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Sugar Containing Compounds and Biological Activities of Lagochilus Setulosus

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Sugar Containing Compounds and Biological Activities of Lagochilus Setulosus molecules Communication Sugar Containing Compounds and Biological Activities of Lagochilus setulosus Davlat Kh. Akramov 1, Nilufar Z. Mamadalieva 1,2,* , Andrea Porzel 2, Hidayat Hussain 2 , Mthandazo Dube 2 , Akbar Akhmedov 3, Ahmed E. Altyar 4 , Mohamed L. Ashour 5,6,* and Ludger A. Wessjohann 2 1 Institute of the Chemistry of Plant Substances, Uzbekistan Academy of Sciences, M. Ulugbek Str 77, Tashkent 100170, Uzbekistan; [email protected] 2 Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle, Germany; [email protected] (A.P.); [email protected] (H.H.); [email protected] (M.D.); [email protected] (L.A.W.) 3 Department of Botany and Plant Physiology, Samarkand State University, University Blv. 15, Samarkand 140104, Uzbekistan; [email protected] 4 Department of Pharmacy Practice, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia; [email protected] 5 Department of Pharmaceutical Sciences, Pharmacy Program, Batterjee Medical College, Jeddah 21442, Saudi Arabia 6 Department of Pharmacognosy, Faculty of Pharmacy, Ain Shams University, Cairo 11566, Egypt * Correspondence: [email protected] (N.Z.M.); [email protected] (M.L.A.) Abstract: Phytochemical investigation of the methanolic extract obtained from the aerial parts of Citation: Akramov, D.K..; Lagochilus setulosus (Lamiaceae) afforded the new compound 1-methoxy-3-O-b-glucopyranosyl-α-L- Mamadalieva, N.Z.; Porzel, A.; oliose (1) together with five known glycosides, namely sitosterol-3-O-b-glucoside (2), stigmasterol-3- Hussain, H.; Dube, M.; Akhmedov, O-b-glucoside (3), pinitol (4), 6b-hydroxyl-7-epi-loganin (5), and chlorotuberoside (6). The structures A.; Altyar, A.E.; Ashour, M.L.; of these compounds were elucidated by extensive spectroscopic analyses, especially HR-MS, 1D Wessjohann, L.A. Sugar Containing and 2D NMR spectroscopy. The in vitro cytotoxic activity of the methanolic extract and the isolated Compounds and Biological Activities of Lagochilus setulosus. Molecules 2021, compounds was assessed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) 26, 1755. https://doi.org/10.3390/ and crystal violet (CV) staining assays. In addition, the antifungal activities of the components molecules26061755 were evaluated against Botrytis cinerea, Septoria tritici, and Phytophthora infestans. The anthelmintic potential was determined against Caenorhabditis elegans nematodes. Neither the extract nor the Academic Editors: isolated compounds showed promising activity in all the bioassays. Alessandra Morana and Giuseppe Squillaci Keywords: Lamiaceae; Lagochilus setulosus; 1-Methoxy-3-O-b-glucopyranosyl-a-L-oliose; NMR; HR-MS; anthelmintic; antifungal; cytotoxic Received: 4 March 2021 Accepted: 19 March 2021 Published: 21 March 2021 1. Introduction Publisher’s Note: MDPI stays neutral Lagochilus with regard to jurisdictional claims in The genus (Lamiaceae) is native to central, south-central, and eastern Asia. published maps and institutional affil- It consists of 46 species with 18 of them growing in Uzbekistan. Taxa of the genus Lagochilus iations. basically occur throughout the territory of Uzbekistan, starting from the deserts to Tian- Shan and Pamir-Alay mountain systems. The majority of species can be found in the Pamir-Alai Mountain, southwest of Tian-Shan and Turanian lowland. Species from the genus Lagochilus belong to the most vulnerable plant species from the Lamiaceae family [1], with a decoction of herb and roots of Lagochilus species used in folk medicine mainly Copyright: © 2021 by the authors. as styptics, hemostatics, and tranquilizers, and also for skin conditions, stomach pain, Licensee MDPI, Basel, Switzerland. hemorrhages, and inflammation. Previous phytochemical investigations on Lagochilus This article is an open access article distributed under the terms and species revealed the presence of essential oils, flavonoids, polysaccharides, sterols, iridoids, conditions of the Creative Commons terpenoids, and more frequently diterpenes, which are considered as chemical markers Attribution (CC BY) license (https:// for this genus. About 150 metabolites have been reported from all previous classes in the creativecommons.org/licenses/by/ genus [2–4]. 4.0/). Molecules 2021, 26, 1755. https://doi.org/10.3390/molecules26061755 https://www.mdpi.com/journal/molecules Molecules 2021, 26, x FOR PEER REVIEW 2 of 7 Molecules 2021, 26, 1755 2 of 7 The species of Lagochilus setulosus Vved. is endemic of the southwestern area of Tian- Shan,The and species it can be of foundLagochilus distributed setulosus inVved. low mountains is endemic between of the southwestern the border of area the regions of Tian- ChimkentShan, and it(Kazakhstan) can be found and distributed Tashkent in (Uzbekistan) low mountains [1]. between A literature the border survey of reveals the regions that thereChimkent are no (Kazakhstan) reports on traditional and Tashkent use, biolog (Uzbekistan)ical activity, [1].A or literature chemical surveyinvestigations reveals of that L. setulosusthere are, noexcept reports our onprevious traditional report use, on biological the volatile activity, components or chemical of the investigations aerial parts ofandL. theirsetulosus antioxidant, except our and previous enzyme report inhibitory on the activi volatileties components[5]. In continua of thetion aerial of our parts phytochem- and their icalantioxidant studies on and L. enzymesetulosus, inhibitory herein, we activities report the [5 isolation]. In continuation and structure of our identification phytochemical of a newstudies disaccharide on L. setulosus 1-methoxy-3-, herein, weO- reportβ-glucopyranosyl- the isolationα and-L-oliose structure (1) (Figure identification 1) together of a with new twodisaccharide known sterol 1-methoxy-3- glucosides:O-b-glucopyranosyl- sitosterol-3-O-β-glucosideα-L-oliose ((daucosterol)1) (Figure1) together (2) and withstigmas- two terol-3-knownO sterol-β-glucoside glucosides: (3), sitosterol-3-as well as Ocyclitol–pinitol-b-glucoside (daucosterol) [3-(O-methyl- (2D)-chiro-inositol)] and stigmasterol-3- (4), andO-b -glucosidethe two iridoid (3), as glycosides well as cyclitol–pinitol 6β-hydroxyl-7- [3-(epiO-loganin-methyl- D(5-chiro-inositol)]) and chlorotuberoside (4), and the(6) (Figuretwo iridoid 1). In glycosides addition, 6 theb-hydroxyl-7- anthelmintic,epi-loganin antifungal, (5) and and chlorotuberoside cytotoxic effects (6 of) (Figure the isolated1). In compoundsaddition, the 1, anthelmintic, 4, a mixture antifungal,of 5 and 6, and the cytotoxic methanolic effects extract of the isolatedof L. setulosus compounds have been1, 4, evaluated.a mixture of 5 and 6, and the methanolic extract of L. setulosus have been evaluated. Figure 1. ChemicalChemical structures of the isolated compounds from the aerial parts of L. setulosus. 2. Results Results and and Discussion Discussion 2.1. Chemical Chemical Composition Composition of of L. L. setulosus Since no publications were found regarding the chemical composition of the aerial parts ofof L.L. setulosus setulosus, this, this is theis the first first report report on theon occurrencethe occurrence of sugar-containing of sugar-containing compounds com- pounds1–6. The 1–6 chromatographic. The chromatographic fractionation fractionation of the methanolic of the methanolic extract of extract this species of this afforded species affordedsitosterol-3- sitosterol-3-O-b-D-glucosideO-β-D-glucoside (2) and stigmasterol-3- (2) and stigmasterol-3-O-b-D-glucosideO-β-D-glucoside (3) as an ( inseparable3) as an in- separablemixture (with mixture a ratio (with of a 1:1), ratio and of 1:1), the new and compoundthe new compound1. The chemical 1. The chemical structure structure of com- ofpounds compounds2 and 3 2was and determined 3 was determined based on based spectral on spectral analysis analysis and comparisons and comparisons with relevant with relevantliterature literature [6]. These [6]. compounds These compounds were also were found also in other foundLagochilus in other speciesLagochilus viz. speciesL. inebrians viz. L.and inebriansL. gypsaceus and L.[7 ].gypsaceus Further investigations[7]. Further investigations of the methanolic of the extract methanolic of L. setulosus extract ofafforded L. set- ulosuspinitol afforded (4) and anpinitol inseparable (4) and an mixture inseparable (with mixture a ratio of (with 1.2:1) a ofratio 6b -hydroxyl-7-of 1.2:1) of 6βepi-hydroxyl--loganin 7-(5epi) and-loganin chlorotuberoside (5) and chlorotuberoside (6). Most recently, (6). Most the recently, iridoid the glycoside iridoid 5glycosidehas been 5 reportedhas been reportedfrom several from species several of speciesEremostachys of Eremostachys[8,9] and [8,9]Picconia and Picconia excelsa [ 10excelsa]. Chlorotuberoside [10]. Chlorotuber- (6) osidewas previously (6) was previously isolated fromisolated different from different genera of genera Lamiaceae, of Lamiaceae, such as Phlomissuch as Phlomis[11–13], [11–Ere- mostachys [14], Lamiophlomis [15], which are taxonomically close to Lagochilus. Pinitol (4) is a cyclitol [16] and has been detected in gymnosperm (Pinus, Abies) and angiosperm Molecules 2021, 26, x FOR PEER REVIEW 3 of 7 Molecules 2021, 26, 1755 3 of 7 13], Eremostachys [14], Lamiophlomis [15], which are taxonomically close to Lagochilus. Pin- itol (4) is a cyclitol [16] and has been detected in gymnosperm (Pinus, Abies) and angio- sperm (Fabaceae, Nyctaginaceae, Asteraceae, Zygophyllaceae, Caryophyllaceae,
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