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Meroterpenes from endophytic fungus A1 of mangrove plant Scyphiphora hydrophyllacea.

Mei WL, Zheng B, Zhao YX, Zhong HM, Chen XL, Zeng YB, Dong WH, Huang JL, Proksch P, Dai HF - Mar Drugs (2012)

Bottom Line: Four new meroterpenes, guignardones F-I (1-4), together with two known compounds guignardones A (5) and B (6) were isolated from the endophytic fungus A1 of the mangrove plant Scyphiphora hydrophyllacea.A possible biogenetic pathway of compounds 1-6 was also proposed.All compounds were evaluated for inhibitory activity against methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus aureus.

View Article: PubMed Central - PubMed

Affiliation: Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agriculture Sciences, Haikou 571101, China. meiwenli@itbb.org.cn

ABSTRACT
Four new meroterpenes, guignardones F-I (1-4), together with two known compounds guignardones A (5) and B (6) were isolated from the endophytic fungus A1 of the mangrove plant Scyphiphora hydrophyllacea. Their structures and relative configurations were elucidated by spectroscopic data and single-crystal X-ray crystallography. A possible biogenetic pathway of compounds 1-6 was also proposed. All compounds were evaluated for inhibitory activity against methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus aureus.

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Plausible biosynthetic pathway of 1–6.
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marinedrugs-10-01993-f005: Plausible biosynthetic pathway of 1–6.

Mentions: A possible biogenetic pathway of compounds 1–6 was proposed as shown in Scheme 1. Guignardone A (5), a major product isolated in this experiment, was taken as the biogenetic precursor. Two ether bonds were suitable for the enzymatic opening that resulted in a 3,10-dihydroxy intermediate (i) and a 4,7-dihydroxy intermediate (ii). The five-membered ring and the connected isopropanol group of intermediate i could turn upside-down around the bond C-8–C-9 to generate 1. The intermediate ii underwent an oxidation and decarboxylation to give an intermediate (iii). Afterward, the intermediate (iii) converted to its C-1 ketone isomer. This assumption reasonably accounted for the simultaneous occurrences of β-orientation of OH-6 in 2 and α-orientation of OCH3 in 3.


Meroterpenes from endophytic fungus A1 of mangrove plant Scyphiphora hydrophyllacea.

Mei WL, Zheng B, Zhao YX, Zhong HM, Chen XL, Zeng YB, Dong WH, Huang JL, Proksch P, Dai HF - Mar Drugs (2012)

Plausible biosynthetic pathway of 1–6.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3475268&req=5

marinedrugs-10-01993-f005: Plausible biosynthetic pathway of 1–6.
Mentions: A possible biogenetic pathway of compounds 1–6 was proposed as shown in Scheme 1. Guignardone A (5), a major product isolated in this experiment, was taken as the biogenetic precursor. Two ether bonds were suitable for the enzymatic opening that resulted in a 3,10-dihydroxy intermediate (i) and a 4,7-dihydroxy intermediate (ii). The five-membered ring and the connected isopropanol group of intermediate i could turn upside-down around the bond C-8–C-9 to generate 1. The intermediate ii underwent an oxidation and decarboxylation to give an intermediate (iii). Afterward, the intermediate (iii) converted to its C-1 ketone isomer. This assumption reasonably accounted for the simultaneous occurrences of β-orientation of OH-6 in 2 and α-orientation of OCH3 in 3.

Bottom Line: Four new meroterpenes, guignardones F-I (1-4), together with two known compounds guignardones A (5) and B (6) were isolated from the endophytic fungus A1 of the mangrove plant Scyphiphora hydrophyllacea.A possible biogenetic pathway of compounds 1-6 was also proposed.All compounds were evaluated for inhibitory activity against methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus aureus.

View Article: PubMed Central - PubMed

Affiliation: Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agriculture Sciences, Haikou 571101, China. meiwenli@itbb.org.cn

ABSTRACT
Four new meroterpenes, guignardones F-I (1-4), together with two known compounds guignardones A (5) and B (6) were isolated from the endophytic fungus A1 of the mangrove plant Scyphiphora hydrophyllacea. Their structures and relative configurations were elucidated by spectroscopic data and single-crystal X-ray crystallography. A possible biogenetic pathway of compounds 1-6 was also proposed. All compounds were evaluated for inhibitory activity against methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus aureus.

Show MeSH
Related in: MedlinePlus