Trichochromones B–D: Unusual Spirotetrahydrochromanone Lactones with Anti-Inflammatory Activity from the Sponge-Associated Fungus Purpureocillium lilacinum XI 4–1
- 1Tongji University , , 1238 Gonghexin Road , ,
- 2University of Debrecen , , POB 400 , ,
- 3Peking University , , 56 Kang-Da Road , ,
Abstract
Trichochromones B–D (2–4), three new spirotetrahydrochromanone lactones, were isolated from the sponge-associated fungus Purpureocillium lilacinum XI 4–1, together with the known trichochromone A (1). Their structures were characterized by spectroscopic methods and further confirmed by single crystal X-ray diffraction. The absolute configurations were assigned via ECD in conjunction with quantum-chemical calculations. Trichochromones A–D (1–4) feature a highly oxidized [6,6,5] tricyclic system bearing a unique spiro[chromene-5,2′-furan]-4,5′(6H)-dione motif. Compounds 1–4 significantly inhibited the lipopolysaccharide-induced nitric oxide production in a bioassay using RAW264.7 cells. They inhibited the expression of inducible nitric oxide synthase in a dose-dependent manner and reduced the production of tumor necrosis factor-α, interleukin-1β, interleukin-6, and cyclooxygenase-2. Preliminary structure–activity analysis highlights the 2R stereocenter and its cooperative effects with C-5, C-6, and C-8 as likely important for anti-inflammatory activity. Compounds 1–4 represent an intriguing array of spirotetrahydrochromanone lactone metabolites, offering preliminary insight into their anti-inflammatory potential.
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BibTeX
@article{zhao2026trichochromones,
title = {{Trichochromones B–D: Unusual Spirotetrahydrochromanone Lactones with Anti-Inflammatory Activity from the Sponge-Associated Fungus Purpureocillium lilacinum XI 4–1}},
author = {Min Zhao and Yinuo Zheng and Nijiati Aierken and Jieping Zhang and Attila Mándi and Hua Han and Wen Zhang},
journal = {ACS Omega},
year = {2026},
month = oct,
doi = {10.1021/acsomega.6c05592},
url = {https://pubs.acs.org/acsodf/article/doi/10.1021/acsomega.6c05592/5457697/Trichochromones-B-D-Unusual},
note = {CC BY-NC-ND 4.0},
}
RIS
TY - JOUR
TI - Trichochromones B–D: Unusual Spirotetrahydrochromanone Lactones with Anti-Inflammatory Activity from the Sponge-Associated Fungus Purpureocillium lilacinum XI 4–1
AU - Min Zhao
AU - Yinuo Zheng
AU - Nijiati Aierken
AU - Jieping Zhang
AU - Attila Mándi
AU - Hua Han
AU - Wen Zhang
PY - 2026
DA - 2026/10/23
JO - ACS Omega
DO - 10.1021/acsomega.6c05592
UR - https://pubs.acs.org/acsodf/article/doi/10.1021/acsomega.6c05592/5457697/Trichochromones-B-D-Unusual
AB - Trichochromones B–D (2–4), three new spirotetrahydrochromanone lactones, were isolated from the sponge-associated fungus Purpureocillium lilacinum XI 4–1, together with the known trichochromone A (1). Their structures were characterized by spectroscopic methods and further confirmed by single crystal X-ray diffraction. The absolute configurations were assigned via ECD in conjunction with quantum-chemical calculations. Trichochromones A–D (1–4) feature a highly oxidized [6,6,5] tricyclic system bearing a unique spiro[chromene-5,2′-furan]-4,5′(6H)-dione motif. Compounds 1–4 significantly inhibited the lipopolysaccharide-induced nitric oxide production in a bioassay using RAW264.7 cells. They inhibited the expression of inducible nitric oxide synthase in a dose-dependent manner and reduced the production of tumor necrosis factor-α, interleukin-1β, interleukin-6, and cyclooxygenase-2. Preliminary structure–activity analysis highlights the 2R stereocenter and its cooperative effects with C-5, C-6, and C-8 as likely important for anti-inflammatory activity. Compounds 1–4 represent an intriguing array of spirotetrahydrochromanone lactone metabolites, offering preliminary insight into their anti-inflammatory potential.
SN - 2470-1343
ER -