Isolation, ECD assisted structural analyses, biosynthetic discussions, and biological activities of epi-cochlioquinones D and its derivatives

Arayama, Miki; Nehira, Tatsuo; Maeda, Hayato; Tanaka, Kazuaki; Miyagawa, Hisashi; Ueno, Tamio; Hosokawa, Seijiro; Hashimoto, Minoru

doi:10.1016/j.tet.2015.05.044

Cited by 12 publications

(6 citation statements)

References 28 publications

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“…The 1D NMR data (Tables 2 and 3 The configuration at C-3 was suggested to be S, by comparison of the 13 C NMR chemical shifts of C-2 (δC 28.4) and C-28 (δC 12.8). 10,13 This conclusion was further confirmed by the X-ray crystallographic analysis (Figure 4), which allowed an unambiguous assignment of the complete absolute configuration of 7 as 3S,4R,5S,12S,13S,14R,17R,18R,21R with a Flack parameter of 0.024 (6). Accordingly, the structure of 7 was defined and named 4-acetoxy-isocochlioquinone D.…”

Section: ■ Results and Discussionmentioning

confidence: 58%

“…Among them, hexaketide–terpenoid hybrids are relatively rare. Cochlioquinones, one intriguing member of this subclass, are characterized by a polyketide subunit coupled with a modified farnesyl pyrophosphate (FPP) unit. , Since cochlioquinones A and B were isolated from Cochliobolus miyabeanus , and further determined by crystallographic evidence for the first time in 1971, cochlioquinone derivatives have attracted substantial interest from scientists because of their complex molecular architectures and intriguing biological properties. − For instance, anhydrocochlioquinone A exhibited significant activity in inducing apoptosis on HCT116 cells within the range of 10–30 μM, and epi -cochlioquinone A was found to be a promising cholesterol acyltransferase inhibitor with an IC 50 value of 1.7 μM . More recently, Ge’s group in 2018 disclosed a series of cochlioquinones’ polyketide–terpenoid biosynthesis pathways, which employed a pair of PKSs to synthesize 2,4-dihydroxy-6-alkylbenzoic acid, followed by oxidative decarboxylation, farnesyl transfer, and terpene cyclization, finally generating the meroterpenoid skeleton .…”

Section: Introductionmentioning

confidence: 99%

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Bioactive Polyketide-Terpenoid Hybrids from a Soil-Derived Fungus Bipolaris zeicola

et al. 2020

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Nine novel polyketide−terpenoid hybrids (1−9), characterized by a 1-alkylated-3,5-dihydroxyphenyl derivative coupled with a modified farnesyl pyrophosphate (FPP) unit, were isolated from a soil-derived fungus Bipolaris zeicola. Their structures were determined by comprehensive spectroscopic data, single-crystal X-ray diffraction analyses, and electronic circular dichroism calculations. Structurally, compounds 1, 2, 5, and 6 possess a rare thiazole moiety; compounds 3 and 4 are the first examples of meroterpenoids featuring an undescribed 6/6/6/6/5 pentacyclic system and bearing a tetrahydrofuran ring fused to a polyketide and a sesquiterpenoid subunit; compounds 7 and 8 possess a rare 2H-1,4-thiazin-3(4H)-one moiety; and compound 9 represents the first example of meroterpenoid having an unusual thiazol-2(3H)-one moiety. The bioactivity assays revealed that compounds 1, 2, 5, 6, and 9 exhibited a significant immunosuppressive effect against concanavalin A (ConA)-induced T lymphocyte proliferation with IC 50 values ranging from 5.6 to 8.8 μM, and compounds 1, 2, and 4 exhibited moderate cytotoxic activities with IC 50 values ranging from 18.4 to 29.4 μM.

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Section: ■ Results and Discussionmentioning

confidence: 58%

Section: Introductionmentioning

confidence: 99%

Bioactive Polyketide-Terpenoid Hybrids from a Soil-Derived Fungus Bipolaris zeicola

et al. 2020

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“…The structure of cq-9 was compared with other structure of Cochlioquinone such as Cochlioquinone A, B and D. The difference between Cochlioquinone A and Cochlioquionone B is that -OH and -H are bonded to C-12 (R3), and -OCOCH3 and =O are bonded to C-4 (R4), respectively [ 58 ]. Cochlioquionone D is similar to B, but has a double bond of C-2 and C-3 [ 59 ]. The molecular structural of cq-9 is most similar to that of Cochlioquinone A, except that the methyl group is bonded to C-15 (R1) rather than C-14 (R2).…”

Section: Discussionmentioning

confidence: 99%

The Quantitative Trait Loci Mapping of Rice Plant and the Components of Its Extract Confirmed the Anti-Inflammatory and Platelet Aggregation Effects In Vitro and In Vivo

et al. 2021

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Unpredictable climate change might cause serious lack of food in the world. Therefore, in the present world, it is urgent to prepare countermeasures to solve problems in terms of human survival. In this research, quantitative trait loci (QTLs) were analyzed when rice attacked by white backed planthopper (WBPH) were analyzed using 120 Cheongcheong/Nagdong double haploid lines. Moreover, from the detected QTLs, WBPH resistance-related genes were screened in large candidate genes. Among them, OsCM, a major gene in the synthesis of Cochlioquinone-9 (cq-9), was screened. OsCM has high homology with the sequence of chorismate mutase, and exists in various functional and structural forms in plants that produce aromatic amino acids. It also induces resistance to biotic stress through the synthesis of secondary metabolites in plants. The WBPH resistance was improved in rice overexpressed through map-based cloning of the WBPH resistance-related gene OsCM, which was finally detected by QTL mapping. In addition, cq-9 increased the survival rate of caecal ligation puncture (CLP)-surgery mice by 60%. Moreover, the aorta of rat treated with cq-9 was effective in vasodilation response and significantly reduced the aggregation of rat platelets induced by collagen treatment. A cq-9, which is strongly associated with resistance to WBPH in rice, is also associated with positive effect of CLP surgery mice survival rate, vasodilation, and significantly reduced rat platelet aggregation induced by collagen treatment. Therefore, cq-9 presents research possibilities as a substance in a new paradigm that can act on both Plant-Insect in response to the present unpredictable future.

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“…Cochlioquinone B is a sesquiterpene metabolite, an inhibitor of NADH ubiquinone reductase, and a phytotoxic agent that inhibits root growth of finger millet and rice at a 100 ppm concentration [26]. Cochlioquinone D is a physiologically active natural product that inhibits root growth of Lolium multiflorum [41]. Cochlioquinone 9 is distinguished from cochlioquinone A in that C26 (methyl group) is not bound to C14 but is bound to C15.…”

Section: Discussionmentioning

confidence: 99%

Antimicrobial Activity of Chrysoeriol 7 and Chochlioquinone 9, White-Backed Planthopper-Resistant Compounds, Against Rice Pathogenic Strains

Jang

Park

Kim

2020

Biology

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As environmental damage caused by chemical pesticides appears worldwide, eco-friendly agriculture is increasing, and finding eco-friendly pesticide materials has become very important. Chrysoeriol and cochlioquinone, two flavonoids, act as an antibacterial and antioxidant, and increase the resistance of rice to the white-backed planthopper (WBPH). In this experiment, chrysoeriol 7 (C7) and cochlioquinone 9 (C9) were extracted from rice inoculated with the WBPH using MeOH, and cultivars with high extraction efficiency were selected. In addition, the antimicrobial activity of C7 and C9 against various pathogens causing disease in rice was tested. The results show that C7 has antifungal activity against Fusarium graminearum and Pythium graminicola, and C9 show antifungal activity against Cladosporium herbarum, Cladosporium cladosporioides, Gibberella zeae, Fusarium graminearum and Pythium graminicola. When both substances were treated at a concentration of 1000 ppm, they showed high inhibition rates of 62.3% and 36.2% against P.graminicola, respectively. After that, a phylogenetic tree was created to clarify the relationship between the microorganisms whose growth was inhibited and divided into three groups. This result can contribute to the study of biopesticide materials that can control pests and pathogens.

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Isolation, ECD assisted structural analyses, biosynthetic discussions, and biological activities of epi-cochlioquinones D and its derivatives

Cited by 12 publications

References 28 publications

Bioactive Polyketide-Terpenoid Hybrids from a Soil-Derived Fungus Bipolaris zeicola

Bioactive Polyketide-Terpenoid Hybrids from a Soil-Derived Fungus Bipolaris zeicola

The Quantitative Trait Loci Mapping of Rice Plant and the Components of Its Extract Confirmed the Anti-Inflammatory and Platelet Aggregation Effects In Vitro and In Vivo

Antimicrobial Activity of Chrysoeriol 7 and Chochlioquinone 9, White-Backed Planthopper-Resistant Compounds, Against Rice Pathogenic Strains

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