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Sclareolide

$53

  • Brand : BIOFRON

  • Catalogue Number : AV-P12053

  • Specification : 98%

  • CAS number : 564-20-5

  • Formula : C16H26O2

  • Molecular Weight : 250.38

  • PUBCHEM ID : 929262

  • Volume : 25mg

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Catalogue Number

AV-P12053

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

250.38

Appearance

White crystalline powder

Botanical Source

Salvia sclarea L./Found in tobacco, Kyllinga erecta, Salvia sclarea, Cistus ladaniferus and Salvia yosgadensis

Structure Type

Sesquiterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(CCCC2(C1CCC3(C2CC(=O)O3)C)C)C

Synonyms

(3aR,9aS,9bR)-3a,6,6,9a-Tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-one/Naphtho[2,1-b]furan-2(1H)-one, decahydro-3a,6,6,9a-tetramethyl-, (3aR,9aS,9bR)-/(3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e][1]benzofuran-2-one/Sclareolide

IUPAC Name

(3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e][1]benzofuran-2-one

Density

1.0±0.1 g/cm3

Solubility

Chloroform; DMSO

Flash Point

132.4±16.4 °C

Boiling Point

321.4±10.0 °C at 760 mmHg

Melting Point

124-126ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:564-20-5) 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

28259943

Abstract

Pancreatic cancer is a type of cancer, which rapidly develops resistance to chemotherapy. Gemcitabine is the treatment used clinically, however, gemcitabine resistance leads to limited efficacy and patient survival rates of only a few months following diagnosis. The aim of the present study was to investigate the mechanisms underlying gemcitabine resistance in pancreatic cancer and to select targeted agents combined with gemcitabine to promote the treatment of pancreatic cancer. Panc?1 and ASPC?1 human pancreatic cancer cells (HPCCs) were used to establish the experimental model, and HPCCs were exposed to gemcitabine of serially increased concentrations to generate gemcitabine?resistant cells (GR?HPCCs). The anticancer effect of gemcitabine combined with sclareolide was then assessed. Epithelial to mesenchymal transition (EMT), human equilibrative nucleoside transporter 1 (hENT1) and ribonucleoside diphosphate reductase 1 (RRM1) were detected in the HPCCs and GR?HPCCs, and the mechanisms were investigated. Sclareolide resensitized the GR?HPCCs to gemcitabine. The expression levels of hENT1 and RRM1 were lower and higher, respectively, in GR?HPCCs, compared with HPCCs. Sclareolide upregulated hENT1, downregulated RRM1 and inhibited gemcitabine?induced EMT through the TWIST1/Slug pathway in the GR?HPCCs. In addition, sclareolide mediated the NOTCH 1 intracellular cytoplasmic domain (NICD)/glioma?associated oncogene 1 (Gli1) pathway, which triggered TWIST1/Slug?hENT1/RRM1 signaling and resensitized GR?HPCCs to gemcitabine. Finally, sclareolide resensitized GR?HPCCs to gemcitabine through inducing apoptosis; in vivo, the co?administraion of sclareolide and gemcitabine effectively suppressed tumor growth. Sclareolide may be a novel agent in combination with gemcitabine for the treatment of gemcitabine?resistant pancreatic cancer, which resensitizes GR?HPCCs to gemcitabine through mediating NICD and Gli1.

Title

Sclareolide enhances gemcitabine?induced cell death through mediating the NICD and Gli1 pathways in gemcitabine?resistant human pancreatic cancer.

Author

Chen S1, Wang Y2, Zhang WL1, Dong MS1, Zhang JH1.

Publish date

2017 Apr

PMID

31738086

Abstract

Filoviruses cause severe hemorrhagic fever in humans. Ebola virus (EBOV) is the most contagious filovirus. Although compassionate treatments have been used during the latest Ebola outbreak, novel anti-EBOV agents are still urgently needed. In this study, sclareol and sclareolide, two natural products in Salvia sclarea, were identified as EBOV entry inhibitors with EC50s of 2.4 μmol/L and 8.0 μmol/L, respectively, through blocking the viral fusion process. Moreover, both compounds exhibited inhibitory effects on all tested filoviruses’ entry, indicating their wide-spectrum activities against filoviruses. This study provides insights into the two natural products and their applications against filovirus infectious diseases.

KEYWORDS

Ebola; Sclareol; entry inhibitor; filovirus; sclareolide

Title

Discovery of sclareol and sclareolide as filovirus entry inhibitors.

Author

Chen Q1, Tang K1, Guo Y1.

Publish date

2020 May

PMID

17202714

Abstract

Fungal catalysis of sclareolide (1) using Mucor plumbeus (ATCC 4740), Cunninghamella blakesleeana (ATCC 9245), Cunninghamella echinulata (ATCC 9244), Curvularia lunata (ATCC 12017) and Aspergillus niger (ATCC 1004), was performed. Cunninghamella blakesleeana (ATCC 9245) metabolized compound 1 to afford O(6)-sclareolide (2), 3beta,6alpha-dihydroxysclareolide (3), 9-hydroxysclareolide (4), along with three known metabolites, 1beta,3beta-dihydroxysclareolide (5), 3-oxosclareolide (6) and 3beta-hydroxysclareolide (7). Biotransformation experiments of compound 1 with Cunninghamella echinulata (ATCC 9244) also yielded two new compounds, 5-hydroxysclareolide (8), and 7beta-hydroxysclareolide (9) along with two known compounds 5 and 7. Spectroscopic methods were used to establish the structures of compounds 2-9. Compounds 2-9 exhibited modest acetylcholinesterase inhibitory activity.

Title

Novel microbial transformations of sclareolide.

Author

Ata A1, Conci LJ, Betteridge J, Orhan I, Sener B.

Publish date

2007 Jan


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