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Terminal Cyclohexane-Type Meroterpenoids from the Fruiting Bodies of Ganoderma cochlear.

ABSTRACT: Eleven new cyclohexane-type meroterpenoids (1, 3-5, 7, 8, 11-15) and four known similar meroterpenoids (2, 6, 9, and 10) were isolated from Ganoderma cochlear. Their structures and absolute configurations at stereogenic centers were elucidated by using HRESIMS, NMR spectroscopy and computational methods. In addition, the structure of the known meroterpenoid, cochlearol G (2), was revised, and the absolute configurations at the stereogenic centers of known meroterpenoids 9 and 10 were determined. All the isolated meroterpenoids were evaluated for their activities against renal fibrosis and triple negative breast cancer, and their insulin resistance. The results of the renal fibrosis study showed that meroterpenoid 11 inhibits over-expression of fibronectin, collagen I and α-SMA. Results of the wound healing study revealed that 4, 6 and 8 significantly inhibit migration of BT549 cells. Observations made in Western blotting experiments showed that 6 decreases the levels of TWIST1 and ZEB1, and increases the level of E-cadherin. Finally, meroterpenoids 7, 9, 11, and 15 significantly up-regulate p-AMPK protein expression in normal L6 myotubes cells.

SUBMITTER: Qin FY

PROVIDER: S-EPMC8677669 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Terminal Cyclohexane-Type Meroterpenoids from the Fruiting Bodies of Ganoderma cochlear.

Qin Fu-Ying FY Xu Te T Li Yan-Peng YP Zhang Hao-Xing HX Cai Dan D Liu Li-Zhong LZ Cheng Yong-Xian YX

Frontiers in chemistry 20211203

Eleven new cyclohexane-type meroterpenoids (1, 3-5, 7, 8, 11-15) and four known similar meroterpenoids (2, 6, 9, and 10) were isolated from Ganoderma cochlear. Their structures and absolute configurations at stereogenic centers were elucidated by using HRESIMS, NMR spectroscopy and computational methods. In addition, the structure of the known meroterpenoid, cochlearol G (2), was revised, and the absolute ...[more]

PMID: 34926404

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Project description:A water-soluble glycopeptide (PGY), fractionated and purified from the aqueous extract of the fruiting bodies of Ganoderma lucidum via two-step dialysis, anion exchange, and gel permeation chromatography, was constituted of two moieties of carbohydrate and peptide. Carbohydrate characterization with component analysis, methylation analysis, periodate oxidation, Smith degradation, enzymic hydrolysis, and IR and NMR experiments demonstrated that the carbohydrate moiety possessed a backbone of approximately 33 (1-->3)-linked beta-d-glucopyranosyl residues and side chains, at positions 6, of single alpha-l-arabinofuranosyl residues for every three Glcp residues in the main chain. On the basis of the results of amino acid composition and trypsin digestion, the peptide moiety, shown to consist of Arg, Ser, Ala, and Gly in a ratio of 1:1:2:2, exhibited the sequence of Ser-Arg-[(Ala)2(Gly)2] and was O-attached to the carbohydrate moiety via Ser. To contribute toward our understanding of the structure-activity relationship, a series of expected derivatives generated from PGY by trypsin digestion, debranching, and NaIO4 oxidation following reduction experiments, including PTC, DB-PGY, and PPP, were obtained. All of them, as well as PGY and a reference compound (butylated hydroxytoluene, BHT), were evaluated with two conventional antioxidant testing systems of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and superoxide radical scavenging and found to have their respective antioxidant activities in a concentration-dependent manner. Comparable radical-scavenging activities observed between PTC and PGY demonstrated that the removal of Ala and Gly in a peptide moiety did not result in the variation of biological functions of PGY. However, it was very interesting to note that the scavenging activity of PPP was higher for DPPH radicals, with an SC(50) value of 116.4 +/- 5.1 microg/mL, and lower for superoxide radicals, with an SC(50) value of 205.2 +/- 14.4 microg/mL, than that of PGY with corresponding SC(50) values of 133.5 +/- 5.5 and 140.5 +/- 7.7 microg/mL, and, moreover, DB-PGY displayed the weakest scavenging potency in the tested samples, indicating that the carbohydrate moiety, in particular the side chain of nonreducing end units of Araf residues as the functional region, played a vital role in the structure and antioxidant activity. In addition, compared with the SC(50) value of BHT, PGY showed lower DPPH radical-scavenging activity but possessed higher superoxide radical-quenching potency, suggesting that it could be presented as a possible new source of natural antioxidants.

Dataset Information

Terminal Cyclohexane-Type Meroterpenoids from the Fruiting Bodies of Ganoderma cochlear.

Publications

Terminal Cyclohexane-Type Meroterpenoids from the Fruiting Bodies of <i>Ganoderma cochlear</i>.

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