Skeletal meroterpenoids from Ganoderma petchii mushrooms that potentially stimulate umbilical cord mesenchymal stem cells

Dai, Wenwen; Zhu, Yanxia; Qin, Fu-Ying; Chang, Junlei; Zeng, Yicheng; Wang, Jigang; Zhang, Yuanyuan; Cheng, Yong‐Xian

doi:10.1016/j.bioorg.2020.103675

Cited by 8 publications

(11 citation statements)

References 18 publications

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“…We have focused on the investigation of Ganoderma meroterpenoids since 2009. As a result, many structurally intriguing and biologically important meroterpenoids have been characterized by us ( Yan et al, 2019 ; Dai et al, 2020 ; Qin et al, 2020 ; Zhang et al, 2020 ). Due to considerable economic values, Ganoderma species have been cultivated in several places of our country.…”

Section: Introductionmentioning

confidence: 99%

Meroterpenoids From Ganoderma lucidum Mushrooms and Their Biological Roles in Insulin Resistance and Triple-Negative Breast Cancer

et al. 2021

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Ganoderma fungi as popular raw materials of numerous functional foods have been extensively investigated. In this study, five pairs of meroterpenoid enantiomers beyond well-known triterpenoids and polysaccharides, dayaolingzhiols I−M (1–5), were characterized from Ganoderma lucidum. Their structures were identified using spectroscopic and computational methods. Structurally, compound 1 features a novel dioxabicyclo[2.2.2]octan-3-one motif in the side chain. Ethnoknowledge-derived biological evaluation found that (+)-5 could activate Akt and AMPK phosphorylation in insulin-stimulated C2C12 cells, and (+)-5 could activate glucose uptake dose dependently in C2C12 cells. Furthermore, we found that (+)-1 (+)-4, and (–)-4 could significantly inhibit cell migration of the MDA-MB-231 cell line, of which (+)-4 showed significant inhibitory effects against cell migration of the MDA-MB-231 cell line in a dose-dependent manner. These findings revealed the meroterpenoidal composition of G. lucidum and its roles in the prevention of chronic diseases such as diabetes mellitus and triple-negative breast cancer.

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Section: Introductionmentioning

confidence: 99%

Meroterpenoids From Ganoderma lucidum Mushrooms and Their Biological Roles in Insulin Resistance and Triple-Negative Breast Cancer

et al. 2021

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“…33,34 Similar GMs, (±)-petchilactone C (133 and 134), with a 5/5/5/7/6 ring system were discovered from G. petchii and elucidated stereochemistry by using X-ray analysis and ECD calculations. 64 (−)-Petchilactone C (134) was reported to possess the ability for inducing umbilical cord mesenchymal stem cells into keratinocyte-like cells. 64 Of these analogs, lingzhilactone D (111 and 112) and applanatumol D (113 and 114) share an opposite geometry on the carbon atom linked to the hydroxyl group, as well as applanatumols E and F (115, 116, 121, and 122).…”

Section: Meroterpenoids With Two Isoprene Units As Side Chainsmentioning

confidence: 99%

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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“…23). Petchilactone C ( 103 ) 57 from G. petchii is likely a derivative of applanatumol I ( 71 ) due to sharing the same dicyclic lactone function. The two ether rings could be generated by an acetylation between 1-OH, 2′-OH and 9′-CHO.…”

Section: Structure and Hypothetical Biosynthesis Of Gmsmentioning

confidence: 99%

“…(±)-Petchilactone A ( 106 ) and (±)-petchilactone B ( 107 ) with a 6/6/5/5 ring system were obtained from the fruiting bodies of G. petchii . 57 Except for the lactone, their similar 6/6/5 ring systems could be constructed via a nucleophilic addition from C-2′ to C-6′, Wagner–Meerwein rearrangement reaction of 9′-CH 3 from C-7′ to C-6′, and the electrophilic addition of C-2 and C-7′. Different oxidative state could form 106 bearing a 3′ → 9′ γ-lactone or alternatively 107 with an 8′ → 9′ γ-lactone (Fig.…”

Section: Structure and Hypothetical Biosynthesis Of Gmsmentioning

confidence: 99%

Structural diversity, hypothetical biosynthesis, chemical synthesis, and biological activity ofGanodermameroterpenoids

et al. 2023

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Skeletal meroterpenoids from Ganoderma petchii mushrooms that potentially stimulate umbilical cord mesenchymal stem cells

Cited by 8 publications

References 18 publications

Meroterpenoids From Ganoderma lucidum Mushrooms and Their Biological Roles in Insulin Resistance and Triple-Negative Breast Cancer

Meroterpenoids From Ganoderma lucidum Mushrooms and Their Biological Roles in Insulin Resistance and Triple-Negative Breast Cancer

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

Structural diversity, hypothetical biosynthesis, chemical synthesis, and biological activity ofGanodermameroterpenoids

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