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Anthelmintic activity of trans-cinnamaldehyde and A- and B-type proanthocyanidins derived from cinnamon (Cinnamomum verum).

Williams AR, Ramsay A, Hansen TV, Ropiak HM, Mejer H, Nejsum P, Mueller-Harvey I, Thamsborg SM - Sci Rep (2015)

Bottom Line: Cinnamon (Cinnamomum verum) has been shown to have anti-inflammatory and antimicrobial properties, but effects on parasitic worms of the intestine have not been investigated.It is proposed that the rapid absorption or metabolism of CA in vivo may prevent it from being present in sufficient concentrations in situ to exert efficacy.Therefore, further work should focus on whether formulation of CA can enhance its activity against internal parasites.

View Article: PubMed Central - PubMed

Affiliation: Department of Veterinary Disease Biology, Faculty of Health and Medical Sciences, University of Copenhagen, Frederiksberg, Denmark.

ABSTRACT
Cinnamon (Cinnamomum verum) has been shown to have anti-inflammatory and antimicrobial properties, but effects on parasitic worms of the intestine have not been investigated. Here, extracts of cinnamon bark were shown to have potent in vitro anthelmintic properties against the swine nematode Ascaris suum. Analysis of the extract revealed high concentrations of proanthocyanidins (PAC) and trans-cinnamaldehyde (CA). The PAC were subjected to thiolysis and HPLC-MS analysis which demonstrated that they were exclusively procyanidins, had a mean degree of polymerization of 5.2 and 21% of their inter-flavan-3-ol links were A-type linkages. Purification of the PAC revealed that whilst they had activity against A. suum, most of the potency of the extract derived from CA. Trichuris suis and Oesophagostomum dentatum larvae were similarly susceptible to CA. To test whether CA could reduce A. suum infection in pigs in vivo, CA was administered daily in the diet or as a targeted, encapsulated dose. However, infection was not significantly reduced. It is proposed that the rapid absorption or metabolism of CA in vivo may prevent it from being present in sufficient concentrations in situ to exert efficacy. Therefore, further work should focus on whether formulation of CA can enhance its activity against internal parasites.

No MeSH data available.


Related in: MedlinePlus

HPLC chromatograms of cinnamon bark extract.(a) HPLC chromatogram of cinnamon bark extract: Top panel shows detection of trans-cinnamaldehyde. Bottom panel shows larger version of the area indicated by the red arrow in top panel, showing 2, A-type procyanidin (PC) dimer; 3, A-type PC trimer; 5, A-type PC trimer; 6, internal standard; 7, cis—Cinnamic acid; 9, trans—Cinnamic acid. (b) HPLC chromatogram of thiolysed cinnamon bark extract (BM = benzylmercaptan adduct): 1, Catechin; 2, A-type PC dimer; 3, A-type PC trimer; 4, Epicatechin; 5, A-type PC trimer; 6, Internal standard; 7, cis—Cinnamic acid; 8, A-type PC—BM trimer; 9, trans—Cinnamic acid; 10, cis Catechin—BM; 11, Epicatechin—BM; 12, A-type PC—BM dimer.
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f3: HPLC chromatograms of cinnamon bark extract.(a) HPLC chromatogram of cinnamon bark extract: Top panel shows detection of trans-cinnamaldehyde. Bottom panel shows larger version of the area indicated by the red arrow in top panel, showing 2, A-type procyanidin (PC) dimer; 3, A-type PC trimer; 5, A-type PC trimer; 6, internal standard; 7, cis—Cinnamic acid; 9, trans—Cinnamic acid. (b) HPLC chromatogram of thiolysed cinnamon bark extract (BM = benzylmercaptan adduct): 1, Catechin; 2, A-type PC dimer; 3, A-type PC trimer; 4, Epicatechin; 5, A-type PC trimer; 6, Internal standard; 7, cis—Cinnamic acid; 8, A-type PC—BM trimer; 9, trans—Cinnamic acid; 10, cis Catechin—BM; 11, Epicatechin—BM; 12, A-type PC—BM dimer.

Mentions: To identify the putative anthelmintic compounds, we analysed the extract by LC-MS. The major compound was CA, which accounted for 7.8 g/100 g of the extract (Fig. 3A). In addition, cinnamic acid and several PAC dimers and trimers with A-type linkages were detected by LC-MS (Fig. 3A). To gain further insight into the PAC composition, the extract was subjected to thiolysis with benzyl mercaptan, which breaks PAC polymers with B-type bonds and allows quantification of their constituent flavan-3-ol units2425. This revealed that these cinnamon PAC were procyanidins that consisted of catechin and epicatechin as terminal and extension units (Fig. 3B; Table 1). The calculated proportions of flavan-3-ol sub-units are shown in Tables S1-2. From this information, both the total amount of PAC and the mean degree of polymerization (mDP - i.e. the average length of the polymers) can be calculated. This revealed that the extract contained 24.2 g PAC/100 g extract, and the mDP was 5.2. Furthermore, analysis of the inter-flavanol links demonstrated that 21% were A-type and 79% were B-type linkages (Table 1).


Anthelmintic activity of trans-cinnamaldehyde and A- and B-type proanthocyanidins derived from cinnamon (Cinnamomum verum).

Williams AR, Ramsay A, Hansen TV, Ropiak HM, Mejer H, Nejsum P, Mueller-Harvey I, Thamsborg SM - Sci Rep (2015)

HPLC chromatograms of cinnamon bark extract.(a) HPLC chromatogram of cinnamon bark extract: Top panel shows detection of trans-cinnamaldehyde. Bottom panel shows larger version of the area indicated by the red arrow in top panel, showing 2, A-type procyanidin (PC) dimer; 3, A-type PC trimer; 5, A-type PC trimer; 6, internal standard; 7, cis—Cinnamic acid; 9, trans—Cinnamic acid. (b) HPLC chromatogram of thiolysed cinnamon bark extract (BM = benzylmercaptan adduct): 1, Catechin; 2, A-type PC dimer; 3, A-type PC trimer; 4, Epicatechin; 5, A-type PC trimer; 6, Internal standard; 7, cis—Cinnamic acid; 8, A-type PC—BM trimer; 9, trans—Cinnamic acid; 10, cis Catechin—BM; 11, Epicatechin—BM; 12, A-type PC—BM dimer.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4588565&req=5

f3: HPLC chromatograms of cinnamon bark extract.(a) HPLC chromatogram of cinnamon bark extract: Top panel shows detection of trans-cinnamaldehyde. Bottom panel shows larger version of the area indicated by the red arrow in top panel, showing 2, A-type procyanidin (PC) dimer; 3, A-type PC trimer; 5, A-type PC trimer; 6, internal standard; 7, cis—Cinnamic acid; 9, trans—Cinnamic acid. (b) HPLC chromatogram of thiolysed cinnamon bark extract (BM = benzylmercaptan adduct): 1, Catechin; 2, A-type PC dimer; 3, A-type PC trimer; 4, Epicatechin; 5, A-type PC trimer; 6, Internal standard; 7, cis—Cinnamic acid; 8, A-type PC—BM trimer; 9, trans—Cinnamic acid; 10, cis Catechin—BM; 11, Epicatechin—BM; 12, A-type PC—BM dimer.
Mentions: To identify the putative anthelmintic compounds, we analysed the extract by LC-MS. The major compound was CA, which accounted for 7.8 g/100 g of the extract (Fig. 3A). In addition, cinnamic acid and several PAC dimers and trimers with A-type linkages were detected by LC-MS (Fig. 3A). To gain further insight into the PAC composition, the extract was subjected to thiolysis with benzyl mercaptan, which breaks PAC polymers with B-type bonds and allows quantification of their constituent flavan-3-ol units2425. This revealed that these cinnamon PAC were procyanidins that consisted of catechin and epicatechin as terminal and extension units (Fig. 3B; Table 1). The calculated proportions of flavan-3-ol sub-units are shown in Tables S1-2. From this information, both the total amount of PAC and the mean degree of polymerization (mDP - i.e. the average length of the polymers) can be calculated. This revealed that the extract contained 24.2 g PAC/100 g extract, and the mDP was 5.2. Furthermore, analysis of the inter-flavanol links demonstrated that 21% were A-type and 79% were B-type linkages (Table 1).

Bottom Line: Cinnamon (Cinnamomum verum) has been shown to have anti-inflammatory and antimicrobial properties, but effects on parasitic worms of the intestine have not been investigated.It is proposed that the rapid absorption or metabolism of CA in vivo may prevent it from being present in sufficient concentrations in situ to exert efficacy.Therefore, further work should focus on whether formulation of CA can enhance its activity against internal parasites.

View Article: PubMed Central - PubMed

Affiliation: Department of Veterinary Disease Biology, Faculty of Health and Medical Sciences, University of Copenhagen, Frederiksberg, Denmark.

ABSTRACT
Cinnamon (Cinnamomum verum) has been shown to have anti-inflammatory and antimicrobial properties, but effects on parasitic worms of the intestine have not been investigated. Here, extracts of cinnamon bark were shown to have potent in vitro anthelmintic properties against the swine nematode Ascaris suum. Analysis of the extract revealed high concentrations of proanthocyanidins (PAC) and trans-cinnamaldehyde (CA). The PAC were subjected to thiolysis and HPLC-MS analysis which demonstrated that they were exclusively procyanidins, had a mean degree of polymerization of 5.2 and 21% of their inter-flavan-3-ol links were A-type linkages. Purification of the PAC revealed that whilst they had activity against A. suum, most of the potency of the extract derived from CA. Trichuris suis and Oesophagostomum dentatum larvae were similarly susceptible to CA. To test whether CA could reduce A. suum infection in pigs in vivo, CA was administered daily in the diet or as a targeted, encapsulated dose. However, infection was not significantly reduced. It is proposed that the rapid absorption or metabolism of CA in vivo may prevent it from being present in sufficient concentrations in situ to exert efficacy. Therefore, further work should focus on whether formulation of CA can enhance its activity against internal parasites.

No MeSH data available.


Related in: MedlinePlus