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Isolation of Aryl Naphthalene's from Cleistanthus Collinus by Column

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Isolation of Aryl Naphthalene's from Cleistanthus Collinus by Column Available online at www.scholarsresearchlibrary.com Scholars Research Library Der Pharmacia Lettre, 2018, 10 [2]: 93-97 [http://scholarsresearchlibrary.com/archive.html] ISSN 0975-5071 USA CODEN: DPLEB4 Isolation of Aryl Naphthalene’s from Cleistanthus Collinus by Column Chromatography Rajdip Utanea*, SujataDeob 1Department of Chemistry, Sant Gadge Maharaj Mahavidyalaya, Hingna. affiliated to RTMNU, Nagpur (M.S.), India-441110 2Department of Chemistry, Govt. Institute of Science, affiliated to RTMNU, Nagpur (MS), India-440001 *Corresponding author: Rajdip U, Department of Chemistry, Sant Gadge Maharaj Mahavidyalaya, Hingna. affiliated to RTMNU, Nagpur (M.S.), India. Email-id: [email protected] ABSTRACT Aryl naphthalene’s lignans are extracted by pet. ether from Cleistanthus collinus . The bark, leaves, heartwood, fruits and other parts of this plant are rich in lignans cleistanone along with their lactones. Isolation of chemical constitutions by column chromatography, followed by TLC examination and Detection in iodine chamber with UV lamp or sprayer solution (CH2Cl2: CH3OH). The isolated arylnaphthalide lignans are cleistanone, diphyllin, cleistanthins A, C and D and 4-O-(30-O-methyl-b -D- glucopyranosyl)-diphyl lin. Key words: Cleistanthus Collinus, column chromatography, cleistanone, diphyllin, cleistanthins. INTRODUCTION Cleistanthus collinus is a highly poisonous plant. In Botanical Description Cleistanthus collinus is a plant species first described by Roxburgh, with its current name after Bentham and Hooker. It is included in the family Phyllanthaceae, the IUCN categorizes this species as vulnerable. Sex distribution: Cleistanthus collinus is monoecious with unisexual (male or female) flowers on the same individual. Mode of pollination: It is pollinated by wide variety of insects Seed dispersal: mechanical dispersal: barochory (dispersal of seeds by gravity), self-propagation. The ripe and dry capsule of cleistanthins collinus opens to scatter the seeds To explore the possibilities of using homoeopathic drugs to develop desired medicinal properties in medicinal trees used in traditional healing with the help of traditional healers on Indian state chhattisgarh the selected drugs were applied on Cleistanthus collinus. After different durations desired plant parts were collected by the traditional healers. They tested its medicinal properties through traditional methods and medicinally rich parts were used in traditional healing. Healers suggested the use of homoeopathic drugs with traditional allelopathic solutions 93 Scholar Research Library Rajdip U, et al. Der Pharmacia Lettre, 2018, 10 [2]:93-97 ______________________________________________________________________________ Its etheric extract has been reported to show neuro activity. The antimicrobial properties of Cleistanthus collinus leaf extract against the pathogens like Methicillin Resistant Staphylococcus aureus (MRSA). Antioxidant assay was also performed with the plant extract. The results reveal positive medicinal properties of the plant leaves against skin infection, Antimicrobial assay and Antioxidant assay In present study the hemical constitutions are extraction, isolates followed by TLC and detection in iodine chmber with UV lamp. The isolated arylnaphthalide lignan, cleistanone, diphyllin cleistanthins A, C and D and 4-O-(30-O-methyl-b -D-glucopyranosyl)- diphyllin. Materials and Methods Cleistanthus collinus plant leaves were collected from region of Maharashtra, India. The selected region was a field of a small town named isapur, post- pipla (D.B.) which is situated near koradi in Nagpur district, vidarbha (Maharashtra), India on 15 March 2017 in morning at 8.00 AM and author authenticated from Department of Botany, Rastrasant Tuukadoji Maharaj Nagpur University Nagpur (MH), India where a voucher specimen is 10057 preserved. Column chromatography was performed over silica gel (BDH 100—300 mesh) and TLC with silica gel 60 GF254 from merk millipore . The spots were detected in an iodine chamber and under UV lamp. The spots were also visualized by spraying the plates with 10% methanol in sulphuric acid and subsequently heating on a hot plate. Extraction Extraction of compounds by using sox let extraction method. Solvent used with respective polarity, and their optimization. In optimization of various solvent for extraction compounds in which petroleum ether shows 19.7 %. Quantification of solvent volume is an effective at 15 ml and determination of effective time for extraction is 6 hours. Isolation of aryl naphthalene by Column chromatograms Air dried and finally milled whole shade dried plant materials (3 Kg) of Cleistanthus collinus were exhaustively extracted with petroleum ether (60-800C in a soxhlet apparatus for 120 hrs. The total extract was concentrated under reduced pressure to afford a blackish sticky residue (43 g). A part of the residue (3 g) was preserved and the remaining (38 g) was subjected to column chromatography. The column was eluted with solvents of increasing polarity using a mixture of CHCl3: MeOH. The eluting extracts were collected in fractions of 100 ml each and concentrated. Following the TLC analysis, elutes of similar profiles were combined to give four fractions which were rechromatographed and eluted with a mixture of CHCl3 : MeOH. From the first fraction diphyllin (2, 41 mg) and cleistanone (1, 12.8 mg from the second fraction cleistanthins A (3, 780 mg) and D (5, 379 mg), from the third fraction 4-O-(30-O-methyl-b -D-glucopyranosyl)-diphyllin (6, 16.5 mg) and from the last fraction cleistanthin C (4, 671 mg) were obtained. Table 1: Column Chromatograms of aryl naphthalene lignans from Cleistanthus collinus TLC Examination Firstly developed the TLC plate by sing silica gel 60 GF254 and spot the sample on TLC plate and prepare TLC chromatograms. The mobile phase is developed by using solvent CH2Cl2–MeOH (1: 1). The TLC plate run over mobile phase at room temperature. Detection of aryl naphthalene’s Iodine chamber UV lamp All the TLC chromatograms are air dried for few minutes and put over at iodine chamber and pass UV light for spot identifications. Sprayer (10% methanolic sulphuric acid) 94 Scholar Research Library Rajdip U, et al. Der Pharmacia Lettre, 2018, 10 [2]:93-97 ______________________________________________________________________________ All the TLC chromatograms are air dried for few minutes and spray a visualizing solutions (10% methanolic sulphuric acid)them. Detect the spot and measure the RF values of isolated aryl naphthalene lignans. Table No.2 TLC examination of aryl naphthalene’s of cleistanthins collinus 1. 2. Figure 1: TLC examination for detection of aryl naphthalene’s in iodine chamber with UV lamp RESULT AND DISCUSSION The method use for Extraction of chemical constituents from Cleistanthus collinus on the basis of solvent used with respective polarity and their optimization was validated. The optimization of extraction conditions on the basis of three parameters as optimization of solvent, effective time and volume of solvent. Isolation of aryl naphthalene by using column chromatography with suitable eluting fractions In which similar profiles were combined to give four fractions which were re-chromatographed and eluted with a mixture of chloroform and methanol. From the first fraction diphyllin and cleistanone, from the second fraction cleistanthins A and, from the third fraction 4-O-(30-O-methyl-ß- D-glucopyranosyl)-diphyllin and from the last fraction cleistanthin C were collected. In TLC examination, the mobile phase is used as CH2Cl2 and CH3OH (1:1) and run over isolated aryl naphthalene lignans and measure RF value and weight of lignans. 1 Cleistanone 2 Diphyllin OH 7b OH 2a 2aOMe 1 1 MeO MeO 8 2 9 7 7a 2 9 7 7a O O 6 6 3 10 6a 3 10 6a MeO 5 MeO 5 3a 4 3a 4 1' O 1' O 2' 6' 2' 6' 5' 5' 3' 3' 4' O 4' O O 5'a O 5'a 9-(benzo[d][1,3]dioxol-5-yl)-4hydroxy-3,6,7- 9-(benzo[d][1,3]dioxol-5-yl)-4-hydroxy- trimethoxynaphtho[2,3-c]furan-1(3H)-one 6,7-imethoxynaphtho[2,3-c]furan-1(3H)- one 95 Scholar Research Library Rajdip U, et al. Der Pharmacia Lettre, 2018, 10 [2]:93-97 ______________________________________________________________________________ 3 Cleistanthins A 4 Cleistanthins C HO OH HO 2"a 1" OCH 3 5"'a 2" 5" 2" 3" 1" HOH2C OCH3 5"' O 6"' OH O 4" O 5" 1"' 3" 4" 2a 4"a 3"' 2a 3"a 1 2"' 1 8 H CO MeO OCH HO 4"' MeO 3 2 39 7 7a 2 9 7 7a HO O O 6 6 3 10 6a 3 10 6MaeO MeO 5 4 5 3a 4 3a O 1' O 1' 2' 2' 6' 6' 5' 3' 5' 3' 4' O 4' O O 5'a O 5'a 4-((2R,3R,4R)-1,2,5-trihydroxy-3,4- 1[4-(tetrahydro-6-hydroxy-4,5- dimethoxypentyloxy)-9-benzo [d] dimethoxy-2H-pyran-3-yl)-6- [1,3]dioxol-5-yl)-6,7-dimethoxy (hydroxymethyl)cyclohexane-1,2,3- naphtho[2,3-c]furan-1(3H)-one trihydroxy] 9-(benzo[d][1,3]dioxol-5- yl)-4,6,7-trimethoxynaphtho[2,3-c] furan-1(3H)-one 5 Cleistanthins D 6 [4-O-(3’-methoy-ß -D- glucopyranosyl)2"a -diphyllin] 1" OCH 3 2"a 5"a 2" 3" H CO HO OCH3 OCH 3 O 3 HO OH 2" 5" 5" O 4" 4" 2a 1 3" MeO CH2OH 1" OH 2 9 7a 6" 7 O 3"a OH H3CO 2a O 1 OH MeO 8 6 2 9 7 7a 3 10 6a MeO 4 5 O 3a 6 1' O 3 10 6a MeO 5 3a 4 2' 6' 1' O 2' 6' 5' 3' 5' 4' O 3' 4' O O 5'a O 5'a 9-(benzo[d][1,3]dioxol-5-yl)-6,7- 4-((2R,3R,4R)-1,2,3,4,5- dimethoxy-4-(tetrahydro-5-hydroxy-6- pentahydroxy-2,3,5- (hydroxymethyl)-3,4-dimethoxy-2H- trimethoxypentyloxy)-9- pyran-2-yloxy)naphtho[2,3-c]furan- (benzo[d][1,3]dioxol-5-yl)-6,7- 1(3H)-one dimethoxynaphtho[2,3-c]furan- 1(3H)-one Figure 2: Structural representation of isolated aryl naphthalene from Cleistanthus collinus CONCLUSION Aryl naphthalene’s are successfully extracted by petroleum ether and isolation by using column chromatography with effective time of fractions.
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