Two new angular-type pyranocoumarins from the aerial parts of Angelica furcijuga and their synthesis from isoepoxypteryxin

Two new angular-type pyranocoumarins, namely hyuganin G (1) and hyuganin H (2), were isolated from an ethyl acetate extract of the aerial parts of Angelica furcijuga, together with three known angular-type pyranocoumarins, isoepoxypteryxin (3), isopteryxin (4), and hyuganin E (5). Assignment of the ¹H and ¹³C NMR data of 1 and 2 were achieved via analysis of the DEPT, HMQC, and HMBC spectra. The absolute configurations of 1 and 2 were determined by semi-synthesis from 3.     

Rupestrines A-D,alkaloids from the aerial parts of Corydalis rupestris

Phytochemical investigation of the dichloromethane extract of the dried aerial parts of Corydalis rupestris (Papaveraceae) resulted in the identification of four new isoquinoline alkaloids rupestrines A-D and one known isoquinoline alkaloid, namely, stylopine. The structures of these compounds were characterized by extensive spectroscopic methods including 1D- (¹H and ¹³C) and 2D NMR experiments (COSY, HSQC, HMBC, and NOESY) as well as HRESIMS analyses. In addition, the absolute configurations of rupestrines A-D were determined using modified Mosher’s method. Cytotoxic effects of alkaloids and their interaction with albumin were also investigated in this study.     

Sesquiterpenes and triterpenoids from the rhizomes of Alisma orientalis and their pancreatic lipase inhibitory activities

Five new terpenoids, including three sesquiterpenes 11-hydroxy-8-ox-alismoxide (1), 11-oxo-13-nor-alismol (2), and 1β,11-dihydroxy-β-cyperone (3), and two protostane-type triterpenoids 16β-acetoxy alisol B (4) and 16α-acetoxy alisol B (5) were isolated from the rhizomes of Alisma orientalis together with 11 known compounds. Their structures were established using 1D and 2D NMR and HRESIMS spectroscopic analyses. The isolated compounds were assayed for their inhibitory activities against pancreatic lipase. Compounds 6 and 13 showed inhibitory effects with IC₅₀ values of 64.4 and 45.5 μM, respectively.     

芍药晒干过程中有效化学成分及其抗氧化能力变化

为了解芍药根采后干燥过程中有效成分含量和抗氧化能力动态变化,采用高效液相色谱法测定芍药根在晒干过程中芍药苷、芍药内酯苷和苯甲酰基芍药苷的含量,同时测定其甲醇提取液抗氧化能力。结果显示,芍药根干燥过程中芍药苷和苯甲酰基芍药苷的含量均呈先升高后降低的变化趋势,芍药内酯苷的含量呈先下降后升高的变化趋势;晒干初期,芍药根中1,1-二苯基-2-三硝基苯肼（DPPH）自由基清除能力、抑制脂质过氧化能力和超氧阴离子清除能力均显著升高,后期显著降低,但仍然比新鲜样品有显著升高,且均与芍药苷含量呈显著正相关。因此,在干燥初期芍药启动抗干旱胁迫机制,可能通过诱导相关活性成分（如芍药苷）含量升高,增强其抗氧化能力,进而抵御干旱胁迫。     

Chemical constituents from the aerial parts of Meconopsis horridula (Papaveraceae)

Chemical investigation of the aerial parts of Meconopsis horridula led to the isolation and structural identification of nine flavonoids, two alkaloids and five terpenoids. Their structures were determined by comparison of ¹H and ¹³C NMR data with those reported in literature. The discovery of alkaloid cavidilinine (11) and two pentacyclic triterpenoids (15 and 16) from M. horridula provides evidence to support the view that Fumarioideae and Papaveroideae should be combined into a single family Papaveraceae.     

A novel polyacetylene from the aerial parts of Artemisia lactiflora

A novel polyacetylene, artemisidiyne A (1), has been isolated from the aerial parts of Artemisia lactiflora. The structure of this compound, which consists of an unprecedented skeleton, was established by comprehensive spectroscopic analysis. Furthermore, this new compound showed cytotoxic activity against HCT-8, BGC-823, and A549 tumor cell lines with IC₅₀ values of 7.5, 1.1 and 4.6 μM, respectively.     

Flavonol and iridoid glycosides of Ajuga remota aerial parts

Six flavonol glycosides characterised as myricetin 3-O-alpha-rhamnosyl-(1'-->2')-alpha-rhamnoside-3'-O-alpha-rhamnoside, 5'-O-methylmyricetin 3-O-[alpha-rhamnosyl (1'-->2')][alpha-rhamnosyl (1'-->4')]-beta -glucoside-3'-O-beta-glucoside, 5'-O-methylmyricetin 3-O-alpha-rhamnosyl (1'-->2')-alpha-rhamnoside 3'-O-beta-galactoside, kaemferol 3-O-rutinoside-7-O-rutinoside, myricetin 3-O-rutinoside-3'-O-alpha-rhamnoside, myricetin 3-O-beta-glucosyl (1'-->2')-beta-glucoside-4'-O-beta-glucoside together with two iridoid glycosides identified as 6,8-diacetylharpagide and 6,8-diacetylharpagide-1-O-beta-(3',4'-di-O-acetylglucoside) have been isolated from extract of Ajuga remota aerial parts. Also isolated from the same extract were known compounds; kaempferol 3-O-alpha-rhamnoside, quercetin 3-O-beta-glucoside, quercetin 3-O-rutinoside, 8-acetylharpagide, ajugarin I and ajugarin II.     

Xanthones from the stems of Cudrania tricuspidata and their inhibitory effects on pancreatic lipase and fat accumulation

Nine new xanthones, cudracuspixanthones I - Q (12–14, 25, 32–36), and 30 known xanthones (1–11, 15–24, 26–31, 37–39) were isolated from the stems of Cudrania tricuspidata (Moraceae). The structures of isolated compounds were established by using 1D and 2D NMR in combination with HR-TOF-MS. Xanthones from the stems of C. tricuspidata exerted pancreatic lipase inhibitory activity. In addition, cudracuspixanthone P (35), a new xanthone, reduced the fat accumulation in liver cells stimulated with fatty acids. Therefore, these compounds might be beneficial in the treatment of metabolic diseases.     

山豆根地上部分的酪氨酸酶抑制活性成分筛选研究

壮药山豆根,为豆科植物越南槐(Sophora tonkinensis)的干燥根和根茎,是非常重要的广西道地药材。为了更加合理地开发利用山豆根的地上部分,阐明其化学物质基础,该研究采用多种现代色谱分离方法对山豆根地上部分进行了系统分离,并通过现代波谱学方法对分离得到的单体化合物进行了结构鉴定,同时测试了单体化合物对酪氨酸酶的抑制活性。结果表明:(1)从山豆根地上部分分离得到10个化合物,分别为水杨酸(1)、对羟基苯甲酸(2)、木犀草素(3)、8-异戊烯基山萘酚(4)、槲皮素(5)、大豆素(6)、芒柄花素-7-O-β-D-葡萄糖苷(7)、刺芒柄花素(8)、鸢尾黄素(9)、金雀异黄素(10),所有化合物均首次从山豆根的地上部分中分离得到;(2)酪氨酸酶抑制活性的试验测试结果表明化合物4、7和9对酪氨酸酶均具有较强的抑制作用,其中化合物4的酪氨酸酶抑制活性最强,IC₅₀值为(1.58 ± 0.31)× 10^-5 mol·L^-1。该研究丰富了山豆根地上部分的化学物质基础及其生物活性,为山豆根非药用部位的深入开发利用奠定了基础。     

药囊花茎叶的化学成分研究

药囊花（Cyphotheca montana Diels）茎叶的乙醇提取物具有抗菌活性,进一步的活性追踪表明活性成分在乙酸乙酯和正丁醇萃取物中,我们从这两种萃取物中共分离鉴定出9个化合物,其结构通过波谱分析等分别鉴定为：槲皮素-3-O-α-L-鼠李糖甙（1）,杨梅素-3-O-α-L鼠李糖甙（2）,山萘酚-3-（2″,6″-二-O-（E）-p-羟基苯丙烯酰-β-D-吡喃葡萄糖甙（3）,3,3′-O-二甲基逆没食子酸-4-O-β-D-吡喃葡萄糖甙（4）,槲皮素（5）,2α,3β,19α,23-四羧基乌苏-12-烯-28-酸-28-0-β-D吡喃葡萄糖甙（6）,乌苏酸（7）,β-谷甾醇（8）和胡萝卜甙（9）,这些化合物均为首次从我国该特有单种属植物中分离得到。     

Cryopreservation of somatic embryos of the herbaceous peony (Paeonia lactiflora Pall.) by air drying

This study was carried out to establish a suitable method for the cryopreservation of somatic embryos of the herbaceous peony. The somatic embryos were obtained from cotyledon and anther cultures on a MS medium supplemented with abscisic acid (ABA) and phenylacetic acid (PAA), respectively. The frequency of somatic embryo formation was the greatest (61%) from the cotyledons cultured on a MS medium supplemented with 1.0 mg l(-1) of ABA. Embryos were also obtained directly from anthers cultured on a MS medium with or without 2.0 mg l(-1) of PAA. For the cryopreservation of peony somatic embryos, the embryos were dried under a stream of sterile air and frozen by immersion in liquid nitrogen. Thawed embryos were germinated into plantlets after placing on a medium containing 0.3 mg l(-1) of gibberellic acid (GA(3)). The frequency of the post-thaw regrowth of cryopreserved somatic embryos was related to their size and desiccation time, the latter ranging from 0 to 2 h. When the somatic embryos were desiccated for 1 h, the frequency of post-thaw regrowth was greater than 66%. The frequency of post-thaw regrowth of the cryopreserved somatic embryos from anthers and cotyledon tissues was generally high when they were 2-3 mm in size. Desiccation may be a suitable method for the cryopreservation of somatic embryos of the herbaceous peony.     

Chemical constituents from the aerial parts of Ajania fruticulosa

The isolation and identification of sixteen compounds extracted from the aerial parts of A. fruticulosa have been reported in the present study, including eight flavonoids (1, 2, 3, 4, 5, 6, 7 and 8), three terpenoids (9, 10 and 11), two sterols (12 and 13), one lignan (14), one fatty acid (15) and one fatty acid ethyl ester (16), wherein six compounds (2, 3, 4, 5, 10 and 14) have been isolated from A. fruticulosa for the first time. Furthermore, among the identified compounds, three compounds (6, 7 and 11) have also been reported for the first time in the genus Ajanin and three compounds (8, 15 and 16) have not been isolated and reported from other plants of the family Asteraceae. In addition, the chemotaxonomic significance of these compounds was discussed.     

Enzyme inhibition and radical scavenging activities of aerial parts of Paeonia emodi Wall. (Paeoniaceae)

The ethanolic extract derived from aerial parts of an indigenous medicinal plant Paeonia emodi was screened for enzyme inhibition activities against Urease (jack bean and Bacillus pasteurii) and α-Chymotrypsin. The extract was also investigated for its radical scavenging activity using DPPH assay. The crude extract was found to possess significant enzyme inhibition activities against jack bean (74%) and Bacillus pasteurii (80%) urease and a moderate activity (54%) against α-Chymotrypsin. The extract also displayed excellent (83%) radical scavenging activity. On the basis of these results, the crude extract was subsequently fractionated into n-hexane, chloroform, ethyl acetate, n-butanol and water fractions and tested independently for the aforesaid activities. Significant inhibitory activity against urease enzyme was observed for the ethyl acetate, n-butanol and water fractions while the n-hexane and chloroform fractions were devoid of any such activity. In the α-Chymotrypsin enzyme inhibition studies the activity was concentrated into the ethyl acetate fraction. All the fractions displayed potent radical scavenging activity. The crude extract and fractions thereof were also subjected to total phenolic content determination. A correlation between radical scavenging capacities of extracts and total phenolic content was observed in the majority of cases.     

Lipophilic constituents from aerial and root parts of Mercurialis perennis L.

Introduction – Dog's mercury (Mercurialis perennis L.) is a perennial herb used in remedies for medicinal purposes. The plant is supposed to contain potentially active substances but its constituents have only been rarely studied. Objective – Detailed studies on the phytochemical composition are of great interest to broaden the knowledge on the chemotaxonomy and pharmacognosy of M. perennis. Methodology – Chloroform and hexane extracts from roots and aerial parts were investigated using GC/MS and LC/MS. Results – The whole plant exhihited a broad spectrum of structurally diverse constituents, mainly alkaloids, terpenes, sterols and simple aromatic compounds. Closer inspection of the piperidine alkaloid hermidin revealed its inherent instability towards air oxygen. To obtain quantitative data on these alkaloids the synthesis of the more stable reference compound 4‐methoxy‐1‐methylpyridine‐2,6(1H,3H)‐dione (MMPD) was required. In this study, MMPD was detected for the first time as a genuine compound in Mercurialis. Hermidine quinone and hermidin dimers originating from hermidin via a free anionic radical reaction were also confirmed by GC/MS. Moreover, volatile compounds such as benzylalcohol, 2‐phenylethanol, 4‐methoxy‐ and 3,4‐dimethoxyphenol, (?)‐cis‐ and (+)‐trans‐myrtanol, (?)‐cis‐myrtanal as well as squalene were predominantely present in Mercurialis roots. In contrast, aerial parts mainly contained phytol derivatives, sterols and tocopherols. By changing solvent polarity, lipid and wax‐containing fractions were obtained. LC/MS‐studies on hexane extracts showed the presence of several mixed triglycerides constituted by linolenic, linoleic, oleic, stearic and palmitic acids, as well as lutein, carotenes and pheophytins. Conclusions – The phytochemical data presented complement our knowledge on the rarely studied plant M. perennis and may broaden its use in future phytotherapy. Copyright © 2009 John Wiley & Sons, Ltd.     

Evaluation of the inhibitory potential of five squaric acid derivatives against pancreatic lipase

A series of 4-alkylamino-2-ethoxycyclobut-3en-1,2-diones has been synthesized, characterized and their inhibitory effect on pancreatic lipase (PL) was evaluated. The compound 1 has shown relatively high potency (IC₅₀?=?0.11?mM) compared with the most effective anti-obesity drug, tetrahydrolipstatin (Orlistat) (IC₅₀ value?=?0.08?mM). The compounds have showed good selectivity toward PL and did not affect the activity of trypsin, another digestive enzyme.     

Chemical constituents from Anemone vitifolia Buch.-Ham. (Ranunculaceae)

A phytochemical investigation of Anemone vitifolia (Buch.-Ham.) led to the isolation of twelve compounds, including six lignans (1–6), four benzoic acid esters (7–10), one norsesquiterpenoid (11) and one lactone (12). The structures of these metabolites were established on the basis of detailed spectroscopic analysis, as well as comparisons with the data available in the literature. Among them, compounds 10 (dimethyl 2-(benzoyloxy)succinate) and 12 (4-hydroxy-5-methyl-γ-butyrolactone) were isolated for the first time as natural products. Compounds 1 and 11, compounds 2, 3, 5–7 and 9, and compounds 4 and 8 were isolated for the first time in family Ranunculaceae, genus Anemone and A. vitifolia respectively. The chemotaxonomic significance of the isolated compounds was discussed.     

Chemical constituents from the aerial parts of Impatiens hypophylla Makino var. hypophylla

Seven flavonoids such as luteolin (1), luteolin 7-O-β-glucopyranoside (2), luteolin 3'-O-β-glucopyranoside (3), chryseriol (4), apigenin (5), apigenin 7-O-β-glucopyranoside (6) and astragalin (7) and one coumarin, scopoletin (8) were isolated from the aerial parts of Impatiens hypophylla Makino var. hypophylla (Family: Balsaminaceae). Structures of these compounds were elucidated on the basis of spectroscopic methods. All these compounds were isolated for the first time from I. hypophylla var. hypophylla.     

Cytotoxic and antimalarial constituents from aerial parts of Sphaeranthus indicus

Two new eudesmanolide type sesquiterpenes, indicusalactone (1) and (⿿)⿿-⿿oxyfrullanolide (2), along with twelve known compounds (3⿿14), were isolated from the aerial parts of Sphaeranthus indicus. The structures of these compounds were established on the basis of their 1D and 2D NMR spectroscopic data. Compounds 1⿿4 and 12⿿14 showed antimalarial activity against Plasmodium falciparum with IC₅₀ values ranging from 2.32 to 6.47μg/mL. In addition, compounds 2⿿5 showed cytotoxicity against cancer cell lines, KB, NCI-H187 and MCF-7 with IC₅₀ values within the range 1.23⿿46.19 μg/mL.     

6-Methoxyflavonols from the aerial parts of Tetragonia tetragonoides (Pall.) Kuntze and their anti-inflammatory activity

Dried aerial parts of Tetragonia tetragonoides were extracted with 70% EtOH, and the evaporated residue was successively separated into EtOAc, n-BuOH, and H₂O fractions. As a result of repeated SiO₂, ODS, and Sephadex LH-20 column chromatography, four new 6-methoxyflavonol glycosides (2–4, 8) along with four known ones (1, 5–7) were isolated. Several spectroscopic data led to determination of chemical structures for four new 6-methoxyflavonol glycosides (2–4, 8) and four known ones, 6-methoxykaempferol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl-7-O-(6‴′-(E)-caffeoyl)-β-d-glucopyranoside (1), 6-methoxyquercetin (5), 6-methoxykaempferol (6), and 6-methoxykaempferol 7-O-β-d-glucopyranoside (7). Methoxyflavonol glycosides 2–8 also have never been reported from T. tetragonoides in this study. 6-Methoxyflavonols 5 and 6 showed high radical scavenging potential in DPPH and ABTS test. Also, all compounds showed significant anti-inflammatory activities such as reduction of NO and PGE₂ formation and suppression of TNF-α, IL-6, IL-1β, iNOS, and COX-2 expression in LPS-stimulated RAW 264.7 macrophages. In general, the aglycones exhibited higher activity than the glycosides. In addition, quantitative analysis of 6-methoxyflavonols in the T. tetragonoides aerial parts extract was conducted through HPLC.     

Two new compounds from the aerial parts of Elsholtzia densa

Two new compounds, named edensa acid (1), and edensaoside A (2), as well as twenty-nine known compounds (3–31) were isolated from the aerial parts of Elsholtzia densa Benth. The chemical structures of the new compounds were determined by spectrometric data interpretation using NMR, HRESIMS, IR and UV spectroscopy. In addition, all compounds were evaluated for their anti-influenza virus activities against A/WSN/33(H1N1). Among these, compounds 18 and 19 exhibited moderate anti-influenza virus activities with IC₅₀ values of 18.79 μM and 59.87 μM respectively.