Synthesis and Evaluation of the Analogues of Penicillide against Cholesterol Ester Transfer Protein

Zhang, Qiao; Deng, Chun‐Lin; Fang, Lisong; Xu, Wenchao; Zhao, Qun; Zhang, Jiange; Wang, Yiping; Lei, Xinsheng

doi:10.1002/cjoc.201200977

Cited by 11 publications

(4 citation statements)

References 44 publications

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“…Through efforts in the study of structureactivity relationship, new relative molecules with improved stability and inhibition effects against CETP have been generated. For instance, penicillide 13 has an IC 50 of 15 nmol/l on CETP and is stable in rat plasma [3,30]. Given the structure similarity, it is intriguing to believe that PB is perhaps applicable for the development of novel CETP/ ACAT inhibitors, for example, by chemical modification.…”

Section: Discussionmentioning

confidence: 99%

A Putative Histone Deacetylase Modulates the Biosynthesis of Pestalotiollide B and Conidiation in Pestalotiopsis microspora

Niu¹,

Hao²,

Hong³

et al. 2015

Journal of Microbiology and Biotechnology

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Fungi of the genus Pestalotiopsis have drawn attention for their capability to produce an array of bioactive secondary metabolites that have potential for drug development. Here, we report the determination of a polyketide derivative compound, pestalotiollide B, in the culture of the saprophytic fungus Pestalotiopsis microspora NK17. Structural information acquired by analyses with a set of spectroscopic and chromatographic techniques suggests that pestalotiollide B has the same skeleton as the penicillide derivatives, dibenzodioxocinones, which are inhibitors of cholesterol ester transfer protein (CETP), and as purpactins A and C', inhibitors of acyl-CoA:cholesterol acyltransferase (ACAT). Strain NK17 can make a fairly high yield of pestalotiollide B (i.e., up to 7.22 mg/l) in a constitutive manner in liquid culture. Moreover, we found that a putative histone deacetylase gene, designated as hid1, played a role in the biosynthesis of pestalotiollide B. In the hid1 null mutant, the yield of pestalotiollide B increased approximately 2-fold to 15.90 mg/l. In contrast, deletion of gene hid1 led to a dramatic decrease of conidia production of the fungus. These results suggest that hid1 is a modulator, concerting secondary metabolism and development such as conidiation in P. microspora. Our work may help with the investigation into the biosynthesis of pestalotiollide B and the development for new CETP and ACAT inhibitors.

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Section: Discussionmentioning

confidence: 99%

A Putative Histone Deacetylase Modulates the Biosynthesis of Pestalotiollide B and Conidiation in Pestalotiopsis microspora

Niu¹,

Hao²,

Hong³

et al. 2015

Journal of Microbiology and Biotechnology

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“…4 Only a few methods exist for the construction of these heterocyclic compounds. For accessing the benzodioxocine motif, non-metallic systems such as Mukaiyama's lactonization (Scheme 1, c) 5 and hexadehydro-Diels-Alder-generated benzynes have been used (Scheme 1, a). 6 Among the metal-Scheme 1 Construction of eight-membered O-heterocyclic rings catalyzed procedures, a palladium-catalyzed intramolecular aryl etherification (Scheme 1, b) 7 and a silver carboxylatepromoted lactonization (Scheme 1, a) 8 were proposed to construct the 8-membered heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Triton B-promoted regioselective intramolecular addition of enolates to tethered ynamides for the construction of 8-membered O-heterocycles

et al. 2022

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“…Given the fact that the analog bakuchiol shows various biological activities, we have put ∆ 3 -2-hydroxybakuchiol into our natural product-based drug discovery program [27,28,29,30]. Recently, a facile asymmetric synthesis of ∆ 3 -2-hydroxybakuchiol was established and the compound was tested for antiosteoporosis effects [31,32].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of ∆3-2-Hydroxybakuchiol Analogues and Their Growth Inhibitory Activity against Rat UMR106 Cells

Zhao

Shan

et al. 2014

Molecules

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A series of ∆ 3 -2-hydroxybakuchiol analogues have been synthesized and tested for their growth inhibitory activity against rat UMR106 cells by using the MTT method. Some of them exhibit enhanced activities compared with the natural product, and the preliminary SAR profile shows that the chain tail on the natural product could be subtly modified to enhance the activity and the aromatic moiety or the terminal olefin on the main chain can also be modified without any evident loss of activity. The stereo-configuration of the quaternary chiral center has an important influence on the activity.

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Synthesis and Evaluation of the Analogues of Penicillide against Cholesterol Ester Transfer Protein

Cited by 11 publications

References 44 publications

A Putative Histone Deacetylase Modulates the Biosynthesis of Pestalotiollide B and Conidiation in Pestalotiopsis microspora

A Putative Histone Deacetylase Modulates the Biosynthesis of Pestalotiollide B and Conidiation in Pestalotiopsis microspora

Triton B-promoted regioselective intramolecular addition of enolates to tethered ynamides for the construction of 8-membered O-heterocycles

Synthesis of ∆3-2-Hydroxybakuchiol Analogues and Their Growth Inhibitory Activity against Rat UMR106 Cells

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