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Stillingia lineata subsp. lineata
C H A P T E R
41 Stillingia lineata subsp. lineata Nawraj Rummun1, 2, Cla´udia Baider3, Theeshan Bahorun1, Vidushi S. Neergheen-Bhujun1, 2 1
ANDI Centre of Excellence for Biomedical and Biomaterials Research, University of Mauritius, Re´duit, Republic of Mauritius; 2 Department of Health Sciences, Faculty of Science, University of Mauritius, Re´duit, Republic of Mauritius; 3 The Mauritius Herbarium, Agricultural Services, Ministry of Agro-Industry and Food Security, Re´duit, Republic of Mauritius
FIGURE 41 A specimen of Stillingia lineata (A), leaves showing midrib and margin (with an endemic Phelsuma cepediana) (B), inflorescence of S. lineata (C), TLC chromatogram, Lane 1 bottom; rutin, top; quercitrin; Lane 2 bottom; hyperoside, top; quercetin; Lane 3; chlorogenic acid; Lane 4; S. lineata hydromethanolic extract (D); distribution map of S. lineata in sub-Saharan Africa (GBIF, 2018) (E), chemical structure of tonantzitloic acid (F).
Underexplored Medicinal Plants from Sub-Saharan Africa https://doi.org/10.1016/B978-0-12-816814-1.00041-7
267
Copyright © 2020 Elsevier Inc. All rights reserved.
268
41. Stillingia lineata subsp. lineata
1. General description 1.1 Botanical nomenclature Stillingia lineata (Lam.) Mu¨ll. Arg. subsp. lineata
1.2 Botanical family Euphorbiaceae
1.3 Vernacular names Mauritius: Fangame Re´union: Bois de lait; Tanguin de pays
2. Botanical description Shrub to tree up to 12 m high, latex abundant in the bark, branches, and leaves. Branchlet with many leaf scars. Leaves alternated, simple, at branchlet apex, variable, 3e15$( 24) 2e4 cm; blade elliptical, ellipticalobovate, or obovate; base cunated, rounded, or truncate; tip rounded, obtuse, or acute; young leaves more coriaceous and also on smaller plants, becoming more papyraceous with age and on large plants; large and distinct midrib, secondary venation not very visible; margin entire to slightly serrated or crenated, with no gland. Inflorescence terminal, one spike per group of leaves, 2e13 cm long; flowers shortly pedicellated, female flowers at the base, usually solitary, few; male flowers at the apex, many, sometimes all flowers of the inflorescence are male; bract, 1e2 mm thick, variable shape; one visible gland in each side of the base of the inflorescence. Fruit 3 rounded lobes, 5e6 7e8 mm dehiscing explosively. Seeds oblong, 4e5 3e3.5 mm, gray with caruncle (Adapted from Coode, 1982).
3. Distribution S. lineata (Lam.) Mu¨ll. Arg. is found from the South China Sea and Pacific Ocean (subsp. pacifica (Mu¨ll. Arg.) Stennis) to the Indian Ocean (subsp. lineata). The latter subspecies is endemic to Mauritius and Re´union. A relatively common species, on Mauritius, is found across the island as in North mountain range (Le Pouce, Pieter Both), in the Southwest native remnants of Pe´trin, Magenta, Mt Rempart, among others, and the Southeast vegetation of Mt Bambous (Coode, 1982).
7. Pharmacological properties
269
4. Ethnobotanical usage In Mauritius, a bath of the leaf decoction is used to treat skin diseases (Gurib-Fakim and Gue´ho, 1996), whereas in Re´union, the species is used in the treatment of furuncles and more recently against the Chikungunya virus (Dorla et al., 2018).
5. Phytochemical constituents The isolated phytochemicals reported from this subspecies are mainly of terpenoid origin. Tonantzitlolone derivatives having C20-flexibilane and tigliane skeleton, as well as tonantzitloic acid, were reported from the ethyl acetate, leaf extract (Olivon et al., 2015). In addition to the C15flexibilane skeleton tonantzitlolone derivatives, the ethyl acetate extract obtained from the bark also contained the pimarane derivative, ent-12ahydroxy-3,7-dioxoisopimara-8,15-diene (Techer et al., 2015). Thin layer chromatography (TLC) revealed the presence of rutin and chlorogenic acid among the different flavonoid compounds present in S. lineata subsp. lineata hydromethanolic leaf extract.
6. TLC fingerprinting of plant extract The air-dried leaf was extracted with aqueous methanol (80%, v/v) and partitioned with dichloromethane. The aqueous phase was lyophilized, and 5 mg of the powdered extract was dissolved in 1 mL of aqueous methanol (80%, v/v). For the reference standards quercitrin, quercetin, rutin, hyperoside, and chlorogenic acid were purchased from Extrasynthe`se (France), and 1 mg of each standard was dissolved in 1 mL methanol. For the chromatographic separation, 10 mL of extract and 5 mL of reference standard were spotted on a silica gel 60 F254 thin layer chromatography (TLC) plate (20 20 cm). The spots were left to dry, and the plate was placed in a TLC tank, presaturated with 100 mL mobile phase. The mobile phase comprises ethyl acetate, formic acid, and water in ratio 8:1:1 (v/v). The samples were allowed to separate until the solvent front reached about 15 cm from the baseline. The plate was dried and sprayed with 1% methanolic diphenyl boric acid aminoethyl ester (DPBAE) and examined under ultraviolet light at 365 nm to detect the bands on the TLC plates.
7. Pharmacological properties The reported scientific evaluation of its therapeutic potential is limited to in vitro antimicrobial, antidiabetic, and cancer cytotoxicity activities.
270
41. Stillingia lineata subsp. lineata
7.1 Antibacterial activity The ethyl acetate extract of S. lineata leaf showed 2.5-fold higher growth inhibitory activity as compared with the clinical antibiotic, chloramphenicol, against Staphylococcus aureus as determined by the paper disc diffusion method (Dorla et al., 2018).
7.2 Antiviral activity The ethyl acetate extract of S. lineata leaf and bark showed potent antiviral activity against chikungunya virus strain 899 (Olivon et al., 2015; Techer et al., 2015). The leaf extracts further inhibited replication of the human immunodeficiency virus (HIV)-1 and HIV-2 virus (Olivon et al., 2015).
7.3 Cancer cell cytotoxicity Dichloromethane extract of leaf of S. lineata ssp. lineata collected from Mauritius showed cytotoxicity against the human colon carcinoma (Co115) cell line (Chapuis et al., 1988).
7.4 Antidiabetic activity The methanolic extract of S. lineata showed potent inhibitory activity against a-glucosidase enzyme with a 50% inhibitory concentration (IC50) value of 1.0 0.0, 1.8 0.3, and 19.3 3.6 mg/mL, respectively, compared with, the clinically used a-glucosidase inhibitor, acarbose (IC50 of 5115.7 3.9 mg/mL) (Picot et al., 2014). Furthermore, the extract also exhibited a potent glucose diffusion retardation index, highlighting its ability to delay glucose absorption following oral administration (Picot et al., 2014).
8. Additional information 8.1 Therapeutic (proposed) usage Chikungunya virus and antidiabetic
8.2 Safety data The ethyl acetate bark extract was found to be moderately cytotoxic against the host Vero (African green monkey kidney) cells (Techer et al., 2015).
References
271
8.3 Trade information The species would be classified under Least Concerned following the International Union for Conservation of Nature (IUCN) Red List category (IUCN, 2001).
8.4 Dosage Not available
References Chapuis, J.C., Sordat, B., Hostetmann, K., 1988. Screening for cytotoxic activity of plants used in traditional medicine. Journal of Ethnopharmacology 23, 273e284. https://doi.org/10. 1016/0378-8741(88)90006-2. Coode, M.J.E., 1982. 160. Euphorbiace´es. In: Bosser, J., Cadet, T., Gue´ho, J., Marais, W. (Eds.), Flore des Mascareignes e La Reunion, Maurice, Rodrigues. MSIRI/ORSTOM/KEW. Imprimerie du Gouverment, Mauritius. Dorla, E., Grondin, I., Hue, T., Clerc, P., Dumas, S., Gauvin-Bialecki, A., Laurent, P., 2018. Traditional uses, antimicrobial and acaricidal activities of 20 plants selected among Reunion Island’s Flora. South African Journal of Botany. https://doi.org/10.1016/ j.sajb.2018.04.014. GBIF, 2018. Stillingia lineata Mu¨ll.Arg. In GBIF Secretariat (2017). GBIF Backbone Taxonomy. Checklist dataset. https://doi.org/10.15468/39omei. Gurib-Fakim, A., Gueho, J., 1996. Plantes medicinales de Maurice, Tome 2. Editions de l’Ocean Indien, Mauritius. IUCN, 2001. IUCN Red List Categories and Criteria, Version 3.1. IUCN Species Survival Commission, Gland, Switzerland and Cambridge, United Kingdom. Olivon, F., Palenzuela, H., Girard-Valenciennes, E., Neyts, J., Pannecouque, C., Roussi, F., Grondin, I., Leyssen, P., Litaudon, M., 2015. Antiviral activity of flexibilane and tigliane diterpenoids from Stillingia lineata. Journal of Natural Products 78, 1119e1128. https:// doi.org/10.1021/acs.jnatprod.5b00116. Picot, C.M.N., Subratty, A.H., Mahomoodally, M.F., 2014. Inhibitory potential of five traditionally used native antidiabetic medicinal plants on a-amylase, a-glucosidase, glucose entrapment, and amylolysis kinetics in vitro. Advances in Pharmacological Sciences 2014, 1e7. https://doi.org/10.1155/2014/739834. Techer, S., Girard-Valenciennes, E., Retailleau, P., Neyts, J., Gue´ritte, F., Leyssen, P., Litaudon, M., Smadja, J., Grondin, I., 2015. Tonantzitlolones from Stillingia lineata ssp. lineata as potential inhibitors of chikungunya virus. Phytochemistry Letters 12, 313e319. https://doi.org/10.1016/j.phytol.2015.04.023.
41 Stillingia lineata subsp. lineata Nawraj Rummun1, 2, Cla´udia Baider3, Theeshan Bahorun1, Vidushi S. Neergheen-Bhujun1, 2 1
ANDI Centre of Excellence for Biomedical and Biomaterials Research, University of Mauritius, Re´duit, Republic of Mauritius; 2 Department of Health Sciences, Faculty of Science, University of Mauritius, Re´duit, Republic of Mauritius; 3 The Mauritius Herbarium, Agricultural Services, Ministry of Agro-Industry and Food Security, Re´duit, Republic of Mauritius
FIGURE 41 A specimen of Stillingia lineata (A), leaves showing midrib and margin (with an endemic Phelsuma cepediana) (B), inflorescence of S. lineata (C), TLC chromatogram, Lane 1 bottom; rutin, top; quercitrin; Lane 2 bottom; hyperoside, top; quercetin; Lane 3; chlorogenic acid; Lane 4; S. lineata hydromethanolic extract (D); distribution map of S. lineata in sub-Saharan Africa (GBIF, 2018) (E), chemical structure of tonantzitloic acid (F).
Underexplored Medicinal Plants from Sub-Saharan Africa https://doi.org/10.1016/B978-0-12-816814-1.00041-7
267
Copyright © 2020 Elsevier Inc. All rights reserved.
268
41. Stillingia lineata subsp. lineata
1. General description 1.1 Botanical nomenclature Stillingia lineata (Lam.) Mu¨ll. Arg. subsp. lineata
1.2 Botanical family Euphorbiaceae
1.3 Vernacular names Mauritius: Fangame Re´union: Bois de lait; Tanguin de pays
2. Botanical description Shrub to tree up to 12 m high, latex abundant in the bark, branches, and leaves. Branchlet with many leaf scars. Leaves alternated, simple, at branchlet apex, variable, 3e15$( 24) 2e4 cm; blade elliptical, ellipticalobovate, or obovate; base cunated, rounded, or truncate; tip rounded, obtuse, or acute; young leaves more coriaceous and also on smaller plants, becoming more papyraceous with age and on large plants; large and distinct midrib, secondary venation not very visible; margin entire to slightly serrated or crenated, with no gland. Inflorescence terminal, one spike per group of leaves, 2e13 cm long; flowers shortly pedicellated, female flowers at the base, usually solitary, few; male flowers at the apex, many, sometimes all flowers of the inflorescence are male; bract, 1e2 mm thick, variable shape; one visible gland in each side of the base of the inflorescence. Fruit 3 rounded lobes, 5e6 7e8 mm dehiscing explosively. Seeds oblong, 4e5 3e3.5 mm, gray with caruncle (Adapted from Coode, 1982).
3. Distribution S. lineata (Lam.) Mu¨ll. Arg. is found from the South China Sea and Pacific Ocean (subsp. pacifica (Mu¨ll. Arg.) Stennis) to the Indian Ocean (subsp. lineata). The latter subspecies is endemic to Mauritius and Re´union. A relatively common species, on Mauritius, is found across the island as in North mountain range (Le Pouce, Pieter Both), in the Southwest native remnants of Pe´trin, Magenta, Mt Rempart, among others, and the Southeast vegetation of Mt Bambous (Coode, 1982).
7. Pharmacological properties
269
4. Ethnobotanical usage In Mauritius, a bath of the leaf decoction is used to treat skin diseases (Gurib-Fakim and Gue´ho, 1996), whereas in Re´union, the species is used in the treatment of furuncles and more recently against the Chikungunya virus (Dorla et al., 2018).
5. Phytochemical constituents The isolated phytochemicals reported from this subspecies are mainly of terpenoid origin. Tonantzitlolone derivatives having C20-flexibilane and tigliane skeleton, as well as tonantzitloic acid, were reported from the ethyl acetate, leaf extract (Olivon et al., 2015). In addition to the C15flexibilane skeleton tonantzitlolone derivatives, the ethyl acetate extract obtained from the bark also contained the pimarane derivative, ent-12ahydroxy-3,7-dioxoisopimara-8,15-diene (Techer et al., 2015). Thin layer chromatography (TLC) revealed the presence of rutin and chlorogenic acid among the different flavonoid compounds present in S. lineata subsp. lineata hydromethanolic leaf extract.
6. TLC fingerprinting of plant extract The air-dried leaf was extracted with aqueous methanol (80%, v/v) and partitioned with dichloromethane. The aqueous phase was lyophilized, and 5 mg of the powdered extract was dissolved in 1 mL of aqueous methanol (80%, v/v). For the reference standards quercitrin, quercetin, rutin, hyperoside, and chlorogenic acid were purchased from Extrasynthe`se (France), and 1 mg of each standard was dissolved in 1 mL methanol. For the chromatographic separation, 10 mL of extract and 5 mL of reference standard were spotted on a silica gel 60 F254 thin layer chromatography (TLC) plate (20 20 cm). The spots were left to dry, and the plate was placed in a TLC tank, presaturated with 100 mL mobile phase. The mobile phase comprises ethyl acetate, formic acid, and water in ratio 8:1:1 (v/v). The samples were allowed to separate until the solvent front reached about 15 cm from the baseline. The plate was dried and sprayed with 1% methanolic diphenyl boric acid aminoethyl ester (DPBAE) and examined under ultraviolet light at 365 nm to detect the bands on the TLC plates.
7. Pharmacological properties The reported scientific evaluation of its therapeutic potential is limited to in vitro antimicrobial, antidiabetic, and cancer cytotoxicity activities.
270
41. Stillingia lineata subsp. lineata
7.1 Antibacterial activity The ethyl acetate extract of S. lineata leaf showed 2.5-fold higher growth inhibitory activity as compared with the clinical antibiotic, chloramphenicol, against Staphylococcus aureus as determined by the paper disc diffusion method (Dorla et al., 2018).
7.2 Antiviral activity The ethyl acetate extract of S. lineata leaf and bark showed potent antiviral activity against chikungunya virus strain 899 (Olivon et al., 2015; Techer et al., 2015). The leaf extracts further inhibited replication of the human immunodeficiency virus (HIV)-1 and HIV-2 virus (Olivon et al., 2015).
7.3 Cancer cell cytotoxicity Dichloromethane extract of leaf of S. lineata ssp. lineata collected from Mauritius showed cytotoxicity against the human colon carcinoma (Co115) cell line (Chapuis et al., 1988).
7.4 Antidiabetic activity The methanolic extract of S. lineata showed potent inhibitory activity against a-glucosidase enzyme with a 50% inhibitory concentration (IC50) value of 1.0 0.0, 1.8 0.3, and 19.3 3.6 mg/mL, respectively, compared with, the clinically used a-glucosidase inhibitor, acarbose (IC50 of 5115.7 3.9 mg/mL) (Picot et al., 2014). Furthermore, the extract also exhibited a potent glucose diffusion retardation index, highlighting its ability to delay glucose absorption following oral administration (Picot et al., 2014).
8. Additional information 8.1 Therapeutic (proposed) usage Chikungunya virus and antidiabetic
8.2 Safety data The ethyl acetate bark extract was found to be moderately cytotoxic against the host Vero (African green monkey kidney) cells (Techer et al., 2015).
References
271
8.3 Trade information The species would be classified under Least Concerned following the International Union for Conservation of Nature (IUCN) Red List category (IUCN, 2001).
8.4 Dosage Not available
References Chapuis, J.C., Sordat, B., Hostetmann, K., 1988. Screening for cytotoxic activity of plants used in traditional medicine. Journal of Ethnopharmacology 23, 273e284. https://doi.org/10. 1016/0378-8741(88)90006-2. Coode, M.J.E., 1982. 160. Euphorbiace´es. In: Bosser, J., Cadet, T., Gue´ho, J., Marais, W. (Eds.), Flore des Mascareignes e La Reunion, Maurice, Rodrigues. MSIRI/ORSTOM/KEW. Imprimerie du Gouverment, Mauritius. Dorla, E., Grondin, I., Hue, T., Clerc, P., Dumas, S., Gauvin-Bialecki, A., Laurent, P., 2018. Traditional uses, antimicrobial and acaricidal activities of 20 plants selected among Reunion Island’s Flora. South African Journal of Botany. https://doi.org/10.1016/ j.sajb.2018.04.014. GBIF, 2018. Stillingia lineata Mu¨ll.Arg. In GBIF Secretariat (2017). GBIF Backbone Taxonomy. Checklist dataset. https://doi.org/10.15468/39omei. Gurib-Fakim, A., Gueho, J., 1996. Plantes medicinales de Maurice, Tome 2. Editions de l’Ocean Indien, Mauritius. IUCN, 2001. IUCN Red List Categories and Criteria, Version 3.1. IUCN Species Survival Commission, Gland, Switzerland and Cambridge, United Kingdom. Olivon, F., Palenzuela, H., Girard-Valenciennes, E., Neyts, J., Pannecouque, C., Roussi, F., Grondin, I., Leyssen, P., Litaudon, M., 2015. Antiviral activity of flexibilane and tigliane diterpenoids from Stillingia lineata. Journal of Natural Products 78, 1119e1128. https:// doi.org/10.1021/acs.jnatprod.5b00116. Picot, C.M.N., Subratty, A.H., Mahomoodally, M.F., 2014. Inhibitory potential of five traditionally used native antidiabetic medicinal plants on a-amylase, a-glucosidase, glucose entrapment, and amylolysis kinetics in vitro. Advances in Pharmacological Sciences 2014, 1e7. https://doi.org/10.1155/2014/739834. Techer, S., Girard-Valenciennes, E., Retailleau, P., Neyts, J., Gue´ritte, F., Leyssen, P., Litaudon, M., Smadja, J., Grondin, I., 2015. Tonantzitlolones from Stillingia lineata ssp. lineata as potential inhibitors of chikungunya virus. Phytochemistry Letters 12, 313e319. https://doi.org/10.1016/j.phytol.2015.04.023.