Naturally derived anti‐HIV agents

Asres, Kaleab; Seyoum, Ameha; Veeresham, Ciddi; Bučar, Franz; Gibbons, Simon

doi:10.1002/ptr.1629

Cited by 148 publications

(77 citation statements)

References 209 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…; afterwards, this EEE isomer was isolated successively from Rosaceae, 14) Quercus dentata pollen, 15) anthers of Aphelandra tetraffona and A. chamissoniana (a ZZZ isomer also was isolated concomitantly), 12) sunflower (Helianthus annuus L.) pollen, 16) and Brazilian bee pollen. 17) Pharmacologically, this principal compound has been reported to have anti-human immunodeficiency virus (HIV) infection, 11,18) anti-Helicobacter pylori, 19) anti-tumor, 20,21) anti-fungal, 22) and antioxidant activities. 17) More recently (by the year of 2008), several tri-pcoumaroylspermidines with property of cis-trans conformation such as the ZZZ, EEE, EZE, and EZZ isomer have also been found in safflower [the florets of Carthamus tinctorius (Compositae)].…”

Section: Resultsmentioning

confidence: 99%

Structural Identification of a New Tri-p-coumaroylspermidine with Serotonin Transporter Inhibition from Safflower

Zhao

Qin

Gai

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Safflower (Carthamus tinctorius L.), a member of the family Compositae, geologically distributes in all regions in China, and is utilized for producing herbal medicines for the treatment of inflammatory diseases, hyperlipemia, arteriosclerosis, gynecological disorders, and osteoporosis. 1) To date, it has been known to contain flavonoids, 2) cartharmin, safflower yellow A, quinochalone, safflomin, cartorimine, alkaloids, 3) lignans, fatty acids, 4) triterpene alcohols, 5) and serotonin derivatives.6-8) Additionally, several coumaroylspermidine analogs also were found in safflower, i.e., a principal analog N 1 ,N 5 ,N 10 -(E)-tri-p-coumaroylspermidine (EEE) and its three cis-trans isomers [N 1 ,N 5 9) indicating that that some other geometric isomers of tri-p-coumaroylspermidine could exist in the natural plant. In our previous preliminary screening, we discovered that safflower extracts (especially ethyl acetate extract (HE) and n-butyl alcohol fraction) had regulatory actions on the monoamine transports in transporter-transgenic Chinese hamster ovary (CHO) cells, that is, activations of dopamine (DA)/norepinephrine (NE) uptake and an inhibition of serotonin (5HT) uptake, 10) implying that there may be some constituent(s) acting as serotonin transporter (SERT) blocker(s). In this study, we thereby chose to isolate and characterize the structurally unknown, SERT-targeting compound(s) from the HE fraction by using an activity-directed extraction method and a series of NMR techniques. Finally, one of the active isolates was identified and elucidated as N 1 ,N 5 -(Z)-N 10 -(E)-tri-p-coumaroylspermidine (CX), a new tri-p-coumaroylspermidine as postulated previously by us. Results and DiscussionThe ethyl acetate extract of safflower (Carthamus tinctorius L.) was separated by column chromatography on silica gel and Sephadex LH-20 in combination with a concomitant bioactivity-tracing technique (detailed paradigm described in Supplemental) to afford a bioactive compound CX (designated as carthamide X by us) (Fig. 1). HPLC showed that the purity of CX sample was 95.6% (while the content of CX in HE was only 0.028%). Due to the sensitivity, validity, and feasibility, 10) our screening platform previously established by using isotope-ligand-detection methods is suggested suitable for tracing some structurally unknown/unstable compounds with a sparse content in natural plants when combined with phytochemical techniques, which could, however, be hard to be isolated by traditional phytochemical method alone.The We previously reported that safflower (Carthamus tinctorius L.) ethyl acetate extract (HE) possessed an inhibitory action on serotonin (5HT) uptake in Chinese hamster ovary (CHO) cells expressing 5HT transporter (SERT) (S6 cells). Here, HE was adopted to go through an activity-guided isolation, and then an ingredient with potent SERT inhibitory action was obtained, which was elucidated as N

show abstract

Section: Resultsmentioning

confidence: 99%

Structural Identification of a New Tri-p-coumaroylspermidine with Serotonin Transporter Inhibition from Safflower

Zhao

Qin

Gai

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…Most of the antiviral agents that are currently being used are limited in therapeutic potencies and may possess several other problems in the clinical practices such as tolerability, contraindications, toxicity amongst others not to mention the availability and cost of the drugs, hence the need for an alternative approach or therapeutic measures (Asres et al, 2005;Verma et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

In-ovo biological activities of Phyllanthus amarus leaf extracts against Newcastle disease virus

Faeji¹,

Oladunmoye²,

Adebayo³

et al. 2017

J. Med. Plants Res.

View full text Add to dashboard Cite

Newcastle disease virus is a paramyxovirus which causes Newcastle disease in birds. Investigation was done on the effect of leaf extract of Phyllanthus amarus against Newcastle disease virus (NDV) using an in-ovo assay. Nine to eleven day-old viable embryonated chicken eggs (ECE) were used for the assay, these were divided into six groups of six eggs each. Methanol, aqueous and n-hexane extracts of the plant leaves were administered to the various groups at concentrations varying from 50 to 5 mg/ml. Embryonated eggs were incubated and embryo survival was monitored daily. Negative control and diluents control groups received phosphate buffer saline (PBS) and dimethly suphoxide (DMSO), respectively. The other group was uninoculated while a virus control group received 100 EID 50 /0.1 ml NDV alone. Bacteria free allantoic fluid from the embryonated eggs in different treatment groups were harvested and collected for spot hemagglutination (HA) test and HA assay to detect the presence of NDV viral particles and the viral titre, respectively. Leaf extracts were assayed for presence of phytochemicals and antioxidant potentials. It was observed from the results that the extract was toxic to the embryo at a concentration above 50 mg/ml and further results showed that the HA viral titre reduction was directly proportional to increasing extract concentration. The phytochemical assays of leaf extract revealed the presence of phytochemicals including alkaloids, tannins, saponins, flavonoids, phenols, steroids, glycosides. The current findings have demonstrated that leaf extract from P. amarus has potentials of medicinal value as well as antiviral activity against NDV in-ovo. Further experimental assays using live animal models are recommended to validate the use of P. amarus plant extract in therapeutic measure in chickens.

show abstract

“…The long-term toxicity, adverse effects, and rapid emergence of drug resistance have become serious problems in treating HIV-1 infections (Asres et al 2005). In recent years, the HIV-1 integrase (IN) has been a very attractive target for developing novel anti-HIV drugs because it is one of the essential enzymes used for replication of HIV and it has no known counterpart in humans.…”

Section: Introductionmentioning

confidence: 99%

Anti-HIV-1 integrase compounds from Dioscorea bulbifera and molecular docking study

Chaniad

Wattanapiromsakul

Pianwanit

et al. 2016

Pharmaceutical Biology

View full text Add to dashboard Cite

Context Dioscorea bulbifera L. (Dioscoreaceae) has been used in a traditional Thai longevity medicine preparation. Isolation of inhibitors from natural products is a potential source for continuous development of new HIV-1 integrase (IN) inhibitors. Objective The objective of this study is to isolate the compounds and evaluate their anti-HIV-1 IN activity, as well as to predict the potential interactions of the compounds with an IN. Materials and methods The ethyl acetate and water fractions (1-100 mg/mL) of Dioscorea bulbifera bulbils were isolated and tested for their anti-HIV-1 IN activity using the multiplate integration assay (MIA). The interactions of the active compounds with IN were investigated using a molecular docking method. Results and discussions The ethyl acetate and water fractions of Dioscorea bulbifera bulbils afforded seven compounds. Among these, allantoin (1), 2,4,3 0 ,5 0 -tetrahydroxybibenzyl (2), and 5,7,4 0 -trihydroxy-2-styrylchromone (5) were isolated for the first time from this plant. Myricetin (4) exhibited the most potent activity with an IC 50 value of 3.15 mM, followed by 2,4,6,7-tetrahydroxy-9,10-dihydrophenanthrene (3, IC 50 value¼ 14.20 mM), quercetin-3-O-b-D-glucopyranoside (6, IC 50 value ¼ 19.39 mM) and quercetin-3-O-b-D-galactopyranoside (7, IC 50 value ¼ 21.80 mM). Potential interactions of the active compounds (3, 4, 6, and 7) with the IN active site were additionally investigated. Compound 4 showed the best binding affinity to IN and formed strong interactions with various amino acid residues. These compounds interacted with Asp64, Thr66, His67, Glu92, Asp116, Gln148, Glu152, Asn155, and Lys159, which are involved in both the 3 0 -processing and strand transfer reactions of IN. In particular, galloyl, catechol, and sugar moieties were successful inhibitors for HIV-1 IN.ARTICLE HISTORY

show abstract

Naturally derived anti‐HIV agents

Cited by 148 publications

References 209 publications

Structural Identification of a New Tri-p-coumaroylspermidine with Serotonin Transporter Inhibition from Safflower

Structural Identification of a New Tri-p-coumaroylspermidine with Serotonin Transporter Inhibition from Safflower

In-ovo biological activities of Phyllanthus amarus leaf extracts against Newcastle disease virus

Anti-HIV-1 integrase compounds from Dioscorea bulbifera and molecular docking study

Contact Info

Product

Resources

About