Purpurolide A, 5/5/5 Spirocyclic Sesquiterpene Lactone in Nature from the Endophytic Fungus Penicillium purpurogenum

Abstract

Purpurolide A (1), an unprecedent sesquiterpene lactone with a rarely encountered 5/5/5 spirocyclic skeleton, along with two new 6/4/5/5 tetracyclic sesquiterpene lactones (2 and 3), were isolated from the cultures of the endophytic fungus Penicillium purpurogenum IMM003. The structures and absolute configurations of 1–3 were established by spectroscopic analysis, single-crystal X-ray diffraction, and calculations of the 13C NMR and ECD data. Compounds 1–3 showed significant inhibitory activity against pancreatic lipase.

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

“…Pestalustaine A ( 106 ) was isolated from Pestalotiopsis adusta; it is a unique sesquiterpene with an unusual 5/6/7-fused tricyclic ring system, and it exhibited weak-to-moderate cytotoxic activity against the HeLa, HCT-116, and A-549 cell lines [ 71 ]. Purpurolide A ( 107 ), a sesquiterpene lactone isolated from Penicillium purpurogenum , possesses a rarely encountered 5/5/5 spirocyclic skeleton; it displayed potent inhibition against pancreatic lipase [ 72 ]. Among compounds obtained from the culture of Phomopsis sp., phomophyllin A ( 108 ) is the first naturally occurring sesquiterpenoid containing an unusual 2,3- seco -protoilludane carbon scaffold.…”

Biological Activities of Some New Secondary Metabolites Isolated from Endophytic Fungi: A Review Study

“…The biological activity properties of compounds 63-65 were evaluated for inhibitory activity against pancreatic lipase. Compounds 63-65 displayed potent inhibition in the assay with IC 50 values of 2.83 ± 0.52, 5.45 ± 0.69, and 6.63 ± 0.89 µM, respectively, compared to the standard kaempferol (1.50 ± 0.21 µM) [29].…”

“…A new sesquiterpene lactone, namely colletotrin 62 (Figure 2), was obtained from a rice culture of Colletotrichum gloeosporioides, an endophytic fungus isolated from the stem bark of Cameroonian medicinal plant Trichilia monadelpha (Meliaceae) [28]. Purpurolide A 63 (Figure 2), an unprecedent sesquiterpene lactone with a rarely encountered 5/5/5 spirocyclic skeleton, along with two new 6/4/5/5 tetracyclic sesquiterpene lactones purpurolide B and C 64-65 (Figure 2), were isolated from the cultures of the endophytic fungus Penicillium purpurogenum IMM003 [29]. Bioassay-guided fractionation of the crude extract of fermentation broth of one symbiotic strain Fusarium oxysporum ZZP-R1 derived from coastal plant Rumex madaio Makino, one traditional Chinese medicine used as a treatment of inflammation and toxication, yielded one novel compound, fusariumins D 66 (Figure 2).…”

Spirocyclic Motifs in Natural Products

“…Studies of secondary metabolite structures in endophyte fungus Penicillium purpurogenum unveiled a series of unique sesquiterpene lactone compounds ( 35 – 37 ) containing spirocyclic combinations of three five-membered rings (Figure 14). All three compounds were screened against several cancer cell lines (melanoma M14, colon cancer HCT-116, glioma U87, ovary cancer A2780, stomach cancer BG-823, hepatoma Bel-7402, and lung cancer A549) and several pathogenic microorganisms ( Mycobacterium spegmatis (ATCC70084), Staphylococcus aureus (ATCC25923), and Staphylococcus epidermidis (ATC12228)); however, no activity was detected at 50 μM [33].…”