New Iridoids from the Medicinal Plant Barleria prionitis with Potent Activity against Respiratory Syncytial Virus

Chen, Jian Lu; Blanc, Phillipe; Stoddart, Cheryl A.; Bogan, Mark; Rozhon, Edward J.; Parkinson, Nigel; Ye, Zhijun; Cooper, Raymond; Balick, Michael J.; Nanakorn, Weerachai; Kernan, Michael R.

doi:10.1021/np980086y

Cited by 91 publications

(61 citation statements)

References 8 publications

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“…14) 16. 106.0 (C-4), 28.4 (C-5), 25.9 (C-6), 69.7 (C-7), 133.2 (C-8), 43.8 (C-9), 121.0 (C-10), 99.7 (C-1Ј), 74.6 (C-2Ј), 77.7 (C-3Ј), 71.4 (C-4Ј), 77.0 (C-5Ј), 68.5 (C-6Ј), 110.9 (C-1Љ), 79.2 (C-2Љ), 80.4 (C-3Љ), 74.9 (C-4Љ), 65.5 (C-5Љ). Lonicera quinquelocularis (Caprifoliaceae).…”

Section: Biological and Pharmacological Activity Of Naturally Occurrimentioning

confidence: 99%

Naturally Occurring Secoiridoids and Bioactivity of Naturally Occurring Iridoids and Secoiridoids. A Review, Part 2

Debnath²,

2007

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This is a second part of a review 1) and is mainly a compilation of new secoiridoids reported in the literature during 1994-2005 as well as a high-light of biological and pharmacological activity of iridoids and secoiridoids published during 1998--2005. The earlier first part of review 1) included new naturally occurring iridoids (glycosides, aglycones, derivatives and dimers) reported during 1994-2005. Secoiridoids are monoterpenoids based on the 7,8-secocyclopenta[c]-pyranoid skeleton and represented by 1a. They are possibly derived in plants from iridoid, loganin 1b by oxidative cleavage with redox enzyme to 1c and then undergo various secondary modifications of the basic skeleton namely, epoxidation, oxidation, hydroxylation and esterification of the generated hydroxyl groups leading a group of compounds which constitute the class. The main aim of this review is for rapid identification of isolated secoiridoids by comparison of spectral data as well as to draw attention of the natural product chemists for evaluation of biological and pharmacological activity of the isolated iridoids and secoiridoids in order to justify the use of medicinal plants containing these metabolites in folk medicines. In certain plants, the isolated metabolites showed biological activities other than the use of the concerned plants in traditional system of medicine. The high-light of pharmacological activity may possibly draw the attention of the synthetic chemists for design of new drugs using known iridoids as raw materials.A number of review articles on plant secoiridoids are available. Listings of naturally occurring secoiridoids together with spectroscopic data and plant source (review of El-Naggar and Beal covering the literature through January, 1980 2) and of Boros and Stermitz covering the literature through December, 1989 3) ), and without spectroscopic data (review of Hazimi and Alkhathlan covering through December, 1993 4) ) are available. The reviews on biological activity of plant iridoids, namely of Sticher, covering the works reported up to 1976, 5) of Ghisalberti and of Mandal et al. covering the literature up to a part of 1997 6,7) are also available. Secoiridoids are listed in Table 1 in a fashion similar to that of the Boros and Stermitz review.3) All the new secoiridoids are arranged in four groups. Group 1 contains simple secoiridoids; whereas group 2 contains terpene-conjugated secoiridoids; group 3 contains aromatic conjugated secoiridoids and group 4 contains bis-, tris-and tetrakis-secoiridoids. The oxidation state of C-10 and C-11 guides the arrangement of compounds in each group except group 4. The available data for each compound were listed in the following order: name; structure; molecular formula; calculated molecular weight as per atomic weight of most abundant isotopic atoms of C, H, O, etc.; melting point (°C); optical rotation, [a] D (with concentration and solvent); UV (solvent, l max in nm, log e); IR (medium, n max in cm C-NMR data to the first decimal point. Assignments with the s...

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Section: Biological and Pharmacological Activity Of Naturally Occurrimentioning

confidence: 99%

Naturally Occurring Secoiridoids and Bioactivity of Naturally Occurring Iridoids and Secoiridoids. A Review, Part 2

Debnath²,

2007

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“…In India and Thailand, the decoction of leaves and flowers of B. prionitis is used in the treatment of viral fever [4]. The plant shows biological activity against respiratory syncytial virus [5] and also has been reported as anti-arthritic, anti-inflammatory [4] and anti-fertility [6] agent. The aqueous bioactive fractions are reported to possess hepatoprotective, anti-stress and immunorestorative properties [7].…”

Section: Introductionmentioning

confidence: 99%

Glutathione S-Transferase, Acetylcholinesterase Inhibitory and Antibacterial Activities of Chemical Constituents of Barleria prionitis

Kosmulalage

Zahid

Udenigwe

et al. 2007

Zeitschrift Für Naturforschung B

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Phytochemical studies on the ethanolic extract of Barleria prionitis of Sri Lankan origin have resulted in the isolation of a new compound, balarenone (1), along with three known compounds, pipataline (2), lupeol (3) and 13,14-seco-stigmasta-5,14-diene-3-α-ol (4). The structures of 1 -4 were elucidated with the aid of extensive NMR spectroscopic studies. Compounds 1 -4 showed moderate inhibitory activity against glutathione S-transferase (GST) and acetylcholinesterase (AChE). Compounds 1, 2 and 4 also exhibited antibacterial activity against Bacillus cereus and Pseudomonas aeruginosa (25 µg/disk). Three different derivatives of compound (2), 7,8-epoxypipataline (5), 8-amino-7-hydroxypipataline (6) and 7,8-dibromopipataline (7) were synthesized to evaluate them for GST and AChE inhibitory activities. Household microwave radiations were used to synthesize compound (6). Among all tested compounds, 8-amino-7-hydroxypipataline (6) exhibited a significant AChE inhibitory activity with an IC 50 value of 36.8 µ M.

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“…Kumar et al (2013) (Sawarkar et al, 2009;Nishant et al, 2014). Kumari et al, (2015) Some of the isolated compound from the herbs to name few are, 6-hydroxyflavones, scutellarein-7-rhamnosyl glucoside, barlerin, acetyl barlerin, luteolin-7-O-β-Dglucoside, shanziside methyl ester, 6-O-trans-p-coumaroyl-8-O-acetyl shanziside methyl ester, lupilinoside7-methoxydiderroside, 1,8 dihydroxy-2,7-dimethyl-3,6-dimethoxy anthraquinone,1,3,6,8-tetramethoxy-2,7-dimethyl anthraquinone, prioniside A, prioniside B, prioniside C, balarenone, pipataline (Taneja and Tiwari, 1975;Soren et al, 1982;Gupta and Saxena;1984;Chen et al, 1998;Singh et al, 2005;Ata et al, 2009;Ganga Raju et al, 2002;Ata et al, 2007;Kosmulalage et al, 2007).…”

Section: Discussionmentioning

confidence: 99%

Antimicrobial and cytotoxic activities of Barleria prionitis and Barleria grandiflora: A comparative study

Sawarkar¹,

Kashyap²,

Pandey³

et al. 2016

Bangladesh J Pharmacol

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Leaf juices as well as leaves of Barleria prionitis and Barleria grandiflora are being used by rural people across various regions of India in the treatment of oral ailments such as dental troubles, gum ailments, pyorrhoea, dental carries and mouth ulcers. Zone of inhibition and MIC values obtained for all the extracts suggest ethanolic extract of the herbs were more antimicrobial when compared to the aqueous extract. Results of biofilm suppression were found statistically significant (p<0.05) when compared to control. Cytotoxicity was evaluated by MTT assay on human gingival fibroblast and human dermal fibroblast cell lines for ethanolic extract of the herbs. CTC50 value was found to be more than 1,000 µg/mL for ethanolic extracts of both herbs. Chlorhexidine was found to be more cytotoxic with CTC50 value of 12.5–25 µg/mL. Ethanolic extract of B. prionitis and B. grandiflora found significantly cytotoxic (p<0.05) in comparison with control.Video Clip:<a href="https://youtube.com/v/DNByJJQT3RY">Cytotoxicity assay:</a> 18 min 45 sec

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New Iridoids from the Medicinal Plant Barleria prionitis with Potent Activity against Respiratory Syncytial Virus

Cited by 91 publications

References 8 publications

Naturally Occurring Secoiridoids and Bioactivity of Naturally Occurring Iridoids and Secoiridoids. A Review, Part 2

Naturally Occurring Secoiridoids and Bioactivity of Naturally Occurring Iridoids and Secoiridoids. A Review, Part 2

Glutathione S-Transferase, Acetylcholinesterase Inhibitory and Antibacterial Activities of Chemical Constituents of Barleria prionitis

Antimicrobial and cytotoxic activities of <i>Barleria prionitis</i> and <i>Barleria grandiflora</i>: A comparative study

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