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Antifungal Flavonoids from Ballota glandulosissima
Pharmaceutical Biology
Abstract
Abstract The flavonoids kumatakenin (1), pachypodol (2), 5-hydroxy-7,3′,4′-trimethoxyflavone (3), velutin (4), salvigenin (5), retusin (6) and corymbosin (7) have been isolated from the aerial parts of Ballota glandulosissima Hub.-Mor & Patzak. Among them, 2–4 and 7 have not been reported previously in the genus Ballota. The antibacterial and antifungal activities of 1–4 and 6 were tested against Bacillus subtilis, Staphylococcus aureus, Staphylococcus faecalis, Echerichia coli, Pseudomonas aeruginosa, Candida albicans, Candida krusei and Candida galabrata.
... The main components of Ballota species are flavonoids, labdan diterpenoids and phenyl propanoids. Diterpenoids (hispanolone, ballonigrine, dehydrohispanolone) and 14 flavonoids (kumatakenin (jaranol), pachypodol, 5-hydroxy-7,3',4' trimethoxy flavone, velutin, velutol, salvigenol, korimbosol, retusol, corymbosine, 5-hydroxy 3,7,4'trimethoxyflavone, retusin, 5-hydroxy 7, 4'dimethoxy flavone, flindulatine, ladanein) were isolated from different Ballota species and chemically characterized and analyzed by HPLC ( Çitoğlu et al. 1998, Çitoğlu et al. 1999, Saltan Çitoğlu et al. 2003a, Saltan Çitoğlu et al. 2003b). Pachypodol (Ro 09-0179) was first isolated from Plectranthus cylindraceus, Pogostemon cablin, Heterotheca grandiflora, Aglaia andamanica, Euodia glabra and Larrea tridentata (Valesi et al. 1972, Fraser & Lewis 1973, Sakakibara et al. 1976, Wollenweber et al. 1985, Miyazawa et al. 2000, Orabi et al. 2000) has antiviral effect against RNA virus such as poliovirus and rhinovirus. ...
... This antiviral effect was shown by inhibiting RNA polymerase in viral RNA synthesis and inhibiting viral replication ( Arita et al. 2015, Ishitsuka et al. 1986, Ninomiya et al. 1985, Pérez & Carrasco 1992. Some of these flavonoids isolated from B. glandulosissima, a species naturally growing in southern Anatolia, has also been reported to have antimicrobial activity (Saltan Çitoğlu et al. 2003a, Saltan Çitoğlu et al. 2003b). ...
... Although it is well reported that Ballota species have antinociceptive, anti-inflammatory, hepatoprotective, antilisterial, antiproliferative and antioxidant activities ( Çitoğlu et al. 1998, Çitoğlu et al. 1999, Saltan Çitoğlu et al. 2003a, Saltan Çitoğlu et al. 2003b, Erdoğan-Orhan et al. 2010, Özbek et al. 2004, Rigano et al. 2016, Saltan Çitoğlu et al. 2004a, Saltan Çitoğlu et al. 2004b, Saltan Çitoğlu et al. 2004c, Sever Yılmaz et al. 2005, Sever Yılmaz et al. 2006), researches on the antiviral activities of Ballota species with different biological activities are limited only to picornaviruses. Ballota species, which have different components one of which is pachypodol, have not been searched for antiviral activity against HRSV. ...
In order to find new and effective antiviral agents from natural sources, the antiviral properties of methanol and
aqueous extracts of Ballota glandulosissima Hub.-Mor. & Patzak were evaluated by Colorimetric XTT test against Respiratory
syncytial virus (RSV). The concentration required to provide 50% protection against cytopathic effects caused by the virus was
defined as EC50, the selectivity index (SI) was determined from the ratio of CC50 (50 % Cytotoxic concentration) to EC50. The
results showed that both the methanol (EC50 = 12.45 μg/mL; SI = 24.84) and aqueous extracts (EC50 = 19.12 μg/mL; SI =
24.59) of B. glandulosissima had almost the same strong anti-RSV activity as well as ribavirin, used as a positive control
against RSV (EC50 = 3.25 μg/mL, SI = 34.89). In conclusion, we can say that B. glandulosissima extracts are worthy of further
studies in order to develop an alternative to the drugs used in clinical practice against RSV. This is the first report on the anti-
RSV activity of B. glandulosissima.
... Another study reported that Ballota acetabulosa is used for the treatment of haemorrhoids as infusion in folk medicine (12). The antimicrobial (20) and antioxidant activities (21) of all Ballota species growing in Turkey was recently reported as well as the antifungal activities of some flavonoids isolated from Ballota glandulosissima (22). ...
... The main components of the Ballota species are flavonoids, labdane diterpenoids and phenylpropanoids (26). In our previous studies, three diterpenoids (hispanolone, ballonigrine, dehydrohispanolone) and ten flavonoids (kumatakenin, pachypodol, 5-hydroxy-7,3',4'trimethoxyflavone, velutin, corymbosin, 5-hydroxy-3,7,4'-trimethoxyflavone, retusin, 5-hydroxy-7,4'-dimethoxyflavone, 5-hydroxy-3,6,7,4'-tetramethoxyflavone, ladanein) were isolated, chemically characterized and analysed by HPLC in different Ballota species (15,22,(25)(26)(27). ...
... This paper is a part of our on-going studies on this genus (15,(20)(21)(22)(23)(24)(25)(26)(27). The aim of this work is to assess the antilisterial activities of all Ballota species growing in Turkey. ...
... Amomum Roxb. is a large genus with about 250 species and belongs to Zingiberaceae. In recent years, 21 Amomum species have been recorded in Vietnam [1]. e chemistry of a few Amomum species from Vietnam has been studied [2][3][4]. ...
... Kaempferol is much less active than quercetin, showing MIC values against S. aureus and B. cereus of 500 μg/mL, but it is strongly active against E. coli (MIC 50 25 μg/mL) [20]. Çitoglu et al. noted that the presence of free hydroxyl groups at C-5 and C-4′ was not significant for strong antibacterial activity of kaempferol methyl ethers [21]. No activity was observed for 6 showing that the free hydroxyl group at C-3 was not critical for strong antibacterial activity. ...
Methylated flavonols form a special group with modulating biological activities in comparison with kaempferol and quercetin. The present study isolated ten compounds including two kaempferol methyl ethers: 5-hydroxy-3,7,4′-trimethoxyflavone (1), 3-hydroxy-5,7,4′-trimethoxyflavone (6); four quercetin methyl ethers: retusin (5-hydroxy-3,7,3′,4′-tetramethoxyflavone) (4), 3,5-dihydroxy-7,3′,4′-trimethoxyflavone (5), 3,4′-dihydroxy-5,7,3′-trimethoxyflavone (7), and 3,5,7,3′,4′-pentamethoxyflavone (9); β-sitosterol (2); 5-hydroxy-1-(4′-hydroxyphenyl)eicosan-3-one (3); p-hydroquinone (8); and vanillic acid (10) from the rhizomes and fruit of Amomum koenigii J.F.Gmel. (Zingiberaceae). Their structures were determined by MS, NMR, and X-ray spectroscopic techniques. Among the methylated flavonols, 1, 4–7, and 9 were isolated for the first time from the rhizomes, while 1, 4, and 5 were isolated from the fruit. Compounds 2, 3, 7, 8, and 10 were reported for the first time from the species. Three main methylated flavonols 1, 4, and 5 were quantitatively analyzed in the rhizomes of A. koenigii by RP-HPLC-DAD; their contents were determined to be 1.81% (1), 1.38% (4), and 1.76% (5). The antimicrobial assay against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus, Aspergillus niger, Fusarium oxysporum, Candida albicans, and Saccharomyces cerevisiae and antioxidant DPPH scavenging test were performed for the isolated methylated flavonols.
... On the basis of physicochemical properties, spectral data (UV, IR, 1D NMR, 2D NMR, EI-MS). Compound 1 have oxygenation patterns as apigenin 5,7,4′, Compounds 2 and 3 have oxygenation patterns as luteolin 5,7,3′,4′ and compound 4 is a 6luteolin substituted and by comparing the data with the literature values the structures were identified to be 5-hydroxy-7,4′-dimethoxyflavone 1 [28], 5-hydroxy-7,3′,4′-trimethoxyflavone 2 [29,30], 5,4′-dihydroxy-7, 3′-dimethoxyflavone, velutin 3 [30][31][32], 5,4′-dihydroxy-6,7,3′-trimethoxyflavone, cirsilineol 4 [33,34]. 5,4′-dihy droxy-7,3′-dimethoxyflavone, velutin 3 was isolated earlier from several plants [32,35,36]. ...
... On the basis of physicochemical properties, spectral data (UV, IR, 1D NMR, 2D NMR, EI-MS). Compound 1 have oxygenation patterns as apigenin 5,7,4′, Compounds 2 and 3 have oxygenation patterns as luteolin 5,7,3′,4′ and compound 4 is a 6luteolin substituted and by comparing the data with the literature values the structures were identified to be 5-hydroxy-7,4′-dimethoxyflavone 1 [28], 5-hydroxy-7,3′,4′-trimethoxyflavone 2 [29,30], 5,4′-dihydroxy-7, 3′-dimethoxyflavone, velutin 3 [30][31][32], 5,4′-dihydroxy-6,7,3′-trimethoxyflavone, cirsilineol 4 [33,34]. 5,4′-dihy droxy-7,3′-dimethoxyflavone, velutin 3 was isolated earlier from several plants [32,35,36]. ...
Background:
Lampaya medicinalis Phil. (Verbenaceae) is a plant used by Aymara and Quechua ethnic groups from Northern Chile as folk medicine in the treatment and cure of various diseases. The aim of this study was to investigate the in vitro antioxidant activity, total phenols content, total flavonoids content, total antioxidant activity, reducing power, brine shrimp cytotoxicity and identify the principal chemical constituents.
Methods:
The crude hydroethanolic extract (HEE) and its partitioned fraction: hexane (HF), dichloromethane (DF), ethyl acetate (EAF), n-butanol (BF) and soluble residual aqueous fraction (RWF) were evaluated for their antioxidant activity using different assays namely, DPPH, ABTS, FRAP, β-carotene bleaching assay. The content of total phenolics and total flavonoids were measured by Folin-Ciocalteau and by the AlCl3 colorimetric method, respectively. Reducing power was determined by phosphomolybdate and hexacyanoferrate (III) methods. Biotoxicity assays were performed on shrimps of Artemia salina. The EAF was fractionated using chromatographic methods.
Results:
Considerable amount of phenolic and flavonoid contents were recorded in the hydroethanolic extract (HEE) and its derived fractions. Although HEE and all its derived fractions exhibited good antioxidant activities, the most distinguished radical scavenging potential was observed for ethyl acetate fraction (EAF). EAF showed the higher radical scavenging activity by DPPH (95%) and by ABTS (98%), antioxidant activity by FRAP (158.18 ± 5.79 mg equivalent Trolox/g fraction), β-carotene bleaching assay (86.8%), the highest total phenols content (101.26 ± 1.07 mg GAE/g fraction), the highest total flavonoids content (66.26 ± 3.31 μg quercetin/g fraction). The EAF extract showed an reducing power of 78% and 65% using the phosphomolybdate and hexacyanoferrate (III) assays, respectively.Four flavonoids, two p-hydroxyacetophenone derivatives and one iridoid were isolated from Lampaya medicinalis for the first time.
Conclusion:
EtOAc soluble fraction (EAF) shows the strongest antioxidant activity, and it can be attributed to its high content in phenolic and flavonoid compounds. It can be concluded that L.medicinalis can be used as an effective natural source of antioxidant, as ethnomedicine and as a commercial basis for the development of nutraceuticals.
... In previous studies, three diterpenoids (hispanolone, ballonigrine, dehydrohispanolone) and ten flavonoids (kumatakenin, pakipodol, 5-hydroxy-7,3',4' trimethoxy flavone, velutin, corymbosin, 5-hydroxy-3,7,4'-trimethoxyflavone, retusine, 5-hydroxy-7,4'-dimethoxy flavone, flindulatin, ladanein) were isolated, chemically characterised and analysed by HPLC in different Ballota species (Ç itoglu et al., 1998;Ç itoglu et al., 1999;Sever, 2000;Ç itoglu et al., 2003;Ç itoglu et al., 2004a). This paper is a part of our on-going studies (Ç itoglu et al., 1998;Ç itoglu et al., 1999;Sever, 2000;Ç itoglu et al., 2003;Ç itoglu et al., 2004a) on this genus. ...
... In previous studies, three diterpenoids (hispanolone, ballonigrine, dehydrohispanolone) and ten flavonoids (kumatakenin, pakipodol, 5-hydroxy-7,3',4' trimethoxy flavone, velutin, corymbosin, 5-hydroxy-3,7,4'-trimethoxyflavone, retusine, 5-hydroxy-7,4'-dimethoxy flavone, flindulatin, ladanein) were isolated, chemically characterised and analysed by HPLC in different Ballota species (Ç itoglu et al., 1998;Ç itoglu et al., 1999;Sever, 2000;Ç itoglu et al., 2003;Ç itoglu et al., 2004a). This paper is a part of our on-going studies (Ç itoglu et al., 1998;Ç itoglu et al., 1999;Sever, 2000;Ç itoglu et al., 2003;Ç itoglu et al., 2004a) on this genus. Ballota glandulossima, known as karınca somurcagı in Silifke, is claimed to be useful in respiratory disorders and is used as a sedative drug. ...
Water extract of Ballota glandulosissima Hub.-Mor & Patzak (Lamiaceae) (BG) was investigated for anti-inflammatory activity using the carrageenan-induced rat paw oedema test and for hepatoprotective effect on carbon tetrachloride (CCl(4))-induced hepatotoxicity in rats. Biochemical parameters of hepatic damage such as serum aspartate aminotransferase (AST), alanine aminotransferase (ALT), alkaline phosphatase (ALP) and bilirubin concentrations were determined. CCl(4) (0.8 mL/kg i.p. for 7 days) treatment increased the serum AST, ALT, ALP and bilirubin levels significantly as compared to controls. Treatment of animals with BG (100 mg/kg, i.p.) +CCl(4) (0.8 mL/kg i.p.) for 7 days significantly ameliorated the levels of AST, ALT and ALP elevated by the CCl(4) treatment alone. The results of biochemical tests were also confirmed by histopathological examination. BG together with CCl(4) treatment decreased the balloning degeneration but did not produced apoptosis of hepatocytes, centrilobular and bridging necrosis observed in the CCl(4) treatment alone. BG, at 100 mg/kg per os, showed a significant reduction (34.22%) in rat paw oedema induced by carrageenan. The reference anti-inflammatory drugs etodolac (50 mg/kg, p.o.) and indomethacin (3 mg/kg, i.p.) significantly reduced the oedeme by 43.42 and 95.70%, respectively. The present study reveals that the water extract of Ballota glandulosissima possesses promising protective activity against CCl(4) induced hepatic damage and anti-inflammatory activity in rats.
... The compounds that achieved the highest scores in docking with each target were Corymbosin (Compound 83), and Moslosooflavone (Compound 70). Corymbosin, a glucoside isolated from Ballota glandulosissima [45], was investigated for its potential to ameliorate apoptosis process of endothelial cells [46]. Moslosooflavone was reported to have anti-oxidant activity and anti-inflammatory activity, exhibiting the potential for treating DILI [47,48]. ...
Huanglian Jiedu Decoction (HJD) is a well-known Traditional Chinese Medicine formula that has been used for liver protection in thousands of years. However, the therapeutic effects and mechanisms of HJD in treating drug-induced liver injury (DILI) remain unknown. In this study, a total of 26 genes related to both HJD and DILI were identified, which are corresponding to a total of 41 potential active compounds in HJD. KEGG analysis revealed that Tryptophan metabolism pathway is particularly important. The overlapped genes from KEGG and GO analysis indicated the significance of CYP1A1, CYP1A2, and CYP1B1. Experimental results confirmed that HJD has a protective effect on DILI through Tryptophan metabolism pathway. In addition, the active ingredients Corymbosin, and Moslosooflavone were found to have relative strong intensity in UPLC-Q-TOF-MS/MS analysis, showing interactions with CYP1A1, CYP1A2, and CYP1B1 through molecule docking. These findings could provide insights into the treatment effects of HJD on DILI.
... This compound also inhibits the production of pro-inflammatory cytokines, such as TNF-α, IL-6, and IL-1β. [37][38][39] The fissisaine has not been studied as active against the interleukin-1β receptor. However, it is protoberberine alkaloid because its structure is similar to other protoberberine compounds such as berberine. ...
Arcangelisia flava (L.) Merr has been traditionally used to treat jaundice, liver disease, diarrhea, fever, and inflammation. Judging from its potential, scientific evidence of this plant extract as an inhibitor of interleukin-1β is still lacking. This study aims to investigate the phytochemical compounds present in the 70% ethanol extract of Arcangelesia flava stems by LC-MS/MS and to elucidate the ligand-protein interactions through in-silico studies. The extract was found to contain alkaloids, flavonoids, furanoditerpene, hydroxyquinoline, phenylpropanoid, phenol, and fatty acids. According to molecular docking of the 15 compounds analyzed by LC-MS/MS, the compounds 3-hydroxy-3',4',5'-trimethoxyflavone (ΔG=-7.72 kcal/mol), fisisaine (ΔG=-6,91 kcal/mol), and demethyleneberberine (ΔG=-6.85 kcal/mol), which demonstrated the highest affinity for binding to the protein target. In addition, active amino acids contribute to this interaction by creating strong hydrogen bonds, such as MET148, LYS 103, and THR300. Phytochemical compounds from Arcangelesia flava may serve as adjunctive therapy or a promising source of advanced structures in drug discovery for treatments targeting interleukin-1β
... Numerous experimental studies have examined the pharmacological effects of pachypodol, as represented in Figure 1. For example, 3,7,3 -trimethyl ether (or 4 ,5-Dihydroxy-3,3 ,7-trimethoxyflavone), belonging to the class of flavonoids, has shown anti-mutagenic activity [18], anti-emetic activity [42], inhibition of water-splitting enzyme [43], cytotoxic activity [44], anti-fungal activity [45], and anti-cancer activity [40]. Kim et al., in 2019 [46], stated that this molecule is highly intriguing due to its defensive properties, which have prompted computer studies on its capacity for radical scavenging. ...
As is well known, plant products have been increasingly utilized in the pharmaceutical industry in recent years. By combining conventional techniques and modern methodology, the future of phytomedicines appears promising. Pogostemon Cablin (patchouli) is an important herb used frequently in the fragrance industries and has various therapeutic benefits. Traditional medicine has long used the essential oil of patchouli (P. cablin) as a flavoring agent recognized by the FDA. This is a gold mine for battling pathogens in China and India. In recent years, this plant has seen a significant surge in use, and approximately 90% of the world’s patchouli oil is produced by Indonesia. In traditional therapies, it is used for the treatment of colds, fever, vomiting, headaches, and stomachaches. Patchouli oil is used in curing many diseases and in aromatherapy to treat depression and stress, soothe nerves, regulate appetite, and enhance sexual attraction. More than 140 substances, including alcohols, terpenoids, flavonoids, organic acids, phytosterols, lignins, aldehydes, alkaloids, and glycosides, have been identified in P. cablin. Pachypodol (C18H16O7) is an important bioactive compound found in P. cablin. Pachypodol (C18H16O7) and many other biologically essential chemicals have been separated from the leaves of P. cablin and many other medicinally significant plants using repeated column chromatography on silica gel. Pachypodol’s bioactive potential has been shown by a variety of assays and methodologies. It has been found to have a number of biological activities, including anti-inflammatory, antioxidant, anti-mutagenic, antimicrobial, antidepressant, anticancer, antiemetic, antiviral, and cytotoxic ones. The current study, which is based on the currently available scientific literature, intends to close the knowledge gap regarding the pharmacological effects of patchouli essential oil and pachypodol, a key bioactive molecule found in this plant.
... Flavonoids are mainly considered plant secondary metabolites [35,36] that play protective roles against UV radiation [37] and reactive oxygen species (ROS) [38]. They are essential in plant-pollinator interactions [39] and protect the plant cell host from pathogenic microbes, among which plant-fungi interactions and the antifungal properties of flavonoids are especially well described [40][41][42][43][44][45][46][47][48][49]. Thus, flavonoids, despite the positive role that they play in plant interactions with mycorrhizal fungi [50,51], are generally described as harmful to fungal cells. ...
Flavonoids are chemical compounds that occur widely across the plant kingdom. They are considered valuable food additives with pro-health properties, and their sources have also been identified in other kingdoms. Especially interesting is the ability of edible mushrooms to synthesize flavonoids. Mushrooms are usually defined as a group of fungal species capable of producing macroscopic fruiting bodies, and there are many articles considering the content of flavonoids in this group of fungi. Whereas the synthesis of flavonoids was revealed in mycelial cells, the ability of mushroom fruiting bodies to produce flavonoids does not seem to be clearly resolved. This article, as an overview of the latest key scientific findings on flavonoids in mushrooms, outlines and organizes the current state of knowledge on the ability of mushroom fruiting bodies to synthesize this important group of compounds for vital processes. Putting the puzzle of the current state of knowledge on flavonoid biosynthesis in mushroom cells together, we propose a universal scheme of studies to unambiguously decide whether the fruiting bodies of individual mushrooms are capable of synthesizing flavonoids.
... All compounds were isolated for the first time from plants of the Cousinia genus. e isolated compounds ( Figure 1) were identified to be grindelic acid (1) [54], retusine (2) [55], pachipodol (3) [56], jaranol (4) [57], penduletin (5) [58], casticin (6) [59], and 5,7,3′-trihydroxy-3,4′-dimethoxyflavone (7) [60]. ...
A biologically guided isolation of secondary metabolites from Cousinia alata Schrenk wild plant growing in Akmola region, Kazakhstan, led to the isolation of the bioactive diterpene grindelic acid (1). Six flavonoids were also isolated and identified as retusine (2), pachipodol (3), jaranol (4), penduletin (5), casticin (6), and 5, 7, 3′-trihydroxy-3, 4′-dimethoxyflavone (7). Penduletin (5) showed moderate cytotoxic activity assay. Grindelic acid exhibited promising cytotoxic activity against the Artemia salina nauplii and antibacterial activity against Staphylococcus aureus, Bacillus cereus, and Salmonella enteritidis. The presence of the essential pharmacophoric features of histone deacetylase (HDAC) inhibitors in the structure of grindelic acid encouraged us to run a molecular docking study against the HDAC enzyme to understand its mechanism of action on a molecular level. Grindelic acid showed a binding mode of interaction similar to that of the cocrystallized ligand and exhibited good binding affinity against HDAC with the binding free energy of −18.70 kcal/mol. The structures of isolated compounds were determined by MS, 1D, and 2D NMR spectroscopy methods. Compounds (1–7) were isolated for the first time from Cousinia genus.
... 5 The antimicrobial activities [6][7][8] and the antioxidant activities 9 of Ballota species were recently reported as well as the antifungal activities of some flavonoids isolated from 2 species. 10,11 The water extract has been reported to have antinociceptive, antiinflammatory, and hepatoprotective activities. 12 In Europe, the polar extracts of the flowering aerial parts of Ballota are commonly used due to their neurosedative activity. ...
In the present study, the chemical composition of the essential oils from aerial parts of Ballota nigra subsp. uncinata (Bég.) Patzak collected in Sicily was evaluated by gas chromatography (GC) and GC-mass spectrometry. The main components of the oil were ( E)-phytol (20.0%), α-pinene (9.0%), hexahydrofarnesyl acetone (5.7%), and α-selinene (5.1%). Cluster analysis of the essential oil compositions of all the taxa belonging to B. nigra s.l. group was performed.
... Ballota species have been used in Turkish folk medicine as antiulcer, antispasmodic, and sedative agents (Ç itoglu et al., 1998). In our previous studies, three diterpenoids (hispanolone, ballonigrine, dehydrohispanolone) and ten flavonoids (kumatakenin, pakipodol, 5-hydroxy-7,3 0 ,4 0 -trimethoxyflavone, velutin, corymbosin, 5-hydroxy-3,7,4 0 -trimethoxyflavone, retusin, 5-hydroxy-7,4 0 -trimethoxyflavone, 5-hydroxy-3,6,7,4 0tetramethoxyflavone, ladanein) were isolated, chemically characterized, and analyzed by HPLC in different species of Ballota (Ç itoglu et al., 1998, 1999, 2003Sever, 2000). Although Ballota inaequidens Hub.-Mor. ...
Two diterpenoids (hispanolone 1, ballonigrine 2) and six flavonoids (5-hydroxy-3,7,4′-trimethoxyflavone 3, retusin 4, 5-hydroxy-7,4′-dimethoxyflavone 5, pachypodol 6, 5-hydroxy-3,6,7,4′-tetramethoxyflavone 7, 5-hydroxy-7,3′,4′-trimethoxyflavone 8) have been isolated from the aerial parts of Ballota inaequidens. Hub.-Mor. & Patzak. Among them, 7 has not been reported previously in the genus Ballota.. The antibacterial and antifungal activities of 1–4, 6, and 8 were tested against Bacillus subtilis., Staphylococcus aureus., Escherichia coli., Pseudomonas aeruginosa., Candida albicans., and Candida crusei..
... [7][8][9] Ballota acetabulosa has been reported to be used for treatment of hemorrhoids as an infusion. 10 In our ongoing studies on the search for various biological activities of Turkish Ballota species, [11][12][13][14][15][16][17][18] Antioxidant activity of the ethyl acetate, methanol, and water extracts (48 extracts in total) from these species was tested in three different test systems-2,2-diphenyl-1-picrylhydrazyl (DPPH) radical quenching, ferric-reducing antioxidant power (FRAP), and ferrous-ion chelating capacity-at 1 mg=mL. Total phenol and flavonoid contents of the extracts were determined spectrophotometrically with Folin-Ciocalteau and aluminum chloride reagents, respectively. ...
The ethyl acetate, methanol, and water extracts of 16 Ballota species (Family Lamiaceae)-Ballota acetabulosa, Ballota antalyanse, Ballota cristata, Ballota glandulosissima, Ballota inaequidens, Ballota larendana, Ballota latibracteolata, Ballota macrodonta, Ballota nigra ssp. anatolica, B. nigra ssp. foetida, B. nigra ssp. nigra, B. nigra ssp. uncinata, Ballota pseudodictamnus ssp. lycia, Ballota rotundifolia, Ballota saxatilis ssp. brachyodonta, and B. saxatilis subsp. saxatilis-were screened for their 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical quenching, ferric-reducing antioxidant power, and ferrous ion-chelating capacity at 1mg/mL. Hispanolone, a major diterpene found in the Ballota genus, was also tested in the same manner. Total phenol and flavonoid contents of the extracts were determined by Folin-Ciocalteau and AlCl(3) reagents, respectively. The extracts showed insignificant quenching activity against DPPH radical, but they had moderate antioxidant activity (0.597 ± 0.03 to 1.342 ± 0.01) in the ferric-reducing test compared to chlorogenic acid (the reference compound) (3.618 ± 0.01). All of the extracts (ranging from 65.1 ± 0.64% to 96.3 ± 0.09%) and hispanolone (97.31 ± 0.30%) exerted a remarkable ferrous ion-chelating effect. The highest total phenol (gallic acid equivalent) and flavonoid (quercetin equivalent) contents were found in the ethyl acetate extract of B. glandulosissima (393.7 ± 3.03 and 140.6 ± 1.97 mg/g of extract, respectively). Therefore, Ballota species could be a good source of natural preservatives in foodstuffs.
Les travaux de thèse exposés dans ce manuscrit portent sur l'étude chimique de plantes du genre Psiadia. Deux axes de recherche ont été menés parallèlement. Le premier a été consacré aux criblages chimique et biologique de cinq espèces du genre Psiadia endémiques de Madagascar. Le criblage chimique avait pour objectif d’identifier les biomarqueurs de ces espèces. Il comprend, d’une part, des analyses par CCM, CLHP-UV-CAD et RMN 1H, pour l’étude du métabolome non volatil, et d’autre part, des analyses par CG-SM et CG-DIF pour l’étude des composés volatils. Le criblage biologique a permis, quant à lui, de déceler les espèces présentant des propriétés biologiques prometteuses. Les cibles biologiques choisies étaient le parasite Plasmodium falciparum, pour l’activité anti-paludique, les macrophages de souris stimulés par un composé pro-inflammatoire pour l’activité anti-inflammatoire et les lignées cellulaires cancéreuses HepG2 (cancer de foie humain) et HT 29 (cancer du côlon) pour l’activité cytotoxique. À l'issue de ce criblage, l’ensemble des extraits, riches en métabolites, a révélé un potentiel antipaludique, anti-inflammatoire et cytotoxique. Le deuxième axe de recherche a été consacré à l’étude phytochimique détaillée d’une espèce endémique de La Réunion (P. dentata) et d’une espèce endémique de Madagascar (P. lucida), sélectionnées en raison de leurs fortes activités biologiques. L'extraction, l'isolement et l'élucidation structurale de leurs métabolites ont été entrepris par différentes techniques chromatographiques (CLMP, CLHP…) et spectroscopiques (UV, IRTF, SMHR, RMN 1D et 2D). Trente-quatre métabolites spécialisés appartenant à la famille des acides hydroxycinnamiques, des polyacétylènes, des flavonoïdes, des diterpènes et des coumarines ont été isolés de ces deux plantes. Seize sont de structures nouvelles. La valorisation des molécules isolées a ensuite été envisagée via l'évaluation de leurs activités biologiques. Vingt-sept composés se sont montrés actifs contre le parasite P. falciparum (isokaempféride,3α-angéoyloxy-19,16(R)-dihydroxy-ent-labda-8(17),13-dién-15,16-olide, … ), dix ont montré une activité anti-inflammatoire et se sont révélés en même temps être non toxiques pour les cellules saines (3α-angéoyloxy-19,15(R)-dihydroxy-ent-andrograpanine, 3(R),8(R)-déhydrofalcarindiol, …) et sept ont manifesté une cytotoxicité prometteuse sur cellules HepG2 et HT 29 (11-hydroxy-3(R),8(R)-déhydrofalcarindiol, ermanine, …). Par ailleurs, une approche bio-informatique par génération de réseaux moléculaires à partir des analyses CLUHP-SM2 des fractions issues des deux espèces a permis de supposer la présence de 28 autres composés tels que le falcarinol et l’acide labdanolique, connus pour être bioactifs.
A chemical study of the hydro-ethanol extract of the leaves of Combretum glutinosum resulted in the isolation of nine compounds, including 5-demethylsinensetin (1), umuhengerin (2), (20S,24R)-ocotillone (3), lupeol (4), β-sitosterol (5), oleanolic acid (6), betulinic acid (7), corymbosin (8) and β-sitosterol glucoside (9). Four compounds have been isolated for the first time from the genus Combretum [viz. (1), (2), (3) and (8)]. The crystal structures of flavonoid (2), C20H20O8, Z′ = 2, and triterpene (3), C30H50O3, Z′ = 1, have been determined for the first time; the latter confirmed the absolute configuration of native (20S,24R)-ocotillone previously derived from the crystal structures of related derivatives. The molecules of (3) are linked into supramolecular chains by intermolecular O—H⋯O hydrogen bonds. The crude extracts obtained by aqueous decoction and hydro-ethanolic maceration, as well as the nine isolated compounds, were tested for their anthelmintic activity on the larvae and adult worms of Haemonchus contortus, a hematophage that causes parasitic disorders in small ruminants. The evaluated anthelmintic activity showed that the extracts at different doses, as well as all the compounds tested at 150 µg ml⁻¹, inhibited the migration of the larvae and the motility of the adult worms of the parasite compared with the phosphate buffer solution negative reference control. The best activity was obtained with flavonoids (1), (2) and (8) on both stages of the parasite. The flavones that showed good activity can be used for the further development of other derivatives, which could increase the anthelmintic efficacy.
Bioassays guided phytochemical investigations on the ethyl acetate-soluble fraction of the root material of Ballota pseudodictamnus (L.) Benth. led to the isolation of two new compounds, ballodiolic acid A (1) and ballodiolic acid B (2), along with three known compounds ballodiolic acid (3), ballotenic acid (4), and β-amyrin (5), which were also isolated for the first time from this species by using multiple chromatographic techniques. The structures of the compounds (1–5) were determined by modern spectroscopic analysis including 1D and 2D NMR techniques and chemical studies. In three separate experiments, the isolated compounds (1–5) demonstrated potent antioxidant scavenging activity, with IC50 values ranging from 07.22–34.10 μM in the hydroxyl radical (•OH) inhibitory activity test, 58.10–148.55 μM in the total ROS (reactive oxygen species) inhibitory activity test, and 6.23–69.01 μM in the peroxynitrite (ONOO-) scavenging activity test. With IC50 values of (07.22 ± 0.03, 58.10 ± 0.07, 6.23 ± 0.04 μM) for •OH, total ROS, and scavenge ONOO-, respectively, ballodiolic acid B (2) showed the highest scavenging ability. Antibacterial and antifungal behaviors were also exposed to the pure compounds 1–5. In contrast to compound 5 and 4, compounds 1, 2, and 3 were active against all bacterial strains studied, with a good zone of inhibition proving these as a potent antibacterial agent. Similarly, compared to compounds 3–5, compounds 2 and 1 with a 47 percent and 45 percent respective inhibition zone were found to be more active against tested fungal strains.
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.
Background: Stachys lavandulifolia Vahl is a herbaceous plant distributed in the west and south western Asia. Despite of the wide medicinal uses, there are some reports on toxicity potential of this plant. In present study we attempted to evaluate the toxicity and to characterize the cytotoxic principles of S. lavandulifolia. Methods: Brine shrimp lethality test (BSLT) was used to evaluate the general toxicity of the extracts and essential oil obtained from the aerial parts of S. lavandulifolia. Phytochemical constituents of the active extract were investigated using various chromatographic and spectroscopic methods. GC and GC-MS were also used to analyze the plant essential oil. GC and GC-MS were used to analyze the plant essential oil. Cytotoxic activities of the isolated compounds were also evaluated using MTT assay method. Results: In brine shrimp lethality test (BSLT), chloroform extract and the plant essential oil exhibited the most toxicity against Artemia salina larvae (LD50: 121.8±5.6 and 127.6±14.7 µg ml-1, respectively). GC and GC-MS analyses of essential oil led to the characterization of forty compounds of which α-bisabolol (23.85%) and thymol (17.88%) were identified as the main constituents. Nine flavonoids, Pachypodol (1), chrysosplenetin (2), kumatakenin (3), velutin (4), penduletin (5), viscosine (6), chrysoeriol (7), hydroxygenkwanin (8) and apigenin (9) were isolated from the chloroform extract of S. lavandulifolia. Among the isolated compounds, chrysosplenetin (2), a polymethoxylated flavonoid, was found as the most toxic compound toward MDA-MB-23 and HT-29 cells, with IC50 values of 88.23 and 116.50 µg ml-1, respectively. Furthermore, chrysosplenetin (2), kumatakenin (3) and viscosine (6) with selectivity indices of 2.70, 2.59 and 3.33, respectively, showed higher preferential toxicity against MDA-MB-23 cells in comparison with tamoxifen (SI:2.45). Conclusion: This study reports methoxylated flavonoids as compounds which could be involved in toxicity of S. lavandulifolia. The results of MTT assay also suggest some of these compounds as appropriate candidates for anti-cancer drug development research.
Ethnopharmacological relevance
The genus Ballota L. (Lamiaceae) comprises 33 to 35 species distributed mainly in temperate and subtropical regions of the world. Some species have been used in folk medicine as antiemetic, antispasmodic, sedative agents, vermifuge, antihemorrhoid and also in treatment of cough, etc.
Aim of this review
This review article aims to provide organized information on the available traditional uses, phytochemical and pharmacological studies of the genus Ballota, and to obtain new insights for further researches.
Materials and methods
Electronic databases, including Web of Science, Science Direct, Google Scholar, Scopus, PubMed, and Springer Link were used as information sources. General web searches were carried out using Google and Yahoo search engines by applying related search terms. Additional information was derived from books and journals in English, Latin and Persian, and also Ph.D. theses and M.Sc. dissertations.
Results
Terpenoids (particularly furanolabdane diterpenoids) and flavonoids were the main phytochemical classes identified in the extracts of Ballota species. Furanolabdane diterpenoids, e.g. ballonigrin, dehydrohispanolone, and hispanolone were reported in many species of Ballota. β-Caryophyllene, caryophyllene oxide, and germacrene D were found as the most common major compounds isolated from the essential oils of the genus Ballota. Sixty-four pharmacological studies conducted on cell lines, microorganisms, and animals were included in this review. Some species of Ballota exhibited various pharmacological activities, including promising antidepressant, anxiolytic, sedative-hypnotic, and antitussive activities in animal models. The pharmacological activities can be attributed to bioactive phytochemicals.
Conclusion
The genus Ballota is a valuable source of bioactive compounds with therapeutic potential in different diseases. Some pharmacological studies showed incomplete methodologies and ambiguous findings. Thus, the research designs of pharmacological studies based on traditional uses of Ballota species are strongly needed in cell lines and animal models. More in vitro and in vivo animal studies are required to confirm the safety, clarification of the effective doses, bioactive compounds, and the mechanisms of actions before future clinical studies.
Fungal pathogens are increasing their vicinity and able to cause serious systemic and local infection in human beings. Although there are a few antifungal drugs available in the market, most of them are not completely safe and effective. On the other hand, plants have played an important role in the history of healthcare system. Several commonly available plant species belonging to algae, bryophytes, pteridophytes, and angiosperms are used in the treatment of fungal diseases by indigenous people and managed well the outburst of fungal diseases. Plant-based antimicrobials represent a vast untapped source of medicine, and they have enormous therapeutic potential as they can serve the purpose without any side effects that are often associated with synthetic antimicrobials. The present chapter deals with the historical background and the present status of medicinal plants used in the treatment of fungal diseases.
Investigation on Ballota andreuzziana (Family Labiatae) for flavonoids led to isolation of two aglycones from ethyl acetate fraction which were identified as 7-methoxy luteolin and 6,7-dimethoxy scutellarein, in addition to three glycosides known as luteolin-7-O-glucoside, 6, 4′-dimethoxy scutellarein-7-O-glucoside and quercetin-7-O-rhamno-glucoside from butanol fraction. Antimicrobial studies revealed that, butanol extract exhibited the marked activity against M. Phlei, S. aureus and C. albicans (I.Z. =16.3, 11.3, and 10.7mm, Conc.=150mg/ml) respectively. While, chloroform extract also showed the better activity against B. subtilis (I.Z. =11.0mm, Conc.=150mg/ml). Furthermore aqueous extracts exhibited no effects at all against all tested organisms at all concentrations also, all tested Gram negative bacteria and the fungus A. niger are resistance to all concentrations of tested extracts.
Aqueous and ethanolic extracts obtained from Ballota acetabulosa (L.) Benth. (Lamiaceae) used as traditional medicine in Turkey have been investigated for their ability to inhibit 35 hospital isolates of Methicillin-resistant Staphylococcus aureus (MRSA). Both aqueous and ethanolic extracts were shown antimicrobial activity against MRSA isolates. The minimum inhibitory concentration (MIC) values of the ethanolic extract with the greatest antibacterial effect were those of the plant MIC 0.4-1.6 μg/mL and MBC 3.2-12.5 μg/mL, respectively.
The ethanol extracts obtained from Ballota nigra subsp. anatolica P.H. Davis (Lamiaceae) were investigated for their antimicrobial activities. The antimicrobial activity of the extract was tested against Bacillus subtilis ATCC 6633, Bacillus cereus ATCC 7064, Staphylococcus aureus ATCC 6538P, Escherichia coli ATCC 10538, Proteus vulgaris ATCC 6899, Salmonella typhimurium CCM 5445 and Pseudomonas aeruginosa ATCC 27853, Candida albicans ATCC 10239, Debaryomyces hansenii DSM 70238, Kluyveromyces fragilis ATCC 8608 and Rhodotorula rubra DSM 70403 by disk diffusion method and microdilution method. Some antibacterial and antifungal antibiotics were used as a positive reference standard to determine the sensitivity of the strains. The extracts showed strong antibacterial activity against Escherichia coli, with inhibition zones of 13.0 mm and with minimum inhibitory concentrations (MIC's) and minimum bactericidal concentrations (MBC's) of 250 (500) mu g/mL, respectively. The extracts also exhibited moderate activity against the other test microorganisms. The results demonstrate that the ethanol extract of B. nigra subsp. anatolica has significant activity and suggest that it may be useful in the treatment of infections.
Ballota species have been used in Turkish folk medicine for treatment of wounds and burns, suppression cough and upper respiratory inflammation. According to the previous phytochemical investigations terpenoids, flavonoids, phenylpropanoids, essential oils, tannins, and saponins were isolated from Ballota species. The aim of the present research is to evaluate total orthodihydroxycinnamic acid derivatives (TCC) and total flavonoid content (TFC) of Ballota species by spectrophotometrically according to European Pharmacopoeia. The results of this study show that; Ballota species have distinct phenolic contents. Ballota nigra subsp. anatolica extract contained the highest amount of ortho-dihydroxycinnamic acid derivatives, while highest proportion of flavonoids was found in Ballota glandulosissima. On the other hand, Ballota nigra subsp. foetida extract contained the lowest amount of ortho-dihydroxycinnamic acid derivatives, while lowest proportion of flavonoids was found in Ballota rotundifolia.
Ballota L. comprises several relevant species largely used for their excellent therapeutic properties. Ballota hispanica (L.) Benth. is widely used in herbal medicine, and it is sold in herbalist shops for its sedative and antispasmodic properties. Considering its traditional medicinal use and the lack of scientific studies on the volatile components of this species as well as on its biological activities, in this study the chemical composition of the essential oil from aerial parts of B. hispanica, collected in Sicily, was evaluated by gas chromatography and gas chromatography-mass spectrometry. α-Elemol was the most abundant component of the oil (10.9%), followed by α-ylangene (8.5%), γ-dodecalactone (5.1%), and manoyl oxide (4.8%). A comparison was made of the composition of the different Ballota taxa studied so far showing a peculiar profile of B. hispanica. Futhermore, the antimicrobial and the free radical scavenging activities of the oil were determined.
In the present study, the antioxidant properties of ethanol extracts of 16 Ballota species belonging to the Lamiaceae family and growing in Turkey on superoxide anion formation and lipid peroxidation were investigated. All extracts inhibited superoxide anion formation but to different extents. The extracts of Ballota antalyense, Ballota macrodonta, Ballota glandulosissima, Ballota larendana, Ballota pseudodictamnus, Ballota nigra subsp. anatolica, Ballota saxatilis subsp. saxatilis, Ballota rotundifolia, and Ballota saxatilis subsp. brachyodonta exhibited remarkable anti-superoxide anion formation with IC50 values from 0.50 to 0.87 mg/ml. The extracts of Ballota antalyense, Ballota macrodonta and Ballota glandulosissima have the lowest IC50 values (0.50, 0.51 and 0.51 mg/ml, respectively) which were rather close to the well-known superoxide anion scavenger α-tocopherol (IC50: 0.22 mg/ml). The extracts of Ballota inaequidens, Ballota glandulosissima, Ballota saxatilis subsp. saxatilis, Ballota macrodonta and Ballota antalyense inhibited lipid peroxidation with IC50 values from 12 to 20 mg/ml. The extracts of Ballota inaequidens (IC50: 12 mg/ml) and Ballota glandulosissima (IC50: 15 mg/ml) exhibited the strongest inhibitory effects on lipid peroxidation compared with α-tocopherol (IC50: 3 mg/ml). The results show that Ballota glandulosissima is the best antioxidant source among these 16 Ballota species.
We aimed to investigate antinociceptive activity and median lethal dose (LD50) of water extract of Ballota glandulosissima Hub.-Mor&Patzak in mice. In this study, water extract of Ballota glandulosissima was investigated for antinociceptive activity using acetic acid-induced "writhing" and "tail-flick" tests. Acetyl salicylic acid and morphine were used as the reference drug. Mice were injected Ballota glandulosissima extract intraperitoneally in doses of 100 mg/kg and 200 mg/kg, respectively. The extract of Ballota glandulosissima caused dose related inhibition in the acetic acid-induced ab dominal stretching response in mice. The extract of Ballota glandulosissima also showed significant changes in the nociceptive threshold of the tail-flick test. The motor coordination of mice treated with the water extract was evaluated by using the "rotarod" test and was found to be not impaired in comparison with that of control mice.The results obtained in the present study indicate that the water extract of Ballota glandulosissima has promising antinociceptive activity. The LD50 of Ballota glandulosissima was determined as 8.885 g/kg.
This review deals with the description of bioactive secondary metabolites produced by the living organisms, including plants, fungi, bacteria (actinomycetes and cyanobacteria) and lichens which have activity against the mosquito Aedes aegypti, the vector responsible for dengue and yellow fever. The insecticidal activities of these compounds are discussed herein, and their mode of action and structure–activity relationships are presented when appropriate. Control agents (fungi, bacteria, and other organisms) are briefly commented since they can also be a rich source of bioactive compounds. It describes 319 compounds from plants, 25 from fungi, 27 from bacteria (including actinomycetes and cyanobacteria), and 7 from lichen and cites 264 references. Covering: up to February 2011.
The water extract of Ballota inaequidens. Hub.-Mor. & Patzak (Lamiaceae) was investigated for antinociceptive and anti-inflammatory activities in mice and rats. The tail-flick test, acetic acid–induced writhing test, and the carrageenan-induced rat paw edema test were used to determine these effects. Our findings show that Ballota inaequidens. caused dose-related inhibition in the acetic acid–induced abdominal stretching in mice. The medium effective dose (ED50) value of Ballota inaequidens. was found to be 85.38 mg/kg. Ballota inaequidens. showed no significant changes in the nociceptive threshold of the tail-flick test but did show an inhibition of paw edema induced by carrageenan. The ED50 value of Ballota inaequidens. was found to be 99.42 mg/kg. The current study reveals that the water extract of Ballota inaequidens. possesses promising antinociceptive and anti-inflammatory activities.
Five flavonoids, (2S,3S)-dihyrokaempferol 3-O-β-d-glucoside (1) and its isomer (2R,3R)-dihydrokaempferol 3-O-β-d-glucoside (2) , isovitexin (3), velutin (4) and 5,4′-dihydroxy-7,3′,5′-trimethoxyflavone (5), were isolated from acai (Euterpe oleracea Mart.) pulp. The structures of these compounds were elucidated based upon spectroscopic and chemical analyses. To our knowledge, compounds 1, 2, 4 and 5 were identified from acai pulp for the first time. The in vitro antioxidant activities of these compounds were evaluated by the oxygen radial absorbance capacity (ORAC) assay. The ORAC values varied distinctly (4458.0–22404.5 μmol Trolox equivalent (TE)/g) from 5,4′-dihydroxy-7,3′,5′-trimethoxyflavone (5) to isovitexin (3) and were affected by the numbers/positions of hydroxyl groups, substitute groups, as well as stereo configuration. The anti-inflammatory effects of these compounds were screened by the secreted embryonic alkaline phosphatase (SEAP) reporter assay, which is designed to measure NF-κB activation. Velutin (4) was found to dose-dependently inhibit SEAP secretion in RAW-blue cells induced by LPS, with an IC50 value of 2.0 μM. Velutin (4) also inhibited SEAP secretion induced by oxidised LDL, indicating potential athero-protective effects.Highlights► Five flavonoids were isolated from acai pulp; four of them were identified from this plant for the first time. ► Antioxidant activities of the five flavonoids were assessed by ORAC. ► Anti-inflammatory effects of these five flavonoids were evaluated by SEAP assay, which was designed to measure NF-κB activation. ► The uncommon flavone velutin was found to be a strong NF-κB inhibitor.
The objective of this study was to determine the antibacterial effect of all Ballota species growing in Turkey on four strains of Listeria. Ethanol extracts of sixteen Ballota species were tested against 4 different Listeria isolates (Listeria monocytogenes, L. ivanovii, L. innocua, L. murrayi) by the agar diffusion method. All plants showed higher antilisterial activity against L. monocytogenes. The extracts of B. nigra subsp. anatolica, B. cristata, B. nigra subsp. foetida, B. rotundifolia, B. nigra subsp. uncinata, B. pseudodictamnus subsp. lycia and B. saxatilis subsp. saxatilis have highest antilisterial activity against L. monocytogenes. Among these species B. nigra subsp. anatolica, B. cristata and B. nigra subsp. foetida have also antilisterial activity against L.ivanovii, L. innocua and L. murrayi.
In the present study, the antioxidant properties of ethanol extracts of 16 Ballota species belonging to the Lamiaceae family and growing in Turkey on superoxide anion formation and lipid peroxidation were investigated. All extracts inhibited superoxide anion formation but to different extents. The extracts of Ballota antalyense, Ballota macrodonta, Ballota glandulosissima, Ballota larendana, Ballota pseudodictamnus, Ballota nigra subsp. anatolica, Ballota saxatilis subsp. saxatilis, Ballota rotundifolia, and Ballota saxatilis subsp. brachyodonta exhibited remarkable anti-superoxide anion formation with IC(50) values from 0.50 to 0.87 mg/ml. The extracts of Ballota antalyense, Ballota macrodonta and Ballota glandulosissima have the lowest IC(50) values (0.50, 0.51 and 0.51 mg/ml, respectively) which were rather close to the well-known superoxide anion scavenger alpha-tocopherol (IC(50): 0.22 mg/ml). The extracts of Ballota inaequidens, Ballota glandulosissima, Ballota saxatilis subsp. saxatilis, Ballota macrodonta and Ballota antalyense inhibited lipid peroxidation with IC(50) values from 12 to 20 mg/ml. The extracts of Ballota inaequidens (IC(50): 12 mg/ml) and Ballota glandulosissima (IC(50): 15 mg/ml) exhibited the strongest inhibitory effects on lipid peroxidation compared with alpha-tocopherol (IC(50): 3 mg/ml). The results show that Ballota glandulosissima is the best antioxidant source among these 16 Ballota species.
A bioactivity-guided chemical study of aerial parts of Croton ciliatoglanduliferus Ort. led to the isolation for the first time of the flavonoids retusin (5-hydroxy-3,7,3',4'-tetramethoxyflavone) (1) and pachypodol (5,4'-dihydroxy-3,7,3'-trimethoxyflavone) (2) from the n-hexane extract. Compounds 1 and 2 were separated by preparative thin-layer chromatography. Compound 2 was the most active compound on ATP synthesis inhibition. The I50 value was 51 microM. Pachypodol behaves as a Hill reaction inhibitor. It inhibited the uncoupled electron flow on photosystem II partial reaction from water to dichlorophenol indophenol (DCPIP) and from water to sodium silicomolybdate. However, the uncoupled partial reaction from diphenylcarbazide to DCPIP and the uncoupled photosystem I from DCPIPred to MV were not inhibited by 2. These results were corroborated by fluorescence decay data. Therefore, pachypodol inhibits the water-splitting enzyme activity. Compound 1 with a 4'-methoxy group was a weak inhibitor, indicating that the 4' free -OH group is important for strong inhibition.
Calycopteris floribunda Lam., commonly known as 'goichia lata or goache lata', is a large climbing woody shrub from Bangladesh, and well distributed in a number of other south-east Asian countries. Traditionally, C. floribunda has been used in colic, as an antihelminthic, astringent and carminative, and for the treatment of diarrhoea, dysentery, jaundice and malaria in many countries including Bangladesh. Pachypodol (5,4'-dihydroxy-3,7,3'-trimethoxyflavone) has been isolated from the leaves of C. floribunda by repeated column chromatography on silica gel, and the structure confirmed by spectroscopic means. While the general toxicity of pachypodol was determined by the brine shrimp lethality assay, the cytotoxic potential of this flavonoid has been evaluated by the Promega's CellTiter 96 Non-Radioactive Cell Proliferation Assay using the CaCo-2 colon cancer cell line (IC(50) = 185.6 microM). A summary of the biological activities of pachypodol reported to date is also presented.
From the aerial parts of Ballota saxatilis subsp. saxatilis, the three flavone aglycones 6 hydroxy apigenol 7,4'-dimethyl ether (ladanein) (1), kaempferol 3,7,4'-trimethyl ether (2), and quercetin 3,7,3',4'-tetramethyl ether (retusin) (3), have been isolated and identified.
Two flavonols in Euodia glabra have been characterized as 3,7,3′-trimethylquercetin (I) and 7-isopentenyl-3,3′-dimethylquercetin (II).
Nine of eleven methylated flavonols isolated from Larrea cuneifolia Cav. collected in Argentina have been fully characterized. UV, MS and NMR spectral data are presented for the nine substances all of which were identified as methyl ethers of quercetin and kaempferol. Two of the compounds, 7,3′,4′-trimethylquercetin (II) and 3,7,3′-trimethylquercetin (III), are new natural products. The others are 3,7,3′,4′-tetramethylquercetin (I) (retusine), 3,7-dimethylkaempferol (IV), 7,3′-dimethylquercetin (V) (rhamnazin), 3,7-dimethylquercetin (VI) (kumatakenin), 3,3′-dimethylquercetin (VII), 3-methylkaempferol (VIII) and 3′-methylquercetin (IX) (isorhamnetin). Nordihydroguaiaretic acid (XII) was also detected.
5-Hydroxy-7-methoxyflavanone, 5,7-dimethoxyflavanone, 5-hydroxy-7-methoxyflavone 5-hydroxy-7,4′-dimethoxyflavone, 5,7-dimethoxyfiavone, 5,7,4′-trimethoxyflavone, 5,7,3′,4′-tetramethoxyflavone, 5-hydroxy-3,7-dimethoxyflavone, 5-hydroxy-3,7,4′-trimethoxyflavone, 3,5,7-trimethoxyflavone and 5-hydroxy-3,7,3′,4′-tetramethoxyflavone have been isolated from the black rhizomes of Boesenbergia pandurata.
(+)-Abscisic acid was isolated as the methyl ester from Pinus densiflora pollen and identified spectroscopically.
Hispanolone was isolated from Ballota andreuzziana; B. pseudodictamnus contains ballonigrin, 18-hydroxyballonigrin, marrubenol, and the flavone 7, 4′-di-O-methylapigenin.
From the acetone extract of B. hispanica hispanonic acid (1a, C20H24O4) was isolated; CH2N2 treatment of other chromatographic fractions and extended purification yielded methyl hispanonate 1b and methyl hispaninate 6b (Chemical Equation Presented) (C21H26O4). Both products have an unusual seven-membered ring C. DDQ aromatization and catalytic hydrogenation of 1b are described; 6b gave a crystalline peroxide, confirming the proposed structures. Correlation of 1b and 6b was achieved through reduction products.
From a dichloromethane extract and a hydrolysed methanolic extract from the leaves of Psiadia trinervia, 13 3-methylated flavonols have been isolated. Their structures were established by the usual spectroscopic methods (UV, EIMS, 1H and 13C NMR). Ayanin, casticin, chrysosplenol-D and 5,7,4′-trihydroxy-3,8-dimethoxyfiavone were responsible for the antifungal activity found in the preliminary screening. Chrysosplenol-D, isokaempferide, 5,7,4′- trihydroxy-3,3′-dimethoxyflavone and 5,7,4′-trihydroxy-3,8-dimethoxyflavone displayed antibacterial activity. Twenty-nine derivatives were prepared by permethylation and selective methylation of the free hydroxyl group at C-5. The antimicrobial activities of the isolates and derivatives were determined by bioautographic assays using C. cucumerinum and B. cereus as test organisms.
Four sesquiterpene lactones and three other compounds have been isolated from the EtOH-H2O-soluble fraction of a CHCl3 extract of Centaurea ornata. A new grosshemin derivative 3 is described, and the stereochemistry of natural 11-epi-dihydroreynosin [2] is revised.
A minor glucoside, corymbosin, has been isolated from Turbina corymbosa and the structure and partial stereochemistry of its aglucone, corymbositin, established.
National Committee for Clinical Laboratory Standards. Performance standards for antimicrobial disc subceptibility tests. XI. Informational supplement M100 Two new unusual diterpenoids from Ballota hispanica
- Sii
- Wayne Nccls
- B Rodriguez
- G Savona
- Piozzi
NeCLS (2001): National Committee for Clinical Laboratory Standards. Performance standards for antimicrobial disc subceptibility tests. XI. Informational supplement M100-SII, NCCLS, Wayne. Rodriguez B, Savona G, Piozzi F (1979): Two new unusual diterpenoids from Ballota hispanica. J Org Chem 44: 2219-2221.
Tangeretin from Ballota nigra
- W Kisiel
- W Piozzi
Kisiel W,Piozzi W (1995): Tangeretin from Ballota nigra. Polish J Chem 69: 476-477.
UV A max (MeOH) 335, 270; (+NaOMe) 370, 287; (+AIC1 3 ) 358, 278; (+AICliHCl) 352, 279; (+NaOAc) 336, 270
- Nakanishi
Hydroxy-7,3',4'-trimethoxyflavone (3) Yellow needles (65mg), m.p. 156-158°C (lit. 163-165°C) (Nakanishi et al., 1985). UV A max (MeOH) 335, 270; (+NaOMe) 370, 287; (+AIC1 3 ) 358, 278; (+AICliHCl) 352, 279; (+NaOAc) 336, 270; (+NaOAc/H 3B03 ) 335, 270; IH_ NMR (CDC1 3 ) 8 3.82 (3H, S, OCR 3 ), 3.85 (3H, s, OCH 3 ), 3.89 (3H, s, OCH 3 ), 6.29 [lH, d (J = 2Hz) H-6], 6.41 [lH, d (J =2Hz) H-8], 6.50 [lH, s, H-3], 6.91 [lH, d (J = 8.5Hz),
UV A max (MeOH) 346, 250; (+NaOMe) 398, 346, 260; (+AIC1 3 ) 389, 274; (+AICliHCI) 383, 276; (+NaOAc) 349, 253
- Velutindas
Velutin (5,4'-dihydroxy-7,3'-dimethoxyflavone) (4) Yellow needles (20 mg), m.p. 216-218°C (lit. 225-227°C) (Das et al., 1970). UV A max (MeOH) 346, 250; (+NaOMe) 398, 346, 260; (+AIC1 3 ) 389, 274; (+AICliHCI) 383, 276; (+NaOAc) 349, 253; (+NaOAc/H 3B03 ) 346, 250; IH-NMR (CDCb) 83.81 (3H, s, OCH 3 ), 3.93 (3H, s, OCH 3 ), 6.30 [IH, d (J = 2Hz) H-6], 6.42 (lH, s, H-3), 6.51 [IH, (d, J = 2Hz) H-8], 6.97 [IH, d (J = 8.5),
UV A max (MeOH) 350, 268; (+NaOMe) 364, 281; (+AICb) 405, 268; (+AICliHCI) 405, 269, 256; (+NaOAc) 350, 268
- Retusinjaipetch
Retusin (5-hydroxy-3,7,3',4'-tetramethoxyftavone) (6) Yellow needles (15mg), m.p. 147-148°C (lit. 160-162°C) (Jaipetch et al., 1983). UV A max (MeOH) 350, 268; (+NaOMe) 364, 281; (+AICb) 405, 268; (+AICliHCI) 405, 269, 256; (+NaOAc) 350, 268; (+NaOAc/H 3B03 ) 350, 268, 431; IH-NMR (CDCb) 8 3.79 (3H, s, OCH 3 ), 3.80 (3H, S, OCH 3 ), 3.89 (3H, S, OCH 3 ), 3.90 (3H, s, OCH 3 ), 6.28 [2H, d (J =2.5Hz) H-6], 6.37 [2H, (d, J =2.5 Hz) H-8], 6.91 [2H, d (J = 8.5),
Yellow needles (15mg), m.p UV A m ax (MeOH) 330, 276; (+NaOMe) 335,295; (+AIC1 3 ) 361, 301; (+AICliHCI) 352, 300; (+NaOAc) 330, 276
- Salvigenin
Salvigenin (5-hydroxy-6,7,4'-trimethoxyflavone) (5) Yellow needles (15mg), m.p. 191-192°C (lit. 190-193°C) (Sezik & Ezer, 1984). UV A m ax (MeOH) 330, 276; (+NaOMe) 335,295; (+AIC1 3 ) 361, 301; (+AICliHCI) 352, 300; (+NaOAc) 330, 276; (+NaOAc/H 3B03 ) 330, 276;
UV A max (MeOH) 356, 254; (+NaOMe) 404, 356, 263; (+AICI 3 ) 402, 369, 267; (+AICh/HCI) 398, 356, 266; (+NaOAc) 358, 255
- Fraser
- Lewis
Fraser & Lewis, 1973). UV A max (MeOH) 356, 254; (+NaOMe) 404, 356, 263; (+AICI 3 ) 402, 369, 267; (+AICh/HCI) 398, 356, 266; (+NaOAc) 358, 255; (+NaOAc/H 3B03 ) 356, 254; IH-NMR (CDCb);
Phytochemical investigations on the plants used as folk medicine and herbal tea in Turkey
- E Sezik
- N Ezer
Sezik E, Ezer N (1984): Phytochemical investigations on the plants used as folk medicine and herbal tea in Turkey. Acta Pharmaceutica Turcica 26: 4-9.
4',5'-tetramethoxyflavone) (7) Yellow needles (481ng), m.p. 187-188°C. UV A max (MeOH) 327-271; (+NaOMe) 370, 281
- Corymbosin
Corymbosin (5-hydroxy-7,3',4',5'-tetramethoxyflavone) (7) Yellow needles (481ng), m.p. 187-188°C. UV A max (MeOH) 327-271; (+NaOMe) 370, 281; (+AICb) 344, 274;
They included the Gram-positive bacteria Streptococcus faecalis Bacillus subtilis (ATCC 6633) and Pharmaceutical Biology Downloaded from informahealthcare Antibacterial activities of diterpenoids isolated from Ballota saxatilis subsp. saxatilis
- M Tanker
- B Sever
- Anton J R Englert
- Altanlar
Antimicrobial activity Bacterial strains were obtained from the Refik Saydam Hygiene Center. They included the Gram-positive bacteria Streptococcus faecalis (ATCC 19433), Staphylococcus aureus (ATCC 25923), Bacillus subtilis (ATCC 6633) and Pharmaceutical Biology Downloaded from informahealthcare.com by Lakehead University on 03/13/13 For personal use only. References Citoglu G, Tanker M, Sever B, Englert J, Anton R, Altanlar N (1998): Antibacterial activities of diterpenoids isolated from Ballota saxatilis subsp. saxatilis. Planta Med 64: 484-485.
Antimicrobial flavonoids from Psiadia trinervia and their methylated and acetylated derivatives
- U Wang
- M Hamburger
- J Guedo
- K Hostetman