Pyrrolizidine Alkaloids and their Biological Properties from Indian Heliotropium Species

Author(s): Bharat Singh*, Ram A. Sharma.

Journal Name: Current Bioactive Compounds

Volume 15 , Issue 1 , 2019

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Graphical Abstract:


Abstract:

Background: Pyrrolizidine alkaloids (PAs) are a group of plant secondary metabolites which protect the plants from biotic stresses by stimulating defense mechanisms as well as adaptability. The pyrrolizidine alkaloids widely occur in members of Boraginaceae family. This review paper describes about the structural properties of various PAs isolated from various Indian Heliotropium species and their biological and pharmacological activities.

Methods: Authors surveyed the per-reviewed research, review papers and bibliographic databases and incorporated in this review paper. We have focused our attention on the answers of reviewed questions. The main themes and characteristics of reviewed papers have been described in this review paper.

Results: Twenty three species of Heliotropium genus were reviewed critically and have included in this review paper. The review paper contains the critical information of ethnomedicinal properties of each species of Heliotropium genus, the occurrence of pyrrolizidine alkaloids, the biological and pharmacological properties of pyrrplizidine alkaloids. So many pyrrolizidine alkaloids and their N-oxides possess anticancer activity. Some PAs have demonstrated cytotoxic effects also.

Conclusion: The findings of this review paper validate the significance of pyrrolizidine alkaloids, their occurrence and biosynthesis in Heliotropium species, as well as their biological and pharmacological properties.

Keywords: Pyrrolizidine alkaloids, Heliotropium species, Boraginaceae, anticancer activity, hepatotoxic properties, open chain diester.

[1]
Li, N.; Xia, Q.; Ruan, J.; Fu, P.P.; Lin, G. Hepatotoxicity and tumorigenicity induced by metabolic activation of pyrrolizidine alkaloids in herbs. Curr. Drug Metab., 2011, 12(9), 823-834.
[2]
Carlson, T.J.S. Medical ethnobotanical research as a method to identify bioactive plants to treat infectious diseases. Adv. Phytomed., 2002, 1, 45-53.
[3]
Dey, A.; De, J.N. Neuroprotective therapeutics from botanicals and phytochemicals against Huntington’s disease and related neurodegenerative disorders. J. Herb. Med., 2015, 5, 1-19.
[4]
Robertson, J.; Stevens, K. Pyrrolizidine alkaloids – a review. Nat. Prod. Rep., 2017, 34, 62-89.
[5]
Batra, P.; Sharma, A.K. Anticancer potential of flavonoids: recent trends and future perspectives. 3 Biotech, 2013. 3, 439-459.
[6]
Shaked, Y.; Emmenegger, U.; Francia, G.; Chen, L.; Lee, C.R.; Man, S.; Paraghamian, A.; Ben-David, Y.; Kerbel, R.S. Low-dose metronomic combined with intermittent bolus-dose cyclophosphamide is an effective long-term chemotherapy treatment strategy. Cancer Res., 2005, 65(16), 7045-7051.
[7]
Treasure, T.; Fallowfield, L.; Farewell, V.; Ferry, D.; Lees, B.; Leonard, P.; Macbeth, F.; Utley, M. Pulmonary metastasectomy in colorectal cancer: time for a trial. Eur. J. Surg. Oncol., 2009, 35(7), 686-689.
[8]
Bull, L.B.; Culvenor, C.C.J.; Dick, A.T. The Pyrrolizidine Alkaloids: their Chemistry, Pathogenicity and other Biological Properties; North-Holland Publ: Amsterdam, 1968.
[9]
Bull, L.B.; Culvenor, C.C.; Dick, A.T. The Pyrrolizidine Alkaloids; North Holland Publishing Co: Amsterdam, 1968.
[10]
Mattocks, A.R. Chemistry and Toxicology of Pyrrolizidine Alkaloids; Academic Press: New York, London, 1986.
[11]
Rizk, A.M. The Pyrrolizidine Alkaloids: Plant Sources and Properties. In: Naturally Occurring Pyrrolizidine Alkaloids; Rizk, A.M., Ed.; CRC Press Inc: Boca Raton, 1991; pp. 1-89.
[12]
Roeder, E. Toxicology of pyrrolizidine alkaloids. Pharmazie, 2000, 55, 711-726.
[13]
Robins, D.J. Biosynthesis of Pyrrolizidine and Quinolizidine Alkaloids. The alkaloids. Chemistry and Pharmacology., 1995, Vol 46, 1-62.
[14]
Liddell, J.R. Pyrrolizidine alkaloids. Nat. Prod. Rep., 2002, 19(6), 773-781.
[15]
Sharma, R.A.; Singh, B.; Singh, D.; Chandrawat, P. Ethnomedicinal, pharmacological properties and chemistry of some medicinal plants of Boraginaceae in India. J. Med. Plants Res., 2009, 3, 1153-1175.
[16]
Hartmann, T.; Ober, D. Biosynthesis and metabolism of pyrrolizidine alkaloids in plants and specialized insect herbivores. Biosynthesis: Topics in Current Chemistry., 2000, Vol 299, 207-243.
[17]
Böttcher, F.; Ober, D.; Hertmann, T. Biosynthesis of pyrrolizidine alkaloids: putrescine and spermidine are essential substrates of enzymatic homospermidine formation. Can. J. Chem., 1994, 72, 80-85.
[18]
Robins, D.J. Biosynthesis of pyrrolizidine alkaloids. Chem. Soc. Rev., 1989, 18, 375-408.
[19]
Schoental, R.; Mattocks, A.R. Hepatotoxic activity of semi-synthetic analogues of pyrrolizidine alkaloids. Nature, 1960, 185, 842-843.
[20]
Culvenor, C.C.J.; Edgar, J.A.; Jago, M.V.; Qutteridge, A.; Peterson, J.E.; Smith, L.W. Hepato- and pneumotoxicity of pyrrolizidine alkaloids and derivatives in relation to molecular structure. Chem. Biol. Interact., 1976, 12(3-4), 299-324.
[21]
Mattocks, A.R.; White, I.N.H. Pyrrolic metabolites from non-toxic pyrrolizidine alkaloids. Nat. New Biol., 1971, 231(21), 114-115.
[22]
Roeder, E.; Wiedenfeld, H. Pyrrolizidine alkaloids in medicinal plants of Mongolia, Nepal and Tibet. Pharmazie, 2009, 64(11), 699-716.
[23]
Roeder, E. Medicinal plants in Europe containing pyrrolizidine alkaloids. Pharmazie, 1995, 50(2), 83-98.
[24]
Prakash, A.S.; Pereira, T.N.; Reilly, P.E.; Seawright, A.A. Pyrrolizidine alkaloids in human diet. Mutat. Res., 1999, 443(1-2), 53-67.
[25]
Dell, B.; Comb, J. Plants resins, their function, secretion and possible function. Adv. Bot. Res., 1979, 6, 277-316.
[26]
Chopra, R.N.; Nayar, S.L.; Chopra, I.C. Glossary of Indian Medicinal Plants; CSIR: New Delhi, 1956.
[27]
Kirtikar, K.R.; Basu, B.D. Indian Medicinal Plants; Popular Book Depot: Bombay, 1967.
[28]
Shafi, M.S.; Ashraf, M.Y.; Sarwar, G. Wild medicinal plants of Cholistan area of Pakistan. Pak. J. Biol. Sci., 2001, 4, 112-116.
[29]
Pullaiah, T. Encyclopedia of World Medicinal Plants; Regency Publications: New Delhi, 2006.
[30]
Jain, S.C.; Sharma, R. Antimicrobial activity of pyrrolizidine alkaloids from Heliotropium ellipticum. Chem. Pharm. Bull., 1987, 35(8), 3487-3489.
[31]
Jain, S.C.; Singh, B. Bioefficacy of Heliotropium ellipticum Ledeb. I. antimicrobial screening. Indian J. Pharm. Sci., 1998, 60, 394-396.
[32]
Jain, S.C.; Singh, B.; Jain, R. Antimicrobial activity of triterpenoids from Heliotropium ellipticum. Fitoterapia, 2001, 72(6), 666-668.
[33]
Singh, B.; Sharma, R.A. Anti-inflammatory and antimicrobial effects of flavonoids from Heliotropium ellipticum exudates. Curr. Bioact. Compd., 2016, 12, 123-131.
[34]
Ali, A.; Uddin, J.; Ansar, H.N.; Firdou, S.; Musharaff, S.G. Electrospray tandem mass spectrometric study of a furo-furan lactone in Heliotropium eichwaldi. J. Chromatogr. Sep. Tech., 2015, 6, 1-9.
[35]
Sharma, S.K.; Goyal, N. Protective effect of Heliotropium eichwaldi against cisplatin-induced nephrotoxicity in mice. J. Chin. Integr. Med., 2012, 10(5), 555-560.
[36]
Gandhi, R.N.; Rajagopalan, T.R.; Seshadri, T.R. Chemical components of Heliotropium eichwaldi. Curr. Sci., 1965, 35, 121-122.
[37]
Suri, O.P.; Sawhney, R.S.; Atal, C.K. Pyrrolizidine alkaloids from Heliotropium eichwaldii and Lindelofia spectabilis. Indian J. Chem., 1975, 13, 505-506.
[38]
Holm, L.; Doll, J.; Holm, E.; Pancho, J.; Herberger, J. World Weeds: Natural Histories and Distribution; John Wiley & Sons Inc.: New York, 1997.
[39]
Rao, B.H.; Kumar, K.V. Structure, distribution and taxonomic significance of foliar crysalliforms inclusions in Boraginaceae. In: Gleanings in Plant Sciences; Swami, N.R.; Reddy, N.P.; Pulaiah, T.; Murthy, G.V.S.; Rao, G.P., Eds.; Regency Publications: New Delhi, 2004; pp. 67-72.
[40]
Ghazanfar, S.A. Hnadbook of Arabian Medicinal Plants; CRC Press: Boca Raton, 1994.
[41]
Qureshi, R.; Bhatti, G.R.; Memon, R.A. Ethnomedicinal uses of herbs from Northern part of Nara Desert, Pakistan. Pak. J. Bot., 2010, 42, 839-851.
[42]
Safa, O.; Soltanipoor, M.A.; Rastegar, S.; Kazemi, M.; Nourbakhsh Dehkordi, K.; Ghannadi, A. An ethnobotanical survey on hormozgan province, Iran. Avicenna J. Phytomed., 2013, 3(1), 64-81.
[43]
Pass, D.A.; Hogg, G.G.; Russell, R.G.; Edgar, J.A.; Tence, I.M.; Rikard-Bell, L. Poisoning of chickens and ducks by pyrrolizidine alkaloids of Heliotropium europaeum. Aust. Vet. J., 1979, 55, 284-288.
[44]
Simonsen, H.T.; Nordskjold, J.B.; Smitt, U.W.; Nyman, U.; Palpu, P.; Joshi, P.; Varughese, G. In vitro screening of Indian medicinal plants for antiplasmodial activity. J. Ethnopharmacol., 2001, 74(2), 195-204.
[45]
Qureshi, R.; Raza Bhatti, G. Ethnobotany of plants used by the Thari people of Nara Desert, Pakistan. Fitoterapia, 2008, 79(6), 468-473.
[46]
Bull, L.B.; Dick, A.T.; Keast, J.C.; Edgar, G. An experimental investigation of the hepatotoxic and other effects on sheep of consumption of Heliotropium europaeum L.: Heliotrope poisoning of sheep. Crop Pasture Sci., 1956, 7, 281-32.
[47]
O’Dowd, D.J.; Edgar, J.A. Seasonal dynamics in the pyrrolizidine alkaloids of Heliotropium europaeum. Aust. J. Ecol., 1989, 14, 95-105.
[48]
Culvenor, C.C.J. Alkaloids of Heliotropium europaeum. II isolation and structures of the third major alkaloid and two minor alkaloids and isolations of the principal Noxides. Aust. J. Chem., 1954, 7, 287-297.
[49]
Culvenor, C.C.J.; Drummond, J.L.; Price, J.R. Alkaloids of Heliotropium europaeum. I. Heliotrine and lasiocarpine. Aust. J. Chem., 1954, 7, 277-280.
[50]
Tosun, F.; Tamer, U. Determination of pyrrolizidine alkaloids in the seeds of Heliotropium europaeum by gc-ms. J. Fac. Pharm. Ankara, 2004, 33, 7-9.
[51]
Saeedi, M.; Morteza-Semnani, K. Chemical composition and antimicrobial activity of the essential oil of Heliotropium europaeum. Chem. Nat. Compd., 2009, 45, 98-99.
[52]
Kakar, F.; Akbarian, Z.; Leslie, T.; Mustafa, M.L.; Watson, J.; van Egmond, H.P.; Omar, M.F.; Mofleh, J. An outbreak of hepatic veno-occlusive disease in Western afghanistan associated with exposure to wheat flour contaminated with pyrrolizidine alkaloids. J. Toxicol., 2010, 2010, 313280.
[53]
Culvenor, C.C.J.; Smith, L.W. A quaternary N-dihydropyrrolizinomethyl derivative of heliotrine from Heliotropium europaeum. Tetrahedron Lett., 1969, 10, 3603-3606.
[54]
Culvenor, C.C.J.; Johns, S.R.; Smith, L.W. Acetyllasiocarpine, an alkaloid from Heliotropium europaeum. Aust. J. Chem., 1975, 28, 2319-2322.
[55]
Peterson, J.E.; Payne, A.; Culvenor, C.C.J. Heliotropium europaeum poisoning of sheep with low liver copper concentrations and the preventive efficacy of cobalt and antimethanogen. Aust. Vet. J., 1992, 69(3), 51-56.
[56]
Shimshoni, J.A.; Mulder, P.P.; Bouznach, A.; Edery, N.; Pasval, I.; Barel, S.; Abd-El Khaliq, M.; Perl, S. Heliotropium europaeum poisoning in cattle and analysis of its pyrrolizidine alkaloid profile. J. Agric. Food Chem., 2015, 63(5), 1664-1672.
[57]
Yassa, N.H.; Farsam, H.; Rustaiyan, A.; Shafiee, A. Alkaloids of Boraginaceae II (1) Pyrrolizidine alkaloids of Heliotropium europaeum L, population Garmsar. J. Sci. Islamic Repub. Iran, 1999, 10, 39-42.
[58]
Cavallaro, V.; Than, K.A.; Colegate, S.M.; Edgar, J.A. An indirect competitive ELISA for pyrrolizidine alkaloids of Heliotropium europaeum. In: Poisonous Plants and Related Toxins; Acamovic, T.; Stewart, C.S.; Pennycott, T.W., Eds.; CABI Publishing: Cambridge, 2004; pp. 114-119.
[59]
Wiedenfeld, H.; Edgar, J. Toxicity of pyrrolizidine alkaloids to humans and ruminants. Phytochem. Rev., 2011, 10, 137-151.
[60]
Khatamsaz, M. Flora of Iran: Boraginaceae; Research Institute of Forests and Rangelands: Tehran, 2002.
[61]
Akhani, H. Diversity, biogeography and photosynthetic pathwaysof Argusia and Heliotropium (Boraginaceae) in South-West Asia with an analysis of phytogeographical units. Bot. J. Linn. Soc., 2007, 155, 401-425.
[62]
Dasti, A.A.; Bokhari, T.Z.; Malik, S.A.; Akhtar, R. Epidermal morphology in some members of family Boraginaceae in Balochistan. Asian J. Plant Sci., 2003, 2, 42-47.
[63]
Tareen, R.B.; Bibi, T.; Khan, M.A.; Ahmad, M.; Zafar, M.; Hina, S.; Khalil-ur-Rehman, Z.U.H.; Dogar, N.J.; Hameed, M.; Khan, Z.I. Indigenous knowledge of folk medicine by the women of Kalat and Khuzdar regions of Balochistan, Pakistan. Pak. J. Bot., 2010, 42, 1465-1485.
[64]
Ghaffari, M.A.; Bano, S.; Hayat, K. Antimicrobial and phytotoxic effects of the plant Heliotropium dasycarpum L. Int. J. Pharm. BioSci., 2013, 4, 339-445.
[65]
Ghaffari, M.A.; Chaudhary, B.A.; Uzair, M.; Ashfaq, K. Cytotoxic, α-chymotrypsin and urease inhibition activities of the plant Heliotropium dasycarpum L. Afr. J. Tradit. Complement. Altern. Med., 2016, 13(6), 194-198.
[66]
Stegelmeier, B.L. Pyrrolizidine alkaloids containing toxic plants (Senecio, Crotalaria, Cynoglossum, Amsinckia, Heliotropium, Echium spp). Vet. Clin. North Am. Food Anim. Pract., 2011, 27(2), 419-428. [ix.].
[67]
Sadikov, A.Z.; Shakirov, T.T. Methods of obtaining heliotrine from epigeal part of Heliotropium dasycarpum. Chem. Nat. Compd., 1986, 22, 80-82.
[68]
Akramov, S.T.; Kiyamitdinova, F.; Yunusov, S.Y. Alkaloids of Rindera cyclodonata, Rinderia echinata and Heliotropium dasycarpum. Khim. Prir. Soedin., 1967, 3, 288-289.
[69]
Akramov, S.; Shadmanov, Z.; Samatov, A.; Yunusov, S.Y. Alkaloids of Senecio jacobea, Heliotropium acutiflorum and H. transoxanum. Chem. Nat. Compd., 1968, 4, 221-222.
[70]
Delnavazi, M.R.; Banihashem, M.; Farsam, H.; Shafiee, A.; Yassa, N. Pyrrolizidine alkaloids from Heliotropium transoxanum Bunge. Res. J. Pharmacog., 2016, 3, 1-5.
[71]
Pullaiah, T.; Naidu, K.C. Antidiabetic Plants in India and Herbal Based Antidiabetic Research; Regency Publ: New Delhi, 2003, p. 196.
[72]
Nasir, E.; Ali, S.I. Flora of Pakistan; University of Karachi: Karachi, 2005.
[73]
Verdcourt, B. Boraginaceae. In: Flora of Tropical East Africa; Polhill, R.M., Ed.; AA Balkema: Rotterdam, The Netherlands, 1991.
[74]
Martins, E.S.; Brummitt, R.K. Boraginaceae. In: Flora Zambesiaca; Launnert, E.; Pope, G.V., Eds.; Management Committee: London, 1990.
[75]
Burkill, H.M. The Useful Plants of West Tropical Africa; Royal Botanic Gardens: Kew, UK, 1985.
[76]
Aswal, B.S.; Bhakuni, D.S.; Goel, A.K.; Kar, K.; Mehrotra, B.N. Screening of Indian plants for biological activity. Part X. Indian J. Exp. Biol., 1984, 22, 312-332.
[77]
Jain, S.K.; Defillips, R.A. Medicinal Plants of India; Reference Publications: Michigan, 1991.
[78]
Ruffo, C.K.; Birnie, A.; Tengnäs, B. Edible Wild Plants of Tanzania. Technical Handbook No. 27; Regional Land Management Unit/SIDA: Nairobi, Kenya, 2002.
[79]
Neuwinger, H.D. African Traditional Medicine: a Dictionary of Plant Use and Applications; MedPharm Scientific: Stuttgart, 2000.
[80]
Schmelzer, G.H.; Gurib-Fakim, A. Plant Resources of Tropical Africa 11(1). Medicinal Plants 1; PROTA Foundation/Backhuys Publishers/CTA: Wageningen, The Netherlands. , 2008.
[81]
Singh, B.; Sahu, P.M.; Singh, S. Antimicrobial activity of pyrrolizidine alkaloids from Heliotropium subulatum. Fitoterapia, 2002, 73(2), 153-155.
[82]
Malik, A.; Rahman, K. Stereostructure of subulacine-N-oxide: a new pyrrolizidine alkaloid from Heliotropium subulatum. Heterocycles, 1988, 27, 707-711.
[83]
Stermitz, F.R.; L’Empereur, K.M. Identity of subulacine N-oxide with 1β, 2β-epoxy-1α-hydroxymethyl-8α-pyrrolizidine. Tetrahedron Lett., 1988, 29, 4943-4944.
[84]
Reina, M.; Gonzalez Coloma, A.; Gutirrez, C.; Cabrera, R.; Henriquez, J.; Villarroel, L. Bioactive saturated pyrrolizidine alkaloids from Heliotropium floridum. Phytochemistry, 1997, 46, 845-853.
[85]
Ghori, M.K.; Ghaffari, M.A.; Hussain, S.N.; Manzoor, M.; Aziz, M.; Sarwer, W. Ethnopharmacological, phytochemical, and pharmacognostic potential of genus Heliotropium L. Turkish J. Pharm. Sci., 2016, 13, 259-280.
[86]
Goyal, N.; Sharma, S.K. Bioactive phytoconstituents and plant extracts from genus. Heliotropium. Int. J. Green Pharm., 2014, 8, 217-225.
[87]
Bussmann, R.W.; Sharon, D. Medicinal Plants of Andes and the Amazon. The Magic and Medicinal Flora of Northern Peru; Graficart Srl: Trujillo, Peru, 2015.
[88]
Reina, M.; Gonzalez-Coloma, A.; Gutierrez, C.; Cabrera, R.; Henriquez, J.; Villarroel, L. Pyrrolizidine alkaloids from Heliotropium megalanthum. J. Nat. Prod., 1998, 61(11), 1418-1420.
[89]
Farsam, H.; Yassa, N.; Sarkhail, P.; Shafiee, A. New pyrrolizidine alkaloids from Heliotropium crassifolium. Planta Med., 2000, 66(4), 389-391.
[90]
Mroczek, T.; Glowniak, K.; Wlaszczyk, A. Simultaneous determination of N-oxides and free bases of pyrrolizidine alkaloids by cation-exchange solid-phase extraction and ion-pair high-performance liquid chromatography. J. Chromatogr. A, 2002, 949(1-2), 249-262.
[91]
Liddell, J.R. Pyrrolizidine alkaloids. Nat. Prod. Rep., 2000, 17(5), 455-462.
[92]
Aniszewski, T. Alkaloids: Chemistry, Biology, Ecology and Applications; Elsevier: Amsterdam, The Netherlands, 2015.
[93]
Ajibesin, K.K. Ethnobotanicalsurvey of plants used for skin diseases and related ailments in Akwa Ibom state of Nigeria. Ethnobot. Res. Appl., 2012, 10, 463-522.
[94]
Hammad, E.A.F.; Zeaiter, A.; Saliba, N.; Talhouk, S. Bioactivity of indigenous medicinal plants against the cotton whitefly, Bemisia tabaci. J. Insect Sci., 2014, 14, 105.
[95]
Asibal, C.F.; Gelbaum, L.T.; Zalkow, L.H. Pyrrolizidine alkaloids from Heliotropium rotundifolium. J. Nat. Prod., 1989, 52(4), 726-731.
[96]
Muthu, C.; Ayyanar, M.; Raja, N.; Ignacimuthu, S. Medicinal plants used by traditional healers in Kancheepuram district of Tamil Nadu, India. J. Ethnobiol. Ethnomed., 2006, 2, 43.
[97]
Zalkow, L.H.; Gelbaum, L.; Keinan, E. Isolation of the pyrrolizidine alkaloid europine-N-oxide from Heliotropium maris-mortui and H. rotundifolium. Phytochemistry, 1978, 17, 172.
[98]
Anonymous, The Wealth of India., 1985. 29-30.
[99]
Dash, G.K.; Abdullah, M.S. A review on Heliotropium indicum L. (Boraginaceae). Int. J. Pharm. Sci. Res., 2013, 4, 1253-1258.
[100]
Ayensu, E.S. Medicinal plants of the West Indies. J. Pharm. (Cairo), 1978, 1, 100.
[101]
Nagaraju, N.; Rao, K.N. A survey of plant crude drugs of Rayalaseema, Andhra Pradesh, India. J. Ethnopharmacol., 1990, 29(2), 137-158.
[102]
Barrett, B. Medicinal plants of Nicaraguas Atlantic coast. Econ. Bot., 1994, 48, 8-20.
[103]
Anderson, G.; Coee, F. Ethanobotany of the garifuna of East Nicaragua. Econ. Bot., 1996, 50, 71-107.
[104]
Rao, R.P.; Nammi, S.; Raju, A.D.V. Studies on the antimicrobial activity of Heliotropium indicum Linn. J. Nat. Rem., 2002, 2, 195-198.
[105]
Theeraphan, M.; John, K.; Boonsom, L.; Saisunee, L.; Stephen, P.G. Composition and antituberculosis activity of the volatile oil of Heliotropium indicum Linn. Growing in Phitsanulok, Thailand. Flavour Fragrance J., 2006, 21, 265-267.
[106]
Ohnuma, T.; Sridhar, K.S.; Ratner, L.H.; Holland, J.F. Phase I study of indicine N-oxide in patients with advanced cancer. Cancer Treat. Rep., 1982, 66(7), 1509-1515.
[107]
Roy, A. Pharmacological activities of Indian heliotrope (Heliotropium indicum L.): a review. J. Pharmacog. Phytochem., 2015, 4, 101-104.
[108]
Adelaja, A.A.; Ayoola, M.D.; Otulana, J.O.; Akinola, O.B.; Olayiwola, A.; Ejiwunmi, A.B. Evaluation of the histo - gastroprotective and antimicrobial activities of heliotropium indicum linn (boraginaceae). Malays. J. Med. Sci., 2008, 15(3), 22-30.
[109]
Boye, A.; Koffuor, G.A.; Ameyaw, E.O.; Abaitey, A.K. Analgesic activity and safety assessment of Heliotropium indicum L. (Boraginaceae) in rodents. Int. J. Pharmacol., 2012, 8, 91-100.
[110]
Veda Vijaya, T.; Sasi Kumar, S.; Asokan, B.R.; Sengottuvelu, S.; Jaikumar, S. Anticataract activity of ethanolic extract of Heliotropium indicum leaves on galactose induced cataract in rats. Int. J. Pharmacol. Toxicol., 2015, 5, 18-20.
[111]
Savadi, R.; Alagawadi, K.; Darade, S. Antifertility activity of ethanolic extract and its n-hexane and benzene fractions of Heliotropium indicum leaves on albino rats. J. Pharm. Res., 2009, 2, 927-930.
[112]
Reddy, J.S.; Rao, P.R.; Reddy, M.S. Wound healing effects of Heliotropium indicum, Plumbago zeylanicum and Acalypha indica in rats. J. Ethnopharmacol., 2002, 79(2), 249-251.
[113]
Yeo, D.; Barthélémy, A.; Christine, L.; Metowogo, K.; N’guessan, J.D.; Allico, D.J. Isolation of wound healing compounds from Heliotropium indicum. J. Appl. Pharm. Sci., 2011, 1, 102-106.
[114]
Dash, G.K.; Murthy, P.N. Studies on wound healing activity of Heliotropium indicum Linn. leaves on rats. ISRN Pharmacol., 2011, 2011, 847980.
[115]
Srinivas, K.; Rao, M.E.; Rao, S.S. Anti-inflammatory activity of Heliotropium indicum Linn. And Leucas aspera Spreng. In albino rats. Indian J. Pharmacol., 2000, 32, 37-38.
[116]
Betanabhatla, K.S.; Jasmin Sajni, R.; Raamamurthy, J.; Christina, A.J.; Sasikumar, S. Anti-inflammatory and anyinociceptive activities of Heliotropium indicum Linn. In experimental animal models. Pharmacologyonline, 2007, 3, 438-445.
[117]
Bero, J.; Ganfon, H.; Jonville, M-C.; Frédérich, M.; Gbaguidi, F.; DeMol, P.; Moudachirou, M.; Quetin-Leclercq, J. In vitro antiplasmodial activity of plants used in Benin in traditional medicine to treat malaria. J. Ethnopharmacol., 2009, 122(3), 439-444.
[118]
Rahman, M.; Mia, M.; Shahid, I. Pharmacological and phytochemical screen activities of roots of Heliotropium indicum Linn. Pharmacologyonline, 2011, 1, 185-192.
[119]
Pandey, D.P.; Singh, J.P.; Roy, R.; Singh, V.P.; Pandey, V.B. Constituents of Heliotropium indicum. Orient. J. Chem., 1996, 12, 321-322.
[120]
Mattocks, A.R. Minor alkaloids of H. indicum. J. Chem. Soc., 1967, 1967, 329.
[121]
Mattocks, A.R.; Schoental, R.; Crowley, H.C.; Culvenor, C.C.J. Indicine: The Major alkaloid of Heliotropium indicum L. J. Chem. Soc., 1961, 1961, 5400.
[122]
Dutta, S.K.; Sanyal, U.; Chakraborty, S.K. A modified method of isolation of Indicine-N-Oxide from H. indicum and its antitumor activity against ehrlich ascites carcinoma and sarcoma-180. Indian J. Cancer Chem., 1987, 9, 73-77.
[123]
Kugelman, M.; Liu, W.C.; Axelrod, M.; McBride, T.J.; Rao, K.V. Indicine-N-oxide: the antitumor principle of Heliotropium indicum. Lloydia, 1976, 39(2-3), 125-128.
[124]
Birecka, H.; Frohlich, M.W.; Glickman, L.M. Free and esterified necines in Heliotropium species from Mexico and Texas. Phytochemistry, 1983, 22, 1167-1171.
[125]
Hoque, M.S.; Ghani, A.; Rashid, H. Alkaloids of Heliotropium indicum grown in Bangladesh. Pharm. J., 1976, 5, 13.
[126]
Pandey, V.B.; Singh, J.P.; Rao, Y.V.; Acharya, S.B. Isolation and pharmacological action of heliotrine, the major alkaloid of Heliotropium indicum seeds. Planta Med., 1982, 45(4), 229-233.
[127]
Osungunna, M.O.; Adedeji, K.A. Phytochemical and antimicrobial screening of methanol extract of Heliotropium indicum leaf. J. Microbiol. Antimicrob., 2011, 3, 213-216.
[128]
Birecka, H.; Frohlich, M.W.; Hull, L.; Chaskes, M.J. Pyrrolizidine alkaloids of Heliotropium from Mexico and adjacent U.S.A. Phytochemistry, 1980, 19, 421-426.
[129]
Souza, J.S.N.; Machado, L.L.; Pessoa, O.D.L.; Braz-Filho, R.; Overk, C.R.; Yao, P.; Cordell, G.A.; Lemos, T.L.G. Pyrrolizidine alkaloids from Heliotropium indicum. J. Braz. Chem. Soc., 2000, 16, 1410-1414.
[130]
Dick, A.T.; Dann, A.T.; Bull, L.B.; Culvenor, C.C.J. Vitamin B12 and the detoxification of hepatotoxic pyrrolizidine alkaloids in rumen liquor. Nature, 1963, 197, 207-208.
[131]
Dattagupta, S.; Datta, P.C. Pharmacognostic study of the leaf of Heliotropium indicum Linn. (Boraginaceae). J. Crude Drug Res., 1977, 15, 141-151.
[132]
Frölich, C.; Ober, D.; Hartmann, T. Tissue distribution, core biosynthesis and diversification of pyrrolizidine alkaloids of the lycopsamine type in three Boraginaceae species. Phytochemistry, 2007, 68(7), 1026-1037.
[133]
Oluwatoyin, S.M.; Illeogbulam, N.G.; Joseph, A. Phytochemical and antimicrobial studies on the aerial parts of Heliotropium indicum Linn. Ann. Biol. Res., 2011, 2, 129-136.
[134]
Begum, Y. Antibacterial, antioxidant and cytotoxic activities of Heliotropium indicum. Experiment, 2014, 23, 1564-1569.
[135]
Ahmad, S.; Ahmad, S.; Bibi, I.; Ishaq, M.S.; Afridi, M.S.; Kanwal, F.; Zakir, M.; Fatima, F. Phytochemical analysis, antioxidant activity, fatty acids com-position and functional group analysis of Heliotropium bac-ciferum. Sci. World J.,, 2014, 2014
[136]
Ahmad, S. AbdEl-Salem, N.M.; Ullah, R. In vitro antimicrobial bioassays, DPPH scavenging activity, FTIR spectroscopy analysis of Heliotropium bacciferum. BioMed Res. Int., 2016, 2016, 3818945.
[137]
Middleditch, B.S.; Amer, A.M. Kuwaiti Plants: Distribution, Traditional Medicine, Pytochemistry, Pharmacology and Economic Value; Elsevier Science: Burlington, 1991.
[138]
Farrag, N.M.; Abdel-Aziz, E.M.; El-Shafae, A.M.; Ateya, A.M.; El-Domiaty, M.M. Pyrrolizidine alkaloids of Heliotropium bacciferum Forssk from Egypt. Int. J. Pharmacol., 1996, 34, 374-377.
[139]
Schoental, R. Hepatotoxic action of pyrrolizidine (Senecio) alkaloids in relation to their structure. Nature, 1957, 179(4555), 361-363.
[140]
Ahmad, S.; Ahmad, S.; Bibi, I. AbdEl-Salem, N.M.; Hussain, H.; Ishaq, M.S.; Adnan, M.; Tariq, A.; Ullah, R. Antibacterial and antifungal activities of the extract and fractions of aerial parts of Heliotropium bacciferum. Afr. J. Tradit. Complement. Altern. Med., 2015, 12, 32-35.
[141]
Rahimifard, N.; Bagheri, E.; Asgarpanah, J.; Balajadeh, B.; Yazdi, H.; Bagheri, F. Study of the antibacterial activity of total extract and petroleum ether, chloroform, ethyl acetate and aqueous fractions of aerial parts of Heliotropium bacciferum against Staphylococcus aureus, Bacillus cereus, Pseudomonas aeruginosa, E. coli, Salmonella enteritidis. Biotechnol. Res. Asia., 2014, 11, 239-248.
[142]
Bick, Y.A.; Jackson, W.D. Effects of the pyrrolizidine alkaloid heliotrine on cell division and chromosome breakage in cultures of leucocytes from the marsupial Potorous tridactylus. Aust. J. Biol. Sci., 1968, 21(3), 469-481.
[143]
Culvenor, C.C.J.; Downing, D.T.; Edgar, J.A.; Jago, M.V. Pyrrolizidine alkaloids as alkylating and antimitotic agents. Ann. N. Y. Acad. Sci., 1969, 168, 837-847.
[144]
Mattocks, A.R. Dihydropyrrolizine derivatives from unsaturated pyrrolizidine alkaloids. J. Chem. Soc. Perkin Trans. I, 1969, 8, 1155-1162.
[145]
McLean, E.K. The toxic actions of pyrrolizidine (senecio) alkaloids. Pharmacol. Rev., 1970, 22(4), 429-483.
[146]
Bick, Y.E.; Culvenor, C.C. Effects of dehydroheliotridine, a metabolite of pyrrolizidine alkaloids on chromosome structure and cell division in cultures of animal cells. Cytobios, 1971, 3, 245-255.
[147]
Mroczek, T.; Glowniak, K. 2002.
[148]
Wondimu, T.; Asfaw, Z.; Kelbessa, E. Ethnobotanical study of medicinal plants around ‘Dheeraa’ town, Arsi Zone, Ethiopia. J. Ethnopharmacol., 2007, 112(1), 152-161.
[149]
Reina, M.; Mericli, A.H.; Cabrera, R.; González-Coloma, A. Pyrrolizidine alkaloids from Heliotropium bovei. Phytochemistry, 1995, 38, 355-358.
[150]
Savithramma, N.; Yugandhar, P.; Babu, H.R.; Siva Prasad, K. Validation of indigenous knowledge of yanadi tribe and local villagers of Veyilingalakona- a sacred grove of Andhra Pradesh, India. J. Pharm. Sci. Res., 2014, 6, 382-388.
[151]
Lakshmanan, A.J.; Shanmugasundaram, S. Heliscabine, a pyrrolizidine ester alkaloid from Heliotropium scabrum. Phytochemistry, 1995, 39, 473-475.
[152]
Lakshmanan, A.J.; Shanmugasundaram, S. Helibracti-necine, a pyrrolizidine alkaloid from Heliotropium bracteatum. Phytochemistry, 1994, 36, 245-248.
[153]
Ketterer, P.J.; Glover, P.E.; Smith, L.W. Blue heliotrope (Heliotropium amplexicaule) poisoning in cattle. Aust. Vet. J., 1987, 64(4), 115-117.
[154]
Quattrocchi, U. CRC World Dictionary of Medicinal and Poisonous Plants: Common Names, Scientific Names, Eponymes, Synonymes and Etymology; CRC Press: Boca Raton, FL, 2012.
[155]
Jain, S.C.; Purohit, M. Antitumor active pyrrolizidine alkaloids from Heliotropium marifolium Retz. Chem. Pharm. Bull., 1986, 34, 5154-5156.
[156]
Wunderlin, R.P.; Hansen, B.F.; Francke, A.R.; Essig, F.B. Atlas of Florida Plants. Institute of Systemic Botany; University of Florida: Florida, 2017.
[157]
Mandeel, Q.; Taha, A. Assessment of in vitro antifungal activities of various extracts of indigenous Bahraini medicinal plants. Pharm. Biol., 2005, 43(4), 340-348.
[158]
Catalfamo, J.L.; Martin, W.B., Jr; Birecka, H. Accumulation of alkaloids and their necines in Heliotropium curassavicum, H. spathulatum and H. indicum. Phytochemistry, 1982, 21, 2669-2675.
[159]
Mohanraj, S.; Subramanian, P.; Culvenor, C.C.J.; Edgar, J.A.; Frahn, J.L.; Smith, L.W.; Cockrum, P.A. Curassavine, an alkaloid from Heliotropium curassavicum Linn. with a C8 necic acid skeleton. J. Chem. Soc. Chem. Commun., 1978, 10, 423-424.
[160]
Davicino, J.G.; Pestchanker, M.J.; Giordano, O.S. Pyrrolizidine alkaloids from Heliotropium curassavicum. Phytochemistry, 1988, 27, 960-962.
[161]
Alwhibi, M.S. Characterization of seed storage protein patterns of Heliotropium digynum. Saudi J. Biol. Sci., 2016, 23.
[162]
Mandaville, J.P. Flora of Eastern Saudi Arabia; Routledge: London, New York, 2011.
[163]
Wiersema, J.H.; León, B. World Economic Plants; CRC Press: Boca Raton, 2011.
[164]
Hammouda, F.M.; Rizk, A.M.; Ismail, S.I.; Atteya, S.Z.; Ghaleb, H.A.; Madkour, M.K.; Pohland, A.E.; Wood, G. Poisonous plants contaminating edible ones and toxic substances in plant foods. Part 3. Pyrrolizidine alkaloids from Heliotropium digynum Forssk. (= H. luteum, Poir.). Pharmazie, 1984, 39(10), 703-705.
[165]
Roth, I.; Lindorf, H. South American Medicinal Plants: Botany; Remedial Properties and General Use, 2002.
[166]
Ara, I.; Bukhari, N.A.; Solaiman, D.; Bakir, M.A. Antimicrobial effect of local medicinal plant extracts in the Kindom of Saudi Arabia and search for their metabolites by gas chromatography – mass spectrometric (GC-MS) analysis. J. Med. Plants Res., 2012, 6, 5688-5694.
[167]
Shafiei, A.; Salimi, M.; Farsam, H. Pyrrolizidine alkaloids from Heliotropium dissitiflorum Boiss. Daru, 2002, 10, 168-170.
[168]
Marquina, G.; Laguna, A.; Vélez, H.; Ripperger, H. 9-Angeloylretronecine N-oxide from heliotropium bursiferum. Pharmazie, 1988, 43(1), 55-56.
[169]
Janbaz, K.H.; Javed, S.; Saqib, F.; Imran, I.; Zia-Ul-Haq, M.; De Feo, V. Validation of ethnopharmacological uses of Heliotropium strigosum Willd as spasmolytic, bronchodilator and vasorelaxant remedy. BMC Complement. Altern. Med., 2015, 15, 169.
[170]
Roeder, E.; Wiedenfeld, H. Pyrrolizidine alkaloids in medicinal plants of Mongolia, Nepal and Tibet. Pharmazie, 2009, 64(11), 699-716.
[171]
Watanabe, T.; Rajbhandari, K.R.; Malla, K.J.; Yahara, S. Handbook of Medicinal Plants of Nepal; Kobfai Publ. Projeck: Bangkok, 2005.
[172]
Marquina, G.; Laguna, A.; Franco, P.; Fernandez, L.; Perez, R.; Valiente, O. Antimicrobial activity of pyrrolizidine alkaloids from Heliotropium bursiferum Wr ex Grisebach. Pharmazie, 1989, 44(12), 870-871.
[173]
Hussain, S.; Jamil, M.; Ullah, F.; Khan, A.; Ullah, F.; Arfan, M. Antimicrobial and antioxidant activities of the plant Heliotropium strigosum. Afr. J. Biotechnol., 2010, 9, 7738-7743.
[174]
Mattocks, A.R. Strigosine, the major alkaloid of Heliotropium strigosum. J. Chem. Soc., 1964, 1964, 1974-1977.
[175]
Khan, H.; Khan, M.A.; Gul, F.; Hussain, S.; Ashraf, N. Anti-inflammatory activity of Heliotropium strigosum in animal models. Toxicol. Ind. Health, 2015, 31(12), 1281-1287.
[176]
Khan, H.; Khan, M.A.; Hussain, S.; Gaffar, R.; Ashraf, N. In vivo antinociceptive and anticonvulsant activity of extracts of Heliotropium strigosum. Toxicol. Ind. Health, 2016, 32(5), 860-865.
[177]
Shah, S.M.; Hussain, S.; Khan, A-U.; Shah, A.U.; Khan, H.; Ullah, F. Barkatullah, Cytotoxic and phytotoxic actions of Heliotropium strigosum. Toxicol. Ind. Health, 2015, 31(5), 429-432.
[178]
Bamber, C.J. Plants of the Punjab: A Descriptive Key to the Flora of the Punjab, North-West Frontier Province and Kashmir; Superintendent Government Printing Punjab Lahore, , 1916.
[179]
Schoental, R.; Coady, A. The hepatotoxicity of some Ethopian and East African plants including some used in traditional medicine. East Afr. Med. J., 1968, 45, 577-580.
[180]
Wiltjer, J.C.; Walker, C.E. Letter: Rectal prolapses in cattle associated with pyrrolizidine alkaloid poisoning. Aust. Vet. J., 1974, 50(12), 579-580.
[181]
Khurm, M.; Chaudhry, B.A.; Uzair, M.; Janbaz, K.H. Antimicrobial, cytotoxic, phytotoxic and antioxidant potential of Heliotropium strigosum Willd. Medicines (Basel), 2016, 3(3), 20.
[182]
Fawzy, M.A.; Hifney, A.F.; Issa, A.A-S.; Gareib, G. Phytochemical constituents and allelopathic effects of some medicinal plants extract on the soil algal diversity. J. Agric. Sci. Technol. A, 2013, 3, 1000-1009.
[183]
Men’shikov, G.P.; Gurevich, E.L. Alkaloids from Heliotropium supinum. I. Supinine and its structure. J. Gen. Chem. (USSR), 1949, 19, 1382-1386.
[184]
Crowley, H.C.; Culvenor, C.C.J. The alkaloids of Heliotropium supinum L., with observations on viridifloric acid. Aust. J. Chem., 1959, 12, 694-705.
[185]
Heath, A.; Heath, R. Field Guide to the Plants of Northern Botswana including the Okavango Delta., 2009.
[186]
Gurb-Fakim, A. Heliotropium ovalifolium Forssk. A Record from Protabase., 2006.
[187]
Duman, H.; Šağban, H. A New Record (Heliotropium ovalifolium Forssk.) from Southern Turkey. Turk. J. Bot., 2000, 24, 207-209.
[188]
Abu Damir, H.; Adam, S.E.; Tartour, G. The effects of Heliotropium ovalifolium on goats and sheep. Br. Vet. J., 1982, 138(6), 463-472.
[189]
Creeper, J.H.; Mitchell, A.A.; Jubb, T.F.; Colegate, S.M. Pyrrolizidine alkaloid poisoning of horses grazing a native heliotrope (Heliotropium ovalifolium). Aust. Vet. J., 1999, 77(6), 401-402.
[190]
Rizk, A.M.; Hammouda, F.M.; Hassan, N.M. Pyrrolizidine alkaloids from Heliotropium arbainense and H. ovalifolium. Qatar Univ. Sci. J., 1991, 11, 113-119.
[191]
Zalkow, L.H.; Bonetti, S.; Gelbaum, L.; Gordon, M.M.; Patil, B.B.; Shani, A.; Van Derveer, D. Pyrrolizidine alkaloids from Middle Eastern plants. J. Nat. Prod., 1979, 42, 603-612.
[192]
Mohanraj, S.; Kulanthaivel, P.; Subramanian, P.S.; Herz, W. Helifoline, a pyrrolizidine alkaloid from Heliotropium ovalifolium. Phytochemistry, 1981, 20, 1991-1995.
[193]
Rizk, A.M.; Hussiney, H.A. Extraction, fractionation and identification of pyrrolizidine alkaloids. In: Naturally Occurring Pyrrolizidine Alkaloids; Rizk, A.M., Ed.; CRC Press: Florida, 1990; pp. 91-100.
[194]
Kulkarni-Almeida, A.; Suthar, A.; Goswami, H.; Vishwakarma, R.; Chauhan, V.S.; Balakrishnan, A.; Sharma, S. Novel leads from Heliotropium ovalifolium, 4,7,8-trimethoxy-naphthalene-2-carboxylic acid and 6-hydroxy-5,7-dimethoxy-naphthalene-2-carbaldehyde show specific IL-6 inhibitory activity in THP-1 cells and primary human monocytes. Phytomedicine, 2008, 15(12), 1079-1086.
[195]
Datta, D.V.; Khuroo, M.S.; Mattocks, A.R.; Aikat, B.K.; Chhuttani, P.N. Herbal medicines and veno-occlusive disease in India. Postgrad. Med. J., 1978, 54(634), 511-515.
[196]
Culvenor, C.C.J.; Edgar, J.A.; Smith, L.W.; Kumana, C.R.; Lin, H.J. Heliotropium lasiocarpum Fisch and Mey identified as cause of veno-occlusive disease due to a herbal tea. Lancet, 1986, 1(8487), 978.
[197]
Woo, Y-T.; Lai, D.Y.; Arcos, J.C.; Argus, M.F. Chemical induction of Cancer: Structural Bases and Biological Mechanisms., 1988.
[198]
Rizk, A.; Kamel, A. Toxicity, carcinogenicity, pharmacology and other biological activities of pyrrolizidine alkaloids. In: Naturally Occurring Pyrrolizidine Alkaloids; Rizk, A.M., Ed.; CRC Press: Florida, USA, 1991; pp. 211-226.
[199]
Chernenko, T.V.; Gusakova, S.D.; Glushenkova, A.I. Lipids and alkaloids from Heliotropium lasiocarpum. Chem. Nat. Compd., 2011, 47, 683-685.
[200]
Akhani, H. Heliotropium disciforme (Boraginaceae) a new species from North-East of Iran. Linzer Biologische Beiträge, 1991, 23, 569-573.
[201]
Akhani, H.; Förther, H. The genus Heliotropium L. (Boraginaceae) in Flora of Iranica Area. Sendtnera, 1994, 2, 187-276.
[202]
Hartmann, T.; Witte, L. Chemistry, biology and chemoecology of the pyrrolizidine alkaloids. In: Alkaloids: Chemical and Biological Perspectives; Pelletier, S.W., Ed.; Elsevier Science Ltd: Kidlington, UK, 1995; pp. 155-233.
[203]
Farsam, H.; Yassa, N.; Shafiee, A.; Amanlou, M.; Biglar, M.; Pourlotfali, T. Pyrrolizidine alkaloids from Heliotropium disciforme. Pharm. Pharmacol. Lett., 1998, 8, 79-80.
[204]
Kılıç, Ö. An ethnobotanical survey from Bingol (Turkey). RA J. Appl. Res., 2016, 2, 685-691.
[205]
Eröksüz, H.; Eröksüz, Y.; Ozer, H.; Ceribasi, A.O.; Tosun, F.; Tamer, U.; Kizilay, C.A. Toxicity of dietary Heliotropium circinatum to rats. Vet. Hum. Toxicol., 2003, 45(4), 198-201.
[206]
Yassa, N.; Farsam, H.; Shafiee, A.; Rustaiyan, A. Pyrrolizidine alkaloids from Heliotropium esfandiarii. Planta Med., 1996, 62(6), 583-584.
[207]
El-Gazzar, A.; El-Ghamery, A.; El-Saied, A.B.; Khattab, A.H.; El-Kady, A.A. Computer generated keys to the flora of Egypt. 6. The Boraginaceae. Ann. Agric. Sci., 2015, 60, 67-85.
[208]
Eröksüz, Y.; Çeribaşi, A.O.; Çevik, A.; Eröksüz, H.; Tosun, F.; Tamer, U. Toxicity of Heliotropium dolosum, Heliotropium circinatum, and Senecio vernalis in parental quail and their progeny, with residue evaluation of eggs. Turk. J. Vet. Anim. Sci., 2008, 32, 475-482.
[209]
Eröksüz, Y.; Çeribaşi, A.O.; Çevik, A.; Eröksüz, H.; Tosun, F.; Tamer, U. Toxicity of Heliotropium dolosum, Heliotropium circinatum, and Senecio vernalis in parental quail and their progeny, with residue evaluation of eggs. Turk. J. Vet. Anim. Sci., 2008, 32, 475-482.
[210]
Sebastian, D.P.; Hariharan, M. Micropropagation of Heliotropium keralense-a globally endangered and endemic medicinal plant through indirect organogenesis from roots. Int. J. Curr. Microbiol. Appl. Sci., 2013, 2, 56-62.
[211]
Chong, K.Y.; Tan, H.T.W.; Corlett, T. A Checklist of the Total Vascular Plant Flora of Singapore: Native, Naturalized and Cultivated Species; Raffles Museum of Biodiversity Research: National University of Singapore, Singapore;. , 2009. pp. 273.
[212]
Ravi, S.; Lakshmanan, A.J.; Herz, W. Iso-lycopsamine, a pyrrolizidine alkaloid from Heliotropium keralense. Phytochemistry, 1990, 29, 361-364.


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