New Ecdysteroids from Serratula tinctoria

Six new ecdysteroids have been isolated from SERRATULA TINCTORIA; these are: the 2,22- and 3,22-diacetates of 20-hydroxyecdysone, 5beta-hydroxyrubrosterone, 3-epi-poststerone, 3-epi-rubrosterone, and 22-oxo-20-hydroxyecdysone. These minor compounds were found together with the known ecdysteroids, 20-hydroxyecdysone, its 2-, 3-, and 22-monoacetates, rubrosterone, poststerone, polypodine B (5beta,20-dihydroxyecdysone), pterosterone (25-deoxy-20,24-dihydroxyecdysone), and makisterone C (24-ethyl-20-hydroxyecdysone). All these ecdysteroids were isolated by a combination of several chromatographic techniques (liquid chromatography on alumina, DCCC, and HPLC), then identified using standard mass spectrometric and 2D (1)H-NMR techniques.     

Phytoecdysteroids effects on mammalians,isolation and analysis

Ecdysteroids are known insect moulting hormones, regulating the insects' metamorphosis. At the same time, ecdysteroids reveal beneficial effects on humans and animals alike. Medicinal plants have been subjected to an intensive research, addressing the presence of ecdysteroids. The possible utilization of medicinal plant deals with their use as raw materials for health preparations and also for the isolation of new phytoecdysteroids. Research on the plant ecdysteroids involves two basic lines. Isolation of major compounds and scout their physiological effects; and isolation of minor ecdysteroids to find new compounds. This review summarizes the recent efforts in the ecdysteroid research including their indication as health improvement preparations, chromatography of ecdysteroids and certain methods for identification of new ecdysteroids.     

β-蜕皮甾酮的分离及结构修饰

目的从露水草总甾酮中分离β蜕皮甾酮并对其进行结构修饰。方法采用硅胶柱色谱分离β蜕皮甾酮,并以其为原料通过化学合成的各种手段合成结构类似物,利用光谱分析方法对所得化合物进行结构确证。结果与结论从露水草总甾酮中分离了β蜕皮甾酮(20 hydroxyecdysone)及另一含量较大的筋骨草甾酮C(ajugasterone C)。以分离的β蜕皮甾酮为原料化学合成了5种植物甾酮。分别是2,3,20,22双异丙叉基β蜕皮甾酮(20 hydroxyecdysone 2,3,20,22 diacetonideⅠ)、20,22异丙叉基β蜕皮甾酮(20 hydroxyecdysone 20,22 acetonideⅡ)、2,3,20,22双异丙叉基25乙酰基β蜕皮甾酮(viticosterone E 2,3,20,22 diacetonideⅢ)、2,3异丙叉基β蜕皮甾酮(20 hy-droxyecdysone 2,3 acetonideⅣ)、2,3异丙叉基22羰基β蜕皮甾酮(22 oxo 20 hydroxyecdysone2,3 acetonideⅤ)。     

Ecdysteroid sources in the Carpathian basin. 11-hydroxy substituted ecdysteroids from the Serratula wolffii Andrae

Seven ecdysteroids have been isolated from the methanolic extract of the herb Serratula wolffii Andrae. The isolation process involved the removal of polar and apolar contaminants, and also included the separation of the target ecdysteroids from each other by using combined chromatographic methods. Isolation of the pure compounds required a minimum of 2 and a maximum of 7 consecutive chromatographic steps with different selectivity. Six of the isolated ecdysteroids showed the presence of an 11alpha-hydroxyl group on the steroidal skeleton, which structure may enhance the increasing effect of ecdysteroids on the protein synthesys of mammals, according to literature data. Ajugasterone C, one of these compounds was found to be present in remarkable amount in the plant. One ecdysteroid, 11 alpha-hydroxypoststerone was identified as a new natural compound.     

Ecdysone from roots and seeds of Helleborus species

Ecdysones from Roots and Seeds of Helleborus Species From roots and seeds of Helleborus odorus WALDST. et KIT. four ecdysteroids have been isolated: β-Ecdysone (1) , 5-α-hydroxyecdysone (2) , 5-α-hydroxyecdysone 3-α-D-glucoside (3) , and 5-β-hydroxyecdysone 3-β-D-glucoside (4).     

Phytoecdysteroids--from isolation to their effects on humans

An overview is given on both well-known and recently discovered phytoecdyteroids including a sophisticated isolation scheme and notable physiological and pharmacological effects of ecdysteroids on vertebrates. The isolation of pure ecdysteroids has been improved by the use of low-pressure reversed-phase chromatography. An optimized combination of preliminary purification and chromatographic separations results in pure ecdysteroids. Structural elucidation has been done using spectroscopic methods, however, the final proof of the steric structure is rendered using x-ray crystallography. Ecdysteroid containing preparations show a boom and both OTC products and numerous preparation techniques can be found using the Internet. This paper will give a review on the kaleidoscope of pharmacological effects attributed to the ecdysteroids, such as: An increase of protein synthesis (for body-building, AIDS, patients with neoplasm disease, etc.), and other body functions; Antidepressant effect; Shielding the body from stress, and improve the physical and sexual performance; Prevention from infections and certain diseases. A list of recent offers of ecdysteroid-containing products will also be given. The perspective use of ecdysteroids is promising in genetics. Steroid regulation of programmed cell death during development and differentiation has recently come to the limelight. Murine model of human diseases and its influencing with ecdysteroids are detailed.     

New and bioactive aromatic compounds from Zanthoxylum zanthoxyloides

In the course of a study of medicinal plants from Mali, the root bark of Zanthoxylum zanthoxyloides Lam. (Rutaceae) was investigated. The root bark of this plant is used as a toothbrush by West African people. Phytochemical investigation of the MeOH extract of Zanthoxylum zanthoxyloides Lam. (Rutaceae) led to the isolation of different biologically active compounds. The separation of acetylcholinesterase inhibitors was performed by centrifugal partition chromatography (CPC). The fractions were monitored by direct TLC bioautographic assays. The bio-guided isolation led to the isolation of a new peroxide derivative. In addition, LC/UV/MS analysis performed on the crude MeOH extract allowed on-line identification of some known compounds. The structures of the isolated compounds were elucidated by classical spectroscopic methods including UV, NMR, MS and HR-MS.     

多黏菌素E类似物的纯化和结构鉴定

目的对硫酸多黏菌素中的低含量成分进行纯化和鉴定。方法利用两次反相色谱纯化制备得到单组份,并通过Nα-(2,4-二硝基-5-氟苯基)-L-丙氨酰胺(Nα-(2,4-Dinitro-5-fluorophenyl)-L-alaninamide,FDAA)试剂衍生法研究组分的组成氨基酸及其构型。基于二级质谱和氨基酸组成的结果对化合物进行了结构鉴定。结果多黏菌素E2的氨基酸组成、分子量与文献报道一致;杂质3和杂质9结构中含有L-Leu残基和羟基化的脂肪酸链;杂质6含有L-Val残基。结论杂质3、杂质6和杂质9分别为3-OHE2、Val-E2和3-OH-E1。     

Analysis of phytoecdysteroids in cultured plants of Ajuga nipponensis makino

Cultured plants of Ajuga nipponensis contained cyasterone (1), ajugasterone C (2), cyasterone-22-acetate (3) and 22-dehydrocyasterone (4) based on HPLC and NMR data, whereas 20-hydroxyecdysone was not detectable. The presence of compounds 2-4 is reported for the first time in this species. Compound 1 is the main phytoecdysteroid component found in both preblossom and blossom plants, but the latter contained higher amount than the former. Compared with other parts of the plant, the highest percentage of 1 and 3 occurred in leaves, amounting to 60.1% and 88.0% respectively, whereas the flowers contained mainly 2, which represented 72.8% of the total amount in whole plant. The contents of phytoecdysteroids in stems were very low.     

Components of Serratula species; screening for ecdysteroid and inorganic constituents of some Serratula plants]

Ecdysteroid and inorganic components were analyzed from several plant species belonging to Caryophyllaceae family, such as in the cases of Serratula tinctoria, Serratula wolffii, Serratula coronata (20-hydroxyecdysone and inorganic components) and Jurinea mollis, Serratula gmellinii and Leuzea carthamoides (inorganic components, only). The 20-hydroxyecdysone content was determined using thin-layer chromatography after a simple clean up that had been performed by solid-phase extraction. Inorganic constitutents were determined using either ICP or flame photometry. Vegetation dependence of both 20-hydroxyecdysone and inorganic elements was studied. Serratula coronata shows remarkable high 20-hydroxyecdysone (2.3%, in April) and the studied Serratula plants gave a minimum of 20-hydroxyecdysone in June. Favorable period for harvesting is suggested as July and August, through the blossoming of these plants. Potassium and 20-hydroxyecdysone content gave a similar tendency considering their vegetation dependence, while the magnesium content moved toward opposite direction. The calcium contents of Serratula tinctoria, Serratula wolffii and Serratula coronata were found between 2.2% and 3.8%, which values are high relative to the other medicinal plants. At the same time, the Cu content of the ecdysteroid producing (and screened) Caryophyllaceae plants is low. The Fe, Mn and Mg contents of Serratula coronata are high, even higher than that of the Leuzea carthamoides. Our results have suggested the importance of analysis and control of inorganic constituents of crude plant extracts used for medicinal and recreational purposes.     

Antimicrobial activity of natural ecdysteroids from Serratula coronata L. and their acyl derivatives

Natural ecdysteroids isolated from Serratula coronata L., including 20-hydroxyecdysone (20-HE), 25-S-inokosterone, and ecdysone, did not exhibit antimicrobial activity with respect to most standard test microbe cultures. The introduction of the acetyl group into the 20-HE molecule significantly increased the antibacterial activity with respect to microbes inducing inflammatory and purulent processes. Acyl derivatives of 20-hydroxyecdysone can be suggested for use in wound-healing compositions __________ Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 40, No. 5, pp. 34–36, May, 2006.     

露水草的化学成分露水草的化学成分

目的研究露水草的化学成分。 方法应用多种色谱技术进行分离，并结合NMR,MS等波谱解析确定其化学结构。结果分离得到6个化合物，鉴定为20，22-异丙叉基筋骨草甾酮C（1），20，22-异丙叉基β-蜕皮甾酮（2），22-羰基筋骨草甾酮C（3），22-羰基-β-蜕皮甾酮（4），β-谷甾醇（5），胡罗卜苷（6）。结论3为一新化合物，4为一新天然产物。     

毛脉酸模内生真菌RGT-S11菌丝体化学成分研究

研究毛脉酸模(Rumex gmelini Turcz.)内生真菌RGT-S11菌丝中的化学成分。运用溶剂萃取、硅胶柱色谱、ODS反相柱色谱、Sephadex LH-20柱色谱、制备液相等方法进行分离纯化,根据理化性质、NMR数据鉴定化合物的结构。结果:分离得到7个单体化合物:苯甲酸(Ⅰ),棕榈酸(Ⅱ),麦角甾-5,7,22-三烯-3β-醇(Ⅲ),油酸(Ⅳ),腺苷(Ⅴ),鸟苷(Ⅵ),没食子酸(Ⅶ)。以上化合物均为首次从内生真菌RGT-S11菌丝中分离得到。     

Cytotoxic triterpenoides from Alismatis Rhizoma

Four prostane-type triterpenes were isolated from a methanol extract of Alismatis Rhizoma by bioassay-guided isolation using in vitro cytotoxic assay. The compounds were identified as alisol B 23-acetate (1), alisol C 23-acetate (2), alisol B (3), alisol A 24-acetate (4) by spectroscopic methods. Amongst the compounds, alisol B (3) showed significant cytotoxicity against SK-OV3, B16-F10, and HT1080 cancer cell lines with ED50 values of 7.5, 7.5, 4.9 microg/ml, respectively.     

Analysis of Phytoecdysteroids in Cultured Plants of Ajuga Nipponensis Makino

Abstract

Cultured plants of Ajuga nipponensis contained cyasterone (1), ajugasterone C (2), cyasterone-22-acetate (3) and 22-dehydrocyasterone (4) based on HPLC and NMR data, whereas 20-hydroxyecdysone was not detectable. The presence of compounds 2–4 is reported for the first time in this species. Compound 1 is the main phytoecdysteroid component found in both preblossom and blossom plants, but the latter contained higher amount than the former. Compared with other parts of the plant, the highest percentage of 1 and 3 occurred in leaves, amounting to 60.1% and 88.0% respectively, whereas the flowers contained mainly 2, which represented 72.8% of the total amount in whole plant. The contents of phytoecdysteroids in stems were very low.     

藜的化学成分研究

目的:对黎Chenopodium L.的抗过敏活性成分进行研究。方法;利用色谱的方法分离成分,利用光谱和化学方法鉴定其化学结构。结果:从藜的种子中分离得到3个化合物,经光谱和化学分析,鉴定为28-氧-β-D-吡喃葡萄糖基-齐墩果酸-3-氧-β-D-吡喃葡萄糖醛酸甙(1)、20-羟基蜕皮酮(2)和芦丁(3)。结论:化合物1,2和3均为首次从该植物分离得到。     

The phytochemical,biological, and medicinal attributes of phytoecdysteroids: An updated review

The phytoecdysteroids (PEs) comprise a large group of biologically-active plant steroids, which have structures similar to those of insect-molting hormones. PEs are distributed in plants as secondary metabolites that offer protection against phytophagus (plant-eating) insects. When insects consume the plants containing these chemicals, they promptly molt and undergo metabolic destruction; the insects eventually die. Chemically, ecdysteroids are a group of polyhydroxylated ketosteroids that are structurally similar to androgens. The carbon skeleton of ecdysteroids is termed as cyclopentanoperhydro-phenanthrene with a β-side chain at carbon-17. The essential characteristics of ecdysteroids are a cis-(5β-H) junction of rings A and B, a 7-en-6-one chromophore, and a trans-(14α-OH) junction of rings C and D. Plants only synthesize PEs from mevalonic acid in the mevalonate pathway of the plant cell using acetyl-CoA as a precursor; the most common PE is 20-hydroxyecdysone. So far, over 400 PEs have been identified and reported, and a compilation of 166 PEs originating from 1998 has been previously reviewed. In the present review, we have summarized 212 new PEs reported between 1999 and 2019. We have also critically analyzed the biological, pharmacological, and medicinal properties of PEs to understand the full impact of these phytoconstituents in health and disease.KEY WORDS: Phytoecdysteroids, Secondary metabolites, Antioxidant, Anti-inflammatory, Antimicrobial, Antidiabetic, Anticancer activity     

藏药蒂达两种原植物的生药学鉴定

目的对藏药蒂达两种原植物獐牙菜、花锚进行系统的生药学鉴定,为其鉴别及应用提供科学依据。方法采用原植物、性状、显微、薄层鉴定的方法对两种原植物进行对比。结果獐牙菜、花锚在原植物形态、显微特征、薄层色谱图上有明显区别。结论通过原植物、性状、显微和薄层色谱图对比,能够很好地区别蒂达两种原植物。     

Identification of N1-methyl-2-pyridone-5-carboxamide and N1-methyl-4-pyridone-5-carboxamide as components in urine extracts of individuals consuming coffee

Caffeine metabolites were extracted from urine samples collected 4 h after consumption of a cup of coffee and were separated by high-performance liquid chromatography (HPLC) on a C18 (5 microm) reverse-phase column using an acetonitrile (5%), acetic acid (0.05%) solution as the mobile phase. The elution profiles indicated the constant presence of a major and a minor components eluting between the caffeine metabolites 5-acetamido-6-formyl-3-methyluracil (AFMU) and 7-methylxanthine (7X) in an approximate nine. A procedure was developed for the isolation of the major component in an apparent pure form, and the yield was 10-20 mg from 400 ml of urine. The minor component was isolated in an apparent pure form by this procedure as well, and the yield was 0.5 mg from 200 ml of urine. The average ratio of the two components in urine, UV absorption and 1H-NMR spectra of the two components, and 13C-NMR spectrum, mass spectrum and elemental analysis of the major component identified the major and minor components as N(1)-methyl-2-pyridone-5-carboxamide and N(1)-methyl-4-pyridone-5-carboxamide, respectively, two major metabolites of the vitamin niacin present in a significant amount in coffee beans. The two metabolites were present in the same average amount in urine extracts of individuals irregardless of coffee consumption. The findings are briefly discussed in relation to the nutritional sources of niacin and to current procedures for measuring amounts of the two metabolites in urine samples.     

Cancer chemopreventive activity of rotenoids from Derris trifoliata

A study of the chemical constituents of the stems of Derris trifoliata Lour. (Leguminosae) led to the isolation and identification of one new rotenoid, 6aalpha,12aalpha-12a-hydroxyelliptone ( 3), together with five other known rotenoids. In a search for novel cancer chemopreventive agents (anti-tumor promoters), we carried out a primary screening of five of the rotenoids isolated from the plant for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12- O-tetradecanoylphorbol 13-acetate (TPA) in Raji cells. The inhibitory activity of 3 was found to be equivalent to that of beta-carotene without any cytotoxicity. Deguelin ( 4) and alpha-toxicarol ( 5) exhibited a marked inhibitory effect on mouse skin tumor promotion in an in vivo two-stage carcinogenesis test. This investigation indicated that rotenoids might be valuable anti-tumor promoters.