1-Hydroxybisabola-2,10-dien-4-one

1-Hydroxybisabola-2,10-dien-4-one

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1-Hydroxybisabola-2,10-dien-4-one
Category Others
Catalog number BBF-04397
CAS 1213251-45-6
Molecular Weight 236.35
Molecular Formula C15H24O2
Purity 96.5%

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Description

1-Hydroxybisabola-2,10-dien-4-one is produced in the cultures of Fungus Psathyrella candolleana.

Specification

Synonyms 2-Cyclohexen-1-one, 5-[(1S)-1,5-dimethyl-4-hexen-1-yl]-4-hydroxy-2-methyl-, (4R,5R)-
Storage Store at -20°C
IUPAC Name (4R,5R)-4-hydroxy-2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]cyclohex-2-en-1-one
Canonical SMILES CC1=CC(C(CC1=O)C(C)CCC=C(C)C)O
InChI InChI=1S/C15H24O2/c1-10(2)6-5-7-11(3)13-9-14(16)12(4)8-15(13)17/h6,8,11,13,15,17H,5,7,9H2,1-4H3/t11-,13+,15-/m0/s1
InChI Key YDCNFZXDPQSPKG-LNSITVRQSA-N

Properties

Appearance Oily Matter
Boiling Point 359.2±41.0°C (Predicted)
Density 0.987±0.06 g/cm3 (Predicted)
Solubility Soluble in Chloroform, Ethyl Acetate, DMSO, Acetone

Reference Reading

1. A novel antihypertension agent, sargachromenol D from marine brown algae, Sargassum siliquastrum, exerts dual action as an L-type Ca2+ channel blocker and endothelin A/B2 receptor antagonist
Gab-Man Park, Woon-Seob Shin, Byong-Gon Park, Sangtae Oh, Nam Ik Kim, Seokjoon Lee Bioorg Med Chem . 2017 Sep 1;25(17):4649-4655. doi: 10.1016/j.bmc.2017.07.002.
We isolated the novel vasoactive marine natural products, (5E,10E)-14-hydroxy-2,6,10-trimethylpentadeca-5,10-dien-4-one (4) and sargachromenol D (5), from Sargassum siliquastrum collected from the coast of the East Sea in South Korea by using activity-guided HPLC purification. The compounds effectively dilated depolarization (50mMK+)-induced basilar artery contraction with EC50values of 3.52±0.42 and 1.62±0.63μM, respectively, but only sargachromenol D (5) showed a vasodilatory effect on endothelin-1 (ET-1)-induced basilar artery contraction (EC50=9.8±0.6μM). These results indicated that sargachromenol D (5) could act as a dual antagonist of l-type Ca2+channel and endothelin A/B2receptors. Moreover, sargachromenol D (5) lowered blood pressure in spontaneous hypertensive rats (SHRs) 2h after oral treatment at a dose of 80mg/kg dose and the effect was maintained for 24h. Based on our ex vivo and in vivo experiments, we propose that sargachromenol D (5) is a strong candidate for the treatment of hypertension that is not controlled by conventional drugs, in particular, severe-, type II diabetes-, salt-sensitive, and metabolic disease-induced hypertension.
2. Isolation, Characterization, and Possible Anti-Alzheimer's Disease Activities of Bisabolane-Type Sesquiterpenoid Derivatives and Phenolics from the Rhizomes of Curcuma longa
Dong-Qing Fei, Yi-Fan Yu, Zong-Ping Zhang, Bing Li, Feng-Ming Qi, Zhan-Xin Zhang, Pei-Qian Wu, De-Juan Zhi, Pan-Jie Su, Xu Liu Chem Biodivers . 2020 May;17(5):e2000067. doi: 10.1002/cbdv.202000067.
One new bisabolane-type sesquiterpenoid, together with four known bisabolane-type sesquiterpenoid derivatives and seven phenolics, was isolated from the rhizomes of Curcuma longa. Their structures were elucidated by extensive spectroscopic (IR, HR-ESI-MS, and NMR) data analysis. The possible anti-Alzheimer's disease (AD) activities of the isolated compounds were also evaluated using Caenorhabditis elegans AD pathological model, and 1β-hydroxybisabola-2,10-dien-4-one had the highest possible anti-AD activity.

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