Guanacastane-type diterpenoids with cytotoxic activity from Coprinus plicatilis

Liu, Yuanzhen; Li, Yaoyao; Ou, Yixin; Xiao, S. Y.; Chen, Lu; Zheng, Zhuo; Shen, Yuemao

doi:10.1016/j.bmcl.2012.06.006

Cited by 20 publications

(13 citation statements)

References 21 publications

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“…Terpenoid-derived spirocyclic furans are reported to induce apoptosis in a range of cancers, with IC 50 values in the low micromolar range. 30 Other fused-ring furans have shown biological activity for a range of diseases. 31 …”

Section: Resultsmentioning

confidence: 99%

FINO2 initiates ferroptosis through GPX4 inactivation and iron oxidation

et al. 2018

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Ferroptosis is a non-apoptotic form of regulated cell death caused by the failure of the glutathione-dependent lipid-peroxide-scavenging network. FINO2 is an endoperoxide-containing 1,2-dioxolane that can initiate ferroptosis selectively in engineered cancer cells. We investigated the mechanism and structural features necessary for ferroptosis initiation by FINO2. We found that FINO2 requires both an endoperoxide moiety and a nearby hydroxyl head group to initiate ferroptosis. In contrast to previously described ferroptosis inducers, FINO2 does not inhibit system xc− or directly target GPX4, as do erastin and RSL3, respectively, or deplete GPX4 protein, as does FIN56. Instead, FINO2 causes both indirect loss of GPX4 enzymatic function and directly oxidizes iron, ultimately causing widespread lipid peroxidation. These findings suggest that endoperoxides such as FINO2 can initiate a multi-pronged mechanism of ferroptosis.

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Section: Resultsmentioning

confidence: 99%

FINO2 initiates ferroptosis through GPX4 inactivation and iron oxidation

et al. 2018

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“…Radianspene C 112 showed inhibitory activity against human breast carcinoma (MDA-MB-435) cell with an IC 50 value of 0.91 μM [ 139 ]. Investigation of secondary metabolites from the fungal Coprinus plicatilis led to the discovery of several new guanacastane-type diterpenoids, named plicatilisins A–D 123 – 126 [ 140 ] and E–H 127 – 130 [ 141 ]. In vitro cytotoxic activities against the human cancer cell lines (HepG2, HeLa, MDA-MB-231, BGC-823, HCT 116, and U2OS) showed that plicatilisin A 123 exhibited significant cytotoxicity with IC 50 values ranging from 1.2 to 6.0 μM [ 140 ].…”

Section: Guanacastanementioning

confidence: 99%

Diterpenes Specially Produced by Fungi: Structures, Biological Activities, and Biosynthesis (2010–2020)

Zhang

Feng

2022

JoF

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Fungi have traditionally been a very rewarding source of biologically active natural products, while diterpenoids from fungi, such as the cyathane-type diterpenoids from Cyathus and Hericium sp., the fusicoccane-type diterpenoids from Fusicoccum and Alternaria sp., the guanacastane-type diterpenoids from Coprinus and Cercospora sp., and the harziene-type diterpenoids from Trichoderma sp., often represent unique carbon skeletons as well as diverse biological functions. The abundances of novel skeletons, biological activities, and biosynthetic pathways present new opportunities for drug discovery, genome mining, and enzymology. In addition, diterpenoids peculiar to fungi also reveal the possibility of differing biological evolution, although they have similar biosynthetic pathways. In this review, we provide an overview about the structures, biological activities, evolution, organic synthesis, and biosynthesis of diterpenoids that have been specially produced by fungi from 2010 to 2020. We hope this review provides timely illumination and beneficial guidance for future research works of scholars who are interested in this area.

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“…We are also interested in the synthesis of alkaloids using novel synthetic processes, three of which include iheyamine B, 4 bufoserotonin C 5 and spiroindimicin B 6 (Figure 1, B). In our medicinal chemistry research, we are involved in the development of novel antibiotics through selective inhibition of the bacterial enzyme pyruvate kinase 7 and we are also exploring ways small molecules can inhibit tumor metastasis processes. Incorporating biomass-derived building blocks during the synthesis of fine and commodity chemicals 8 is also under investigation.…”

Section: Synform Your Research Group Is Active In the Areas Of Organimentioning

confidence: 99%

Synform Issue 2015/2

Zanda¹

2015

Synthesis

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C o n TA C T Yo ur op ini on ab ou t Sy nf or m is we lco me , ple as e co rre sp on d if yo u lik e: ma rk et ing @t hie me -c he mi str y.c omThis document was downloaded for personal use only. Unauthorized distribution is strictly prohibited. Dear readers,Although this Editorial will be published in the February issue of Synform, the truth is that I am writing it soon after the Christmas and New Year celebrations, which I have spent in Italy. Like most of you, I have eaten and drunk way too much and I suspect I have put on quite some weight as a consequence of the many lunches and dinners with relatives and friends. Now I am facing a period whereby I will necessarily have to keep my gastronomic exuberance under control, which doesn't make me too happy… Let's try to put aside food and drinks for a while then, and focus on something else, if possible. Let's concentrate on good chemistry, such as that described in this new issue of Synform. We start with a novel fluorination procedure discovered by D. Carbon-fluorine bond construction has consistently been of great interest to chemists due to the unique characteristics of fluorinated molecules and the synthetic challenges connected with the introduction of fluorine into organic molecules. Apart from the ipso-fluorination of pre-functionalized substrates, C-H bond fluorination is a prospective alternative and has received a great deal of attention in recent years. However, several challenges, for example, relatively harsh conditions, excess amounts of fluorinating agents (oxidants), narrow substrate scopes and poor selectivity still need to be addressed for this emerging area. Given the broad application of fluorinated compounds in pharmaceuticals, agrochemicals and materials, a mild and versatile C-H bond fluorination protocol is highly desirable. Very recently, a novel and facile nitrate-promoted regioselective fluorination of aromatic and olefinic sp 2 -C-H bonds under mild conditions was described by Professors Dan-Qian Xu and Zhen-Yuan Xu, and Dr. Shao-Jie Lou from Zhejiang University of Technology (P. R. of China).Generally, the fluorination reactions took place under very mild conditions (close to room temperature in most cases). strength of both C-H and C-F bonds, so we were delighted to find that the current palladium-nitrate catalytic system enabled the process in a much milder manner." "A catalytic amount of simple, non-toxic and cheap potassium nitrate served as a highly efficient promoter," said Professor D.-Q. Xu. "Actually, silver nitrate was found to be an efficient additive for this transformation at the outset of this program," she explained. Since silver salts were demonstrated to be incorporated in several C-F bond formation reactions, various silver salts were then screened. However, only silver nitrate and silver nitrite could successfully promote the reaction, whereas other silver salts were ineffective. Professor Z.-Y. Xu said: "The unique counter-anion effect led us to hypo thesize that the nitrate anion might be the pivotal promoter. To...

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Guanacastane-type diterpenoids with cytotoxic activity from Coprinus plicatilis

Cited by 20 publications

References 21 publications

FINO2 initiates ferroptosis through GPX4 inactivation and iron oxidation

FINO2 initiates ferroptosis through GPX4 inactivation and iron oxidation

Diterpenes Specially Produced by Fungi: Structures, Biological Activities, and Biosynthesis (2010–2020)

Synform Issue 2015/2

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