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Planta Med 2021; 87(03): 225-235
DOI: 10.1055/a-1326-2600
Natural Product Chemistry and Analytical Studies
Original Papers

Resorcylic Acid Lactones Produced by an Endophytic Penicillium ochrochloron Strain from Kadsura angustifolia

Hong Chuan Song
1   School of Energy and Environment Science, Yunnan Normal University, Kunming, Peopleʼs Republic of China
,
Dan Qin
2   Key Laboratory of Eco-environments in Three Gorges Reservoir Region of Ministry of Education, School of Life Sciences, Southwest University, Chongqing, Peopleʼs Republic of China
,
Hai Yang Liu
3   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
,
Jin Yan Dong
2   Key Laboratory of Eco-environments in Three Gorges Reservoir Region of Ministry of Education, School of Life Sciences, Southwest University, Chongqing, Peopleʼs Republic of China
,
Chuan You
2   Key Laboratory of Eco-environments in Three Gorges Reservoir Region of Ministry of Education, School of Life Sciences, Southwest University, Chongqing, Peopleʼs Republic of China
,
Yu Meng Wang
2   Key Laboratory of Eco-environments in Three Gorges Reservoir Region of Ministry of Education, School of Life Sciences, Southwest University, Chongqing, Peopleʼs Republic of China
› Author AffiliationsSupported by: National Natural Science Foundation of China 20762015
Supported by: National Natural Science Foundation of China 31270091
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Abstract

Four new β-resorcylic acid lactones, including penochrochlactone A (2), 4-O-desmethyl-aigialomycin B (4), and penochrochlactones C and D (5 and 6), two compounds isolated from a natural source for the first time, 5α, 6β-acetonide-aigialomycin B (1) and penochrochlactone B (3), together with six known compounds, aigialomycin F (7), aigialomycins A, B, and D (8–10), zeaenol (11), and oxozeaenol (12), were isolated from a mycelial solid culture of the endophytic fungus Penicillium ochrochloron SWUKD4.1850 from the medicinal plant Kadsura angustifolia by sequential purification over silica gel, Sephadex LH-20 column chromatography, and preparative HPLC. Their structures were elucidated by extensive spectroscopic analysis and chemical conversions. In addition, all the new compounds were evaluated for their cytotoxic and antibacterial activities in vitro. Penochrochlactone C (5) displayed moderate cytotoxicity against the HeLa tumor cell line with an IC50 value of 9.70 µM. In the antibacterial assays, compounds 4 – 6 exhibited moderate activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa with MIC values between 9.7 and 32.0 µg/mL.

Key words

Kadsura angustifolia - Schisandraceae - resorcylic acid lactones - Penicillium ochrochloron - cytotoxity - antibacterial activity

Supporting Information

    1H-NMR, 13C-NMR, DEPT, HMQC, HMBC, 1H-1H COSY, ROESY, and HREIMS/(HR)ESIMS spectra of compounds 1 – 6 and 9, and dose-response curves of compound 5 are provided in the Supporting Information.

  • Supporting Information


Publication History

Received: 24 June 2020

Accepted after revision: 23 November 2020

Article published online:
21 December 2020

© 2020. Thieme. All rights reserved.

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