Metabolites from the Mangrove Endophytic Fungus <i>Phomopsis</i> sp. (#zsu‐H76)

Yang, Jianxiang; Xu, Fang; Huang, Caihuan; Li, Jing; She, Zhigang; Pei, Zhong; Lin, Yongcheng

doi:10.1002/ejoc.201000329

Cited by 43 publications

(40 citation statements)

References 8 publications

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“…Thus, where 15 bears a phenolic proton that correlates by HMBC to an aromatic methine, 16 only has phenolic protons correlating to quaternary aromatic carbons. Diaporthochromone B ( 16 ) therefore bears a linear 7/7′ coupled chromone ring system, analogous to the recently reported phomopsis-H76 A ( 17 ) [26]. That diaporthochromone B and phomopsis-H76 A are isomeric is evident from variations in the chemical shifts (Table 2), not all of which can be attributed to solvent effects, and their divergent optical rotations: [α] 20 D (CHCl 3 ) −24.1 and [α] 25 D (MeOH) +20, respectively.…”

Section: Resultssupporting

confidence: 69%

Screening Mangrove Endophytic Fungi for Antimalarial Natural Products

et al. 2013

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We conducted a screening campaign to investigate fungi as a source for new antimalarial compounds. A subset of our fungal collection comprising Chinese mangrove endophytes provided over 5000 lipophilic extracts. We developed an accelerated discovery program based on small-scale cultivation for crude extract screening and a high-throughput malaria assay. Criteria for hits were developed and high priority hits were subjected to scale-up cultivation. Extracts from large scale cultivation were fractionated and these fractions subjected to both in vitro malaria and cytotoxicity screening. Criteria for advancing fractions to purification were developed, including the introduction of a selectivity index and by dereplication of known metabolites. From the Chinese mangrove endophytes, four new compounds (14–16, 18) were isolated including a new dimeric tetrahydroxanthone, dicerandrol D (14), which was found to display the most favorable bioactivity profile.

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Section: Resultssupporting

confidence: 69%

Screening Mangrove Endophytic Fungi for Antimalarial Natural Products

et al. 2013

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“…Although Phomopsis species have been extensively screened in bioassays for metabolite production (Isaka et al 2001;Weber et al 2005;Yang et al 2010) the utilization of chemotypes for species recognition has been limited. Phomodiol, Phomopsolide B and Phomopsichalasin were recognized as potential chemotaxonomic markers in endophytic Phomopsis isolates from woody hosts (Horn et al 1994).…”

Section: More Virulentmentioning

confidence: 99%

The genus Phomopsis: biology, applications, species concepts and names of common phytopathogens

et al. 2011

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The genus Phomopsis (teleomorph Diaporthe) comprises phytopathologically important microfungi with diverse host associations and a worldwide distribution. Species concepts in Phomopsis have been based historically on morphology, cultural characteristics and host affiliation. This paper serves to provide an overview of the current status of the taxonomy in Phomopsis with special reference to biology, applications of various species, species concepts, future research perspectives and names of common pathogens, the latter being given taxonomic reappraisal. Accurate species identification is critical to understanding disease epidemiology and in developing effective control measures for plant diseases. Difficulties in accurate species identification using morphology have led to the application of alternative approaches to differentiate species, including virulence and pathogenicity, biochemistry, metabolites, physiology, antagonism, molecular phylogenetics and mating experiments. Redefinition of Phomopsis/Diaporthe species has been ongoing, and some species have been redefined based on a combination of molecular, morphological, cultural, phytopathological and mating type data. Rapid progress in molecular identification has in particular revolutionized taxonomic studies, providing persuasive genetic evidence to define the species boundaries. A backbone ITS based phylogenetic tree is here in generated using the sequences derived from 46 type, epitype cultures, and vouchers and is presented as a rough and quick identification guide for species of Phomopsis. The need for epitypification of taxonomic entities and the need to use multiple loci in phylogenies that better reflect species limits are suggested. The account of names of phytopathogens currently in use are listed alphabetically and annotated with a taxonomic entry, teleomorph, associated hosts and disease symptoms, including brief summaries of taxonomic and phylogenetic research. Available type culture information and details of gene sequences derived from type cultures are also summarized and tabulated.

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“…In contrast, Lin et al [15] describe for the natural product signals with the same chemical shift but for 11-H a ad oublet of doubletsw itht he coupling constants of 12.5 and 9.5 Hz and for 11-H b ad oublet with the coupling constant of 12.5 Hz. Nevertheless, some minor differences were found in the 1 H-NMR spectra.Thus, the coupling constants for the geminal protons at C-11a re different.…”

mentioning

confidence: 99%

“…Examples of this type of naturalp roductsa re phomopsis-H76A (5)f rom Phomopsis sp. For 5,t he absolute and relative configuration has been published by Lin et al [15] as ent-5,w hereas for 6 neither the relative nor the absolute configuration has been previously established. [16] Both compounds are symmetric homod imers with a2 -2' biaryl axis.…”

mentioning

confidence: 99%

Enantioselective Total Synthesis of Blennolide H and Phomopsis‐H76 A and Determination of Their Structure

Valdomir

Senthilkumar

Ganapathy

et al. 2018

Chemistry A European J

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This work reports on the enantioselective total synthesis of the two dimeric natural chromanone lactones phomopsis-H76 A (5) and blennolide H (6). Both syntheses could be achieved from chromane 11, which was obtained by an enantioselective Wacker-type cyclization with >99 % ee. The dimerization of the corresponding monomers was performed using a palladium-catalyzed Suzuki reaction. Moreover, within this work it was possible to revise the absolute configuration of phomopsis-H76 A and determine the relative as well as absolute configuration of blennolide H.

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Metabolites from the Mangrove Endophytic Fungus Phomopsis sp. (#zsu‐H76)

Cited by 43 publications

References 8 publications

Screening Mangrove Endophytic Fungi for Antimalarial Natural Products

Screening Mangrove Endophytic Fungi for Antimalarial Natural Products

The genus Phomopsis: biology, applications, species concepts and names of common phytopathogens

Enantioselective Total Synthesis of Blennolide H and Phomopsis‐H76 A and Determination of Their Structure

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