Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoid
The title compound, C20H36O2·CH3OH [systematic name: (3S)-4-[(S)-3-hydroxy-3-methylpent-4-en-1-yl]-3,4a,8,8-tetramethyldecahydronaphthalen-3-ol methanol monosolvate], is a methanol solvate of sclareol, a diterpene oil isolated from the medicinally important medicinal herb Salvia sclarea, commonly kn...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2020-03-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989020001474 |
| _version_ | 1828882087261765632 |
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| author | Memoona Bibi M. Iqbal Choudhary Sammer Yousuf |
| author_facet | Memoona Bibi M. Iqbal Choudhary Sammer Yousuf |
| author_sort | Memoona Bibi |
| collection | DOAJ |
| description | The title compound, C20H36O2·CH3OH [systematic name: (3S)-4-[(S)-3-hydroxy-3-methylpent-4-en-1-yl]-3,4a,8,8-tetramethyldecahydronaphthalen-3-ol methanol monosolvate], is a methanol solvate of sclareol, a diterpene oil isolated from the medicinally important medicinal herb Salvia sclarea, commonly known as clary sage. It crystallizes in space group P1 (No. 1) with Z′ = 2. The sclareol molecule comprises two trans-fused cyclohexane rings, each having an equatorially oriented hydroxyl group, and a 3-methylpent-1-en-3-ol side chain. In the crystal, Os—H...Os, Os—H...Om, Om—H...Os and Om—H...Om (s = sclareol, m = methanol) hydrogen bonds connect neighboring molecules into infinite [010] chains. The title compound exhibits weak anti-leishmanial activity (IC50 = 66.4 ± 1.0 µM ml−1) against standard miltefosine (IC50 = 25.8 ± 0.2 µM ml−1). |
| first_indexed | 2024-12-13T10:21:08Z |
| format | Article |
| id | doaj.art-91134caf16844f4f8ad5cc8695143b38 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-13T10:21:08Z |
| publishDate | 2020-03-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-91134caf16844f4f8ad5cc8695143b382022-12-21T23:51:11ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902020-03-0176329429710.1107/S2056989020001474hb7890Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoidMemoona Bibi0M. Iqbal Choudhary1Sammer Yousuf2H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, PakistanH. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, PakistanH. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, PakistanThe title compound, C20H36O2·CH3OH [systematic name: (3S)-4-[(S)-3-hydroxy-3-methylpent-4-en-1-yl]-3,4a,8,8-tetramethyldecahydronaphthalen-3-ol methanol monosolvate], is a methanol solvate of sclareol, a diterpene oil isolated from the medicinally important medicinal herb Salvia sclarea, commonly known as clary sage. It crystallizes in space group P1 (No. 1) with Z′ = 2. The sclareol molecule comprises two trans-fused cyclohexane rings, each having an equatorially oriented hydroxyl group, and a 3-methylpent-1-en-3-ol side chain. In the crystal, Os—H...Os, Os—H...Om, Om—H...Os and Om—H...Om (s = sclareol, m = methanol) hydrogen bonds connect neighboring molecules into infinite [010] chains. The title compound exhibits weak anti-leishmanial activity (IC50 = 66.4 ± 1.0 µM ml−1) against standard miltefosine (IC50 = 25.8 ± 0.2 µM ml−1).http://scripts.iucr.org/cgi-bin/paper?S2056989020001474labdane diterpenesalvia sclarea lclary sagesolvatehirshfeld surface analysisleishmaniasiscrystal structure |
| spellingShingle | Memoona Bibi M. Iqbal Choudhary Sammer Yousuf Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoid Acta Crystallographica Section E: Crystallographic Communications labdane diterpene salvia sclarea l clary sage solvate hirshfeld surface analysis leishmaniasis crystal structure |
| title | Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoid |
| title_full | Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoid |
| title_fullStr | Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoid |
| title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoid |
| title_short | Crystal structure and Hirshfeld surface analysis of the methanol solvate of sclareol, a labdane-type diterpenoid |
| title_sort | crystal structure and hirshfeld surface analysis of the methanol solvate of sclareol a labdane type diterpenoid |
| topic | labdane diterpene salvia sclarea l clary sage solvate hirshfeld surface analysis leishmaniasis crystal structure |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989020001474 |
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