QTL mapping of foliar glycoalkaloid aglycones in Solanum tuberosum×S. berthaultii potato progenies: quantitative variation and plant secondary metabolism

 Glycoalkaloids are quantitatively inherited in Solanum, and in high concentrations they can be toxic to humans. The increased use of wild potato germplasm to improve the pest resistance, yield, and quality characteristics of cultivated potato may elevate or introduce new, more toxic glycoalkaloids into the cultivated gene pool. Therefore, it is important to increase our understanding of their inheritance, accumulation, and biosynthesis. Glycoalkaloids have two basic constituents – a glycosidic grouping and a steroid alkaloid skeleton. Steroid alkaloids are classified as solanidanes and spirosolanes, of which solanidine and solasodine are, respectively, representatives. RFLP-mapped, diploid, reciprocal backcross potato progenies involving the parents S. tuberosum and S. berthaultii, which produce solanidine and solasodine, respectively, were analyzed for segregation of the glycoalkaloids solanine, chaconine, solasodine and solamargine to identify quantitative trait loci (QTLs) for the production of the aglycones solanidine and solasodine. The F₁ clone M200-30 exhibited low to nondetectable levels of solasodine and solanidine, suggesting that expression was controlled by recessive genes. In a backcross to berthaultii (BCB) and backcross to tuberosum (BCT), several QTLs for the accumulation of solasodine and solanidine were identified. Three QTLs explaining approximately 20% of the variation in solasodine were identified in BCB on chromosomes 4, 6, and 12. Similarly, three QTLs were identified in BCT on chromosomes 4, 8 and 11, but these accounted for only 10% of the variation observed in solasodine accumulation. Two QTLs for solanidine were identified in BCT on chromosomes 1 and 4. The QTL located on chromosome 1 was highly significant, accounting for 17% and 22% of the variation in solanidine accumulation in 1994 and 1995, respectively. This same QTL was also detected in BCB. The QTLs detected in this study probably represent structural and/or regulatory genes controlling the accumulation of solasodine and solanidine. Results are discussed in the context of steroid alkaloid accumulation and biosynthesis. Received: 27 August 1997 / Accepted: 16 March 1998     

New insight into the stereoselective interactions of quinine and quinidine,with bovine serum albumin

Quinine (QN) and quinidine (QD), the chief quinoline alkaloids of various species of cinchona bark, are stereoisomers to each other. In this study, a series of appropriate and efficient methods have been applied to compare the binding modes of QN and QD with bovine serum albumin (BSA). The isothermal titration calorimetry and room temperature phosphorescence results show that both QN and QD can interact with BSA at one binding site to form drug–protein complexes, mainly through enthalpic driving force with the binding affinity order: QN > QD. The fluorescence resonance energy transfer and time‐resolved fluorescence spectroscopy exhibits that QN has a larger energy transfer and more intensified binding capacity for BSA than QD. Data of dynamic light scattering reveal that the aggregate state of BSA is changed during this binding process, and the particle size distribution of QN‐BSA bioconjugate is larger than that of QD. Nuclear magnetic resonance analysis indicates that aromatic protons make more contribution during ligand‐protein complexation than that of aliphatic protons. The circular dichroism spectra exhibit different degrees of changes in BSA secondary structures in the presence of QN and QD, respectively. Copyright © 2014 John Wiley & Sons, Ltd.     

Asymmetric synthesis of phenanthroindolizidine alkaloids with hydroxyl group at the C14 position and evaluation of their antitumor activities

The asymmetric total synthesis of the strongly cytotoxic phenanthroindolizidine alkaloid 3 was achieved. Using the same route, various derivatives were also synthesized. Cytotoxicity of those synthetic compounds was evaluated and compounds 19, 23, and 27 demonstrated potent cytotoxicities similar to that of 3. The in vivo antitumor efficacy of selected compounds was also evaluated and 23 demonstrated moderate antitumor efficacy.     

Hybridisation in Jacobaea – characterisation of hybrids between Jacobaea aquatica and J. vulgaris in Austria

Background: Hybridisation in Senecio/Jacobaea is frequent and of significance in speciation and evolution. Moreover, these genera are model systems for studying the evolution of pyrrolizidine alkaloids (PAs). Hybrids between Jacobaea aquatica and J. vulgaris have been reported from north-western Europe.

Aims: Our aim was to determine whether hybrids between Jacobaea aquatica and J. vulgaris also occurred in Austria, and if these hybrids could be responsible for the presumed increase of J. aquatica-like plants in this part of Europe. Furthermore, we tested if such hybrids showed an altered PA spectrum compared with parental species.

Methods: We used amplified fragment length polymorphisms (AFLPs) to analyse genetic diversity and structure, and gas chromatography–mass spectrometry (GC–MS) to identify PAs.

Results: We were able to identify genetically one hybrid population adjacent to a large J. aquatica population. The AFLP phenotypes of hybrids demonstrated a closer relationship to J. aquatica, suggesting frequent backcrossing. All hybrid individuals contained the same set of PAs as the parental species, but in differing amounts, plus four additional PAs, one of which may be novel.

Conclusions: Although hybridisation in Jacobaea is common, we were able to confirm only one hybrid population in Austria. Therefore, it seems unlikely that hybridisation plays a role in the presumed increase of J. aquatica in this area.     

正交设计优化微波辅助测定延胡索叶总生物碱含量

通过微波辅助提取的方式,以延胡索叶总生物碱含量为考察指标,通过单因素试验和正交试验对总生物碱提取方法进行优化。重点考察了微波提取温度、时间、料液比、提取缓冲液pH值等因素对延胡索叶总生物碱得率的影响。各因素对延胡索叶总生物碱提取量的影响大小依次为:提取缓冲液pH值料液比提取温度。其最佳的提取方法为:提取缓冲液pH值为1. 0,料液比1∶100,提取温度60℃,提取时间20 min。在此条件下,叶总生物碱含量为25. 910 mg/g。利用微波辅助提取延胡索叶中总生物碱,不仅耗时短,效率高,而且操作简单、稳定,为延胡索叶总生物碱含量测定提供一定的技术支持。     

长序虎皮楠果实中的一个新的生物碱（英文）

从长序虎皮楠（Daphniphyllum longeracemosum）果实的甲醇提取物中分离得到一个新的虎皮楠生物碱和三个已知的环烯醚萜苷型虎皮楠生物碱。通过现代波谱解析技术鉴定为daphlongeranine F（1）,caldaphnidine F（2）,daphcalycinosidine B（3）and daphcalycinosidine C（4）。其中,三个环烯醚萜苷虎皮楠生物碱系首次从该种分离得到。     

丽江乌头根中的二萜生物碱成分研究

为了寻找丽江乌头中结构新颖的化合物,丰富丽江乌头的化学成分多样性,本文对丽江乌头(Aconitum forrestii Stapf)根部的化学成分进行研究,采用硅胶柱层析从其乙醇提取物中分离得到14个化合物。通过HR-ESI-MS、1D和2D NMR等波谱技术鉴定了它们的结构,其中化合物1是一个新的乌头碱型二萜生物碱,命名为8-O-methyl-14-O-anisoylchasmanine(1)。其余13个化合物均为已知化合物:14-acetoxy-8-O-methylsachaconitine(2)、14-acetyltalatizamine(3)、talatisamine(4)、chasmanine(5)、ezochasmanine(6)、crassicautine(7)、geniculatine C(8)、cammaconine(9)、vilmoraconitine(10)、aconitramine A(11)、vilmorrianine G(12)、hemsleyaconitine G(13)和heterophylloidine(14)。测试了所有化合物对阿霉素诱导的H9c2心肌细胞损伤的保护活性,结果显示化合物3、10、11和12表现出一定的保护作用。     

4-Deoxyraputindole C induces cell death and cell cycle arrest in tumor cell lines

Several molecules extracted from natural products exhibit different biological activities, such as ion channel modulation, activation of signaling pathways, and anti-inflammatory or antitumor activity. In this study, we tested the antitumor ability of natural compounds extracted from the Raputia praetermissa plant. Among the compounds tested, an alkaloid, here called compound S4 (4-Deoxyraputindole C), showed antitumor effects against human tumor lineages. Compound S4 was the most active against Raji, a lymphoma lineage, promoting cell death with characteristics that including membrane permeabilization, dissipation of the mitochondrial potential, increased superoxide production, and lysosomal membrane permeabilization. The use of cell death inhibitors such as Z-VAD-FMK (caspase inhibitor), necrostatin-1 (receptor-interacting serine/threonine-protein kinase 1 inhibitor), E-64 (cysteine peptidases inhibitor), and N-acetyl- L -cysteine (antioxidant) did not decrease compound S4-dependent cell death. Additionally, we tested the effect of cellular activity on adherent human tumor cells. The highest reduction of cellular activity was observed in A549 cells, a lung carcinoma lineage. In this lineage, the effect on the reduction of the cellular activity was due to cell cycle arrest, without plasma membrane permeabilization, loss of the mitochondrial potential or lysosomal membrane permeabilization. Compound S4 was able to inhibit cathepsin B and L by a nonlinear competitive (negative co-operativity) and simple-linear competitive inhibitions, respectively. The potency of inhibition was higher against cathepsin L. Compound S4 promoted cell cycle arrest at G ₀ and G ₂ phase, and increase the expression of p16 and p21 proteins. In conclusion, compound S4 is an interesting molecule against cancer, promoting cell death in the human lymphoma lineage Raji and cell cycle arrest in the human lung carcinoma lineage A549.     

(-)-Amarbellisine, a lycorine-type alkaloid from Amaryllis belladonna L. growing in Egypt

A new lycorine-type alkaloid, named (-)-amarbellisine, was isolated from the bulbs of Egyptian Amaryllis belladonna L. together with the well known alkaloids (-)-lycorine, (-)-pancracine, (+)-vittatine, (+)-11-hydroxyvittatine, and (+)-hippeastrine. The new alkaloid, containing the pyrrolo[de]phenanthridine ring system, was essentially characterised by spectroscopic and optical methods, and proved to be the 2-methoxy-3a,4,5,7,11b,11c-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridinol. By using HPTLC technique we also carried out a comparative study of the relative and total alkaloidal content at two different stages of plant growth. Finally, the antimicrobial activity of the isolated alkaloids was assayed.     

棕色扁海绵中的吡咯生物碱

从中国南海棕色扁海绵Phakellia fusca Schimidt的乙醇浸提物中,分离得到3个吡咯生物碱,结合理化性质,波谱分析,文献检索,确定其结构分别为4,5-二溴-1H-吡咯-2-甲酸甲酯(1)、4,5-二溴-3-氰-1H-吡咯-2-甲酸甲酯(2)、4,5-二溴-1H-吡咯-2-甲酰氨(3)。其中化合物(2)未见文献报道。