Dioxomorpholines and Derivatives from a Marine-Facultative Aspergillus Species

Abstract

Two new dioxomorpholines, 1 and 2, three new derivatives, 3-5, and the known compound PF1233 B (6) were isolated from a marine-facultative Aspergillus sp. MEXU 27854. Their structures were established by 1D and 2D NMR and HRESIMS data analysis. The absolute configuration of 1 and 2 was elucidated by comparison of experimental and DFT-calculated vibrational circular dichroism spectra. Compounds 3, 5, and 6 were noncytotoxic to a panel of human cancer cell lines with different functional status for the tumor-suppressor protein p53, but were inhibitors of P-glycoprotein-reversing multidrug resistance in a doxorubicin-resistant cell line.

Recent Discovery of Heterocyclic Alkaloids from Marine-Derived Aspergillus Species

“…The rice-based culture of a marine-associated fungal strain A. sp. MEXU 27854 was extensively chromatographed to produce five dioxomorpholine derivatives 6-10 [27]. The structure of compound 11, which was obtained from a marine sediment-derived Aspergillus sp.…”

Insights in Fungal Bioprospecting in Mexico

“…The marine-facultative Aspergillus sp. MEXU 27854 was isolated from sandy soil collected in the intertidal zone located in Caleta Bay, Acapulco, Guerrero, Mexico [61]. The intertidal regions are dynamic environments that support an immense biodiversity.…”

“…The structures of 79-84 were established by 1D and 2D NMR and HRESIMS data analysis, and the absolute configuration of 79 and 80 was elucidated by comparison of experimental and DFT calculated vibrational circular dichroism spectra. Finally, the cytotoxic properties of derivatives 81, 83, and 84 were determined using a panel of human cancer cell lines with different functional status for p53 and against a cell line (A549/doxorubicin) that overexpresses Pgp and presents developed resistance to doxorubicin [61].…”

Absolute configuration of phomactatriene diterpenoids obtained by Wagner‐Meerwein rearrangement of epimeric verticillols

“…Thus, the achievement of this task by VCD is highly desirable in order to strengthen the configurational scenario that supports the biosynthetic relationships of phomactatrienes with verticillanes, taxanes, and phomactins. VCD has been used to assign the AC of many substances, including natural products, by comparison of their calculated and experimental VCD curves …”

“…VCD has been used to assign the AC of many substances, including natural products, by comparison of their calculated and experimental VCD curves. [15][16][17][18][19][20][21] Verticillane-type diterpenes have been isolated from Bursera species, specifically (+)-(1S,3E,7E,11S,12S)verticilla-3,7-dien-12-ol (1) from Bursera suntui and (+)-(1S,3E,7E,11S,12R)-verticilla-3,7-dien-12-ol (2) from Bursera kerberi. 4 The only structural difference between them is the configuration at the C-12 stereogenic center ( Figure 1).…”