Novel ursane-type triterpene from the fresh leaves of Carissa carandas and evaluation of cytotoxicity.

One novel ursolic acid derivative sabiracin 1 (11,25-epoxy-3ß-hydroxy-urs-12-en-28-oic acid) was isolated from the leaves of Carissa carandas, together with five known compounds para hydroxy benzaldehyde (2), ursolic acid (3), carissin (4), 22α-hydroxyursolic acid (5) and ß-sitosterol-3-O-ß-D-glucopyranoside (6). Compounds 2 and 5 were isolated for the first time from this genus. Structure elucidation was done by the help of spectroscopic techniques. Compounds 1-3, 5 and 6 were examined against oral cancer (CAL-27) and lung cancer (NCI-H460) cell lines. 6 showed good activity against oral cancer (IC50 18.69 µM), moderate activity against lung cancer (IC50 63.34 µM) and no cytotoxicity against normal cell lines.

Volatile constituents and in vitro activity of Syzygium aromaticum flower buds (clove) against human cancer cell lines.

The methanolic extract (SA-EXT) of Syzygium aromaticum flower buds and its fractions tested against three human cancer cell lines viz uterine cervix (HeLa), breast (MCF-7) and lung NCI (H-460) using sulforhodamine-B assay. The ethyl acetate soluble sub fraction (SA-EAS) was active only against HeLa cells with GI50value of 36± 3.4µg/mL. The most active sub-fraction (SA-PES-Fr-2) showed growth inhibition (GI50: 36, 50 and 68µg/ml against MCF-7, HeLa and NCI-H-460 cancer cell lines, respectively) with cytotoxic effect LC50= 88 ± 3.4 µg/mL against HeLa and LC50=86 ± 2.8 µg/mL against MCF-7. The most active sub-fraction (SA-PES-Fr-2) analyzed by GC and GC-MS techniques revealed that eugenol was most abundant (85.34%) along with minor constituents. Thus it can be concluded that growth inhibitory and cytotoxic effect residing in Syzygium aromaticum flower buds (clove) is more likely due to eugenol.

Muscle relaxant activities of pistagremic acid isolated from Pistacia integerrima.

The aim of the current work was to explore the muscle relaxant effect of pistagremic acid (PA) isolated from Pistacia integerrima in various animal paradigms. In a rotarod test, PA caused a significant (p<0.05) muscle relaxant potential in a dose-dependent manner. When studied in the inclined plane test, pretreatment with PA (5 and 10 mg/kg) caused promising activity (p<0.05) after treatment for 30, 60 and 90 min. The muscle relaxant potential of PA was strongly complimented by the traction and chimney tests, showing a dominant effect after 60 min of treatment. In conclusion, PA possesses strong muscle relaxant activity in various animal-based models.

Identification of new potent inhibitor of aldose reductase from Ocimum basilicum.

Recent efforts to develop cure for chronic diabetic complications have led to the discovery of potent inhibitors against aldose reductase (AKR1B1, EC 1.1.1.21) whose role in diabetes is well-evident. In the present work, two new natural products were isolated from the ariel part of Ocimum basilicum; 7-(3-hydroxypropyl)-3-methyl-8-ß-O-d-glucoside-2H-chromen-2-one (1) and E-4-(6'-hydroxyhex-3'-en-1-yl)phenyl propionate (2) and confirmed their structures with different spectroscopic techniques including NMR spectroscopy etc. The isolated compounds (1, 2) were evaluated for in vitro inhibitory activity against aldose reductase (AKR1B1) and aldehyde reductase (AKR1A1). The natural product (1) showed better inhibitory activity for AKR1B1 with IC50 value of 2.095±0.77µM compare to standard sorbinil (IC50=3.14±0.02µM). Moreover, the compound (1) also showed multifolds higher activity (IC50=0.783±0.07µM) against AKR1A1 as compared to standard valproic acid (IC50=57.4±0.89µM). However, the natural product (2) showed slightly lower activity for AKR1B1 (IC50=4.324±1.25µM). Moreover, the molecular docking studies of the potent inhibitors were also performed to identify the putative binding modes within the active site of aldose/aldehyde reductases.

Coadministration of black seeds and turmeric shows enhanced efficacy in preventing metabolic syndrome in fructose-fed rats.

Among noncommunicable diseases, metabolic syndrome (MS), a cluster of metabolic disorders including obesity, hyperglycemia, hyperlipidemia and hypertension, is highly prevalent in modern society. Its management requires lifestyle modifications and/or the life-long use of multiple medications, hence demanding development of safe alternative remedies. This study was aimed to establish the efficacy of combined use of black seeds and turmeric using fructose-fed rat model of MS. The high-performance liquid chromatographic fingerprints of turmeric and black seeds showed the presence of curcumin and thymoquinone, respectively, as their major constitutes. Different doses of black seeds and turmeric, individually and in combination, were administered to fructose-fed rats for up to 6 weeks representing characteristic features of MS. At 3 weeks of the treatment, black seeds and turmeric lowered (P < 0.01) high blood pressure and low-density lipoprotein cholesterol, respectively, whereas their coadministration reduced (P < 0.01) both high blood pressure and hypertriglyceridemia. At 6 weeks, the coadministration of both herbs, at half the doses of individual herbs, was the most effective (P < 0.001) in preventing hypertension, hyperglycemia, dyslipidemia, hyperinsulinemia, and endothelial dysfunction than the individual herbs. This study demonstrates the therapeutic superiority of the combination of black seeds and turmeric at low doses over individually tested herbs, in improving features of MS.

Chemical constituents and biological activities of Cirsium leucopsis, C. sipyleum, and C. eriophorum.

Two endemic Cirsium species, C. leucopsis DC. and C. sipyleum O. Schwarz, and C. eriophorum (L.) Scop. growing in Turkey were investigated to establish their secondary metabolites, fatty acid compositions, and antioxidant and anticholinesterase potentials. Spectroscopic methods were used to elucidate the structures of thirteen known compounds (p-hydroxy-benzoic acid, vanillic acid, cis-epoxyconiferyl alcohol, syringin, balanophonin, 1'-O-methyl-balanophonin, apigenin, kaempferol-3- O-ß-D-glucopyranoside, kaempferol-3-O-α-L-rhamnopyranoside, taraxasterol, taraxasterol acetate, ß-sitosterol, ß-sitosterol-3-O-ß-D-glucopyranoside). cis-Epoxyconiferyl alcohol and 1'-O-methyl- balanophonin were isolated for the first time from Cirsium species. Palmitic acid (47.1%) was found to be the main fatty acid of C. leucopsis, linoleic acid in both C. sipyleum (42.1%) and C. eriophorum (37.8 %). Assays of ß-carotene bleaching, scavenging of 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals, 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium (ABTS) cation radicals, and superoxide anion radicals, as well as cupric reducing antioxidant capacity (CUPRAC) were used to determine the antioxidant activities of the extracts and isolated compounds. Vanillic acid, balanohonin, and kaempferol-3-O-aαL-rhamnopyranoside exhibited strong antioxidant activity. Taraxa-terol was a potent inhibitor of acetyl- and butyrylcholinesterase activity, respectively.

Anti-inflammatory and urease inhibitory iridoid glycosides from Nyctanthes arbor-tristis Linn.

ETHNOPHARMACOLOGICAL RELEVANCE: Nyctanthes arbor-tristis Linn. has been used by Ayruvedic physicians for the cure of different diseases including ulcers, gastric and inflammatory diseases. AIM OF THE STUDY: To isolate and identify compounds from this source and investigate their therapeutic potential for the treatment of gastric ulcer and related disorders. MATERIAL AND METHODS: The ethanol extract of fresh aerial parts of N. arbor-tristis was used in the present studies which was subjected to a bio-assay guided fractionation followed by chromatographic separations. The structures of pure compounds were elucidated using various spectroscopic techniques. The inhibition of urease enzyme was evaluated by weatherburn indophenol method. Molecular docking studies were determined by using Molecular Operating Environment (MOE) version 2020.0901 version. The intracellular ROS production from phagocytes was determined by chemiluminescence assay and NO generation was detected by Griess method. The proinflammatory cytokine TNF-α was quantified by ELISA. Cytotoxic activity was assessed by MTT assay. RESULTS: One previously undescribed iridoid glycoside arborside F (1) and four known iridoid glycosides arborside A (2), arborside C (3), loganin (4) and 7-O-trans-cinnamoyl-6ß-hydroxyloganin (5) were isolated and characterized in the present studies and their urease inhibitory activity was determined. Among these, 2 and 5 showed strong urease inhibition (IC50 = 12.1 ± 1.74 and 14.1 ± 0.59 µM respectively) (standard acetohydroxamic acid IC50 = 20.3 ± 0.42 µM), whereas rest of compounds showed moderate to low inhibition. Kinetic studies revealed that compounds 2 and 5 possess competitive type of inhibition. Molecular docking showed polar and non-polar interactions of compounds 2 and 5 with urease enzyme residues. Compounds 2 and 3 showed inhibition of ROS from whole blood (IC50 = 1.6 ± 0.3 and 2.5 ± 0.09 µg/mL respectively) and PMNs (IC50 = 1.5 ± 0.03 and 1.4 ± 0.0 µg/mL respectively). Compound 2 significantly inhibited nitric oxide and proinflammatory cytokine TNF-α (IC50 = 18.2 ± 3.0 and 73.8 ± 6.6 µg/mL respectively). Compounds 1, 4 and 5 were inactive on ROS. All isolated compounds were non-toxic on normal mouse fibroblasts (NIH-3T3) cells. CONCLUSIONS: The ethno pharmacological repute of N. arbor-tristis in treating gastric and anti-inflammatory ailments is supported by present studies which resulted in isolation of a potent urease inhibitory and anti-inflammatory agent arborside A (2) a potential anti-ulcer and anti-inflammatory drug lead.

An efficient synthesis of O- and N- alkyl derivatives of 4-aminobenzoic acid and evaluation of their anticancer properties.

A series of twenty alkyl derivatives (2-21) of 4-amino benzoic acid (1, PABA) have been prepared using potassium carbonate and opportune alkylating agents under simple and mild reaction conditions. Compounds (16-21) are reported for the first time. Electron impact mass spectrometry (EIMS), Fourier transform infrared (FTIR) and Proton nuclear magnetic resonance (1H-NMR) spectroscopic techniques were adopted for the characterization of these analogues. In the present study, the cytotoxic screening of sixteen compounds (3, 5-11, 13 and 15-21) was also achieved against lung (NCI-H460) and oral squamous carcinoma (CAL-27) cell lines. Compound 20 has shown magnificent inhibitory properties against NCI-H460 cell line (IC50 15.59 and 20.04 µM, respectively) at a lower dose than that of the control (cisplatin; IC50 21.00 µM). One-way analysis of variance (ANOVA), t-test and Pearson correlation coefficient (PCC) have been performed to determine the reliability of current data through statistical package for the social sciences (SPSS).

Isolation of secondary metabolites from Syzygium aromaticum (L.) Merr. & L.M.Perry. (cloves), and evaluation of their biological activities.

Phytochemical investigation of dried flower buds of Syzygium aromaticum (L.) Merr. & L.M.Perry. (clove) led to the isolation and identification of fourteen known compounds, oleanolic acid (1), betulinic acid (2), para methyl benzoic acid (3), sabrinic acid (4) eucalyptolic acid (5), nigricin (6), 3-O-trans-para-coumaroylmaslinic acid (7), methyl maslinate (8), maslinic acid (9), 3, 4, 5-trimethoxy-3',4'-O,O-methylideneflavellagic acid (10), lantanone (11) 3,4,3'-trimethoxyellagic acid (12), 11-oxo-oleanolic acid (13), and ß-sitosterol-3-O-ß-D-glucopyranoside (14). Their structures were identified by 1H NMR, 13C NMR, Mass spectroscopic techniques, and comparison with the literature data. Compounds 3, and 7-9 showed a strong mortality against root knot nematode, Meloidogyne incognita at 0.125% concentration after 72 hours (88-92% inhibition). Compound 4 showed a good anti-glycation activity with IC50 = 142.0 ± 1.8 µM when compared with standard, i.e. rutin (IC50 = 54.59 ± 2.20 µM). Compound 10 showed a comparable urease inhibitory activity (IC50 = 26.1 ± 0.19 µM) with the positive control thiourea (IC50 = 24.5 ± 0.34 µM).

Phytochemicals from Carissa carandas with potent cytotoxic and anti-inflammatory activities.

Six natural products (1-6) were isolated from the fresh leaves of Carissa carandas including ursolic acid (1), ursolic acid-γ-lactone (2), 27-O-Z-p-coumaroyl ursolic acid (3), 23-hydroxy ursolic acid (4), uvaol (5) and ursolic aldehyde (6). Their structure elucidation was done by modern spectroscopic techniques including 1H-NMR, 13C-NMR and comparison with reported data. All compounds were known, while 2-4 were isolated for the first time from the genus Carissa. Isolated compounds were screened for their cytotoxic via MTT assay and anti-inflammatory potential via luminol-enhanced chem-iluminescence assay. Compounds 3 and 4 showed potent activity against lung cancer cell line (NCI-H460), and 4 showed potent anti-inflammatory activity against reactive oxygen species production from human whole blood phagocytes. Compound 5 displayed good selective cytotoxicity against NCI-H460 and did not provoke cytotoxicity against normal cell line upto 250 µM. Compounds 3-5 were identified as potential anti-cancer drug leads.

Isolation and characterization of anti-inflammatory and anti-proliferative compound, for B-cell Non-Hodgkin lymphoma, from Nyctanthes arbor-tristis Linn.

ETHNOPHARMACOLOGICAL RELEVANCE: Nyctanthes arbor-tristis Linn. is native to Indo-Pak sub-continent and has high medicinal values in Ayureda. This plant has been used traditionally for the treatment of sciatica, rheumatism, chronic fever, diabetes, snakebite, dysentery, cachexia and cancer. Studies have shown many pharmacological properties such as anti-cancer efficacy against Dalton's ascetic lymphoma, cytotoxicity against T-cell leukemia, anti-inflammatory, anti-diabetic and anti-oxidant effects. AIM OF THE STUDY: Aim of the study was to explore the anti-inflammatory and anti-proliferative potential of N. arbor-tristis. MATERIAL AND METHODS: Ethanol extract of fresh and uncrushed aerial parts of N. arbor-tristis was used in the present study. A new compound nyctanthesin A was isolated following a bioactivity-guided fractionation and chromatographic separations. Its chemical structure was elucidated through spectral studies including 1D, 2D-NMR experiments and HREIMS. The intracellular reactive oxygen species (ROS) and nitric oxide (NO) generation from phagocytes were detected by chemiluminescence technique and Griess method, respectively. TNF-α and TGF-ß production was quantified by ELISA. Anti-lymphoma and cytotoxic activities were assessed by alamar blue and MTT assays, respectively. The transcription and protein expression level of Bcl-2, COX-2, p38 MAPK, PDL-1, NF-κB, c-Myc and PNF-κB was performed by qRT-PCR and protein blot assays, respectively. RESULTS: Petroleum ether insoluble fraction of the ethanol extract of fresh and uncrushed aerial parts of N. arbor-tristis revealed anti-inflammatory potential by inhibiting ROS. A previously undescribed compound nyctanthesin A was isolated from this fraction and characterized by UV, IR, NMR and HREIMS. It showed significant anti-inflammatory property by inhibiting ROS, NO and TNF-α production. The strong anti-proliferative effects on B- cell lymphoma cells, DOHH2 and Raji, revealed its anti-lymphoma potential along with non-toxic profile against BJ and NIH-3T3 fibroblast cells of normal origin. The qRT-PCR results showed marked inhibition of Bcl-2, COX-2, p38 MAPK, PDL-1, c-Myc, NF-κB, and PNF-κB at transcription level in DOHH2 cells with comparatively lesser but significant effects in Raji cells, where the expression of Bcl-2 gene was not affected. The protein expression of PNF-κB in DOHH2 cells was inhibited by 66% (P < 0.05) and COX-2 in both cell lines was inhibited by 50% (P < 0.05) at 60 µg/mL. A moderate non-significant inhibition of TGF-ß (∼20%) was observed in both cell lines at 100 µg/mL CONCLUSIONS: Scientific evidences reported here validate the anti-inflammatory and anti-cancer potential of the plant.

Chemical constituents of Cordia latifolia and their nematicidal activity.

Following nematicidal activity-guided isolation studies on the fruits, bark, and leaves of Cordia latifolia, two new constituents, cordinoic acid (=11-oxours-12-ene-23,28-dioic acid; 1) and cordicilin (=2-{[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-[4-hydroxy-3-(stearoyloxy)phenyl]propanoic acid; 2) were isolated from the stem and leaves, respectively, together with nine known compounds, namely cordioic and cordifolic acid from the stem bark, latifolicin A-D and rosmarinic acid from the fruits, and cordinol and cordicinol from the leaves. Their structures were determined by means of spectroscopic analyses including 1D- and 2D-NMR techniques. The nematicidal activities of these constituents were determined against the root-knot nematode Meloidogyne incognita. Hundred percent mortality was caused by all of these after 72 h at a 0.125% concentration. Compound 1 and cordioic acid were most active and caused 100% mortality after 24 h at a 0.50% concentration. Furthermore, compound 2, the ester of rosemarinic acid, was found to be more active than the free acid.

Novel ferulic acid and benzophenone derivatives from the flower buds of Syzygium aromaticum.

Phytochemical investigation of clove resulted in the isolation of two new natural compounds, a ferulic acid derivative, sabrinic acid (1) and a benzophenone derivative (2) together with two known compounds kaempferol-3,5-dimethyl ether (3) and 4-methyl benzoic acid (4). Compounds 3 and 4 were isolated for the first time from the genus Syzygium. The structures of compounds were elucidated through modern spectroscopic techniques including 1D and 2D NMR spectroscopy.

Petra/Osiris/Molinspiration and Molecular Docking Analyses of 3-Hydroxy-Indolin-2-one Derivatives as Potential Antiviral Agents.

BACKGROUND: Studies on the interaction between bioactive molecules and HIV-1 virus have been the focus of recent research in the scope of medicinal chemistry and pharmacology. OBJECTIVE: Investigating the structural parameters and physico-chemical properties of elucidating and identifying the antiviral pharmacophore sites. METHODS: A mixed computational Petra/Osiris/Molinspiration/DFT (POM/DFT) based model has been developed for the identification of physico-chemical parameters governing the bioactivity of 22 3-hydroxy-indolin-2-one derivatives of diacetyl-L-tartaric acid and aromatic amines containing combined antiviral/antitumor/antibacterial pharmacophore sites. Molecular docking study was carried out with HIV-1 integrase (pdb ID: 5KGX) in order to provide information about interactions in the binding site of the enzyme. RESULTS: The POM analyses of physico-chemical properties and geometrical parameters of compounds 3a-5j, show that they are bearing a two combined (O,O)-pockets leading to a special platform which is able to coordinate two transition metals. The increased activity of series 3a-5j, as compared to standard drugs, contains (Osp2,O sp3,O sp2)-pharmacophore site. The increase in bioactivity from 4b (R1, R2 = H, H) to 3d (R1, R2 = 4-Br, 2-OCH3) could be attributed to the existence of π-charge transfer from para-bromo-phenyl to its amid group (COδ---NHδ+). Similar to the indole-based reference ligand (pdb: 7SK), compound 3d forms hydrogen bonding interactions between the residues Glu170, Thr174 and His171 of HIV-1 integrase in the catalytic core domain of the enzyme. CONCLUSION: Study confirmed the importance of oxygen atoms, especially from the methoxy group of the phenyl ring, and electrophilic amide nitrogen atom for the formation of interactions.

Nematicidal activity of oleanolic acid derivatives on Meloidogyne incognita.

In this study, oleanolic acid and its derivatives were studied for their invivo nematicidal activity against root-knot nematode (RKN) Meloidogyne incognita. A series of C-28-oleanolates including five new (5, 7-10) and seven known (1-4, 6, 11, 12) compounds were synthesised and their nematicidal activity was determined and compared with the standard nematicide furadan for the first time. The structures of the compounds were elucidated through 1H NMR, 13C NMR and EIMS. Compounds 4, 5, 7, 8 and 10 showed ∼ 90% inhibition of RKN at 0.125% concentration after 72 h showing their potential use in nematicidal control.

Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin.

Structural revision of lawsonicin, a natural product of Lawsonia alba, is reported based upon comparison of its spectral data with that of the naturally occurring dihydrobenzo[b]furan neolignan (rac)-trans-dihydrodehydrodiconiferyl alcohol, which is found to be identical. A concise synthesis of dihydrodehydrodiconiferyl alcohol, via Rh(2)[S-DOSP](4)-catalysed intramolecular C-H insertion, is described.

Antiproliferative Activity and Characterization of Metabolites of Aspergillus nidulans: An Endophytic Fungus from Nyctanthes arbor-tristis Linn. Against Three Human Cancer Cell Lines.

BACKGROUND: Endophytic fungi are receiving attention as sources of structurally novel bioactive secondary metabolites towards drug discovery from natural products. This study reports the isolation and characterization of secondary metabolites from an endophytic fungus Aspergillus nidulans, associated with Nyctanthes arbor-tristis Linn., a plant which has a traditional use to cure many ailments including cancer. OBJECTIVE: The objective of this study was to evaluate the antiproliferative activity of the metabolites of A. nidulans from N. arbor-tristis on three human cancer cell lines, lung (NCI-H460), breast (MCF-7) and uterine cervix (HeLa), and carry out their characterization. METHODS: The extracts of the endophytic fungus cultured on potato dextrose agar were subjected to various chromatographic techniques. Structures of pure compounds were determined using spectroscopic techniques. The non-polar constituents were analyzed by GC-MS. Antiproliferative activity was determined by sulforhodamine B (SRB) assay. RESULTS: The extracts and fractions showed moderate to good growth inhibition of the aforementioned human cancer cell lines. The broth extract was most potent (IC50 = 10 ± 3.1 µg/mL and LC50= 95 ± 3.9) against HeLa whereas petroleum ether insoluble fraction of mycelium was most active against NCI-H460 and MCF-7 (IC50 = 10 ± 2.1 µg/mL and 18 ± 3.1 µg/mL respectively). GC-MS led to identify 12 compounds in mycelium and 19 compounds in broth. Four pure compounds were isolated and characterized one compound 5, 10-dihydrophenazine-1-carboxylic acid (1) from broth and three 1-hydroxy-3-methylxanthone (2), ergosterol (3) and sterigmatocystin (4) from mycelium. 1 has not been reported earlier as a plant/fungal metabolite while 2-4 are new from this source. Sterigmatocystin exhibited growth inhibitory effect (IC50 = 50 ± 2.5 µM/mL) against only MCF-7 cell line whereas other compounds had IC50 > 100. CONCLUSIONS: In this paper, the cytotoxicity of mycelium and broth constituents of endophytic fungus Aspergillus nidulans from Nyctanthes arbor-tristis is reported for the first time. The study shows that fungus Aspergillus nidulans from Nyctanthes arbor-tristis is capable of producing biologically active natural compounds and provides a scientific rationale for further chemical investigations of endophyte-producing natural products.

A simple, rapid and mild one pot synthesis of benzene ring acylated and demethylated analogues of harmine under solvent-free conditions.

A simple, rapid, solvent-free, room temperature one pot synthesis of benzene ring acylated and demethylated analogues of harmine using acyl halides/acid anhydrides and AlCl(3) has been developed. Eight different acyl halides/acid anhydrides were used in the synthesis. The resulting mixture of products was separated by column chromatography to afford 10- and 12-monoacyl analogues, along with 10,12-diacyl-11-hydroxy products. In five cases the corresponding 10-acyl-11-hydroxy analogues were also obtained. Yields from the eight syntheses (29 products in total) were in the 6-34% range and all compounds were fully characterized.

Chemical constituents from the aerial parts of Lippia nodiflora Linn.

Phytochemical investigation of the methanolic extract of the aerial parts of Lippia nodiflora Linn. led to the isolation of a new triterpenoid lippiacin (1) and a benzofuranone rengyolone (halleridone, 2) through repeated silica gel column chromatography and semi preparative HPLC. The structures of these compounds were determined by spectroscopic methods, including 1D and 2D NMR, as well as by comparison with published data. A complete assignment of the 1H- and 13C-NMR data of 2 is reported based on 2D NMR (COSY-45, HMQC and HMBC) spectroscopic methods.

Isolation and structural elucidation of chemical constituents from the fruits of Morinda citrifolia Linn.

The fruits of Morinda citrifolia, Linn. afforded a new constituent, morinaphthalenone (1), and three known constituents, scopoletin (2), 1, 3-dimethoxy-anthraquinone (3) and 1, 2-dihydroxy-anthraquinone (4). The structures of these isolated compounds were determined by spectroscopic methods, including 1D- and 2D-NMR (COSY-45, HMQC, HMBC) techniques, as well as by comparison with published values.