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Triterpenoids and Steroids Isolated from Aerial Parts of Glochidion Multiloculare Abdullah Al Hasana, A.T.M

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Triterpenoids and Steroids Isolated from Aerial Parts of Glochidion Multiloculare Abdullah Al Hasana, A.T.M Pak. j. sci. ind. res. Ser. A: phys. sci. 2012 55 (3) 163-168 Triterpenoids and Steroids Isolated from Aerial Parts of Glochidion multiloculare Abdullah Al Hasana, A.T.M. Zafrul Azama, Mohammad Rashedul Haquea, b and Choudhury Mahmood Hasana* aPhytochemical Research Laboratory, Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Dhaka, Dhaka 1000, Bangladesh bCRUK Protein-Protein Interactions Drug Discovery Research Group, Department of Pharmaceutical & Biological Chemistry, School of Pharmacy, University of London, WC1N 1AX, UK (received July 26, 2011; revised November 10, 2011; accepted November 21, 2011) Abstract. This study presents the chemical investigation of the leaves and stem barks of Glochidion multiloculare (Roxb. ex Willd.) Muell.-Arg., Phyllanthaceae. Classic phytochemical investigation of organic extracts of the aerial parts of Glochidion multiloculare together with spectroscopic methods led to the isolation and characterization of four triterpenes, namely; glochidonol (1), glochidiol (2), glochidone (3), lupeol (4) and two steroids, namely; daucosterol (5) and stigmasterol (6). Keywords: triterpenes, glochidonol, glochidone, glochidiol, multiloculare, Glochidion Introduction ability (Puapairoj et al., 2005; Huang et al., 2004), antiviral activity against hepatitis B virus (Lam et al., Glochidion multiloculare (Roxb. ex Willd.) Muell.-Arg., 2006; Venkateswaran et al., 1987), anti-angiogenic Phyllanthaceae (synonym: Phyllanthus multilocularis) is effect (Huang et al., 2006), analgesic effect (Santos an evergreen shrub or small tree; bark is brownish, peeling et al., 2000, 1994), diuretic effect (Srividya and Periwal, off in thin, papery transparent flakes, tuberculated or watery; 1995), lipid lowering activity (Khanna et al., 2002), leaves are stipulated, leaf blade is elliptic; flowers are small, hypocholesterolemic activity (Adeneye et al., 2006), greenish yellow, on short with stout pedicles. No antioxidative effect (Sabir and Rocha, 2008; Harish and ethnobotanical information is known for this plant. The Shivanandappa, 2006; Raphael et al., 2002;), antidiabetic plant is found in Bhutan, India, Myanmar, Nepal and effect (Adeneye et al., 2006; Raphael et al., 2002; Bangladesh. Glochidion was regarded as a genus of the Srividya and Periwal, 1995), antiherpetic activity family Euphorbiaceae, which consists of monoecious, rarely (Álvarez et al., 2009; Yang et al., 2007), hepatoprotective dioecious trees or shrubs. But molecular phylogenetic studies effect (Sabir and Rocha, 2008; Harish and Shivanan- have shown that Phyllanthus is paraphyletic over Glochidion. dappa, 2006), anti-inflammatory action (Kassuya et al., A recent revision of the family Phyllanthaceae has subsumed 2006; Kiemer et al., 2003), antiatherogenic effect (Duan Glochidion into Phyllanthus (Hoffmann et al., 2006). et al., 2005), anti-HIV activity (Notka et al., 2004, Traditionally many Phyllanthus species are used in 2003; Ogata et al., 1992); antiplasmodial activity haemorrhoids, diarrhoea, dysentery, anaemia, jaundice, (Luyindula et al., 2004), antibacterial activity (Meléndez dyspepsia, insomnia etc. and some of them can induce and Capriles, 2006) and hypotensive activity (Leeya diuresis (Ghani, 1998). In Chinese traditional medicine et al., 2010; Srividya and Periwal, 1995) etc . Glochidion puberum is used in dysentery, jaundice, leukorrhagia, common cold, sore throat, toothache, carbuncle, Several secondary metabolites have been isolated from furuncle, rheumatic arthralgia (Fenglin et al., 2004). different Phyllanthus species, including flavonoids, lignans, alkaloids, triterpenes, phenols and tannins (Chang Biological investigations of Phyllanthus species revealed et al., 2003; Calixto et al., 1998; Ishimaru et al., 1992). that many members of the genus possess anti-tumor Many secondary metabolites were isolated from promoting ability (Huang et al., 2006; Tanaka et al., Glochidion species, including tannins (Chen et al., 1995), 2004; Rajeshkumar et al., 2004), apoptosis inducing glycosides (Otsuka et al., 2003), lignans (Otsuka et al., *Author for correspondence; E-mail:[email protected] 2000), terpenoids (Hui and Li, 1976). Previous 163 164 Choudhury Mahmood Hasan et al., investigation of Glochidion multiloculare revealed (6.0 mg) and (4) (5.8 mg), respectively. Fractions 108-111 glochidiol, glochilocudiol, glochidone and dimedone were combined and subjected (380 mg) to Sephadex (Talapatra et al., 1973). LH-20 chromatography using 2:5:1 n-Hexane/ CH2Cl2/ MeOH, 1:9, 1:1 MeOH/CH Cl and finally 100% MeOH This study was taken to describe the chemical charac- 2 2 as mobile phases. As a result, 47 fractions were obtained terization of steroids and triterpenes obtained from and combined on the basis of TLC. Here, fractions 20-21 G. multiloculare (synonym: Phyllanthus multilocularis) yielded 10.0 mg of compound (2). along with a small review regarding the importance of these compounds. This work supports the subsumption Results and Discussion of Glochidion into Phyllanthus. Chemical study of the leaves and stem barks of Materials and Methods G. multiloculare (Roxb. ex Willd.) Muell.-Arg., Phyllan- General experimental procedure. Silica-gel chromato- thaceae led to the identification of four triterpenes, namely; graphy was performed using kieselgel 60 (mesh 70-230). glochidonol (1) glochidiol (2), glochidone (3) and lupeol Prep TLC: glass plates preparative with silica gel 60 (4) and two steroids, namely; daucosterol (5) and stigmasterol (6). PF254 (0.5 mm thickness, Merck); detection with vanillin spray. Gel permeation chromatography was performed using Sephadex LH-20. 1H NMR spectra were acquired in CDCl3 (d values were reported in reference to CHCl3 at 7.25 ppm) on a Bruker Avance 400 MHz Ultrashield NMR spectrometer equipped with broadband and selective (1H and 13C) inverse probes. Plant material. Glochidion multiloculare (Roxb. ex Willd.) Muell.-Arg., Phyllanthaceae plant was collected from Rajendrapur, Gazipur, Bangladesh in the month of August, 2009, and was identified by the Bangladesh National Herbarium, Dhaka, Bangladesh. A voucher specimen (ACC. No. 34391) of the plant has been deposited in the Herbarium. 1 Extraction and isolation. The powdered leaves (1000 g) The H NMR (400 MHz, CHCl3-d1) spectrum of compound of G. multiloculare were soaked in methanol (3 L) for 15 (1) displayed methyl group resonances at d 0.79, 0.83, days. Part of the residue (5 g), obtained from methanol 0.97, 1.03, 1.05, 1.05 and 1.69 for H3-28, H3-25, H3-27, extract on removal of the solvent at reduced pressure, was H3-24, H3-23, H3-26 and H3-30, respectively. The spectrum subjected to modified Kupchan partitioning (VanWagenen displayed two singlets at d 4.68 and 4.56 (1H each) et al., 1993) to obtain 1.2 g n-hexane soluble fraction; it assignable to protons at C-29. A doublet of triplets at d was again subjected to gravity column chromatography 2.38 (1H, J = 11.2, 6.0 Hz) was indicative of H-19. A (n-hexane, n-hexaneEtOAc, EtOAc and EtOAc-MeOH multiplet at d 3.89, integrating one proton, was indicative in increasing order of polarity). As a result, 167 fractions of H-1. Two doublets of doublets at d 2.98 (1H, J = 14.4, were obtained and combined on the basis of TLC. Here, 8.0 Hz) and 2.21 (1H, J = 14.4, 3.6 Hz) were assignable fractions 67-76, 85-91 and 160-167 yielded compounds to Hax-2 and Heq-2, respectively. The spectral features of (6) (12.0 mg), (1) (3.0 mg) and (5) (5.0 mg) respectively. compound (1) were in close agreement to those observed for glochidonol (Hui and Li, 1976). This is the first report The powdered barks (700 g) of G. multiloculare were of this compound from G. multiloculare. soaked in methanol (3 L) for 15 days. Part of the residue 1 (15 g) obtained from methanol extract on removal of the The H NMR (400 MHz, CHCl3-d1) spectrum of solvent at reduced pressure was subjected to gravity column compound (2) showed methyl group resonances at chromatography (n-hexane, n-hexane-EtOAc, EtOAc and d 0.74, 0.78, 0.90, 0.93, 0.94, 1.04 and 1.66 to indicate EtOAc-MeOH in increasing order of polarity). As a result, H3-24, H3-28, H3-25, H3-27, H3-23, H3-26 and H3-30, 111 fractions were obtained and combined on the basis of respectively. The spectrum displayed two singlets at TLC. Fractions 45-47 and 58-59 afforded compounds (3) d 4.67 and 4.54 (1H each) assignable to protons at Steroids and Triterpenes from Glochidion multiloculare 165 C-29. A doublet of triplets at d 2.36 (1H, J = 11.2, 6.0 Functions of sterols in planta are related to cell membrane Hz) was indicative of proton at C-19. A triplet of structure and hormonal action. But these compounds doublets at d 3.41 (1H, J = 11.2, 5.6 Hz) was assignable exert various biological effects on other organisms. For to proton at C-1. A broad doublet at d 3.23 (1H, J = example, daucosterol possesses immunoregulatory activity 11.6 Hz) was indicative of H-3. The spectral features (Lee et al., 2007). Stigmasterol inhibits several pro- of compound (2) were in close agreement to those inflammatory and matrix degradation mediators typically observed for glochidiol (Srivastava and Kulshreshtha, involved in osteoarthritis-induced cartilage degradation 1988; Hui and Li, 1976). It is the second report of this (Gabay et al., 2010). It also shows thyroid inhibitory, compound from G. multiloculare. antiperoxidative and hypoglycemic effects in mice (Panda et al., 2009); reduces plasma cholesterol levels and The 1H NMR (400 MHz, CHCl -d ) spectrum of com- 3 1 inhibits hepatic synthesis and intestinal absorption of pound (3) displayed methyl group resonances at d 0.80, cholesterol in the rat (Batta et al., 2006). Moreover, 0.95, 1.06, 1.07, 1.10, 1.12 and 1.70 for H -28, H -27, 3 3 stigmasterol and b-sitosterol neutralizes viper and cobra H -23, H -24, H -26, H -25 and H -30, respectively. 3 3 3 3 3 venom (Gomes et al., 2007). The spectrum displayed two broad singlets at d 4.69 and 4.59 (1H each) assignable to protons at C-29.
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