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Terminalia laxiflora and Terminalia brownii contain a broad spectrum of antimycobacterial compounds including ellagitannins, ellagic acid derivatives, triterpenes, fatty acids and fatty alcohols.
J Ethnopharmacol. 2018 Dec 05; 227:82-96.JE

Abstract

ETHNOPHARMACOLOGICAL RELEVANCE

Terminalia laxiflora Engl. & Diels, (Sudanese Arabic name: Darout الدروت) and Terminalia brownii Fresen (Sudanese Arabic name: Alshaf ألشاف) (Combretaceae) are used in Sudanese traditional folk medicine and in other African countries for treatment of infectious diseases, TB and its symptoms, such as cough, bronchitis and chest pain.

AIM OF STUDY

Because of the frequent use of T. laxiflora and T. brownii in African traditional medicine and due to the absence of studies regarding their antimycobacterial potential there was a need to screen extracts of T. laxiflora and T. brownii for their growth inhibitory potential and to study the chemical composition and compounds in growth inhibitory extracts.

MATERIALS AND METHODS

The plant species were collected in Sudan (Blue Nile Forest, Ed Damazin Forestry areas) and selected according to their uses in traditional medicine for the treatment of bacterial infections, including TB. Eighty extracts and fractions of the stem bark, stem wood, roots, leaves and fruits of T. laxiflora and T. brownii and nine pure compounds present in the active extracts were screened against Mycobacterium smegmatis ATCC 14468 using agar diffusion and microplate dilution methods. Inhibition zones and MIC values were estimated and compared to rifampicin. HPLC-UV/DAD, GC/MS and UHPLC/Q-TOF MS were employed to identify the compounds in the growth inhibitory extracts.

RESULTS

The roots of T. laxiflora and T. brownii gave the best antimycobacterial effects (IZ 22-27 mm) against Mycobacterium smegmatis. The lowest MIC of 625 µg/ml was observed for an acetone extract of the root of T. laxiflora followed by methanol and ethyl acetate extracts, both giving MIC values of 1250 µg/ml. Sephadex LH-20 column chromatography purification of T. brownii roots resulted in low MIC values of 62.5 µg/ml and 125 µg/ml for acetone and ethanol fractions, respectively, compared to 5000 µg/ml for the crude methanol extract. Methyl (S)-flavogallonate is suggested to be the main active compound in the Sephadex LH- 20 acetone fraction, while ellagic acid xyloside and methyl ellagic acid xyloside are suggested to give good antimycobacterial activity in the Sephadex LH-20 ethanol fraction. RP-18 TLC purifications of an ethyl acetate extract of T. laxiflora roots resulted in the enrichment of punicalagin in one of the fractions (Fr5). This fraction gave a five times smaller MIC (500 µg/ml) than the crude ethyl acetate extract (2500 µg/ml) and this improved activity is suggested to be mostly due to punicalagin. 1,18-octadec-9-ene-dioate, stigmast-4-en-3-one, 5α-stigmastan-3,6-dione, triacontanol, sitostenone and β-sitosterol were found in antimycobacterial hexane extracts of the stem bark of both studied species. Of these compounds, 1,18-octadec-9-ene-dioate, stigmast-4-en-3-one, 5α-stigmastan-3,6-dione, triacontanol, sitostenone have not been previously identified in T. brownii and T. laxiflora. Moreover, both plant species contained friedelin, betulinic acid, β-amyrine and two unknown oleanane-type triterpenoids. Of the listed compounds, friedelin, triacontanol and sitostenone gave a MIC of 250 µg/ml against M. smegmatis, whereas stigmasterol and β-sitosterol gave MIC values of 500 µg/ml.

CONCLUSIONS

Our results show that T. laxiflora and T. brownii contain antimycobacterial compounds of diverse polarities and support the traditional uses of various parts of T. laxiflora and T.brownii as decoctions for treatment of tuberculosis. Further investigations are warranted to explore additional (new) antimycobacterial compounds in the active extracts of T. laxiflora and T. brownii.

Authors+Show Affiliations

Faculty of Agriculture and Forestry, Department of Forest Sciences, Viikki Tropical Resources Institute, University of Helsinki, P.O. Box 27, FIN-00014, Finland; Faculty of Pharmacy, Division of Pharmaceutical Biosciences, Viikki Biocenter, University of Helsinki, P.O. Box 56, FIN-00014, Finland. Electronic address: enass.salih@helsinki.fi.Faculty of Science and Forestry, Department of Environmental and Biological Sciences, University of Eastern Finland, 80101 Joensuu, Finland.Faculty of Agriculture and Forestry, Department of Applied Chemistry and Microbiology, University of Helsinki, P.O. Box 27, Latokartanonkaari 11, FI-00014 Helsinki, Finland.Faculty of Agriculture and Forestry, Department of Forest Sciences, Viikki Tropical Resources Institute, University of Helsinki, P.O. Box 27, FIN-00014, Finland.Faculty of Agriculture and Forestry, Department of Forest Sciences, Viikki Tropical Resources Institute, University of Helsinki, P.O. Box 27, FIN-00014, Finland.Faculty of Agriculture and Forestry, Department of Forest Sciences, Viikki Tropical Resources Institute, University of Helsinki, P.O. Box 27, FIN-00014, Finland.Faculty of Agriculture and Forestry, Department of Applied Chemistry and Microbiology, University of Helsinki, P.O. Box 27, Latokartanonkaari 11, FI-00014 Helsinki, Finland.Faculty of Pharmacy, Division of Pharmaceutical Biosciences, Viikki Biocenter, University of Helsinki, P.O. Box 56, FIN-00014, Finland.Faculty of Pharmacy, Division of Pharmaceutical Biosciences, Viikki Biocenter, University of Helsinki, P.O. Box 56, FIN-00014, Finland. Electronic address: pia.fyhrquist@helsinki.fi.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29733942

Citation

Salih, Enass Y A., et al. "Terminalia Laxiflora and Terminalia Brownii Contain a Broad Spectrum of Antimycobacterial Compounds Including Ellagitannins, Ellagic Acid Derivatives, Triterpenes, Fatty Acids and Fatty Alcohols." Journal of Ethnopharmacology, vol. 227, 2018, pp. 82-96.
Salih EYA, Julkunen-Tiitto R, Lampi AM, et al. Terminalia laxiflora and Terminalia brownii contain a broad spectrum of antimycobacterial compounds including ellagitannins, ellagic acid derivatives, triterpenes, fatty acids and fatty alcohols. J Ethnopharmacol. 2018;227:82-96.
Salih, E. Y. A., Julkunen-Tiitto, R., Lampi, A. M., Kanninen, M., Luukkanen, O., Sipi, M., Lehtonen, M., Vuorela, H., & Fyhrquist, P. (2018). Terminalia laxiflora and Terminalia brownii contain a broad spectrum of antimycobacterial compounds including ellagitannins, ellagic acid derivatives, triterpenes, fatty acids and fatty alcohols. Journal of Ethnopharmacology, 227, 82-96. https://doi.org/10.1016/j.jep.2018.04.030
Salih EYA, et al. Terminalia Laxiflora and Terminalia Brownii Contain a Broad Spectrum of Antimycobacterial Compounds Including Ellagitannins, Ellagic Acid Derivatives, Triterpenes, Fatty Acids and Fatty Alcohols. J Ethnopharmacol. 2018 Dec 5;227:82-96. PubMed PMID: 29733942.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Terminalia laxiflora and Terminalia brownii contain a broad spectrum of antimycobacterial compounds including ellagitannins, ellagic acid derivatives, triterpenes, fatty acids and fatty alcohols. AU - Salih,Enass Y A, AU - Julkunen-Tiitto,Riitta, AU - Lampi,Anna-Maija, AU - Kanninen,Markku, AU - Luukkanen,Olavi, AU - Sipi,Marketta, AU - Lehtonen,Mari, AU - Vuorela,Heikki, AU - Fyhrquist,Pia, Y1 - 2018/05/04/ PY - 2017/06/12/received PY - 2017/12/07/revised PY - 2018/04/21/accepted PY - 2018/5/8/pubmed PY - 2018/12/12/medline PY - 2018/5/8/entrez KW - Corilagin (PubChem CID: 73568) KW - Ellagic acid (PubChem CID: 5281855) KW - Ellagitannins KW - Fatty compounds KW - Friedelin (PubChem CID: 91472) KW - Mycobacterium smegmatis KW - Punicalagin (PubChem CID: 16148440) KW - Sitostenone (PubChem CID: 241573) KW - Terminalia brownii KW - Terminalia laxiflora KW - Triacontanol (PubChem CID: 68972) KW - Triterpenoids KW - β-Sitosterol (PubChem CID: 222284) SP - 82 EP - 96 JF - Journal of ethnopharmacology JO - J Ethnopharmacol VL - 227 N2 - ETHNOPHARMACOLOGICAL RELEVANCE: Terminalia laxiflora Engl. & Diels, (Sudanese Arabic name: Darout الدروت) and Terminalia brownii Fresen (Sudanese Arabic name: Alshaf ألشاف) (Combretaceae) are used in Sudanese traditional folk medicine and in other African countries for treatment of infectious diseases, TB and its symptoms, such as cough, bronchitis and chest pain. AIM OF STUDY: Because of the frequent use of T. laxiflora and T. brownii in African traditional medicine and due to the absence of studies regarding their antimycobacterial potential there was a need to screen extracts of T. laxiflora and T. brownii for their growth inhibitory potential and to study the chemical composition and compounds in growth inhibitory extracts. MATERIALS AND METHODS: The plant species were collected in Sudan (Blue Nile Forest, Ed Damazin Forestry areas) and selected according to their uses in traditional medicine for the treatment of bacterial infections, including TB. Eighty extracts and fractions of the stem bark, stem wood, roots, leaves and fruits of T. laxiflora and T. brownii and nine pure compounds present in the active extracts were screened against Mycobacterium smegmatis ATCC 14468 using agar diffusion and microplate dilution methods. Inhibition zones and MIC values were estimated and compared to rifampicin. HPLC-UV/DAD, GC/MS and UHPLC/Q-TOF MS were employed to identify the compounds in the growth inhibitory extracts. RESULTS: The roots of T. laxiflora and T. brownii gave the best antimycobacterial effects (IZ 22-27 mm) against Mycobacterium smegmatis. The lowest MIC of 625 µg/ml was observed for an acetone extract of the root of T. laxiflora followed by methanol and ethyl acetate extracts, both giving MIC values of 1250 µg/ml. Sephadex LH-20 column chromatography purification of T. brownii roots resulted in low MIC values of 62.5 µg/ml and 125 µg/ml for acetone and ethanol fractions, respectively, compared to 5000 µg/ml for the crude methanol extract. Methyl (S)-flavogallonate is suggested to be the main active compound in the Sephadex LH- 20 acetone fraction, while ellagic acid xyloside and methyl ellagic acid xyloside are suggested to give good antimycobacterial activity in the Sephadex LH-20 ethanol fraction. RP-18 TLC purifications of an ethyl acetate extract of T. laxiflora roots resulted in the enrichment of punicalagin in one of the fractions (Fr5). This fraction gave a five times smaller MIC (500 µg/ml) than the crude ethyl acetate extract (2500 µg/ml) and this improved activity is suggested to be mostly due to punicalagin. 1,18-octadec-9-ene-dioate, stigmast-4-en-3-one, 5α-stigmastan-3,6-dione, triacontanol, sitostenone and β-sitosterol were found in antimycobacterial hexane extracts of the stem bark of both studied species. Of these compounds, 1,18-octadec-9-ene-dioate, stigmast-4-en-3-one, 5α-stigmastan-3,6-dione, triacontanol, sitostenone have not been previously identified in T. brownii and T. laxiflora. Moreover, both plant species contained friedelin, betulinic acid, β-amyrine and two unknown oleanane-type triterpenoids. Of the listed compounds, friedelin, triacontanol and sitostenone gave a MIC of 250 µg/ml against M. smegmatis, whereas stigmasterol and β-sitosterol gave MIC values of 500 µg/ml. CONCLUSIONS: Our results show that T. laxiflora and T. brownii contain antimycobacterial compounds of diverse polarities and support the traditional uses of various parts of T. laxiflora and T.brownii as decoctions for treatment of tuberculosis. Further investigations are warranted to explore additional (new) antimycobacterial compounds in the active extracts of T. laxiflora and T. brownii. SN - 1872-7573 UR - https://www.unboundmedicine.com/medline/citation/29733942/Terminalia_laxiflora_and_Terminalia_brownii_contain_a_broad_spectrum_of_antimycobacterial_compounds_including_ellagitannins_ellagic_acid_derivatives_triterpenes_fatty_acids_and_fatty_alcohols_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0378-8741(17)32243-2 DB - PRIME DP - Unbound Medicine ER -