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Chemical constituents of the endophytic fungus Fusarium proliferatum from Ligusticum chuanxiong Hort. (PDF)

Chinese Journal of Applied & Environmental Biology[ISSN:1006-687X/CN:51-1482/Q]

2021 05
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Chemical constituents of the endophytic fungus Fusarium proliferatum from Ligusticum chuanxiong Hort.
KUANG Qixuan1 TAN Lu1 LUO Yu2 FENG Dan1 ZHOU Yu1 GUO Dale1 REN Bo1? & DENG Yun1?
1 Key Laboratory of Standardization of Chinese Herbal Medicine of Ministry of Education, State Key Laboratory Breeding of Systematic Research Development and Utilization of Chinese Medical Resources, Co-founded by Sichuan Province and Ministry of Science and Technology, Pharmacy Department, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China 2 School of Pharmacy, Southwest Medical University, Luzhou 646000, China
Ligusticum chuanxiong Hort. endophytic fungus Fusarium proliferatum chemical constituent cytotoxicity

This study examined the secondary metabolites of the endophytic fungus Fusarium proliferatum from Ligusticum chuanxiong Hort. and their cytotoxicity against three tumor cell lines. Twenty-three compounds were isolated and purified from the ethyl acetate extract of the fermentation broth via column chromatography, medium-pressure reversed-phase silica gel column chromatography, preparative HPLC, and other methods. Their structures were elucidated based on comprehensive spectroscopic analyses. The compounds were identified as follows: 7-oxo-β-Sitosterol (1), 7-oxo-β-stigmasterol (2), ergosterol peroxide (3), 9,11-dehydroergosterol peroxide (4), 5α,6α-epoxy-3β-hydroxyergosta-22-ene-7-one (5), 5α,6α-epoxy-3β,8β,14α-Trihydroxy-5α-ergost-22E-en-7-one (6), 3β-hydroxy-(22E,24R)-ergosta-5,8,22-trien-7-one (7), (4S,17R)-4-hydroxy-17-methylincisterol (8), (3β,5α,6β,22E)-ergosta-7,22-diene-3,5,6-triol (9), beauvericin (10), 4-hydroxybenzaldehyde (11), cyclo-(L-prolyl-L-glycine) (12), cyclo-(Gly-D-Phe) (13), cyclo-(2-hydroxy-Pro-Gly) (14), cyclo-(L-Phe-Ala) (15), 9-octadecenoic acid (Z)-,2’,3’-dihydroxypropyl ester (16), cyclo-(8α-hydroxy-D-prolyl-L-phenylalanine) (17), cyclo-(8β-hydroxy-L-prolyl-D-phenylalanine) (18), cyclo-(8α-hydroxy-L-prolyl-L-phenylalanine) (19), cyclo-(L-Pro-L-Leu) (20), cyclo-(L-Pro-D-Phe) (21), cyclo-(L-Pro-L-Phe) (22), and bassiatin (23). The MTT method was used to evaluate the cytotoxicity of compounds 1–7 and 10 against the MV4-11, HCT116, and HGC-27 cell lines. The results showed that compounds 3 and 5 demonstrated inhibitory activity against the MV4-11 cell lines, with IC50 values of 31.73 ± 2.08 and 14.81 ± 1.89 μmol/L, respectively. Compounds 4 and 10 showed significant inhibitory activity against the MV4-11, HCT116, and HGC-27 cell lines; the IC50 values of compound 4 were 22.87 ± 2.41, 29.58 ± 1.96 and 48.85 ± 2.05 μmol/L, respectively, while those for compound 10 were 4.94 ± 1.17, 3.81 ± 1.62 and 10.06 ± 1.49 μmol/L, respectively. The compounds isolated were mainly steroids and cyclic dipeptides. Compounds 1–9, 13–15, and 17–22 were isolated from the fermentation of Fusarium proliferatum for the first time. Studies of the diversity of the chemical structure of the secondary metabolites of F. proliferatum has been expanded to include research exploring the mechanism of interaction between Ligusticum chuanxiong Hort and endophytic fungi based on the transmission of chemical signals.


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