Imbricatolic acid | CAS:6832-60-6 | Manufacturer ChemFaces

Imbricatolic acid

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Description:

Imbricatolic acid can prevent cell cycle progression in p53-null CaLu-6 cells.

Targets:

p53

In vitro:

Planta Med. 2011 Nov;77(16):1822-8.

Imbricatolic acid from Juniperus communis L. prevents cell cycle progression in CaLu-6 cells.[Pubmed: 21567359]

METHODS AND RESULTS:
Imbricatolic acid was isolated from the methanolic extract of the fresh ripe berries of Juniperus communis (Cupressaceae) together with sixteen known compounds and a new dihydrobenzofuran lignan glycoside named juniperoside A. Their structures were determined by spectroscopic methods and by comparison with the spectral data reported in literature. Imbricatolic acid was evaluated for its ability to prevent cell cycle progression in p53-null CaLu-6 cells. This compound induces the upregulation of cyclin-dependent kinase inhibitors and their accumulation in the G1 phase of the cell cycle, as well as the degradation of cyclins A, D1, and E1. Furthermore, no significant Imbricatolic acid-induced apoptosis was observed.
CONCLUSIONS:
Therefore, this plant-derived compound may play a role in the control of cell cycle.

Molecules. 2007 May 21;12(5):1092-100.

Biotransformations of imbricatolic acid by Aspergillus niger and Rhizopus nigricans cultures.[Pubmed: 17873843]

METHODS AND RESULTS:
Microbial transformation of Imbricatolic acid (1) by Aspergillus niger afforded 1alpha-hydroxyImbricatolic acid (2), while transformation with Rhizopus nigricans yielded 15-hydroxy-8,17-epoxylabdan-19-oic acid (3). When the diterpene 1 was added to a Cunninghamella echinulata culture, the main products were the microbial metabolites mycophenolic acid (4) and its 3-hydroxy derivative 5. All the structures were elucidated by spectroscopic methods. The cytotoxicity of these compounds towards human lung fibroblasts and AGS cells was assessed.
CONCLUSIONS:
While 4 and 5 showed low cytotoxicity, with IC50 values > 1000 microM against AGS cells and fibroblasts, 1alpha-hydroxyImbricatolic acid (2) presented moderate toxicity towards these targets, with IC50 values of 307 and 631 microM, respectively. The structure of 2 is presented for the first time.

Imbricatolic acid Description

Source:	The barks of Pinus massoniana Lamb.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

Bioorg Med Chem Lett. 2012 Jul 15;22(14):4636-9.

Synthesis of novel imbricatolic acid analogues via insertion of N-substituted piperazine at C-15/C-19 positions, displaying glucose uptake stimulation in L6 skeletal muscle cells.[Pubmed: 22726926 ]

METHODS AND RESULTS:
A new class of N-substituted piperazine analogues of Imbricatolic acid have been designed and synthesized by using the appropriate synthetic routes in excellent yield. All synthesised compounds were screened for their in vitro glucose uptake stimulatory activity. Among them compounds 4b, 4e, 8b, and 8e triggered L6 skeletal muscle cells for glucose uptake at 54.73%, 40.79%, 40.90%, and 39.55% stimulation, respectively. Compound 4b has emerged as important lead compound showing potential antidiabetic activity.
CONCLUSIONS:
Illustration about their synthesis and in vitro glucose uptake activity is described.

Product Name	Imbricatolic acid
Price:
CAS No.:	6832-60-6
Catalog No.:	CFN97164
Molecular Formula:	C₂₀H₃₄O₃
Molecular Weight:	322.5 g/mol
Purity:	>=98%
Type of Compound:	Diterpenoids
Physical Desc.:	Powder
Source:	The barks of Pinus massoniana Lamb.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Inhibitors Compound Library Diterpenoids Compound Library p53 Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.1008 mL	15.5039 mL	31.0078 mL	62.0155 mL	77.5194 mL
5 mM	0.6202 mL	3.1008 mL	6.2016 mL	12.4031 mL	15.5039 mL
10 mM	0.3101 mL	1.5504 mL	3.1008 mL	6.2016 mL	7.7519 mL
50 mM	0.062 mL	0.3101 mL	0.6202 mL	1.2403 mL	1.5504 mL
100 mM	0.031 mL	0.155 mL	0.3101 mL	0.6202 mL	0.7752 mL

CFN97164	Imbricatolic acid	6832-60-6	322.5	C₂₀H₃₄O₃
CFN99882	Isocupressic acid	1909-91-7	320.5	C₂₀H₃₂O₃
CFN98880	Acetylisocupressic acid	52992-82-2	362.5	C₂₂H₃₄O₄
CFN99397	Scoparinol	130838-00-5	426.6	C₂₇H₃₈O₄
CFN98250	Agathadiol diacetate	24022-13-7	390.6	C₂₄H₃₈O₄
CFN89384	ent-Labda-8(17),13E-diene-3beta,15,18-triol	90851-50-6	322.48	C₂₀H₃₄O₃
CFN96078	ent-Labda-8(17),13Z-diene-15,16,19-triol 19-O-glucoside	1245636-01-4	484.6	C₂₆H₄₄O₈
CFN89220	Goshonoside F1	90851-24-4	484.63	C₂₆H₄₄O₈
CFN89238	Goshonoside F5	90851-28-8	646.77	C₃₂H₅₄O₁₃
CFN98497	Agatholal	3650-31-5	304.5	C₂₀H₃₂O₂