دورية أكاديمية
Labdanum and Labdanes of Cistus creticus and C. ladanifer: Anti-Borrelia activity and its phytochemical profiling ✰ .
| العنوان: | Labdanum and Labdanes of Cistus creticus and C. ladanifer: Anti-Borrelia activity and its phytochemical profiling ✰ . |
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| المؤلفون: | Rauwald HW; Department of Pharmaceutical Biology, Institute of Pharmacy, Leipzig University, Johannisallee 21-23, Leipzig 04103, Germany. Electronic address: rauwald@rz.uni-leipzig.de., Liebold T; Department of Pharmaceutical Biology, Institute of Pharmacy, Leipzig University, Johannisallee 21-23, Leipzig 04103, Germany., Grötzinger K; Department of Pharmaceutical Biology, Institute of Pharmacy, Leipzig University, Johannisallee 21-23, Leipzig 04103, Germany., Lehmann J; Department of Therapy Validation, Fraunhofer Institute for Cell Therapy and Immunology, Perlickstr. 1, Leipzig 04103, Germany., Kuchta K; Department of Pharmaceutical Biology, Institute of Pharmacy, Leipzig University, Johannisallee 21-23, Leipzig 04103, Germany. |
| المصدر: | Phytomedicine : international journal of phytotherapy and phytopharmacology [Phytomedicine] 2019 Jul; Vol. 60, pp. 152977. Date of Electronic Publication: 2019 May 31. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: Urban & Fischer Verlag Country of Publication: Germany NLM ID: 9438794 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1618-095X (Electronic) Linking ISSN: 09447113 NLM ISO Abbreviation: Phytomedicine Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Stuttgart : Urban & Fischer Verlag Original Publication: Stuttgart ; New York : G. Fischer, c1994- |
| مواضيع طبية MeSH: | Anti-Bacterial Agents/*pharmacology , Borrelia/*drug effects , Cistus/*chemistry , Diterpenes/*pharmacology, Anti-Bacterial Agents/isolation & purification ; Cymenes ; Diterpenes/isolation & purification ; Gas Chromatography-Mass Spectrometry ; Greece ; Monoterpenes/isolation & purification ; Monoterpenes/pharmacology ; Oils, Volatile/isolation & purification ; Oils, Volatile/pharmacology ; Phytochemicals/isolation & purification ; Phytochemicals/pharmacology ; Plant Extracts/isolation & purification ; Plant Extracts/pharmacology ; Plant Leaves/chemistry ; Terpenes/isolation & purification ; Terpenes/pharmacology |
| مستخلص: | Background: Intrigued by testimonies of Saxon borreliosis self-help groups concerning considerabl improvements of their symptoms by ingestion of Cistus creticus L. (Cistaceae) leaf preparations, we recently reported on the growth inhibiting activity of extracts with different polarities and its volatile oil against Borrelia burgdorferi sensu stricto (Bbss) in vitro, determined by a bioassay guided procedure. The most active volatile oil (only about 0.10% in leaves) was found to be dominated by labdane-type manoyloxides as well as carvacrol, determined via GC-MS. Hypothesis: These terpenes are major active constituents of the old pharmaceutical oleoresin labdanum, which is secreted from the leaf surface of C. creticus and traditionally harvested, e.g., on Crete by brushing the shrubs. Methods: In order to elucidate the definite anti-Borrelia active principles of C. creticus, preparative scale separation of the diethyl‑ether soluble fraction of Cretan labdanum was achieved by combined silica gel 60-and RP-18 CC and analysed by novel TLC-Extractor/ES-MS as well as by 1d/2d-1H/13C-NMR data. For the antispirochaetal activity tests against Bbss in vitro, all samples were solubilised in water with addition of polysorbate 80, the effect of which on bacterial growth was examined and found to be negligible. Results: This led to isolation and identification of the monoterpene carvacrol as well as of the four major manoyloxides manoyloxide (A), 3-acetoxy-manoyloxide (B), 3‑hydroxy-manoyloxide (C), and epi‑manoyloxide (D). Additionally, 2-keto-manoyloxide (E) and sclareol (F) were identified via GC/EI-MS. In subsequent microbiological tests of the isolated compounds, epi‑manoyloxide (D) exhibited by far the strongest individual antispirochaetal effect, equal to the positive control amoxicilline. Furthermore, manoyloxide (A), carvacrol, and the diethyl‑ether soluble fraction of labdanum as a whole contribute to the strong antispirochaetal activity, while the other labdanes were less active. Isolated manoyloxides were further used as external standards for a GC-MS screening of labdanum samples from different origins, revealing exceptionally high contents of all analysed manoyloxides in the samples of Cretan labdanum from C. creticus, while their contents in other commercial available labdanum samples were lower by several orders of magnitude. Especially in Spanish labdanum samples, declared as Cistus ladanifer L., mainly simple alkanes and at most traces of epi‑manoyloxide (D) and of manoyloxide (A) could be detected. Conclusion: The application of C. creticus preparations by Lyme disease self-help groups may be considered as a reasonable therapy approach. For the first time, isolated epi‑manoyloxide and carvacrol could be evaluated as most promising candidates for drug development and labdanum based phytomedicine development, respectively. They should serve as vital active markers for quality assessments of C. creticus preparations. (Copyright © 2019 Elsevier GmbH. All rights reserved.) |
| فهرسة مساهمة: | Keywords: Antispirochaetal activity; Borrelia burgdorferi s.s.; Carvacrol; Cistus creticus L.; Epi-manoyloxide; Labdanum |
| المشرفين على المادة: | 0 (Anti-Bacterial Agents) 0 (Cymenes) 0 (Diterpenes) 0 (Monoterpenes) 0 (Oils, Volatile) 0 (Phytochemicals) 0 (Plant Extracts) 0 (Terpenes) 0 (manoyl oxide) 0 (oleoresins) 9B1J4V995Q (carvacrol) B607NP0Q8Y (sclareol) |
| تواريخ الأحداث: | Date Created: 20190903 Date Completed: 20191120 Latest Revision: 20191210 |
| رمز التحديث: | 20221213 |
| DOI: | 10.1016/j.phymed.2019.152977 |
| PMID: | 31474477 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1618-095X |
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| DOI: | 10.1016/j.phymed.2019.152977 |