A mycophenolic acid derivative from the fungus Penicillium sp. SCSIO sof101

Abstract

Mycophenolic acid (MPA) is a group of metabolite derived from several species of Penicillium, which shows potent bioactivity. In this study, a new derivative of MPA compound named penicacid D (1), was isolated from the marine derived fungus Penicillium sp. SCSIO sof101, along with seven known compounds (2-8). Their structures were elucidated based on the HR-ESI-MS and NMR data. Moreover, the ¹H and ¹³C NMR data of compound 2 and the ¹³C NMR data of compound 3 are reported. Compounds 1, 4 and 6 exhibited weak activities against Escherichia coli (clinical isolation number 100385570) and Acinetobacter baumannii (clinical isolation number 100069).     

A new lactam alkaloid from Portulaca oleracea L. and its cytotoxity

A new lactam alkaloid named oleraciamide D (1), indentified as (5R)-4-(3-methoxy-4-hydroxyphenyl)-5-(4-hydroxyphenyl)-5,6-dihydropyridin-2(1H)-one, together with five known compounds, indole-3-aldehyde (2), portulacatone (3), N-trans-feruloyloctopamine (4), N-trans-feruloyl-3′-O-methyldopamine (5) and N-trans-feruloyltyramine (6) were isolated from Potulaca oleracea L. Among them, indole-3-aldehyde (2) was isolated from the medicine for the first time. The structure of the new alkaloid was elucidated via UHPLC-ESI-Q-TOF/MS, 1D NMR and 2D NMR. The five known compounds were established by comparing the ¹H-NMR and ¹³C NMR with the reported literature. Oleraciamide D (1) showed cytotoxicity against SH-SY5Y cells when concentration at 50 uM by CCK-8 method.     

A new polyoxygenated farnesylcyclohexenone from Fungus Penicillium sp.

A new polyoxygenated farnesylcyclohexenone, peniginsengin A (1), was isolated from the fermentation of Penicillium sp. YIM PH30003, an endophytic fungus associated with Panax notoginseng (Burk.) F. H. Chen. The structure was assigned based on a combination of 1 D and 2 D NMR and mass spectral data. The cytotoxicity and antimicrobial activities of compound 1 were investigated.     

A new dihydroisocoumarin with an isoprenyl group from the endophytic fungus <Emphasis Type="Italic">Cephalosporium</Emphasis> sp.

A new dihydroisocoumarin derivative containing an isoprenyl group, 5-(3'-methylbut-2'-enyloxy)-3,4-dihydro8-hydroxy-3-methylisochromen-1-one (1), was isolated from the mangrove fungus Cephalosporium sp. from the South China Sea. The structure of compound 1 was established by comprehensive analysis of the spectral data, especially 2D NMR spectra.     

Antifungal activity against Botrytis cinerea of labdane-type diterpenoids isolated from the resinous exudate of Haplopappus velutinus Remy (Asteraceae)

Two labdane diterpenoids were isolated, from the resinous exudate of Haplopappus velutinus Remy (Asteraceae); the main compound was identified as 7,13-(E)-labdadien-15,18-dioic-acid-18-methyl ester (1) and the minor compound identified as 7-labden-15,18-dioic-acid-18-methyl ester (2). Their structures were obtained using FTIR, MS, HRMS and NMR data: 1D NMR (¹H, ¹³C and DEPT-135), 2D homonuclear NMR (COSY and NOESY) and heteronuclear NMR (HSQC and HMBC). The trans stereochemistry of the decalin moiety of compounds 1 and 2 was established through NOESY experiments of the reduction product of 1; 7-labden-15,18-diol (1a). Diterpenoids 1 and 1a are described for the first time and showed antifungal activity, inhibiting approximately 40% mycelial growth of Botrytis cinerea.     

A new isochroman derivative from the marine fungus <Emphasis Type="Italic">Phomopsis</Emphasis> sp. (No. ZH-111)

A new isochroman, (3R,4S)-3,4-dihydro-4,5,8-trihydroxy-3-methylisocoumarin (1), and two known compounds were isolated from the marine fungus Phomopsis sp. (No. ZH-111). Their structures were determined by spectroscopic methods, mainly 1D and 2D NMR. Preliminary pharmacological test revealed that compound 1 and exumolide A (3) can accelerate the growth of subintestinal vessel plexus (SIV) branches markedly and compound 2 can inhibit the growth of subintestinal vessel plexus (SIV) branches.     

Terretonin D1, a new meroterpenoid from marine-derived Aspergillus terreus ML-44

A new meroterpenoid, named terretonin D1 (1), and three known ones, terretonin (2), terretonin A (3), and terretonin D (4), were isolated from marine-derived fungus Aspergillus terreus ML-44. The structure of 1 was elucidated by extensive spectroscopic methods, including 1D and 2D NMR, HR-ESI-MS, and the absolute configuration was determined by X-ray crystallographic analysis. The anti-inflammation activity of 1–4 was preliminarily tested, and all of them weakly inhibited the nitric oxide (NO) production of RAW264.7 macrophages stimulated by lipopolysaccharide (LPS), with inhibitory rates of 22–34% at 50?μg/mL.     

(3R,4S)-isostreptenol III from Penicillium purpurogenum MM

Abstract

In continuation of the search for new compounds from the terrestrial fungus Penicillium purpurogenum MM, (3R,4S)-isostreptenol III (1), a further new natural compound is reported. The chemical structure of 1 was confirmed by extensive 1D and 2D NMR and ESI HR mass measurements, and by comparison with literature data. The absolute configuration was determined by ab initio calculations of ECD, ORD, and NMR data. The antimicrobial and cytotoxic activities of the crude extract and 1 were reported using a set of microorganisms and by the brine shrimp assay, respectively.     

3″-Hydroxymethyl-butyrolactone II from Aspergillus sp

Abstract

In continuation of the search for new compounds from the terrestrial fungus Aspergillus sp., one new butyrolactone, 3″-hydroxymethyl-butyrolactone II (1) was isolated. The chemical structure of 1 was confirmed by extensive 1D and 2D NMR and HR-ESI mass data analysis, and by comparison with literature data. The absolute configuration was also determined by ECD calculations.     

Two new acids from mangrove endophytic fungus (No. ZZF13)

Two new acids 1 and 2, together with a known compound, purpactin A (3), were isolated from endophytic fungus No. ZZF13. Their structures were elucidated on the basis of 1D, 2D NMR, and HREIMS spectra. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp.336-337, July-August, 2008. Original articlesubmitted April 24, 2007.     

Westerdijkin A,a new hydroxyphenylacetic acid derivative from deep sea fungus Aspergillus westerdijkiae SCSIO 05233

A new methyl 2-(4-((2-hydroxy-3-methylbut-3-en-1-yl)oxy)phenyl) acetate 1, together with five known compounds 2–6, was isolated from the culture of the deep sea-derived fungus Aspergillus westerdijkiae SCSIO 05233. The new structure was determined by NMR (¹H and ¹³C NMR, HSQC, HMBC and MS) and optical rotation analysis. Compound 5 displayed weak inhibitory activities towards K562 and promyelocytic HL-60 with IC₅₀ values of 25.8 and 44.9 μM, and compound 6 showed strong antifouling activity with EC₅₀ value 8.81 μg/mL.     

Emerixanthone E,a new xanthone derivative from deep sea fungus Emericella sp SCSIO 05240

The marine fungus Emericella sp was isolated from the deep sea sediments. The fungus was identified by its morphology and ITS region. A new emerixanthone E (1) together with four (2–5) known emodin derivatives were isolated from the metabolites of the fungus Emericella SCSIO05240. The structures were elucidated on the basis of NMR spectroscopic analysis and mass spectrometry. The biological properties of those compounds (1–5) were explored for antimicrobial, antifungal and antitumor activity.     

Porric acid D from marine-derived fungus <Emphasis Type="Italic">Alternaria</Emphasis> sp. isolated from Bohai Sea

Porric acid D (1), a new dibenzofuran derivative, was isolated from the methanol extract of a marine-derived fungus, Alternaria sp., isolated from the Bohai Sea, together with a known compound, altenusin. Their structures were elucidated by spectroscopic analysis, including high-resolution mass spectroscopy, and 1 and 2-dimensional NMR techniques. Compounds 1 and 2 showed inhibitory activity against Staphyloccocus aureus with MIC 100 and 25 μg/mL, respectively.     

A novel naphthoquinone from <Emphasis Type="Italic">Plumbago zeylanica</Emphasis> roots

A novel naphthoquinone (1) was isolated from the methanol extract of P. zeylanica roots in addition to a known compound plumbagin (2). Their structures were determined by UV, IR, MS, ¹H, and ¹³C NMR spectroscopic analysis, including 2D NMR.     

Butyrolactones derivatives from the fermentation products of a plant entophytic fungus Penicillium oxalicum

Two new butyrolactone derivatives, terrelactones A and B (1 and 2), together with four known butyrolactone derivatives (3–6), 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 and 2 were evaluated. The results showed that compounds 1 and 2 exhibited high anti-TMV activity with inhibition rates of 25.5% and 27.4%, respectively. The inhibition rate is close to that of positive control (28.9%).     

A new anthraquinone and eight constituents from Hedyotis caudatifolia Merr. et Metcalf: isolation,purification and structural identification

Hedyotis caudatifolia Merr. et Metcalf. (HC), a folk medicine in Yao nationalities areas in China, was used to investigate the chemical constituents. Through silica gel and Sephadex LH-20 column chromatography, nine compounds were isolated and purified. By physical and chemical properties, IR, MS (EI-MS, high resolution EI-MS), 1D NMR (¹H NMR, ¹³C NMR) and 2D NMR (HSQC, ¹H–¹H COSY, HMBC), their structures were identified as β-sitosterol (1), stigmasterol (2), scopolin (3), 2-hydroxy-1,7,8-trimethoxyanthracene-9,10-dione (4), oleanolic acid (5), ursolic acid (6), methyl barbinervate (7), β-daucosterol (8) and p-Hydroxybenzoic acid (9). These compounds were isolated from HC for the first time, and 4 a new anthraquinone whose biological activities are worth to be investigated in future. These compounds may contribute to the HC’s pharmacological effects on treating diseases, and may be used as candidates for control index in establishing the quality control standard of HC.     

A new chromene from the fruiting bodies of Chroogomphus rutilus

A new chromene, acetic acid 2R-(4,8-dimethylnona-3,7-dienyl)-8-hydroxy-2-methyl-2H-chromen-6-yl ester (1), was isolated from the fruiting bodies of Chroogomphus rutilus, together with six known compounds (2–7). The structures of these compounds were identified based on 1D and 2D NMR, including ¹H–¹H COSY, HMQC and HMBC spectroscopic methods. Of these seven compounds, 2 and 3 showed cytotoxicity against HSC-T6, SK-Hep1 and A549 cell lines.     

A new flavane acid from the fruits of Illicium verum

A new compound, illiciumflavane acid (1), along with 13 known compounds (2–14), were isolated from the fruits of Illicium verum Hook. F. Their structures were elucidated through various spectroscopic methods, including 1D NMR (¹H NMR, ¹³C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centres was determined using CD spectrum as well as analyses of coupling constants and optical rotation data. Cytotoxicity evaluation of four compounds showed that illiciumflavane acid and (E)-1,2-bis(4-methoxyphenyl)ethene exhibited potential against A549 activities with IC₅₀ values of 4.63 μM and 9.17 μM, respectively.     

A new minor diketopiperazine from the sponge-derived fungus Simplicillium sp. YZ-11

Chemical investigation of the cultures of a sponge-derived fungus Simplicillium sp. YZ-11 led to the isolation of a new minor diketopiperazine alkaloid cyclo-(2-hydroxy-Pro-Gly) (1) and a natural lactone (S)-dihydro-5-[(S)- hydroxyphenylmethyl]-2(3H)-furanone (2), together with five known ergostane-type sterols (3–7). Their structures were established based on extensive spectroscopic methods (¹H and ¹³C NMR, ¹H-¹H COSY, HSQC and HMBC) and optical rotation analysis.     

Regioselective synthesis and structures of anti-cancer 20(R)-ginsenoside Rg3 derivatives

Abstract

Regioselective synthesis of three novel palmitates of 20(R)-ginsenoside Rg₃ was accomplished via a facile strategy, along with complete assignment of their ¹H and ¹³C NMR resonances by 1D and 2D NMR (¹H-¹H COSY, DEPT 135, HSQC, HMBC, and NOESY) techniques. The derivatives were tested for in vitro anti-proliferative activities against pancreatic cancer PANC-1 cells. Compounds 2, 3, and 4 exhibited more potent activity than did 20(R)-ginsenoside Rg₃.