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1.
Three anthraquinones, named anthrasesamones A, B and C, were isolated from the roots of Sesamum indicum, and their respective structures were determined to be 1-hydroxy-2-(4-methylpent-3-enyl)anthraquinone, 1,4-dihydroxy-2-(4-methylpent-3-enyl)anthraquinone and 2-chloro-1,4-dihydroxy-3-(4-methylpent-3-enyl)anthraquinone on the basis of spectroscopic evidence. Two known anthraquinones were also isolated for the first time from S. indicum roots and characterized as 2-(4-methylpent-3-enyl)anthraquinone and (E)-2-(4-methylpenta-1,3-dienyl)anthraquinone. Anthrasesamone C is a rare chlorinated anthraquinone in higher plants. 相似文献
2.
蒽醌衍生物结构及其对小麦白粉病菌生物活性的关系研究 总被引:1,自引:0,他引:1
蒽醌衍生物是植物产生的一类次生代谢产物,对植物病原真菌具有明显的活性。为明确蒽醌衍生物结构与其生物活性之间的关系,以小麦白粉病菌为研究对象,测定了蒽醌及16种蒽醌衍生物对该病菌的活性。结果表明,蒽醌衍生物对小麦白粉病菌的活性明显大于葸醌的活性;甲氧基的位置与活性关系密切,6位是决定活性的关键,活性顺序为5、6位〉1、6位〉6位〉8位。 相似文献
3.
Elyse A. Rodgers-Vieira Zhenfa Zhang Alden C. Adrion Avram Gold Michael D. Aitken 《Applied and environmental microbiology》2015,81(11):3775-3781
Quinones and other oxygenated polycyclic aromatic hydrocarbons (oxy-PAHs) are toxic and/or genotoxic compounds observed to be cocontaminants at PAH-contaminated sites, but their formation and fate in contaminated environmental systems have not been well studied. Anthracene-9,10-dione (anthraquinone) has been found in most PAH-contaminated soils and sediments that have been analyzed for oxy-PAHs. However, little is known about the biodegradation of oxy-PAHs, and no bacterial isolates have been described that are capable of growing on or degrading anthraquinone. PAH-degrading Mycobacterium spp. are the only organisms that have been investigated to date for metabolism of a PAH quinone, 4,5-pyrenequinone. We utilized DNA-based stable-isotope probing (SIP) with [U-13C]anthraquinone to identify bacteria associated with anthraquinone degradation in PAH-contaminated soil from a former manufactured-gas plant site both before and after treatment in a laboratory-scale bioreactor. SIP with [U-13C]anthracene was also performed to assess whether bacteria capable of growing on anthracene are the same as those identified to grow on anthraquinone. Organisms closely related to Sphingomonas were the most predominant among the organisms associated with anthraquinone degradation in bioreactor-treated soil, while organisms in the genus Phenylobacterium comprised the majority of anthraquinone degraders in the untreated soil. Bacteria associated with anthracene degradation differed from those responsible for anthraquinone degradation. These results suggest that Sphingomonas and Phenylobacterium species are associated with anthraquinone degradation and that anthracene-degrading organisms may not possess mechanisms to grow on anthraquinone. 相似文献
4.
虎杖营养器官蒽醌类化合物含量的季节变化 总被引:10,自引:0,他引:10
采用差示分光光度法测定虎杖营养器官中蒽醌类化合物的含量.该法以醋酸镁甲醇液为显色剂,以大黄素作标准对照品.其回归方程y=0.0576x+0.0012,r=0.9962.结果表明,在一个生长期中,各营养器官总蒽醌的变化不明显,蒽醌类化合物在各营养器官中含量的顺序依次为根>叶>茎;三年生的根高于一年生根;幼嫩茎叶的含量高于成熟的茎叶.在三年生根中游离蒽醌的含量在7月和9月出现两个峰值,8月降至最低;一年生根、幼叶、幼茎和老茎中游离蒽醌的含量在7月左右最高;除根外,幼叶的蒽醌类化合物的含量较其它营养器官高,且其生物量大,因此幼叶具有一定的开发前景. 相似文献
5.
Stalman M Koskamp AM Luderer R Vernooy JH Wind JC Wullems GJ Croes AF 《Journal of plant physiology》2003,160(6):607-614
Cell cultures of Morinda citrifolia L. are capable of accumulating substantial amounts of anthraquinones. Chorismate formed by the shikimate pathway is an important precursor of these secondary metabolites. Isochorismate synthase (EC 5.4.99.6), the enzyme that channels chorismate into the direction of the anthraquinones, is involved in the regulation of anthraquinone biosynthesis. Other enzymes of the shikimate pathway such as deoxy-D-arabino-heptulosonate 7-phosphate synthase (EC 4.1.2.15) and chorismate mutase (EC 5.4.99.5) do not play a regulatory role in the process. The accumulation of anthraquinones is correlated with isochorismate synthase activity under a variety of conditions, which indicates that under most circumstances the concentration of the branchpoint metabolite chorismate is not a rate-limiting factor. Anthraquinone biosynthesis in Morinda is strongly inhibited by 2,4-D, but much less by NAA. Both auxins inhibit the activity of isochorismate synthase proportionally to the concomitant reduction in the amount of anthraquinone accumulated. However, the correlation between enzyme activity and rate of biosynthesis is less clear when the activity of the enzyme is very high. In this case, a limiting concentration of precursor may determine the extent of anthraquinone accumulation. Partial inhibition of chorismate biosynthesis by glyphosate leads to less anthraquinone accumulation, but also to a reduction in ICS activity. The complexity of the interference of glyphosate with anthraquinone biosynthesis is illustrated by the effect of the inhibitor in cell cultures of the related species Rubia tinctorum L. in these cells, glyphosate leads to an increase in anthraquinone content and a concomitant rise in ICS activity. All data indicate that the main point of regulation in anthraquinone biosynthesis is located at the entrance of the specific secondary route. 相似文献
6.
Zhang HX Liu MC 《Journal of chromatography. B, Analytical technologies in the biomedical and life sciences》2004,812(1-2):175-181
Rhubarb, as an important Chinese medicine, has many functions owing to containing anthraquinone derivatives. The analysis of anthraquinone derivatives in Chinese rhubarb is reviewed. The analytical techniques include high performance liquid chromatography, capillary electrophoresis, thin-layer chromatography and so on. The main operation parameters in every technique were given. The structures of anthraquinone derivatives and the classification of Chinese rhubarb were summarized too. 相似文献
7.
An unstable anthraquinone was isolated from hairy root cultures of Sesamum indicum after preventing light throughout all experimental procedures. The structure of the (Z)-isomer of a previously isolated anthraquinone was determined to be 2-[(Z)-4-methylpenta-1,3-dien-1-yl]anthraquinone by spectroscopic methods. This compound was readily isomerized to the known (E)-isomer under light. 相似文献
8.
Fukuhara K Oikawa S Hakoda N Sakai Y Hiraku Y Shoda T Saito S Miyata N Kawanishi S Okuda H 《Bioorganic & medicinal chemistry》2007,15(11):3869-3873
Anthraquinones are typical photosensitizers used in photodynamic therapy (PDT). However, systemic toxicity is a major problem for anthraquinones due to their ability not only to bind DNA but also to cause oxidative stress even without photoirradiation. To avoid such disadvantages in cancer therapy, we designed and synthesized a novel 9-nitroanthracene derivative (1) as a precursor of anthraquinone. Under photoirradiation, 1 is converted into anthraquinone via generation of nitric oxide as confirmed by ESR. Strong DNA cleavage specifically at guanine under photoirradiation was also observed, characteristic of DNA-cleaving reactions by photoirradiated anthraquinones. We propose development of 1 as an alternative approach toward PDT that reduces the systemic toxicity of anthraquinone. 相似文献
9.
10.
Growth and anthraquinone biosynthesis by Galium cells were examinedin steady-state substrate-limited conditions using a chemostatcontinuous culture technique. Steady-state growth was obtainedin both sucrose- and phosphate-limiting conditions for periodsup to 60 d. In sucrose-limiting conditions three growth rateswere investigated with doubling times (td) of 25 h, 35 h and40 h, and phosphate-limited growth was obtained at td= 35 h.The kinetics of the growth response to a change in limitingsubstrate concentration in sucrose-limiting conditions was examinedand found to follow closely that predicted by the applicationof Monod's (1950) model obtained for micro-organisms. The anthraquinone content of cells grown in phosphate and sucroselimitation was uniformly similar and at a relatively low level(0.68 mg g1 dry wt.). When the substrate limitation wasrelieved by the addition of the limiting substrate, either phosphate,or sucrose, anthraquinone synthesis was markedly stimulated.The addition of the anthraquinone precursor, orthosuccinyl benzoicacid (OSB) greatly enhanced anthraquinone synthesis in phosphate-limitingconditions but not in sucrose-limited cells. The results show that growth limitation by phosphate and bysucrose causes a suppression of the rate of synthesis of thesecondary metabolite anthraquinone in Galium cells and suggeststhat the metabolic point of suppression is different in eachcase. Key words: Anthraquinone biosynthesis, Galium, Continuous culture, recursor feeding 相似文献
11.
Two anthraquinone derivatives, named anthrasesamones D and E, were isolated from the roots of Sesamum indicum. Their respective structures were determined to be 1,2,4-trihydroxy-3-(4-methylpent-3-enyl)anthraquinone and 1,2-dihydroxy-3-(4-methylpent-3-enyl)anthraquinone on the basis of spectroscopic evidence. 相似文献
12.
《Bioscience, biotechnology, and biochemistry》2013,77(7):1784-1785
Two anthraquinone derivatives, named anthrasesamones D and E, were isolated from the roots of Sesamum indicum. Their respective structures were determined to be 1,2,4-trihydroxy-3-(4-methylpent-3-enyl)anthraquinone and 1,2-dihydroxy-3-(4-methylpent-3-enyl)anthraquinone on the basis of spectroscopic evidence. 相似文献
13.
Je Hyeong Jin Joong Han Shin Ju Hwan Kim In Sik Chung Hyong Joo Lee 《Biotechnology and Bioprocess Engineering》1999,4(4):300-304
To increase the production of anthraquinone colorants in madder (Rubia akane Nakai) cell culture, the effects of elicitation on the colorant production were investigated. Chitosan was the best biotic
elicitor among nine plant derived and microbial derived polysaccharides. When elicited with 25 mg/L chitosan, the total production
was increased approximately two times in a seven-day culture as compared to that in the unelicited cells. Anthraquinone production
was increased in proportion to the contact period up to day 3. Maximum anthraquinone colorants were obtained with 3-day treatment
of chitosan. During chitosan elicitation, the total production was increased 1.3 times in MS medium containing galactose as
compared to that containing sucrose. The degree of deacetylation in chitosan and the use of growth regulator or addition of
precursor did not affect the production of anthraquinone colorants. When madder cells were elicited at optimum condition,
anthraquinone concentration and specific anthraquinone content increased 1.3 times (0.69 g/L) and 2.2 times (0.32 g/g DCW),
respectively. 相似文献
14.
In the photosynthetic reaction centre (RC) from the purple bacterium Rhodobacter sphaeroides, the primary quinone, a ubiquinone-10 (Q(A)), has been substituted by anthraquinone. Three-dimensional crystals have been grown from the modified RC and its structure has been determined by X-ray crystallography to 2.4 A resolution. The bindings of the head-group from ubiquinone-10 and of the anthraquinone ring are very similar. In particular, both rings are parallel to each other and the hydrogen bonds connecting the native ubiquinone-10 molecule to AlaM260 and HisM219 are conserved in the anthraquinone containing RC. The space of the phytyl tail missing in the anthraquinone exchanged RC is occupied by the alkyl chain of a detergent molecule. Other structural changes of the Q(A)-binding site are within the limit of resolution. Our structural data bring strong credit to the very large amount of spectroscopic data previously achieved in anthraquinone-replaced RCs and which have participated in the determination of the energetics of the quinone system in bacterial RCs. 相似文献
15.
《Bioscience, biotechnology, and biochemistry》2013,77(10):2788-2790
An unstable anthraquinone was isolated from hairy root cultures of Sesamum indicum after preventing light throughout all experimental procedures. The structure of the (Z)-isomer of a previously isolated anthraquinone was determined to be 2-[(Z)-4-methylpenta-1,3-dien-1-yl]anthraquinone by spectroscopic methods. This compound was readily isomerized to the known (E)-isomer under light. 相似文献
16.
Haruna K Kanezaki H Tanabe K Dai WM Nishimoto S 《Bioorganic & medicinal chemistry》2006,14(13):4427-4432
Propargylic sulfones are known as pH-dependent DNA cleaving agents. We have designed a novel propargylic sulfone conjugated with an anthraquinone structure and evaluated its DNA binding and cleavage characteristics. The propargylic sulfone 3 showed high intercalating ability attributable to anthraquinone chromophore, leading to the efficient alkylation of DNA. The anthraquinone chromophore in 3 also acted as a photosensitizer, and photoirradiation of 3 with DNA induced one-electron oxidation, resulting in the further DNA cleavage. Evaluation of the effect of 3 against EMT6/KU cells revealed that 3 exhibited potent cytotoxicity, even without photoirradiation. 相似文献
17.
The mechanism of metal-mediated DNA damage by carcinogenic danthron (1,8-dihydroxyanthraquinone) and anthraquinone was investigated by the DNA sequencing technique using 32P-labeled human DNA fragments obtained from the human c-Ha-ras-1 proto-oncogene and the p53 tumor suppressor gene. Danthron caused DNA damage particularly at guanines in the 5'-GG-3', 5-GGGG-3', 5'-GGGGG-3' sequences (damaged bases are underlined) in the presence of Cu(II), cytochrome P450 reductase and the NADPH-generating system. The DNA damage was inhibited by catalase and bathocuproine, suggesting the involvement of H2O2 and Cu(I). The formation of 8-oxo-7,8-dihydro-2'-deoxyguanosine increased with increasing concentration of danthron. On the other hand, carcinogenic anthraquinone induced less oxidative DNA damage than danthron. Electron spin resonance study showed that the semiquinone radical could beproduced by P450 reductase plus NADPH-mediated reduction of danthron, while little signal was observed with anthraquinone. These results suggest that danthron is much more likely to be reduced by P450 reductase and generate reactive oxygen species through the redox cycle, leading to more extensive Cu(II)-mediated DNA damage than anthraquinone. In the case of anthraquinone, its hydroxylated metabolites with similar reactivity to danthron may participate in DNA damage in vivo. We conclude that oxidative DNA damage by danthron and anthraquinone seems to be relevant for the expression of their carcinogenicity. 相似文献
18.
In order to investigate the intermediacy of 2-(4-methylpent-3-en-1-yl)anthraquinone (MPAQ), a possible intermediate for the biosynthesis of anthraquinone derivatives in sesame (Sesamum indicum), 2H-labeled MPAQ was administered to a hairy root culture of S. indicum. Efficient conversion of fed MPAQ to 2-[(Z)-4-methylpenta-1,3-dien-1-yl]anthraquinone ((Z)-MPDEAQ) was observed. Furthermore, administration experiment with 2H-labeled 2-geranyl-1,4-naphthohydroquinone, another possible intermediate, showed that it was converted to MPAQ and (Z)-MPDEAQ. The results clearly demonstrated that these substrates are the actual precursors for the production of (Z)-MPDEAQ. In contrast, neither MPAQ nor 2-geranyl-1,4-naphthohydroquinone was converted to anthrasesamone B and 2,3-epoxyanthrasesamone B, other anthraquinone derivatives in the hairy roots, suggesting that these substrates may not be the common precursors in the biosynthesis of anthraquinone derivatives. 相似文献
19.
Monomeric and Dimeric 9‐O Anthraquinone and Phenanthryl Derivatives of Cinchona Alkaloids as Chiral Solvating Agents for the NMR Enantiodiscrimination of Chiral Hemiesters
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Gloria Uccello Barretta Alessandro Mandoli Federica Balzano Federica Aiello Beatrice De Nicola Alessandro Del Grande 《Chirality》2015,27(10):693-699
Mono‐ and bis‐alkaloid chiral auxiliaries with anthraquinone or phenanthryl cores were probed as chiral solvating agents (CSAs) for the enantiodiscrimination of chiral cyclic hemiesters. The dimeric anthraquinone derivative and the monomeric phenanthryl one showed remarkable efficiency in the nuclear magnetic resonance (NMR) differentiation of enantiomeric mixtures of hemiesters. An anthraquinone analogous with a single alkaloid unit was remarkably less effective. The conformational prevalence of the chiral auxiliaries were ascertained by NMR. Chirality 27:693–699, 2015. © 2015 Wiley Periodicals, Inc. 相似文献
20.
Antisense oligonucleotides bearing an anthraquinone moiety at an internucleotide linkage were synthesized utilizing the stereoisomers of anthraquinone incorporated T-C dimer phosphoramidite derivatives. Some physicochemical properties of the anthraquinon bearing oligomers were investigated. 相似文献