Anti‐complement activity of isolated compounds from the roots of Clerodendrum bungei Steud.

To determine the anti‐complement activity of natural diterpenes, chromatographic separation of the acetone‐soluble fraction from the roots of Clerodendrum bungei (Verbenaceae) led to the isolation of five diterpenoids. An acetone‐soluble extract of the roots of C. bungei exhibited significant anti‐complement activity on the classical pathway complement system, which was expressed as total hemolytic activity. Five compounds isolated from the roots of C. bungei, namely 12‐O‐β‐d ‐glucopyranosyl‐3,11,16‐trihydroxyabieta‐8,11,13‐triene (1), 3,12‐O‐β‐d ‐diglucopyranosyl‐11,16‐dihydroxyabieta‐8,11,13‐triene (2), ajugaside A (3), uncinatone (4) and 19‐hydroxyteuvincenone F (5). Compounds 1, 2, 3, 4 and 5 showed inhibitory activity against complement system with 50% inhibitory concentrations (IC₅₀) values of 24 µm , 138 µm , 116 µm , 87 µm and 232 µm . Among the compounds tested, 1 showed the most potent anti‐complement activity (IC₅₀, 24 µm ). Copyright © 2010 John Wiley & Sons, Ltd.     

Anti‐inflammatory effects of chemical components from Ginkgo biloba L. male flowers on lipopolysaccharide‐stimulated RAW264.7 macrophages

Ginkgo biloba L., well known as living fossil, have various pharmacological activities. Eighteen compounds were isolated from Ginkgo male flowers including a novel matsutake alcohol glycoside, Ginkgoside A ( 1 ), and 17 known compounds—calaliukiuenoside ( 2 ), benzylalcohol O‐α‐l ‐arabinopyranosyl‐(1 → 6)‐β‐d ‐glucopyranoside ( 3 ), amentoflavone ( 4 ), sciadopitysin ( 5 ), bilobetin ( 6 ), isoginkgetin ( 7 ), olivil 4‐O‐β‐d ‐glucopyranoside ( 8 ), dihydrodehydrodiconiferyl alcohol‐4‐O‐β‐d ‐glucoside ( 9 ), (+)‐cyclo‐olivil‐6‐O‐β‐d ‐glucopyranoside ( 10 ), (?)‐isolariciresinol 4‐O‐β‐d ‐glucopyranoside ( 11 ), coniferin ( 12 ), trans‐cinnamic acid‐4‐O‐β‐d ‐glucopyranoside ( 13 ), p‐coumaryl alchol glucoside ( 14 ), stroside B ( 15 ), methylconiferin ( 16 ), cis‐p‐coumaric acid 4‐O‐β‐d ‐glucopyranoside ( 17 ), and cis‐coniferin ( 18 ). Thirteen of these compounds had not previously found in Ginkgo. All extractive fractions and isolated compounds were evaluated for their anti‐inflammatory ability in the lipopolysaccharide‐induced RAW264.7 macrophages. The ethanol extract of Ginkgo flowers and the chloroform and ethyl acetate fractions can significantly decrease nitric oxide (NO), interleukin‐6 (IL‐6), and prostaglandin E₂ (PGE₂) production at 100 μg/ml. The most effective compounds, bilobetin ( 6 ) and isoginkgetin ( 7 ), elevated the NO inhibition ratios to 80.19% and 82.37% at 50 μM, respectively. They also exhibited significant dose‐dependent inhibitory effects on tumor necrosis factor‐α, IL‐6, PGE₂, inducible NO synthase mRNA, and cyclooxygenase‐2 mRNA levels. So they can be promising candidates for the development of new anti‐inflammatory agents.     

Antielastase and free radical scavenging activities of compounds from the stems of Cornus kousa

Bioassay‐guided investigation of the stems of Cornus kousa led to the isolation of 12 compounds such as four triterpenoids: betulinic acid (1), maslinic acid (2), arjunolic acid (3), 3‐isoarjunolic acid (4), four flavanoids; catechin (5), epi‐catechin (6), 2‐hydroxynaringenin (7), 2‐hydroxynaringenin‐7‐O‐β‐d ‐glucopyranoside (8), two ellagic acid derivatives; 3,4,3′‐tri‐O‐methylellagic acid (9), 3,4‐di‐O‐methylellagic acid (10), a daucosterol (11) and a sucrose derivative; (3′‐O‐p‐coumaroyl)‐β‐d ‐fructofuranosy‐(2?1)‐(6‐O‐p‐coumaroyl)‐α‐d ‐glucopyranoside (12). Their structures were elucidated on the basis of spectroscopic studies as well as by comparison with available data in the literature. The free radical scavenging activity and elastase inhibition activity were investigated for the development of antiaging ingredients as a raw material for use in cosmetics. Among these compounds, compounds 1, 2 and 8 showed significant elastase inhibition activity and IC₅₀ was 10.81 µg/mL, 21.21 µg/mL and 44.63 µg/mL, respectively, on porcine pancreatic elastase, whereas compounds 5, 6, 7 and 8 showed significant free radical scavenging activity and SC₅₀ was 8.37 µg/mL, 9.31 µg/mL, 9.23 µg/mL and 17.45 µg/mL, respectively. Copyright © 2007 John Wiley & Sons, Ltd.     

Antiinflammatory Constituents from Eclipta prostrata using RAW264.7 Macrophage Cells

The whole plant extract of Eclipta prostrata and its isolated compounds were tested for their antiinflammatory effects against lipopolysaccharide (LPS)‐induced nitric oxide (NO), prostaglandin E₂ (PGE₂) and tumor necrosis factor‐alpha (TNF‐α) release in RAW264.7 cells, as well as for the antiinflammatory mechanism of the active compound on mRNA expression. Among the isolated compounds, orobol (5) exhibited the highest activity against NO release with an IC₅₀ value of 4.6 μm , followed by compounds 1, 2 and 4 with IC₅₀ values of 12.7, 14.9 and 19.1 μm , respectively. The IC₅₀ value of compound 5 against PGE₂ release was found to be 49.6 μm , whereas it was inactive towards TNF‐α (IC₅₀ > 100 μm ). The mechanism of orobol (5) was found to down‐regulate iNOS and COX‐2 mRNA expression in a concentration‐dependent manner. The present study may support the traditional use of Eclipta prostrata for the treatment of inflammatory‐related diseases. Copyright © 2011 John Wiley & Sons, Ltd.     

Biological activities of xanthatin from Xanthium strumarium leaves

The objective of the present work was to evaluate the biological activities of the major bioactive compound, xanthatin, and other compounds from Xanthium strumarium (Asteraceae) leaves. Inhibition of bloodstream forms of Trypanosoma brucei brucei and leukaemia HL‐60 cell proliferation was assessed using resazurin as a vital stain. Xanthatin was found to be the major and most active compound against T. b. brucei with an IC₅₀ value of 2.63 µg/mL and a selectivity index of 20. The possible mode of action of xanthatin was further evaluated. Xanthatin showed antiinflammatory activity by inhibiting both PGE₂ synthesis (24% inhibition) and 5‐lipoxygenase activity (92% inhibition) at concentrations of 100 µg/mL and 97 µg/mL, respectively. Xanthatin exhibited weak irreversible inhibition of parasite specific trypanothione reductase. Unlike xanthatin, diminazene aceturate and ethidium bromide showed strong DNA intercalation with IC₅₀ values of 26.04 µg/mL and 44.70 µg/mL, respectively. Substantial induction of caspase 3/7 activity in MIA PaCa‐2 cells was observed after 6 h of treatment with 100 µg/mL of xanthatin. All these data taken together suggest that xanthatin exerts its biological activity by inducing apoptosis and inhibiting both PGE₂ synthesis and 5‐lipoxygenase activity thereby avoiding unwanted inflammation commonly observed in diseases such as trypanosomiasis. Copyright © 2011 John Wiley & Sons, Ltd.     

In vitro antimicrobial and antioxidant activities of anthrone and chromone from the latex of Aloe harlana Reynolds

In the search for new antimicrobial and antioxidant compounds from plants, the latex of the medicinal plant Aloe harlana Reynolds from Ethiopia was subjected to bioassay‐guided fractionation, which led to the isolation of two known compounds, anthrone (aloin) and chromone (7‐O‐methylaloeresin A). The latex and its two constituents were assessed for their possible antimicrobial activities against 23 bacterial and four fungal strains using the disc diffusion method and their antioxidant activity by two complementary test systems, namely 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) and 2‐deoxyribose degradation assay methods. The isolated compounds showed promising results against various pathogenic bacterial and fungal strains in comparison with standard drugs. Moreover, 7‐O‐methylaloeresin A exhibited good activity against multiple drug resistant Staphylococcus aureus (NCTC 11994) and Salmonella typhimurium (ATCC 1255) with MIC values of 0.72 and 0.18 mm , respectively. Among the fungal strains tested, Candida albicans (ATCC 10231) was the most susceptible organism to the latex and the two isolated compounds. The latex and isolated compounds also showed significant activities on both antioxidant assays with the highest activity being observed for 7‐O‐methylaloeresin A, which gave IC₅₀ values of 0.026 mm and 0.021 mm for DPPH and 2‐deoxyribose degradation assay, respectively. These findings support the traditional uses of the plant for the treatment of various infectious and inflammatory diseases. Copyright © 2011 John Wiley & Sons, Ltd.     

Antioxidant and antiinflammatory effect of Epilobium parviflorum Schreb.

Epilobium parviflorum Schreb. (Onagraceae) is used for the treatment of benign prostatic hyperplasia (BPH), but its biological action is not entirely identified. This paper aims to report data on E. parviflorum with respect to its antioxidant and antiinflammatory effects. The aqueous acetone extract of E. parviflorum showed higher antioxidant effect in the DPPH assay than well known antioxidants and inhibited the lipid peroxidation determined by the TBA assay (IC₅₀ = 2.37 ± 0.12 mg/mL). In concentrations of 0.2–15.0 µg/mL the extract possessed a protective effect, comparable to catalase (250 IU/mL), against oxidative damage, generated in fibroblast cells. In the COX inhibition assay E. parviflorum decreased the PGE₂ release, so showing inhibition of the COX‐enzyme (IC₅₀ = 1.4 ± 0.1 µg/mL). Copyright © 2008 John Wiley & Sons, Ltd.     

Effect of taxifolin glycoside on atopic dermatitis‐like skin lesions in NC/Nga mice

Increased levels of eosinphils, IgE, IL‐4, 5, and 13 and pro‐inflammatory factors (COX‐2, iNOS) are observed in patients with atopic dermatitis (AD). Taxifolin 3‐O‐β‐D‐glucopyranoside (TAX) from the roots of Rhododendron mucronulatum (RM) was examined to determine whether its immunomodulatory effect was applicable for treating atopic dermatitis. A total of 7 groups of NC/Nga mice with AD were treated by topical application or intraperitoneal injection of TAX for 4 weeks. Follow‐up evaluations were done to assess the changes in clinical observations, eosinophil counts, and levels of IgE, cytokines, COX‐2 and iNOS. In the clinical observation during the experimental period, TAX treatment significantly reduced the severity of AD‐like lesions induced in NC/Nga mice. Eosinophil and IgE levels decreased after treatment of the animals with TAX. TAX may thus be associated with improvement of eosinophil‐related allergic diseases. The expression of cytokines (IL‐4, 5 and 13) was significantly inhibited in the TAX‐treated group, suggesting that TAX might play an immunoregulatory role associated with AD. In RT‐PCR, iNOS and COX‐2 expression levels were reduced in the TAX‐treated group. In western blotting, the expression levels of iNOS and COX‐2 were also reduced in the TAX‐treated group. These findings suggest that TAX is effective for the treatment of AD by preventing the production of inflammatory cytokines and by reducing skin inflammation. Copyright © 2009 John Wiley & Sons, Ltd.     

Phenol Glycosides with In Vitro anti‐Helicobacter pylori Activity from Hypericum erectum Thunb

To evaluate the anti‐Helicobacter pylori activity of Hypericum erectum methanol extracts in order to provide the primary evidence for their use in clinical practice. An ethyl acetate fraction of H. erectum suspension‐cell cultures inhibited the growth of H. pylori in vitro, with a MIC₅₀ range of 38.7–63.2 μg/mL, comparable to metronidazole (MIC₅₀ = 43.2 μg/mL). To further investigate the involved active compounds of the H. erectum extracts, four phenol glycosides were isolated for the current study: quercetin‐3′‐O‐β‐d ‐galactopyranoside, quercetin‐3′‐O‐(2′′‐acetyl)‐β‐d ‐glucopyranoside, 4,6‐dihydroxy‐2‐methoxyphenyl‐1‐O‐β‐d ‐glucopyranoside and 4‐hydroxy‐2,6‐dimethoxyphenyl‐1‐O‐α‐l ‐rhamnopyranosyl(1–6)‐β‐d ‐glucopyranoside. The MIC₅₀ values of 4,6‐dihydroxy‐2‐methoxyphenyl‐1‐O‐β‐d ‐glucopyranoside and 4‐hydroxy‐2,6‐dimethoxyphenyl‐1‐O‐α‐l ‐rhamnopyranosyl(1–6)‐β‐d ‐glucopyranoside from ATCC43504 strains were 7.3 and 27.3 μg/mL, respectively. The other two phenol glycosides did not show anti‐H. pylori activity. The results of this work suggest that H. erectum has some therapeutic potential against H. pylori infection, which could be explored for patients with gastroduodenal disorders. Copyright © 2011 John Wiley & Sons, Ltd.     

Anti‐HIV‐1 Integrase Activity and Molecular Docking Study of Compounds from Caesalpinia sappan L.

Caesalpinia sappan L. (Caesalpiniaceae) has been traditionally used as blood tonic, expectorant, and astringent by boiling with water. Searching for HIV‐1 integrase (IN) inhibitors from this plant is a promising approach. The EtOH extract of C. sappan and its isolated compounds were tested for their anti‐HIV‐1 IN effect using the multiplate integration assay, and the active compounds were determined for their mechanisms by molecular docking technique. Extraction from the heartwoods and roots of C. sappan led to the isolation of nine compounds. Among the compounds tested, sappanchalcone (2) displayed the strongest effect against HIV‐1 IN with an IC₅₀ value of 2.3 μM followed by protosappanin A (9, IC₅₀ = 12.6 μM). Structure‐activity relationships of compounds from C. sappan were found, in which the vicinal hydroxyl moiety were essential for anti‐HIV‐1 IN effect of compounds 2 and 9 by binding with the amino acid residues Gln148 and Thr66 in the core domain of the HIV‐ 1 IN enzyme, respectively. Copyright © 2015 John Wiley & Sons, Ltd.     

Dolichandroside A,a new α‐glucosidase inhibitor and DPPH free‐radical Scavenger from Dolichandrone falcata seem

A new phenylpropanoid glycoside, dolichandroside‐A, together with seven known compounds α‐lapachone, lapachol, aloesaponarin II, 8‐hydroxydehydroiso‐α‐lapachone, β‐sitosterol, 3,8‐dihydroxydehydroiso‐α‐lapachone and verbascoside were isolated from the active ethyl acetate soluble extract of heartwood of Dolichandrone falcata. All except for dolichandroside‐A are known compounds, but have been isolated for the first time from this plant. The structure of all these compounds was determined on the basis of 1D‐ and 2D‐NMR spectral data. All the isolates were tested for α‐glucosidase inhibitory and DPPH radical scavenging activity. This is the first report identifying DPPH scavenging activity and α‐glucosidase inhibitory activity in D. falcata. Furthermore, along with a new compound, dolichandroside‐A, this study also assigns for the first time α‐glucosidase inhibitory activity to verbascoside and aloe saponarin‐II. Copyright © 2008 John Wiley & Sons, Ltd.     

Cycloartane triterpenoids from Cimicifuga yunnanensis induce apoptosis of breast cancer cells (MCF7) via p53‐dependent mitochondrial signaling pathway

The present study was carried out to investigate the antitumor activity of five cycloartane triterpenoids isolated from Cimicifuga yunnanensis on the breast cancer cell line MCF7 and its corresponding drug resistant subline R‐MCF7, including cimigenol‐3‐O‐β‐d ‐xylopyranoside (compound 1), 25‐O‐acetylcimigenol‐3‐O‐β‐d ‐xylopyranoside (compound 2), 25‐chlorodeoxycimigenol‐3‐O‐β‐d ‐xylopyranoside (compound 3), 25‐O‐acetylcimigenol‐3‐O‐α‐l ‐arabinopyranoside (compound 4) and 23‐O‐acetylcimigenol‐3‐O‐β‐d ‐xylopyranoside (compound 5). The results showed that compounds 2–5 have relatively high antitumor activity on both MCF7 and R‐MCF7 cells. The involvement of apoptosis as a major cause of cycloartane triterpenoids‐induced cell death was further confirmed. The results of RT‐PCR showed that compounds 2–5 increased the expression of p53 and bax, which led to the loss of mitochondrial potential and then resulted in the activation of caspase‐7. These findings collectively demonstrated that compounds 2–5 induced apoptosis of MCF7 via p53‐dependent mitochondrial pathway. Copyright © 2010 John Wiley & Sons, Ltd.     

Antiplasmodial activity of isolated compounds from Carpesium divaricatum

The whole plants of Carpesium divaricatum are used in traditional medicine as an antipyretic, analgesic and vermifugic, including a topical application for sores and inflammation. In a previous paper, the isolation and structural elucidation of isolated ineupatorolides A from methanol extracts of C. rosulatum (Compositae) were reported. The present paper deals with the isolation and identification of antiplasmodial compounds from C. divaricatum in Carpesium spp. Five compounds, 1β,6α‐dihydroxy‐4(15)‐eudesmene [1], β‐dictyopterol [2], 2‐isopropenyl‐6‐acetyl‐8‐methoxy‐1,3‐benzodioxin‐4‐one [3], (3E,6E,10E,14E,18E)‐2,6,10,15,19,23‐hexamethyl‐3,6,10,14,18,22‐tetracosahexaen‐2‐ol [4] and neophytadiene [5], were isolated from the whole plants of C. divaricatum. The in vitro activity against P. falciparum strain D10 was assessed using the parasite lactate dehydrogenase assay method. The main antiplasmodial principle, 2‐isopropenyl‐6‐acetyl‐8‐methoxy‐1,3‐benzodioxin‐4‐one [3], has been isolated from C. divaricatum for the first time. Compound 3 exhibited an antiplasmodial activity with IC₅₀ values of 2.3 ± 0.3 μm . This is the first report on the antiplasmodial activity of the compounds from C. divaricatum. Copyright © 2009 John Wiley & Sons, Ltd.     

灯盏细辛的抗氧化活性研究

目的:研究灯盏细辛6个化合物的抗氧化活性.方法:以灯盏细辛为原料,采用有机溶剂提取法和色谱柱法对灯盏细辛中化学成分进行提取与分离,利用核磁共振等波谱学方法进行结构鉴定,体外法检测6个化合物对1-二苯基-2-苦味酰肼自由基清除法( DPPH),2,2′-联氨-双-(3-乙基苯并噻唑啉-6-磺酸)自由基清除法(ABTS),O2·自由基和·OH自由基的清除能力,并以维生素C(Vc)为阳性对照,结果:6个化合物者对DPPH,ABTS,O-2·,·OH自由基均具有清除作用,且与浓度呈良好的量效关系,6个化合物清除自由基能力与Vc相似.结论:灯盏细辛中的6个化合物均具有较强的抗氧化活性.     

Modulatory Effect of an Urera Aurantiaca Extract on Immune and Tumoral Cells During Inflammation

There is a well known link between inflammation and cancer during initiation, propagation and metastasis. Urera aurantiaca (UA) Wedd. (Urticaceae) is a medicinal plant used in traditional medicine to treat inflammatory processes with proven in vivo antiinflammatory and antinociceptive effects. The effects of a methanolic extract (UA) and a purified fraction (PF) on the proliferation of normal and tumoral lymphocytes under the effect of prostaglandin E₂ (PGE₂) and on nitric oxide production by lipopolysaccharide‐stimulated macrophages was evaluated. Both UA and PF stimulated normal lymphocytes but, in presence of PGE_2, a modulatory effect was observed. The normal lymphocyte proliferation induced by PGE₂ was driven by pathways involving both PKC and H₂O₂. In macrophages, UA and PF did not modify cell viability and abrogated the synthesis of nitric oxide induced by lipopolysaccharide. In tumoral lymphocytes, the UA exerted a biphasic effect: at low concentrations it increased cell proliferation, while at high concentrations, it displayed an antiproliferative effect. UA and PF were capable of reverting the proliferative action of PGE₂. The tumoral cell proliferation induced by PGE₂ is related to PKC, ERK 1/2 and MAP Kinase P38 pathways. The observed effects could be attributed to polyphenols, flavonoids and tannins. This work demonstrates the modulatory effects of the UA on different cell types during inflammatory conditions, which reinforces its antiinflammatory action. Copyright © 2016 John Wiley & Sons, Ltd.     

Angiotensin‐Converting Enzyme Inhibitory Activity and Antioxidant Properties of Nepeta crassifolia Boiss & Buhse and Nepeta binaludensis Jamzad

This article reports phytochemical and biological studies on Nepeta binaludensis and Nepeta crassifolia. Both species were investigated for their angiotensin‐converting enzyme (ACE) inhibitory activity and antioxidant properties through three in vitro models [2,2‐diphenyl‐1‐picrylhydrazyl (DPPH), 2,2'‐azino‐bis(3‐ethylbenzothiazoline‐6‐sulphonic acid) (ABTS) and ferric reducing antioxidant power (FRAP) assay]. Aerial parts were extracted with methanol and partitioned between water and subsequently n‐hexane, ethyl acetate and n‐butanol. N. binaludensis methanol extract exerted significantly higher reducing power (1.9 μM Fe(II)/g) than did the positive control butylhydroxytoluene (63.2 μM Fe(II)/g) in FRAP assay. The highest DPPH radical scavenging activity was found for N. crassifolia, with IC₅₀ values of 9.6 and 12.1 µg/mL for ethyl acetate and n‐butanol fractions, respectively. n‐Butanol fraction of both species showed the highest ACE inhibitory activity, with IC₅₀ values of 59.3 and 81.7 µg/mL for N. binaludensis and N. crassifolia, respectively. Phytochemical investigations resulted in the isolation of ursolic acid, oleanolic acid, apigenin, luteolin and ixoroside. Apigenin‐7‐O‐glucoside, 8‐hydroxycirsimaritin and cirsimaritin were furthermore identified in N. crassifolia ethyl acetate‐soluble fraction. Nepetanudoside B was isolated from the n‐butanol fraction of N. binaludensis. Copyright © 2012 John Wiley & Sons, Ltd.