tocochromanol

Tocochromanol
  • 文章类型: Journal Article
    随着气候变化影响的增加,建立更具可持续性和健壮的植物,例如沙漠日期(Balanitesaegyptiaca)似乎是必要的。以其在干旱条件下的韧性而闻名,这棵树有可能成为更重要的食物来源,特别是它有可能产生食用油。这项研究将Balanites仁油(BKO)作为干旱地区的有前途的油源,研究地理起源和环境因素的影响。对摩洛哥和苏丹BKO样品进行了分析,并与毛里塔尼亚BKO进行了比较。在脂肪酸谱中,不饱和脂肪酸占BKO概况的70%以上,以亚油酸(Li)为主,油酸(Ol),棕榈酸(Pa),和硬脂酸(St)。因此,主要的三酰甘油是PaLiLi,PaLiOl,LiLiOl,OlLiOl,和StLiOl。α-生育酚在生育色满醇组成中占主导地位(324至607mg/kg),其次是γ-生育酚(120至226mg/kg),占总生育色原醇的90%。BKO中的总植物甾醇含量范围为871至2218mg/kg油,β-谷甾醇占主导地位(58%至74%)。主成分分析表明,地理起源显著影响BKO组成,强调环境因素,特别是缺水和/或温度。值得注意的是,摩洛哥BKO是从干旱和冬季温度相对较低的地区收集的,展示了脂肪酸的独特轮廓,植物甾醇,和tocochromanols.BKO的增值为干旱地区的当地农业发展提供了机会,也为世界其他地区的植物发展和农业实践提供了榜样。
    With the increasing impacts of climate change, establishing more sustainable and robust plants such as desert dates (Balanites aegyptiaca) seems to be necessary. Known for its resilience in arid conditions, this tree has the potential to become a more important food source, particularly for its potential to yield edible oil. This study characterized Balanites kernel oil (BKO) as a promising oil source in arid regions, studying the influence of geographical origin and environmental factors. Moroccan and Sudanese BKO samples were analyzed and compared with Mauritanian BKO. In the fatty acid profile, unsaturated fatty acids constituted over 70% of the BKO profile, with a predominance of linoleic acid (Li), oleic acid (Ol), palmitic acid (Pa), and stearic acid (St). Consequently, the predominant triacylglycerols were PaLiLi, PaLiOl, LiLiOl, OlLiOl, and StLiOl. α-Tocopherol dominated the tocochromanol composition (324 to 607 mg/kg), followed by γ-tocopherol (120 to 226 mg/kg), constituting 90% of the total tocochromanols. The total phytosterol content in BKO ranged from 871 to 2218 mg/kg oil, with β-sitosterol dominating (58% to 74%). Principal Component Analysis revealed that the geographical origin significantly influences BKO composition, emphasizing environmental factors, particularly water deficit and/or temperatures. Notably, Moroccan BKO collected from an area characterized by high aridity and relatively low winter temperatures, showcased a unique profile in fatty acid, phytosterols, and tocochromanols. The valorization of BKO presents an opportunity for local agricultural development in arid regions and a role model for plant development and agricultural practices in other parts of the world.
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  • 文章类型: Journal Article
    方法:抗氧化剂生色色满醇-8(PC-8)是一种与γ-生育三烯酚不同的生育色满醇,其具有8个而不是3个异戊二烯单元的不饱和侧链。最近从亚麻籽油中分离出PC-8,这表明另外存在两个以前未知的同系物的较低份额,塑性色满醇-7(PC-7)和塑性色满醇-9(PC-9),其在γ-苯并二氢吡喃醇主链上分别具有七个和九个类异戊二烯单元。这里,快速LC-Orbitrap-HRMS方法用于测定7种植物油和植物提取物中的PC-7和PC-9。
    结果:通过皂化后的LC-Orbitrap-HRMS分析,在所有8个研究样品中确认了PC-7、PC-8和PC-9的存在。两种亚麻籽油中的PC-8含量约为315-350mgkg-1,油菜籽油中约75mgkg-1,约38mgkg-1在山茶花油中,在两种芥末油中约80-120mgkg-1,在蜡烛坚果油中约90mgkg-1,通过定量确定斜视叶中的≈900mgkg-1干重。PC-7和PC-9的半定量表明PC-7和PC-9以不同的相对比率存在约0.1-1%。
    结论:关注维生素E和其他生育色曼醇的研究人员特别感兴趣,因为它们的生物活性尚未被开发。
    METHODS: The antioxidant plastochromanol-8 (PC-8) is a tocochromanol which differs from γ-tocotrienol in having an unsaturated side chain of eight instead of three isoprene units. The recent isolation of PC-8 from flaxseed oil indicates the additional presence of lower shares of two previously unknown homologues, plastochromanol-7 (PC-7) and plastochromanol-9 (PC-9), which feature seven and nine isoprenoid units respectively on the γ-chromanol backbone. Here, a fast LC-Orbitrap-HRMS method is applied for the determination of PC-7 and PC-9 in seven plant oils and a plant extract.
    RESULTS: The presence of PC-7, PC-8, and PC-9 is confirmed in all eight investigated samples by LC-Orbitrap-HRMS analysis after saponification. PC-8 amounts of ≈315-350 mg kg-1 in two flaxseed oils, ≈75 mg kg-1 in rapeseed oil, ≈38 mg kg-1 in camelina oil, ≈80-120 mg kg-1 in two mustard oils, ≈90 mg kg-1 in candle nut oil, and ≈900 mg kg-1 dry weight in Cecropia leaves are determined by quantification. Semi-quantification of PC-7 and PC-9 indicated the presence of ≈0.1-1% of PC-7 and PC-9 in varied relative ratios.
    CONCLUSIONS: The novel plastochromanol homologues are of particular interest to researchers with focus on vitamin E and other tocochromanols because of their unexplored bioactivity.
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  • 文章类型: Journal Article
    维生素E生育色酚是通过使用香叶基香叶基二磷酸(GGDP)进行生育三烯酚生物合成和植基二磷酸(PDP)进行生育酚生物合成,通过匀浆物的异戊二烯化在植物中产生的。均相香叶基香叶酰转移酶(HGGT),使用GGDP进行戊烯化,是一个成熟的目标,用于油籽托科色原醇生物强化,有效地绕过叶绿素连接的途径,限制了PDP的维生素E生物合成。在这份报告中,我们探索了通过将种子特异性HGGT表达与增加的生物合成和/或减少的匀浆分解代谢相结合,最大化油料作物camelina(Camelinasativa)中生育色原醇生产的可行性。质体靶向的大肠杆菌TyrA编码的分支酸变位酶/预苯酸脱氢酶和拟南芥羟基苯基丙酮酸双加氧酶(HPPD)cDNA在种子中共表达,以绕过反馈调节的步骤并增加进入匀浆生物合成的通量。匀浆加氧酶(HGO)基因的种子特异性RNAi也抑制了匀浆分解代谢,这引发了均质物降解。在没有HGGT表达的情况下,在HPPD/TyrA共表达的情况下,生育色酚增加了2.5倍,与未转化种子的水平相比,HGO抑制是1.4倍。在添加HGORNAi的HPPD/TyrA细胞系中没有观察到生育色酚的进一步增加。单独的HGGT表达可使种子中的生育色满醇浓度增加〜四倍,达到≤1400μg/g种子重量。当与HPPD/TyrA共表达结合时,我们获得了另外3倍的生育色原醇浓度增加,表明匀浆物浓度限制了HGGT最大生育色原醇产量的能力。HGORNAi的添加进一步将生育色满醇浓度增加到5000μg/g种子重量,在一个工程油料种子中前所未有的生育色原醇浓度。从工程种子获得的代谢组学数据提供了与“极端”生育苯并二氢吡喃醇生产相关的表型变化的见解。
    Vitamin E tocochromanols are generated in plants by prenylation of homogentisate using geranylgeranyl diphosphate (GGDP) for tocotrienol biosynthesis and phytyl diphosphate (PDP) for tocopherol biosynthesis. Homogentisate geranylgeranyl transferase (HGGT), which uses GGDP for prenylation, is a proven target for oilseed tocochromanol biofortification that effectively bypasses the chlorophyll-linked pathway that limits PDP for vitamin E biosynthesis. In this report, we explored the feasibility of maximizing tocochromanol production in the oilseed crop camelina (Camelina sativa) by combining seed-specific HGGT expression with increased biosynthesis and/or reduced homogentisate catabolism. Plastid-targeted Escherichia coli TyrA-encoded chorismate mutase/prephenate dehydrogenase and Arabidopsis hydroxyphenylpyruvate dioxygenase (HPPD) cDNA were co-expressed in seeds to bypass feedback-regulated steps and increase flux into homogentisate biosynthesis. Homogentisate catabolism was also suppressed by seed-specific RNAi of the gene for homogentisate oxygenase (HGO), which initiates homogentisate degradation. In the absence of HGGT expression, tocochromanols were increased by ∼2.5-fold with HPPD/TyrA co-expression, and ∼1.4-fold with HGO suppression compared to levels in non-transformed seeds. No further increase in tocochromanols was observed in HPPD/TyrA lines with the addition of HGO RNAi. HGGT expression alone increased tocochromanol concentrations in seeds by ∼four-fold to ≤1400 μg/g seed weight. When combined with HPPD/TyrA co-expression, we obtained an additional three-fold increase in tocochromanol concentrations indicating that homogentisate concentrations limit HGGT\'s capacity for maximal tocochromanol production. The addition of HGO RNAi further increased tocochromanol concentrations to 5000 μg/g seed weight, an unprecedented tocochromanol concentration in an engineered oilseed. Metabolomic data obtained from engineered seeds provide insights into phenotypic changes associated with \"extreme\" tocochromanol production.
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  • 文章类型: Journal Article
    在14种豆科木材中研究了生物活性亲脂性化合物,农林业,药用或观赏用途,但对阐明其在食品添加剂和补充剂生产中的潜力几乎没有工业意义。调查的树种是:金合欢,相思,AlbiziaLebbeck,Albiziaododatissima,紫荆花,决明子瘘,黄菊,Delonixregia,Entadaphaseoloides,Hardwickiabinata,云杉,SenegaliaCatechu,Sesbaniasesban和Vachellianilotica。用色谱法分析了成熟种子的己烷提取油的脂肪酸组成(GC-MS),生育色原醇(RP-HPLC/FLD),角鲨烯和甾醇(GC-FID)含量。采用分光光度法测定总类胡萝卜素含量。结果表明,油产率普遍较低(1.75-17.53%);最高的是H.binata。亚油酸在所有样品中所占比例最大(占总脂肪酸的40.78%至62.28%)。其次是油酸(14.57-34.30%)和棕榈酸(5.14-23.04%)。生育苯并二醇的总含量为100.3至367.6mg100g-1油。D.regia是最丰富的,唯一含有大量的生育三烯酚,而其他油几乎只含有生育酚,以α-生育酚或γ-生育酚为主。总的类胡萝卜素含量最高的是A.auriculiformis(23.77mg100g-1),S.sesban(23.57mg100g-1)和A.ododatissima(20.37mg100g-1),范围为0.7至23.7mg100g-1油。总甾醇含量为240.84至2543mg100g-1;A.concinna种子油是最丰富的;但是,其油收率非常低(1.75%)。β-谷甾醇或Δ5-豆甾醇占甾醇部分的主导地位。只有C.瘘管油含有大量的角鲨烯(303.1mg100g-1),但由于作为角鲨烯的工业来源而受到低油产量的限制。总之,A.auriculiformis种子可能具有生产富含类胡萝卜素的油的潜力,和H.binata种子油具有相对较高的产量和生育酚含量,将其标记为这些化合物的潜在来源。
    Bioactive lipophilic compounds were investigated in 14 leguminous tree species of timber, agroforestry, medicinal or ornamental use but little industrial significance to elucidate their potential in food additive and supplement production. The tree species investigated were: Acacia auriculiformis, Acacia concinna, Albizia lebbeck, Albizia odoratissima, Bauhinia racemosa, Cassia fistula, Dalbergia latifolia, Delonix regia, Entada phaseoloides, Hardwickia binata, Peltophorum pterocarpum, Senegalia catechu, Sesbania sesban and Vachellia nilotica. The hexane-extracted oils of ripe seeds were chromatographically analysed for their fatty acid composition (GC-MS), tocochromanol (RP-HPLC/FLD), squalene and sterol (GC-FID) content. A spectrophotometrical method was used to determine total carotenoid content. The results showed generally low oil yield (1.75-17.53%); the highest was from H. binata. Linoleic acid constituted the largest proportion in all samples (40.78 to 62.28% of total fatty acids), followed by oleic (14.57-34.30%) and palmitic (5.14-23.04%) acid. The total tocochromanol content ranged from 100.3 to 367.6 mg 100 g-1 oil. D. regia was the richest and the only to contain significant amount of tocotrienols while other oils contained almost exclusively tocopherols, dominated by either α-tocopherol or γ-tocopherol. The total carotenoid content was highest in A. auriculiformis (23.77 mg 100 g-1), S. sesban (23.57 mg 100 g-1) and A. odoratissima (20.37 mg 100 g-1), and ranged from 0.7 to 23.7 mg 100 g-1 oil. The total sterol content ranged from 240.84 to 2543 mg 100 g-1; A. concinna seed oil was the richest by a wide margin; however, its oil yield was very low (1.75%). Either β-sitosterol or Δ5-stigmasterol dominated the sterol fraction. Only C. fistula oil contained a significant amount of squalene (303.1 mg 100 g-1) but was limited by the low oil yield as an industrial source of squalene. In conclusion, A. auriculiformis seeds may hold potential for the production of carotenoid-rich oil, and H. binata seed oil has relatively high yield and tocopherol content, marking it as a potential source of these compounds.
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  • 文章类型: Journal Article
    意义:氧气保护,双自由基,随着光合生物大约27亿年的进化,它成为了一种必需品。α-生育酚是必不可少的,在从植物到人的生物体中的保护作用。提供了导致严重维生素E(α-生育酚)缺乏的人类病症的概述。最新进展:α-生育酚通过阻止脂质过氧化在氧气保护系统中发挥关键作用,其诱发的损害,和铁性凋亡导致的细胞死亡。细菌和植物的最新发现支持了为什么脂质过氧化对生命如此危险以及为什么生育色酚家族对需氧生物和植物至关重要的概念。关键问题:提出了防止脂质过氧化的传播是脊椎动物中α-生育酚需求的基础的假设,并且进一步指出其缺乏会失调能量代谢。一碳代谢,和硫醇稳态。通过从相邻途径招募中间代谢物来维持有效的脂质过氧化氢消除,α-生育酚功能不仅与NADPH代谢及其通过戊糖磷酸途径通过葡萄糖代谢的形成有关,而且与含硫氨基酸代谢和一碳代谢有关。未来方向:来自人类的证据,动物,植物支持这个假设,但未来的研究需要评估检测脂质过氧化并导致随之而来的代谢失调的遗传传感器。抗氧化剂.氧化还原信号。38,775-791。
    Significance: Protection from oxygen, a diradical, became a necessity with the evolution of photosynthetic organisms about 2.7 billion years. α-Tocopherol plays an essential, protective role in organisms from plants to people. An overview of human conditions that result in severe vitamin E (α-tocopherol) deficiency is provided. Recent Advances: α-Tocopherol has a critical role in the oxygen protection system by stopping lipid peroxidation, its induced damage, and cellular death by ferroptosis. Recent findings in bacteria and plants support the concept of why lipid peroxidation is so dangerous to life and why the family of tocochromanols are essential for aerobic organisms and for plants. Critical Issues: The hypothesis that prevention of the propagation of lipid peroxidation is the basis for the α-tocopherol requirement in vertebrates is proposed and further that its absence dysregulates energy metabolism, one-carbon metabolism, and thiol homeostasis. By recruiting intermediate metabolites from adjacent pathways to sustain effective lipid hydroperoxide elimination, α-tocopherol function is linked not only to NADPH metabolism and its formation through the pentose phosphate pathway via glucose metabolism but also to sulfur-containing amino acid metabolism and to one-carbon metabolism. Future Directions: Evidence from humans, animals, and plants supports the hypothesis, but future studies are needed to assess the genetic sensors that detect lipid peroxidation and cause the ensuing metabolic dysregulation. Antioxid. Redox Signal. 38, 775-791.
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  • 文章类型: Journal Article
    在本研究中,对四百十八份植物油样品进行了生育酚(T)和生育三烯酚(T3)的研究,包括31个家庭,82种,和五个跨物种。15种以生育三烯酚为主,而六十七-通过生育酚。在研究的样品中,γ-T的平均比例几乎是生育色原醇总含量的一半(49.3%),而α-T占四分之一(25.0%),其余的生育色酚作为次要成分存在。注意到分类植物的起源与从这些植物获得的油中特征性的生育色满醇特征之间存在着密切的关系。这是第一项研究证明,不仅单子叶植物,而且双子叶植物家族也可以富含生育三烯酚。还显示了统计工具-主成分分析(PCA)和层次聚类分析(HCA)对基于其生育色醇谱的植物样品区分的有用性。
    The tocopherol (T) and tocotrienol (T3) profile were investigated in the present study for four hundred and eighteen plant oil samples, including thirty-one families, eighty-two species, and five cross-species. Fifteen species were dominated by tocotrienols, while sixty-seven - by tocopherols. The mean proportion of γ-T was almost half of the total tocochromanol content (49.3%) in the investigated samples, while α-T constituted to one quarter (25.0%), and the remaining other tocochromanols were present as minor constituents. A strong relationship between the taxonomic plant origin and the presence of the characteristic tocochromanol profile in oils obtained from those plants was noted. This is the first study to demonstrate that not only monocotyledonous, but also dicotyledons families can be rich in tocotrienols. The usefulness of statistical tools - principal component analysis (PCA) and hierarchical cluster analysis (HCA) for plant sample discrimination based on their tocochromanol profile was also shown.
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  • 文章类型: Journal Article
    天然存在的抗氧化剂塑性色满醇-8(PC-8)是生育色满醇(维生素E)家族的成员,其侧链中具有八个不饱和异戊二烯单元,而γ-生育三烯酚则为三个。由于缺乏商用PC-8标准,我们开发了一条途径来获得相关数量的高纯度PC-8。具体来说,对320克亚麻籽油进行皂化,并通过凝胶渗透色谱法富集庞大的PC-8。使用溶剂系统正己烷/三氟甲苯/乙腈(20:7:13,v/v/v)进行逆流色谱。通过使用新型溶剂系统六甲基二硅氧烷/乙腈(1:1,v/v)的离心分配色谱法实现最终纯化。这一步提供了~26毫克PC-8(>99.5%,根据HPLC,GC和NMR分析)。还有两个,检测到迄今未知的少量生育色原醇( The naturally occurring antioxidant plastochromanol-8 (PC-8) is a member of the tocochromanol (vitamin E) family which features eight unsaturated isoprene units in the side chain compared to three in the case of γ-tocotrienol. Due to the lack of a commercially available PC-8 standard, we developed a route to gain relevant amounts of highly pure PC-8. Specifically, ∼320 g flaxseed oil was saponified and the bulky PC-8 was enriched by gel permeation chromatography. It followed countercurrent chromatography using the solvent system n-hexane/benzotrifluoride/acetonitrile (20:7:13, v/v/v). The final purification was achieved by centrifugal partition chromatography using the novel solvent system hexamethyldisiloxane/acetonitrile (1:1, v/v). This step provided ∼26 mg PC-8 (>99.5 %, according to HPLC, GC and NMR analysis). Two further, hitherto unknown minor tocochromanols (<1 % of PC-8) were detected and could be identified to be plastochromanol-7 (PC-7) and plastochromanol-9 (PC-9), i.e. tocochromanols with seven and nine unsaturated isoprene units, respectively, in the side chain.
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  • 文章类型: Journal Article
    维生素E,也被称为生育色原醇,是一种脂溶性抗氧化剂,只能由自然界中的光合生物产生。维生素E不仅在人类饮食中必不可少,但也需要植物环境适应。合成维生素E,作为反应的第一步,特定的异戊烯基基团需要与均质化物结合。经过几十年的研究,一个几乎完整的路线图已经揭示了生育色满醇生物合成途径。然而,叶绿素衍生的异戊烯基前体用于合成生育色醇仍然是一个谜。近年来,通过采用正向遗传筛选和全基因组关联方法,在研究维生素E方面取得了重大成就。在这篇综述中,通过总结维生素E的最新进展,我们提供了迄今为止最新的维生素E生物合成途径的整体观点。此外,我们讨论了维生素E在植物应激反应中的作用及其作为信号分子的潜力。
    Vitamin E, also known as tocochromanol, is a lipid-soluble antioxidant that can only be produced by photosynthetic organisms in nature. Vitamin E is not only essential in human diets, but also required for plant environment adaptions. To synthesize vitamin E, specific prenyl groups needs to be incorporated with homogentisate as the first step of reaction. After decades of studies, an almost complete roadmap has been revealed for tocochromanol biosynthesis pathway. However, chlorophyll-derived prenyl precursors for synthesizing tocochromanols are still a mystery. In recent years, by employing forward genetic screening and genome-wide-association approaches, significant achievements were acquired in studying vitamin E. In this review, by summarizing the recent progresses in vitamin E, we provide to date the most updated whole view of vitamin E biosynthesis pathway. Also, we discussed about the role of vitamin E in plants stress response and its potential as signaling molecules.
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  • 文章类型: Journal Article
    能够产生霉菌毒素的真菌病原体是对谷物种植和收获籽粒安全性的主要威胁之一。因此,提高作物对真菌病的抗性和霉菌毒素的积累是一个关键问题。实现这一目标需要对植物防御机制有深刻的理解,其中大多数涉及专门的代谢物。然而,虽然许多研究已经解决了苯丙素类和类胡萝卜素对植物化学防御的贡献,很少有人处理过生育色酚。Tocochromanols,包括生育酚和生育三烯酚,构成维生素E家族,广泛分布在谷粒中;它们的生物合成途径已被广泛研究,旨在丰富植物油和对抗人类维生素E缺乏症。在这里,我们提供了强有力的假设,主张生育色酚参与植物-真菌病原体相互作用。这些假设是基于它们清除活性氧的能力产生的直接影响,包括脂质过氧自由基,它们抑制真菌生长和霉菌毒素产量的潜力,以及更间接的影响,主要是基于它们在对抗非生物胁迫的植物保护中的作用。
    Fungal pathogens capable of producing mycotoxins are one of the main threats to the cultivation of cereals and the safety of the harvested kernels. Improving the resistance of crops to fungal disease and accumulation of mycotoxins is therefore a crucial issue. Achieving this goal requires a deep understanding of plant defense mechanisms, most of them involving specialized metabolites. However, while numerous studies have addressed the contribution of phenylpropanoids and carotenoids to plant chemical defense, very few have dealt with tocochromanols. Tocochromanols, which encompass tocopherols and tocotrienols and constitute the vitamin E family, are widely distributed in cereal kernels; their biosynthetic pathway has been extensively studied with the aim to enrich plant oils and combat vitamin E deficiency in humans. Here we provide strong assumptions arguing in favor of an involvement of tocochromanols in plant-fungal pathogen interactions. These assumptions are based on both direct effects resulting from their capacity to scavenge reactive oxygen species, including lipid peroxyl radicals, on their potential to inhibit fungal growth and mycotoxin yield, and on more indirect effects mainly based on their role in plant protection against abiotic stresses.
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  • 文章类型: Journal Article
    Pomelo is an important cultivar of the genus Citrus that contains a variety of beneficial nutrients, and its young fruit is an agricultural by-product that is currently not fully utilized because it is often thrown away during cultivation and management. In this study, the dynamics of tocochromanol during young pomelo development were investigated by measuring chlorophyll content, tocochromanol accumulation, and expression levels of related genes during early fruit development. The results showed that chlorophyll content decreased overall during these four developmental stages and had some synergism with tocochromanol. Four tocochromanol components were detected in pomelo of both genotypes, and α-tocopherol was the main component. The tocochromanol content of honey pomelo was highest in the first period, reaching 70 ± 5 μg/g in dry weight (DW), and golden pomelo peaked in the second period at 86.10 ± 0.18 μg/g DW, with an overall decreasing trend in both genotypes. The different gene expression patterns of the tocochromanol biosynthesis pathway could partially explain the changes in these components and further elucidate the regulatory mechanisms of tocochromanol accumulation during early fruit development. As a natural product, young pomelo fruit is an attractive source of tocochromanol and has potential application in industrial production. The results of this study may provide directions for the high additional value utilization of young pomelo fruit.
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