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New Lanostene-Type Triterpenes from the Oleo-Gum Resin of Commiphora Myrrha (Nees) Engl

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New Lanostene-Type Triterpenes from the Oleo-Gum Resin of Commiphora Myrrha (Nees) Engl Innovare International Journal of Pharmacy and Pharmaceutical Sciences Academic Sciences ISSN- 0975-1491 Vol 6, Issue 5, 2014 Original Article NEW LANOSTENE-TYPE TRITERPENES FROM THE OLEO-GUM RESIN OF COMMIPHORA MYRRHA (NEES) ENGL MOHD. SHUAIB a,b , MOHD. ALI a*, KAMRAN J. NAQUVI a a Phytochemistry Research Laboratory, Department of Pharmacognosy and Phytochemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi-110 062, India. b Kalka Institute for Research & Advanced Studies, Meerut-250006, Uttar Pradesh. Email: [email protected] Received: 23 Mar 2014 Revised and Accepted: 25 Apr 2014 ABSTRACT Objective: To investigate the phytoconstituents from the oleo-gum resin of Commiphora myrrha (Nees) Engl. Methods: The structures of isolated phytoconstituent have been elucidated on the basis of spectral analysis and chemical reactions. Results: Phytochemical investigation of the methanolic extract of the oleo-gum resin resulted in the isolation of three new tetracyclic triterpenoids, characterized as lanost-5,9(11), 20(21), ( Z)-23,25-pentaene-3β-yl acetate (myrrhalanostenyl acetate, 3); lanost-5, ( Z)-22,25(27)-trien-3β-ol- 21,24 α-olide (myrrhalanostenol, 5) and lanost-5-en-3α-ol-21, 24 α-olide-26-oic acid (myrrhalanostenoic acid, 6) along with three aliphatic esters identified as n-heptadecanyl capriate (1), n-dodecanyl myristate (2) and n-henetriacosanyl laurate (4). Conclusion: The phytochemical investigation of oleo-resin of C. myrrha gave three new lanostene-type triterpenoid along with some known phytoconstituents. These lanostene-type triterpenoid are isolated for the first time from this plant source. Keywords: Commiphora myrrha , Burseraceae, Oleo-gum resin, Lanostenoids, Aliphatic esters. INTRODUCTION Plant material Commiphora myrrha (Nees) Engl. (Burseraceae) is a small tree The crude oleo-gum resin of C. myrrha was procured from the local which grows in small sandy and rocky regions of Somalia, Sudan, market of the Khari Baoli, Delhi. The sample was authenticated by Ethiopia, Kenya and Saudi Arabia. The schizogenous cavities of Dr. H.B. Singh, Taxonomist, NISCAIR, CSIR, New Delhi. A voucher the stem and branches of this tree produce a scented oleo-resin specimen of the sample (No. N/R/C/-06-07/803/120) was which is known as myrrh. It is imported into India since long deposited in the NISCAIR, RHM Division, Dr. K.S. Krishnan Marg time and used in perfumery as food additive, fragrance, incense, (Near Pusa Gate), New Delhi. antiseptic, astringent, stimulant, stomachic, tonic and for embalming. It is an ingredient of toothpastes, mouthwashes and Extraction and isolation dentifrices. Myrrh tincture is useful in menstrual disorders and The air dried oleo-gum resin (2.5 kg) was coarsely powdered and chlorosis. In China, it is prescribed to treat wounds, extracted with methanol at room temperature for one week. The inflammation and menstrual pain due to blood stagnation [1]. extract was filtered and concentrated under reduced pressure to get Cadinenes, calamenes, triacont-1-ene [2], commiphoric acids, 185 g (yielded 7.4 %) of dark brown mass. The concentrated extract furanosesquiterpenoids [3-10], eudesmol and triterpenoids [11] of the oleo-resin was dissolved in minimum amount of methanol and and volatile oil [12] have been reported from the oleo-resin of C. adsorbed on silica gel (60-120 mesh) to form slurry. The slurry was myrrha . This paper describes the isolation of three new air dried and filled up in a silica gel column (1.6 m × 16 mm × 2 mm) tetracyclic lanostene-type triterpenoids along with three known loaded in petroleum ether and then eluted successively with aliphatic esters from the oleo-resin obtained from the Khari different solvents in increasing order of polarity in various Baoli market of Delhi. combinations, such as petroleum ether, petroleum ether- chloroform (9:1, 3:1, 1:1, 1:3), chloroform, chloroform-methanol (19.9:0.1, 99:1, MATERIALS AND METHODS 97:3, 19:1, 93:7, 9:1, 17:3, 3:1, 3:2, 2:3) and methanol. Various fractions were collected separately and matched by TLC to check Instrumentation and techniques homogeneity. Similar fractions having the same R f values were Melting points were determined on a Perfit melting apparatus combined and crystallized. The isolated compounds were (Haryana, India) and are uncurrected. UV spectra were measured recrystallized to get pure compounds. The following compounds with a Lambda Bio 20 spectrophotometer (Perkin-Elmer- were isolated from the methanolic extract of C. myrrha oleo-gum Rotkreuz, Switzerland) in methanol. Infra red spectra were resin: recorded on Bio-Rad FTIR 5000 (FTS 135, Kawloon, Hong Kong) n-Heptadecanyl capriate (1) - spectrophotometer using KBr pellets; γ max values are given in cm 1. 1H and 13 C NMR spectra were screened on Avance DRX 400, Elution of the column with petroleum ether produced a light Bruker spectrospin 400 and 100 MHz instruments (Karlesruthe, coloured sticky mass of 1, recrystallized from methanol-acetone Germany) using TMS as an internal standard. (9:1), 460 mg (0.0184 % yield); Rf: 0.73 (petroleum ether- chloroform; 9: 1); m.p.: 76-78 °C; +ve ion FAB MS m/z (rel. int.) : 410 Mass spectra were scanned by effecting FAB ionization at 70 eV + [M] (C 27 H54 O2) (33.1), 171 (57.5), 155 (61.3). on a JEOL-JMS-DX 303 spectrometer (Japan) equipped with direct inlet probe system. Column chromatography was n-Dodecanyl myristate (2) performed on silica gel (60-120 mesh; Qualigen, Mumbai, India). TLC was run on silica gel G (Qualigen). Spots were visualised by Further elution of the column with petroleum ether gave a exposing to iodine vapours, UV radiation, and spraying with colourless amorphous powder of 2, recrystallized from acetone- ceric sulphate. methanol (1:1), 1.41 g (0.0564 % yield); Rf: 0.77 (chloroform- Ali et al. Int J Pharm Pharm Sci, Vol 6, Issue 5, 372-375 methanol; 97: 3); m.p.: 90- 92 °C; +ve ion FAB MS m/z (rel. int.) : 396 29.88 (C-7), 38.47 (C-8), 49.76 (C-9), 37.51 (C-10), 22.19 (C-11), + [M] (C 26 H52 O2) (15.6), 227 (33.1), 211 (26.3), 185 (26.7), 169 (73.5). 26.43 (C-12), 42.25 (C-13), 46.89 (C-14), 31.58 (C-15), 33.69 (C-16), 51.02 (C-17), 15.41 (C-18), 18.66 (C-19), 41.08 (C-20), 173.08 (C-21), Myrrhalanostenyl acetate (3) 40.61 (C-22), 24.03 (C-23), 82.65 (C-24), 30.09 (C-25), 181.57 (C-26), Elution of the column with petroleum ether-chloroform (9:1) 21.75 (C-27), 24.56 (C-28), 28.41 (C-29), 14.89 (C-30), +ve ion FAB MS + yielded yellow solid mass of 3, recrystallized from petroleum ether- m/z (rel. int.) : 486 [M] (C 30 H46 O5) (5.1), 334 (10.5), 320 (15.1), 300 (28.2), 297 (15.6), 294 (12.1), 280 (24.7), 266 (12.8), 220 (15.2), 206 acetone (1:1), 1.1g (0.044% yield), R f: 0.81 (petroleum ether- (14.2), 192 (16.3), 171 (23.5), 166 (23.5), 152 (20.6). chloroform (9:1); m.p.: 70-71°C, UV λ max (MeOH): 223, 268 nm (log ε 4.3, 3.7); IR νmax (KBr): 2933, 2852, 1741, 1640, 1445, 1378, 1217, − RESULTS AND DISCUSSION 1 1 1093, 1037, 758 cm ; H NMR (CDCl 3): δ 5.73 (1H, m, H-11), 5.49 (1H, m, H-6), 5.57 (1H, d, J=5.5 Hz, H-24), 5.21 (1H, ddd, J=5.1, 8.5, Compounds 1, 2 and 4 are fatty acid esters characterized as n- 5.5 Hz, H-23), 4.94, 4.87 (1H each, brs, H 2-21), 4.77, 4.70 (1H each, heptadecanyl caprate, n-dodecanyl myristate and n-henetriacosanyl brs, H2-26), 4.13 (1H, dd, J= 5.7, 7.5 Hz, H-3α), 2.02 (3H, brs, OCOCH 3 laurate, respectvely (Figure 1). ), 1.66 (3H, brs, Me-26), 1.38 (3H, brs, Me-28), 1.23 (3H, brs, Me-19), Compound 3, designated as myrrhalanostenyl acetate, was obtained 1.19 (3H, brs, Me-30), 1.03 (3H, brs, Me-29), 0.91 (3H, brs, Me-18); 13 as a yellow solid mass from petroleum ether-chloroform (9:1) C NMR (CDCl 3): δ 39.47 (C-1), 27.94 (C-2), 84.88 (C-3), 40.74 (C-4), eluants. Its IR spectrum displayed characteristic absorption bands 141.64 (C-5), 125.62 (C-6), 29.49 (C-7), 44.55 (C-8), 149.89 (C-9), − − for ester group (1741 cm 1) and unsaturation (1640 cm 1). On the 36.35 (C-10), 122.40 (C-11), 22.35 (C-12), 46.14 (C-13), 49.37 (C- basis of +ve FAB mass and 13 C NMR spectra, the molecular ion peak 14), 34.35 (C-15), 31.72 (C-16), 52.17 (C-17), 19.51 (C-18), 20.93 (C- of 3 was determined at m/z 462 consistent with the molecular 19), 139.41 (C-20), 111.86 (C-21), 41.59 (C-22), 119.64 (C-23), formula of a triterpenic ester C32 H46 O2. The ion fragments formed at 129.68 (C-24), 136.43 (C-25), 109.78 (C-26), 24.72 (C-27), 23.34 (C- + + m/z 194 [C 6,7 -C9,10 , fission] , 208 [C 7,8 -C9,10 fission] indicated the 28), 26.72 (C-29), 14.08 (C-30), 22.06, 170.57 (OCOCH 3); +ve ion + location of acetyl group in ring A and the existence of a vinylic FAB MS m/z (rel.
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