Planta Med 2019; 85(11/12): 869-910
DOI: 10.1055/a-0953-6165
Biological and Pharmacological Activity
Reviews
Georg Thieme Verlag KG Stuttgart · New York

A Review of the Phytochemistry, Traditional Uses, and Biological Activities of the Genus Ballota and Otostegia [ 1 ]

Sergio Rosselli
1   Department of Agricultural, Food and Forest Sciences (SAAF), University of Palermo, Viale delle Scienze, Parco dʼOrleans II, IT-90128 Palermo, Italy
,
Gianfranco Fontana
2   Department of Biological, Chemical and Pharmaceutical Sciences and Technologies (STEBICEF), University of Palermo, Viale delle Scienze, Parco dʼOrleans II, IT-90128 Palermo, Italy
,
Maurizio Bruno
2   Department of Biological, Chemical and Pharmaceutical Sciences and Technologies (STEBICEF), University of Palermo, Viale delle Scienze, Parco dʼOrleans II, IT-90128 Palermo, Italy
› Author Affiliations
Further Information

Publication History

received 24 January 2019
revised 05 June 2019

accepted 07 June 2019

Publication Date:
19 June 2019 (online)

Abstract

The 2 genera Ballota and Otostegia, belonging to the Lamiaceae family, are closely related taxonomically and found mainly in the Mediterranean area, Middle East, and North Africa. Since ancient times, they have been largely employed in traditional medicine for their biological properties such as antimicrobial, anti-inflammatory, antispasmodic, insecticidal, anti-malaria, etc. Phytochemical investigations of Ballota and Otostegia species have revealed that diterpenoids are the main constituents of the genera. A large number of flavonoids and other metabolites were also identified. This review, covering literature from 1911 up to 2018, includes traditional uses, chemical profiles (both of volatile and nonvolatile metabolites), and biological properties of all the taxa of these 2 genera studied to date.

1 Dedicated to Professor Dr. Cosimo Pizza in recognition of his important contributions to natural product research on the occasion of his 70th birthday in 2019.


 
  • References

  • 1 Erdtman G. Pollen morphology and plant taxonomy. IV. Labiatae, Verbenaceae and Avicennaceae. Svensk Bot Tidskr 1945; 39: 279-285
  • 2 Cantino PD, Sanders RW. Subfamilial classification of Labiatae. Syst Bot 1986; 11: 163-185
  • 3 Patzäk A. Revision der Gattung Ballota Section Âcanthoprasium und Section Beringeria. Ann Naturhist Mus Wien 1958; 62: 57-86
  • 4 Patzäk A. Revision der Gattung Ballota Section Âcanthoprasium und Section Beringeria. Ann Naturhist Mus Wien 1959; 63: 33-81
  • 5 Patzäk A. Revision der Gattung Ballota Section Âcanthoprasium und Section Beringeria. Ann Naturhist Mus Wien 1961; 64: 42-56
  • 6 The Plant List. Available at: http://www.theplantlist.org Accessed September 5, 2018
  • 7 Bendiksby M, Thorbek L, Scheen AC, Lindqvist C, Ryding O. An updated phylogeny and classification of Lamiaceae subfamily Lamioideae. Taxon 2011; 60: 471-484
  • 8 Harley RM, Atkins S, Budantsev AL, Cantino PD, Conn BJ, Grayer R, Harley MM, De Kok R, Krestovskaja T, Morales R, Paton AJ, Ryding O, Upson T. Labiatae. In: Kadereit JW. ed. The Families and Genera of vascular Plants. Vol. 7: Lamiales. Berlin, Heidelberg: Springer; 2004: 167-275
  • 9 Hedge IC. A global Survey of the Biogeography of the Labiatae. In: Harley RM, Reynolds T. eds. Advances in labiate Science. Kew: The Royal Botanic Gardens; 1992: 7-17
  • 10 Scheen AC, Albert VA. Nomenclatural and taxonomic changes within the Leucas clade (Lamioideae; Lamiaceae). Syst Geogr Pl 2007; 77: 229-238
  • 11 Tuzlaci E, Sadikoğlu E. Turkish folk medicinal plants, part VI: Koçarli (Aydin). J Fac Pharm Istanbul 2007; 39: 25-37
  • 12 Dumlu MU, Bulut GE. Some biological activity investigations on Ballota acetabulosa . J Fac Pharm Istanbul 2007; 39: 53-56
  • 13 Nortje JM, Van Wyk BE. Medicinal plants of the Kamiesberg, Namaqualand, South Africa. J Ethnopharmacol 2015; 171: 205-222
  • 14 Scott G, Springfield EP, Coldrey N. A pharmacognostical study of 26 South African plant species used as traditional medicines. Pharm Biol 2004; 42: 186-213
  • 15 Cock IE, van Vuuren SF. Anti-proteus activity of some South African medicinal plants: their potential for the prevention of rheumatoid arthritis. Inflammopharmacology 2014; 22: 23-36
  • 16 Akhtar K, Khan SB, Malik A. Phytochemistry and pharmacological aspects of Leucas urticifolia (Vahl) Benth. J Pharm Res Health Care 2010; 2: 197-203
  • 17 Sadeghi Z, Kuhestani K, Abdollahi V, Mahmood A. Ethnopharmacological studies of indigenous medicinal plants of Saravan region, Baluchistan, Iran. J Ethnopharmacol 2014; 153: 111-118
  • 18 Bano A, Ahmad M, Zafar M, Sultana S, Rashid S, Khan MA. Ethnomedicinal knowledge of the most commonly used plants from Deosai Plateau, Western Himalayas, Gilgit Baltistan, Pakistan. J Ethnopharmacol 2014; 155: 1046-1052
  • 19 Natarajan B, Paulsen BS, Korneliussen V. An ethnopharmacological study from Kulu district, Himachal Pradesh, India: traditional knowledge compared with modern biological science. Pharm Biol 2000; 38: 129-138
  • 20 Rawat R, Vashistha DP. Roylea cinerea (D. Don) Baillon: a traditional curative of diabetes, its cultivation prospects in Srinagar Valley of Uttarakhand. Int J Adv Pharm Biol Chem 2013; 2: 372-375
  • 21 Dangwal LR. Ethnomedicinal plants used for the treatment of diabetes among the villagers of Narendra Nagar block, district Tehri Garhwal, Uttarakhand, India. World J Pharm Pharm Sci 2015; 4: 1178-1184
  • 22 Bisht S, Pangti J, Pundir S, Das A, Devi J. Total phenolic and total flavonoid compounds in the leaves of Roylea cinerea using hydroalcoholic extract. World J Pharm Pharm Sci 2016; 7: 1753-1759
  • 23 Hammiche V, Maiza K. Traditional medicine in Central Sahara: pharmacopoeia of Tassili Nʼajjer. J Ethnopharmacol 2006; 105: 358-367
  • 24 Dendougui H, Seghir S, Belloum Z, Benayache F, Leon F, Brouard I, Bermejo J, Benayache S. A new labdane diterpene and other constituents from Marrubium deserti Noe ex Coss. Rec Nat Prod 2011; 5: 300-304
  • 25 Edziri H, Mastouri M, Aouni M, Verschaeve L. Polyphenols content, antioxidant and antiviral activities of leaf extracts of Marrubium deserti growing in Tunisia. S Afr J Bot 2012; 80: 104-109
  • 26 Teixidor-Toneu I, Martin GJ, Ouhammou A, Puri RK, Hawkins JA. An ethnomedicinal survey of a Tashelhit-speaking community in the High Atlas, Morocco. J Ethnopharmacol 2016; 188: 96-110
  • 27 Kechar K, Hellal B, Ayad N, Benahmed-Djilali A. Ethnobotanical investigation of Ballota hirsuta (Benth) at Sidi Bel Abbes (Algeria). Phytotherapie 2016; 14: 343-348
  • 28 Zheng YF, Yin W, Lin LL, Du SS, Shan T, Wang Y. Advances in studies on Panzeria alaschanica . Zhong Cao Yao 2007; 38: 1434-1436
  • 29 Olennikov DN, Tankhaeva LM. Chemical study of Panzerina lanata . Chem Nat Compd 2011; 47: 802-804
  • 30 Rexhepi B, Mustafa B, Hajdari A, Rushidi-Rexhepi J, Quave CL, Pieroni A. Traditional medicinal plant knowledge among Albanians, Macedonians and Gorani in the Sharr Mountains (Republic of Macedonia). Genet Resour Crop Evol 2014; 60: 2055-2080
  • 31 Ciocarlan N. Family Lamiaceae: main important spontaneous medicinal and aromatic species in the Republic of Moldova. J Bot 2016; 8: 86-91
  • 32 Šarić-Kundalić B, Dobeš C, Klatte-Asselmeyer V, Saukel J. Ethnobotanical survey of traditionally used plants in human therapy of east, north and north-east Bosnia and Herzegovina. J Ethnopharmacol 2011; 133: 1051-1076
  • 33 Pieroni A. Medicinal plants and food medicines in the folk traditions of the upper Lucca Province, Italy. J Ethnopharmacol 2000; 70: 235-273
  • 34 Mulas M. Traditional uses of Labiatae in the Mediterranean area. Acta Hortic 2006; 723: 25-32
  • 35 Pieroni A, Quave C, Nebel S, Heinrich M. Ethnopharmacy of the ethnic Albanians (Arbëreshë) of northern Basilicata, Italy. Fitoterapia 2001; 73: 217-241
  • 36 Pieroni A, Quave CL, Santoro RF. Folk pharmaceutical knowledge in the territory of the Dolomiti Lucane, inland southern Italy. J Ethnopharmacol 2004; 95: 373-384
  • 37 Redzić SS. The ecological aspect of ethnobotany and ethnopharmacology of population in Bosnia and Herzegovina. Coll Antropol 2007; 31: 869-890
  • 38 Nićiforović N, Mihailović V, Mašković P, Solujić S, Stojković A, Muratspahić DP. Antioxidant activity of selected plant species; potential new sources of natural antioxidants. Food Chem Toxicol 2010; 48: 3125-3130
  • 39 Gonzalez JA, Garcia-Barriuso M, Gordaliza M, Amich F. Traditional plant-based remedies to control insect vectors of disease in the Arribes del Duero (Western Spain): an ethnobotanical study. J Ethnopharmacol 2011; 138: 595-601
  • 40 Yeflilada E, Honda G, Sezik E, Tabata M, Goto T, Ikeshiro Y. Traditional medicine in Turkey IV. Folk medicine in the Mediterranean subdivision. J Ethnopharmacol 1993; 39: 31-38
  • 41 Yeflilada E, Honda G, Sezik E, Tabata M, Fujita T, Tanaka T, Takeda Y, Takaishi Y. Traditional medicine in Turkey V. Folk medicine in the inner Taurus Mountains. J Ethnopharmacol 1995; 46: 133-152
  • 42 Tuzlaci E, Aymaz PE. Turkish folk medicinal plants, part IV: Gönen (Balikesir). Fitoterapia 2001; 72: 323-343
  • 43 Kültür S. Medicinal plants used in Kirklareli Province (Turkey). J Ethnopharmacol 2007; 111: 341-364
  • 44 Mothana RAA, Kriegisch S, Harms M, Wende K, Lindequist U. Assessment of selected Yemeni medicinal plants for their in vitro antimicrobial, anticancer, and antioxidant activities. Pharm Biol 2011; 49: 200-210
  • 45 Mothana RA, Al-Musayeib NM, Al-Ajmi MF, Cos P, Maes L. Evaluation of the in vitro antiplasmodial, antileishmanial, and antitrypanosomal activity of medicinal plants used in Saudi and Yemeni traditional medicine. Evid Based Complement Alternat Med 2014; 905639: 1-7
  • 46 Meragiaw M, Asfaw Z, Argaw M. The status of ethnobotanical knowledge of medicinal plants and the impacts of resettlement in Delanta, Northwestern Wello, Northern Ethiopia. Evid Based Complement Alternat Med 2016; 2016: 5060247
  • 47 Kidane D, Tomass Z, Dejene T. Community knowledge of traditional mosquito repellent plants in Kolla Temben District, Tigray, Northern Ethiopia. Sci Res Essays 2013; 8: 1139-1144
  • 48 Seyoum G, Zerihun G. An ethnobotanical study of medicinal plants in Debre Libanos Wereda, Central Ethiopia. Afr J Plant Sci 2014; 8: 366-379
  • 49 Rahman MA, Mossa JS, Al-Said MS, Al-Yahya MA. Medicinal plant diversity in the flora of Saudi Arabia 1: a report on seven plant families. Fitoterapia 2004; 75: 149-161
  • 50 Waka M, Hopkins RJ, Curtis C. Ethnobotanical survey and testing of plants traditionally used against hematophagous insects in Eritrea. J Ethnopharmacol 2004; 95: 95-101
  • 51 Teklehaymanot T, Giday M, Medhin G, Mekonnen Y. Knowledge and use of medicinal plants by people around Debre Libanos monastery in Ethiopia. J Ethnopharmacol 2007; 111: 271-283
  • 52 Karunamoorthi K, Husen E. Knowledge and self-reported practice of the local inhabitants on traditional insect repellent plants in Western Hararghe zone, Ethiopia. J Ethnopharmacol 2012; 141: 212-219
  • 53 Giday G, Teklehaymanot T, Animut A, Mekonnen Y. Medicinal plants of the Shinasha, Agew-awi and Amhara peoples in northwest Ethiopia. J Ethnopharmacol 2007; 110: 516-525
  • 54 Mekuria AB, Belachew SA, Tegegn HG, Ali DS, Netere AK, Lemlemu E, Erku DA. Prevalence and correlates of herbal medicine use among type 2 diabetic patients in Teaching Hospital in Ethiopia: a cross-sectional study. BMC Complement Altern Med 2018; 18: 85
  • 55 Tesfaye H, Hishe M, Badasa S. Phytochemical and ethno botanical study of medicinal plants used to treat ectoparasites in ruminant animals in eastern Tigray, northern Ethiopia. Int J Pharmacogn (Panchkula, India) 2015; 2: 466-472
  • 56 Tadesse S, Messele B, Seyoum A, Mazumder A, Bucar F, Asres K. Essential oil of Otostegia integrifolia Benth: composition, antimicrobial and antioxidant activities. Ethiop Pharm J 2011; 29: 79-86
  • 57 Chopra RN, Nayar SL, Chopra IC. Glossary of Indian medicinal Plant. India: Indian Council of Scientific & Industrial Research; 1956: 183
  • 58 Adnan M, Hussain J, Shah MT, Shinwari ZK, Ullah F, Bahader A, Khan N, Khan AL, Watanabe T. Proximate and nutrient composition of medicinal plants of humid and sub-humid regions in north-west Pakistan. J Med Plants Res 2010; 4: 339-345
  • 59 Abbasi AM, Khan MA, Ahmad M, Zafar M, Jahan S, Sultana S. Ethnopharmacological application of medicinal plants to cure skin diseases and in folk cosmetics among the tribal communities of North-West Frontier Province, Pakistan. J Ethnopharmacol 2010; 128: 322-335
  • 60 Haq F, Ahmad H, Alam M. Traditional uses of medicinal plants of Nandiar Khuwarr catchment (District Battagram), Pakistan. J Med Plants Res 2011; 5: 39-48
  • 61 Rehman K, Mashwani ZUR, Khan MA, Ullah Z, Chaudhary HJ. An ethno botanical perspective of traditional medicinal plants from the Khattak tribe of Chonthra Karak, Pakistan. J Ethnopharmacol 2015; 165: 251-259
  • 62 Murad W, Ahmad A, Gilani SA, Khan MA. Indigenous knowledge and folk use of medicinal plants by the tribal communities of Hazar Nao forest, Malakand district, North Pakistan. J Med Plants Res 2011; 5: 1072-1086
  • 63 Iqbal H, Sher Z, Khan ZU. Medicinal plants from salt range Pind Dadan Khan, district Jhelum, Punjab, Pakistan. J Med Plants Res 2011; 5: 2157-2168
  • 64 Adnan M, Bibi R, Azizullah A, Andaleeb R, Mussarat S, Tariq A, Ullah R, Elsalam NM, Khan AL, Begum S. Ethnomedicinal plants used against common digestive problems. Afr J Tradit Complement Altern Med 2015; 12: 99-117
  • 65 Rashid S, Ahmad M, Zafar M, Sultana S, Ayub M, Khan MA, Yaseen G. Ethnobotanical survey of medicinally important shrubs and trees of Himalayan region of Azad Jammu and Kashmir, Pakistan. J Ethnopharmacol 2015; 166: 340-351
  • 66 Ahmad L, Semotiuk A, Zafar M, Ahmad M, Sultana S, Liu QR, Zada MP, Abidin SZU, Yaseen G. Ethnopharmacological documentation of medicinal plants used for hypertension among the local communities of DIR Lower, Pakistan. J Ethnopharmacol 2015; 175: 138-146
  • 67 Hussain S, Murtaza G, Mehmood A, Qureshi RA. Conservation of indigenous knowledge of medicinal plants of Western Himalayan region Rawalakot, Azad Kashmir, Pakistan. Pak J Pharm Sci 2017; 30: 773-782
  • 68 Bibi R, Tariq A, Mussarat S, Khan SN, Rahman H, Allah EFA, Ullah R, Adnan M. Ethnomedicinal, phytochemical and antibacterial activities of medicinal flora of Pakistan used against Pseudomonas aeruginosa – a review. Pak J Pharm Sci 2017; 30: 2285-2300
  • 69 Habiba U, Ahmad M, Shinwari S, Sultana S, Shinwari ZK, Zafar M. Antibacterial and antifungal potential of Himalayan medicinal plants for treating wound infections. Pak J Bot 2016; 48: 371-375
  • 70 Savona G, Piozzi F, Hanson JR, Siverns M. Structures of three new diterpenoids from Ballota species. J Chem Soc Perkin I 1977; 322-324
  • 71 Rustaiyan A, Mosslemin-Kupaii MH, Zdero C. Furolabdanes and related compounds from Ballota aucheri . Phytochemistry 1992; 31: 344-346
  • 72 Yilmaz BS, Çitoğlu GS. High performance liquid chromatographic analysis of some diterpenoids of the Ballota species. FABAD J Pharm Sci 2003; 28: 13-17
  • 73 Çitoğlu GS, Yilmaz BS, Tarikahya B, Tipirdamaz R. Chemotaxonomy of Ballota species. Chem Nat Compd 2005; 41: 299-302
  • 74 Rustaiyan A, Mosslemin-Kupaii MH, Papastergiou F, Jakupovic J. Persianone, a dimeric diterpene from Ballota aucheri . Phytochemistry 1995; 40: 875-879
  • 75 Yilmaz BS, Çitoğlu GS. Chemical constituents of Ballota L. species. Ankara Universitesi Eczacilik Fakultesi Dergisi 2003; 32: 37-53
  • 76 Çitoğlu GS, Sever B, Antus S, Baitz-Gács E, Altanlar N. Antifungal diterpenoids and flavonoids from Ballota inaequidens . Pharm Biol 2004; 42: 659-663
  • 77 Savona G, Piozzi F, Hanson JR. 13-Hidroxyballonigrinolide, a new diterpenoid from Ballota lanata . Phytochemistry 1978; 17: 2132-2133
  • 78 Savona G, Piozzi F, Hanson JR, Siverns M. New diterpenoids from species of genus Ballota . Chim Ind 1976; 58: 378
  • 79 Savona G, Bruno M, Piozzi F, Barbagallo C. Diterpenes from Ballota species. Phytochemistry 1982; 21: 2132-2133
  • 80 Çitoğlu G, Tanker M, Sever B, Englert J, Anton R, Altanlar N. Antibacterial activities of diterpenoids isolated from Ballota saxatilis subsp. saxatilis . Planta Med 1998; 40: 484-485
  • 81 Hussein AA, Jimeno ML, Rodríguez B. Structural and spectral assignment of a new diterpenoid isolated from Ballota undulata and complete H and C NMR data assignment for three other structurally related compounds. Mag Res Chem 2007; 45: 899-901
  • 82 Al-Musayeib NM, Abbas FA, Ahmad MS, Mossa JS, El-Feraly FS. Labdane diterpenes from Otostegia fruticosa . Phytochemistry 2000; 54: 771-775
  • 83 Farooq U, Khan A, Khan AF, Khan SS, Sarwar R, Ahmad VU, Waseem A. Two new ballonigrin-type diterpenoids from the roots of Ballota limbata . Nat Prod Commun 2012; 7: 149-150
  • 84 Savona G, Piozzi F, Hanson JR, Siverns M. The structure of ballotenol, a new diterpenoid from Ballota nigra . J Chem Soc Perkin I 1977; 497-499
  • 85 Savona G, Piozzi F, Hanson JR, Siverns M. Structure of ballotinone, a diterpenoid from Ballota nigra . J Chem Soc Perkin I 1976; 1607-1609
  • 86 Prakash O, Bhakuni DS, Kapil RS, Rao GSRS, Ravindranath B. Diterpenoids of Roylea calycina (Roxb.) Briq. J Chem Soc Perkin I 1979; 1305-1308
  • 87 Sharma R, Chebolu R, Ravikumar PC. Isolation and structural elucidation of two new labdane diterpenoids from the aerial part of Roylea cinerea . Phytochemistry Lett 2015; 13: 187-193
  • 88 Sharma R, Mohammadi-Ostad-Kalayeh S, Stahl F, Zeilinger C, Dräger G, Kirschning A, Ravikumar PC. Two new labdane diterpenoids and one new – lactam from the aerial parts of Roylea cinerea . Phytochemistry Lett 2017; 19: 101-107
  • 89 Zaabat N, Hay AE, Michalet S, Darbour N, Bayet C, Skandrani I, Chekir-Ghedira L, Akkal S, Dijoux-Franca MG. Antioxidant and antigenotoxic properties of compounds isolated from Marrubium deserti de Noé. Food Chem Toxicol 2011; 49: 3328-3335
  • 90 Zaabat N, Darbour N, Bayet C, Michalet S, Doléans-Jordheim A, Chekir-Ghedira L, Akkal S, Dijoux-Franca MG. Preliminary study of Marrubium deserti de Noé, an endemic Algerian Lamiaceae. Phytotherapie 2010; 8: 353-358
  • 91 Davies-Coleman MT, Rivett DEA. Transformation of hispanolone from Ballota africana into 15, 16-epoxy-9-hydroxylabda-13(16), 14-diene. S Afr J Chem 1990; 43: 117-119
  • 92 Savona G, Piozzi F, Rodriguez B. Hispanolone, a new furanoditerpene. Heterocycles 1978; 9: 257-261
  • 93 Seidel V, Bailleul F, Tillequin F. Isolation from Ballota nigra L. of 13-hydroxyballonigrinolide, a diterpene useful for the standardization of the drug. J Pharm Belg 1996; 51: 72-73
  • 94 Seidel V, Bailleul F, Tillequin F. Diterpene et esters heterosidiques phenylpropanoiques de Ballota nigra . Ann Pharm Fr 1998; 56: 31-35
  • 95 Savona G, Piozzi F, Hanson JR, Siverns M. 18-Hidroxyballonigrin, a new diterpenoid from Ballota acetabulosa . J Chem Soc Perkin I 1978; 1271-1272
  • 96 Bruno M, Bondí ML, Piozzi F, Arnold NA, Simmonds MSJ. Occurrence of 18-hydroxyballonigrine in Ballota saxatilis ssp. saxatilis from Lebanon. Biochem System Ecol 2001; 29: 429-431
  • 97 Rustaiyan A, Mosslemin-Kupaii MH, Habibi Z. Two new diterpenes from Ballota aucheri . Iran J Chem Chem Eng 1991; 10: 72-77
  • 98 Ali MS, Amina M, Al-Lohedan HA, Al Musayeib NM. Human serum albumin binding to the biologically active labdane diterpene “leoheterin”: spectroscopic and in silico analysis. J Photochem Photobiol B 2018; 182: 9-17
  • 99 Balansard J. The lactone of some Labiatae. C R Seances Soc Biol 1934; 117: 1014-1015
  • 100 Tesso H, König WA. Terpenes from Otostegia integrifolia . Phytochemistry 2004; 65: 2057-2062
  • 101 Endale A, Bisrat D, Animut A, Bucar F, Asres K. In vivo antimalarial activity of a labdane diterpenoid from the leaves of Otostegia integrifolia Benth. Phytother Res 2013; 27: 1805-1809
  • 102 Bruno M, Savona G, Pascual C, Rodríguez B. Preleosibirin, a prefuranic labdane diterpene from Ballota nigra subsp. foetida . Phytochemistry 1986; 25: 538-539
  • 103 Savona G, Piozzi F, Marino M. Rupestralic acid, a new lactone. Heterocycles 1977; 7: 161-164
  • 104 Rodriguez B, Savona G, Piozzi F. Two new unusual diterpenoids from Ballota hispanica . J Org Chem 1979; 44: 2219-2221
  • 105 López de Lerma J, García-Blanco S, Rodríguez JG. New compounds from Ballota hispanica. X-ray crystal and molecular structure of hispanonic acid methyl ester. Tetrahedron Lett 1980; 21: 1273-1274
  • 106 Riaz M, Krohna K, Malik A, Flörke U. Limbetazulone: a new ʼdecahydro-8-oxanaphtho[2, 1-f]-azulen-7-oneʼ diterpenoid from Ballota limbata, and occurence of two conformational isomers in the crystal. Chem Biodivers 2004; 1: 458-462
  • 107 Ahmad VU, Farooq U, Abbaskhan A, Hussain J, Abbasi MA, Nawaz SA, Choudhary MI. Four new diterpenoids from Ballota limbata . Helv Chim Acta 2004; 87: 682-689
  • 108 Ayatollahi SA, Kobarfard F, Asgarpanah J, Rahmati Roodsari M, Fanai Gh. Iqbal Choudhary M. Diterpenoids of Otostegia persica (Burm.) Boiss. DARU J Pharm Sci 2009; 17: 290-293
  • 109 Farooq U, Khan A, Ahmad VU, Khan SS, Kousar F, Arshad S. Two new rare-class tetracyclic diterpenoids from Otostegia limbata . Chem Pharm Bull 2007; 55: 471-473
  • 110 Ahmad VU, Farooq U, Hussain J, Ullah F, Nawaz SA, Choudhary MI. Two new diterpenoids from Ballota limbata . Chem Pharm Bull 2004; 52: 441-443
  • 111 Farooq U, Khan A, Ahmad VU, Azhar-Ul-Haq. Khan SS, Farooq R, Pervez A, Shah MM. Complete 1H and 13C NMR assignments of two new trans-clerodane diterpenoids from Otostegia limbata . Magn Reson Chem 2007; 45: 766-769
  • 112 Ahmad VU, Khan A, Farooq U, Kousar F, Khan SS, Nawaz SA, Abbasi MA, Choudhary MI. Three new cholinesterase-inhibiting cis-clerodane diterpenoids from Otostegia limbata . Chem Pharm Bull 2005; 53: 378-381
  • 113 Ahmad VU, Khan A, Farooq U, Kousar F, Khan SS, Hussain J. Two new trans-clerodane diterpenoids from Otostegia limbata . J Asian Nat Prod Res 2007; 9: 91-95
  • 114 Farooq U, Khan A, Ahmad VU, Kousar F, Iqbal S. Limbatolide F and G: two new trans-clerodane diterpenoids from Otostegia limbata . Polish J Chem 2005; 79: 1757-1762
  • 115 Tóth E, Tóth G, Máthé I, Blunden G. Martynoside, forsythoside B, ladanein and 7α-acetoxyroyleanone from Ballota nigra L. Biochem System Ecol 2007; 35: 894-897
  • 116 Kumar S, Dobhal MP, Joshi BC, Baror FSK. Chemical investigation and pharmacological screening of Roylea elegans Wall. Part Wall. Part II. Herba Polonica 1981; 27: 99-102
  • 117 Shabnam Habib R, Jamshaid M, Tahir MN, Khan TJ, Khan IU. (4R,5R,6S,7R,8S,9R,10S,13S)-7,8β-Epoxy-momilactone-A. Acta Crystallogr E 2008; 64: o892
  • 118 Gray CA, Rivett DEA, Davies-Coleman MT. The absolute stereochemistry of a diterpene from Ballota aucheri . Phytochemistry 2003; 63: 409-413
  • 119 Harrison LJ, Asakawa Y. Methyl verticoate, a novel diterpenoid with an unusual carbon skeleton from the conifer Sciadopitys verticillata . J Chem Res 1988; 10: 340-341
  • 120 Wu SJ, Chan HH, Hwang TL, Qian K, Morris-Natschke S, Lee KH, Wu TS. Salviatalin A and salvitrijudin A, two diterpenes with novel skeletons from roots of Salvia digitaloides and anti-inflammatory evaluation. Tetrahedron Lett 2010; 51: 4287-4290
  • 121 Wu SJ, Huang CH, Chan YY, Liao YR, Hwang TL, Wu TS. Two diterpenoids and a cyclopenta[c]pyridine derivative from roots of Salvia digitaloids . Int J Mol Sci 2014; 15: 11566-11577
  • 122 Wang LX, Fang YD, Zhang RH, Ren FC, Zhang XJ, Wang F, Xiao WL. Hispanane-type diterpenoid and secoiridoid glucosides from Viburnum cylindricum . Chem Biodivers 2018; 15: e1700418
  • 123 Herz W, Prasad JS, Mohanraj S. Cationic cyclizations and rearrangements as models for strobane and hispanane biogenesis. J Org Chem 1983; 48: 81-90
  • 124 Karioti A, Heilmann J, Skaltsa H. Labdane diterpenes from Marrubium velutinum and Marrubium cylleneum . Phytochemistry 2005; 66: 1060-1066
  • 125 Hersel U, Steck M, Seifert K. A new route to 2,7- and 7-functionalized labdanes. Eur J Org Chem 2000; 1609-1615
  • 126 Tasdemir D, Wright AD, Sticher O. New furanoid and seco-labdanoid diterpenes from Leonurus persicus . J Nat Prod 1996; 59: 131-134
  • 127 Hussein AA, Meyer MJJ, Rodriguez B. Complete 1H and 13C NMR assignments of three labdane diterpenoids isolated from Leonotis ocymifolia and six other related compounds. Magn Reson Chem 2003; 41: 147-151
  • 128 El Bardai S, Morel N, Wibo M, Fabre N, Llabras G, Lyoussi B, Quetin-Leclerrcq J. The vasorelaxxant activity of marrubenol and marrubin from Marrubium vulgare . Planta Med 2003; 69: 75-77
  • 129 Rigano D, Aviello G, Bruno M, Formisano C, Rosselli S, Capasso R, Senatore F, Izzo AA, Borrelli F. Antispasmodic effects and structure-activity relationship of labdane diterpenoids from Marrubium globosum ssp. libanoticum . J Nat Prod 2009; 72: 1477-1481
  • 130 Tesso H. Isolation and Structure Elucidation of natural Products from Plants [Dissertation]. Hamburg: University of Hamburg, Institute of Organic Chemistry; 2005
  • 131 Rodriguez B, Savona G. Complete assignments of 1H and 13C NMR spectra of four hispanane diterpenoids. Magn Reson Chem 2000; 38: 802-804
  • 132 Saeidnia S, Ghamarinia M, Gohari AR, Shaker A. Terpenes from the root of Salvia hypoleuca Benth. DARU J Pharm Sci 2012; 20: 66
  • 133 Wellsow J, Grayer JR, Veitch NC, Kokubun T, Lelli R, Kite GC, Simmonds MSJ. Insect-antifeedant and antibacterial activity of diterpenoids from species of Plectranthus . Phytochemistry 2006; 67: 1818-1825
  • 134 Meriçli AH, Meriçli F, Tuzlacı E. Flavonoids of Ballota acetabulosa . Acta Pharmaceutica Turcica 1988; 30: 143-144
  • 135 Askun T, Tekwu EM, Satil F, Modanlioglu S, Aydeniz H. Preliminary antimycobacterial study on selected Turkish plants (Lamiaceae) against Mycobacterium tuberculosis and search for some phenolic constituents. BMC Complement Altern Med 2014; 13: 365
  • 136 Ferreres F, Tomas-Barberan FA, Tomas-Lorente F. Flavonoid compounds from Ballota hirsuta . J Nat Prod 1986; 49: 554-555
  • 137 Tomás-Barberan FA, Gil MI, Ferreres F, Tomás-Lorente F. Flavonoid p-coumaroylglucosides and 8-hydroxyflavone allosylglucosides in some Labiatae. Phytochemistry 1992; 31: 3097-3102
  • 138 Jiang S, Bai XR, Zou DZ, Wang P, Zhang L, Long P, Zhang CH, He YL, Li ZH, Li MH. Chemical constituents from Panzeria alaschanica Kupr. (Labiatae). Biochem System Ecol 2015; 61: 268-270
  • 139 Zhukov IM, Belikov VV. Chromatospectrophotometric determination of flavonoids and dioxycinnamic acids in the above-ground part of Ballota nigra L. Farmatsevtichnii Zhurnal (Kiev) 1989; 5: 55-58
  • 140 Ku CT, Chen SC, Wang JP, Wu JB, Kuo SC. Studies on anti-inflammatory constituents of Leucas mollissima Wall. var. chinensis Benth. Chin Pharm J 2000; 52: 261-273
  • 141 Tofighi Z, Alipour F, Hadavinia H, Abdollahi M, Hadjiakhoondi A, Yassa N. Effective antidiabetic and antioxidant fractions of Otostegia persica extract and their constituents. Pharm Biol 2014; 52: 961-966
  • 142 Tofighi Z, Alipour F, Goodarzy S, Yassa N, Hadjiakhoondi A, Hadavinia H. Phytochemical and antidiabetic investigations of Otostegia persica essential oil from Iran. Planta Med 2009; 75: 1013-1014
  • 143 Hou FF, Zheng YF, Zhang HM, Shen SM, Du SS. Chemical constituents in Panzerina alaschanica Kupr. Zhongguo Shiyan Fangjixue Zazhi 2009; 15: 18-20
  • 144 Wang QH, Hu YR, Shao CY, Wu JS, Han NRCKT, Dai NYT, Wu RJ. Anti-inflammatory effect and high performance liquid chromatography (HPLC) analysis of the EtOAc extract from Panzeria alaschanica . Afr J Pharm Pharmacol 2015; 9: 974-981
  • 145 Shao C, Wang Q, Wu R, Wu J, Han N, Dai N. Study on chemical constituents of Panzeria alaschanica . J Chin Med Mat 2015; 38: 1668-1670
  • 146 Çitoglu G, Tanker M, Sever B. Flavonoid aglycones from Ballota saxatilis subsp saxatilis . Pharm Biol 1999; 37: 158-160
  • 147 Çitoğlu GS, Sever B, Antus S, Baitz-Gács E, Altanlar N. Antifungal flavonoids from Ballota glandulosissima . Pharm Biol 2003; 41: 483-486
  • 148 Abdelshafeek KA, Daboob AA. Investigation of flavonoids and antimicrobial activity of Ballota andreuzziana . Pharmacogn Mag 2009; 5: 203-208
  • 149 Abdelshafeek KA, Elgendy HA, El Missiry MM, Seif El Nasr MM. Structure elucidation of phenolic acids, flavonoids and hypocholesterolemic activity of Nepeta septemcrenata and Otostegia fruticosa . Der Pharma Chem 2016; 8: 357-362
  • 150 Siciliano T, Bader A, Vassallo A, Braca A, Morelli I, Pizza C, De Tommasi N. Secondary metabolites from Ballota undulata . Biochem System Ecol 2005; 33: 341-351
  • 151 Ikram M, Jehangir S, Razaq S, Kawano M. Chemical investigation of Otostegia limbata . Planta Med 1978; 37: 189-190
  • 152 Parvez M, Riaz M, Malik A. Eupatorin. Acta Crystallogr E 2001; E57: o289-o291
  • 153 Ayatollahi SAM, Kobarfard F, Asgarpanah J, Choudhary MI. Antiglycation activity of Otostegia persica (Burm.) Boiss. Afr J Biotechnol 2010; 9: 3645-3648
  • 154 Ansari S, Joshi YC, Dobhal MP, Joshi BC. Chemical constituents of the stem of Roylea elegans Wall. Pharmazie 1982; 37: 70-71
  • 155 Kisiel W, Piozzi F. Tangeretin from Ballota nigra . Polish J Chem 1995; 69: 476-477
  • 156 Aboutabl EA, Sokkar NM, Awaad AS. Phytochemical study of Otostegia fruticosa (Forssk.) and biological activity. Bull Fac Pharm Cairo Univ 2000; 38: 115-118
  • 157 Ghedadba N, Hambaba L, Ayachi A, Aberkane MC, Bousselsela H, Oueld-Mokhtar SM. Polyphenols content, antioxidant and antimicrobial activities of leaf extracts of Marrubium deserti de Noé ex Coss. Phytotherapie 2015; 13: 118-129
  • 158 Yassa N, Sharififar F, Shafiee A. Otostegia persica as a source of natural antioxidants. Pharm Biol 2005; 43: 33-38
  • 159 Uysal S, Aumeeruddy-Elalfi Z, Zengin G, Aktumsek A, Mocan A, Custodio L, Neng NR, Nogueira JMF, Ćirić A, Glamočlija J, Soković M, Mahomoodally MF. Insight into the biological properties and phytochemical composition of Ballota macrodonta Boiss. et Balansa, – an endemic medicinal plant from Turkey. Ind Crops Prod 2018; 113: 422-428
  • 160 Shrififar F, Yassa N, Shafiee A. Antioxidant activity of Otostegia persica (Labiatae) and its constituents. Iran J Pharm Res 2003; 2: 235-239
  • 161 Sahpaz S, Skaltsounis AL, Bailleul F. Polyphenols from Ballota acetabulosa . Biochem System Ecol 2002; 30: 601-604
  • 162 Hennebelle T, Sahpaz S, Ezer N, Bailleul F. Polyphenols from Ballota larendana and Ballota pseudodictamnus . Biochem System Ecol 2008; 36: 441-443
  • 163 Darbour N, Baltassat F, Raynaud J. The presence of an O-heteroside and a C-heteroside of apigenine in leaves of Ballota-foetida Lamk (Labiatae). Pharmazie 1986; 41: 605-606
  • 164 Radwan HM, El-Missiry MM, El-Nasr MM. Phytochemical investigation of Ballota undulata Benth. Bull Fac Pharm Cairo Univ 1997; 35: 83-86
  • 165 Ranganayaki S, Gusain PS, Sigh AK. . 1985; 6: 5-9
  • 166 Tofighi Z, Ostad SN, Khezrrahdoost S, Salehizadeh H, Yassa N. Potent anti-nociceptive and anti-inflammatory effects of methanol fraction of Otostegia persica extract and its components. Res J Pharmacogn 2017; 4: 23-29
  • 167 Khan A, Ahmad VU, Farooq U, Bader S, Arshad S. Two new flavonol glycosides from Otostegia limbata Benth. Chem Pharm Bull 2009; 57: 276-279
  • 168 Wang QH, Wu JS, Wu RJ, Han NRCKT, Dai NYT. Anti-inflammatory effect and isolation of phenylethanoid and acylated flavone glycosides from Panzeria alaschanica . Z Naturforsch B Chem Sci 2015; 70: 379-384
  • 169 Bao ML, Wang QH, Hao JS. In vivo antioxidative activity of 5,7,4′-trihydroxyflavone-7-O-(6″-O-[E]-coumaroyl)-β-glucopyranoside isolated from Panzeria alaschanica . Afr J Pharm Pharmacol 2017; 11: 567-572
  • 170 Bertrand MC, Tillequin F, Bailleul F. Two major flavonoids from Ballota nigra . Biochem System Ecol 2000; 28: 1031-1033
  • 171 Noor AT, Fatima I, Ahmad I, Malik A, Afza N, Iqbal L, Latif M, Khan SB. Leufolins A and B, potent butyrylcholinesterase-inhibiting flavonoid glucosides from Leucas urticifolia . Molecules 2007; 12: 1447-1454
  • 172 Khan A, Ahmad VU, Farooq U. Two new acylated flavonol glycosides from the roots of Otostegia limbata . Helv Chim Acta 2009; 92: 731-739
  • 173 Wang Q, Wu J, Wu X, Tai W, Dai N, Wu R, Han N. Anti-inflammatory and analgesic effects of two new flavone C-glycosides from Panzeria alaschanica . Monatsh Chem 2015; 146: 1025-1030
  • 174 Anwar KJ, Mosihuzaman M, Nahar N, Khan SH, Rashid R, Sultana N. Chemical studies of anti-hyperglyceamic active extract of Otostegia aucheri Bioss. J Bangladesh Chem Soc 2004; 17: 18-22
  • 175 Abdelshafeek K, Elgendy HA, ElMissiry MM, Seif ELNasr MM. Isolation and identification of some chemical constituents and antimicrobial activity of two Lamiaceae plants growing in Saini. Egypt J Chem 2016; 59: 21-31
  • 176 Dobhal MP, Joshi BC. Chemical investigations of Roylea elegans Wall. Part I. Herba Polonica 1979; 25: 95-97
  • 177 Ayatollahi SAM, Kobarfard F, Asgarpanah J, Ahmed Z. Chemical constituents from Otostegia persica . J Chem Soc Pak 2007; 29: 61-63
  • 178 Majumder PL, Maiti RN, Panda SK, Mal D, Raju MS, Wenkert E. Structure of moronic acid. J Org Chem 1979; 44: 2811-2812
  • 179 Janicsak G, Veres K, Zoltan Kakasy A, Mathe I. Study of the oleanolic and ursolic acid contents of some species of the Lamiaceae. Biochem System Ecol 2006; 34: 392-396
  • 180 Ranganayaki S, Gusain PS, Singh AK. Isolation and study of a pentacyclic triterpene from the roots of Roylea elegans Wall. J Sci Res Plants Med 1979; 1: 44-47
  • 181 Fatima I, Ahmad I, Anis I, Malik A, Afza N, Iqbal L, Latif M. New butyrylcholinesterase inhibitory steroid and peroxy acid from Leucas urticifolia . Arch Pharm Res 2008; 31: 999-1003
  • 182 Bhatt UP, Sati SC, Bahuguna RP, Semwal RB, Semwal DK. Two antidiabetic constituents from Roylea cinerea (D. Don) Baill. Nat Prod Res 2018; 32: 1281-1286
  • 183 Popa DP, Pasechnik GS. Higher terpenoids of some species of Labiatae. Chem Nat Compd 1974; 10: 529-530
  • 184 Dixit V, Irshad S, Singh H, Agnihotri P, Husain T, Khatoon S. High-performance thin-layer chromatographic determination of three therapeutic phenolic components in Leucas species. J Planar Chromatogr – Modern TLC 2017; 30: 25-31
  • 185 Vrchovská V, Spilková J, Valentão P, Sousa C, Andrade PB, Seabra RM. Antioxidative properties and phytochemical composition of Ballota nigra infusion. Food Chem 2007; 105: 1396-1403
  • 186 Tóth E, Janicsák G, Máthé I, Blunden G. Determination of phenylpropanoids in three Ballota species. J Planar Chromatogr – Modern TLC 2009; 22: 293-296
  • 187 Didry N, Seidel V, Dubreuil L, Tillequin F, Bailleul F. Isolation and antibacterial activity of phenylpropanoid derivatives from Ballota nigra . J Ethnopharmacol 1999; 67: 197-202
  • 188 Blunden G, Yang MHE, Yuan ZX, Smith BE, Patel A, Cegarra JA, Mathé I, Janicsàk G. Betaine distribution in the Labiatae. Biochem System Ecol 1996; 24: 71-81
  • 189 Janicsák G, Tóth E, Máthé I. TLC-densitometric investigations of phenylpropanoid glycosides in black horehound (Ballota nigra L.). J Planar Chromatogr – Modern TLC 2007; 20: 443-446
  • 190 Tipirdamaz R, Guvenc A. Seed fatty acids composition of Ballota cristata . Chem Nat Compd 2004; 40: 291-292
  • 191 Balansard J. Pharmacological study of Ballota foetida . C R Seances Soc Biol 1934; 115: 1295-1297
  • 192 Khokhrina TA, Peshkova VA. Stachydrine from Phlomis tuberosa and Panzeria lanata . Chem Nat Compd 1975; 10: 284
  • 193 Seidel V, Bailleul F, Tillequin F. Phenylpropanoid glycosides from Ballota nigra . Planta Med 1996; 62: 186-187
  • 194 Seidel V, Bailleul F, Libot F, Tillequin F. A phenylpropanoid from Ballota nigra . Phytochemistry 1997; 44: 691-693
  • 195 Pedersen JA. Distribution and taxonomic implications of some phenolics in the family Lamiaceae determined by ESR spectroscopy. Biochem System Ecol 2000; 28: 229-253
  • 196 Ertaş A, Boğa M, Yeşil Y. Phytochemical profile and ABTS cation radical scavenging, cupric reducing antioxidant capacity and anticholinesterase activities of endemic Ballota nigra L. subsp. anatolica P.H. Davis from Turkey. J Coast Life Med 2014; 2: 555-559
  • 197 Piault L. The lactone of some Labiatae. J Pharm Chim 1911; 1: 248-255
  • 198 Kolisnyk Y, Ochkur O, Kovalyova A, Koshoviy O. Organic acids of vegetative and generative organs of black horehound. Pharma Innovation 2014; 3: 33-37
  • 199 Marin PD, Sajdl V, Kapor S, Tatic B, Petkovic B, Duletic S. Fatty acids of the Stachyoideae. Biochem System Ecol 1992; 20: 389-392
  • 200 Abdelshafeek KA, Elgattar AA, Zarkoon AH, Alwahash MA, Shahat AA. Investigation of the volatile oils, lipid constituents and biological activity of Ballota andreuzziana, Teucrium zanonii and Verbena tenuisecta in Libya. Asian Pac J Tropical Med 2010; 3: 594-601
  • 201 Rustaiyan A, Masoudi S, Ameri N, Samiee K, Monfared A. Volatile constituents of Ballota aucheri Boiss., Stachys benthamiana Boiss. and Perovskia abrotanoides Karel. growing wild in Iran. J Ess Oil Res 2006; 18: 218-221
  • 202 Laouer H, Yabrir B, Djeridane A, Yousfi M, Beldovini N, Lamamra M. Composition, antioxidant and antimicrobial activities of the essential oil of Marrubium deserti . Nat Prod Commun 2009; 4: 1133-1138
  • 203 Chebrouk F, Hadj Mahammed M. Composition des huiles essentielles de Marrubium deserti de Noe de la region de Ghardaïa. Annales de la Faculté des Sciences et Sciences de lʼIngénieur 2009; 1: 75-81
  • 204 Chemsa AE, Zellagui A, Öztürk M, Erol E, Ceylan O, Duru ME, Gherraf N. Antibiofilm formation, antioxidant and anticholinesterase activities of essential oil and methanol extract of Marrubium deserti de Noé. J Mater Environ Sci 2018; 7: 993-1000
  • 205 Riccobono L, Ben Jemia M, Senatore F, Bruno M. Chemical composition and biological activity of the essential oil of Ballota hispanica (L.) Benth. growing wild in Sicily. Plant Biosyst 2016; 150: 1065-1071
  • 206 Todorova M, Altantsetseg S, Trendafilova A, Shatar S. Chemical composition of Panzeria lanata (L.) Bunge essential oil from Mongolian Gobi. J Ess Oil-Bearing Plants 2013; 16: 257-260
  • 207 Đorđević AS, Jovanović OP, Zlatković BK, Stojanović GS. Chemical composition of Ballota macedonica Vandas and Ballota nigra L. ssp. foetida (Vis.) Hayek essential oils – the chemotaxonomic approach. Chem Biodivers 2016; 13: 782-788
  • 208 Morteza-Semnani K, Saeedi M, Akbarzadeh M. The essential oil composition of Ballota nigra . Chem Nat Compd 2007; 43: 722-723
  • 209 Vukovic N, Sukdolak S, Solujic S, Niciforovic N. Antimicrobial activity of the essential oil obtained from roots and chemical composition of the volatile constituents from the roots, stems, and leaves of Ballota nigra from Serbia. J Med Food 2009; 12: 435-441
  • 210 Jamzad M, Rustaiyan A, Jamzad Z, Masoudi S. Essential oil composition of Salvia indica L., Thymus caucasicus Wind. Ex Ronniger subsp. grossheimii (Ronniger) Jalas. and Ballota nigra L. three Labiatae species from Iran. J Ess Oil Bearing Plants 2011; 14: 76-83
  • 211 Kolisnyk YS, Kovaleva AM, Goryacha OV. The study of the volatile oils composition obtained from vegetative and generative organs of Ballota nigra L. Visnik Farmatsii 2014; 78: 59-62
  • 212 Karemizadeh Z, Amini T, Nazari F, Habibi Z. Volatile constituents of Ballota nigra subsp. anatolica from Iran. Chem Nat Compd 2009; 45: 737-738
  • 213 Sarikaya AG. Volatile component composition of Ballota nigra subsp. anatolica at different vegetation periods in Çamlica province of Kütahya city, Turkey. Appl Ecol Env Res 2017; 15: 1929-1933
  • 214 Kaya A, Kürkçüoğlu M, Dinç M, Doğu S. Compositions of the essential oils of Ballota nigra subsp. uncinata and subsp. anatolica from Turkey. Indian J Pharm Educ Res 2017; 51: S185-S189
  • 215 Bader A, Caponi C, Cioni PL, Flamini G, Morelli I. Composition of the essential oil of Ballota undulata, B. nigra ssp. foetida and B. saxatilis . Flavour Fragr J 2003; 18: 502-504
  • 216 Fraternale D, Bucchini A, Giampieri L, Ricci D. Essential oil composition and antimicrobial activity of Ballota nigra L. ssp foetida . Nat Prod Commun 2009; 4: 585-588
  • 217 Fraternale D, Ricci D. Essential oil composition and antifungal activity of aerial parts of Ballota nigra ssp foetida collected at flowering and fruiting times. Nat Prod Commun 2014; 9: 1015-1018
  • 218 Rigano D, Marrelli M, Formisano C, Menichini F, Senatore F, Bruno M, Conforti F. Phytochemical profile of three Ballota species essential oils and evaluation of the effects on human cancer cells. Nat Prod Res 2017; 31: 436-444
  • 219 Majdi M, Dastan D, Maroofi H. Chemical composition and antimicrobial activity of essential oils of Ballota nigra subsp. kurdica from Iran. Jundishapur J Nat Pharm Prod 2017; 12: e36314
  • 220 Couladis M, Chinou IB, Tzakou O, Loukis A. Composition and antimicrobial activity of the essential oil of Ballota pseudodictamnus L. Bentham. Phytother Res 2002; 16: 723-726
  • 221 Erdogan EA, Everest A, Sonmez Ö. Antimicrobial activity of the essential oil of Ballota saxatilis subsp. brachyodonta (Boiss) P. H. Davis & Doroszenko from Turkey. J Ess Oil Bearing Plants 2014; 17: 1100-1104
  • 222 Awadh Ali NA, Alhamzy EH, Chhetri BK, Dosoky NS, Setzer WN. Chemical composition, antimicrobial, and cytotoxic activities of the essential oil of Otostegia fruticosa subsp. schimperi from Yemen. Nat Prod Commun 2017; 12: 969-972
  • 223 Özek T, Tabanca N, Demirci F, Wedge DE, Başer KHC. Enantiomeric distribution of some linalool containing essential oils and their biological activities. Rec Nat Prod 2010; 4: 180-192
  • 224 Aboutabl EA, Sokkar NM, Megid RMA, De Pooter HL, Masoud H. Composition and antimicrobial activity of Otostegia fruticosa Forssk. oil. J Ess Oil Res 1995; 7: 299-303
  • 225 Karami A, Esmaeili H, Shahbazian D. Essential oil composition of Rydingia michauxii (Briq.) Scheen & V.A. Albert endemic of Iran. Nat Prod Res 2018; 32: 229-233
  • 226 Javidnia K, Miri R, Soltani M, Khosravi AR. Chemical constituents of the essential oil of Otostegia michauxii Briq. from Iran. J Ess Oil Res 2010; 22: 1-2
  • 227 Javidnia K, Miri R, Soltani M. Essential oil composition of Otostegia persica Boiss. from Iran. J Ess Oil Res 2010; 22: 609-610
  • 228 Tofighi Z, Alipour F, Yassa N, Hadjiakhoondi A, Hadavinia H, Goodarzy S, Golestani R. Chemical composition and antioxidant activity of Otostegia persica essential oil from Iran. Int J Essen Oil Ther 2009; 3: 45-48
  • 229 Sharififar F, Mozaffarian V, Moradkhani S. Comparison of antioxidant and free radical scavenging activities of the essential oils from flowers and fruits of Otostegia persica Boiss. Pak J Biol Sci 2007; 10: 3895-3899
  • 230 Erdogan-Orhan I, Sever-Yılmaz B, Altun ML, Saltan G. Radical quenching activity, ferric-reducing antioxidant power, and ferrous ion-chelating capacity of 16 Ballota species and their total phenol and flavonoid contents. J Med Food 2010; 13: 1537-1543
  • 231 Citoglu GS, Çoban T, Sever B, Işcan M. Antioxidant properties of Ballota species growing in Turkey. J Ethnopharmacol 2004; 92: 275-280
  • 232 Rashid R, Murtaza G, Khan AK, Mir S. Antioxidant and hypoglycemic effect of Otostegia aucheri methanolic extract in streptozotocin-induced diabetic male Long-Evans rats. Acta Pol Pharm 2014; 71: 631-635
  • 233 Sharma R, Yadav D, Asif M, Jayasri MA, Agnihotri VK, Ravikumar PC. Antidiabetic and antioxidant activities of Roylea cinerea extracts: a comparative study. Indian J Exp Biol 2017; 55: 611-621
  • 234 Kechar K, Hellal B. Evaluation of the antioxidant activity of extracts of Ballota hirsuta Benth. from Tessala (Western Algeria). Phytotherapie 2017; 15: 217-221
  • 235 Makowczynska J, Grzegorczyk-Karolak I, Wysokinska H. Antioxidant activity of tissue culture-raised Ballota nigra L. plants grown ex vitro . Acta Pol Pharm 2015; 72: 769-775
  • 236 Daels-Rakotoarison DA, Seidel V, Gressier B, Brunet C, Tillequin F, Bailleul F, Luyckx M, Dine T, Cazin M, Cazin JC. Neurosedative and antioxidant activities of phenylpropanoids from Ballota nigra . Arzneimittelforschung 2000; 50: 16-23
  • 237 Seidel V, Verholle M, Malard Y, Tillequin F, Fruchart JC, Duriez P, Bailleul F, Teissier E. Phenylpropanoids from Ballota nigra L. Inhibit in vitro LDL Peroxidation. Phytother Res 2000; 14: 93-98
  • 238 Gursoy N, Tepe B. Determination of the antimicrobial and antioxidative properties and total phenolics of two “endemic” Lamiaceae species from Turkey: Ballota rotundifolia L. and Teucrium chamaedrys C. Koch. Plant Foods Hum Nutr 2009; 64: 135-140
  • 239 Couladis M, Tzakou O, Verykokidou E, Harvala C. Screening of some Greek aromatic plants for antioxidant activity. Phytother Res 2003; 17: 194-195
  • 240 Chekol YA, Desta ZY. Determination of antioxidant and antimicrobial activities of leaf extracts of Otostegia integrifolia . Chem Cent J 2018; 12: 63
  • 241 Waheed I, Ahmad M, Syed NH, Ashraf R. Investigation of phytochemical and antioxidant properties of methanol extract and fractions of Ballota limbata (Lamiaceae). Indian J Pharm Sci 2014; 76: 251-256
  • 242 Ahmed D, Arshad MA, Asghar MN, Aujla MI. Antioxidant and free radical scavenging potential of Otostegia limbata . Asian J Chem 2010; 22: 4524-4532
  • 243 Moein S, Pimoradloo E, Moein M, Vessal M. Evaluation of antioxidant potentials and α-amylase inhibition of different fractions of Labiatae plants extracts: as a model of antidiabetic compounds properties. Biomed Res Int 2017; 7319504: 1-8
  • 244 Safaeian L, Yaghoobi S, Javanmard SH, Ghasemi-Dehkordi N. The effect of hydroalcoholic extract of Otostegia persica (Burm.) Boiss. against H2O2-induced oxidative stress in human endothelial cells. Res J Pharmac 2017; 4: 51-58
  • 245 Özbek H, Çitoğlu GS, Dülger H, Uğraş S, Sever B. Hepatoprotective and anti-inflammatory activities of Ballota glandulosissima . J Ethnopharmacol 2004; 95: 143-149
  • 246 Yilmaz BS, Özbek H, Çitoğlu GS. Antinociceptive and anti-inflammatory activities of Ballota inaequidens . Pharm Biol 2006; 44: 636-641
  • 247 Elmezogi J, Zetrini A, Ben-Hussein G, Anwair M, Gbaj A, El-Ashheb M, Nahar L, Sarker SD. Evaluation of anti-inflammatory activity of some Libyan medicinal plants in experimental animals. Arch Biol Sci 2012; 64: 1058-1064
  • 248 Nabil G, Leila H. Anti-inflammatory and analgesic activities of methanolic extract from Marrubium deserti leaves and evaluation of their acute toxicity. Pharm Lett 2016; 8: 33-40
  • 249 Dulger B, Kilcik MA. Antibacterial activity of Ballota acetabulosa against methicillin-resistant Stapylococcus aureus . Asian J Chem 2011; 23: 416-418
  • 250 Dulger B, Dulger G. Antimicrobial activity of the leaves of Ballota acetabulosa on microorganisms isolated from urinary tract infection. Turk J Pharm Sci 2012; 9: 257-262
  • 251 Cock IE, van Vuuren SF. The potential of selected South African plants with anti-Klebsiella activity for the treatment and prevention of Ankylosing spondylitis . Inflammopharmacology 2014; 23: 21-35
  • 252 Quave CL, Plano LRW, Bennett BC. Quorum sensing inhibitors of Staphylococcus aureus from Italian medicinal plants. Planta Med 2011; 77: 188-195
  • 253 Ullah N, Ahmad I, Ayaz S. In vitro antimicrobial and antiprotozoal activities, phytochemical screening and heavy metals toxicity of different parts of Ballota nigra . BioMed Res Int 2014; 321803
  • 254 Quave CL, Plano LRW, Pantuso T, Bennett BC. Effects of extracts from Italian medicinal plants on planktonic growth, biofilm formation and adherence of methicillin-resistant Staphylococcus aureus . J Ethnopharmacol 2008; 118: 418-428
  • 255 Dulger G, Aki C, Dulger B. Antimicrobial activity of endemic Ballota nigra subsp anatolica in Turkey. Asian J Chem 2010; 22: 6497-6502
  • 256 Dulger G, Dulger B. Antibacterial activity of endemic Ballota nigra subsp. anatolica against some human eye pathogens from Turkey. Int J Life Sci 2017; 5: 1-3
  • 257 Ullah N, Ahmad I, Ahmad NF. In vitro antimicrobial, antiprotozoal activities and heavy metals toxicity of different parts of Ballota pseudodictamnus (L.) Benth. Pak J Pharm Sci 2017; 30: 2203-2209
  • 258 Kahaliw W, Aseffa A, Abebe M, Teferi M, Engidawork E. Evaluation of the antimycobacterial activity of crude extracts and solvent fractions of selected Ethiopian medicinal plants. BMC Complement Altern Med 2017; 17: 143
  • 259 Anwar N, Salik S, Ahmad D. Antibacterial activity of Otostegia limbata . Int J Agric Biol 2009; 11: 647-650
  • 260 Javidnia K, Miri R, Assadollahi M, Gholami M, Ghaderi M. Screening of selected plants growing in Iran for antimicrobial activity. Iran J Sci Technol A 2009; 33: 329-333
  • 261 Asghari G, Nourallahi H, Havaie SA, Issa L. Antimicrobial activity of Otostegia persica Boiss. extracts. Res Pharm Sci 2006; 1: 53-58
  • 262 Nelson K, Lyles JT, Li T, Saitta A, Addie-Noye E, Tyler P, Quave CL. Anti-acne activity of Italian medicinal plants used for skin infection. Front Pharmacol 2016; 7: 425-438
  • 263 Dulger B, Kilcik MA. Antifungal activity of Ballota acetabulosa against yeast Candida and Cryptococcus species. Asian J Chem 2011; 23: 413-415
  • 264 Hashem M. Antifungal properties of crude extracts of five Egyptian medicinal plants against dermatophytes and emerging fungi. Mycopathologia 2011; 172: 37-46
  • 265 Naz S, Farooq U, Khan A, Khan S, Sarwar R, Mirza N. Physiochemical screening and antimicrobial potential of Otostegia limbata Benth. J Chem Soc Pak 2014; 36: 683-686
  • 266 Maqsood M, Qureshi R, Ikram M, Ali S, Rafi M, Khan JA, Ahmed MS. Preliminary screening of methanolic plant extracts against human rhabdomyosarcoma cell line from salt range, Pakistan. Pak J Bot 2015; 47: 353-357
  • 267 Bahuguna RP, Jangwan JS, Singh R, Bhatt UP. In vitro cytotoxic, in vitro and in vivo antidiabetic activity of Roylea cinerea . Sci Revs Chem Commun 2015; 5: 69-76
  • 268 Marimuthu N, Viswanathan T, Radha M, Suganya J. Computational screening of the phytocompounds from the plant Ballota nigra Linn against the human papillomavirus (HPV) E6. Res J Pharm Technol 2017; 10: 3095-3097
  • 269 Fronza M, Murillo R, Ślusarczyk S, Adams M, Hamburger M, Heinzmann B, Laufer S, Merfort I. In vitro cytotoxic activity of abietane diterpenes from Peltodon longipes as well as Salvia miltiorrhiza and Salvia sahendica . Bioorg Med Chem 2011; 19: 4876-4881
  • 270 da Cruz Araujo EC, Lima MAS, Montenegro RC, Nogueira M, Costa-Lotufo LV, Pessoa C, de Moraes MO, Silveira ER. Cytotoxic abietane diterpenes from Hyptis martiusii Benth. Z Naturforsch C Biosci 2006; 61: 177-183
  • 271 Zhang Y, Ma R, Cheng S, Gu G. Marrubenol inhibits osteosarcoma cancer cell growth by inducing autophagic cell death and inhibiting cancer cell migration and invasion. J Balkan Union of Oncology 2018; 23: 729-734
  • 272 Xiao CJ, Liu YC, Luo SH, Hua J, Liu Y, Li SH. Localisation of two bioactive labdane diterpenoids in the peltate glandular trichomes of Leonurus japonicus by laser microdissection coupled with UPLC-MS/MS. Phytochem Anal 2017; 28: 404-409
  • 273 Ateyyat MA, Al-Mazraʼawi M, Abu-Rjai T, Shatnawi MA. Aqueous extracts of some medicinal plants are as toxic as Imidacloprid to the sweet potato whitefly, Bemisia tabaci . J Insect Sci 2009; 9: 15
  • 274 Al-Alawi MS. Acaricidal activity of medicinal plants against the developmental stage of the two spotted spider mite, Tetranychus urticae (Acari: Tetranychidae). Int J Agr Res 2014; 9: 38-46
  • 275 Dube FF, Tadesse K, Birgersson G, Seyoum E, Tekie H, Ignell R, Hill SR. Fresh, dried or smoked? Repellent properties of volatiles emitted from ethnomedicinal plant leaves against malaria and yellow fever vectors in Ethiopia. Malar J 2011; 10: 375
  • 276 Khan J, Anjum SI, Khan I, Rehman FU, Khan A. Larvicidal and development retarding effects of hexane crude extract of Otostegia limbata on 3rd instar larvae of Drosophila melanogaster Meign (Diptera: Drosophilidae). J Entomol Zool Stud 2015; 3: 6-9
  • 277 Salari E, Ahmadi K, Zamani R. Study on the effects of acetonic extract of Otostegia persica (Labiatae) on three aphid species and one stored product pest. Adv Environ Biol 2010; 4: 346-349
  • 278 Pascual-Villalobos MJ, Robledo A. Anti-insect activity of plant extracts from the wild flora in southeastern Spain. Biochem System Ecol 1999; 27: 1-10
  • 279 Haq RU, Farooq U, Wahab A, Raza M, Ahmad VU, Khan RA. Investigation of antitussive and toxicological activity of Ballota limbata in mice. Pharm Biol 2011; 49: 627-632
  • 280 Vural K, Ezer N, Erol K, Sahin FP. Anxioloytic and antidepressant activities of some Ballota species. J Fac Pharm Gazı 1996; 13: 29-32
  • 281 Hajhashemi V, Rabbani M, Asghari GR, Karami-Saravi Z. Effects of Otostegia persica (Burm.f.) Boiss on morphine withdrawal syndrome in mice. Iranian J Pharm Res 2004; 3: 171-175
  • 282 Ansari F, Shafaroodi H, Asgarpanah J. Anticonvulsant activity of Otostegia persica (Burm.) Boiss. Biosci Biotechnol Res Asia 2014; 11: 733-737
  • 283 Çitoğlu GS, Özbek H, Severa B. Antinociceptive activity of Ballota glandulosissima Hub.-Mor & Patzak. Eastern J Med 2005; 10: 24-28
  • 284 Nusier MK, Bataineh HN, Bataineh ZM, Daradka HM. Effects of Ballota nigra on glucose and insulin in alloxan-diabetic albino rats. Neuro Endocrinol Lett 2007; 28: 470-472
  • 285 Nusier MK, Bataineh HN, Bataineh ZM, Daradka HM. Effects of Ballota nigra on blood biochemical parameters and insulin in albino rats. Neuro Endocrinol Lett 2007; 28: 473-476
  • 286 Qazan WSh. Hypolipidaemic effects of Ballota undulata in rabbits. Pak J Biol Sci 2008; 11: 1169-1172
  • 287 Ebrahimpoor MR, Khaksar Z, Noorafshan A. Anti-diabetic effect of orally administered Otostegia persica extract on streptozotocin diabetic rats. Comp Clin Pathol 2011; 20: 523-525
  • 288 Manzari-Tavakoli A, Pouraboli I, Yaghoobi MM, Mehrabani M, Mirtadzadini SM. Antihyperglycemic, antilipid peroxidation, and insulin secretory activities of Otostegia persica shoot extract in streptozotocin-induced diabetic rats and in vitro C187 pancreatic β-cells. Pharm Biol 2013; 51: 253-259
  • 289 Takhtfooladi MA, Asghari A, Hoseinzadeh HA, Mokhtari F. Effect of Otostegia persica extract on ischemia/reperfusion induced renal damage in diabetic rats. A biochemical study. Acta Cir Bras 2016; 31: 417-421
  • 290 Akbarzadeh S, Bazzi P, Daneshi A, Nabipour I, Pourkhalili K, Mohebbi GH, Sartavi K, Abdi MR, Mirzaei M, Bargahi A. Anti-diabetic effect of Otostegia persica extract on diabetic rats. J Med Plants Res 2012; 6: 3176-3180
  • 291 Ebrahimpoor-Mashhadi MR, Khaksar Z, Noorafshan A, Mogheisi B. Stereological study of the effects of orally administrated Otostegia persica extract on pancreatic beta cells in male diabetic rats. Comp Clin Pathol 2014; 23: 761-767
  • 292 Rezaian M, Shomali T, Dilmaghanian A, Rassouli A. Ethanolic extract of Otostegia persica ameliorates bone loss in diabetic rats irrespective to its glucose lowering effect. Comp Clin Pathol 2014; 23: 1147-1151
  • 293 Shewamene Z, Abdelwuhab M, Birhanu Z. Methanolic leaf extract of Otostegia integrifolia Benth reduces blood glucose levels in diabetic, glucose loaded and normal rodents. BMC Complement Altern Med 2015; 15: 19
  • 294 Bhatt UP, Sati SC, Chandra S, Kumar S, Anthwal A, Singh R, Singh D, Kumar N, Kumar A, Bahuguna RP. Evaluation of in vivo and in vitro anti-diabetic activity of Roylea cinerea . Int J Pharm Sci Rev Res 2015; 32: 33
  • 295 Suthar S, Patel R. The antihyperlipidaemic activity of aqueous Leucas urticifolia extract in Triton WR-1339 induced hyperlipidaemic rats. Int J Pharm Technol 2012; 4: 4314-4324
  • 296 Qazan WSh. Effects of short and long term treatment of Ballota undulata on female albino rats fertility and pregnancy. Pak J Biol Sci 2008; 11: 638-642
  • 297 Ganjali A, Sotoudeh A, Jahanshahi A, Takhtfooladi MA, Bazzazan A, Roodbari N, Harati MP. Otostegia persica extraction on healing process of burn wounds. Acta Cir Bras 2013; 28: 407-411
  • 298 Takhtfooladi MA, Takhtfooladi HA, Moayer F, Karimi P, Asl HA. Effect of Otostegia persica extraction on renal injury induced by hindlimb ischemia-reperfusion: a rat model. Int J Surg 2015; 13: 124-130
  • 299 Safaeian L, Ghasemi-Dehkordi N, Javanmard ShH, Namvar H. Antihypertensive and antioxidant effects of a hydroalcoholic extract obtained from aerial parts of Otostegia persica (Burm.) Boiss. Res Pharm Sci 2015; 10: 192-199
  • 300 Yeshanew S, Mekonnen Y. The effect of Otostegia integrefolia leaf extracts on the packed cell volume, body weight and survival time of Plasmodium berghei infected mice. Int J Trop Med 2013; 8: 129-134
  • 301 Nateghpour M, Farivar L, Souri E, Hajjaran H, Mohebali M, Haghi AM. The effect of Otostegia persica in combination with chloroquine on chloroquine-sensitive and chloroquine-resistant strains of Plasmodium berghei using in-vivo fixed ratios method. Iranian J Pharm Res 2012; 11: 583-588
  • 302 Dua VK, Verma G, Agarwal DD, Kaiser M, Brun R. Antiprotozoal activities of traditional medicinal plants from the Garhwal region of North West Himalaya, India. J Ethnopharmacol 2011; 136: 123-128
  • 303 Bezenjani SN, Pouraboli I, Afshar RM, Mohammadi G. Hepatoprotective effect of Otostegia persica Boiss. shoot extract on carbon tetrachloride-induced acute liver damage in rats. Iranian J Pharm Res 2012; 11: 1235-1241
  • 304 Akbartabar Toori M, Joodi B, Mehraban F, Mostafazadeh M, Ghavamizadeh M, Sadeghi H, Jafari M, Sadeghi H, Talebianpoor MS. Hepatoprotective activity of aerial parts of Otostegia persica against carbon tetrachloride-induced liver damage in rats. Avicenna J Phytomed 2015; 5: 238-246
  • 305 Upadhyay G, Malik J, Joshi R, Lakshmayya L, Singh UK. Hepatoprotective potential of lyophilized hydro-alcoholic extract of Roylea elegans Wall. against CCl4 and PCM induced hepatotoxicity in Wistar rats. Ann Pharmacol Pharmaceut 2017; 2: 1045
  • 306 Hashemi F, Zarei MA. Tyrosinase inhibitory activity within hexane extract of ten screened plants from Kurdistan Province of Iran. Int J Adv Biol Biomed Res 2014; 2: 2795-2799
  • 307 de Sales PM, de Souza PM, Simeoni LA, Magalhaes PDO, Silveira D. α-Amylase inhibitors: a review of raw material and isolated compounds from plant source. J Pharm Pharm Sci 2012; 15: 141-183