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Monoterpene indole alkaloids with anticancer activity from Tabernaemontana species 从 Tabernaemontana 树种中提取的具有抗癌活性的单萜吲哚生物碱
IF 7.7 2区 生物学 Q1 Agricultural and Biological Sciences Pub Date : 2024-04-27 DOI: 10.1007/s11101-024-09964-6
Bruno M. F. Gonçalves, Noélia Duarte, Cátia Ramalhete, Filipa Barbosa, Ana Margarida Madureira, Maria-José U. Ferreira

Indole alkaloids, predominantly found in plants, are a large group of natural product-derived compounds characterized by a remarkable chemical diversity associated with significant biological properties. Among these, terpenoid indole alkaloids are the largest group of secondary metabolites. Tabernaemontana species (Apocynaceae) are widely distributed in tropical and subtropical regions of the world and used in traditional medicine to treat a variety of illnesses, including tumours. These species biosynthesize large quantities of structurally complex monoterpene indole and bisindole alkaloids. Given the compelling biological properties of indole alkaloids, the phytochemical study of Tabernaemontana species has been widely addressed to identify potential anticancer compounds. Several indole alkaloids have shown antiproliferative effect due to different mechanisms, namely by inducing apoptosis or arresting cell cycle, in diverse cancer cell lines, including multidrug-resistant phenotypes. This review primarily aims to underscore the anticancer activity of indole and bisindole alkaloids isolated from several Tabernaemontana species. Moreover, our recent contributions to the field are also highlighted, focusing on the study of Tabernaemontana elegans. The anticancer evaluation, namely the reversion of P-glycoprotein-mediated multidrug resistance, of two sets of monoterpene indole alkaloid derivatives, obtained by modification of some functional groups of two major monoterpene indole alkaloids, is reviewed, as well as the results obtained for a derivative that targeted homologous recombination DNA repair defects.

吲哚生物碱主要存在于植物中,是一大类天然产物衍生化合物,具有显著的化学多样性和重要的生物特性。其中,萜类吲哚生物碱是次生代谢产物中最大的一类。Tabernaemontana(天胡荽科)物种广泛分布于世界热带和亚热带地区,在传统医学中用于治疗包括肿瘤在内的多种疾病。这些物种可生物合成大量结构复杂的单萜吲哚和双吲哚生物碱。鉴于吲哚生物碱具有令人信服的生物特性,人们广泛对 Tabernaemontana 树种进行植物化学研究,以确定潜在的抗癌化合物。一些吲哚生物碱通过不同的机制,即通过诱导细胞凋亡或阻止细胞周期,在不同的癌细胞系(包括耐多药表型)中显示出抗增殖作用。本综述的主要目的是强调从几种 Tabernaemontana 物种中分离出的吲哚和双吲哚生物碱的抗癌活性。此外,还着重介绍了我们最近在该领域的贡献,重点是对 Tabernaemontana elegans 的研究。综述了通过修饰两种主要单萜吲哚生物碱的一些官能团而获得的两组单萜吲哚生物碱衍生物的抗癌评价,即逆转 P 糖蛋白介导的多药耐药性,以及针对同源重组 DNA 修复缺陷的衍生物所取得的成果。
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引用次数: 0
The antibacterial potential and effects of Rhodiola sp. on gut microbiota 红景天的抗菌潜力及其对肠道微生物群的影响
IF 7.7 2区 生物学 Q1 Agricultural and Biological Sciences Pub Date : 2024-04-27 DOI: 10.1007/s11101-024-09965-5
Anja Klančnik, Ajda Kunčič, Sonja Smole Možina, Franz Bucar

The challenge of antimicrobial resistance requires new solutions, and Rhodiola sp. is a promising candidate due to its rich medicinal history. This review focuses on Rhodiola sp., especially R. rosea, highlighting its phytochemical constituents, such as salidroside, rosavins, and other phenolics, and their antimicrobial potential. We investigate the efficacy of Rhodiola sp. against various pathogenic bacteria, suggesting their value in combating antimicrobial resistance. Additionally, Rhodiola compounds are being investigated both as direct antimicrobials and as resistance modifiers that increase the efficacy of antibiotics. Rhodiola extracts and salidroside modulate gut microbiota, thereby affecting health and physiological and metabolic disorders. This illustrates the comprehensive therapeutic potential of Rhodiola sp. We emphasize the importance of understanding the complex interactions between Rhodiola phytochemicals, their antimicrobial effects, and their effects on gut microbiota as well as the need for in-depth research. Further studies will be crucial for the development of holistic treatment approaches. Finally, Rhodiola sp. is highlighted as an important natural resource in the fight against microbial pathogens and antibiotic resistance. Research on Rhodiola sp. should continue to further unravel pharmacological and health-promoting potential and thus address an important public health challenge.

抗菌药耐药性的挑战需要新的解决方案,而红景天因其丰富的药用历史而成为一个很有前景的候选品种。本综述侧重于红景天,尤其是玫瑰红景天,重点介绍其植物化学成分(如水杨梅苷、玫瑰苷和其他酚类物质)及其抗菌潜力。我们研究了红景天对各种病原菌的功效,表明其在对抗抗菌药耐药性方面的价值。此外,红景天化合物既可作为直接抗菌剂,也可作为提高抗生素疗效的抗药性调节剂,目前正在对其进行研究。红景天提取物和水杨甙可调节肠道微生物群,从而影响健康和生理代谢紊乱。我们强调了解红景天植物化学物质、其抗菌作用及其对肠道微生物群的影响之间复杂的相互作用的重要性以及深入研究的必要性。进一步的研究对于开发综合治疗方法至关重要。最后,强调红景天是对抗微生物病原体和抗生素耐药性的重要自然资源。有关红景天的研究应继续进行,以进一步揭示其药理和促进健康的潜力,从而应对重要的公共卫生挑战。
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引用次数: 0
Medicinal plants cultivated in Egypt with anticancer potential; a systematic review 埃及种植的具有抗癌潜力的药用植物;系统综述
IF 7.7 2区 生物学 Q1 Agricultural and Biological Sciences Pub Date : 2024-04-24 DOI: 10.1007/s11101-024-09957-5
Iman Abdelhady Elshnoudy, A. M. Elkhouly, Mira Masoud, Hanin A. Rabea, F. Mansour
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引用次数: 0
Secondary metabolites from cyanobacteria: source, chemistry, bioactivities, biosynthesis and total synthesis 来自蓝藻的次级代谢物:来源、化学、生物活性、生物合成和总合成
IF 7.7 2区 生物学 Q1 Agricultural and Biological Sciences Pub Date : 2024-04-22 DOI: 10.1007/s11101-024-09960-w
Yanchun He, Ying Chen, Huaming Tao, Xuefeng Zhou, Juan Liu, Yonghong Liu, Bin Yang
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引用次数: 0
Plant-derived bioactive compounds as key players in the modulation of immune-related conditions 植物生物活性化合物是调节免疫相关疾病的关键因素
IF 7.7 2区 生物学 Q1 Agricultural and Biological Sciences Pub Date : 2024-04-16 DOI: 10.1007/s11101-024-09955-7
Sara F. Vieira, Rui L. Reis, Helena Ferreira, Nuno M. Neves

The immune system is a complex and fundamental network for organism protection. A minimal unbalance in the host defense system homeostasis can originate severe repercussions in human health. Fundamentally, immune-related diseases can arise from its compromise (immunodeficiency diseases), overactivation against itself (autoimmune diseases) or harmless substances (allergies), and failure of eliminating the harmful agent (chronic inflammation). The notable advances and achievements in the immune system diseases pathophysiology have been allowing for a dramatic improvement of the available treatments. Nevertheless, they present some drawbacks, including the inappropriate benefit/risk ratio. Therefore, there is a strong and urgent need to develop effective therapeutic strategies. Nature is a valuable source of bioactive compounds that can be explored for the development of new drugs. Particularly, plants produce a broad spectrum of secondary metabolites that can be potential prototypes for innovative therapeutic agents. This review describes the immune system and the inflammatory response and examines the current knowledge of eight plants traditionally used as immunomodulatory medicines (Boswellia serrata, Echinacea purpurea, Laurus nobilis, Lavandula angustifolia, Olea europaea, Salvia officinalis, Salvia rosmarinus, and Taraxacum officinale). Moreover, the issues responsible for possible biologic readout inconsistencies (plant species, age, selected organ, developmental stage, growth conditions, geographical location, drying methods, storage conditions, solvent of extraction, and extraction method) will also be discussed. Furthermore, a detailed list of the chemical composition and the immunomodulatory mechanism of action of the bioactive compounds of the selected plant extracts are presented. This review also includes future perspectives and proposes potential new avenues for further investigation.

免疫系统是保护生物体的复杂而基本的网络。宿主防御系统平衡的微小失衡都会对人类健康造成严重影响。从根本上说,与免疫有关的疾病可能源于免疫系统受损(免疫缺陷病)、针对自身(自身免疫病)或无害物质(过敏)的过度激活,以及未能消除有害因子(慢性炎症)。在免疫系统疾病病理生理学方面取得的显著进步和成就使现有的治疗方法得到了极大的改进。然而,它们也存在一些缺点,包括效益/风险比不合适。因此,我们亟需开发有效的治疗策略。大自然是生物活性化合物的宝贵来源,可用于开发新药物。特别是,植物可产生种类繁多的次生代谢物,可作为创新治疗药物的潜在原型。本综述介绍了免疫系统和炎症反应,并考察了目前对传统上用作免疫调节药物的八种植物(蛇床子、紫锥菊、月桂、薰衣草、油橄榄、丹参、鼠尾草和蒲公英)的了解。此外,还将讨论可能导致生物读数不一致的问题(植物种类、年龄、所选器官、发育阶段、生长条件、地理位置、干燥方法、储存条件、提取溶剂和提取方法)。此外,还详细列出了所选植物提取物的化学成分和生物活性化合物的免疫调节作用机制。本综述还包括未来展望,并提出了进一步研究的潜在新途径。
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引用次数: 0
Key-enzymes involved in the biosynthesis of resveratrol-based stilbenes in Vitis spp.: a review 葡萄属植物中参与白藜芦醇类芪类化合物生物合成的关键酶:综述
IF 7.7 2区 生物学 Q1 Agricultural and Biological Sciences Pub Date : 2024-04-16 DOI: 10.1007/s11101-024-09958-4
Blandine Marant, Jérôme Crouzet, Amandine L. Flourat, Philippe Jeandet, Aziz Aziz, Eric Courot

Polyphenols are a large class of plant specialized metabolites with interesting biological properties. Among them, the stilbene phytoalexins are particularly abundant in grapevine gaining considerable applications in the cosmetic and nutraceutical industry. The well-studied stilbene biosynthetic pathway uses phenylalanine to generate resveratrol, the primary stilbene core synthetized in grapevine. A set of enzymes further metabolize resveratrol producing a diversity of stilbenes with different properties, activities and stabilities. In grapevine, 13 enzymes have been identified with the ability to use resveratrol as a substrate, including ten peroxidases, two glycosyltransferases and one O-methyltransferase. Peroxidases and methyltransferases are the most studied enzymes in grapevine, especially under stress conditions while the role of plant laccases and hydroxylases in stilbene metabolism is still poorly described. This article provides an overview of the key enzymes involved in the synthesis of resveratrol-based derivatives in Vitis spp. Perspectives to identify new enzymes are discussed, which could be further used for stilbene bioproduction using biotechnologies.

多酚是一大类具有有趣生物特性的植物特殊代谢物。其中,白藜芦醇植物毒素在葡萄中的含量尤为丰富,在化妆品和营养保健品行业的应用也相当广泛。经过深入研究的白桦烯生物合成途径利用苯丙氨酸生成白藜芦醇,这是葡萄中合成的主要白桦烯核心。一组酶进一步代谢白藜芦醇,产生具有不同性质、活性和稳定性的多种二苯乙烯。在葡萄藤中,已经发现 13 种酶能够以白藜芦醇为底物,其中包括 10 种过氧化物酶、两种糖基转移酶和一种 O-甲基转移酶。过氧化物酶和甲基转移酶是研究得最多的葡萄酶,尤其是在胁迫条件下。本文概述了葡萄属植物中参与白藜芦醇类衍生物合成的关键酶,讨论了确定新酶的前景,这些新酶可进一步利用生物技术进行二苯乙烯类生物生产。
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引用次数: 0
Technological insights into lutein isolation from marigold flower and their diverse applications: a compendious review 从万寿菊花中分离叶黄素的技术见解及其多样化应用:综述
IF 7.7 2区 生物学 Q1 Agricultural and Biological Sciences Pub Date : 2024-04-15 DOI: 10.1007/s11101-024-09959-3
Surbhi Sharma, Aushmita Das, Abha Kumari, Manju M. Gupta

In our comprehensive review, we delve into the critical steps of isolation of lutein and zeaxanthin from marigold flowers focusing on several pre-treatment technologies for marigold flower hydrolysis, non-green and green solvent-based extraction techniques of hydrolyzed solid biomass, and saponification of oleoresin while addressing the associated challenges and limitations. The review highlights the varying effects of different pre-treatments on the degradation of pectin, lignin, cellulose, and hemicellulose as well as on lutein and zeaxanthin ester yield. Notably, the enzymatic pre-treatment emerges as the most efficacious approach, despite its reliance on costly commercial enzymes. Based on the literature review, it is determined that supercritical fluid extraction, combined with ultrasound and various co-solvents gives off better yields of lutein as compared to the other extraction methods. This review also covers the saponification, purification, and recovery process. The applications of marigold flowers and lutein are also summarized.

在我们的综合综述中,我们深入探讨了从万寿菊花中分离叶黄素和玉米黄质的关键步骤,重点介绍了万寿菊花水解的几种预处理技术、水解固体生物质的非绿色和绿色溶剂萃取技术以及油脂皂化技术,同时探讨了相关的挑战和局限性。综述强调了不同预处理方法对果胶、木质素、纤维素和半纤维素降解以及叶黄素和玉米黄质酯产量的不同影响。值得注意的是,酶预处理是最有效的方法,尽管它依赖于昂贵的商业酶。根据文献综述,超临界流体萃取与超声波和各种助溶剂相结合,与其他萃取方法相比,叶黄素的产量更高。本综述还涉及皂化、纯化和回收过程。此外,还总结了万寿菊花和叶黄素的应用。
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引用次数: 0
Hordatines, dimerised hydroxycinnamoylagmatine conjugates of barley (Hordeum vulgare L.): an appraisal of the biosynthesis, chemistry, identification and bioactivities Hordatines,大麦(Hordeum vulgare L.)的二聚化羟苯甲酰拉格马汀共轭物:对生物合成、化学、鉴定和生物活性的评估
IF 7.7 2区 生物学 Q1 Agricultural and Biological Sciences Pub Date : 2024-04-09 DOI: 10.1007/s11101-024-09961-9
Claude Y. Hamany Djande, Ian A. Dubery

Hydroxycinnamoylamides are specialised metabolites widely distributed in the plant kingdom. These are phenolic moieties covalently linked to mono- or polyamines through amide bonds. Their oxidative coupling (dimerisation) leads to neolignanamides, a group of compounds showing high chemical, structural and functional diversity. Typical to barley, dehydro dimers of hydroxycinnamoylagmatines, hordatines are primarily found in germinated seeds and at the seedling stage. The first step in the biosynthesis of hordatines is catalysed by acyl-coenzyme A-dependent N-hydroxycinnamoyltransferases, and lead to the formation of hydroxycinnamoylagmatines (HCAgms). The oxidative homo- or hetero-dimerisation of the latter results in different hordatines (A, B, C or D). Hordatines can also undergo various types of conjugation and form hydroxylated, methylated or glycosylated derivatives. Although the research on the bioactivities of the hordatines is still nascent, the in planta antifungal properties have long been recognised. While hordatines are naturally and uniquely synthesised in barley plants, these molecules or lead compounds derived therefrom, also exhibit medicinal and pharmaceutical uses important for human health, stimulating research into the utilisation of biotechnology in alternative production hosts and to enhance agricultural yields and value-added production. This review summarises the older and recent knowledge about hordatines and derivatives and may serve as a springboard for future research on this intriguing class of secondary plant metabolites.

羟基肉桂酰亚胺是一种特殊的代谢物,广泛分布于植物界。它们是通过酰胺键与单胺或多胺共价连接的酚分子。它们的氧化偶联(二聚化)会产生新木犀草酰胺,这是一类具有高度化学、结构和功能多样性的化合物。以大麦为典型,羟基肉桂酰巴马汀的脱氢二聚体、霍达汀主要存在于发芽的种子和幼苗阶段。大麦芽碱生物合成的第一步是由依赖于酰基辅酶 A 的 N-羟基肉桂酰转移酶催化,形成羟基肉桂酰巴马汀(HCAgms)。后者的氧化同源或异源二聚化会产生不同的大麦芽碱(A、B、C 或 D)。大麦芽碱还会发生各种共轭作用,形成羟基化、甲基化或糖基化衍生物。尽管对大麦芽碱生物活性的研究仍处于起步阶段,但其植物抗真菌特性早已得到认可。虽然大麦碱是在大麦植物中自然合成的独特物质,但这些分子或由其衍生的先导化合物也具有对人类健康非常重要的药用和医药用途,从而促进了在替代生产主机中利用生物技术的研究,并提高了农业产量和生产附加值。本综述总结了有关大麦异黄酮及其衍生物的最新和较早的知识,可作为今后研究这类引人入胜的植物次生代谢物的跳板。
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引用次数: 0
The genus Quercus: metabolites, biological activity and mechanisms of action 柞树属:代谢物、生物活性和作用机制
IF 7.7 2区 生物学 Q1 Agricultural and Biological Sciences Pub Date : 2024-04-09 DOI: 10.1007/s11101-024-09935-x
Lulu Jiang, Shuanghui Yin, Guangyue Wang, Xinting Shao, Ye Wang, Yong Li, Yuling Ding

Quercus, an essential genus within the Fagaceae family, comprises roughly 500 plant species. Over the past 5 years (2019–2023), there has been a noticeable increase in the production of high-quality research papers focusing on this genus, marking it as an emerging research area of interest. However, despite this growing body of work, there has yet to be a comprehensive and systematic review addressing the metabolites, pharmacological effects, and underlying mechanisms associated with Quercus. To bridge this knowledge gap, the current study performed an exhaustive literature review. A total of 64 relevant papers published in high-impact journals (classified as JCR Q1–Q3) between January 2019 and April 2023 were meticulously selected through comprehensive searches of the ACS, PubMed, Web of Science, and Science Direct databases. The chemical analysis encompassed the identification of 217 compounds, spanning categories like terpenoids, flavonoids, tannins, and phenols, among others. Within this set, 11 previously undisclosed compounds emerged, comprising 6 terpenoids and 5 esters. The study primarily delved into the internal and external pharmacological properties of 23 distinct plant species, including antioxidant, antibacterial, anti-inflammatory, antidiabetic effects, and even the assessment of its potential for mitigating the impact of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). This paper offers a comprehensive evaluation of the findings and provides insightful recommendations for guiding future research on this plant genus. The ultimate aim is to facilitate a solid foundation for the modern research and development of Quercus spp., thereby contributing to scientific advancement and enhancing the existing literature in this field.

栎属是落叶松科的一个重要属种,由大约 500 种植物组成。在过去的 5 年(2019-2023 年)中,以柞树属为研究对象的高质量研究论文明显增加,这标志着柞树属已成为一个新兴的研究领域。然而,尽管研究成果越来越多,但还没有一篇全面系统的综述论述与柞树相关的代谢物、药理作用和潜在机制。为了弥补这一知识空白,本研究进行了详尽的文献综述。通过对 ACS、PubMed、Web of Science 和 Science Direct 数据库进行全面检索,精心挑选了 2019 年 1 月至 2023 年 4 月期间发表在高影响力期刊(被归类为 JCR Q1-Q3)上的 64 篇相关论文。化学分析包括 217 种化合物的鉴定,涵盖萜类、类黄酮、单宁和酚类等类别。在这组化合物中,发现了 11 种以前未曾披露的化合物,包括 6 种萜类化合物和 5 种酯类化合物。这项研究主要探讨了 23 种不同植物的内外药理特性,包括抗氧化、抗菌、抗炎、抗糖尿病作用,甚至评估了其减轻严重急性呼吸系统综合征冠状病毒 2(SARS-CoV-2)影响的潜力。本文对研究结果进行了全面评估,并为指导今后对该植物属的研究提出了有见地的建议。最终目的是为柞树属植物的现代研究和开发奠定坚实的基础,从而促进该领域的科学进步和现有文献的完善。
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引用次数: 0
A critical review on Pulicaria species occurring in Qatar: traditional uses, phytochemistry and biological activities 对卡塔尔出现的 Pulicaria 物种的重要评述:传统用途、植物化学和生物活性
IF 7.7 2区 生物学 Q1 Agricultural and Biological Sciences Pub Date : 2024-04-08 DOI: 10.1007/s11101-024-09932-0
Deepak M. Kasote, Malik Adil Nawaz, Kamal Usman, Najeeb Ullah, Mohammed Alsafran

In Qatar, three main species of Pulicaria (from Asteraceae) such as Pulicaria undulata (L.) C.A.Mey, Pulicaria gnaphalodes (Vent.) Boiss. and Pulicaria sicula (L.) Moris are reported. Traditionally, these species have almost the same ethnomedical uses, including their use as herbal tea. This could be because of morphological similarities among some of these species, which also results in taxonomic ambiguity. Altogether, this indicates that these species need to be reviewed comparatively, to understand the phytochemical uniqueness and therapeutic significance of each species individually, including species differentiation at the subspecies level. Hence, this review aims to comparatively review the available literature about traditional uses, phytochemistry, and bio-activities of these species. Being aromatic plants, the chemical composition of essential oils of these species has been extensively studied and reported over 300 volatile organic compounds. Among these, oxygenated monoterpenes and sesquiterpenes are dominant. The diverse and distinguishable composition of essential oils can differentiate P. undulata and Pulicaria crispa (Forssk.) Oliv. (Synonyme: Pulicaria undulata subsp. undulata). Likewise, flavonoids and sesquiterpenes are the most reported classes of compounds in non-essential oil fractions. Various biological and pharmacological activities are reported to the essential oils, crude extracts, and their fractions, or isolated compounds of these species. Among these, antimicrobial, anticancer, and anti-oxidant activities were mostly investigated, mainly under in vitro conditions. Several distinguishable compounds are listed for each species that can potentially be used as chemical markers while characterizing these species. Most of the traditional claims of these species are validated in recent scientific studies. However, further detailed in vivo clinical interventions are needed for their potential use as therapeutic agents.

据报道,卡塔尔有三个主要的 Pulicaria(菊科)物种,如 Pulicaria undulata (L.) C.A.Mey、Pulicaria gnaphalodes (Vent.) Boiss.和 Pulicaria sicula (L.) Moris。传统上,这些物种具有几乎相同的民族医学用途,包括用作凉茶。这可能是因为其中一些物种形态相似,也造成了分类上的模糊。总之,这表明需要对这些物种进行比较研究,以了解每个物种的植物化学独特性和治疗意义,包括在亚种水平上的物种区分。因此,本综述旨在对有关这些物种的传统用途、植物化学和生物活性的现有文献进行比较综述。作为芳香植物,这些物种的精油化学成分已被广泛研究,并报告了 300 多种挥发性有机化合物。其中,含氧单萜和倍半萜占主导地位。精油成分的多样性和可辨别性可以区分出 P. undulata 和 Pulicaria crispa (Forssk.) Oliv.(同义词:Pulicaria undulata subsp.)同样,黄酮类化合物和倍半萜是非精油馏分中报告最多的化合物类别。据报道,这些物种的精油、粗提取物及其馏分或分离化合物具有多种生物和药理活性。其中,抗菌、抗癌和抗氧化活性主要是在体外条件下进行研究的。每个物种都列出了几种可区分的化合物,这些化合物可作为化学标记来描述这些物种的特征。最近的科学研究证实了这些物种的大多数传统说法。不过,还需要进一步进行详细的体内临床干预,才能将其用作潜在的治疗药物。
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引用次数: 0
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Phytochemistry Reviews
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