Skip to main content
Top
Published in: Journal of Natural Medicines 2/2018

01-03-2018 | Original Paper

Anti-oral common pathogenic bacterial active acetylenic acids from Thesium chinense Turcz

Authors: Chang Liu, Xiao-Tian Li, Rong-Rong Cheng, Zhu-Zhen Han, Li Yang, Zhong-Chen Song, Zheng-Tao Wang

Published in: Journal of Natural Medicines | Issue 2/2018

Login to get access

Abstract

Discovery of agents for oral infectious diseases is always encouraged in natural products chemistry. A bioassay-guided isolation led to the isolation of two new acetylenic acids (1, 2) along with seven known ones (39) from the ethanol extract of Thesium chinense Turcz, a commonly used oral anti-bacterial and anti-inflammatory herb. Their structures were elucidated on the basis of spectroscopic and chemical evidence. Exocarpic acid (3) demonstrated the most promising activity against three tested oral pathogenic bacterial strains, Porphyromonas gingivalis, Fusobacterium nucleatum, and Streptococcus mutans, with minimum inhibitory concentration values of 0.86, 3.43, and 13.70 μg/mL, respectively. Compounds 1, 2, 4, 5 and 7 also showed potential activities against periodontal bacteria (P. gingivalis, F. nucleatum).
Literature
1.
go back to reference Chen X, Wu G, Feng Z (2016) Advanced biomaterials and their potentialial applications in the treatment of periodontal disease. Crit Rev Biotechnol 36:760–775PubMed Chen X, Wu G, Feng Z (2016) Advanced biomaterials and their potentialial applications in the treatment of periodontal disease. Crit Rev Biotechnol 36:760–775PubMed
2.
go back to reference Goyal G, Garg T, Rath G (2014) Current nanotechnological strategies for an effective delivery of drugs in treatment of periodontal disease. Crit Rev Ther Drug 31:89–119CrossRef Goyal G, Garg T, Rath G (2014) Current nanotechnological strategies for an effective delivery of drugs in treatment of periodontal disease. Crit Rev Ther Drug 31:89–119CrossRef
3.
go back to reference Michalowicz BS, Hodges JS, DiAngelis AJ (2006) Treatment of periodontal disease and the risk of preterm birth. New Engl J Med 355:1885–1894CrossRefPubMed Michalowicz BS, Hodges JS, DiAngelis AJ (2006) Treatment of periodontal disease and the risk of preterm birth. New Engl J Med 355:1885–1894CrossRefPubMed
6.
go back to reference Haffajee AD, Socransky SS (1994) Microbial etiological agents of destructive periodontal diseases. Periodontol 2000 5:78–111CrossRefPubMed Haffajee AD, Socransky SS (1994) Microbial etiological agents of destructive periodontal diseases. Periodontol 2000 5:78–111CrossRefPubMed
7.
go back to reference Cao CF, Sun XP (1998) Herbal medicine for periodontal diseases. Int Dent J 48:16–321CrossRef Cao CF, Sun XP (1998) Herbal medicine for periodontal diseases. Int Dent J 48:16–321CrossRef
8.
go back to reference Xiong J, Li S, Wang W (2013) Screening and identification of the antibacterial bioactive compounds from Lonicera japonica Thunb. leaves. Food Chem 138:327–333CrossRefPubMed Xiong J, Li S, Wang W (2013) Screening and identification of the antibacterial bioactive compounds from Lonicera japonica Thunb. leaves. Food Chem 138:327–333CrossRefPubMed
9.
go back to reference Jang YJ, Kim ME, Ko SY (2011) n-Butanol extracts of Panax notoginseng suppress LPS-induced MMP-2 expression in periodontal ligament fibroblasts and inhibit osteoclastogenesis by suppressing MAPK in LPS-activated RAW264. 7 cells. Arch Oral Biol 56:1319–1327CrossRefPubMed Jang YJ, Kim ME, Ko SY (2011) n-Butanol extracts of Panax notoginseng suppress LPS-induced MMP-2 expression in periodontal ligament fibroblasts and inhibit osteoclastogenesis by suppressing MAPK in LPS-activated RAW264. 7 cells. Arch Oral Biol 56:1319–1327CrossRefPubMed
10.
go back to reference Tsao TF, Newman MG, Kwok YY (1982) Effect of Chinese and western antimicrobial agents on selected oral bacteria. J Dent Res 61:1103–1106CrossRefPubMed Tsao TF, Newman MG, Kwok YY (1982) Effect of Chinese and western antimicrobial agents on selected oral bacteria. J Dent Res 61:1103–1106CrossRefPubMed
11.
go back to reference Li M, Xu Z (2007) The inhibition of dentifrice containing the lotus leaf-derived inhibitor on periodontitis related bacteria in vitro. Int Dent J 57:303–306CrossRefPubMed Li M, Xu Z (2007) The inhibition of dentifrice containing the lotus leaf-derived inhibitor on periodontitis related bacteria in vitro. Int Dent J 57:303–306CrossRefPubMed
12.
go back to reference Li M, Xu Z (2008) Quercetin in a lotus leaves extract may be responsible for antibacterial activity. Arch Pharm Res 31:640–644CrossRefPubMed Li M, Xu Z (2008) Quercetin in a lotus leaves extract may be responsible for antibacterial activity. Arch Pharm Res 31:640–644CrossRefPubMed
13.
go back to reference Shu Y, Liu Y, Li L (2011) Antibacterial activity of quercetin on oral infectious pathogens. Afr J Microbiol Res 5:5358–5361 Shu Y, Liu Y, Li L (2011) Antibacterial activity of quercetin on oral infectious pathogens. Afr J Microbiol Res 5:5358–5361
14.
go back to reference Rezende K, Lucarini R, Símaro GV (2016) Antibacterial activity of (-)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections. Rev Bras Farmacogn 26:296–303CrossRef Rezende K, Lucarini R, Símaro GV (2016) Antibacterial activity of (-)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections. Rev Bras Farmacogn 26:296–303CrossRef
16.
go back to reference Shin SY, Bajpai VK, Kim HR (2007) Antibacterial activity of bioconverted eicosapentaenoic (EPA) and docosahexaenoic acid (DHA) against foodborne pathogenic bacteria. Int J Food Microbiol 113:233–236CrossRefPubMed Shin SY, Bajpai VK, Kim HR (2007) Antibacterial activity of bioconverted eicosapentaenoic (EPA) and docosahexaenoic acid (DHA) against foodborne pathogenic bacteria. Int J Food Microbiol 113:233–236CrossRefPubMed
17.
go back to reference Cha JD, Jeong MR, Jeong SI (2014) Antibacterial activity of sophoraflavanone G isolated from the roots of Sophora flavescens and Red Ginseng Extract. Int J Med Plants 106:418–429 Cha JD, Jeong MR, Jeong SI (2014) Antibacterial activity of sophoraflavanone G isolated from the roots of Sophora flavescens and Red Ginseng Extract. Int J Med Plants 106:418–429
18.
go back to reference Parveen Z, Deng Y, Mk Dai R (2007) Antiinflammatory and analgesic activities of Thesium chinense Turcz extracts and its major flavonoids, kaempferol and kaempferol-3-O-glucoside. Yakugaku Zasshi 127:1275–1279CrossRefPubMed Parveen Z, Deng Y, Mk Dai R (2007) Antiinflammatory and analgesic activities of Thesium chinense Turcz extracts and its major flavonoids, kaempferol and kaempferol-3-O-glucoside. Yakugaku Zasshi 127:1275–1279CrossRefPubMed
19.
go back to reference Bourjot M, Leyssen P, Eydoux C (2012) Chemical constituents of Anacolosa pervilleana and their antiviral activities. Fitoterapia 83:1076–1080CrossRefPubMed Bourjot M, Leyssen P, Eydoux C (2012) Chemical constituents of Anacolosa pervilleana and their antiviral activities. Fitoterapia 83:1076–1080CrossRefPubMed
20.
go back to reference El-Jaber N, Estevez-Braun A, Ravelo AG (2003) Acetylenic acids from the aerial parts of Nanodea muscosa. J Nat Prod 66:722–724CrossRefPubMed El-Jaber N, Estevez-Braun A, Ravelo AG (2003) Acetylenic acids from the aerial parts of Nanodea muscosa. J Nat Prod 66:722–724CrossRefPubMed
21.
go back to reference Van Staden J, Hutchings A (1992) Exocarpic acid and other compounds from tubers and inflorescences of Sarcophyte sanguinea. Phytochemistry 31:3929–3931CrossRef Van Staden J, Hutchings A (1992) Exocarpic acid and other compounds from tubers and inflorescences of Sarcophyte sanguinea. Phytochemistry 31:3929–3931CrossRef
22.
go back to reference Nikolaeva IG, Dymsheeva LD, Nikolaev SM (2007) Antioxidant activity and flavonoid composition of the new nootropic preparation polynoophyt. Pharm Chem J 41:532–535CrossRef Nikolaeva IG, Dymsheeva LD, Nikolaev SM (2007) Antioxidant activity and flavonoid composition of the new nootropic preparation polynoophyt. Pharm Chem J 41:532–535CrossRef
23.
go back to reference Bylka W, Matlawska I (2001) Flavonoids and free phenolic acids from Phytolacca americana L. leaves. Acta Polo Pharm 58:69–72 Bylka W, Matlawska I (2001) Flavonoids and free phenolic acids from Phytolacca americana L. leaves. Acta Polo Pharm 58:69–72
24.
go back to reference Ahmed SA, Kamel EM (2013) Chemical constituents, cytotoxic and antibacterial activities of the aerial parts of Brassica nigra. Int J Bioassays 2:1134–1138 Ahmed SA, Kamel EM (2013) Chemical constituents, cytotoxic and antibacterial activities of the aerial parts of Brassica nigra. Int J Bioassays 2:1134–1138
25.
go back to reference Kazuma K, Noda N, Suzuki M (2003) Malonylated flavonol glycosides from the petals of Clitoria ternatea. Phytochemistry 62:229–237CrossRefPubMed Kazuma K, Noda N, Suzuki M (2003) Malonylated flavonol glycosides from the petals of Clitoria ternatea. Phytochemistry 62:229–237CrossRefPubMed
26.
go back to reference Wu H, Dushenkov S, Ho CT (2009) Novel acetylated flavonoid glycosides from the leaves of Allium ursinum. Food Chem 115:592–595CrossRef Wu H, Dushenkov S, Ho CT (2009) Novel acetylated flavonoid glycosides from the leaves of Allium ursinum. Food Chem 115:592–595CrossRef
27.
go back to reference Sabitha G, Reddy CS, Yadav JS (2006) Total syntheses of the highly potential anti-cancer polyacetylenes, (S)-18-hydroxyminquartynoic acid, (S)-minquartynoic acid and (E)-15, 16-dihydrominquartynoic acid. Tetrahedron Lett 47:4513–4516CrossRef Sabitha G, Reddy CS, Yadav JS (2006) Total syntheses of the highly potential anti-cancer polyacetylenes, (S)-18-hydroxyminquartynoic acid, (S)-minquartynoic acid and (E)-15, 16-dihydrominquartynoic acid. Tetrahedron Lett 47:4513–4516CrossRef
28.
go back to reference Zhou W, Zhang X, Zhu CL (2016) Melatonin receptor agonists as the ‘perioceutics’ agents for periodontal disease through modulation of Porphyromonas gingivalis virulence and inflammatory response. PLoS One 11:e0166442CrossRefPubMedPubMedCentral Zhou W, Zhang X, Zhu CL (2016) Melatonin receptor agonists as the ‘perioceutics’ agents for periodontal disease through modulation of Porphyromonas gingivalis virulence and inflammatory response. PLoS One 11:e0166442CrossRefPubMedPubMedCentral
Metadata
Title
Anti-oral common pathogenic bacterial active acetylenic acids from Thesium chinense Turcz
Authors
Chang Liu
Xiao-Tian Li
Rong-Rong Cheng
Zhu-Zhen Han
Li Yang
Zhong-Chen Song
Zheng-Tao Wang
Publication date
01-03-2018
Publisher
Springer Singapore
Published in
Journal of Natural Medicines / Issue 2/2018
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-018-1180-3

Other articles of this Issue 2/2018

Journal of Natural Medicines 2/2018 Go to the issue