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Isorosmanol Sale

(Synonyms: 异迷迭香酚) 目录号 : GC36340

Isorosmanol 是从鼠尾草叶中分离出的一种松香烷型二萜,具有抗氧化、神经保护和神经营养作用。Isorosmanol 能抑制 AChE 活性和黑色素的合成。

Isorosmanol Chemical Structure

Cas No.:93780-80-4

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产品描述

Isorosmanol is an abietane-type diterpene isolated from the leaves of sage, with antioxidant, neuroprotective and neurotrophic effects. Isorosmanol inhibits AChE activity and melanin synthesis[1][2][3].

[1]. Miura K, et al. Antioxidant activity of chemical components from sage (Salvia officinalis L.) and thyme (Thymus vulgaris L.) measured by the oil stability index method. J Agric Food Chem. 2002 Mar 27;50(7):1845-51. [2]. Park SY, et al. Neuroprotective and neurotrophic effects of isorosmanol. Z Naturforsch C. 2009 May-Jun;64(5-6):395-8. [3]. Sallam A, et al. Acetylcholine esterase inhibitors and melanin synthesis inhibitors from Salvia officinalis. Phytomedicine. 2016 Sep 15;23(10):1005-11.

Chemical Properties

Cas No. 93780-80-4 SDF
别名 异迷迭香酚
Canonical SMILES O=C1O[C@]2([H])C3=C(C(O)=C(O)C(C(C)C)=C3)[C@@]41CCCC(C)(C)[C@]4([H])[C@H]2O
分子式 C20H26O5 分子量 346.42
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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1 mM 2.8867 mL 14.4333 mL 28.8667 mL
5 mM 0.5773 mL 2.8867 mL 5.7733 mL
10 mM 0.2887 mL 1.4433 mL 2.8867 mL
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Research Update

Biomimetic Synthesis of Isorosmanol and Przewalskin A

J Org Chem 2018 Jan 5;83(1):437-442.PMID:29191008DOI:10.1021/acs.joc.7b02369.

Przewalskin A, a novel C23 terpenoid with anti-HIV-1 activity from Salvia przewalskii Maxim, was formed in 10 steps via Isorosmanol from (+)-carnosic acid. The synthetic strategy was inspired primarily by the biogenetic hypothesis and was enabled by epoxidation, epoxide ring opening, and lactonization in one pot to prepare the 11,12-dimethoxy Isorosmanol, and bismuthonium ylide-induced ring expansion of o-quinone to construct the 2-acyl-3-hydroxytropone.

Neuroprotective and neurotrophic effects of Isorosmanol

Z Naturforsch C J Biosci 2009 May-Jun;64(5-6):395-8.PMID:19678545DOI:10.1515/znc-2009-5-616.

The neurotoxicity induced by beta-amyloid (Abeta), which is one of the major causes of Alzheimer's disease (AD), leads to synaptic loss and subsequent neuronal death. Therefore, modulation of Abeta-induced neurotoxicity, as well as regeneration of damaged synapses could be important therapeutic approaches to control AD. In this study, we found that Isorosmanol, an abietane-type diterpene, protected PC12 cells against Abeta-induced toxicity. Furthermore, Isorosmanol promoted the generation of neurites. The neurotrophic effect of Isorosmanol was enhanced by co-treatment with nerve growth factor (NGF). In addition, the neurite outgrowth induced by Isorosmanol was accompanied by F-actin redistribution and increased expression of neurofilaments. Taken together, these results suggest that Isorosmanol possesses both neuroprotective and neurotrophic effects, that might be beneficial for controlling AD.

Acetylcholine esterase inhibitors and melanin synthesis inhibitors from Salvia officinalis

Phytomedicine 2016 Sep 15;23(10):1005-11.PMID:27444345DOI:10.1016/j.phymed.2016.06.014.

Background: Salvia officinalis is a traditionally used herb with a wide range of medicinal applications. Many phytoconstituents have been isolated from S. officinalis, mainly phenolic diterpenes, which possess many biological activities. Purpose: This study aimed to evaluate the ability of the phenolic diterpenes of S. officinalis to inhibit acetylcholine esterase (AChE) as well as their ability to inhibit melanin biosynthesis in B16 melanoma cells. Methods: The phenolic diterpenes isolated from the aerial parts of S. officinalis were tested for their effect on melanin biosynthesis in B16 melanoma cell lines. They were also tested for their ability to inhibit AChE using Ellman's method. Moreover, a molecular docking experiment was used to investigate the binding affinity of the isolated phenolic diterpenes to the amino acid residues at the active sites of AChE. Results: Seven phenolic diterpenes-sageone, 12-methylcarnosol, carnosol, 7b-methoxyrosmanol, 7a-methoxyrosmanol, Isorosmanol and epirosmanol-were isolated from the methanolic extract of the aerial parts of S. officinalis. Isorosmanol showed a melanin-inhibiting activity as potent as that of arbutin. Compounds 7a-methoxyrosmanol and Isorosmanol inhibited AChE activity by 50% and 65%, respectively, at a concentration of 500 µM. Conclusions: The results suggest that Isorosmanol is a promising natural compound for further studies on development of new medications which might be useful in ageing disorders such as the declining of cognitive functions and hyperpigmentation.

New terpenoid glycosides obtained from Rosmarinus officinalis L. aerial parts

Fitoterapia 2014 Dec;99:78-85.PMID:25200369DOI:10.1016/j.fitote.2014.09.004.

Five new terpenoid glycosides, named as officinoterpenosides A₁ (1), A₂ (2), B (3), C (4), and D (5), together with 11 known ones, (1S,4S,5S)-5-exo-hydrocamphor 5-O-β-D-glucopyranoside (6), Isorosmanol (7), rosmanol (8), 7-methoxyrosmanol (9), epirosmanol (10), ursolic acid (11), micromeric acid (12), oleanolic acid (13), niga-ichigoside F₁ (14), glucosyl tormentate (15), and asteryunnanoside B (16), were obtained from the aerial parts of Rosmarinus officinalis L. Their structures were elucidated by chemical and spectroscopic methods (UV, IR, HRESI-TOF-MS, 1D and 2D NMR). Among the new ones, 1 and 2, 3 and 4 are diterpenoid and triterpenoid glycosides, respectively; and 5 is a normonoterpenoid. For the known ones, 6 was isolated from the Rosmarinus genus first, and 15, 16 were obtained from this species for the first time.

Apianane terpenoids from Salvia officinalis

Phytochemistry 2001 Dec;58(8):1171-5.PMID:11738402DOI:10.1016/s0031-9422(01)00341-7.

Three apianane terpenoids, rel-(5S, 6S, 7S, 10R, 12S, 13R)-7-hydroxyapiana-8,14-diene-11,16-dion-(22,6)-olide, rel-(5S, 6S, 7R, 10R, 12S, 13R)-7-hydroxyapiana-8,14-diene-11,16-dion-(22,6)-olide and rel-(5S, 6S, 7S, 10R, 12R, 13S)-7-hydroxyapiana-8,14-diene-11,16-dion-(22,6)-olide were isolated from the leaves of Salvia officinalis, together with 15 known compounds, salvigenin, lupeol, beta-sitosterol, stigmasterol, physcion, carnosol, rosmadial, rosmanol, epirosmanol, Isorosmanol, columbaridione, atuntzensin A, miltirone, carnosic acid and 12-O-methyl carnosic acid. Their structures were established on the basis of spectral evidence.