A comprehensive chemical study of the endophytic fungus Arthrinium sp. ZS03, associated with Acorus tatarinowii Schott, yielded eleven pimarane diterpenoids (compounds 1-11), including seven novel compounds designated arthrinoids A-G (1-7). The determination of their structures and absolute configurations was achieved through extensive spectroscopic techniques, quantum chemical calculations of electronic circular dichroism (ECD), and single-crystal X-ray diffraction analysis. Furthermore, 7 demonstrated inhibitory activity against Klebsiella pneumoniae, comparable to the reference antibiotic amikacin, with a minimum inhibitory concentration (MIC) of 8 μg·mL−1.
| [1] |
Kusari S, Spiteller M. Are we ready for industrial production of bioactive plant secondary metabolites utilizing endophytes?[J]. Nat Prod Rep, 2011, 28(7): 1203-1207.
|
| [2] |
Kusari S, Hertweck C, Spiteller M. Chemical ecology of endophytic fungi: origins of secondary metabolites[J]. Chem Biol, 2012, 19(7): 792-798.
|
| [3] |
Kusari S, Pandey SP, Spiteller M. Untapped mutualistic paradigms linking host plant and endophytic fungal production of similar bioactive secondary metabolites[J]. Phytochemistry, 2013, 91: 81-87.
|
| [4] |
Wang WX, Kusari S, Laatsch H, et al. Antibacterial azaphilones from an endophytic fungus, Colletotrichum sp. BS4[J]. J Nat Prod, 2016, 79(4): 704-710.
|
| [5] |
Gao E, Zhou ZQ, Zou J, et al. Bioactive asarone-derived phenylpropanoids from the rhizome of Acorus tatarinowii Schott[J]. J Nat Prod, 2017, 80(11): 2923-2929.
|
| [6] |
Ye K, Ai HL, Liu JK. Identification and bioactivities of secondary metabolites derived from endophytic fungi isolated from ethnomedicinal plants of Tujia in Hubei Province: a review[J]. Nat Prod Bioprospect, 2021, 11: 185-205.
|
| [7] |
Liu N, Song MN, Zhang QQ, et al. GKK1032B from endophytic Penicillium citrinum induces the apoptosis of human osteosarcoma MG63 cells through caspase pathway activation[J]. Chin J Nat Med, 2022, 20(1): 67-73.
|
| [8] |
Zhu JJ, Huang QS, Liu SQ, et al. Four new diphenyl ether derivatives from a mangrove endophytic fungus Epicoccum sorghinum[J]. Chin J Nat Med, 2022, 20(7): 537-540.
|
| [9] |
Gan D, Li C, Shu Y, et al. Steroids and dihydroisocoumarin glycosides from Xylaria sp. by the one strain many compounds strategy and their bioactivities[J]. Chin J Nat Med, 2023, 21(2): 154-160.
|
| [10] |
Li F, Ye Z, Huang Z, et al. New α-pyrone derivatives with herbicidal activity from the endophytic fungus Alternaria brassicicola[J]. Bioorg Chem, 2021, 117: 105452.
|
| [11] |
Wei PP, Ji JC, Ma XJ, et al. Three new pyrrole alkaloids from the endophytic fungus Albifmbria viridis[J]. Nat Prod Bioprospect, 2022, 12: 5.
|
| [12] |
Gao W, Chai C, He Y, et al. Periconiastone A, an antibacterial ergosterol with a pentacyclo[8.7. 0.01, 5. 02, 14. 010, 15]heptadecane system from Periconia sp. TJ403-rc01[J]. Org Lett, 2019, 21(20): 8469-8472.
|
| [13] |
Hu Z, Ye Y, Zhang Y. Large-scale culture as a complementary and practical method for discovering natural products with novel skeletons[J]. Nat Prod Rep, 2021, 38(10): 1775-1793.
|
| [14] |
Peng X, Chang J, Gao Y, et al. Thiocytochalasins A-D, four sulfur-containing cytochalasans from an endophytic fungus Phoma multirostrata XJ-2-1[J]. Chin Chem Lett, 2022, 33(10): 4572-4576.
|
| [15] |
Li F, Lin S, Zhang S, et al. Alterbrassinoids A-D: fusicoccane-derived diterpenoid dimers featuring different carbon skeletons from Alternaria brassicicola[J]. Org Lett, 2019, 21(45): 8353-8357.
|
| [16] |
Xu K, Zhang X, Chen JW, et al. Anti-inflammatory diterpenoids from an endophytic fungus Phomopsis sp. S12[J]. Tetrahedron Lett, 2019, 60(38): 151045.
|
| [17] |
Guo LF, Liu GR, Liu L. Caryophyllene-type sesquiterpenoids and α-furanones from the plant endophytic fungus Pestalotiopsis theae[J]. Chin J Nat Med, 2020, 18(4): 261-267.
|
| [18] |
Górecki M, Jabłońska E, Kruszewska A, et al. Practical method for the absolute configuration assignment of tert/tert 1,2-diols using their complexes with Mo2(OAc)4 [J]. J Org Chem, 2007, 72(8): 2906-2916.
|
| [19] |
Tsukada M, Fukai M, Miki K, et al. Chemical constituents of a marine fungus, Arthrinium sacchari[J]. J Nat Prod, 2011, 74: 1645-1649.
|
| [20] |
Hu YL, Li XR, Xu G. Carascynol A, a hybrid of caryophyllane-type terpenoid and a C6 unit degraded by polyprenylated acylphloroglucinols from Hypericum ascyron[J]. Nat Prod Bioprospect, 2022, 12: 38.
|
| [21] |
Zhang S, Mo S, Li F, et al. Drimane sesquiterpenoids from a wetland soil-derived fungus Aspergillus calidoustus TJ403-EL05[J]. Nat Prod Bioprospect, 2022, 12: 27.
|
| [22] |
Hou L, Mei CX, Yuan CM, et al. Five new limonoids isolated from Walsura robusta[J]. Nat Prod Bioprospect, 2023, 13(1): 7.
|
| [23] |
Yang B, Su JC, Huang L, et al. Hyperispirones A and B, spiro-bridged polycyclic polyprenylated acylphloroglucinols with antiangiogenesis activity from Hypericum beanii[J]. Org Chem Front, 2022, 9(13): 3460-3466.
|
| [24] |
Wang L, Zhou Z, Huang JP, et al. Strepyrrolins A-E, five pyrrole-sesquiterpene hybrids from Streptomyces sp. KIB 015, revealing a new formation logic of pyrroles by isotope labeling[J]. Org Chem Front, 2023, 10(4): 880-889.
|
| [25] |
Song Y, Tan Y, She J, et al. Tanzawaic acid derivatives from the marine-derived Penicillium steckii as inhibitors of RANKL-induced osteoclastogenesis[J]. J Nat Prod, 2023, 86: 1171-1178.
|
| [26] |
Liu MT, Sun WG, Shen L, et al. Bipolarolides A-G, ophiobolin-derived sesterterpenes with three new carbon skeletons from Bipolaris sp. TJ403-B1[J]. Angew Chem Int Edit, 2019, 58: 12091-12095.
|
| [27] |
Liu M, He Y, Shen L, et al. Bipolarins A-H, eight new ophiobolin-type sesterterpenes with antimicrobial activity from fungus Bipolaris sp. TJ403-B1[J]. Chin J Nat Med, 2019, 17(12): 935-944.
|
| [28] |
Guo ZK, Zhu WY, Zhao LX, et al. New antibacterial depsidones from an ant-derived fungus Spiromastix sp. MY-1[J]. Chin J Nat Med, 2022, 20(8): 627-632.
|
Funding
National Natural Science Foundation of China(82003956)
Henan Young Elite Scientists Sponsorship Program(2023HYTP032)