Neuronal growth promoting sesquiterpene–neolignans; syntheses and biological studies

Cheng, Xu; Harzdorf, Nicole L.; Khaing, Zin Z.; Kang, Danby; Camelio, Andrew M.; Shaw, Travis W.; Schmidt, Christine E.; Siegel, Dionicio

doi:10.1039/c1ob06363d

Cited by 40 publications

(21 citation statements)

References 28 publications

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“…Chemical constituents from Hericium erinaceus promote neuronal survival and potentiate neurite outgrowth via the TrkA/Erk1/2 pathway. Since neurotrophins are not able to pass the blood brain barrier (BBB) due to their high molecular weights, NGF -inducing small molecules and NGF mimics became the focus of research activities [ 2 , 3 ]. In the domain of natural product research, several NGF -inducing constituents that are derived from different sources have been reported [ 4 , 5 ], and among the first were secondary metabolites of H. erinaceus .…”

Section: Introductionmentioning

confidence: 99%

Two New Cyathane Diterpenoids from Mycelial Cultures of the Medicinal Mushroom Hericium erinaceus and the Rare Species, Hericium flagellum

Rupcic

Rascher

Kanaki

et al. 2018

IJMS

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Basidiomycetes of the genus Hericium are among the most praised medicinal and edible mushrooms, which are known to produce secondary metabolites with the potential to treat neurodegenerative diseases. This activity has been attributed to the discovery of various terpenoids that can stimulate the production of nerve growth factor (NGF) or (as established more recently) brain-derived neurotrophic factor (BDNF) in cell-based bioassays. The present study reports on the metabolite profiles of a Lion’s Mane mushroom (Hericium erinaceus) strain and a strain of the rare species, Hericium flagellum (synonym H. alpestre). While we observed highly similar metabolite profiles between the two strains that were examined, we isolated two previously undescribed metabolites, given the trivial names erinacines Z1 and Z2. Their chemical structures were elucidated by means of nuclear magnetic resonance (NMR) spectroscopy and high resolution mass spectrometry. Along with six further, previously identified cyathane diterpenes, the novel erinacines were tested for neurotrophin inducing effects. We found that erinacines act on BDNF, which is a neurotrophic factor that has been reported recently by us to be induced by the corallocins, but as well on NGF expression, which is consistent with the literature.

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Section: Introductionmentioning

confidence: 99%

Two New Cyathane Diterpenoids from Mycelial Cultures of the Medicinal Mushroom Hericium erinaceus and the Rare Species, Hericium flagellum

Rupcic

Rascher

Kanaki

et al. 2018

IJMS

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“…However, NGF’s high molecular weight restricts its delivery across the blood-brain barrier (BBB). Hence, NGF-mimic or NGF-potentiated small molecules show significant therapeutic potential for their pharmacological advantages [ 6 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

Chemical Constituents from Hericium erinaceus Promote Neuronal Survival and Potentiate Neurite Outgrowth via the TrkA/Erk1/2 Pathway

Zhang

Cao

Kubo

et al. 2017

IJMS

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Hericium erinaceus is a culinary-medicinal mushroom used traditionally in Eastern Asia to improve memory. In this work, we investigated the neuroprotective and neuritogenic effects of the secondary metabolites isolated from the MeOH extract of cultured mycelium of H. erinaceus and the primary mechanisms involved. One new dihydropyridine compound (6) and one new natural product (2) together with five known compounds (1,3–5,7) were obtained and their structures were elucidated by spectroscopic analysis, including 2D NMR and HRMS. The cell-based screening for bioactivity showed that 4-chloro-3,5-dimethoxybenzoic methyl ester (1) and a cyathane diterpenoid, erincine A (3), not only potentiated NGF-induced neurite outgrowth but also protected neuronally-differentiated cells against deprivation of NGF in PC12 pheochromocytoma cells. Additionally, compound 3 induced neuritogenesis in primary rat cortex neurons. Furthermore, our results revealed that TrkA-mediated and Erk1/2-dependant pathways could be involved in 1 and 3-promoted NGF-induced neurite outgrowth in PC12 cells.

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“…4 Aluminum phenoxide was synthesized and used differently in several chemical processes. It has been utilized in an isolated or in situ generated forms [27,[29][30][31]. In fact, the synthesis of aluminum phenoxide was first reported over 130 years ago [32].…”

Section: Introductionmentioning

confidence: 99%

Structural and spectroscopic characterizations of aluminum phenoxide

Mohammadnezhad

Amini

Khavasi

et al. 2016

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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A synthetic route to obtain crystalline aluminum phenoxide was established. Its molecular structure in solid-state and solution is unambiguously determined by single-crystal X-ray diffraction and (1)H, (13)C and (27)Al NMR spectroscopy. The single-crystal X-ray analysis revealed the presence of the dimeric THF adduct [Al(OPh)3·THF]2 with a disordered trigonal bipyramidal geometry at the aluminum atom which is bonded to a THF ligand, two terminal and two bridging phenoxy groups (OPh). The solution behavior of the title compound was investigated by (27)Al NMR in non-coordinating (CDCl3) as well as coordinating (THF) solvents at different temperatures. The obtained results indicate the presence of four- and five-coordinate species in solution.

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Neuronal growth promoting sesquiterpene–neolignans; syntheses and biological studies

Cited by 40 publications

References 28 publications

Two New Cyathane Diterpenoids from Mycelial Cultures of the Medicinal Mushroom Hericium erinaceus and the Rare Species, Hericium flagellum

Two New Cyathane Diterpenoids from Mycelial Cultures of the Medicinal Mushroom Hericium erinaceus and the Rare Species, Hericium flagellum

Chemical Constituents from Hericium erinaceus Promote Neuronal Survival and Potentiate Neurite Outgrowth via the TrkA/Erk1/2 Pathway

Structural and spectroscopic characterizations of aluminum phenoxide

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