| Identification | Back Directory | [Name]
KIRENOL | [CAS]
52659-56-0 | [Synonyms]
Kirel
Kirenol
KIRENOL(P)
(1R)-1-[(2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]ethane-1,2-diol
(1R,3S,4aS,4bS,7S,10aS)-1,2,3,4,4a,4b,5,6,7,9,10,10a-Dodecahydro-3-hydroxy-7-[(R)-1,2-dihydroxyethyl]-1,4a,7-trimethylphenanthrene-1-methanol
1,7-Phenanthrenedimethanol, 1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-3-hydroxy-α7-(hydroxymethyl)-1,4a,7-trimethyl-, (α7R,1R,3S,4aS,4bR,7S,10aS)-
1,7-PhenanthrenediMethanol,1,2,3,4,4a,4b,5,6,7,- 9,10,10a-dodecahydro-3-hydroxy-R7- (hydroxyMethyl)-1,4a,7-triMethyl-,(R7R,1R,- 3S,4aS,4bR,7S,10aS)- | [Molecular Formula]
C20H34O4 | [MDL Number]
MFCD00210519 | [MOL File]
52659-56-0.mol | [Molecular Weight]
338.48 |
| Chemical Properties | Back Directory | [Melting point ]
197.0 to 201.0 °C | [Boiling point ]
516.9±35.0 °C(Predicted) | [density ]
1.17±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
Ethanol (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
14.06±0.20(Predicted) | [color ]
White to Light Yellow | [Cosmetics Ingredients Functions]
ANTIMICROBIAL
HAIR CONDITIONING
SKIN CONDITIONING - EMOLLIENT
ANTIOXIDANT | [InChI]
InChI=1/C20H34O4/c1-18(17(24)11-21)7-6-15-13(8-18)4-5-16-19(2,12-22)9-14(23)10-20(15,16)3/h8,14-17,21-24H,4-7,9-12H2,1-3H3/t14-,15-,16-,17+,18+,19+,20+/s3 | [InChIKey]
NRYNTARIOIRWAB-QNOIMPALNA-N | [SMILES]
C[C@@]12C[C@H](O)C[C@@](C)(CO)[C@@]1([H])CCC1=C[C@@](C)([C@@H](O)CO)CC[C@@]21[H] |&1:1,3,6,10,16,18,24,r| | [CAS DataBase Reference]
52659-56-0 |
| Hazard Information | Back Directory | [Description]
Kirenol is a diterpenoid that has been found in S. orientalis and has diverse biological activities, including anti-arthritic and anti-inflammatory properties.1,2 It inhibits Gram-positive and Gram-negative bacterial growth in disc diffusion assays with MICs ranging from 39 to 156 and 312.5 to 625 μg/ml, respectively.3 Kirenol also reduces K652 chronic myeloid leukemia cell viability with a 48 hour IC50 value of 18.19 μg/ml and induces apoptosis.4 In vivo, kirenol (2 mg/kg, p.o.) reduces motor deficit, delays disease onset by approximately five days, and downregulates inflammatory CD4+IFN-γ+ Th1 cells and CD4+IL-17A+ Th17 cells in a mouse model of experimental autoimmune encephalomyelitis (EAE).5 Intragastric administration of kirenol (1-4 mg/kg) reduces the arthritis index, NF-kB activity, and paw swelling and increases annexin-1 expression without affecting glucocorticoid receptor α (GRα) expression in the synovium in a rat model of collagen-induced arthritis.1 Topical administration of kirenol (0.3-0.5% w/w) reduces edema induced by carrageenan, complete Freund''s adjuvant (CFA), and formalin in rats up to 44, 67, and 65%, respectively.2 | [Chemical Properties]
Yellow crystalline powder, easily soluble in methanol, poorly soluble in water, derived from Siegesbeckia serrata. | [Uses]
Kirenol is a pharmaceutical agent that induces apoptosis in human chronic myeloid leukemia cells. | [Definition]
ChEBI: Kirenol is a diterpenoid. | [References]
[1] ZHE-MING WANG . Kirenol upregulates nuclear Annexin-1 which interacts with NF-κB to attenuate synovial inflammation of collagen-induced arthritis in rats[J]. Journal of ethnopharmacology, 2011, 137 1: Pages 774-782. DOI: 10.1016/j.jep.2011.06.037
[2] JIAN-PING WANG . Topical anti-inflammatory and analgesic activity of kirenol isolated from Siegesbeckia orientalis[J]. Journal of ethnopharmacology, 2011, 137 3: Pages 1089-1094. DOI: 10.1016/j.jep.2011.07.016
[3] JIAN-PING WANG Yong H Z Ya Ming Zhou. Kirenol production in hairy root culture of Siegesbeckea orientalis and its antimicrobial activity.[J]. Pharmacognosy Magazine, 2012, 8 30: 149-155. DOI: 10.4103/0973-1296.96569
[4] YUE LU. Kirenol, a compound from Herba Siegesbeckiae, induces apoptosis in human chronic myeloid leukemia K562 cells.[J]. Pharmazie, 2014, 69 2: 148-153.
[5] JUAN XIAO. Kirenol attenuates experimental autoimmune encephalomyelitis by inhibiting differentiation of Th1 and th17 cells and inducing apoptosis of effector T cells.[J]. Scientific Reports, 2015: 9022. DOI: 10.1038/srep09022 |
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