Lup-20(29)-en-28-ol-3-one (betulone).

Published on May 1, 2013in Acta Crystallographica Section E-structure Reports Online
· DOI :10.1107/S1600536813011008
Stanisław Boryczka16
Estimated H-index: 16
(Medical University of Silesia),
Ewa Michalik5
Estimated H-index: 5
(Wrocław Medical University)
+ 2 AuthorsElwira Chrobak11
Estimated H-index: 11
(Medical University of Silesia)
Sources
Abstract
The asymmetric unit of the title compound, C30H48O2, contains two independent mol­ecules, the main difference between them being that the isopropenyl group is rotated by approximately 180°. In each mol­ecule, the fused six-membered rings have chair–chair–chair–chair conformations and the cyclo­pentane ring adopts an envelope conformation with the C atom bearing the hy­droxy­methyl group as the flap. All ring junctions are trans-fused. With the exception of one of the methyl groups adjacent to the C=O group, all the methyl groups are in axial positions. The isopropenyl group is equatorial and the hy­droxy­methyl group is in an axial orientation. In the crystal, weak C—H⋯O inter­actions link the mol­ecules into chains along [010]. Weak intra­molecular C—H⋯O hydrogen bonds are also observed but the hy­droxy groups are not involved in hydrogen bonds.
References17
Newest
#1Stanisław Boryczka (Medical University of Silesia)H-Index: 16
#2Maria Jastrzebska (University of Silesia in Katowice)H-Index: 15
Last. Ewa Michalik (Medical University of Silesia)H-Index: 5
view all 7 authors...
ABSTRACT X-ray diffraction and infrared spectroscopy measurements for the N,N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) solvatomorphs of betulonic acid (BA) were investigated. BA [3-oxolup-20(29)-en-28-oic acid, C 30 H 46 O 3 ] exhibits a wide spectrum of biological activities and is considered to be a promising natural agent for the treatment of various cancer diseases. BA as a noncrystalline substance was obtained by oxidation of betulin. Crystal structures and the spectral data al...
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#1Stanisław BoryczkaH-Index: 16
#2Ewa BębenekH-Index: 11
Last. Maciej ZubkoH-Index: 13
view all 5 authors...
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AbstractBetulin is a lupane triterpenoid [lup-20(29)-ene-3β,28-diol, C 30 H 50 O 2 ] showing high biological activity. This activity is supposed to be strongly affected by the molecular structure of its polymorphic forms. Different solvate polymorphic forms of betulin have aroused increasing interest as the possible anticancer agents of natural origin. X-ray diffraction was used to investigate crystal structure of (1:1) betulin–DMSO solvate. Title compound crystallizes in the orthorhombic P2 1 2...
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#1Tatiana N. Drebushchak (NSU: Novosibirsk State University)H-Index: 16
#2M. A. Mikhailenko (NSU: Novosibirsk State University)H-Index: 10
Last. Svetlana A. Kuznetsova (RAS: Russian Academy of Sciences)H-Index: 12
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The crystal structure of the 1:1 ethanol betulin solvate, a widely spread natural compound, is determined. The betulin solvate crystallizes in orthorhombic symmetry in the P212121 space group, Z= 4. The unit cell parameters are as follows: a = 7.0159(1) A, b = 12.4425(2) A, c = 33.7500(5) A; V = 2946.22(8) A3. Betulin molecules are hydrogen bonded to each other and ethanol molecules, as a result of which the layers are distinguished in the structure, which are perpendicular to the crystallograph...
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publCIF is an application designed for creating, editing and validating crystallographic information files (CIFs) that are used in journal publication. It validates syntax and dictionary-defined data attributes through internal routines, and also provides a web interface to the checkCIF service of the International Union of Crystallography (IUCr), which provides a full crystallographic analysis of the structural data. The graphical interface allows users to edit the CIF either in its `raw' ASCII...
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#1Sami Alakurtti (VTT Technical Research Centre of Finland)H-Index: 15
#2Pia Bergström (VTT Technical Research Centre of Finland)H-Index: 1
Last. Jari Yli-Kauhaluoma (UH: University of Helsinki)H-Index: 36
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Leishmanicidal activity of 24 derivatives of naturally occurring and abundant triterpenes belonging to the lupane series, betulin, betulinic acid and betulonic acid, is described in this study. The easily modified positions of the lupane skeleton, the hydroxy groups of C-3 and C-28, as well as the carbon-carbon double bond C-20-C-29 were used as a starting point to prepare a library of triterpenoid derivatives for bioactivity studies. The compounds were evaluated against Leishmania donovani axen...
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#1Papa Niokhor Diouf (Laval University)H-Index: 16
#2Tatjana Stevanovic (Laval University)H-Index: 22
Last. Yvan Boutin (Laval University)H-Index: 12
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Abstract Crude ethanol extracts from different tissues of Betula alleghaniensis: wood, inner and outer bark, foliage, and twigs were evaluated for their nitric oxide (NO)-radical scavenging activities and inhibitory effects on the production of NO in LPS/INFγ-stimulated RAW 264.7 macrophages. As a renewed interest in plant-derived drugs has led to an increased need for efficient extraction methods, ultrasonic-assisted extraction (UAE) was investigated and compared with conventional maceration. T...
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In the title mol­ecule, C34H53BrO4, all the cyclo­hexane rings adopt chair conformations, while the cyclo­pentane ring adopts an envelope conformation. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into corrugated sheets parallel to the ab plane.
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#1George M. Sheldrick (GAU: University of Göttingen)H-Index: 71
An account is given of the development of the SHELX system of computer programs from SHELX-76 to the present day. In addition to identifying useful innovations that have come into general use through their implementation in SHELX, a critical analysis is presented of the less-successful features, missed opportunities and desirable improvements for future releases of the software. An attempt is made to understand how a program originally designed for photographic intensity data, punched cards and ...
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#1Clare F. Macrae (University of Cambridge)H-Index: 9
#2Paul R. Edgington (University of Cambridge)H-Index: 4
Last. Jacco van de Streek (University of Cambridge)H-Index: 25
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Since its original release, the popular crystal structure visualization program Mercury has undergone continuous further development. Comparisons between crystal structures are facilitated by the ability to display multiple structures simultaneously and to overlay them. Improvements have been made to many aspects of the visual display, including the addition of depth cueing, and highly customizable lighting and background effects. Textual and numeric data associated with structures can be shown ...
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Cited By4
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#1V. A. Vydrina (RAS: Russian Academy of Sciences)H-Index: 6
#2R. R. Sayakhov (RAS: Russian Academy of Sciences)H-Index: 1
Last. G. Yu. Ishmuratov (RAS: Russian Academy of Sciences)H-Index: 12
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A new synthesis of 3-oxo-28-hydroxylup-20(29)-ene from the available natural triterpenoid betulin was developed. α,ω-Diketodiesters were prepared for the first time by different methods from 3-oxo-28-hydroxylup-20(29)-ene and a series of natural dicarboxylic acids. Steglich reaction conditions gave the highest yields. One of the synthesized α,ω-diketodiesters was moderately active in vitro against A-549 lung carcinoma.
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#1Ewa Bębenek (University of Silesia in Katowice)H-Index: 11
#2Monika Kadela-Tomanek (University of Silesia in Katowice)H-Index: 10
Last. Stanisław Boryczka (University of Silesia in Katowice)H-Index: 16
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Betulin 1 and its semisynthetic derivatives exhibit a cytotoxic activity toward various cancer cell lines. These compounds are a promising and potential anticancer candidates. A series of betulin derivatives was prepared and tested for the antiproliferative activity in vitro against T47D breast cancer, CCRF/CEM leukemia, HL-60 promyelocytic leukemia, SW707 colorectal, murine P388 leukemia, as well as BALB3T3 normal fibroblasts cell lines. Cisplatin and betulin 1 were used as a reference compound...
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#1Elwira Chrobak (Medical University of Silesia)H-Index: 11
#2Ewa Michalik (Wrocław Medical University)H-Index: 5
Last. Stanisław Boryczka (Medical University of Silesia)H-Index: 16
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The lupane triterpenoid betulonic aldehyde [also known as betulonal; systematic name: lup-20(29)-en-28-al-3-one, C30H46O2] is a product of betulin oxidation. Crystals were obtained from hexane [form (I)] and dimethyl sulfoxide [form (II)] solutions. Forms (I) and (II) are both ortho­rhom­bic. The molecular geometric parameters in the two forms are similar, but the structures are different with respect to the crystal packing. Polymorph (I) contains two independent mol­ecules in the asymmetric uni...
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#1Shagufta Perveen (KSU: King Saud University)H-Index: 14
#2Nawal M. Al-Musayeib (KSU: King Saud University)H-Index: 15
Two new sphingolipid glucosides, odoraside A (1) and odoraside B (2), have been isolated from chloroform-soluble fraction of the total methanolic extract of Klienia odora, together with five known compounds, β-sitosterol (3), oleanolic acid (4), betulone (5), 2,3-dihydroxy-12-oleanen-28-oic acid (6), and β-sitosterol 3-O-β-d-glucopyranoside (7). Their structures were assigned from 1H and 13C NMR spectra, DEPT and by 2D COSY, NOESY, HMQC, and HMBC experiments.
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