Bioactive compounds from marigold processing waste: Extraction, isolation, and antidiabetic activity

Nellippatta Deepika; Basavan Duraiswamy; Salma Khanam; Divanji Maohar; Hebbani Nagarajappa Shivaprasad; Tripathy Amrutanand

doi:10.7324/JAPS.2023.126892

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Abstract

Diabetes is a chronic metabolic disorder characterized by excessive blood sugar levels. According to the International Diabetes Federation, 537 million adults are living with diabetes today and is projected to rise to 643 million by 2030 and 783 million by 2045. Marigold or Tagetes erecta Linn. is a common plant used in diverse cultures in India. Different parts of this plant are used in folk medicine to treat colic, diarrhea, vomiting, fever, skin diseases, and hepatic disorders. During marigold cultivation, the leaves are the most common agricultural waste. In the present study, we aim to evaluate the in-vitro antidiabetic activity of hydroalcoholic extract of leaves of marigold and the isolation and characterization of active constituents. The hydroalcoholic extract was fractionated by column chromatography using different stationary phases and solvents ranging from highly non-polar to polar as mobile phase by gradient elution method. In-vitro alpha-glucosidase inhibition of the hydroalcoholic extract and isolated compounds was performed and compared with the standard drug acarbose. The isolated compounds were tentatively characterized as kaempferol di-O-rhamnoside (compound 1), kaempferol O-rhamnoside-O-pentoside (compound 2), and kaempferol O-rhamnoside (compound 3). The isolated compounds were more active than the hydroalcoholic extract. Kaempferol O-rhamnoside was found to possess the highest antidiabetic activity with an IC₅₀value of 61 μg/ml.

Citation:

Deepika NP, Duraiswamy B, Khanam S, Maohar D, Shivaprasad HN, Amrutanand T. Bioactive compounds from marigold processing waste: Extraction, isolation, and antidiabetic activity. J Appl Pharm Sci, 2023; 13(Suppl 1):021–027. https://doi.org/10.7324/JAPS.2023.126892

Copyright: © The Author(s). This is an open-access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Adhikari-Devkota A, Dirar AI, Kurizaki A, Tsushiro K, Devkota HP. Extraction and isolation of kaempferol glycosides from the leaves and twigs of Lindera neesiana. Separations, 2019; 6:10. https://doi.org/10.3390/separations6010010
Akmal M, Wadhwa R. Alpha glucosidase inhibitors. NCBI Bookshelf, 2022.
Barros L, Dueñas M, Ferreira IC, Carvalho AM, Santos-Buelga C. Use of HPLC-DAD-ESI/MS to profile phenolic compounds in edible wild greens from Portugal. Food Chem, 2011; 127:169-73. https://doi.org/10.1016/j.foodchem.2011.01.009
Bu T, Liu M, Zheng L, Guo Y, Lin X. α-glucosidase inhibition and the in vivo hypoglycemic effect of butyl-isobutyl-phthalate derived from the Laminaria japonica rhizoid. Phytother Res, 2010; 24:1588-91. https://doi.org/10.1002/ptr.3139
Calderon-Montano JM, Burgos-Morón E, Pérez-Guerrero C, López-Lázaro M. A review on the dietary flavonoid kaempferol. Mini Rev Med Chem, 2011; 11:298-344. https://doi.org/10.2174/138955711795305335
Caesar LK, Cech NB. Synergy and antagonism in natural product extracts: when 1+ 1 does not equal 2. Nat Prod Rep, 2019; 36(6):869-88. https://doi.org/10.1039/C9NP00011A
De Melo GO, do Malvar DC, Vanderlinde FA, Rocha FF, Pires PA, Costa EA, de Matos LG, Kaiser CR, Costa SS. Antinociceptive and anti-inflammatory kaempferol glycosides from Sedum dendroideum. J Ethnopharmacol, 2009; 124:228-32. https://doi.org/10.1016/j.jep.2009.04.024
de Sousa E, Zanatta L, Seifriz I, Creczynski-Pasa TB, Pizzolatti MG, Szpoganicz B, Silva FRMB. Hypoglycemic effect and antioxidant potential of kaempferol-3, 7-O-(α)-dirhamnoside from Bauhinia forficata leaves. J Nat Prod, 2004; 67:829-32. https://doi.org/10.1021/np030513u
Dimas K, Demetzos C, Mitaku S, Marselos M, Tzavaras T, Kokkinopoulos D. Cytotoxic activity of kaempferol glycosides against human leukaemic cell lines in vitro. Pharmacol Res, 2000; 41:83-6. https://doi.org/10.1006/phrs.1999.0562
Elyamani R, Soulaymani A, Hami H. Epidemiology of cardiovascular diseases in Morocco: a systematic review. Rev Diabetes Stud, 2021; 17(2):57-67. https://doi.org/10.1900/RDS.2021.17.57
Forsyth WGC. Cacao polyphenolic substances. 3. Separation and estimation on paper chromatograms. Biochem J, 1955; 60:108. https://doi.org/10.1042/bj0600108
Gopi G, Elumalai A, Jayasri P. A concise review on Tagetes erecta. Int J Phytopharm Res, 2012; 3:16-9.
Kashyap PK, Singh S, Singh MK, Gupta A, Tandon S, Shanker K, Verma RK, Verma RS. An efficient process for the extraction of lutein and chemical characterization of other organic volatiles from marigold (Tagetes erecta L.) flower. Food Chem, 2022; 396:133647. https://doi.org/10.1016/j.foodchem.2022.133647
Karwani G, Sisodia SS. Tagetes erecta plant: review with significant pharmacological activities. World J Pharm Sci, 2015; 2:1180-3.
Kiranmai M, Kazim SM, Ibrahim M. Combined wound healing activity of Gymnema sylvestre and Tagetes erecta Linn. Int J Pharm Appl, 2011; 2:135-40.
Kurian JC, Mutatkar RK, Samraj E. Plants that heal. PH Lall, Oriental Watchman Publishing House, 1995.
Lebovitz HE. Alpha-glucosidase inhibitors. Endocrinol Metab Clin N Am, 1997; 26:539-51. https://doi.org/10.1016/S0889-8529(05)70266-8
Kusmiati K, Caesarianto W, Afiati F, Hutabarat R. Effect lutein of marigold flower (Tagetes erecta L.) on decreasing glucose and malondialdehyde levels in Alloxan-induced blood mice. In AIP Conference Proceedings. AIP Publishing LLC, vol. 2120, no. 1, p. 070009, 2019. https://doi.org/10.1063/1.5115726
Liu Y, Cao Y, Fang S, Wang T, Yin Z, Shang X, Yang W, Fu X. Antidiabetic effect of Cyclocarya paliurus leaves depends on the contents of antihyperglycemic flavonoids and antihyperlipidemic triterpenoids. Molecules, 2018; 23:1042. https://doi.org/10.3390/molecules23051042
Madanan MT, Shah IK, Varghese GK, Kaushal RK. Application of Aztec marigold (Tagetes erecta L.) for phytoremediation of heavy metal polluted lateritic soil. Environ Chem Ecotoxicol, 2021; 3:17-22. https://doi.org/10.1016/j.enceco.2020.10.007
Mitrocotsa D, Mitaku S, Axarlis S, Harvala C, Malamas M. Evaluation of the antiviral activity of kaempferol and its glycosides against human cytomegalovirus. Planta Med, 2000; 66:377-9. https://doi.org/10.1055/s-2000-8550
Negri G, Santi D de, Tabach R. Flavonol glycosides found in hydroethanolic extracts from Tilia cordata, a species utilized as anxiolytics. Rev Brasil Plantas Med, 2013; 15:217-24. https://doi.org/10.1590/S1516-05722013000200008
Nikkon F, Habib MR, Saud ZA, Karim MR, Roy AK, Zaman S. Toxicological evaluation of chloroform fraction of flower of Tagetes erecta L. on rats. Int J Drug Dev Res, 2009; 1:161-5.
Priyanka D, Shalini T, Navneet VK. A brief study on marigold (Tagetes species): a review. Int Res J Pharm, 2013; 4:43-8.
Phrutivorapongkul A, Kiattisin K, Jantrawut P, Chansakaow S, Vejabhikul S, Leelapornpisid P. Appraisal of biological activities and identification of phenolic compound of African marigold (Tagetes erecta) flower extract. Pak J Pharm Sci, 2013; 26(6):1071-6.
Rhama S, Madhavan S. Antibacterial activity of the flavonoid, patulitrin isolated from the flowers of Tagetes erecta L. Int J Pharm Tech Res, 2011; 3:1407-9.
Pratheesh VB, Benny N, Sujatha CH. Isolation, stabilization and characterization of xanthophyll from marigold flower-Tagetes erecta-L. Modern Appl Sci, 2009; 3:19-28. https://doi.org/10.5539/mas.v3n2p19
Saisugun J, Sasidhar RLC. Extraction and biological evaluation of esterified lutein from marigold flower petals. J Pharmacogn Phytochem, 2019; 8(4):3403-10.
Sing Y, Gupta A, Kannojia P. Tagetes erecta (Marigold)-a review on its phytochemical and medicinal properties. Curr Med Drugs Res, 2020; 4(1):1-6. https://doi.org/10.53517/CMDR.2581-5008.412020201
Sun H, Saeedi P, Karuranga S, Pinkepank M, Ogurtsova K, Duncan BB, Stein C, Basit A, Chan JC, Mbanya JC, Pavkov ME. IDF diabetes atlas: global, regional and country-level diabetes prevalence estimates for 2021 and projections for 2045. Diabetes Res Clin Pract, 2022; 183:109119. https://doi.org/10.1016/j.diabres.2021.109119
Telagari M, Hullatti K. In-vitro α-amylase and α-glucosidase inhibitory activity of Adiantum caudatum Linn. and Celosia argentea Linn. extracts and fractions. Indian J Pharmacol, 2015; 47:425-9. https://doi.org/10.4103/0253-7613.161270
Tripathi B, Bhatia R, Walia S, Kumar B. Chemical composition and evaluation of Tagetes erecta (var. Pusa narangi genda) essential oil for its antioxidant and antimicrobial activity. Biopesticides Int, 2012; 8:138-46.
Wang W, Xu H, Chen H, Tai K, Liu F, Gao Y. In vitro antioxidant, anti-diabetic and antilipemic potentials of quercetagetin extracted from marigold (Tagetes erecta L.) inflorescence residues. J Food Sci Technol, 2016; 53:2614-24. https://doi.org/10.1007/s13197-016-2228-6
Xu L-W, Wang G-Y, Shi Y-P. Chemical constituents from Tagetes erecta flowers. Chem Nat Compounds, 2011; 47:281-3. https://doi.org/10.1007/s10600-011-9905-5

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Adhikari-Devkota A, Dirar AI, Kurizaki A, Tsushiro K, Devkota HP. Extraction and isolation of kaempferol glycosides from the leaves and twigs of Lindera neesiana. Separations, 2019; 6:10. https://doi.org/10.3390/separations6010010

Akmal M, Wadhwa R. Alpha glucosidase inhibitors. NCBI Bookshelf, 2022.

Barros L, Dueñas M, Ferreira IC, Carvalho AM, Santos-Buelga C. Use of HPLC-DAD-ESI/MS to profile phenolic compounds in edible wild greens from Portugal. Food Chem, 2011; 127:169-73. https://doi.org/10.1016/j.foodchem.2011.01.009

Bu T, Liu M, Zheng L, Guo Y, Lin X. α-glucosidase inhibition and the in vivo hypoglycemic effect of butyl-isobutyl-phthalate derived from the Laminaria japonica rhizoid. Phytother Res, 2010; 24:1588-91. https://doi.org/10.1002/ptr.3139

Calderon-Montano JM, Burgos-Morón E, Pérez-Guerrero C, López-Lázaro M. A review on the dietary flavonoid kaempferol. Mini Rev Med Chem, 2011; 11:298-344. https://doi.org/10.2174/138955711795305335

Caesar LK, Cech NB. Synergy and antagonism in natural product extracts: when 1+ 1 does not equal 2. Nat Prod Rep, 2019; 36(6):869-88. https://doi.org/10.1039/C9NP00011A

De Melo GO, do Malvar DC, Vanderlinde FA, Rocha FF, Pires PA, Costa EA, de Matos LG, Kaiser CR, Costa SS. Antinociceptive and anti-inflammatory kaempferol glycosides from Sedum dendroideum. J Ethnopharmacol, 2009; 124:228-32. https://doi.org/10.1016/j.jep.2009.04.024

de Sousa E, Zanatta L, Seifriz I, Creczynski-Pasa TB, Pizzolatti MG, Szpoganicz B, Silva FRMB. Hypoglycemic effect and antioxidant potential of kaempferol-3, 7-O-(α)-dirhamnoside from Bauhinia forficata leaves. J Nat Prod, 2004; 67:829-32. https://doi.org/10.1021/np030513u

Dimas K, Demetzos C, Mitaku S, Marselos M, Tzavaras T, Kokkinopoulos D. Cytotoxic activity of kaempferol glycosides against human leukaemic cell lines in vitro. Pharmacol Res, 2000; 41:83-6. https://doi.org/10.1006/phrs.1999.0562

Elyamani R, Soulaymani A, Hami H. Epidemiology of cardiovascular diseases in Morocco: a systematic review. Rev Diabetes Stud, 2021; 17(2):57-67. https://doi.org/10.1900/RDS.2021.17.57

Forsyth WGC. Cacao polyphenolic substances. 3. Separation and estimation on paper chromatograms. Biochem J, 1955; 60:108. https://doi.org/10.1042/bj0600108

Gopi G, Elumalai A, Jayasri P. A concise review on Tagetes erecta. Int J Phytopharm Res, 2012; 3:16-9.

Kashyap PK, Singh S, Singh MK, Gupta A, Tandon S, Shanker K, Verma RK, Verma RS. An efficient process for the extraction of lutein and chemical characterization of other organic volatiles from marigold (Tagetes erecta L.) flower. Food Chem, 2022; 396:133647. https://doi.org/10.1016/j.foodchem.2022.133647

Karwani G, Sisodia SS. Tagetes erecta plant: review with significant pharmacological activities. World J Pharm Sci, 2015; 2:1180-3.

Kiranmai M, Kazim SM, Ibrahim M. Combined wound healing activity of Gymnema sylvestre and Tagetes erecta Linn. Int J Pharm Appl, 2011; 2:135-40.

Kurian JC, Mutatkar RK, Samraj E. Plants that heal. PH Lall, Oriental Watchman Publishing House, 1995.

Lebovitz HE. Alpha-glucosidase inhibitors. Endocrinol Metab Clin N Am, 1997; 26:539-51. https://doi.org/10.1016/S0889-8529(05)70266-8

Kusmiati K, Caesarianto W, Afiati F, Hutabarat R. Effect lutein of marigold flower (Tagetes erecta L.) on decreasing glucose and malondialdehyde levels in Alloxan-induced blood mice. In AIP Conference Proceedings. AIP Publishing LLC, vol. 2120, no. 1, p. 070009, 2019. https://doi.org/10.1063/1.5115726

Liu Y, Cao Y, Fang S, Wang T, Yin Z, Shang X, Yang W, Fu X. Antidiabetic effect of Cyclocarya paliurus leaves depends on the contents of antihyperglycemic flavonoids and antihyperlipidemic triterpenoids. Molecules, 2018; 23:1042. https://doi.org/10.3390/molecules23051042

Madanan MT, Shah IK, Varghese GK, Kaushal RK. Application of Aztec marigold (Tagetes erecta L.) for phytoremediation of heavy metal polluted lateritic soil. Environ Chem Ecotoxicol, 2021; 3:17-22. https://doi.org/10.1016/j.enceco.2020.10.007

Mitrocotsa D, Mitaku S, Axarlis S, Harvala C, Malamas M. Evaluation of the antiviral activity of kaempferol and its glycosides against human cytomegalovirus. Planta Med, 2000; 66:377-9. https://doi.org/10.1055/s-2000-8550

Negri G, Santi D de, Tabach R. Flavonol glycosides found in hydroethanolic extracts from Tilia cordata, a species utilized as anxiolytics. Rev Brasil Plantas Med, 2013; 15:217-24. https://doi.org/10.1590/S1516-05722013000200008

Nikkon F, Habib MR, Saud ZA, Karim MR, Roy AK, Zaman S. Toxicological evaluation of chloroform fraction of flower of Tagetes erecta L. on rats. Int J Drug Dev Res, 2009; 1:161-5.

Priyanka D, Shalini T, Navneet VK. A brief study on marigold (Tagetes species): a review. Int Res J Pharm, 2013; 4:43-8.

Phrutivorapongkul A, Kiattisin K, Jantrawut P, Chansakaow S, Vejabhikul S, Leelapornpisid P. Appraisal of biological activities and identification of phenolic compound of African marigold (Tagetes erecta) flower extract. Pak J Pharm Sci, 2013; 26(6):1071-6.

Rhama S, Madhavan S. Antibacterial activity of the flavonoid, patulitrin isolated from the flowers of Tagetes erecta L. Int J Pharm Tech Res, 2011; 3:1407-9.

Pratheesh VB, Benny N, Sujatha CH. Isolation, stabilization and characterization of xanthophyll from marigold flower-Tagetes erecta-L. Modern Appl Sci, 2009; 3:19-28. https://doi.org/10.5539/mas.v3n2p19

Saisugun J, Sasidhar RLC. Extraction and biological evaluation of esterified lutein from marigold flower petals. J Pharmacogn Phytochem, 2019; 8(4):3403-10.

Sing Y, Gupta A, Kannojia P. Tagetes erecta (Marigold)-a review on its phytochemical and medicinal properties. Curr Med Drugs Res, 2020; 4(1):1-6. https://doi.org/10.53517/CMDR.2581-5008.412020201

Sun H, Saeedi P, Karuranga S, Pinkepank M, Ogurtsova K, Duncan BB, Stein C, Basit A, Chan JC, Mbanya JC, Pavkov ME. IDF diabetes atlas: global, regional and country-level diabetes prevalence estimates for 2021 and projections for 2045. Diabetes Res Clin Pract, 2022; 183:109119. https://doi.org/10.1016/j.diabres.2021.109119

Telagari M, Hullatti K. In-vitro α-amylase and α-glucosidase inhibitory activity of Adiantum caudatum Linn. and Celosia argentea Linn. extracts and fractions. Indian J Pharmacol, 2015; 47:425-9. https://doi.org/10.4103/0253-7613.161270

Tripathi B, Bhatia R, Walia S, Kumar B. Chemical composition and evaluation of Tagetes erecta (var. Pusa narangi genda) essential oil for its antioxidant and antimicrobial activity. Biopesticides Int, 2012; 8:138-46.

Wang W, Xu H, Chen H, Tai K, Liu F, Gao Y. In vitro antioxidant, anti-diabetic and antilipemic potentials of quercetagetin extracted from marigold (Tagetes erecta L.) inflorescence residues. J Food Sci Technol, 2016; 53:2614-24. https://doi.org/10.1007/s13197-016-2228-6

Xu L-W, Wang G-Y, Shi Y-P. Chemical constituents from Tagetes erecta flowers. Chem Nat Compounds, 2011; 47:281-3. https://doi.org/10.1007/s10600-011-9905-5