Protoilludane-type sesquiterpenoids from Armillaria sp. by co-culture with the endophytic fungus Epicoccumsp. associated with Gastrodia elata

Li, Hongtao; Tang, Lin-Huan; Liu, Tao; Yang, Rui‐Ning; Yang, Ya‐Bin; Zhou, Hao; Ding, Zhong‐Tao

doi:10.1016/j.bioorg.2019.103503

Cited by 30 publications

(30 citation statements)

References 31 publications

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“…YUD 17002 also derived from G. elata in PDB media, including five protoilludane-type sesquiterpenes (14-18) and three aryl esters (19-21) ( Supplementary Fig. S1) (Li et al 2019b). These new compounds were also only detected in co-culture extracts.…”

Section: Fungus-fungus Co-culturementioning

confidence: 99%

Co-culture: stimulate the metabolic potential and explore the molecular diversity of natural products from microorganisms

Peng

Shao

et al. 2021

Mar Life Sci Technol

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Section: Fungus-fungus Co-culturementioning

confidence: 99%

Co-culture: stimulate the metabolic potential and explore the molecular diversity of natural products from microorganisms

Peng

Shao

et al. 2021

Mar Life Sci Technol

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“…and the endophytic fungus Epicoccum sp. [ 51 ]. This co-culture also afforded three other protoilludanes, epicoterpene B ( 43 ), C ( 44 ) and E ( 45 ) ( Figure 9 ).…”

Section: Basidiomycotamentioning

confidence: 99%

“…These included 10-hydroxydihydromelleolide ( 134 ) [ 86 ], A52a ( 135 ) [ 99 ], A52b ( 136 ) [ 99 ], 1- O -formyl-10-dehydroxy-melleolide B ( 137 ) [ 85 ], 10-oxo-melleolide B ( 138 ) [ 85 ], 10-dehydroxymelleolide D ( 139 ) [ 83 ] and armilliphatic A ( 140 ). Structure elucidation of all seven natural products was achieved by NMR spectroscopic analysis [ 51 , 83 , 85 , 86 , 99 ]. The relative configurations of A52b ( 136 ) (also named 10-dehydroxy-melleolide B) and armilliphatic A ( 140 ) were determined by analysis of ROESY data, while those of 1- O -formyl-10-dehydroxy-melleolide B ( 137 ) and 10-oxo-melleolide B ( 138 ) were assigned by biogenetic consideration [ 51 , 85 , 99 ].…”

Section: Basidiomycotamentioning

confidence: 99%

“…Structure elucidation of all seven natural products was achieved by NMR spectroscopic analysis [ 51 , 83 , 85 , 86 , 99 ]. The relative configurations of A52b ( 136 ) (also named 10-dehydroxy-melleolide B) and armilliphatic A ( 140 ) were determined by analysis of ROESY data, while those of 1- O -formyl-10-dehydroxy-melleolide B ( 137 ) and 10-oxo-melleolide B ( 138 ) were assigned by biogenetic consideration [ 51 , 85 , 99 ]. The absolute configurations of 139 and 140 were established by comparison of experimental ECD spectra with those of melleolide D ( 81 ) and TDDFT calculated data, respectively [ 51 , 83 ].…”

Section: Basidiomycotamentioning

confidence: 99%

“…The absolute configurations of 139 and 140 were established by comparison of experimental ECD spectra with those of melleolide D ( 81 ) and TDDFT calculated data, respectively [ 51 , 83 ]. A52a ( 135 ), A52b ( 136 ), 1- O -formyl-10-dehydroxy-melleolide B ( 137 ), 10-oxo-melleolide B ( 138 ) and armilliphatic A ( 140 ) were investigated for cytotoxicity against several cell lines where 138 was found to be non-cytotoxic (IC 50 > 40 µM) [ 51 , 69 , 85 ]. Aryl esters 135 – 137 and 140 exhibited moderate cytotoxicity against HL-60 (IC 50 17.06, 17.79, 14.50, 15.80 µM), SMMC-7721 (IC 50 17.77, 20.90, 23.16, 19.42 µM), A-549 (IC 50 15.89, 16.79, 18.41, 15.93 µM), MCF7 (IC 50 14.10, 16.49, 5.34, 19.22 µM) and SW480 (IC 50 15.70, 17.44, 10.77, 23.03 µM) cell lines [ 51 , 69 , 85 ].…”

Section: Basidiomycotamentioning

confidence: 99%

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A Review of Fungal Protoilludane Sesquiterpenoid Natural Products

2020

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Natural products have been a great source for drug leads, due to a vast majority possessing unique chemical structures. Such an example is the protoilludane class of natural products which contain an annulated 5/6/4-ring system and are almost exclusively produced by fungi. They have been reported to possess a diverse range of bioactivities, including antimicrobial, antifungal and cytotoxic properties. In this review, we discuss the isolation, structure elucidation and any reported bioactivities of this compound class, including establishment of stereochemistry and any total syntheses of these natural products. A total of 180 protoilludane natural products, isolated in the last 70 years, from fungi, plant and marine sources are covered, highlighting their structural diversity and potential in drug discovery.

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5’‐Methoxyarmillane, a Bioactive Sesquiterpenoid Aryl Ester from the Fungus Armillaria ostoyae

Orban,

Eichberg,

Marner

et al. 2024

ChemBioChem

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Higher fungi of the genus Armillaria belonging to the phylum Basidiomycota produce bioactive sesquiterpenoid aryl esters called melleolides. A bioactivity‐guided discovery process led to the identification of the new melleolide 5’‑methoxyarmillane (1) in organic extracts from the mycelium of Armillaria ostoyae. Remarkably, supplementation of rapeseed oil to the culture medium potato dextrose broth increased the production of 1 by a factor of six during the course of the 35 days fermentation. Compound 1 was isolated and its structure elucidated by UHPLC‐QTOF‐HR‐MS/MS and NMR spectroscopy. It showed toxicity against Madin‐Darby canine kidney II (MDCK II, IC50 19.2 mg/mL, 44.1 mM) and human lung cancer Calu‐3 cells (IC50 15.2 mg/mL, 34.9 mM) as well as moderate bioactivity against Mycobacterium tuberculosis (MIC 8 mg/mL, 18.4 mM) and Mycobacterium smegmatis (MIC 16 mg/mL, 36.8 mM), but not against Staphylococcus aureus, Escherichia coli, Candida albicans, and Septoria tritici. No inhibitory effects of 1 against the influenza viruses H3N2, H1N1pdm, B/Malaysia, and B/Massachusetts were observed.

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Protoilludane-type sesquiterpenoids from Armillaria sp. by co-culture with the endophytic fungus Epicoccumsp. associated with Gastrodia elata

Cited by 30 publications

References 31 publications

Co-culture: stimulate the metabolic potential and explore the molecular diversity of natural products from microorganisms

Co-culture: stimulate the metabolic potential and explore the molecular diversity of natural products from microorganisms

A Review of Fungal Protoilludane Sesquiterpenoid Natural Products

5’‐Methoxyarmillane, a Bioactive Sesquiterpenoid Aryl Ester from the Fungus Armillaria ostoyae

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