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Sclareol

$52

  • Brand : BIOFRON

  • Catalogue Number : BD-D1234

  • Specification : 98%(HPLC)

  • CAS number : 515-03-7

  • Formula : C20H36O2

  • Molecular Weight : 308.5

  • PUBCHEM ID : 163263

  • Volume : 20MG

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Catalogue Number

BD-D1234

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

308.5

Appearance

White crystalline powder

Botanical Source

Erilla frutescens (L.) Britt./Salvia sclarea. Also from Salvia schimperi, Cistus creticus, Juniperus excelsa and Nicotiana glutinosa

Structure Type

Sesquiterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(CCCC2(C1CCC(C2CCC(C)(C=C)O)(C)O)C)C

Synonyms

(1R,2R,4aS,8aS)-1-[(3R)-3-Hydroxy-3-methyl-4-penten-1-yl]-2,5,5,8a-tetramethyldecahydro-2-naphthalenol/(1R,2R,4aS,8aS)-1-[(3R)-3-Hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol/SCLAREOL(RG)/1-Naphthalenepropanol, α-ethenyldecahydro-2-hydroxy-α,2,5,5,8a-pentamethyl-, (αR,1R,2R,4aS,8aS)-/Labd-14-ene-8,13-diol, (13R)-/SCIADONIC ACID/(1R,2R,8aS)-Decahydro-1-(3-hydroxy-3-methyl-4-pentenyl)-2,5,5,8a-tetramethyl-2-naphthol/labd-14-ene-8,13(R)-diol/SCLAREOL,NATURAL/SCAREOL/Sclareol/(-)-sclareol/SCLAREOL(P)/(1R,2R,4aS,8aS)-1-[(3R)-3-Hydroxy-3-methyl-4-penten-1-yl]-2,5,5,8a-tetramethyldecahydro-2-naphtalenol

IUPAC Name

(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol

Applications

Density

1.0±0.1 g/cm3

Solubility

Chloroform; Ethyl Acetate

Flash Point

169.1±15.0 °C

Boiling Point

398.3±15.0 °C at 760 mmHg

Melting Point

95-100 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2906190000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:515-03-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31549110

Abstract

Postmenopausal osteoporosis (PMO) is a progressive disease occurring in elderly postmenopausal women that is characterized by low bone mass and impaired bone quality. Sclareol is a natural product (initially isolated from the leaves and flowers of Salvia Sclarea) that possesses immune-regulation and anti-inflammatory effects, but its role in osteoclastic formation and function as well as the PMO remains unknown. In the current study, we investigated the inhibitory effect of sclareol on osteoclastogenesis and progression of PMO. In vitro, sclareol not only inhibited osteoclast formation but also suppressed osteoclast function. The expression of the receptor activator of NF-κB ligand (RANKL)-induced osteoclast marker gene and protein was also reduced by sclareol treatment. Mechanistically, we found that sclareol inhibits RANKL-induced NF-κB and MAPK/ERK pathway activation. Furthermore, sclareol exerted a protective effect against bone loss in an ovariectomy-induced mouse model. Taken together, our findings suggest that sclareol has potential value as a therapeutic agent for PMO.

Title

Sclareol prevents ovariectomy-induced bone loss in vivo and inhibits osteoclastogenesis in vitro via suppressing NF-κB and MAPK/ERK signaling pathways

Author

Jin H 1, Shao Z , Wang Q , Miao J , Bai X , Liu Q , Qiu H , Wang C , Zhang Z , Jennifer T , Wang X , Xu J .

Publish date

2019 Oct 16

PMID

31474477

Abstract

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.

KEYWORDS

Antispirochaetal activity; Borrelia burgdorferi s.s.; Carvacrol; Cistus creticus L.; Epi-manoyloxide; Labdanum

Title

Labdanum and Labdanes of Cistus creticus and C. ladanifer: Anti-Borrelia activity and its phytochemical profiling✰.

Author

Rauwald HW1, Liebold T2, Grotzinger K2, Lehmann J3, Kuchta K2.

Publish date

2019 Jul

PMID

31344429

Abstract

AIMS:
In this work, it was sought to determine if there was synergism between doxorubicin (DOX), a well-known antineoplastic, and sclareol (SC), a diterpene from natural origin, in breast cancer treatment. Moreover, it was investigated if their co-loading in the same nanocarrier would result in a gain of activity and/or a toxicity diminishment.

MAIN METHODS:
The synergism of the DOX:SC combination was evaluated in MDA-MB-231 and 4T1 cells. A nanostructured lipid carrier (NLC) co-encapsulating DOX and SC in their synergistic molar ratio was prepared and characterised, in terms of mean diameter, zeta potential, DOX encapsulation efficiency, small angle X-ray scattering, differential scanning calorimetry, and polarised light microscopy for further intravenous administration. The anticancer activity of the combination, free and encapsulated, was evaluated in 4T1-tumour bearing mice.

KEY FINDINGS:
It was determined that DOX:SC combination at the molar ratio 1:1.9 presents better synergistic anticancer activity than the molar ratio 1:7.5 in vitro. DOX:SC-loaded NLC (NLC-DOX-SC) improved in vitro cytotoxic and in vivo antitumour activity compared to free DOX. Although NLC-DOX-SC and free DOX:SC, at the synergistic molar ratio, showed similar activity in the in vivo study, the free combination provoked body weight loss, behaviour alterations and haematological toxicity in the animals, while this was not observed for NLC-DOX-SC.

SIGNIFICANCE:
This work shows that SC and DOX present synergistic anticancer activity for breast cancer treatment whereas NLC-DOX-SC was a feasible alternative to attain the benefits posed by DOX:SC combination but with none to fewer side effects.

Copyright © 2019 Elsevier Inc. All rights reserved.

KEYWORDS

Breast cancer; Co-encapsulation; Doxorubicin; Nanostructured lipid carriers; Sclareol; Synergism

Title

Sclareol is a potent enhancer of doxorubicin: Evaluation of the free combination and co-loaded nanostructured lipid carriers against breast cancer.

Author

Borges GSM1, Silva JO1, Fernandes RS1, de Souza aM2, Cassali GD3, Yoshida MI4, Leite EA1, de Barros ALB5, Ferreira LAM6.

Publish date

2019 Sep 1