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11 pages, 3588 KB

Open AccessArticle

Chemical Constituents of the Deep-Sea-Derived Penicillium citreonigrum MCCC 3A00169 and Their Antiproliferative Effects

by Zheng-Biao Zou, Gang Zhang, Yu-Qi Zhou, Chun-Lan Xie, Ming-Min Xie, Lin Xu, You-Jia Hao, Lian-Zhong Luo, Xiao-Kun Zhang, Xian-Wen Yang and Jun-Song Wang

Mar. Drugs 2022, 20(12), 736; https://doi.org/10.3390/md20120736 - 24 Nov 2022

Cited by 9 | Viewed by 3573

Abstract

Six new citreoviridins (citreoviridins J–O, 1–6) and twenty-two known compounds (7–28) were isolated from the deep-sea-derived Penicillium citreonigrum MCCC 3A00169. The structures of the new compounds were determined by spectroscopic methods, including the HRESIMS, NMR, ECD calculations, and dimolybdenum tetraacetate-induced CD (ICD) experiments. Citreoviridins J−O (1–6) are diastereomers of 6,7-epoxycitreoviridin with different chiral centers at C-2–C-7. Pyrenocine A (7), terrein (14), and citreoviridin (20) significantly induced apoptosis for HeLa cells with IC₅₀ values of 5.4 μM, 11.3 μM, and 0.7 μM, respectively. To be specific, pyrenocine A could induce S phase arrest, while terrein and citreoviridin could obviously induce G0-G1 phase arrest. Citreoviridin could inhibit mTOR activity in HeLa cells. Full article

(This article belongs to the Special Issue Bioactive Compounds from the Deep-Sea-Derived Microorganisms)

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10 pages, 1172 KB

Open AccessCommunication

Whole Genome Analysis Revealed the Genes Responsible for Citreoviridin Biosynthesis in Penicillium citreonigrum

by Takumi Okano, Naoki Kobayashi, Kazuki Izawa, Tomoya Yoshinari and Yoshiko Sugita-Konishi

Toxins 2020, 12(2), 125; https://doi.org/10.3390/toxins12020125 - 15 Feb 2020

Cited by 8 | Viewed by 4565

Abstract

Citreoviridin (CTV) is a mycotoxin that is produced by Aspergillus terreus, Eupenicillium ochrosalmoneum and Penicillium citreonigrum, and CTV has been detected in a wide range of cereal grains throughout the world. Furthermore, it is especially a serious problem in regions where rice is consumed as a staple food. Moreover, CTV is a well-known yellow rice toxin, and outbreaks of beriberi have occurred due to consumption of rice that is contaminated by CTV even in the recent years. Although CTV biosynthetic genes of A. terreus have been described, those of P. citreonigrum remain unclear, which is concerning since P. citreonigrum is the main cause of CTV contamination in rice. In the present study, we determined the draft genome of the P. citreonigrum strain IMI92228 and revealed the presence of all four genes that form a gene cluster and that are homologous to the CTV biosynthesis genes of A. terreus. The expression of these four homologous genes were highly correlated with CTV production, suggesting that they may play an important role in CTV biosynthesis in P. citreonigrum. We concluded that the gene cluster is a CTV biosynthesis cluster of P. citreonigrum. The findings will contribute to the understanding of the biosynthetic pathway of CTV and will ultimately lead to improvements in the CTV management of agricultural products. Full article

(This article belongs to the Special Issue Mycotoxins and Mycotoxin Producing Fungi: Genetic and Toxicity Aspects)

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16 pages, 2097 KB

Open AccessFeature PaperArticle

The In Vivo and In Vitro Toxicokinetics of Citreoviridin Extracted from Penicillium citreonigrum

by Yosuke Uchiyama, Masahiko Takino, Michiko Noguchi, Nozomi Shiratori, Naoki Kobayashi and Yoshiko Sugita-Konishi

Toxins 2019, 11(6), 360; https://doi.org/10.3390/toxins11060360 - 20 Jun 2019

Cited by 9 | Viewed by 4561

Abstract

Citreoviridin (CTVD), a mycotoxin called yellow rice toxin, is reported to be related to acute cardiac beriberi; however, its toxicokinetics remain unclear. The present study elucidated the toxicokinetics through in vivo experiments in swine and predicted the human toxicokinetics by comparing the findings to those from in vitro experiments. In vivo experiments revealed the high bioavailability of CTVD (116.4%) in swine. An intestinal permeability study using Caco-2 cells to estimate the toxicokinetics in humans showed that CTVD has a high permeability coefficient. When CTVD was incubated with hepatic S9 fraction from swine and humans, hydroxylation and methylation, desaturation, and dihydroxylation derivatives were produced as the predominant metabolites. The levels of these products produced using human S9 were higher than those obtained swine S9, while CTVD glucuronide was produced slowly in human S9 in comparison to swine S9. Furthermore, the elimination of CTVD by human S9 was significantly more rapid in comparison to that by swine S9. These results suggest that CTVD is easily absorbed in swine and that it remains in the body where it is slowly metabolized. In contrast, the absorption of CTVD in humans would be the same as that in swine, although its elimination would be faster. Full article

(This article belongs to the Special Issue Mycotoxins and Mycotoxin Producing Fungi: Genetic and Toxicity Aspects)

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12 pages, 3618 KB

Open AccessArticle

Occurrence of Penicillium brocae and Penicillium citreonigrum, which Produce a Mutagenic Metabolite and a Mycotoxin Citreoviridin, Respectively, in Selected Commercially Available Rice Grains in Thailand

by Nozomi Shiratori, Naoki Kobayashi, Phitsanu Tulayakul, Yoshitsugu Sugiura, Masahiko Takino, Osamu Endo and Yoshiko Sugita-Konishi

Toxins 2017, 9(6), 194; https://doi.org/10.3390/toxins9060194 - 15 Jun 2017

Cited by 22 | Viewed by 9602

Abstract

Commercially available rice grains in Thailand were examined to isolate the monoverticillate Penicillium species responsible for toxic yellowed rice. Penicillium species were obtained from seven out of 10 rice samples tested. Among them, one Penicillium citreonigrum isolate and six Penicillium brocae isolates were morphologically identified. The P. citreonigrum isolate produced the mycotoxin citreoviridin on a yeast extract sucrose broth medium. Mycotoxin surveys showed that citreoviridin was not detected in any samples, but one out of 10 rice samples tested was positive for aflatoxin B₁ at a level of 5.9 μg/kg. An Ames test revealed that methanol extracts from rice grains inoculated with selected P. brocae isolates were positive for strains TA100 and YG7108 of Salmonella typhimurium, suggesting the presence of base-pair substitution and DNA alkylation mutagens. Our data obtained here demonstrated that aflatoxin B₁ and toxic P. citreonigrum were present on domestic rice grains in Thailand, although limited samples were tested. Penicillium brocae, which may produce mutagenic metabolites, was isolated for the first time from the surface of Thai rice grains. Full article

(This article belongs to the Section Mycotoxins)

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