nach oben

Erschienen in:

18.05.2024 | Rapid Communication

Visualizing the spatial distribution of ustalic acid in the fruiting body of Tricholoma kakishimeji

verfasst von: Tetsuro Ito, Syu Taira, Wataru Aoki, Hiroyuki Nagai, Masashi Fukaya, Kaori Ryu, Akiyoshi Yamada

Erschienen in: Journal of Natural Medicines | Ausgabe 4/2024

Einloggen, um Zugang zu erhalten

Abstract

Imaging mass spectrometry (IMS) was conducted for the first time using ustalic acid (UA) and the fruiting body of Tricholoma kakishimeji to localize mushroom toxins. The mushroom materials were systematically collected in Japan, and analysis of the cross sections of the materials at a resolution of 120 μm using matrix-assisted laser desorption/ionization mass spectrometry (MALDI–IMS) revealed the localization of UA and its biogenically related metabolites. MALDI–IMS confirmed that UA was predominantly located on the entire surface of the fruiting body and accumulated in higher amounts in younger fruiting bodies than in mature ones. UA is the first toxic secondary metabolite in the genus Tricholoma locally identified using IMS in mushrooms.

Graphical abstract

Aoki W, Endo N, Ushijima S, Nagai H, Ito T, Fukuda M, Yamada A (2021) Taxonomic revision of the Japanese Tricholoma ustale and closely related species based on molecular phylogenetic and morphological data. Mycoscience 62:307–321. https://doi.org/10.47371/mycosci.2021.06.002CrossRefPubMedPubMedCentral

Yamaura Y (2013) Recent trends of mushroom poisoning in Japan. Chudoku Kenkyu 26:39–43PubMed

Sano Y, Sayama K, Arimoto Y, Inakuma T, Kobayashi K, Koshino H, Kawagishi H (2002) Ustalic acid as a toxin and related compounds from the mushroom Tricholoma ustale. Chem Commun (Camb). https://doi.org/10.1039/b202607dCrossRefPubMed

Sawayama Y, Tsujimoto T, Sugino K, Nishikawa T, Isobe M, Kawagishi H (2006) Syntheses of naturally occurring terphenyls and related compounds. Biosci Biotechnol Biochem 70:2998–3003. https://doi.org/10.1271/bbb.60389CrossRefPubMed

Hayakawa I, Watanabe H, Kigoshi H (2008) Synthesis of ustalic acid, an inhibitor of Na+, K+-ATPase. Tetrahedron 64:5873–5877. https://doi.org/10.1016/j.tet.2008.04.051CrossRef

Ito T, Nagai H, Aoki W, Yamada A, Kawagishi H, Fukaya M, Konishi H (2021) Quantification of ustalic acid, a chemotaxonomic marker, in Tricholoma ustale using liquid chromatography-mass spectrometry. J Nat Med 75:688–691CrossRefPubMed

Taira S, Ikeda R, Yokota N, Osaka I, Sakamoto M, Kato M, Sahashi Y (2010) Mass spectrometric imaging of ginsenosides localization in Panax ginseng root. Am J Chin Med 38:485–493. https://doi.org/10.1142/S0192415X10008007CrossRefPubMed

He F, Huang Y-F, Dai W, Qu X-Y, Lu J-G, Lao C-C, Luo W-H, Sun D-M, Wei M, Xiao S-Y, Xie Y, Liu L, Zhou H (2022) The localization of the alkaloids in Coptis chinensis rhizome by time-of-flight secondary ion mass spectrometry. Front Plant Sci 13:1092643CrossRefPubMedPubMedCentral

Taira S, Yamaguchi N, Morimoto S, Tatsuta Y, Katano H, Ichiyanagi Y, Tsuneyama K, Kikuchi K (2016) Liver disease risk of xenobiotics due to percutaneous absorption revealed by nano-paldi imaging mass spectrometry. Int J Recent Sci Res 7:12589–12592

10.

Tang W, Zhang Y, Li P, Li B (2023) Evaluation of intestinal drug absorption and interaction using quadruple single-pass intestinal perfusion coupled with mass spectrometry imaging. Anal Chem 95:3218–3227CrossRefPubMed

11.

Taira S, Tatsuta Y, Katano H (2017) Localization analysis of natural toxin of Solanum tuberosum L via mass spectrometric imaging. J Cook Sci Japan 50:20–24. https://doi.org/10.11402/cookeryscience.50.20CrossRef

12.

Taira S, Hashimoto M, Saito K, Shido O (2012) Visualization of decreased docosahexaenoic acid in the hippocampus of rats fed an n-3 fatty acid-deficient diet by imaging mass spectrometry. J Biophys Chem 3:221–226CrossRef

13.

Zaima N, Goto-Inoue N, Hayasaka T, Setou M (2010) Application of imaging mass spectrometry for the analysis of Oryza sativa rice. Rapid Commun Mass Spectrom 24:2723–2729. https://doi.org/10.1002/rcm.4693CrossRefPubMed

14.

Taira S, Tokai M, Kaneko D, Katano H, Kawamura-Konishi Y (2015) Mass spectrometry imaging analysis of location of procymidone in cucumber samples. J Agric Food Chem 63:6109–6112. https://doi.org/10.1021/acs.jafc.5b00957CrossRefPubMed

15.

Shiono K, Hashizaki R, Nakanishi T, Sakai T, Yamamoto T, Ogata K, Harada KI, Ohtani H, Katano H, Taira S (2017) Multi-imaging of cytokinin and abscisic acid on the roots of rice (Oryza sativa) using matrix-assisted laser desorption/ionization mass spectrometry. J Agric Food Chem 65:7624–7628. https://doi.org/10.1021/acs.jafc.7b02255CrossRefPubMed

16.

Bhandari DR, Shen T, Rompp A, Zorn H, Spengler B (2014) Analysis of cyathane-type diterpenoids from Cyathus striatus and Hericium erinaceus by high-resolution MALDI MS imaging. Anal Bioanal Chem 406:695–704. https://doi.org/10.1007/s00216-013-7496-7CrossRefPubMed

17.

Huang M-Z, Cheng S-C, Jhang S-S, Chou C-C, Cheng C-N, Shiea J, Popov IA, Nikolaev EN (2012) Ambient molecular imaging of dry fungus surface by electrospray laser desorption ionization mass spectrometry. Int J Mass Spectrom 325:172–182. https://doi.org/10.1016/j.ijms.2012.06.015CrossRef

18.

Wang H, Wang Y (2023) Matrix-assisted laser-desorption/ionization-mass spectrometric imaging of psilocybin and its analogues in psychedelic mushrooms using a cesium chloride-coated target plate. Anal Bioanal Chem 415:735–745. https://doi.org/10.1007/s00216-022-04467-9CrossRefPubMed

19.

Barbosa I, Domingues C, Ramos F, Barbosa RM (2023) Analytical methods for amatoxins: a comprehensive review. J Pharm Biomed Anal. https://doi.org/10.1016/j.jpba.2023.115421CrossRefPubMed

20.

Kawamoto T (2003) Use of a new adhesive film for the preparation of multi-purpose fresh-frozen sections from hard tissues, whole-animals, insects and plants. Arch Histol Cytol 66:123–143. https://doi.org/10.1679/aohc.66.123CrossRefPubMed

Titel: Visualizing the spatial distribution of ustalic acid in the fruiting body of Tricholoma kakishimeji
verfasst von: Tetsuro Ito
Syu Taira
Wataru Aoki
Hiroyuki Nagai
Masashi Fukaya
Kaori Ryu
Akiyoshi Yamada
Publikationsdatum: 18.05.2024
Verlag: Springer Nature Singapore
Erschienen in: Journal of Natural Medicines / Ausgabe 4/2024
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-024-01823-0

Formohyperins G–L, polycyclic prenylated benzoylphloroglucinols from the flowers of Hypericum formosanum

Original Paper

Di-caffeoylquinic acid: a potential inhibitor for amyloid-beta aggregation

Note

Search for new steroidal glycosides with anti-cancer potential from natural resources

Open Access
Review

Anti-coronavirus and anti-pulmonary inflammation effects of iridoids, the common component from Chinese herbal medicines for the treatment of COVID-19

Note

Scutellaria Root extract-induced hepatocytotoxicity can be controlled by regulating its baicalin content

Note

Search for natural products from actinomycetes of the genus Nocardia

Open Access
Review

Springer Medizin

Visualizing the spatial distribution of ustalic acid in the fruiting body of Tricholoma kakishimeji

Abstract

Graphical abstract

Weitere Artikel der Ausgabe 4/2024

Formohyperins G–L, polycyclic prenylated benzoylphloroglucinols from the flowers of Hypericum formosanum

Di-caffeoylquinic acid: a potential inhibitor for amyloid-beta aggregation

Search for new steroidal glycosides with anti-cancer potential from natural resources

Anti-coronavirus and anti-pulmonary inflammation effects of iridoids, the common component from Chinese herbal medicines for the treatment of COVID-19

Scutellaria Root extract-induced hepatocytotoxicity can be controlled by regulating its baicalin content

Search for natural products from actinomycetes of the genus Nocardia

Springer Medizin

Abstract

Graphical abstract

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

Formohyperins G–L, polycyclic prenylated benzoylphloroglucinols from the flowers of Hypericum formosanum

Di-caffeoylquinic acid: a potential inhibitor for amyloid-beta aggregation

Search for new steroidal glycosides with anti-cancer potential from natural resources

Anti-coronavirus and anti-pulmonary inflammation effects of iridoids, the common component from Chinese herbal medicines for the treatment of COVID-19

Scutellaria Root extract-induced hepatocytotoxicity can be controlled by regulating its baicalin content

Search for natural products from actinomycetes of the genus Nocardia