Phytotoxicity of Secondary Metabolites Isolated from Flourensia oolepis S.F.Blake

The aim of this study was to isolate the active principles of Flourensia oolepis S.F.Blake (Asteraceae), which completely inhibited the germination of Raphanus sativus seeds at 10 mg/ml. Flavanone pinocembrin and sesquiterpene ilicol, were isolated by bioassay‐guided fractionation. They were active both against monocot and dicot seeds. Pinocembrin was the most active compound, with an IC₅₀(germination) value of 0.24, 3.40, 3.28, and 3.55 mM against Panicum miliaceum, Avena sativa, Lactuca sativa, and R. sativus, respectively; ilicol, however, exhibited IC₅₀(germination) values of 0.67, 2.73, 5.25, and 9.66 mM for the same species, respectively. Pinocembrin and ilicol inhibited root growth and showed IC₅₀(root growth) values of 0.199, 14.68, 8.05, 7.69 mM , and 1.22, 2.90, 7.35, 8.07 mM , against P. miliaceum, A. sativa, L. sativa, and R. sativus, respectively. Pinocembrin and ilicol reduced Allium cepa cell division without chromosome aberrations.     

不同番茄种质叶表次生代谢物质

多毛番茄(Solanum habrochaites)为重要的番茄种质资源, 其叶表存在大量次生代谢物质, 对多种虫害具有趋避或/和毒害作用。利用气相色谱-质谱联用(GC-MS)技术分析栽培番茄(S. lycopersicum ) 9706与3份多毛番茄(LA2329、LA1777和PI134417)材料叶表次生代谢物质。结果表明, 3份多毛番茄叶表可检测到的次生代谢物质种类和总含量均高于普通番茄, 同时多毛番茄亚种间次生代谢物质的种类和含量也存在差异。普通番茄叶表次生代谢物质为3种单萜和3种倍半萜类物质, 其中单萜和倍半萜类物质分别占次生代谢物质总量的60.3%和39.7%。多毛番茄LA2329和LA1777叶表倍半萜类物质的种类和含量较高, 有些萜类物质具有物种特异性。如LA2329中含量最高的α-姜烯, 其含量为2 409.1 μg·g^–1; LA1777中含量较高的γ-榄香烯和E-β-法尼烯, 含量分别为573.3 μg·g^–1和289.9 μg·g^–1, 在其它番茄材料中未检测到这3种倍半萜类物质。PI134417中含量最高的是月桂酸乙酯, 其含量为5 312.8 μg·g^–1, 在普通番茄中这一物质未见报道。PI134417中甲基酮类物质含量也较高, 其中2-十一烷酮和2-十三烷酮的含量分别为689.8 μg·g^–1和1 459.7 μg·g^–1。研究结果可为番茄种质资源利用和次生代谢物质开发提供理论依据。     

Anticancer Secondary Metabolites: From Ethnopharmacology and Identification in Native Complexes to Biotechnological Studies in Species of Genus Astragalus L. and Gloriosa L.

Some of the most effective anticancer compounds are still derived from plants since the chemical synthesis of chiral molecules is not economically efficient. Rapid discovery of lead compounds with pronounced biological activity is essential for the successful development of novel drug candidates. This work aims to present the chemical diversity of antitumor bioactive compounds and biotechnological approaches as alternative production and sustainable plant biodiversity conservation. Astragalus spp., (Fabaceae) and Gloriosa spp. (Liliaceae) are selected as research objects within this review because they are known for their anticancer activity, because they represent two of the largest families respectively in dicots and monocots, and also because many of the medicinally important plants are rare and endangered. We summarized the ethnobotanical data concerning their anticancer application, highlighted the diversity of their secondary metabolites possessing anticancer properties such as saponins, flavonoids, and alkaloids, and revealed the potential of the in vitro cultures as an alternative way of their production. Since the natural supply is limited, it is important to explore the possibility of employing plant cell or organ in vitro cultures for the biotechnological production of these compounds as an alternative.     

土壤放线菌Streptomyces sp．2215代谢物的分离鉴定及抗肿瘤活性研究

土壤来源的放线菌Streptomyces sp.2215 经发酵罐发酵,培养液经乙酸乙酯提取,硅胶柱层析、C18反相色谱、Sephadex LH-20、及TLC 和HPLC分离纯化得到四个化合物,并通过理化性质,IR,FAB-MS,1H,13C NMR,1H-1HCOSY,HSQC,HMBC等鉴定为单亚砜棘霉素(monosulfoxide quinomycine,1)、棘霉素(echinomycin,2)、喹喔啉-2-羧酸(3)、十六烷酸(4).其中化合物1、2经MTT法测定体外对K562细胞具有抑制活性,其IC50值分别为34.0、1.5 ng/mL.     

Chloroform Extract of Underground Parts of Ferula heuffelii: Secondary Metabolites and Spasmolytic Activity

Plants from the genus Ferula L. (Apiaceae) were used for various purposes in traditional medicine of different nations throughout the history. Ferula heuffelii Griseb . ex Heuffel is a perennial species endemic for Balkan peninsula. Ten compounds which belong to classes of prenyl‐furocoumarin‐, prenyl‐dihydrofurochromone‐, prenyl‐benzoyl‐ and prenyl‐benzoylfuranone‐type sesquiterpenoids, as well as sesquiterpene coumarins and phenylpropanoids, were, for the first time, isolated from the CHCl₃ extract of the underground parts of this plant and identified. Furthermore, extract and three isolated compounds, i.e., latifolone ( 1 ), dshamirone ( 4 ), and (2S*,3R*)‐2‐[(3E)‐4,8‐dimethylnona‐3,7‐dien‐1‐yl]‐2,3‐dihydro‐7‐hydroxy‐2,3‐dimethylfuro[3,2‐c]coumarin ( 6 ) were, for the first time, evaluated for their in vitro antispasmodic activities in three experimental models: spontaneous contraction, and ACh‐ and KCl‐induced contraction of an isolated rat ileum. The extract (0.1–1.3 mg/ml) and compound 6 (1–10 μg/ml) exhibited dose‐dependent effect in all three models. Compound 1 (1–6 μg/ml) affected spontaneous contractions and those induced by KCl, while compound 4 (8 μg/ml) displayed only moderate activity with ACh‐induced contractions. It can be concluded that tested compounds contribute to exhibited antispasmodic activity of crude extract. Additionally, extract (0.1–1.3 mg/ml) was tested for in vitro relaxant activity on an isolated rat trachea, and relaxed the KCl‐induced contractions in a dose‐dependent manner.     

Salinity-Induced Attenuation in Secondary Metabolites Profile and Herbicidal Potential of Brassica nigra L. on Anagallis arvensis L.

Studies on plant defense mechanisms in stressful conditions predict that plant cope up with increasing stress for survival. Under environmental stress plants interact with problems like competition and survival under resource constraints or utilization of these resources in production of secondary compounds. In this experiment, we examined the costs of defense by evaluating variation in production of secondary compounds of Brassica nigra grown in the saline (B1?=?100 mM NaCl and B2?=?150 mM NaCl) and control (C?=?0 mM) soils and impact of its extracts on weed Anagallis arvensis L. The main allelopathic compounds in Brassica were determined using gas chromatography–mass spectroscopy (GC–MS). The results indicated that A. arvensis was adversely affected by the aqueous extracts of B. nigra. These observations might be related to extracts induced oxidative stress indicated by superoxide (O₂^?) production through nitroblue tetrazolium, cell integrity by Evans blue staining, malondialdehyde estimation by Schiff reagent, lipid peroxidation, lignin deposition, and antioxidant enzyme activities assay. We observed that soil salinity reduced the phytotoxicity of aqueous extract and decreased its potential. The presence of different bioactive compounds improved the natural herbicidal properties of B. nigra and it can be used in various medicinal and agricultural practices.

     

Elicitation Improves the Leaf Area,Enzymatic Activities,Antioxidant Activity and Content of Secondary Metabolites in Achillea millefolium L. Grown in the Field

Salicylic acid (SA) is a plant hormone that stimulates the growth and metabolism of plants, also acting as an abiotic elicitor. This study aimed to evaluate the effect of SA on leaf production, leaf area and synthesis of secondary compounds in yarrow plants. The experiments were conducted under field conditions in two consecutive years and f-received SA foliar applications (T1-control; T2-1.0 mmol L⁻¹ applications at 20, 60 and 100 days after planting (DAP) and T3-1.0 mmol L⁻¹ applications at 100 DAP during 3 days). The exogenous application of SA resulted in increases in leaf area (total and specific), number of leaves and leaf mass ratio of yarrow plants, polyphenolic compounds, phenylalanine ammonia-lyase and chalcone synthase enzymes and the antioxidant activity of the plant extract. The HPLC–DAD–MS/MS analysis of phenolic compounds revealed increases in the amounts of quinic acid and rutin. The results of this research lead us to affirm that SA exerted both the hormonal effect on number of leaves and leaf area, and also acted as eliciting substance.

     

滇牡丹内生真菌PR20的鉴定及次生代谢产物的研究

根据形态学特征和18S rDNA序列分析,将滇牡丹根中分离得到的内生真菌菌株PR20鉴定为高大毛壳Chaetomium elatum。利用柱色谱层析方法从该菌株的发酵产物中分离到5个化合物,通过理化性质及波谱数据分析,分别鉴定为7-羟基-4,6二甲基苯酞(1)、苔黑酚(2)、苔色酸(3)、间羟基苯甲酸(4)和次黄嘌呤核苷(5),以上化合物均为首次从滇牡丹内生真菌中分离获得。     

Identification and Biological Evaluation of Secondary Metabolites from the Endolichenic Fungus Aspergillus versicolor

A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F–H ( 1 – 3 , resp.) and 3‐methoxyviolaceol‐II ( 4 ), eight new bisabolane sesquiterpenoids, named (?)‐(R)‐cyclo‐hydroxysydonic acid ( 5 ), (?)‐(7S,8R)‐8‐hydroxysydowic acid ( 6 ), (?)‐(7R,10S)‐10‐hydroxysydowic acid ( 7 ), (?)‐(7R,10R)‐iso‐10‐hydroxysydowic acid ( 8 ), (?)‐12‐acetoxy‐1‐deoxysydonic acid ( 9 ), (?)‐12‐acetoxysydonic acid ( 10 ), (?)‐12‐hydroxysydonic acid ( 11 ), and (?)‐(R)‐11‐dehydrosydonic acid ( 12 ), two new tris(pyrogallol ethers), named sydowiols D ( 13 ) and E ( 14 ), and fifteen known compounds, 15 – 29 . All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans, and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA‐MB‐231, and HEPG2 were also evaluated.     

地衣次生代谢产物及其生物活性研究进展

地衣是一类独特的生物有机体,其体内合成了多种特殊的次生代谢产物,主要为缩酚酸、缩酚酸环醚、缩酚酮、二苯并呋喃等类化合物。这些次生代谢产物具有多样的生物活性,包括抗氧化、抗辐射、抗菌、抗病毒、抗肿瘤、植物生长抑制和昆虫拒食等活性。本文对近40年来有关地衣化学及生物活性方面的研究进行综述,为地衣资源的进一步研究和开发提供参考。     

Tissue-Specific Distribution of Secondary Metabolites in Rapeseed (Brassica napus L.)

Four different parts, hypocotyl and radicle (HR), inner cotyledon (IC), outer cotyledon (OC), seed coat and endosperm (SE), were sampled from mature rapeseed (Brassica napus L.) by laser microdissection. Subsequently, major secondary metabolites, glucosinolates and sinapine, as well as three minor ones, a cyclic spermidine conjugate and two flavonoids, representing different compound categories, were qualified and quantified in dissected samples by high-performance liquid chromatography with diode array detection and mass spectrometry. No qualitative and quantitative difference of glucosinolates and sinapine was detected in embryo tissues (HR, IC and OC). On the other hand, the three minor compounds were observed to be distributed unevenly in different rapeseed tissues. The hypothetic biological functions of the distribution patterns of different secondary metabolites in rapeseed are discussed.     

极端环境放线菌TRM45037鉴定及次生代谢产物分析

为了明确新疆罗布泊极端环境放线菌TRM45037的分类,挖掘其次生代谢产物及其生物活性,本研究通过形态学观察、生物学特征和16S rDNA序列分析等方法,确定TRM45037为中度嗜盐性拟诺卡氏菌,与菌株Nocardiopsis dassonvilei subsp. dassonvillei DSM 4311(T) 的相似度为99.2%。采用硅胶柱色谱、凝胶柱色谱和高效液相色谱等方法对次生代谢产物进行了分离纯化,并通过核磁共振谱（1H NMR,13C NMR）结合相关文献确定化合物结构。从TRM45037发酵液中分离出4个化合物,分别鉴定为3, 4-二氢-6, 8-二羟基-3-甲基异香豆素、2-甲基-1, 4-苯二醇、邻苯二甲酸（2-乙基己基）二酯和1, 6-二羟基吩嗪。抑菌活性测定表明, 3, 4-二氢-6, 8-二羟基-3-甲基异香豆素和2-甲基-1, 4-苯二醇对金黄色葡萄球菌具有抑制作用,其最小抑菌浓度(minimal inhibitory concentration, MIC)值分别为0.78 mg/mL和0.39 mg/mL,最小杀菌浓度(minimum fugicide concentration, MFC)值分别为1.56 mg/mL和0.78 mg/mL。本研究结果可为嗜盐放线菌活性次生代谢产物挖掘提供理论依据,对新疆极端环境放线菌资源保护与利用具有切实意义。     

Secondary Metabolites,Glandular Trichomes and Biological Activity of Sideritis montana L. subsp. montana from Central Italy

Sideritis montana subsp. montana is a small annual herb occurring in countries bordering the Mediterranean and Balkan regions. The secondary metabolism of this plant has not been fully explored so far. The aim of the present study was to understand the complex mixture of secondary metabolites and the type of secretory structures. The polar constituents were isolated by column chromatography from the ethanolic extract, and their structure was elucidated by NMR and MS. The essential oil was isolated by hydrodistillation and analysed by GC/MS. The plant indumentum was studied by light and scanning electron microscopy. To complete the work, the essential oil antioxidant activity and cytotoxicity on tumor cells were evaluated by DPPH, ABTS, FRAP, and MTT methods. Four different classes of secondary metabolites were isolated, namely flavonoids, caffeoylquinic derivatives, glycosidic hydroquinones and iridoids. The essential oil was mainly characterized by sesquiterpenene hydrocarbons. Peltate and long‐capitate hairs were the main sites where terpenes and polar constituents are produced. The secondary metabolites found in S. montana subsp. montana are of chemotaxonomic interest, some of them being typical of the genus Sideritis. The trichomes types observed partially differ from those described in other members of the genus Sideritis. The essential oil showed noteworthy inhibition on tumor cells.     

绿茶水提物中主要次生代谢产物的分离纯化与结构鉴定

根据加工过程的不同,茶叶可以分为不发酵茶、半发酵茶、全发酵茶。绿茶是典型的不发酵茶,加工过程中,由于高温湿热作用,破坏了茶叶中酶的活性,阻止了茶叶中主要成分的酶性氧化,因此绿茶中含有丰富的次生代谢产物,这些物质不仅赋予了茶叶独有的色、香、味品质,而且与人体健康密切相关。为了建立绿茶水提物中主要次生代谢产物的化合物标准库,本文利用Amberlite XAD-2大孔吸附树脂、硅胶柱色谱及Sephadex LH-20凝胶柱色谱分离技术对绿茶水提物中的主要次生代谢产物进行了系统的分离纯化,采用质谱、核磁共振波谱对分离得到的化合物进行了结构鉴定。从绿茶的水提物中分离鉴定了8个化合物,分别是咖啡碱、儿茶素没食子酸酯、表儿茶素、3,5-二羟基-4-甲氧基苯甲酸、山柰酚-3-葡萄糖苷、没食子儿茶素没食子酸酯、儿茶素和没食子酸。     

海洋真菌Fusarium sp.次级代谢产物的研究

采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱、开放ODS柱色谱以及HPLC等方法从海洋真菌Fusarium sp.的菌丝体中分离得到5个化合物,通过波谱数据及理化性质分别鉴定为3β,15β-二羟基-(22E,24R)-麦角甾-5,8(14),22-三烯-7-酮(1)、3β,5α,9α-三羟基-(22E,24R)-麦角甾-7,22-二烯-6-酮(2)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β-三醇(3)、5α,8α-过氧-(22E,24R)-麦角甾-6,22-二烯-3β-醇(4)和丁二酸(5).其中化合物1和2首次从该属真菌中分离得到.     

Unusual Secondary Metabolites from Astragalus halicacabus Lam.

From the whole plant of Astragalus halicacabus (Sect. Halicacabus), a new cycloartane‐type glycoside, (20R,24S)‐3‐O‐[α‐L ‐arabinopyranosyl‐(1→2)‐β‐D ‐xylopyranosyl]‐20,24‐epoxy‐16‐O‐β‐D ‐glucopyranosyl‐3β,6α,16β,25‐tetrahydroxycycloartane, and a new glycoside, 3‐O‐[β‐D ‐apiofuranosyl‐(1→2)‐β‐D ‐glucopyranosyl]maltol were isolated together with seven known cycloartane‐type glycosides, i.e., cyclocanthoside D, askendosides D, F, and G, cyclosieversioside G, cyclostipuloside A, elongatoside, and a known maltol glucoside, 3‐O‐β‐D ‐glucopyranosylmaltol. The structures were elucidated by means of high‐resolution mass spectrometry, and extensive 1D‐ and 2D‐NMR spectroscopic analysis. This is the first phytochemical work on A. halicacabus, and a maltol glycoside was encountered for the first time in the Leguminosae family.     

江西青霉的次生代谢产物研究

江西青霉是药用江西虫草的无性型,本文对江西青霉发酵菌丝体甲醇提取物的正丁醇萃取部位运用反复色谱层析进行了系统的分离纯化,得到了6个化合物。经波谱解析,并结合理化鉴定,确定这6个化合物结构为尿嘧啶(1)2、’-脱氧尿嘧啶核苷(2)、腺嘌呤(3)、腺苷(4)、L-焦谷氨酸甲酯(5)和2’-甲氧基腺苷(6)。其中化合物2、5和6为首次从虫草属中分离获得的化合物。     

Identification of Gene-Specific Polymorphisms and Association with Capsaicin Pathway Metabolites in Capsicum annuum L. Collections

Pepper (Capsicum annuum L.) is an economically important crop with added nutritional value. Production of capsaicin is an important quantitative trait with high environmental variance, so the development of markers regulating capsaicinoid accumulation is important for pepper breeding programs. In this study, we performed association mapping at the gene level to identify single nucleotide polymorphisms (SNPs) associated with capsaicin pathway metabolites in a diverse Capsicum annuum collection during two seasons. The genes Pun1, CCR, KAS and HCT were sequenced and matched with the whole-genome sequence draft of pepper to identify SNP locations and for further characterization. The identified SNPs for each gene underwent candidate gene association mapping. Association mapping results revealed Pun1 as a key regulator of major metabolites in the capsaicin pathway mainly affecting capsaicinoids and precursors for acyl moieties of capsaicinoids. Six different SNPs in the promoter sequence of Pun1 were found associated with capsaicin in plants from both seasons. Our results support that CCR is an important control point for the flux of p-coumaric acid to specific biosynthesis pathways. KAS was found to regulate the major precursors for acyl moieties of capsaicinoids and may play a key role in capsaicinoid production. Candidate gene association mapping of Pun1 suggested that the accumulation of capsaicinoids depends on the expression of Pun1, as revealed by the most important associated SNPs found in the promoter region of Pun1.     

Regeneration of plantlets in Sapindus trifoiatus L

Continuous production of healthy plantlets of Sapindus trifoliatus L. was achieved via somatic embryos from long term cultures of an embryogenic mass (EM). A highly embryogenic culture of S. trifoliatus L. was obtained by recurrent embryogenesis from somatic embryos cultured on Murashige and Skoog's (MS) medium supplemented with kinetin (2.3 microM) and benzyladenine (8.8 microM). The cultures could be maintained without reduction of embryogenic competence for more than 20 months by subculture at 4 week intervals. About 90% mature somatic embryos on transfer to basal MS medium, germinated to plantlets, of which more than 70% survived when transferred to a sand and soil mixture in green house.     

内生真菌香柱菌及其次级代谢

两千年以前人们就已经知道一些牧草对牲畜等动物有毒。 1 90 4年Ｆｒｅｅｍａｎ从这些牧草中分离到了一类内生真菌 ,后被称为Ｎｅｏｔｙｐｈｏｄｉｕｍｏｃｃｕｌｔａｎｓ,人们才知晓造成这些动物中毒的真正元凶恰恰是这类微生物[1] 。在 2 0世纪 30年代 ,Ｓａｍｐｓｏｎ对一些植物的内生真菌作了比较性研究[2 ] ,这些内生真菌包括Ｎｅ ｏｔｙｐｈｏｄｉｕｍｌｏｉｉ和香柱菌属 (Ｅｐｉｃｈｌｏｅ)的一些种 ,其中香柱菌可以导致一些草类干死病 (ｃｈｏｋｅ)。而在大多数情况下 ,香柱菌及其相关的内生真菌长期生存于它们的宿主植物中 ,并不使…