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Molecules, Volume 14, Issue 1 (January 2009), Pages 1-585

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Open AccessEditorial Molecules’ Highlights in 2008 and a Look Forward to 2009
Molecules 2009, 14(1), 584-585; https://doi.org/10.3390/molecules14010584
Received: 3 January 2009 / Published: 23 January 2009
Cited by 1 | PDF Full-text (128 KB) | HTML Full-text | XML Full-text
Abstract
As has now become a custom for Molecules, as one year ends and another starts its Publisher and Editor-in-Chief would like to take stock of our progress in 2008 and offer our readership a preview of things to come in 2009. Just as
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As has now become a custom for Molecules, as one year ends and another starts its Publisher and Editor-in-Chief would like to take stock of our progress in 2008 and offer our readership a preview of things to come in 2009. Just as we had hoped in last year’s editorial [1], the year that just concluded proved to be another outstanding one for MDPI's flagship journal Molecules. By year’s end we had published 239 papers and three Editorials or Editor's Notes for a total of 3,252 pages. While the 8% growth in the number of papers published compared to 2007 may appear modest, the number of pages published represented a 22% increase over the prior year, and was largely attributable to the increase in the number of reviews published. [...] Full article
Open AccessArticle Antiosteoporotic Activity of Anthraquinones from Morinda officinalis on Osteoblasts and Osteoclasts
Molecules 2009, 14(1), 573-583; https://doi.org/10.3390/molecules14010573
Received: 16 December 2008 / Revised: 17 January 2009 / Accepted: 22 January 2009 / Published: 23 January 2009
Cited by 53 | PDF Full-text (215 KB) | HTML Full-text | XML Full-text
Abstract
Bioactivity-guided fractionation led to the successful isolation of antiosteoporotic components, i.e. physicion (1), rubiadin-1-methyl ether (2), 2-hydroxy-1-methoxy- anthraquinone (3), 1,2-dihydroxy-3-methylanthraquinone (4), 1,3,8-trihydroxy-2-methoxy- anthraquinone (5), 2-hydroxymethyl-3-hydroxyanthraquinone (6), 2-methoxyanthraquinone (7) and scopoletin (8) from an ethanolic extract of the roots of Morinda officinalis. Compounds
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Bioactivity-guided fractionation led to the successful isolation of antiosteoporotic components, i.e. physicion (1), rubiadin-1-methyl ether (2), 2-hydroxy-1-methoxy- anthraquinone (3), 1,2-dihydroxy-3-methylanthraquinone (4), 1,3,8-trihydroxy-2-methoxy- anthraquinone (5), 2-hydroxymethyl-3-hydroxyanthraquinone (6), 2-methoxyanthraquinone (7) and scopoletin (8) from an ethanolic extract of the roots of Morinda officinalis. Compounds 4-8 are isolated for the first time from M. officinalis. Among them, compounds 2 and 3 promoted osteoblast proliferation, while compounds 4, 5 increased osteoblast ALP activity. All of the isolated compounds inhibited osteoclast TRAP activity and bone resorption, and the inhibitory effects on osteoclastic bone resorption of compounds 1 and 5 were stronger than that of other compounds. Taken together, antiosteoporotic activity of M. officinalis and its anthraquinones suggest therapeutic potential against osteoporosis. Full article
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Open AccessCommunication Rubiacordone A: A New Anthraquinone Glycoside from the Roots of Rubia cordifolia
Molecules 2009, 14(1), 566-572; https://doi.org/10.3390/molecules14010566
Received: 20 November 2008 / Revised: 13 January 2009 / Accepted: 15 January 2009 / Published: 23 January 2009
Cited by 18 | PDF Full-text (196 KB) | HTML Full-text | XML Full-text
Abstract
A new anthraquinone, Rubiacordone A (1) (6-acetoxy-1-hydroxy-2-methylanthraquinone-3-O-α-L-rhamnopyranoside), was isolated together with the known anthraquinone, 1-acetoxy-6-hydroxy-2-methylanthraquinone-3-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside] (2), from the dried roots of Rubia cordifolia. Their structures were
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A new anthraquinone, Rubiacordone A (1) (6-acetoxy-1-hydroxy-2-methylanthraquinone-3-O-α-L-rhamnopyranoside), was isolated together with the known anthraquinone, 1-acetoxy-6-hydroxy-2-methylanthraquinone-3-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside] (2), from the dried roots of Rubia cordifolia. Their structures were elucidated on the basis of extensive 1D and 2D-NMR, as well as HRESI-MS spectroscopic analysis. Metabolites 1 and 2 showed considerable antimicrobial activity against Gram-positive bacteria. Full article
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Open AccessArticle Optimization and Comparison of Five Methods for Extraction of Coniferyl Ferulate from Angelica sinensis
Molecules 2009, 14(1), 555-565; https://doi.org/10.3390/molecules14010555
Received: 15 November 2008 / Revised: 15 January 2009 / Accepted: 19 January 2009 / Published: 23 January 2009
Cited by 22 | PDF Full-text (555 KB) | HTML Full-text | XML Full-text
Abstract
Coniferyl ferulate, which is noted for its multiple pharmacological activities and chemical instability, is abundant in Angelica sinensis. In this paper, five methods, namely sonication extraction (SE), pressurized liquid extraction (PLE), supercritical fluid extraction (SFE), hydrodistillation (HD) and decoction (DC) for extraction
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Coniferyl ferulate, which is noted for its multiple pharmacological activities and chemical instability, is abundant in Angelica sinensis. In this paper, five methods, namely sonication extraction (SE), pressurized liquid extraction (PLE), supercritical fluid extraction (SFE), hydrodistillation (HD) and decoction (DC) for extraction of coniferyl ferulate, as well as ferulic acid, Z/E-ligustilide and Z/E-butylidenephthalide, from A. sinensis were optimized and compared. The results showed that the order of extraction efficiency was: PLE»SE>SFE>>HD, DC. The compositions of the SE, PLE and SFE extracts, which had a high ratio of coniferyl ferulate, were very similar, while no coniferyl ferulate was obtained by HD and DC, though they had high selectivity for the extraction of ligustilide and ferulic acid, respectively. It was noteworthy that the content of ligustilide and coniferyl ferulate was not detectable in the decoction, the commonly used oral administration form of Traditional Chinese Medicines in clinical practice. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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Open AccessReview Biological and Pharmacological Activities of Squalene and Related Compounds: Potential Uses in Cosmetic Dermatology
Molecules 2009, 14(1), 540-554; https://doi.org/10.3390/molecules14010540
Received: 8 January 2009 / Revised: 19 January 2009 / Accepted: 21 January 2009 / Published: 23 January 2009
Cited by 120 | PDF Full-text (466 KB) | HTML Full-text | XML Full-text
Abstract
Squalene is a triterpene that is an intermediate in the cholesterol biosynthesis pathway. It was so named because of its occurrence in shark liver oil, which contains large quantities and is considered its richest source. However, it is widely distributed in nature, with
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Squalene is a triterpene that is an intermediate in the cholesterol biosynthesis pathway. It was so named because of its occurrence in shark liver oil, which contains large quantities and is considered its richest source. However, it is widely distributed in nature, with reasonable amounts found in olive oil, palm oil, wheat-germ oil, amaranth oil, and rice bran oil. Squalene, the main component of skin surface polyunsaturated lipids, shows some advantages for the skin as an emollient and antioxidant, and for hydration and its antitumor activities. It is also used as a material in topically applied vehicles such as lipid emulsions and nanostructured lipid carriers (NLCs). Substances related to squalene, including β-carotene, coenzyme Q10 (ubiquinone) and vitamins A, E, and K, are also included in this review article to introduce their benefits to skin physiology. We summarize investigations performed in previous reports from both in vitro and in vivo models. Full article
(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)
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Open AccessCommunication “Flash” Solvent-free Synthesis of Triazoles Using a Supported Catalyst
Molecules 2009, 14(1), 528-539; https://doi.org/10.3390/molecules14010528
Received: 8 January 2009 / Revised: 20 January 2009 / Accepted: 22 January 2009 / Published: 22 January 2009
Cited by 25 | PDF Full-text (231 KB) | HTML Full-text | XML Full-text
Abstract
A solvent-free synthesis of 1,4-disubstituted-1,2,3-triazoles using neat azides and alkynes and a copper(I) polymer supported catalyst (Amberlyst® A21•CuI) is presented herein. As it provides the products in high yields and purities within minutes, this method thus being characterized as a "flash" synthesis,
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A solvent-free synthesis of 1,4-disubstituted-1,2,3-triazoles using neat azides and alkynes and a copper(I) polymer supported catalyst (Amberlyst® A21•CuI) is presented herein. As it provides the products in high yields and purities within minutes, this method thus being characterized as a "flash" synthesis, and was exemplified through the synthesis of a 24-compound library on a small scale. Full article
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Open AccessArticle Antimicrobial Activity of Some Thiourea Derivatives and Their Nickel and Copper Complexes
Molecules 2009, 14(1), 519-527; https://doi.org/10.3390/molecules14010519
Received: 2 December 2008 / Revised: 24 December 2008 / Accepted: 5 January 2009 / Published: 22 January 2009
Cited by 93 | PDF Full-text (151 KB) | HTML Full-text | XML Full-text
Abstract
Five thiourea derivative ligands and their Ni2+ and Cu2+ complexes have been synthesized. The compounds were screened for their in vitro anti-bacterial activity using Gram-positive bacteria (two different standard strains of Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Streptococcus
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Five thiourea derivative ligands and their Ni2+ and Cu2+ complexes have been synthesized. The compounds were screened for their in vitro anti-bacterial activity using Gram-positive bacteria (two different standard strains of Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Streptococcus pyogenes, Bacillus cereus) and Gram-negative bacteria (Esherichia coli, Pseudomonas aeruginosa, Enterobacter cloacae, Proteus vulgaris, Enterobacter aerogenes) and in vitro anti-yeast activity (Candida albicans, Candida krusei, Candida glabrata, Candida tropicalis, Candida parapsilosis). The minimum inhibitory concentration was determined for all ligands and their complexes. In vitro anti-yeast activity of both ligands and their metal complexes is greater than their in vitro anti-bacterial activity. The effect of the structure of the investigated compounds on the antimicrobial activity is discussed. Full article
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Open AccessArticle Antimutagenic Activity and Radical Scavenging Activity of Water Infusions and Phenolics from Ligustrum Plants Leaves
Molecules 2009, 14(1), 509-518; https://doi.org/10.3390/molecules14010509
Received: 24 November 2008 / Revised: 15 January 2009 / Accepted: 21 January 2009 / Published: 22 January 2009
Cited by 31 | PDF Full-text (230 KB) | HTML Full-text | XML Full-text
Abstract
Water infusions of Ligustrum delavayanum and Ligustrum vulgare leaves and eight phenolics isolated therefrom have been assayed in vitro on ofloxacin-induced genotoxicity in the unicellular flagellate Euglena gracilis. The tested compounds luteolin, quercetin, luteolin-7-glucoside, luteolin-7-rutinoside, quercetin-3-rutinoside, apigenin-7-rutinoside, tyrosol and esculetin inhibited the
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Water infusions of Ligustrum delavayanum and Ligustrum vulgare leaves and eight phenolics isolated therefrom have been assayed in vitro on ofloxacin-induced genotoxicity in the unicellular flagellate Euglena gracilis. The tested compounds luteolin, quercetin, luteolin-7-glucoside, luteolin-7-rutinoside, quercetin-3-rutinoside, apigenin-7-rutinoside, tyrosol and esculetin inhibited the mutagenic activity of ofloxacin (43 µM) in E. gracilis. Water infusions from leaves of L. delavayanum and L. vulgare showed higher antimutagenic effect (pt < 0.001). The activity of these samples against ofloxacin (86 µM)-induced genotoxicity was lower, but statistically significant (pt < 0.05), excluding the water infusion of L. delavayanum leaves (pt < 0.01). Efficacy of quercetin, luteolin-7-rutinoside, apigenin-7-rutinoside was insignificant. The antimutagenic effect of most phenolics we studied could be clearly ascribed to their DPPH scavenging activity, substitution patterns and lipophilicity. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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Open AccessArticle 2-Amido-3-(1H-Indol-3-yl)-N-Substitued-Propanamides as a New Class of Falcipain-2 Inhibitors. 1. Design, Synthesis, Biological Evaluation and Binding Model Studies
Molecules 2009, 14(1), 494-508; https://doi.org/10.3390/molecules14010494
Received: 7 December 2008 / Revised: 11 January 2009 / Accepted: 13 January 2009 / Published: 21 January 2009
Cited by 9 | PDF Full-text (420 KB) | HTML Full-text | XML Full-text
Abstract
The Plasmodium falciparum cysteine protease falcipain-2 (FP-2) is an important cysteine protease and an essential hemoglobinase of erythrocytic P. falciparum trophozoites. The discovery of new FP-2 inhibitors is now a hot topic in the search for potential malaria treatments. In this study, a
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The Plasmodium falciparum cysteine protease falcipain-2 (FP-2) is an important cysteine protease and an essential hemoglobinase of erythrocytic P. falciparum trophozoites. The discovery of new FP-2 inhibitors is now a hot topic in the search for potential malaria treatments. In this study, a series of novel small molecule FP-2 inhibitors have been designed and synthesized based on three regional optimizations of the lead (R)-2-phenoxycarboxamido-3-(1H-indol-3-yl)-N-benzylpropanamide(1), which was identified using structure-based virtual screening in conjunction with surface plasmon resonance (SPR)-based binding assays. Four compounds – 1, 2b, 2k and 2l –showed moderate FP-2 inhibition activity, with IC50 values of 10.0-39.4 μM, and the inhibitory activityof compound 2k was ~3-fold better than that of the prototype compound 1 and may prove useful for the development of micromolar level FP-2 inhibitors. Preliminary SAR data was obtained, while molecular modeling revealed that introduction of H-bond donor or/and acceptor atoms to the phenyl ring moiety in the C region would be likely to produce some additional H-bond interactions, which should consequently enhance molecular bioactivity. Full article
(This article belongs to the Special Issue Neglected Diseases: Medicinal Chemistry and Natural Product Chemistry)
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Open AccessArticle Total Antioxidant Capacity of Some Commercial Fruit Juices: Electrochemical and Spectrophotometrical Approaches
Molecules 2009, 14(1), 480-493; https://doi.org/10.3390/molecules14010480
Received: 26 November 2008 / Revised: 26 December 2008 / Accepted: 14 January 2009 / Published: 20 January 2009
Cited by 58 | PDF Full-text (324 KB) | HTML Full-text | XML Full-text
Abstract
The aim of this paper was to assess the total antioxidant capacity of some commercial fruit juices (namely citrus), spectrophotometrically and by the biamperometric method, using the redox couple DPPH· (2,2-diphenyl-1-picrylhydrazyl)/DPPH (2,2-diphenyl-1-picrylhydrazine). Trolox® was chosen as a standard antioxidant. In the case
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The aim of this paper was to assess the total antioxidant capacity of some commercial fruit juices (namely citrus), spectrophotometrically and by the biamperometric method, using the redox couple DPPH· (2,2-diphenyl-1-picrylhydrazyl)/DPPH (2,2-diphenyl-1-picrylhydrazine). Trolox® was chosen as a standard antioxidant. In the case of the spectrophometric method, the absorbance decrease of the DPPH· solution was followed. For the biamperometric method, the influence of some parameters like the potential diference, ΔE, DPPH· concentration, and Trolox® concentration was investigated. The calibration graph obtained for Trolox® presents linearity between 5 and 30 µM, (y = 0.059 x + 0.0564, where y represents the value of current intensity, expressed as μA and x the value of Trolox® concentration, expressed as μM; r2 = 0.9944). The R.S.D. value for the biamperometric method was 1.29% (n = 10, c = 15 μM Trolox®). In the case of the spectrophotometric method, the calibration graph obtained for Trolox® presents linearity between 0.01 and 0.125 mM (y = -9.5789 x+1.4533, where y represents the value of absorbance and x, the value of Trolox® concentration, expressed as mM; r2 = 0.9963). The R.S.D. value for the spectrophotometric method was 2.05%. Both methods were applied to total antioxidant activity determination in real samples (natural juices and soft drinks) and the results were in good agreement. Full article
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Open AccessArticle Mechanochemical Solvent-Free and Catalyst-Free One-Pot Synthesis of Pyrano[2,3-d]Pyrimidine-2,4(1H,3H)-Diones with Quantitative Yields
Molecules 2009, 14(1), 474-479; https://doi.org/10.3390/molecules14010474
Received: 26 November 2008 / Revised: 13 January 2009 / Accepted: 14 January 2009 / Published: 19 January 2009
Cited by 70 | PDF Full-text (50 KB) | HTML Full-text | XML Full-text
Abstract
Solvent-free synthesis of pyrano[2,3-d]pyrimidine-2,4(1H,3H)-diones by ball-milling and without any catalyst is described. This method provides several advantages such as being environmentally friendly, using a simple workup procedure, and affording high yields. Full article
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Open AccessReview Phenolics: Occurrence and Immunochemical Detection in Environment and Food
Molecules 2009, 14(1), 439-473; https://doi.org/10.3390/molecules14010439
Received: 30 November 2008 / Revised: 6 January 2009 / Accepted: 12 January 2009 / Published: 19 January 2009
Cited by 23 | PDF Full-text (311 KB) | HTML Full-text | XML Full-text | Correction | Supplementary Files
Abstract
Phenolic compounds may be of natural or anthropogenic origin and be present in the environment as well as in food. They comprise a large and diverse group of compounds that may be either beneficial or harmful for consumers. In this review first a
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Phenolic compounds may be of natural or anthropogenic origin and be present in the environment as well as in food. They comprise a large and diverse group of compounds that may be either beneficial or harmful for consumers. In this review first a non-exhausting overview of interesting phenolics is given, in particular with regards to their presence in environment and food. For some of these compounds, beneficial, toxicological and/or optionally endocrine disrupting activities will be presented. Further, immunochemical detection and/or isolation methods developed will be discussed, including advantages and disadvantages thereof in comparison with conventional analytical methods such as HPLC, GC, MS. A short overview of new sensor-like methods will also be included for present and future application. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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Open AccessReview Multiscale Modeling of Dendrimers and Their Interactions with Bilayers and Polyelectrolytes
Molecules 2009, 14(1), 423-438; https://doi.org/10.3390/molecules14010423
Received: 10 December 2008 / Revised: 3 January 2009 / Accepted: 16 January 2009 / Published: 19 January 2009
Cited by 73 | PDF Full-text (765 KB) | HTML Full-text | XML Full-text
Abstract
Recent advances in molecular dynamics simulation methodologies and computational power have allowed accurate predictions of dendrimer size, shape, and interactions with bilayers and polyelectrolytes with modest computational effort. Atomistic and coarse-grained (CG) models show strong interactions of cationic dendrimers with lipid bilayers. The
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Recent advances in molecular dynamics simulation methodologies and computational power have allowed accurate predictions of dendrimer size, shape, and interactions with bilayers and polyelectrolytes with modest computational effort. Atomistic and coarse-grained (CG) models show strong interactions of cationic dendrimers with lipid bilayers. The CG simulations with explicit lipid and water capture bilayer penetration and pore formation, showing that pore formation is enhanced at high dendrimer concentration, but suppressed at low temperature and high salt concentration, in agreement with experiments. Cationic linear polymers have also been simulated, but do not perforate membranes, evidently because by deforming into a pancake, the charges on a linear polymer achieve intimate contact with a single bilayer leaflet. The relatively rigid dendrimers, on the other hand, penetrate the bilayer, because only by interacting with both leaflets can they achieve a similar degree of contact between charged groups. Also, a “dendrimer-filled vesicle” structure for the dendrimer-membrane interaction is predicted by mesoscale thermodynamic simulations, in agreement with a picture derived from experimental observations. In simulations of complexes of dendrimer and polyelectrolyte, anionic linear chains wrap around the cationic dendrimer and penetrate inside it. Overall, these new results indicate that simulations can now provide predictions in excellent agreement with experimental observations, and provide atomic-scale insights into dendrimer structure and dynamics. Full article
(This article belongs to the Special Issue Dendrimers - from Synthesis to Applications)
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Open AccessCommunication A New Atisane-Type Diterpene from the Bark of the Mangrove Plant Excoecaria Agallocha
Molecules 2009, 14(1), 414-422; https://doi.org/10.3390/molecules14010414
Received: 26 October 2008 / Revised: 13 January 2009 / Accepted: 15 January 2009 / Published: 16 January 2009
Cited by 14 | PDF Full-text (188 KB) | HTML Full-text | XML Full-text
Abstract
A new atisane-type diterpene, ent-16α-hydroxy-atisane-3,4-lactone (4) and three known diterpenes, ent-16α-hydroxy-atisane-3-one (1), ent-atisane-3β,16α-diol (2), ent-3,4-seco-16α-hydroxyatis- 4(19)-en -3-oic acid (3) were isolated from the bark of the mangrove plant Excoecaria agallocha. Their structures and relative stereochemistry were elucidated by
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A new atisane-type diterpene, ent-16α-hydroxy-atisane-3,4-lactone (4) and three known diterpenes, ent-16α-hydroxy-atisane-3-one (1), ent-atisane-3β,16α-diol (2), ent-3,4-seco-16α-hydroxyatis- 4(19)-en -3-oic acid (3) were isolated from the bark of the mangrove plant Excoecaria agallocha. Their structures and relative stereochemistry were elucidated by means of extensive NMR and MS analysis. Compound 3 exhibited significant anti-microfouling activity against the adherence of Pseudomonas pseudoalcaligenes, with an EC50 value of 0.54 ± 0.01 ppm. Full article
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Open AccessCorrection Correction: Wang, Z.-N., et al. A New Cytotoxic Pregnanone from Calotropis gigantean. Molecules 2008, 13, 3033-3039.
Molecules 2009, 14(1), 412-413; https://doi.org/10.3390/molecules14010412
Received: 14 January 2009 / Published: 15 January 2009
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