Secondary Metabolism

次级代谢
  • 文章类型: Journal Article
    DaucuscapillifoliusGilli是在利比亚种植的一种罕见的一年生野生草本植物。它属于伞形科,这是最大的开花植物家族之一。该家族的植物是具有各种生物活性的各种次生代谢产物的重要来源。在本研究中,首次对两种电离模式下的木竹的体内和体外组织的不同提取物以及栽培植物的果实提取物进行了UPLC-ESI-MS/MS分析。我们的结果揭示了测试提取物中87种化合物的初步鉴定,包括32种酚酸及其衍生物;37种黄酮苷和芹菜素苷,木犀草素,Diosmetin,杨梅素和槲皮素,含有葡萄糖,鼠李糖,戊糖和/或葡萄糖醛酸分子;七种花色苷;六种单宁;三种炔属化合物;和三种含氮化合物。上述化合物的初步鉴定是基于它们的保留时间和ESI-MS/MS片段化模式与文献中先前报道的那些的比较。对于这种伞形科植物,我们的结果证实了广泛的次级代谢产物的存在,并报告了生物活性。这项研究是第一批揭示这种稀有植物的植物成分的研究之一。
    Daucus capillifolius Gilli is a rare annual wild herb grown in Libya. It belongs to the Apiaceae family, which is one of the largest flowering plant families. Plants of this family are outstanding sources of various secondary metabolites with various biological activities. A UPLC-ESI-MS/MS analysis of different extracts of in vivo and in vitro tissues of Daucus capillifolius together with the fruit extract of the cultivated plant in both ionization modes was carried out for the first time in the current study. Our results reveal the tentative identification of eighty-seven compounds in the tested extracts, including thirty-two phenolic acids and their derivatives; thirty-seven flavonoid glycosides and aglycones of apigenin, luteolin, diosmetin, myricetin and quercetin, containing glucose, rhamnose, pentose and/or glucuronic acid molecules; seven anthocyanins; six tannins; three acetylenic compounds; and three nitrogenous compounds. The tentative identification of the above compounds was based on the comparison of their retention times and ESI-MS/MS fragmentation patterns with those previously reported in the literature. For this Apiaceae plant, our results confirm the presence of a wide array of secondary metabolites with reported biological activities. This study is among the first ones to shed light on the phytoconstituents of this rare plant.
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  • 文章类型: Journal Article
    目的:本研究的目的是确定接种体积比对土曲霉和金链霉菌深层共培养物中次生代谢产物产生的影响。
    结果:通过使用23种接种物变体开始摇瓶共培养,所述接种物变体包括不同体积的土A和S.rimosus预培养物。此外,无菌对照与共培养物平行繁殖。UPLC-MS分析显示存在15种次生代谢物,其中12个都在“A”中找到。地鼠vs.S.rimosus\“地鼠或S.rimosus的共培养和无菌培养。其余3个分子的产生仅记录在共培养物中。次生代谢产物的组成和数量明显取决于接种比例。还注意到,检测类似于给定物种的典型形态形式的丝状结构不足以预测给定代谢物的存在。
    结论:接种比例的修改是唤醒和增强在无菌条件下不生物合成的次生代谢产物的有效策略。
    OBJECTIVE: The aim of this study was to determine the influence of the inoculation volume ratio on the production of secondary metabolites in submerged cocultures of Aspergillus terreus and Streptomyces rimosus.
    RESULTS: The shake flask cocultures were initiated by using 23 inoculum variants that included different volumes of A. terreus and S. rimosus precultures. In addition, the axenic controls were propagated in parallel with the cocultures. UPLC‒MS analysis revealed the presence of 15 secondary metabolites, 12 of which were found both in the \"A. terreus vs. S. rimosus\" cocultures and axenic cultures of either A. terreus or S. rimosus. The production of the remaining 3 molecules was recorded solely in the cocultures. The repertoire and quantity of secondary metabolites were evidently dependent on the inoculation ratio. It was also noted that detecting filamentous structures resembling typical morphological forms of a given species was insufficient to predict the presence of a given metabolite.
    CONCLUSIONS: The modification of the inoculation ratio is an effective strategy for awakening and enhancing the production of secondary metabolites that are not biosynthesized under axenic conditions.
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  • 文章类型: Journal Article
    背景:自2020年初COVID-19爆发以来,研究人员和研究人员正在继续寻找针对该疾病的药物和/或疫苗。如前所述,药用植物是很好的抗病毒来源,因为它们的次级化合物可以治愈疾病,帮助患者生存。在该领域中所提交的专利有增长的趋势。
    目的:在本研究中,我们测试并建议五种草药提取物的抑制潜力,包括7α-乙酰氧基丙酮,Curzerene,英美素,Harmaline,和大麻二酚对COVID-19的重要抗病毒靶标模型具有抗病毒活性,木瓜蛋白酶样蛋白酶(PLpro),非结构蛋白15(NSP15),RNA依赖性RNA聚合酶和核心蛋白酶的分子对接研究.
    方法:提取丹参根,干,用铣床粉碎。使用分液漏斗通过两相萃取分离根提取物的水相和二氯甲烷相。使用柱色谱法进行分离。从卵白质数据库(PDB)获得并修改了COVID-19重要抗病毒药物靶点的模子。为了研究所研究分子之间的结合差异,进行对接研究.
    结果:这些草药化合物是从丹参中提取的,姜黄,乳香,Harmala-Poganumharmala,和大麻草药,分别。所有化合物对COVID-19主要靶标的结合能位于2.22-5.30kcal/mol的有限区域内。这个范围的结合能可以支持我们关于上述结构的次级代谢物对COVID-19存在抑制作用的假设。一般来说,在调查的草药结构中,具有最高结合能的大麻二酚和7α-乙酰氧基丙酮化合物具有最大的抑制潜力。最小的抑制作用通过最低的结合亲和力与Curzerene和Incen素结构相关。
    结论:结合能的势垒基础的总体排列顺序如下:大麻二酚>7α-乙酰氧基芳酮>Harmaline>因乐素>Curzerene。最后,研究的草药化合物在上述靶标上的对接得分范围表明,对这些靶标的可能抑制作用遵循以下顺序:主要蛋白酶>RNA依赖性RNA聚合酶>PLpro>NSP15>刺突糖蛋白。
    BACKGROUND: Since the COVID-19 outbreak in early 2020, researchers and studies are continuing to find drugs and/or vaccines against the disease. As shown before, medicinal plants can be very good sources against viruses because of their secondary compounds which may cure diseases and help in survival of patients. There is a growing trend in the filed patents in this field.
    OBJECTIVE: In the present study, we test and suggest the inhibitory potential of five herbal based extracts including 7α-acetoxyroyleanone, Curzerene, Incensole, Harmaline, and Cannabidiol with antivirus activity on the models of the significant antiviral targets for COVID-19 like spike glycoprotein, Papain-like protease (PLpro), non-structural protein 15 (NSP15), RNA-dependent RNA polymerase and core protease by molecular docking study.
    METHODS: The Salvia rythida root was extracted, dried, and pulverized by a milling machine. The aqueous phase and the dichloromethane phase of the root extractive were separated by two-phase extraction using a separatory funnel. The separation was performed using the column chromatography method. The model of the important antivirus drug target of COVID-19 was obtained from the Protein Data Bank (PDB) and modified. TO study the binding difference between the studied molecules, the docking study was performed.
    RESULTS: These herbal compounds are extracted from Salvia rhytidea, Curcuma zeodaria, Frankincense, Peganum harmala, and Cannabis herbs, respectively. The binding energies of all compounds on COVID-19 main targets are located in the limited area of 2.22-5.30 kcal/mol. This range of binding energies can support our hypothesis for the presence of the inhibitory effects of the secondary metabolites of mentioned structures on COVID-19. Generally, among the investigated herbal structures, Cannabidiol and 7α- acetoxyroyleanone compounds with the highest binding energy have the most inhibitory potential. The least inhibitory effects are related to the Curzerene and Incensole structures by the lowest binding affinity.
    CONCLUSIONS: The general arrangement of the basis of the potential barrier of binding energies is in the order below: Cannabidiol > 7α-acetoxyroyleanone > Harmaline> Incensole > Curzerene. Finally, the range of docking scores for investigated herbal compounds on the mentioned targets indicates that the probably inhibitory effects on these targets obey the following order: main protease> RNA-dependent RNA polymerase> PLpro> NSP15> spike glycoprotein.
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  • 文章类型: Journal Article
    Prodigiosin(Pg),由许多细菌物种产生的次级代谢,被称为抗癌,抗菌,抗真菌药,免疫抑制剂,抗氧化剂,抗疟疾特性。Pg已经在许多不同的癌细胞系中测试了抗肿瘤活性,但在LU-1,KB细胞系中的研究,和荷瘤小鼠仍然有限。在这项研究中,使用甲磺酸乙酯(EMS)突变粘质沙雷氏菌QBNVTCC910026菌株(GenBank:KX674054.1)以增加Pg的产生。与野生型菌株相比,一种称为EMS5的菌株能够将prodigiosin生物合成产量提高52%。从固体培养基中收集含有Pg的红色细菌色素菌落,用丙酮裂解,用甲苯:乙酸乙酯以9:1(v/v)的比例纯化,然后用于评估潜在的抗癌活性。使用高效液相色谱(HPLC)方法确认Pg的纯度,该方法表明98%的比率。使用1H-NMR和13C-NMR光谱确定的Pg化学式,确认为prodigiosin(Pg)。人乳腺癌细胞系MCF-7,口咽癌KB,特别是肺癌LU-1在体外用于测试纯化的Pg化合物的抗癌活性。它在所有癌细胞系中都显示出较强的抑制能力。此外,分离的Pg能够抑制肿瘤生长,肿瘤体积减少36.82%,28天后结果表明,来自粘质沙雷氏菌QBNVTCC910026菌株的细菌prodigiosin是适合治疗应用的令人鼓舞的片段。
    Prodigiosin (Pg), a secondary metabolism produced by numerous bacterial species, is known as anticancer, antibacterial, antifungal, immunosuppressant, antioxidant, antimalarial properties. Pg has been tested for antitumor activity in many different cancer cell lines but studies in LU-1, KB cell lines, and tumor-bearing mice are still limited. In this study, Serratia marcescens QBN VTCC 910026 strain (GenBank: KX674054.1) was mutated using Ethyl Methanesulfonate (EMS) to increase the production of Pg. One strain known as EMS 5 was capable of increasing prodigiosin biosynthetic yield by 52% when compared to the wild-type strain. Red bacterial pigmented colonies containing Pg were collected from solid media, lysed with acetone, purified with toluene: ethyl acetate at a ratio of 9: 1 (v/v), and then used to evaluate the potential anticancer activity. The purity of Pg was confirmed using a high-performance liquid chromatography (HPLC) method which indicated a 98% rate. Pg chemical formula which was determined using 1H-NMR and 13C-NMR spectroscopy, confirmed as prodigiosin (Pg). Human breast cancer cell lines MCF-7, oropharyngeal cancer KB, and particularly lung cancer LU-1 in vitro were used to test the anticancer activity of purified Pg compound. It showed a strong inhibitory ability in all the cancer cell lines. Furthermore, the isolated Pg had capable of inhibiting tumor growth, the tumor volume decreased by 36.82%, after 28 days. The results indicated that the bacterial prodigiosin from variants Serratia marcescens QBN VTCC 910026 strain is an encouraging fragment suitable for therapeutic applications.
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  • 文章类型: Journal Article
    背景:在巴西用于治疗疾病的最受欢迎的植物之一是Lantanafucata。像大多数草药一样,它的消费是基于大众知识,which,尽管被认为是有效的,可能会引起副作用。
    目的:由于关于岩藻乳杆菌药理特性的科学数据仍处于初期阶段,这项研究旨在评估不同类型提取物的细胞毒性和遗传毒性潜力(输注,水性和水醇),用化学方法描述它们。
    方法:通过A.cepa模型进行细胞毒性测定。研究的细胞毒性参数是分裂细胞数和有丝分裂指数百分比(%MI)。
    结果:A.cepa测定的结果表明,随着浓度的增加,分裂细胞数量和有丝分裂指数百分比减少,对于所有提取物,表明细胞毒性。然而,水醇提取物细胞毒性最强。色谱分析可以表征提取物中的次生代谢产物,非常相似。然而,在水醇提取物中观察到更丰富的类黄酮和三萜类化合物,这表明这些化合物是其更大毒性的原因。
    结论:由于最高剂量的提取物显示具有细胞毒性作用,建议以适度的方式摄入该物种。
    BACKGROUND: One of the most popular plants used to treat diseases in Brazil is Lantana fucata. Like most herbal medicines, its consumption is based on popular knowledge, which, despite being considered effective, may cause side effects.
    OBJECTIVE: Since the scientific data on the pharmacological properties of L. fucata are still incipient, this research aimed to evaluate the cytotoxic and genotoxic potential of different types of extracts (infusion, aqueous and hydroalcoholic), characterizing them chemically.
    METHODS: The cytotoxicity assay was performed by the A. cepa model. The cytotoxicity parameters studied were number of dividing cells and percentage mitotic index (%MI).
    RESULTS: The result of the A. cepa assay showed that there was a decrease in the number of dividing cells and the percentage mitotic index as concentrations increased, for all extracts, indicating cytotoxicity. However, the hydroalcoholic extract was the most cytotoxic. Chromatography analysis allowed the characterization of secondary metabolites in the extracts, which were very similar. However, a greater abundance of flavonoids and triterpenoids was observed in the hydroalcoholic extract, suggesting that these compounds are responsible for its greater toxicity.
    CONCLUSIONS: Since the highest doses of extracts showed to have a cytotoxic effect, it is suggested that the ingestion of this species occurs in a moderate way.
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  • 文章类型: Comparative Study
    植物次生代谢物(SMs)的浓度显示出季节性变化。然而,目前尚不清楚这些非生物和生物因素如何影响SMs的季节性变化。了解SMs是否以及如何重新分配到不同的植物器官是很有意义的,特别是当生物量丢失时,SMs是否被重新分配给剩余的组织,例如,在冬天。在这里,我们使用了雅各贝娅,Jacobaeaaquatica,作为研究系统,两个F1和四个F2杂种在其吡咯啶生物碱(PAs)花束上有所不同。在半自然环境中,在长达14个月的营养阶段研究了这些基因型的一系列克隆。我们发现根和芽中的总PA浓度逐渐增加,直到第二年的春天,此后,它在芽中大量下降。由于季节变化,PA组成的变化显着,但相对较小。人参皂甙样PAs是根中的主要PAs,而Jacobine/芥酸草素样PAs在芽中占主导地位。PA浓度的变化与温度显著相关,天长度,植物年龄。相关分析表明,当冬季失去生物量时,PAs没有重新分配。总的来说,我们的研究表明,每个基因型的PA组成随季节变化的方式不同,但季节变化并没有抵消基因型间PA组成的差异.
    Concentration of plant secondary metabolites (SMs) show seasonal variations. However, it is still not well understood how these abiotic and biotic factors influence the seasonal variations of SMs. In addition, it is of interest to know if and how SMs are reallocated to the different plant organs, in particular whether SMs are reallocated to the remaining tissues when biomass is lost, e.g., during winter. Here we used Jacobaea vulgaris, Jacobaea aquatica, two F1 and four F2 hybrids that differed in their pyrrolizidine alkaloids (PAs) bouquet as a study system. A series of clones of these genotypes were investigated during their vegetative stage spanning 14 months in a semi-natural environment. We found that the total PA concentration in roots and shoots showed a gradual increase until the spring of the second year, whereafter it dropped substantially in shoots. The variation in PA composition due to seasonal changes was significant but relatively small. Senecionine-like PAs were the dominant PAs in roots, while jacobine-/erucifoline-like PAs were dominant in shoots. The variation of PA concentration was significantly correlated with temperature, day length, and plant age. A correlation analysis showed that PAs were not reallocated when biomass was lost in winter. Overall, our study showed that PA composition of each genotype changed over seasons in a different manner but seasonal variation did not overrule the differences in PA composition among genotypes.
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  • 文章类型: Journal Article
    玫瑰planobispora是有效的硫肽抗生素GE2270A的天然生产者。这里,我们提供了在GE2270A生产过程中对P.rosea进行代谢组学和转录组学分析的结果。产生的数据提供了对这种遗传上难以处理的细菌的生物学的有用见解。我们描述了与指数生长期结束相关的蛋白质生物合成和呼吸链关闭的细节。我们还提供了P.rosea中磷酸盐调节子的第一个描述。根据转录组学数据,我们表明,在我们的实验条件下,磷酸盐和铁都限制了红藻的生长。此外,我们鉴定并验证了一个新的生物合成基因簇,该基因簇与红花黄牛铁载体的生产有关。一起,代谢组学和转录组学数据用于告知和完善红牛的第一个基因组尺度代谢模型,这将是一个有价值的框架,用于解释这个有趣但特征不佳的物种的生物学的未来研究。重要性Planobisporarosea是一种遗传上难以处理的细菌,用于以工业规模生产GE2270A。GE2270A是一种有效的硫肽抗生素,目前在临床研究中用作合成两种化合物的前体,用于治疗艰难梭菌感染和痤疮。这里,我们首次对这种重要细菌进行了系统的多组学研究,这提供了一个急需的详细图片的代谢的动态罗西的同时生产GE2270A。
    Planobispora rosea is the natural producer of the potent thiopeptide antibiotic GE2270A. Here, we present the results of a metabolomics and transcriptomics analysis of P. rosea during production of GE2270A. The data generated provides useful insights into the biology of this genetically intractable bacterium. We characterize the details of the shutdown of protein biosynthesis and the respiratory chain associated with the end of the exponential growth phase. We also provide the first description of the phosphate regulon in P. rosea. Based on the transcriptomics data, we show that both phosphate and iron are limiting P. rosea growth in our experimental conditions. Additionally, we identified and validated a new biosynthetic gene cluster associated with the production of the siderophores benarthin and dibenarthin in P. rosea. Together, the metabolomics and transcriptomics data are used to inform and refine the very first genome-scale metabolic model for P. rosea, which will be a valuable framework for the interpretation of future studies of the biology of this interesting but poorly characterized species. IMPORTANCE Planobispora rosea is a genetically intractable bacterium used for the production of GE2270A on an industrial scale. GE2270A is a potent thiopeptide antibiotic currently used as a precursor for the synthesis of two compounds under clinical studies for the treatment of Clostridium difficile infection and acne. Here, we present the very first systematic multi-omics investigation of this important bacterium, which provides a much-needed detailed picture of the dynamics of metabolism of P. rosea while producing GE2270A.
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  • 文章类型: Journal Article
    植物对它们所遭受的环境压力具有记忆功能。当他们受到反复的环境压力时,它们可以快速更好地激活对环境压力的反应和适应机制,从而实现长期稳定繁殖。然而,关于植物生长状态的改善和对植物抗毒素生物合成的影响,大多数相关研究应用于作物和拟南芥,而不是药用植物。在这项研究中,酵母提取物(YE)被用作模拟生物胁迫的诱导子,通过对SASC悬浮细胞(SASC)进行反复胁迫,测量生物量和某些次生代谢产物含量的变化。结果表明,与单一胁迫相比,重复胁迫下SASC的生物量和一些次生代谢产物的积累水平在某些时间点显著增加。本研究证实了SASC可以记忆生物胁迫的现象,并影响SASC中植物抗毒素的积累。此外,这项工作为研究药用植物的跨代应激记忆机制奠定了基础。
    Plants have a memory function for the environmental stress they have suffered. When they are subjected to repeated environmental stress, they can quickly and better activate the response and adaptation mechanism to environmental stress, thus realizing long-term stable reproduction. However, most of the relevant studies are applied to crops and Arabidopsis thaliana rather than medicinal plants about the improvement of plant growth status and the effect on phytoalexin biosynthesis. In this study, yeast extract(YE) was used as an elicitor to simulate biotic stress, and the changes in biomass and the content of some secondary metabolites were measured by giving repeated stresses to Sorbus aucuparia suspension cell(SASC). The results showed that the accumulation levels of biomass and some secondary metabolites in SASC subjected to repeated stress are significantly increased at some time points compared with single stress. A phenomenon that SASC can memorize biotic stress is confirmed in this study and influences phytoalexin accumulation in SASC. Furthermore, the work laid the groundwork for research into the transgenerational stress memory mechanism of medicinal plant.
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  • 文章类型: Journal Article
    生物表面活性剂代表了由细菌产生的一组结构多样的次级代谢产物,酵母,和丝状真菌。它们的特性通常与许多其他属性相关联。对用作针对病原植物真菌的生物抑制剂来源的各种木霉属真菌的观察将注意力集中在与之接触的制剂的通常相当特定的行为上。其中,植物叶子,依赖于应变。因此,对属于该物种的所选菌株的评估:T.atroviride,T.citrinoviride,T.里氏和哈茨木霉对其细胞外分泌表面活性剂的能力进行了研究,同时尝试预先确定它们的化学性质。为此使用了两种无机-有机介质,并且使用各种方法对培养液进行了广泛的测试。在每个测试菌株的培养液中观察到表面张力的降低,特别是T.citrinovirideHL和C1。结果强烈依赖于培养基成分,其中桑德斯1号和MGP1号最有利。使用IR进一步分析分泌的化合物以预先确定它们的化学性质。GC,和NMR。在最有效的生物表面活性剂生产商的情况下,得出表面活性剂的脂肽结构。
    Biosurfactants represent a structurally diverse group of secondary metabolites produced by bacteria, yeasts, and filamentous fungi. Their character is often associated with numerous additional properties. The observation of Trichoderma fungi of various species used as a source of bioinhibitors against pathogenic plants fungi focuses attention to the often quite specific behavior of preparations in contact with, among others, plant leaves, dependent on strain. Thus, an evaluation of the selected strains belonging to the species: T. atroviride, T. citrinoviride,T. reesei and T. harzianum was conducted towards their capability of the extracellular secretion of surfactants, with a simultaneous attempt to pre-determine their chemical nature. Two mineral-organic media were used for this purpose, and the culture fluid was extensively tested using a variety of methods. A decrease in surface tension was observed in culture fluid of each tested strain, especially T. citrinoviride HL and C1. The results strongly depended on medium composition, of which Saunders 1 and MGP 1 were most beneficial. The secreted compounds were further analyzed to pre-determine their chemical nature using IR, GC, and NMR. In the case of most efficient biosurfactant producers, a lipopeptide structure of the surfactants was concluded.
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  • 文章类型: Journal Article
    近几十年来,藻类已被证明是具有生物活性的不同生物活性化合物的来源,这增加了这些生物在食品中的潜在应用,化妆品,Pharmaceutical,动物饲料,和其他工业部门。另一方面,人们对开发控制和/或根除入侵藻类的有效策略越来越感兴趣,因为它们对海洋生态系统和受影响区域的经济具有负面影响。然而,控制措施的应用通常消耗时间和资源,并且无利可图。考虑到这种情况,将入侵藻类物种作为工业应用的生物活性化合物来源的价值化可能是减少其种群的合适策略,同时获得环境和经济效益。为了进行这种实践,有必要评估藻类的化学和营养成分以及提取目标化合物的最有效方法。在西班牙西北部,五种藻类被认为是侵入性的:阿玛塔,钴易碎,龙须草,马尾藻,还有Grateulopiaturuturu.这篇综述简要介绍了它们的主要生物活性化合物,生物活动,和用于回收的提取系统。此外,收集了它们有益特性的证据以及将它们用作水产养殖动物饮食中的补充剂的可能性,以说明它们可能的应用之一。
    In the recent decades, algae have proven to be a source of different bioactive compounds with biological activities, which has increased the potential application of these organisms in food, cosmetic, pharmaceutical, animal feed, and other industrial sectors. On the other hand, there is a growing interest in developing effective strategies for control and/or eradication of invasive algae since they have a negative impact on marine ecosystems and in the economy of the affected zones. However, the application of control measures is usually time and resource-consuming and not profitable. Considering this context, the valorization of invasive algae species as a source of bioactive compounds for industrial applications could be a suitable strategy to reduce their population, obtaining both environmental and economic benefits. To carry out this practice, it is necessary to evaluate the chemical and the nutritional composition of the algae as well as the most efficient methods of extracting the compounds of interest. In the case of northwest Spain, five algae species are considered invasive: Asparagopsis armata, Codium fragile, Gracilaria vermiculophylla, Sargassum muticum, and Grateulopia turuturu. This review presents a brief description of their main bioactive compounds, biological activities, and extraction systems employed for their recovery. In addition, evidence of their beneficial properties and the possibility of use them as supplement in diets of aquaculture animals was collected to illustrate one of their possible applications.
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