LIPID MAPS

Structure Database (LMSD)

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Common Name

Hericene A

Systematic Name

4-((2E)-3,7-Dimethyl-2,6-octadien-1-yl)-2-formyl-3-hydroxy-5-methoxyphenyl)methyl hexadecanoate

Synonyms

5′-Deoxohericenone C
hexadecanoic acid, [4-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-2 formyl-3-hydroxy-5-methoxyphenyl]methyl ester

LM ID

LMPK15030080

Formula

C₃₅H₅₆O₅

Exact Mass

Calculate m/z

556.412776

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Hericene A is a polyketide synthase-derived geranyl resorcylate that has been found in H. erinaceus and has diverse biological activities.^1,2,3,4,5 It is an inhibitor of α-glucosidase (IC50 = 6.7 µM).³ Hericene A (1-100 µM) decreases LPS-induced TNF-α, IL-6, and nitric oxide (NO) production in RAW 264.7 cells.⁴ It increases the axon length of primary rat hippocampal neurons and improves recognition memory in mice.⁵

This information has been provided by Cayman Chemical

References

1. Chen, J., Zeng, X., Yang, Y.L., et al. Genomic and transcriptomic analyses reveal differential regulation of diverse terpenoid and polyketides secondary metabolites in Hericium erinaceus. Sci. Rep. 7(1), 10151 (2017).

2. Kobayashi, S., Hamada, Y., Yasumoto, T., et al. Total syntheses and endoplasmic reticulum stress suppressive activities of hericenes A−C and their derivatives. Tetrahedron Lett. 59(18), 1733-1736 (2018).

3. Lee, S.K., Ryu, S.H., Turk, A., et al. Characterization of α-glucosidase inhibitory constituents of the fruiting body of lion’s mane mushroom (Hericium erinaceus). J. Ethnaopharmacol. 262, 113197 (2020).

4. Xie, G., Tang, L., Xie, Y., et al. Secondary metabolites from Hericium erinaceus and their anti-inflammatory activities. Molecules 27(7), 2157 (2022).

5. Martínez-Mármol, R., Chai, Y., Conroy, J.N., et al. Hericerin derivatives activates a pan-neurotrophic pathway in central hippocampal neurons converging to ERK1/2 signaling enhancing spatial memory. J. Neurochem. 165(6), 791-808 (2023).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Hericium erinaceus (#91752)

Agaricomycetes (#155619)

Secondary Mold Metabolites: Part 46. Hericenes A-C and Erinapyrone C, New Metabolites Produced by the Fungus Hericium erinaceus,
J Nat Prod, 1994

DOI: 10.1021/np50107a006

String Representations

InChiKey (Click to copy)

PLUINHYLFTYIKB-BYNJWEBRSA-N

InChi (Click to copy)

InChI=1S/C35H56O5/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-22-34(37)40-27-30-25-33(39-5)31(35(38)32(30)26-36)24-23-29(4)21-19-20-28(2)3/h20,23,25-26,38H,6-19,21-22,24,27H2,1-5H3/b29-23+

SMILES (Click to copy)

C1(O)C(C/C=C(\C)/CC/C=C(\C)/C)=C(OC)C=C(COC(=O)CCCCCCCCCCCCCCC)C=1C=O