6-Hydroxy-5,6-dehydrosugiol | CAS:140923-35-9

6-Hydroxy-5,6-dehydrosugiol

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Description:

6-Hydroxy-5,6-dehydrosugiol is a potent androgen receptor antagonist in prostate cancer cells, it has potential for use in chemoprevention and chemotherapy of prostate cancers.

Targets:

Androgen Receptor | Caspase | p53 | PARP | CDK

In vivo:

Cancer Res. 2008 Aug 15;68(16):6634-42.

A novel diterpene suppresses CWR22Rv1 tumor growth in vivo through antiproliferation and proapoptosis.[Pubmed: 18701487 ]

Androgen receptor (AR) is the main therapeutic target for treatment of metastatic prostate cancers (PCa). As recurrent tumors restore AR activity independent of hormones, new therapies that abolish AR activity have been sought to prevent or delay the emergence of ablation-resistant disease.
METHODS AND RESULTS:
Here, we report that a novel abietane diterpene, 6-Hydroxy-5,6-dehydrosugiol (HDHS), isolated from the stem bark of Cryptomeria japonica, was a potent AR antagonist in PCa cells. HDHS treatment of androgen-dependent LNCaP and androgen-responsive 22Rv1 cells induced apoptosis as shown by nucleosome release, activation of caspase-3 and caspase-7, and cleavage of poly(ADP-ribose) polymerase accompanied with concomitant up-regulation of tumor suppressor p53. HDHS also decreased the protein expression of cyclins (D1 and E), cyclin-dependent kinases (CDK2, CDK4, and CDK6), and retinoblastoma phosphorylation in PCa cells, which suggest cell cycle arrest in the G(1) phase. Oral administration of HDHS at 0.5 and 2.5 mg/kg once daily for 24 days to 22Rv1 PCa xenografted mice suppressed tumor growth by 22% and 39%, respectively, in association with decreased proliferation and increased apoptosis in tumor cells, which further correlated with increased levels of HDHS in plasma and tumors.
CONCLUSIONS:
Overall, our data suggest that HDHS has potential for use in chemoprevention and chemotherapy of PCa.

6-Hydroxy-5,6-dehydrosugiol Description

Source:	The stem barks of Cryptomeria japonica.
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:

Holzforschung, 2002 , 56 (5) :487-492。

Antioxidant Activity of Abietane-Type Diterpenes from Heartwood of Taiwania cryptomerioides Hayata[Reference: WebLink]

Nine abietane-type diterpenes were isolated from the heartwood of Taiwania cryptomerioides and their structures identified by spectral analyses.
METHODS AND RESULTS:
Among these nine compounds, six diterpenes were isolated for the first time from T. cryptomerioides, including 6,7-dehydroferruginol, 6α-hydroxysugiol, 5,6-dehydro-6-hydroxysugiol(6-Hydroxy-5,6-dehydrosugiol), 11-hydroxyferruginol, secoabietane dialdehyde and isohinokiol. We suggest that abietane-type diterpenes are the dominant diterpenes in the heartwood of T. cryptomerioides. A possible biosynthesis pathway is proposed. In addition, a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay was performed to evaluate the antioxidant activity of these diterpenes.
CONCLUSIONS:
This study demonstrates that ferruginol exhibits the strongest antioxidant activity among the diterpenes isolated from T. cryptomerioides heartwood.

Product Name	6-Hydroxy-5,6-dehydrosugiol
Price:
CAS No.:	140923-35-9
Catalog No.:	CFN92149
Molecular Formula:	C₂₀H₂₆O₃
Molecular Weight:	314.4 g/mol
Purity:	>=98%
Type of Compound:	Diterpenoids
Physical Desc.:	Powder
Source:	The stem barks of Cryptomeria japonica.
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	Anti-androgen receptor Compound Library Anti-prostatic disease Compound Library Diterpenoids Compound Library PARP Inhibitor Library p53 Inhibitor Library CDK Inhibitor Library Caspase Inhibitor Library Androgen Receptor Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.1807 mL	15.9033 mL	31.8066 mL	63.6132 mL	79.5165 mL
5 mM	0.6361 mL	3.1807 mL	6.3613 mL	12.7226 mL	15.9033 mL
10 mM	0.3181 mL	1.5903 mL	3.1807 mL	6.3613 mL	7.9517 mL
50 mM	0.0636 mL	0.3181 mL	0.6361 mL	1.2723 mL	1.5903 mL
100 mM	0.0318 mL	0.159 mL	0.3181 mL	0.6361 mL	0.7952 mL

CFN92187	Sugiol	511-05-7	300.4	C₂₀H₂₈O₂
CFN95803	16-Acetoxylsugiol	1413941-65-7	358.5	C₂₂H₃₀O₄
CFN95805	Gerardianin B	2070919-73-0	390.5	C₂₂H₃₀O₆
CFN95831	16-Acetoxy-7alpha-methoxyroyleanone	109974-33-6	404.5	C₂₃H₃₂O₆
CFN92177	6-Hydroxysugiol	55898-07-2	316.4	C₂₀H₂₈O₃
CFN92149	6-Hydroxy-5,6-dehydrosugiol	140923-35-9	314.4	C₂₀H₂₆O₃
CFN95811	6,12,15-Trihydroxy-5,8,11,13-abietetra-7-one	371155-09-8	330.4	C₂₀H₂₆O₄
CFN95800	Graciliflorin F	1413941-67-9	388.5	C₂₂H₂₈O₆
CFN95815	Graciliflorin E	1413941-66-8	344.5	C₂₁H₂₈O₄
CFN95812	15-O-Methylgraciliflorin F	1411994-51-8	402.5	C₂₃H₃₀O₆