Two new polyketides from Rhodiola tibetica endophytic fungus Penicillium sp. HJT-A-6
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摘要:
目的：对从西藏红景天茎中分离的内生真菌HJT-A-6中的生物活性化合物进行研究，并评估其化感活性。 方法：采用硅胶、凝胶柱色谱和半制备高效液相色谱进行分离纯化。通过综合波谱分析和计算圆二色谱（ECD）鉴定化合物的结构。此外，通过研究红景天种子的萌发率，对化合物1的化感作用进行了评价。 结果：从青霉菌HJT-A-6 中分离得到两个新的聚酮类化合物4-hydroxy-3,6-dimethyl-2H-pyran-2-one (1)和penilactone E (2)，以及六个已知化合物：walterolactone A (3), 5-hydroxyhexan-4-olide (4), 3-methyl-2-penten-5-olide (5), chaetoquadrin F (6), (Z)-6-acetyl-3-(1,2-dihydroxypropylidene)-5-hydroxy-8-methylchroman-2-one (7), 4-hydroxy-3-(4-hydroxyhexanoyl)-5-methylfuran-2(5H)-one (8)。化合物1在浓度为 0.001 mg/mL 时对红景天种子萌发起促进作用，但在0.01 mg/mL和0.1 mg/mL浓度下抑制红景天种子的萌发。与阳性药物 6-苄氨基嘌呤（6-BA）相比，化合物1能够延长红景天的种子的发芽周期，发芽周期延长至11天。 结论：从红景天内生真菌HJT-A-6 中分离得到两个新化合物。化合物1表现出类植物激素样活性，在高浓度时抑制宿主植物的种子萌发，在低浓度时促进宿主植物的种子萌发。这些结果不仅丰富了红景天内生真菌代谢产物的化学成分，还为理解红景天内生真菌与宿主植物之间的相互作用机制提供了理论基础。
Abstract:
Objective: To study bioactive compounds from the endophytic fungus Penicillium sp. HJT-A-6 isolated from stem of Rhodiola tibetica, and evaluate its allelopathic activity. Methods: The chemical constituents were isolated and purified by silica gel, Sephadex LH-20 column chromatography and semi-preparative HPLC. Their structures were elucidated by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculations. In addition, the allelopathic activity of compound 1 was evaluated by measuring the seed germination rate of R. tibetica. Results: Two new polyketides 4-hydroxy-3,6-dimethyl-2H-pyran-2-one (1) and penilactone E (2), together with six known compounds walterolactone A (3), 5-hydroxyhexan-4-olide (4), 3-methyl-2-penten-5-olide (5), chaetoquadrin F (6), (Z)-6-acetyl-3-(1,2 -dihydroxypropylidene)-5-hydroxy-8-methylchroman-2-one (7) and 4-hydroxy-3-(4-hydroxyhexanoyl)-5-methylfuran-2(5H)-one (8) were isolated from Penicillium sp. HJT-A-6. Compound 1 showed moderate seed-germination-promoting activity at a concentration of 0.001 mg/mL while inhibiting the seed germination at concentrations of 0.1 and 0.01 mg/mL. Compared with the positive drug 6-benzyladenine (6-BA), compound 1 could extend the seed-germination period of R. tibetica (up to 11 d). Conclusion: Two new compounds were isolated from R. tibetica endophytic fungus Penicillium sp. HJT-A-6. Compound 1 displayed plant hormone-like activity, which inhibited the seed germination of the host plant at high concentrations and promoted the seed germination of the host plant at low concentrations. The results not only enrich the chemical constituents of the endophytic fungi isolated from Rhodiola tibetica, but also provide a theoretical basis for understanding the interaction mechanism between Rhodiola tibetica endophytic fungi and the host plant.
关键词:
红景天;青霉菌;聚酮化合物;种子发芽促进活性;结构表征
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This work was supported by Central Government Guided Local Science and Technology Development Fund Project (No. XZ202101YD0017C) and International Science and Technology Cooperation Project of Dalian Science and Technology Innovation Fund (No. 2022JJ12WZ059).
Dongliang Xiao a,, Xiaobao Li a,, Xuemei Zhang a, Nan Jiang a, Dunzhu Luosang b, Weixing Feng a, Xuan Lu a,*, Baomin Feng a,*. Two new polyketides from Rhodiola tibetica endophytic fungus Penicillium sp. HJT-A-6[J]. Chinese Herbal Medicines (CHM),2025,17(2):404-408
