Journal of Tropical Oceanography >
Bioactive natural compounds from a whale bone-derived fungus Penicillium sp. S2014503
Copy editor: YIN Bo
Received date: 2022-04-11
Revised date: 2022-05-10
Online published: 2022-05-16
Supported by
Key Special Project for Introduced Talents Team of Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou)(GML2019ZD0406)
National Natural Science Foundation of China(81872778)
National Natural Science Foundation of China(41911530078)
National Key R&D Program of China(2018YFC1406705)
National Key R&D Program of China(2018YFC1406704)
Penicillium sp. S2014503 was isolated from a rotten whale bone sample. Constituent analysis and bioactivity evaluation of S2014503 were carried out to find more bioactive compounds from this fungus. Chemical structures of the purified compounds produced by S2014503 were determined by comprehensive analysis of NMR (nuclear magnetic resonance), MS (Mass spectrum) data of each compound. Stereochemistry of chiral compounds were elucidated by comparison of specific rotation value with the reported ones or determined by X-ray diffraction analysis. Ten compounds emodin (1), citreorosein (2), tetrahydro altersolanol B (3), conioxanthone A (4), chrysogine (5), pyramidamycin B (6), germicidin O (7), 2-(6-hydroxy-5,7-dimethylbenzefuranone-4-yl) acetaldehyde (8), astrophenone (9), and chenopodolans A (10) were found in the fermentation product of S2014503 which was cultured on a solid state rice medium. Bioactivities of all the isolated compounds were evaluated for the antibacterial activities and cytotoxicity against brine-shrimp larvae. Compounds 1 and 2 showed weak activity against Gram positive bacteria Micrococcus luteus. Compounds 1, 2 and 4 were significantly cytotoxic against brine-shrimp larvae (Artemia salina) after 6 hours of incubation at room temperature. Interestingly, compound 1 was a well-known laxative ingredient of Traditional Chinese Medicine Rheum officinale and Polygonam cuspidatum. This work is the first report on the emodin analogs from a whale bone derived fungus Penicillium sp.
Key words: Whale bone; Penicillium sp.; emodin
ZHANG Haibo , IMRAN Khan , KUMAR Saurav , ZHANG Liping , FANG Zhuangjie , ZHANG Xinya , PENG Fang , ZHANG Changsheng . Bioactive natural compounds from a whale bone-derived fungus Penicillium sp. S2014503[J]. Journal of Tropical Oceanography, 2023 , 42(2) : 132 -140 . DOI: 10.11978/2022074
表1 化合物3的X-射线晶体数据Tab. 1 Single crystal X-ray diffraction analysis data of compound 3 |
Identification code | Tetrahydroaltersolanol B | Identification code | Tetrahydroaltersolanol B |
---|---|---|---|
Empirical formula | C16H20O6 | μ/mm-1 | 0.971 |
Formula weight | 308.3g·mol-1 | F(000) | 756.0 |
Temperature/K | 100.00 (10) | Crystal size/mm3 | 0.02 × 0.01 × 0.01 |
Crystal system | monoclinic | Radiation/Å | Cu Kα (λ=1.54184) |
Space group | I2 | 2Θ range for data collection/(°) | 4.864 to 148.83 |
a/Å | 7.88690 (10) | Index ranges | -9 ≤ h ≤ 9, -7 ≤ k ≤ 7, -45 ≤ l ≤ 45 |
b/Å | 5.80710 (10) | Reflections collected | 16092 |
c/Å | 36.3377 (4) | Independent reflections | 3323 [Rint=0.0283, Rsigma=0.0195] |
α/(°) | 90 | Data/restraints/parameters | 3323/1/241 |
β/(°) | 90.0340 (10) | Goodness-of-fit on F2 | 1.047 |
γ/(°) | 90 | Final R indexes [I≥2σ (I)] | R1 = 0.0247, wR2 = 0.0640 |
Volume/Å3 | 1664.27 (4) | Final R indexes [all data] | R1 = 0.0254, wR2 = 0.0644 |
Z | 4 | Largest diff. peak/hole / e Å-3 | 0.15/-0.14 |
ρcalc/(g·cm-3) | 1.410 | Flack parameter | -0.06 (5) |
表2 化合物1-10卤虫致死毒性百分率测试结果Tab. 2 Lethal toxicity assay results of compounds 1-10 against Artemia salina |
样品编号 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 阳性对照 |
---|---|---|---|---|---|---|---|---|---|---|---|
致死百分率/% | 97 | 97 | 72 | 90 | 75 | 81 | 90 | 65 | 69 | 61 | 100 |
[1] |
黄筱娟, 陈文豪, 纪明慧, 等, 2015. 菠萝叶的化学成分及生物活性研究[J]. 中草药, 46(7): 949-954.
|
[2] |
王淑玲, 孙云廷, 刘昱霞, 等, 2007. 大黄素的药理学研究近况[J]. 中成药, 29(6): 877-879. (in Chinese)
|
[3] |
徐燕, 田沙沙, 朱华结, 2015. 海洋真菌灰黄青霉Penicillium griseofulvum次级代谢产物中一个新的内酯醛结构[J]. 天然产物研究与开发, 27(4): 559-561.
|
[4] |
杨修伟, 古哲明, 马朝梅, 等, 1998. 从何首乌根中分离的一个新的吲哚衍生物[J]. 中草药, 29(1): 5-11.
|
[5] |
|
[6] |
|
[7] |
|
[8] |
|
[9] |
|
[10] |
|
[11] |
|
[12] |
|
[13] |
|
[14] |
|
[15] |
|
[16] |
|
[17] |
|
[18] |
|
[19] |
|
[20] |
|
[21] |
|
[22] |
|
[23] |
|
[24] |
|
[25] |
|
[26] |
|
[27] |
|
[28] |
|
/
〈 |
|
〉 |