Cephalosporolides H and I,two novel lactones from a marine-derived fungus,penicillium sp.

Two novel lactones, Cephalosporolides H (1) and 1 (2), were isolated from the lyophilized culture broth of the marine-derived fungus, Penicillium sp. The structures were elucidated on the basis of extensive 1D- and 2D-NMR, as well as HRESI-MS spectroscopic analyses. The relative stereochemistries of the compounds were assessed by comparison of the NOESY analysis and spectral data with those in the literature.     

角果木内生真菌的代谢产物研究

目的研究角果木内生真菌Penicillium.sp FJ-1发酵液的化学成分。方法用多种柱色谱技术对该菌发酵液化学成分进行分离纯化,根据波谱数据和理化性质鉴定化合物的结构。结果分离得到5个化合物,经波谱分析鉴定其结构分别为24R-ergosta-7,22-diene-3,5,6-triol(1)、互隔交链孢霉素(2)、5-羟基互隔交链孢霉素(3)、5’-epialtenuene(4)、篮毒菌素黄酮(5)。结论以上5个化合物均为首次从该菌中分离得到,并首次报道了化合物3的核磁数据。     

南极真菌Penicillium sp. S-2-10次级代谢产物的研究

目的 对来源于南极海域海底沉积物（47.09° W,62.05° S,水深1393 m）真菌Penicillium sp. S-2-10的次级代谢产物进行研究。方法 对菌株进行规模发酵,并对所得发酵液的乙酸乙酯萃取浸膏进行系统分离纯化,据化学指征和生物学活性两方面特点,采用Sephadex LH 20凝胶色谱、正相硅胶柱色谱、反相ODS柱色谱、高效液相柱层析等色谱分析方法,通过核磁（1H-NMR和13C-NMR等）及质谱（MS）等波谱分析方法,并与相关文献比较,鉴定化合物结构。 结果 分离得到7个单体化合物,经鉴定化合物1~7分别为Benzoic acid, 2-(2,6-dihydroxybenzoyl)-3-hydroxy-5-(hydroxymethyl)-methyl, methyl ester (1), chrysophanol (2), Volemolide (3), Ergosta-6,8(14),22-trien-3-ol (4), 2-aminophenoxazin-3-one (5), 2-benzothiazolol (6), benzoic acid (7)。结论 化合物3,4为首次从Penicillium属真菌中获得。     

Chemical constituents isolated from the endophytic fungus Penicillium commune

Phytochemical investigation of the endophytic fungus Penicillium communeled to the isolation of nine known compounds.Based on the spectroscopic and chemical properties, their structures were identified as 6-acetyl-2α,5-dihydroxy-2-(2-hydroxypropyl)-3α,8-dimethylchroman (1), communol B (2), communol E (3), communol G (4), 2-hydroxy-4-phenylquinoline (5), viridicatol (6), 3-O-methylviridicatin (7), trans-ferulic acid (8), 1,2-benzenediol,4-(2-methoxyethenyl) (9). Compounds 1 and 5-9 were isolated from this fungus for the first time.     

Two new compounds from the broth of the marine fungus Penicillium griseofulvum Y19-07

Two new compounds, 4-hydroxyphenethyl methyl succinate (1) and 4-hydroxyphenethyl 2-(4-hydroxyphenyl)acetate (2), were isolated from the EtOAc extract of the broth of the marine fungus Penicillium griseofulvum Y19-07. Five known compounds were also obtained in this study. The structures of the new compounds were elucidated by 1D and 2D NMR spectroscopy and mass spectrometry. All of the isolates were evaluated for their scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl free radical by spectroscopic assays. Also, in the cytotoxicity assay of the two new compounds against HL-60 and PC-3 prostate cancer cell lines, compound 2 showed potential activity with an IC₅₀ value of 64.5 μM against human HL-60 cancer cells.     

Three new drimane sesquiterpenoids from cultures of the fungus Penicillium sp.

Three new drimane sesquiterpenoids, 12-hydroxyalbrassitriol (1), drim-8(12)-en-6β,7α, 9α,11-tetraol (2), and drim-68(12)-dien-9α,11-diol (3), along with one known analog albrassitriol (4), were isolated from cultures of the tin mine tailings-associated fungus Penicillium sp. The new structures were determined on the basis of extensive spectroscopic analyses. All compounds were tested for their cytotoxicities against five human cancer cell lines.     

Isocoumarins from the fermentation products of a plant entophytic fungus Penicillium oxalicum

Three new isocoumarins, terrecoumarins A–C (1–3), together with six known isocoumarins (4–9) were isolated from the fermentation products of the fungus Penicillium oxalicum 0403. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. The anti-tobacco mosaic virus (anti-TMV) activities of 1–9 were evaluated. The results revealed that compound 1 showed high anti-TMV activity with inhibition rate 25.4 ± 3.5%. Other compounds also showed weak activity with inhibition rate in the range of 11.3–18.9%.     

荚果蕨植物内生真菌Penicillium sp. SYP-F-7610的抑菌活性次级代谢产物研究

摘要：目的 研究荚果蕨根茎内生真菌Penicillium sp. SYP-F-7610发酵液中抑菌活性次级代谢产物。方法 采用硅胶柱 色谱、ODS柱色谱、反相半制备HPLC等分离菌株发酵液中的次级代谢产物,根据比旋光度和波谱学数据(MS、1H NMR、13C NMR)进行结构鉴定。采用比浊法测试次级代谢产物的抑菌活性。结果 从荚果蕨根茎内生真菌Penicillium sp. SYP-F-7610发 酵液中分离鉴定了7个化合物,分别为青霉酸(1)、3,5,6-三甲基-2,4-二羟基苯甲酸甲酯(2)、苔黑酚(3)、4-羟基苯乙酸甲酯(4)、 6-hydroxy-5-methoxy-3-methyl-3,6-dihydro-2H-pyran-4-carboxylic acid (5)、chermesinone A (6)和(R)-甲羟戊酸内酯(7)。化合物1 对大肠埃希菌(Escherichia coli CMCC44103)、乙型副伤寒沙门菌(Salmonela paratyphi B CMCC50094)、蜡样芽胞杆菌(Bacillus cereus ATCC14579)和肺炎克雷伯菌(Klebsiella pneumoniae CMCC46117)表现出抑制作用,IC50值为3.19~6.79 μg/mL。结论 本文 首次对荚果蕨属植物的内生真菌进行研究,发现荚果蕨根茎内生真菌Penicillium sp. SYP-F-7610的次级代谢产物结构类型丰富、 生物活性多样,值得深入研究。化合物5为首次报道从青霉属真菌次级代谢产物中分离得到。化合物1为首次报道对乙型副伤寒 沙门菌具有抑制活性。     

红树林真菌草酸青霉(092007)的环二肽类成分

目的研究海南文昌红树林真菌草酸青霉(Penicillium oxalicum)的代谢产物,寻找新的抗肿瘤活性化合物。方法利用硅胶、Sephadex LH-20、ODS柱色谱及制备型高效液相色谱等方法进行分离,通过化合物的理化性质及各种波谱技术鉴定它们的结构,采用MTT法评价化合物体外细胞毒活性。结果从真菌菌丝体的丙酮提取物中分离得到6个环二肽类化合物,鉴定其结构分别为:环(苯丙-异亮)二肽[cyclo-(Phe-Ile)](1)、环(苯丙-缬)二肽[cyclo-(Phe-Val)](2)、环(异亮-亮)二肽[cyclo-(Ile-Leu)](3)、环(缬-缬)二肽[cyclo-(Val-Val)](4)、环(脯-缬)二肽[cyclo-(Pro-Val)](5)、环(脯-甘)二肽[cyclo-(Pro-Gly)](6)。体外活性表明:化合物1、3和5在50μg.mL-1下对肝癌细胞HepG-Ⅱ的抑制率分别为31%、32%、17%,对前列腺癌细胞LNCaP抑制率分别为50%、43%、53%。结论这些化合物均为首次从该属真菌的代谢产物中分离得到,其中化合物2、3和5具有一定的细胞毒活性。     

红树植物老鼠簕内生真菌橘青霉P4-5-1中的1个新异喹啉酮生物碱

目的 研究老鼠簕内生真菌橘青霉(Penicillium citrinum)P4-5-1的化学成分。方法 利用正反相硅胶柱色谱、Sephadex LH-20凝胶柱色谱以及半制备高效液相色谱等技术对P4-5-1次生代谢产物进行分离,利用高分辨质谱、一维及二维核磁共振等波谱鉴定技术确定化合物结构。结果 从P4-5-1大米发酵物中分离得到了6个化合物,分别为4-methoxy-2-methylisoquinolin-1(2H)-one (1)、fischexanthone (2)、penicitrinone A (3)、ent-aspergoterpenin C (4)、sydowiol E (5)和citrinin (6)。结论 化合物1为新异喹啉酮生物碱,命名为citrinadin D;化合物2、4和5首次从该种真菌中获得。     

真菌Penicillium sp. DT-F27次级代谢产物及其活性研究

摘要：目的 一株海洋来源真菌Penicillium sp. DT-F27次级代谢产物及其抗肿瘤活性的研究。方法 采用硅胶柱色谱、反相高效液相制备色谱等方法,对该真菌发酵产物的乙酸乙酯提取物进行分离纯化;采用波普解析方法对化合物的结构进行鉴定;采用MTT法测定化合物对人前列腺癌PC-3细胞的抗肿瘤作用。结果 从真菌Penicillium sp. DT-F27的发酵物中分离得到15个化合物,分别为麦角甾醇（1）,dehydrocyclopeptine（2）,3-O-methylviridicatin（3）,verrucofortine（4）,cyclopenin（5）,cyclo(dehydroala-L-Leu)（6）,cyclopenol（7）,4-hydroxy-2-methoxy acetanilide（8）,trans-(3RS,4RS)-3,4-dihydro-3,4,8-trihydroxynaphthalen-1(2H)-one（9）,cyclo(D-Pro-D-Val)（10）,brevianamide F（11）,cyclo(L-Pro-L-Val)（12）,anacine（13）,cyclo(L-Orn-L-Tyr-L-Orn-L-Ala)（14）,cyclo(L-Pro-L-Tyr)（15）。结论 从真菌Penicillium sp. DT-F27的次级代谢产物中分离15化合物,其中麦角甾醇（1）和3-O-methylviridicatin（3）具有较强的抗肿瘤活性,抑制率分别为45.6%和34.8%。     

海洋来源真菌草酸青霉(Penicillium oxalicum)次级代谢产物的分离与鉴定

目的研究海洋来源真菌草酸青霉(Penicillium oxalicum)的次级代谢产物。方法采用重结晶、硅胶柱色谱、Sephadex LH-20柱色谱、开放ODS柱色谱等方法进行分离纯化;根据理化性质及光谱数据确定化合物的结构。结果分离得到10个化合物,分别鉴定为N-acetyl-hydrazinobenzoic acid(1)、N-[2-cis-(4-hydroxyphenyl)ethenyl]formamide(2)、p-hydroxyphenylacetamide(3)、penipanoid A(4)、penipanoid C(5)、2-(4-hydroxybenzyl)quinazolin-4(3H)-one(6)、oxaline(7)、meleagrin(8)、(3R,4R)-3,4,8-trihydroxy-3,4-dihydro-1(2H)-naphthalenone(9)和(3R,4R)-3,4,6,8-tetrahydroxy-3,4-dihydro-1(2H)-naphthalenone(10)。结论化合物1为新天然产物,化合物9、10为首次从青霉属真菌中分离得到。     

黄海葵附生真菌Penicillium thomii的化学成分

目的研究黄海葵(anemone)附生真菌Penicillium thomii的化学成分。方法用各种色谱技术进行分离纯化,根据理化性质和波谱数据进行结构鉴定。结果从黄海葵附生真菌Penicillium thomii菌丝体中分离得到5个化合物,分别为青霉酮A(I),对甲基苯甲酸(II),1-O-十六碳烷酰-2-O-(9-十八碳烯酰)-3-O-(9,12-十八碳二烯酰)甘油酯(III),5α,8α-环二氧-24ζ-甲基胆甾-6,22-二烯-3β-醇(IV)和大黄素(V)。结论青霉酮A(I)为新化合物,化合物II,III,IV和V系首次从该属中分离得到。     

角果木内生真菌Penicillium sp. J54代谢产物及活性研究

目的研究红树植物角果木内生真菌Penicilliumsp.J54产生的活性次生代谢产物。方法采用多种柱色谱技术进行分离纯化,根据化合物的理化常数和波谱数据鉴定结构,利用MTT法测定各化合物的体外细胞毒活性。结果从角果木内生真菌Penicilliumsp.J54发酵液中分离了8个化合物,分别鉴定为:aervecdysteriod D(1)、citroside A(2)、3-methoxyepicoccone(3)、2,4-二羟基-3,5,6-三甲基苯甲醛(4)、mycosphine B(5)、mycosphine A(6)、5-羟甲基糠醛(7)、对羟基苯乙醇(8)。结论其中化合物1~5均为首次从角果木内生真菌分离得到,并首次报道了化合物4的核磁数据,活性测试结果表明化合物3对肿瘤细胞株K-562生长具有抑制作用。     

Griseusin C, and novel quinone derivative from a marine-derived fungusPenicillium sp

A novel quinone derivative, Griseusin C (1), along with a known quinone, Naphthoquinone C (2), was isolated from the lyophilized culture broth of the marine-derived fungus Penicillium sp. The structures were elucidated on the basis of extensive 1 D- and 2D-NMR, as well as HRESI-MS, spectroscopic analysis. The relative stereochemistries of the compounds were assessed by NOESY analysis.     

见血封喉内生真菌Acremonium sp. J1化学成分研究

目的 研究见血封喉内生真菌Acremonium sp. J1发酵液的化学成分。方法 采用多种柱色谱技术对发酵液中的化学成分进行分离纯化,根据波谱数据和理化性质鉴定化合物的结构。结果 分离鉴定了8个化合物,分别为3-(2S,4S-dihydroxypentyl)-6,8-dihydroxyisocoumarin (1)、3-(2S-hydroxy-4-oxopentyl)-6,8-dihydroxy- isocoumarin (2)、(3β,22E)-麦角甾-5,7,22-三烯-3-醇 (3)、(3β,5α,6α,7α,22E)-5,6-环氧麦角甾-8(14),22-二烯-3,7-二醇 (4)、(3β ,5α,6β,22E)-麦角甾-7,22-二烯-3,5,6-三醇 (5)、腺苷 (6)、胸腺嘧啶脱氧核苷 (7)和2-(4-羟苯基)乙酸乙酯 (8)。结论 8个化合物均是首次从见血封喉内生真菌中分离得到。     

(+)-Cyclopenol,a new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid from the fungus Penicillium sclerotiorum endogenous with the Chinese mangrove Bruguiera gymnorrhiza

One new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid named (+)-cyclopenol (1), along with nine known compounds including viridicatol (2), 3-(dimethylaminomethyl)-1-(1,1-dimethyl-2-propenyl)indole (3), anacine (4), aurantiomide C (5), viridicatin (6), 3-O-methylviridicatin (7), verrucosidin (8), ergosterol (9), and ergosterol peroxide (10), was isolated from the EtOAc extract of fungus Penicillium sclerotiorum, an endophytic fungal strain isolated from Chinese mangrove Bruguiera gymnorrhiza. The chemical structure of the new compound 1 was elucidated on the basis of detailed spectroscopic analysis. The absolute configuration of 1 was determined by single-crystal X-ray analysis with Cu Kα radiation (λ = 1.54178 Å). To our knowledge, (+)-cyclopenol (1) represents the first example of 7-membered 2,5-dioxopiperazine isolated from mangrove endophytic fungus.     

Polyketides from the fungus Penicillium decumbens

Two new polyketides, 3,11-dihydroxy-6,8-dimethyldodecanoic acid (1) and trichopyrone B (2), together with two known polyketides, sorbicillin (3) and penicillone A (4), have been isolated from the cultures broth of the fungus Penicillium decumbens. Their structures were elucidated by extensive spectroscopic analysis. All isolated compounds were evaluated for their antibacterial and cytotoxic activities. Of these, compound 3 showed antifungal activity toward Candida albicans Y0109 with a MIC value of 50 μM. Moreover, compounds 3 and 4 exhibited selective cytotoxicity against the human hepatocellular carcinoma (QGY-7703) cell line with the IC₅₀ values of 32.5 and 22.8 μM, respectively.     

A new phenolic enamide and a new meroterpenoid from marine alga-derived endophytic fungus Penicillium oxalicum EN-290

Abstract

Ten secondary metabolites (1–10) including a new phenolic enamide, methyl (Z)-3-(3,4-dihydroxyphenyl)-2-formamidoacrylate (1), and a new meroterpenoid, 15-hydroxydecaturin A (2), were characterized from the EtOAc extracts of the marine alga-derived endophytic fungus Penicillium oxalicum EN-290. The structures of these compounds were elucidated on the basis of 1D and 2D NMR experiments and the absolute configuration of compound 2 was confirmed by electronic circular dichroism quantum calculations. Compound 1 showed potent activity against Staphylococcus aureus with an MIC value of 2.0 μg/ml, which is stronger than that of the positive control (chloromycetin, with an MIC 4.0 μg/ml). This compound also showed activity against harmful algal bloom causative species Nitzschia closterium with inhibition zones of 20, 16, and 10 mm at 20, 10, and 5 mg/ml, respectively. Interestingly, so far, this type of anti-HAB metabolites has only been found in the algal-derived isolate of P. oxalicum. It could probably be a defense of this fungus against environmental stress and threat of survival.     

Two new indole-diterpenoids from the fungus Penicilliumcrustosum YN-HT-15

Two new indole-diterpenoids named penijanthine B and penitrem H (1 and 2) were isolated from the metabolites of the fungus Penicilliumcrustosum YN-HT-15, which was isolated from the red soil of Yunnan Province of China. The structures were determined on spectroscopic analyses and CD spectra.