A monoacylglyceryltrimethylhomoserine, 21F121-A, containing a branched acyl group from Penicillium glaucoroseum.
LCMS-guided purification
Monoacylglyceryltrimethylhomoserine
Penicillium glaucoroseum
Structure determination
Journal
Journal of natural medicines
ISSN: 1861-0293
Titre abrégé: J Nat Med
Pays: Japan
ID NLM: 101518405
Informations de publication
Date de publication:
Sep 2023
Sep 2023
Historique:
received:
12
07
2023
accepted:
19
07
2023
medline:
31
8
2023
pubmed:
29
7
2023
entrez:
29
7
2023
Statut:
ppublish
Résumé
A new monoacylglyceryltrimethylhomoserine, 21F121-A (1), was isolated from the culture of Penicillium glaucoroseum (21F00121) by LCMS-guided purification. The structure was elucidated by NMR and mass spectrometries. The absolute configuration of the homoserine moiety was analyzed by the ECD spectrum after acid hydrolysis, and the S-configuration of the glycerol moiety was determined based on the spectrum of the 1,2-dibenzoyl derivative after acid hydrolysis. Although a variety of diacylglyceryltrimethylhomoserine is distributed in lower plants and fungi, a limited number of studies on monoacyl derivatives have been reported. This is the fourth sample of monoacylglyceryltrimethylhomoserine discovered from a natural source, and the second sample isolated from a fungus. Compound 1 contains an unusual branched pentaene chain attached at the sn-1 position of glycerol and weakly inhibited the growth of HCT116 cells.
Identifiants
pubmed: 37515675
doi: 10.1007/s11418-023-01735-5
pii: 10.1007/s11418-023-01735-5
doi:
Substances chimiques
Glycerol
PDC6A3C0OX
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
992-997Informations de copyright
© 2023. The Author(s) under exclusive licence to The Japanese Society of Pharmacognosy.
Références
Sato N (1992) Betaine Lipids Bot Mag Tokyo 105:185–197
doi: 10.1007/BF02489414
Dembitsky VM (1996) Betaine ether-linked glycerolipids: chemistry and biology. Prog Lipid Res 35:1–51
doi: 10.1016/0163-7827(95)00009-7
pubmed: 9039425
Huang B, Marchand J, Thiriet-Rupert S, Carrier G, Saint-Jean B, Lukomska E, Moreau B, Morant-Manceau A, Bougaran G, Mimouni V (2019) Betaine lipid and neutral lipid production under nitrogen or phosphorus limitation in the marine microalga Tisochrysis lutea (Haptophyta). Algal Res 40:101506
doi: 10.1016/j.algal.2019.101506
Canãvate JP, Armada I, Riós JL, Hachero-Cruzado I (1992) Exploring occurrence and molecular diversity of betaine lipids across taxonomy of marine microalgae. Phytochemistry 124:68–78
doi: 10.1016/j.phytochem.2016.02.007
Vogel G, Eichenberger W (1992) Betaine lipids in lower plants. Biosynthesis of DGTS and DGTA in Ochromonas danica (Chrysophyceae) and the possible role of DGTS in lipid metabolism. Plant Cell Physiol 33:427–436
Murakami H, Nobusawa T, Hori K, Shimojima M, Ohta H (2018) Betaine lipid is crucial for adapting to low temperature and phosphate deficiency in Nannochloropsis. Plant Physiol 177:181–193
doi: 10.1104/pp.17.01573
pubmed: 29555786
pmcid: 5933114
Künzler K, Eichenberger W (1997) Betaine lipids and zwitterionic phospholipids in plants and fungi. Phytochemistry 46:883–892
doi: 10.1016/S0031-9422(97)81274-5
pubmed: 9375419
Riekhof WR, Naik S, Bertrand H, Benning C, Voelker DR (2014) Phosphate starvation in fungi induces the replacement of phosphatidylcholine with the phosphorus-free betaine lipid diacylglyceryl-N, N, N-trimethylhomoserine. Eukaryot Cell 13:749–757
doi: 10.1128/EC.00004-14
pubmed: 24728191
pmcid: 4054272
Senik SV, Maloshenok LG, Kotlova ER, Shavarda AL, Moiseenko KV, Bruskin SA, Koroleva OV, Psurtseva NV (2015) Diacylglyceryltrimethylhomoserine content and gene expression changes triggered by phosphate deprivation in the mycelium of the basidiomycete Flammulina velutipes. Phytochemistry 117:34–42
doi: 10.1016/j.phytochem.2015.05.021
pubmed: 26057227
Martín J, Crespo G, González-Menéndez V, Pérez-Moreno G, Sánchez-Carrasco P, Pérez-Victoria I, Ruiz-Pérez LM, González-Pacanowska D, Vicente F, Genilloud O, Bills GF, Reyes F (2014) MDN-0104, an antiplasmodial betaine lipid from Heterospora chenopodii. J Nat Prod 77:2118–2123
doi: 10.1021/np500577v
pubmed: 25215605
Koyanagi Y, Kawahara T, Hitora Y, Tsukamoto S (2020) Ukixanthomycin A: a hexacyclic xanthone from the mudflat-derived actinomycete Streptomyces sp. Heterocycles 100:1686–1693
doi: 10.3987/COM-20-14320
Koyanagi Y, Hitora Y, Kawahara T, Tsukamoto S (2021) Peniphilones A and B: azaphilone alkaloids from the endophytic fungus Penicillium maximae. Heterocycles 102:325–332
doi: 10.3987/COM-20-14373
Afifi AH, Kagiyama I, El-Desoky AH, Kato H, Mangindaan REP, de Voogd NJ, Ammar NM, Hifnawy MS, Tsukamoto S (2017) Sulawesins A-C, furanosesterterpene tetronic acids that inhibit USP7, from a Psammocinia sp. marine sponge. J Nat Prod 80:2045–2050
doi: 10.1021/acs.jnatprod.7b00184
pubmed: 28621941
Uzawa H, Nishida Y, Ohrui H, Meguro H (1990) Application of the dibenzoate chirality method to determine the absolute configuration of glycerols and related acyclic alcohols. J Org Chem 55:116–122
doi: 10.1021/jo00288a024
Sadahiro Y, Hitora Y, Tsukamoto S (2021) Colletofragarone A2 and colletoins A-C from a fungus Colletotrichum sp. decrease mutant p53 levels in cells. J Nat Prod 84:3131–3137
doi: 10.1021/acs.jnatprod.1c00913
pubmed: 34854682
Schmid R, Heuckeroth S, Korf A, Smirnov A, Myers O, Dyrlund TS, Bushuiev R, Murray KJ, Hoffmann N, Lu M, Sarvepalli A, Zhang Z, Fleischauer M, Dührkop K, Wesner M, Hoogstra SJ, Rudt E, Mokshyna O, Brungs C, Ponomarov K, Mutabdžija L, Damiani T, Pudney CJ, Earll M, Helmer PO, Fallon TR, Schulze T, Rivas-Ubach A, Bilbao A, Richter H, Nothias LF, Wang M, Orešič M, Weng JK, Böcker S, Jeibmann A, Hayen H, Karst U, Dorrestein PC, Petras D, Du X, Pluskal X (2023) Integrative analysis of multimodal mass spectrometry data in MZmine 3. Nat Biotechnol 41:447–449
doi: 10.1038/s41587-023-01690-2
pubmed: 36859716
Nothias LF, Petras D, Schmid R, Dührkop K, Rainer J, Sarvepalli A, Protsyuk I, Ernst M, Tsugawa H, Fleischauer M, Aicheler F, Aksenov AA, Alka O, Allard PM, Barsch A, Cachet X, Caraballo-Rodriguez AM, Da Silva RR, Dang T, Garg N, Gauglitz JM, Gurevich A, Isaac G, Jarmusch A, Kameník Z, Kang KB, Kessler N, Koester I, Korf A, Le Gouellec A, Ludwig M, Martin HC, McCall LI, McSayles J, Meyer SW, Mohimani H, Morsy M, Moyne O, Neumann S, Neuweger H, Nguyen NH, Nothias-Esposito M, Paolini J, Phelan VV, Pluskal T, Quinn RA, Rogers S, Shrestha B, Tripathi A, van der Hooft JJJ, Vargas F, Weldon KC, Witting M, Yang H, Zhang Z, Zubeil F, Kohlbacher O, Böcker S, Alexandrov T, Bandeira N, Wang M, Dorrestein PC (2020) Feature-based molecular networking in the GNPS analysis environment. Nat Methods 17:905–908
doi: 10.1038/s41592-020-0933-6
pubmed: 32839597
pmcid: 7885687
Tsukamoto S, Yamanokuchi R, Yoshitomi M, Sato K, Ikeda T, Rotinsulu H, Mangindaan REP, de Voogd NJ, van Soest RWM, Yokosawa H (2010) Aaptamine, an alkaloid from the sponge Aaptos suberitoides, functions as a proteasome inhibitor. Bioorg Med Chem Lett 20:3341–3343
doi: 10.1016/j.bmcl.2010.04.029
pubmed: 20451377