3-Ο-β-D-葡萄糖苷(4)、山奈酚-3-O-β-芸香糖苷(5)、山柰酚-3-O-α-L-吡喃鼠李糖苷(6)、槲皮素3-Ο-α-L-鼠李糖苷(7)、芦丁(8)、异鼠李素-3-O-β-芸香糖苷(9)。其中化合物1,2,6和9为首次从该种植物叶中分离得到。     

新疆千里光的化学成分研究北大核心CSCD

本文对新疆千里光进行了化学成分研究,从中分离鉴定了12个化合物,分别为千里光碱（1）、千里光菲灵碱（2）、全缘千里光碱（3）、克式千里光碱（4）、异鼠李素（5）、槲皮素（6）、异鼠李素-3—O-β-D-半乳糖苷（7）、8-（2＂-pyrrolidinone-5”-y1）-isorhamnetin（8）、pseudotaraxasterc1（9）、咖啡酸（10）、β-谷甾醇（11）、卢-胡萝卜苷（12）。除1—3外,其余9个化合物均为首次从该植物中分离得到。     

见血封喉树叶化学成分研究

从见血封喉(Antiaris toxicaria(Pers.)Lesch.)树叶中分离得到了6个化合物,经波谱数据分析,分别鉴定其结构为:(3S,5R,6S,7E,9R)-3,6-dihydroxy-5,6-dihydro-β-ionol(1)、(5R)-4,5-二氢布卢门醇A(2)、槲皮素-3-O-β-D-葡萄糖苷(3)、异鼠李素-3-O-β-D-芸香糖苷(4)、山柰甲黄素-3-O-β-D-葡萄糖苷(5)和环氧松柏醇(6),以上化合物均为首次从该种植物中分离得到.     

枸骨叶的化学成分研究

采用溶剂提取和柱层析色谱分离,根据化合物理化性质和光谱数据鉴定其结构.结果从枸骨叶中分离得到9个化合物,分别为羽扇豆醇(1)、3,28-乌苏酸二醇(2)、熊果酸(3)、异鼠李黄素(4)、山奈酚-3-O-β-D-葡萄糖苷(5)、地榆苷Ⅰ(6)、槲皮苷-3-O-β-D-葡萄糖苷(7)、异鼠李素-3-O-β-D-葡萄糖苷(8)、冬青苷Ⅱ(9).化合物7和8为首次从冬青属植物中分离得到,化合物5为首次从该植物中分离得到,同时首次报道了化合物9的13CNMR数据.     

藏药红花绿绒蒿的化学成分

从红花绿绒蒿(Meconopsis punicea)植物地上部分中分离得到17个化合物,通过MS和NMR等方法将它们的结构分别鉴定为karachine(1)、valachine(2)、二氢血根碱(dihydrosanguinarine,3)、威尔士绿绒蒿定碱((?)-mecambridine,4)、原鸦片碱(protopine,5)、马齿苋酰胺E(oleracein E,6)、anhydroberberillic acid(7)、小糪碱(berberine,8)、阿苞碱(alborine,9)、木犀草素(luteolin,10)、小麦黄素(tricin,11)、二氢槲皮素(dihydroquerce-tin,12)、洋芹素(apigenin,13)、大风子素(hydnocarpin,14)、小麦黄素7-O-β-D-葡萄糖苷(tricin 7-O-β-D-glucopyr-anoside,15)、对羟基桂皮酸(p-coumaric acid,16)和尿嘧啶(uracil,17)。其中,化合物1~3、7、15和17为首次从该属植物中分离得到;6、8、11和14为首次从该种植物中分离得到,采用二维NMR技术首次归属了化合物1和2的1H和13C NMR信号。     

大头艾纳香化学成分的研究

利用硅胶柱色谱、Sephadex LH-20柱色谱等手段从大头艾纳香(Blumea megacephala(Randeria)Chang etTseng)全草中分离得到13个化合物,根据化合物的理化性质和光谱数据分别鉴定为无羁萜(1)、小麦黄素(2)、豆甾醇二十六烷酸酯(3)、豆甾醇十八烷酸酯(4)、α-香树脂醇(5)、α-香树脂醇乙酸酯(6)、β-香树脂醇乙酸酯(7)、β-谷甾醇(8)、豆甾醇(9)、β-胡萝卜苷(10)、二十七烷醇(11)、十六烷酸(12)和二十四烷酸(13)。所有化合物均为首次从大头艾纳香中分离得到。     

Cardiovascular protective flavonolignans and flavonoids from Calamus quiquesetinervius

Tricin-type flavonolignans, (2S)-dihydrotricin 4′-O-(erythro-β-guaiacylglyceryl) ether, (2S)-dihydrotricin 4′-O-(threo-β-guaiacylglyceryl) ether, (2S)-dihydrotricin 4′-O-(threo-β-4-hydroxyphenylglyceryl) ether, tricin 4′-O-(erythro-β-4-hydroxyphenylglyceryl) ether, tricin 4′-O-(threo-β-4-hydroxylphenylglyceryl) ether, and (2S)-dihydrotricin 4′-O-(β-6′′-methoxy-4′′-oxo-chroman-3′′-yloxy) ether namely calquiquelignan A–F, respectively, were isolated and characterized from the EtOAc extract of Calamus quiquesetinervius. Additionally, six known phenolic compounds, including dihydrotricin, tricin, salcolin A, p-hydroxybenzoic acid, (2S, 3S)-trans-dihydrokapempferol and (2S)-naringenin, were also obtained and identified from the extract. Structures of the flavonolignans were assigned based on spectroscopic analyses that included 1D and 2D NMR spectroscopic techniques, such as HMQC, HMBC, and NOESY. Bioassay results showed that calquiquelignan A, dihydrotricin and (2S)-naringenin exhibited significant vasodilatory potencies, as indicated by 60.3%, 80.3% and 60.9% relaxations, respectively, at 100 μM. Salcolin A showed potent platelet aggregation inhibition, compared with aspirin. Most of the tricin-type derivatives (calquiquelignan A–B, dihydrotricin and tricin) also exhibited more potent hydroxyl radical (OH) scavenging activity than trolox as characterized by the ultraweak chemiluminescence assay.     

Tricin‐lignins: occurrence and quantitation of tricin in relation to phylogeny

Tricin [5,7‐dihydroxy‐2‐(4‐hydroxy‐3,5‐dimethoxyphenyl)‐4H‐chromen‐4‐one], a flavone, was recently established as an authentic monomer in grass lignification that likely functions as a nucleation site. It is linked onto lignin as an aryl alkyl ether by radical coupling with monolignols or their acylated analogs. However, the level of tricin that incorporates into lignin remains unclear. Herein, three lignin characterization methods: acidolysis; thioacidolysis; and derivatization followed by reductive cleavage; were applied to quantitatively assess the amount of lignin‐integrated tricin. Their efficiencies at cleaving the tricin‐(4′–O–β)‐ether bonds and the degradation of tricin under the corresponding reaction conditions were evaluated. A hexadeuterated tricin analog was synthesized as an internal standard for accurate quantitation purposes. Thioacidolysis proved to be the most efficient method, liberating more than 91% of the tricin with little degradation. A survey of different seed‐plant species for the occurrence and content of tricin showed that it is widely distributed in the lignin from species in the family Poaceae (order Poales). Tricin occurs at low levels in some commelinid monocotyledon families outside the Poaceae, such as the Arecaceae (the palms, order Arecales) and Bromeliaceae (Poales), and the non‐commelinid monocotyledon family Orchidaceae (Orchidales). One eudicotyledon was found to have tricin (Medicago sativa, Fabaceae). The content of lignin‐integrated tricin is much higher than the extractable tricin level in all cases. Lignins, including waste lignin streams from biomass processing, could therefore provide a large and alternative source of this valuable flavone, reducing the costs, and encouraging studies into its application beyond its current roles.     

Flavone glucosides with immunomodulatory activity from the leaves of Pleioblastus amarus

Three flavone glucosides, pleiosides A-C, were isolated from the leaves of Pleioblastus amarus, along with two known flavones: tricin and tricetin 3,5-dimethoxy-7-O-β-d-glucopyranoside. Their structures were elucidated by extensive spectral studies. Pleiosides A-C were found to inhibit the proliferation of murine T and significantly stimulate the proliferation of murine B lymphocytes in vitro.     

Antileishmanial Activity and Immunomodulatory Effects of Tricin Isolated from Leaves of Casearia arborea (Salicaceae)

Bioactivity‐guided fractionation of antileishmanial active extract from leaves of Casearia arborea led to isolation of three metabolites: tricin ( 1 ), 1′,6′‐di‐O‐β‐d ‐vanilloyl glucopyranoside ( 2 ) and vanillic acid ( 3 ). Compound 1 demonstrated the highest activity against the intracellular amastigotes of Leishmania infantum, with an IC₅₀ value of 56 μm . Tricin ( 1 ) demonstrated selectivity in mammalian cells (SI > 7) and elicited immunomodulatory effect on host cells. The present work suggests that tricin modulated the respiratory burst of macrophages to a leishmanicidal state, contributing to the parasite elimination. Therefore, the natural compound tricin could be further explored in drug design studies for leishmaniasis treatment.     

Natural flavone tricin exerted anti-inflammatory activity in macrophage via NF-κB pathway and ameliorated acute colitis in mice

BackgroundUlcerative colitis is a subtype of inflammatory bowel disease, characterized by relapsing inflammation in the gastrointestinal tract with limited treatment options. Previous studies suggested that the natural compound tricin, a flavone isolated from rice bran, could suppress chemically-induced colitis in mice, while our recent study also demonstrated the anti-metastatic effect of tricin in colon tumor-bearing mice.Hypothesis/PurposeHere we further investigated the underlying mechanism of the inhibitory effects of tricin on lipopolysaccharides-activated macrophage RAW264.7 cells and explored the efficacy of tricin in acute colitis mouse model induced by 4.5% dextran sulfate sodium (DSS) for 7 days.MethodsTricin (75, 100, and 150 mg/kg) or the positive control drug sulfasalazine (200 mg/kg) were orally administered to mice for 7 days. Stool consistency scores, stool blood scores, and body weight were recorded daily. Disease activity index (DAI) was examined on day 7, and colon tissues were collected for biochemical analyses. The fecal microbiome of colitis mice after tricin treatment was characterized for the first time in this study using 16S rDNA amplicon sequencing.ResultsResults showed that tricin (50 µM) remarkably reduced nitric oxide production in lipopolysaccharides-activated RAW264.7 cells and the anti-inflammatory activity of tricin was shown to act through the NF-κB pathway. Besides, tricin treatment at 150 mg/kg significantly reversed colon length reduction, reduced myeloperoxidase activities and DAI scores, as well as restored the elevated myeloid-derived suppressive cells population in acute colitis mice. The influence from DSS on gut microbiota, such as the increased population of Proteobacteria phylum and Ruminococcaceae family, was shown to be relieved after tricin treatment.ConclusionOur present study firstly demonstrated that tricin ameliorated acute colitis by improving colonic inflammation and modulating gut microbiota profile, which supports the potential therapeutic use of tricin for colitis treatment.     

Potential resistance of tricin in rice against brown planthopper Nilaparvata lugens (Stål)

The aerial parts of resistant rice plant (IR36) was immersed in 85% ethanol at room temperature, and ethanol-soluble extracts were prepared. Different solvents including petroleum ether, ethyl acetate, absolute ethanol, and water were then used to separate the ethanol-soluble extracts and different solvent fractions were obtained. These fractions were tested for their effects on the mortality rate of the brown planthopper nymphae (BPH). The results indicated that EtOAc fractions had significant effects on the mortality of brown planthopper nymphae after the third day of treatment. EtOAc fractions of resistant rice plants (IR36) were separated using column chromatography over silica gel and 5,7,4′ -trihydroxy-3′,5′-dimethoxyflavone (tricin) was isolated. After the BPH were allowed to feed on diets containing tricin for 15 days, it was found that the weight of honeydew of the nymphae showed a decrease as tricin concentrations in the diets increased. The mortality rate of the nymphae increased with increasing tricin concentration. The corrected mortality rate was 58.21% for the 3rd instar nymphae and 31.75% for the 4th instar nymphae, respectively, at 500 μg/ml concentration. In addition, tricin (500 μg/ml) significantly inhibited oviposition behavior and feeding of the brown planthopper females in choice tests when spread on susceptible rice plant (TN1).     

Antiproliferative and antioxidant activities of a tricin acylated glycoside from sugarcane (Saccharum officinarum) juice

From sugarcane juice, a flavone, identified by spectroscopic methods as tricin-7-O-β-(6″-methoxycinnamic)-glucoside, was isolated, in addition to orientin. The tricin derivative was shown to have antioxidant activity higher than Trolox^® by means of the DPPH assay and lower by the β-carotene/linoleic acid system. It showed in vitro antiproliferative activity against several human cancer cell lines, with higher selectivity toward cells of the breast resistant NIC/ADR line.     

P-glycoprotein inhibitory activity of two phenolic compounds, (-)-syringaresinol and tricin from Sasa borealis

(-)-Syringaresinol and tricin, isolated from the AcOEt-soluble extract of the whole plants of Sasa borealis (Gramineae), showed inhibitory effects on the P-glycoprotein in adriamycin-resistant human breast cancer cells, MCF-7/ADR.