A Review of Phytochemistry and Phylogeny that Aid Bio-prospecting in the Traditional Medicinal Plant Genus Ferula L. (Apiaceae) in Iran

Authors

1 Botany Research Division, Research Institute of Forests and Rangelands, Agricultural Research, Education and Extension Organization (AREEO), Tehran, Iran

2 Department of Medicinal Plants, Research Institute of Forests and Rangelands, Agricultural Research, Education and Extension Organization (AREEO), Tehran, Iran

Abstract

Ferula L. as one of the most economically important genera of Apiaceae comprises many species with numerous aromatic and bioactive compounds used in traditional and modern medicine. Based on these features of Ferula that were subject to phytochemical studies, we compare recent molecular phylogenetic findings inferred from nuclear ribosomal internal transcribed spacer (nrDNA ITS) and cpDNA regions (rps16, rpoC1 introns and rpoB-trnC intergenic spacer) with the secondary metabolites inferred from available phytochemical data to investigate the phylogenetic relationships within the Iranian species of the genus. Totally 40 species including six species of Leutea and 34 species of Ferula belonging to three subgenera and seven sections in Iran were examined by phytochemical data that inferred from above 150 publications. Phytochemical compounds were typified in nine groups as 40 binary characters. The last phylogenetic tree was pruned for those Iranian species and the phytochemical data were mapped over. The phytochemical analyses indicate that the major chemical components such as organic sulphur, monoterpen and sesquiterpene compounds have concentrated within five sections of subgen. Narthex of the Ferula genus and the economically important species mostly placed closely within the sections Merwia and Scorodosma.

Keywords

References

1. Cracraft J. The seven great questions of systematic biology: an essential foundation for conservation and the sustainable use of biodiversity. Ann Mo Bot Gard. 2002;89:127–144.
2. Kelly S, Grenyer R, Scotland RW. Phylogenetic trees do not reliably predict feature diversity. Diversity Distrib. 2014;20:600–612.
3. Saslis-Lagoudakis CH, Savolainen V, Williamson EM, Forest F, Wagstaff SJ, Baral SR, et al. Phylogenies reveal predictive power of traditional medicine in bioprospecting. Proc Nat Acad Sci USA. 2012;109:15835–40.
4. Zhu F, Qin C, Tao L, Liu X, Shi Z, Ma X, et al. Clustered patterns of species origins of nature-derived drugs and clues for future bioprospecting. Proc Nat Acad Sci USA. 2011;108:12943–8.
5. Yuan H, Ma Q, Ye L, Piao G. The traditional medicine and modern medicine from natural products. Molecules. 2016;21:1-18.
6. Katiyar C, Gupta A, Kanjilal S, Katiyar S. Drug discovery from plant sources: An integrated approach. AYU. 2012;33:10-19.  
7. Hegnauer R. Chemical patterns and relationships of Umbelliferae, In: Heywood, V.H. (ed.). The Biology and Chemistry of the Umbelliferae. Academic Press INC. London, 1971, pp: 267-276.
8. Crowden RK, Harborne JB, Heywood VH. Chemosystematics of the Umbelliferae- A general survey. Phytochemistry. 1969;8:1963-1984.
9. Katz-Downie DS, Valiejo-Roman CM, Terentieva EI, Troitsky AV, Pimenov MG, Lee B, Downie SR. Towards a molecular phylogeny of Apiaceae subfamily Apioideae: additional information from nuclear ribosomal DNA ITS sequences. Plant Syst Evol. 1999;216:167-195.
10. Zhou J, Peng H, Downie SR, Liu ZW, Gong X. A molecular phylogeny of Chinese Apiaceae subfamily Apioideae inferred from nuclear ribosomal DNA internal transcribed spacer sequences. Taxon. 2008;57:402-416.
11. Christenhusz MJM, Byng JW. The number of known plant species in the world and its annual increase. Phytotaxa. 2016;261:201-217.
12. Mozaffarian V. Umbelliferae. In: Assadi M, Maassoumi AAR, Khatamsaz M, eds. Flora of Iran, Vol. 54. Tehran: Research Institute of Forests and Rangelands, 2007, pp: 1–596.
13. Pimenov MG, Leonov MV. The Asian Umbelliferae biodiversity database (ASIUM) with particular reference to South-West Asian taxa. Turk J Bot. 2004;28:139-145.
14. Mozaffarian V. Identification of medicinal and aromatic plants of Iran. Farhange moaser, Tehran, Iran. 2012
15. Chamberlian DF, Rechinger KH. Ferula L. In: Hedge IC, Lamond JM, Rechinger KH, (eds). Umbelliferae. Flora iranica. Graz: Akademische Druck- und Verlagsanstalt. 1987;162:387–426.
16. Drude CGO. Umbelliferae. In: Engler A, Prantl K. (eds.). Die natürlichen Pflanzenfamilien, Wilhelm Engelmann, Leipzig. 1897-1898;3:63-250.
17. Theobald WL. Comparative anatomical and developmental studies in the Umbelliferae. In: Heywood VH, (ed.). The Biology and Chemistry of the Umbelliferae, Academic Press INC. London. 1971, pp: 177-193.
18. Kurzyna-Młynik R, Oskolski AA, Downie SR, Kopacz R, Wojewódzka A, Spalik K. Phylogenetic position of the genus Ferula (Apiaceae) and its placement in tribe Scandiceae as inferred from nrDNA ITS sequence variation. Plant Syst Evol. 2008;274:47–66.
19. Panahi M, Banasiak Ł, Piwczyński M, Puchałka R, Oskolski AA, Spalik K. Phylogenetic relationships among Dorema, Ferula and Leutea (Apiaceae, Scandiceae, Ferulinae) inferred from nrDNA ITS and cpDNA noncoding sequences. Taxon. 2015;64:770–83.
20. Korovin EP. Generis Ferula (Tourn.) L. monographia illustrata. Tashkent, Uzbekistan: Academiae Scientiarum UzRSS. 1947.
21. Safina LK, Pimenov MG. Karpoanatomicheskiye osobennosti vidov roda Ferula podroda Peucedanoides (Apiaceae) w sviazi s sistematikoy roda. Bot Zh. 1983;68:730–739.
22. Safina LK, Pimenov MG. Feruly Kazakhstana. Alma-Ata: Izdatelstvo "Nauka" Kazakhskoy SSR. 1984.
23. Safina LK, Pimenov MG. Carpology of the species of type subgenus of the Ferula and some problems of their systematics. Feddes Repert. 1990;101:135–151.
24. Panahi M, Banasiak Ł, Piwczyński M, Puchałka R, Kanani MR, Oskolski AA, Modnicki D, Miłobedzka A, Spalik K. Taxonomy of a traditional medicinal plant genus Ferula (Apiaceae) is confounded by incongruence between nuclear rDNA and plastid DNA. Bot J Linn Soc. 2018;188:1-17.
25. Kadereit JW, Bittrich V. (eds.), Flowering Plants. Eudicots, The Families and Genera of Vascular Plants. 15, Springer international publishing AG, 2018, pp: 9-206.
26. Evergetis E, Haroutounian SA. The Umbelliferae (Apiaceae) of Dioscorides annotated in codex Neapolitanus Graecus #1. J Ethnopharmacol. 2015;175:549–566.
27. Korovin EP. Ferula L. In: Vvedensky AI, editor. Flora Uzbekistana. 4. Tashkent: Izdatelstvo Akademii Nauk Uzbekskoi SSR. 1959, pp: 399–438.
28. Amiri MS, Joharchi MR. Ethnobotanical knowledge of Apiaceae family in Iran: A review. Avicenna J Phytomed. 2016;6:621-635.
29. Ajani Y, Bockhoff RC. Ethno botanical interviews on Dorema aucheri Boiss. (Apiaceae), A medicinal species in southern Iran. Int J Environ Sci Nat Res. 2018;12:01-06.
30. Iranshahy M, Iranshahi M. Traditional uses, phytochemistry and pharmacology of asafoetida (Ferula assa-foetida oleo-gum-resin)—A review. J Ethnopharmacol. 2011;134:1–10.
31. Miyazawa N, Nakanishi A, Tomita N, Ohkubo Y, Maeda T, Fujita A. Novel key aroma components of galbanum oil. J Agric Food Chem. 2009;57:1433–1439.
32. Jalili A, Jamzad Z. Red data book of Iran: a preliminary survey of endemic, rare and endangered plant species in Iran. Research Institute of Forests and Rangelands, Tehran, Iran. 1992
33. Amalraj A, Gopi S. Biological activities and medicinal properties of Asafoetida: A review. J Tradit Complement Med. 2017;7:347-359.
34. Iranshahi M, Kalategi F, Rezaee R, Shahverdi AR, Ito C, Furukawa H, Tokuda H, Itoigawa M. Cancer chemopreventive activity of terpenoid coumarins from Ferula species. Planta Med. 2008;74:147–150.
35. Iranshahi M, Sahebkar A, Takasaki M, Konoshima T, Tokuda H. Cancer chemopreventive activity of the prenylated coumarin, umbelliprenin, in vivo. Eur J Cancer Prev. 2009;18:412-415.
36. Barthomeuf C, Lim S, Iranshahi M, Chollet P. Umbelliprenin from Ferula szowitsiana inhibits the growth of human M4Beu metastatic pigmented malignant melanoma cells through cell-cycle arrest in G1 and induction of caspase-dependent apoptosis. Phytomedicine. 2008;15:103-111.
37. Lee CL, Chiang LC, Cheng LH, Liaw CC, Abd El-Razek MH, Chang FR, Wu YC. Influenza A (H1N1) antiviral and cytotoxic agents from Ferula assa-foetida. J Nat Prod. 2009;72:1568–1572.
38. Kelly KJ, Nue J, Camitta BM, Honig GR. Methemoglobinemia in an infant treated with the folk remedy glycerited asafetida. Pediatrics. 1984;73:717-719.
39. Iranshahi M, Rezaee R, Najaf Najafi M, Haghbin A, Kasaian J. Cytotoxic activity of the genus Ferula (Apiaceae) and its bioactive constituents. Avicenna J Phytomed. 2018;8:296-312. 
40. Bianco A, Serrilli AM, Venditti A, Petitto V, Serafini M. Endemic plants of Italy and their peculiar molecular pattern, In: Rahman A, editor. Studies in natural products chemistry. Vol 50. Sapienza – Università di Roma, Rome, Italy, 2016, pp: 215-247.
41.  Sacchetti G, Appendino G, Ballero M, Loy C, Poli F. Vittae fluorescence as a tool to differentiate between poisonous and non-poisonous populations of gaint fennel (Ferula communis) of the island Sardinia (Italy). Biochem Syst Ecol. 2003;31:527-534.
42. Maddison WP, Maddison DR. Mesquite: A modular system for evolutionary analysis. 2019. Version 3.61. Available at: http://mesquiteproject.org.
43. Pimenov MG, Terekhin AT, Devyatkova GN, Baranova IV. Klassifikatsiia vidov roda Ferula L. (Umbelliferae) s pomoshch'iu yerarkhicheskogo klaster-analiza. Voprosy Kibernetiki. 1978;47:98–113.
44. Ahmed AA, Hegazy MEF, Zellagui A, Rhouati S, Mohamed TA, Sayed AA, Abdella MA, Ohta Sh, Hirata T. Ferulsianic acid, a sesquiterpene coumarin with a rare carbon skeleton from Ferula species. Phytochemistry. 2007;68:680-686.
45. Kanani MR, Rahiminejad MR, Sonboli A, Mozaffarian V, Kazempour Osaloo Sh, Nejad Ebrahimi S. Chemotaxonomic significance of the essential oils of 18 Ferula species (Apiaceae) from Iran. Chem Biodivers. 2011;8:503-517.
46. Azarnivand H, Alikhah-Asl M, Jafari M, Arzani H, Amin Gh, Mousavi SS. Comparison of essential oils from Ferula ovina (Boiss.) aerial parts in fresh and dry stages. J Essent Oil-Bear Plants. 2011;14:250-254.
47. Jahansooz F, Ebrahimzadeh H, Najafi AA, Naghavi MR, Talebi Kouyakhi E, Farzaneh H. Composition and antifungal activity of the oil of Ferula gummosa samples from Iran. J Essent Oil-Bear Plants. 2008;11:284-291. 
48. Talebi Kouyakhi E, Naghavi MR, Alayhs M. Study of the essential oil variation of Ferula gummosa samples from Iran. Chem Nat Compd. 2008;44:124-126.
49. Franz C. Genetics, in: Volatil oil crops: Their biology, biochemistry and production, Hay RKM, Waterman PG Eds., Longman, Harlow, UK. 1993, pp: 63.
50. Akhgar MR, Moradalizadeh M, Faghihi-Zarandi A, Rajaei P. Chemical composition of the essential oils of Ferula oopoda (Boiss. & Buhse) Boiss. and Ferula badghysi (Korovin.) from Iran. J Essential Oil-Bear Plants. 2011;14:297-301.
51. Meng H, Li G, Huang J, Zhang K, Wei X, Ma Y, Zhang C, Wang J. Sesquiterpenoid derivatives from Ferula ferulaeoides (Steud.) Korov. Phytochem. 2013;86:151-158.
52. Khamraeva DT, Beshko NY, Abdullayeva AT, Sharipova VK. Structural investigation of the secretory system of some endemic and medicinal species of Apiaceae from Uzbekistan. Iran J Bot. 2018;24:52-64.
53. Ozkan H, Yanmis D, Karadayi M, Bal T, Baris O, Gulluce M. Determination of genotoxic and antigenotoxic properties of essential oil from Ferula orientalis L., using Ames/ Salmonella and E. coli WP2 bacterial test systems. Toxicology and Industrial Health. Toxicol Ind Health. 2012;1-10.
54. Shakeri A, Iranshahy M, Iranshahi M. Biological properties and molecular targets of umbelliprenin – a mini-review. J Asian Nat Prod Res. 2014;16:884-889.
55. Sattar Z, Iranshahi M. Phytochemistry and pharmacology of Ferula persica Boiss.: A review. Iran J Basic Med Sci. 2017;20:1-8.
56. Alipour Z, Taheri P, Samadi N. Chemical composition and antibacterial activity of the essential oils from flower, leaf and stem of Ferula cupularis growing wild in Iran. Pharm Biol. 2015;53:483–487.
57. Karimi N, Salimikia I, Ramak P, Soheilikhah Z, Shamizadeh M, Gholivand MB. Chemical composition, antioxidant and antimicrobial activities of essential oil from Leutea kurdistanica Mozaff. Herb Med J. 2016;1:47-52.
58.  Abbaszadegan A, Gholami A, Mirhadi H, Saliminasab M, Kazemi A, Moein MR. Antimicrobial and cytotoxic activity of Ferula gummosa plant essential oil compared to NaOCl and CHX: a preliminary in vitro study. Restor Dent Endod. 2015;40:50-57.
59. Ahmadvand H, Amiri H, Dehghani Elmi Z, Bagheri Sh. Chemical composition and antioxidant properties of Ferula assa-foetida leaves essential oil. Iran J Pharmacol  Ther. 2013;12:52-57.
60. Daneshkazemi A, Zandi H, Davari A, Vakili M, Emtiazi M, Lotfi R, Masoumi SMR. Antimicrobial activity of the essential oil obtained from the seed and oleo-gum-resin of Ferula assa-foetida against oral pathogens. Front Dent. 2019;16:113-120.
61. Moghadam Matin M, Nakhaeizadeh H, Bahrami AR, Iranshahi M, Arghiani N, Behnam Rassouli F. Ferutinin, an apoptosis inducing terpenoid from Ferula ovina. Asian Pac J Cancer Prev. 2014;15:2123-2128.
62. Sabernavaei M, Kobarfard F, Hadjiakhoondi A, Aghaahmadi M, Amin M, Yassa N. Biological evaluation of the isolated compounds from methanol fraction of Leutea avicennia Mozaff. Iran J Pharm Res. 2018;17:1386-1391.
63. Iqbal J, Abbasi BA, Mahmood T, Kanwal S, Ali B, Shah SA, Khalil AT. Plant-derived anticancer agents: A green anticancer approach. Asian Pac. J Trop Biomed. 2017;7:1129-1150.  
64. Gertsch J. How scientific is the science in ethnopharmacology? Historical perspectives and epistemological problems. J. Ethnopharmacol. 2009;122:177–183.
65. Gliszczyńska A, Brodelius PE. Sesquiterpene coumarins. Phytochem. Rev. 2012;11:77-96.
Journal of Medicinal plants and By-product
Volume 9, Issue 2
September 2020
Pages 133-148

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