Structural characterization of minor optically pure and impure meroterpenoid-type compounds in Ganoderma lucidum and structure revision of spirolingzhine D

Zhang, Jiaojiao; Wang, Da‐Wei; Peng, Yun-Li; Katta, Murali Krishna; Dong, Hezhong; Cheng, Yong‐Xian

doi:10.1016/j.tet.2022.133039

Cited by 3 publications

(20 citation statements)

References 23 publications

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“…Optical rotation data were determined by using an Anton Paar MCP‐100 digital polarimeter or a Anton Paar ADP 440 digital polarimeter. UV spectra, CD spectra, NMR spectra and HR‐ESI‐MS were recorded by using the same equipments as we previously reported [12] . Column chromatography was performed on silica gel, MCI gel CHP 20P, YMC‐GEL ODS A‐HG and Sephadex LH‐20 as we previously described, [12] and RP‐18 (40–60 μm, Daiso Co., Tokyo, Japan).…”

Section: Methodsmentioning

confidence: 99%

“…UV spectra, CD spectra, NMR spectra and HR‐ESI‐MS were recorded by using the same equipments as we previously reported [12] . Column chromatography was performed on silica gel, MCI gel CHP 20P, YMC‐GEL ODS A‐HG and Sephadex LH‐20 as we previously described, [12] and RP‐18 (40–60 μm, Daiso Co., Tokyo, Japan). Semi‐preparative HPLC was carried out through a Saipuruisi chromatograph with a YMC‐Pack ODS−A column (250 mm ×10 mm, i.d., 5 μm).…”

Section: Methodsmentioning

confidence: 99%

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Isolation and Characterization of trans‐p‐Hydroxycinnamoyl Meroterpenoids from Ganoderma sinensis

Yin

Zhao

Zhang

et al. 2023

Chemistry & Biodiversity

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Zizhines V, W, Y, Z, (�)-zizhines X, and Z1À Z3, and (�)-ganosinensol L, thirteen new compounds including four pairs of enantiomers and a known compound (À )-ganosinensol L, were isolated from the fruiting bodies of Ganoderma sinensis. Their structures were identified by spectroscopic, computational methods, and CD (circular dichroism spectroscopy) comparisons. Zizhines VÀ Z and Z1À Z3 are meroterpenoids consisting of the phenolic and the terpenoidal parts. All the compounds except zizhine Z3 bear a common trans-p-hydroxycinnamoyl group. Biological evaluation shows that (À )-zizhine Z1 inhibits cell migration in the MDA-MB-231 cell lines. The present study discloses the chemical profiling of G. sinensis and paves the way for its development as functional products to benefit chronic disorders.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Isolation and Characterization of trans‐p‐Hydroxycinnamoyl Meroterpenoids from Ganoderma sinensis

Yin

Zhao

Zhang

et al. 2023

Chemistry & Biodiversity

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“…34,35 Other analogs named (±)-lucidumone J (7 and 8) and lucidumin A (9) were found generated from G. lucidum. 13,36 Of which, (+)-lucidumone J (7) possessed a reported activation of glucose uptake and p-AKT and p-IRS1 expression, and lucidumin A (9) demonstrated significant activity against inflammation. 13,36 Structurally similar meroterpenoids with a reduced double bond attached by the carboxyl group were widely identified from Ganoderma species.…”

Section: Meroterpenoids With Two Isoprene Units As Side Chainsmentioning

confidence: 99%

“…13,36 Of which, (+)-lucidumone J (7) possessed a reported activation of glucose uptake and p-AKT and p-IRS1 expression, and lucidumin A (9) demonstrated significant activity against inflammation. 13,36 Structurally similar meroterpenoids with a reduced double bond attached by the carboxyl group were widely identified from Ganoderma species. (±)-Chizhine D (10 and 11) were first described in the investigation of G. lucidum in 2014 and revised the absolute configuration of the two enantiomers in 2016.…”

Section: Meroterpenoids With Two Isoprene Units As Side Chainsmentioning

confidence: 99%

“…Fifty-six out of 104 articles around the world on GM isolation were contributed by our group, involving many complex novel skeletons (lingzhiols, lucidumone, cochlearols A and B, ganodermaones A and B, dispirocochlearoids, sinensilactam A, applanatumin A, cochlearoids, and cochlearines) that were published in Organic Letters and natural product related journals, and several patterns for the determination of configurations. 3,[5][6][7][8][9][10][11][12][13] In the present stage of research on GMs, it is necessary to analyze and summarize their structure characterizations for revealing scientific patterns and indicating the directions of further research on GMs. Several reviews on GMs have summarized structure, biological activity, biosynthetic pathways, and total synthesis, and have presented this information from different viewpoints.…”

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confidence: 99%

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Insights into Ganoderma fungi meroterpenoids opening a new era of racemic natural products in mushrooms

Zhang,

Qin,

Cheng

2024

Medicinal Research Reviews

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Ganoderma meroterpenoids (GMs) containing 688 structures to date were discovered to have multiple remarkable biological activities. 65.6% of meroterpenoids featuring stereogenic centers from Ganoderma species are racemates. Further, GMs from different Ganoderma species seem to have their own characteristics. In this review, a comprehensive summarization of GMs since 2000 is presented, including GM structures, structure corrections, biological activities, physicochemical properties, total synthesis, and proposed biosynthetic pathways. Additionally, we especially discuss the racemic nature, species‐related structural distribution, and structure–activity relationship of GMs, which will provide a likely in‐house database and shed light on future studies on GMs.

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Anti-tumor and anti-oxidant effects of Ganoderma lucidum extracts on oral squamous cell carcinoma and skin squamous cell carcinoma in vitro

Haleem,

Taha,

Ayoub

2024

Current Issues in Pharmacy and Medical Sciences

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Ganoderma lucidum has had great importance in healthcare in the Chinese for many decades. Polysaccharides and triterpenoids are one of the most important components of G. lucidum. Biological evidence indicates that this mushroom can be a promising treatment in many cancer cases and reduce the toxic effect of chemotherapy and radiotherapy if taken synchronously. This study highlights preparing an extract with therapeutic effects capable of removing free radicals and protecting cell membranes from hyperoxidation effects. The antitumor effect was evaluated on two types of cancer cell lines in vitro, Human Oral Squamous Cell Carcinoma (HOSCC) and Human Skin Squamous Cell Carcinoma (HSSCC), at different concentrations 0.0-1600 µg/mL. Antioxidant by DPPH assay was assessed at concentrations from 0.0-500 µg/mL, in addition to their effects on cytogenetic indicators such as mitotic index (MI), blastogenic index (BI) and total chromosomal aberration (TCAs) for three types of extracts (ethanol extract, water extract and acidified water extract). The results recorded an increase in the antioxidant activity of the three extracts, and that the acidified water extract had the highest effect, reaching a killing rate of 78.53% for the acidified water extract on the HOSCC cell line. Chromosomal stability indicates that the three extracts enhanced the cytogenetics parameters and supported chromosomal stability by increasing both mitotic index (MI) and blastogenic index (BI), while reducing chromosomal aberrations.

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Structural characterization of minor optically pure and impure meroterpenoid-type compounds in Ganoderma lucidum and structure revision of spirolingzhine D

Cited by 3 publications

References 23 publications

Isolation and Characterization of trans‐p‐Hydroxycinnamoyl Meroterpenoids from Ganoderma sinensis

Isolation and Characterization of trans‐p‐Hydroxycinnamoyl Meroterpenoids from Ganoderma sinensis

Insights into Ganoderma fungi meroterpenoids opening a new era of racemic natural products in mushrooms

Anti-tumor and anti-oxidant effects of Ganoderma lucidum extracts on oral squamous cell carcinoma and skin squamous cell carcinoma in vitro

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