Oridonin

SKU: O0131

Category: Phytochemicals

Synonyms: 7α,20-Epoxy-1α,6β,7,14-tetrahydroxy-Kaur-16-en-15-one, NSC 250682; 28957-04-2
CAS-Number: C₂₀H₂₈O₆
Molecular Formula: 364.43
Molecular Weight

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (HPLC)
Identity: 1H-NMR
Appearance: White to off-white powder

Properties

Solvents: DMSO (20 mg/ml), DMF (20 mg/ml), ethanol (20 mg/ml), water (insoluble)

Short Term Storage: RT
Use / Stability: Stable for at least 2 years after receipt when stored at +4°C.
Handling Advice: Protect from light and moisture.
Long Term Storage: +4°C
Shipping: AMBIENT

Transportation: Not dangerous goods

Description: Oridonin is a diterpenoid that has been found in R. rubescens and has anti-inflammatory and anticancer, antimicrobial and neuroprotective properties. The regulatory anticancer mechanisms include induction of apoptosis and autophagy, inhibition of proliferation, inhibition of angiogenesis, cell cycle arrest. It is an inhibitor of the TLR4/p38-MAPK and TLR4/NF-?B signaling pathways and PPARγ,. Oridonin is a high affinity inhibitor of NLRP3 inflammasome assembly and activation (Kd = 52.5 nM). It inhibits inflammation in wild-type, but not Nlrp3-/-, mice in a model of high-fat diet-induced type 2 diabetes. Also inhibits glial activation, decreases inflammatory cytokine release, attenuates synaptic loss and improves behavioural deficits in Aβ1-42 treated mice.
InChi: InChI=1S/C20H28O6/c1-9-10-4-5-11-18-8-26-20(25,19(11,14(9)22)15(10)23)16(24)13(18)17(2,3)7-6-12(18)21/h10-13,15-16,21,23-25H,1,4-8H2,2-3H3/t10-,11-,12-,13+,15+,16-,18+,19-,20+/m0/s1
References: (1) T. Ikezoe, et al., Int. J. Oncol. 23, 1187 (2003) , (2) J.J. Liu, et al., Ann. Hematol. 83, 691 (2004) , (3) T. Ikezoe, et al., Mol. Cancer Ther. 4, 578 (2005) , (4) Q. Cui, et al., J. Pharmacol. Sci. 105, 317 (2007) , (5) H. Wang, et al., Oncol. Rep. 24, 647 (2010) , (6) Z. Liu, et al., Cell Prolif. 45, 499 (2012) (Review) , (7) S. Wang, et al., PLoS One 9, e104745 (2014) , (8) B.A. Owona & H.J. Schluesener, Drugs R.D. 15, 233 (2015) (Review) , (9) S. Wang, et al, PLoS One 11, e0151397 (2016) , (10) L. Tian, et al., BMC Complement. Altern. Med. 17, 192 (2017) , (11) J. Li, et al., Int. Immunopharmacol. 55, 9 (2018) , (12) J. Xu, et al., Molecules 23, E474 (2018) (Review) , (13) H. He, et al., Nat. Commun. 9, 2550 (2018) , (14) T. Jia, et al., Int. Immunopharmacol. 69, 382 (2019)
InChi Key: SDHTXBWLVGWJFT-XKCURVIJSA-N
Smiles: O[C@@H]1[C@]2(CO3)[C@@]([C@H](O)[C@]3(O)[C@@](C4=O)([C@@H]5O)[C@@]2([H])CC[C@H]5C4=C)([H])C(C)(C)CC1

Oridonin is a diterpenoid that has been found in R. rubescens and has anti-inflammatory and anticancer, antimicrobial and neuroprotective properties. The regulatory anticancer mechanisms include induction of apoptosis and autophagy, inhibition of proliferation, inhibition of angiogenesis, cell cycle arrest. It is an inhibitor of the TLR4/p38-MAPK and TLR4/NF-?B signaling pathways and PPARγ,. Oridonin is a high affinity inhibitor of NLRP3 inflammasome assembly and activation (Kd = 52.5 nM). It inhibits inflammation in wild-type, but not Nlrp3-/-, mice in a model of high-fat diet-induced type 2 diabetes. Also inhibits glial activation, decreases inflammatory cytokine release, attenuates synaptic loss and improves behavioural deficits in Aβ1-42 treated mice.

SKU: O0131 Category: Phytochemicals

Additional information

Additional information

Synonyms	7α,20-Epoxy-1α,6β,7,14-tetrahydroxy-Kaur-16-en-15-one, NSC 250682
Purity	≥98% (HPLC)
Appearance	White to off-white powder
CAS-Number	28957-04-2
Molecular Formula	C20H28O6
Molecular Weight	364.43
Identity	1H-NMR
Solvents	DMSO (20 mg/ml), DMF (20 mg/ml), ethanol (20 mg/ml), water (insoluble)
Smiles	O[C@@H]1[C@]2(CO3)[C@@]([C@H](O)[C@]3(O)[C@@](C4=O)([C@@H]5O)[C@@]2([H])CC[C@H]5C4=C)([H])C(C)(C)CC1
InChi Key	SDHTXBWLVGWJFT-XKCURVIJSA-N
Shipping	AMBIENT
Short Term Storage	RT
Long Term Storage	+4°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Transportation	Not dangerous goods
References	(1) T. Ikezoe, et al., Int. J. Oncol. 23, 1187 (2003), (2) J.J. Liu, et al., Ann. Hematol. 83, 691 (2004), (3) T. Ikezoe, et al., Mol. Cancer Ther. 4, 578 (2005), (4) Q. Cui, et al., J. Pharmacol. Sci. 105, 317 (2007), (5) H. Wang, et al., Oncol. Rep. 24, 647 (2010), (6) Z. Liu, et al., Cell Prolif. 45, 499 (2012) (Review), (7) S. Wang, et al., PLoS One 9, e104745 (2014), (8) B.A. Owona & H.J. Schluesener, Drugs R.D. 15, 233 (2015) (Review), (9) S. Wang, et al, PLoS One 11, e0151397 (2016), (10) L. Tian, et al., BMC Complement. Altern. Med. 17, 192 (2017), (11) J. Li, et al., Int. Immunopharmacol. 55, 9 (2018), (12) J. Xu, et al., Molecules 23, E474 (2018) (Review), (13) H. He, et al., Nat. Commun. 9, 2550 (2018), (14) T. Jia, et al., Int. Immunopharmacol. 69, 382 (2019)
InChi	InChI=1S/C20H28O6/c1-9-10-4-5-11-18-8-26-20(25,19(11,14(9)22)15(10)23)16(24)13(18)17(2,3)7-6-12(18)21/h10-13,15-16,21,23-25H,1,4-8H2,2-3H3/t10-,11-,12-,13+,15+,16-,18+,19-,20+/m0/s1
Quantity	5 mg, 25 mg, Bulk