https://pubs.rsc.org/en/content/articlepdf/2019/NP/C8NP00092A

Marine natural products.

Secondary metabolites of fungi from marine habitats.

Covering: 2010. Previous review: Nat. Prod. Rep., 2011, 28, 196. This review covers the literature published in 2010 for marine natural products, with 895 citations (590 for the period January to December 2010) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1003 for 2010), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

Review: Marine natural products

Jin-Ming Gao,*,† Sheng-Xiang Yang,‡ and Jian-Chun Qin †Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, Department of Chemistry and Chemical Engineering, College of Science, Northwest A&F University, 3 Taicheng Road, Yangling 712100, Shaanxi, China ‡College of Science, Zhejiang A&F University, Lin’an, Hangzhou 311300, Zhejiang, China College of Plant Sciences, Jilin University, Changchun, Jilin 130062, China

Azaphilones: Chemistry and Biology

Summary

Marine bacteria and fungi are of considerable importance as new promising sources of a huge number of biologically active products. Some of these marine species live in a stressful habitat, under cold, lightless and high pressure conditions. Surprisingly, a large number of species with high diversity survive under such conditions and produce fascinating and structurally complex natural products. Up till now, only a small number of microorganisms have been investigated for bioactive metabolites, yet a huge number of active substances with some of them featuring unique structural skeletons have been isolated. This review covers new biologically active natural products published recently (2007–09) and highlights the chemical potential of marine microorganisms, with focus on bioactive products as well as on their mechanisms of action.

Bioactive compounds from marine bacteria and fungi.

Nine new fungal metabolites, one phthalide derivative, acremonide (1), and eight isocoumarin derivatives, acremonones A-H (2-9), were isolated from the mangrove-derived fungus Acremonium sp. PSU-MA70 together with 10 known compounds. Their structures were determined by NMR analysis. The known 8-deoxytrichothecin and trichodermol exhibited moderate antifungal activity against Candida albicans and Cryptococcus neoformanns, respectively.

Phthalide and isocoumarin derivatives produced by an Acremonium sp. isolated from a mangrove Rhizophora apiculata.

Two new azaphilone derivatives, penicilazaphilones A (1) and B (2), and one new isocoumarin, penicilisorin (3), together with six known compounds were isolated from the endophytic fungus Penicillium sclerotiorum PSU-A13. Their structures were identified by analysis of spectroscopic data. The antimicrobial activity against Staphylococcus aureus, Candida albicans and Cryptococcus neoformans as well as the inhibitory effect on human immunodeficiency virus (HIV)-1 integrase and protease were examined.

Azaphilone and isocoumarin derivatives from the endophytic fungus Penicillium sclerotiorum PSU-A13.

Nigrospoxydons A−C (1−3) and nigrosporapyrone (4), four new metabolites, were isolated from the marine-derived fungus Nigrospora sp. PSU-F5 together with nine known compounds. Their structures were elucidated by spectroscopic methods, mainly 1D and 2D NMR spectroscopic techniques. The antibacterial activity against the standard Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus was evaluated.

Epoxydons and a Pyrone from the Marine-Derived Fungus Nigrospora sp. PSU-F5

This study aimed to evaluate the cytotoxicity of a crude extract of Piper cubeba against normal and breast cancer cell lines. To prepare the extract, P. cubeba seeds were ground, soaked in methanol and dichloromethane and isolated by column chromatography. Fractions were tested for cytotoxicity effects on normal fibroblast (L929), normal breast (MCF-12A) and breast cancer cell lines (MCF-7, MDA-MB-468 and MDA-MB-231). The most effective fraction was selected for DNA fragmentation assay to detect apoptotic activity. The results showed that the methanolic crude extract had a higher cytotoxic activity against MDA-MB-468 and MCF-7 than a dichloromethane crude extract. Then, the methanolic crude extract was separated into six fractions, designated A to F. Fraction C was highly active against breast cancer cell lines with an IC50 value less than 4 μg/mL. Therefore, Fraction C was further separated into seven fractions, CA to CG. The 1H-NMR profile showed that Fraction CE was long chain hydrocarbons. Moreover, Fraction CE demonstrated the highest activity against MCF-7 cells with an IC50 value of 2.69 ± 0.09 μg/mL and lower cytotoxicity against normal fibroblast L929 cells with an IC50 value of 4.17 ± 0.77 μg/mL. Finally, DNA fragmentation with a ladder pattern characteristic of apoptosis was observed in MCF-7, MDA-MB-468, MDA-MB-231 and L929 cells, but not in MCF-12A cells.

Cytotoxic activity of Piper cubeba extract in breast cancer cell lines.

Purpose: To investigate the phytochemistry and cytotoxic activity of the leaf, branch and fruit extracts of Vatica diospyroides Symington type LS, an endangered medicinal plant in the peninsula of Thailand. Methods: Extracts of the mature leaves, branches and fruit (both cotyledon and pericarp) of five-year old tree were obtained using various organic solvents. Thin‐layer chromatography (TLC) and phytochemical screening were employed to identify the chemical constituents. Cytotoxicity was characterized by 50 % inhibition (IC 50 ) of human breast cancer cell lines (MCF-7 and MDA-MB-468) using 3-(4,5-dimethylthaizol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Results: The extracts of the plant parts differed in chemical composition. Terpenoids and anthraquinones were present in all extracts, while cardiac glycosides and tannins were isolated from the branches and leaves, respectively. The acetone and methanol extracts of the fruit cotyledons were highly cytotoxic against MDA-MB-468 cell line (IC 50 = 3.1 µg/ml for both extracts), whereas acetone and dichloromethane extracts of the fruit pericarps were highly active against MCF-7 cell line (IC 50 = 18.2 and 21.0 µg/ml, respectively). The other extracts were less active. Conclusion: This work revealed the potentials of V. diospyroides fruit as a cytotoxic agent against human breast cancer cell lines. However, further studies, including identification and purification of the active compounds, will need to be pursued.

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Yaowapa Sukpondma

Papers

Phthalide and isocoumarin derivatives produced by an Acremonium sp. isolated from a mangrove Rhizophora apiculata.

Azaphilone and isocoumarin derivatives from the endophytic fungus Penicillium sclerotiorum PSU-A13.

Epoxydons and a Pyrone from the Marine-Derived Fungus Nigrospora sp. PSU-F5

Cytotoxic activity of Piper cubeba extract in breast cancer cell lines.

Phytochemical Screening and Cytotoxicity of Crude Extracts of Vatica diospyroides Symington Type LS