The paper titled "Role of Plant Carbonic Anhydrase-Like Enzymes in Neuroactive Alkaloid Biosynthesis" published in the journal Nature on November 8, 2023, by authors Ryan S. Nett, Yaereen Dho, Chun Tsai, among others, from the Department of Chemical Engineering at Stanford University, the Howard Hughes Medical Institute, and the Department of Molecular and Cellular Biology at Harvard University, etc. This study focuses on a class of plant carbonic anhydrase-like enzymes (CALs) that play a key role in the biosynthesis of neuroactive alkaloids in gymnosperms. Through in-depth analysis of the biosynthetic pathways in ferns, the research team revealed how these CAL proteins participate in the generation of neuroactive gymnosperm alkaloids, such as huperzine A, through a series of complex enzyme-catalyzed reactions. This work not only expands our understanding of plant-specific metabolic pathways but also provides a new perspective for the future discovery and development of plant alkaloid-based medications.
Four new phenolic glucosides, cannabifolins G–J (1–4), together with four known ones (5–8), were isolated from the leaves of Vitex negundo var. cannabifolia. Their structures were established by comprehensive analysis of 1D and 2D NMR data and comparison of their spectroscopic and physical data with the literature values. Compound 7 exhibited weak inhibition of nitric oxide production stimulated by lipopolysaccharide in BV‐2 microglial cells with IC50 value of 132.8 μM.
Five new iridoid glucosides, cannabifolisides A-E (1 - 5), together with nine analogues (6 - 14), were isolated from the leaves of Vitex negundo var. cannabifolia. Their structures were elucidated by spectroscopic data (NMR, UV, IR, and MS) analyses and comparison of their spectroscopic and physical data with the literature values. The protective effect of isolated compounds on human gastric epithelial cells were evaluated by measuring the enhanced cell viability of GES-1 cell insulted by TCA. Among these, compounds 4, 6, 8, 10, 12, and 14 remarkably increased the cell viability in a concentration-depend manner.
Two new furofuran lignan glucosides, cannabilignin (1) and isocannabilignin (2), together with four known compounds (3-6), were isolated from the leaves of Vitex negundo var. cannabifolia. The structures of the isolates were elucidated by analysis of spectroscopic data. Compound 3 exhibited weak inhibition of nitric oxide production in lipopolysaccharide-stimulated BV-2 microglial cells with IC50 value of 69.1 ± 5.8 μM.
This study was aimed to investigate the chemical constituents from the leaves of Vitex negundovar. cannabifolia. Column chromatography including silica gel, Sephadex LH-20, ODS, and semi-preparative HPLC were used to separate and purify the chemical constituents, and the structures were elucidated on the basis of physicochemical properties, MS and NMR spectroscopic data. As a result, 11 compounds were isolated from the ethyl acetate extract of V. negundo var. cannabifolia, and identified as apigenin (1), penduletin (2), chrysosplenol-D (3), quercetin (4), 1,4-dihydroxy-3R,5R-dicaffeoyloxy cyclohexane carboxylic acid (5), maeranthoin F (6), capsidiol (7), caryolandiol (8), β-sitosterol (9), p-hydroxybenzonic acid (10), and β-daucosterin (11). It was concluded that compounds 5 8were firstly isolated from the plants of Vitex genus, and compounds 1 and 4 were isolated from V. negundovar. cannabifolia for the first time.
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
目的 研究牡荆Vitex negundo var.cannabifolia叶中黄酮苷类化学成分.方法 采用硅胶、Sephadex LH-20和ODS等柱色谱技术,对牡荆叶的化学成分进行分离、纯化,通过其理化性质及MS、NMR等谱学数据鉴定化合物的结构.结果 从牡荆叶95%乙醇提取物的醋酸乙酯萃取部位分离得到7个黄酮苷类化合物,分别鉴定为木犀草素-4’-O-(6”-O-对羟基苯甲酰基)-β-D-葡萄糖苷(1)、木犀草素-7-O-(6”-O-对羟基苯甲酰基)-β-D-葡萄糖苷(2)、木犀草素-6-C-(6”-O-反式-咖啡酰基)-β-D-葡萄糖苷(3)、木犀草素-6-C-(2”-O-反式-咖啡酰基)-β-D-葡萄糖苷(4)、perfoliatuminA (5)、异牡荆素(6)、木犀草素-7-O-β-D-葡萄糖苷(7).结论 化合物1为新化合物,命名为牡荆宁G;化合物2~4、7为首次从该植物中分离得到,化合物5为首次从牡荆属植物中分离得到.
Ten new labdane diterpenoids, lagopsins A-H (1-3, 5, 7-10) and 15-epi-lagopsins C and D (4, 6), together with five known labdane diterpenoids (11-15), were isolated from the whole plants of Lagopsis supina. The absolute configuration of lagopsin A (1) was determined by single-crystal X-ray crystallographic analysis. Compounds 7, 9, 13, and 15 exhibited moderate inhibition of nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells with IC50 values in the range 14.9-34.9 μM.
Six new polyoxygenated triterpenoids, cannabifolins A-F (1-6), and eight known triterpenoids, 7-14, were isolated from the leaves of Vitex negundo var. cannabifolia. The absolute configuration of cannabifolin A (1) was determined by single-crystal X-ray crystallographic analysis. Compounds 1 and 2 represent a class of rare natural pentacyclic triterpenoids bearing cis-fused C/D rings and are the first examples of 12,19-epoxy ursane- and oleanane-type triterpenoids. Compounds 3, 7, 8, and 14 exhibited inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values in the range 24.9-40.5 μM.
Four new lignanamides, melongenamides A–D (1–4), together with six known ones (5–10), were isolated from the roots of Solanum melongena L. Their structures were elucidated on the basis of 1D and 2D NMR experiments and by comparison of their spectroscopic and physical data with the literature values. Compounds 2–8 exhibited inhibitions of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values ranging from 16.2 to 58.5μM.
Objective To study the phenolic constituents of Draconis Resina.Methods The compounds were isolated and purified by silica gel and sephadex LH-20 column chromatography,and their structures were identified by physiochemical properties and MS and NMR spectroscopic data.Results Fourteen compounds were isolated from the ethyl acetate extract of Draconis Resina and identified as 4′-hydroxy-1′,4″-dimethoxychalcane(1),7-hydroxy-5,4′-dimethoxy-2-arylbenzofuran(2),pterostilbene(3),3,4′-dihydroxy-5-methoxystilbene(4),5,7,4′-trihydroxyflavanone(5),pinocembrin(6),7-hydroxyflavanone(7),liquiritigenin(8),methyl 4-hydroxybenzoate(9),methyl 4-hydroxy-3-methoxybenzoate(10),ethyl 4-hydroxy-3-methoxybenzoate(11),2,4-dihydroxy acetophenone(12),3,4-dihydroxyallybenzene(13),and β-sitosterol(14).Conclusion Compound 1 is a new natural product.Compound 2 is firstly obtained from the plants of Liliaceae.Compounds 5 and 9—12 are firstly isolated from the plants of Dracaena Vand.ex L.,and compounds 6 and 7 are isolated from Dracaena cochinchinensis for the first time.
A quantitative HPLC-DAD method was developed for simultaneous determination of N-trans-p-coumaroyloctopamine and N-trans-p-coumaroyltyramine in Solani Melongenae Radix from different cultivation regions in China The separation was performed on an Agilent Eclipse XDB C18 column (4.6 mm x 250 mm, 5 microm) at 30 degrees C with a gradient elution of methanol and 0.1% formic acid in water as mobile phase. The flow rate was set at 1.0 mL x min(-1) and the detection wavelength was 300 nm. The calibration curves of N-trans-p-coumaroyloctopamine and N-trans-p-coumaroyltyramine were linear over the ranges of 2.84-68.16, 3.10-74.40 mg x L(-1), and the average recoveries (n = 9) were 99.30% and 102.8%, respectively. The developed method was successfully applied for the analysis of sixteen samples from different cultivation regions in China, which indicated that the method is simple, rapid, accurate, and reliable for quality evaluation of Solani Melongenae Radix.
The modern pharmacology study has proved that Lagopsis supine has definite pharmacological effects in improving blood and lymph microcirculation,myocardial protection,anti-inflammatory and antioxidant. The study has found that labdane diterpenoid com-pound isolated from Lagopsis supine such as marrubin has many biological activities,such as the relaxation of blood vessels,heart pro-tection and antispasmodic and analgesic,etc. . The biological activity has the same effect with Lagopsis supine in promoting blood circu-lation to remove blood stasis,and anti-inflammatory. So study on labdane diterpenoid compound and its biological activity in Lagopsis supine has great significance in clarifying material efficacy base of Lagopsis supine. It is necessary for deeply study on the chemical con-stituents and pharmacological activities,and clarify its material efficacy basis and mechanism of action,which will provide a scientific basis for its further development and utilization.
A quantitative HPLC-DAD method was developed for simultaneous determination of N-trans-p-coumaroyloctopamine and N-trans-p-coumaroyltyramine in Solani Melongenae Radix from different cultivation regions in China The separation was performed on an Agilent Eclipse XDB C18 column (4.6 mm x 250 mm, 5 microm) at 30 degrees C with a gradient elution of methanol and 0.1% formic acid in water as mobile phase. The flow rate was set at 1.0 mL x min(-1) and the detection wavelength was 300 nm. The calibration curves of N-trans-p-coumaroyloctopamine and N-trans-p-coumaroyltyramine were linear over the ranges of 2.84-68.16, 3.10-74.40 mg x L(-1), and the average recoveries (n = 9) were 99.30% and 102.8%, respectively. The developed method was successfully applied for the analysis of sixteen samples from different cultivation regions in China, which indicated that the method is simple, rapid, accurate, and reliable for quality evaluation of Solani Melongenae Radix.
茄是一种药食两用植物,富含咖啡酰奎宁酸酯衍生物、黄酮类、生物碱类、甾体皂苷类等多种化学成分,具有抗炎、镇痛、抗氧化、调血脂、降血糖和抗肿瘤等多种生物活性。综述了国内外对茄的化学成分及药理作用研究进展,并对茄的开发利用前景进行展望,为进一步合理开发和综合利用茄的药用资源提供有益参考。