Polypropionates from the South African Marine Mollusk <i>Siphonaria oculus</i>

Bromley, Candice L.; Popplewell, Wendy L.; Pinchuck, Shirley C; Hodgson, Alan N.; Davies‐Coleman, Michael T.

doi:10.1021/np2009384

Cited by 12 publications

(10 citation statements)

References 14 publications

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“…889 Investigation of the chemistry of Siphonaria oculus (Eastern Cape, South Africa) afforded new polypropionates 1130-1132. 890 The potential artefactual nature of cyclic products 1130, 1131 and a fourth known polypropionate was suggested when analysis of the crude mucous released from individual molluscs revealed 1 H NMR signals attributable to only 1132 in the extract.…”

Section: Bryozoansmentioning

confidence: 99%

Marine natural products

et al. 2014

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This review covers the literature published in 2012 for marine natural products, with 1035 citations (673 for the period January to December 2012) 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 (1241 for 2012), 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.

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Section: Bryozoansmentioning

confidence: 99%

Marine natural products

et al. 2014

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“…In addition, some structurally related compounds were previously found in other sources, such as siphonarienfuranones isolated from the marine mollusk Siphonaria sp. [ 15 , 16 , 17 ], aglajne-2 from the opisthobranch mollusc Bulla striata [ 18 ], AS-183 from Scedosporium sp. fungi [ 19 ], and the aurafurons A and B from the myxobacteria Stigmatella aurantiaca and Archangium gephyra [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

Actinofuranones D-I from a Lichen-Associated Actinomycetes, Streptomyces gramineus, and Their Anti-Inflammatory Effects

Cao

Liu

et al. 2018

Molecules

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Six new metabolites, actinofuranones D-I (compounds 1–6), were isolated together with three known compounds—JBIR-108 (7), E-975 (8), and E-492 (9)—from a fermentation broth of Streptomyces gramineus derived from the lichen Leptogium trichophorum. The structures of the new compounds 1–6 were established using comprehensive NMR spectroscopic data analysis, as well as UV, IR, and MS data. The anti-inflammatory activity of these isolated compounds were evaluated by examining their ability to inhibit nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophage cells. Compounds 4, 5, 8, and 9 attenuated the production of NO due to the suppression of the expression of nitric oxide synthase (iNOS) in LPS-induced RAW 264.7 cells. Moreover, 4, 5, 8, and 9 also inhibited LPS-induced release of proinflammatory cytokines interleukin-6 (IL-6) and tumor necrosis factor α (TNF-α).

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“…The absolute configuration of them remains unknown. The chemical investigation of two species of South African mollusk Siphonaria led to the discovery of two new linear PPs, (6E,8E,10S,12S)-3-hydroxy-4,6,8,10,12-pentamethylpentadeca-6,8-dien-5-one (5) and (2E,4S,6S,8S)-2,4,6,8-tetramethyl-2-undecenoic acid (6) [8,9]. The stereochemistry of 6 was further elucidated by oxidative degradation.…”

Section: Linear Metabolitesmentioning

confidence: 99%

“…An X-ray diffraction was carried out to confirm its racemic nature by a P-1 space group. 6Z,8E-∆ 8 -Siphonarienfuranone (107) and 6E,8E-∆ 8 -siphonarienfuranone (108) are two new epimers at ∆ 6 produced by the mollusk Siphonaria oculus [8]. In the structures of 107 and 108, a hemiketal moiety was constructed in the 3-furanone ring but the stereochemistry at C-2 was unidentified so far (Figure 15).…”

Section: Furan-related Metabolitesmentioning

confidence: 99%

Natural Polypropionates in 1999–2020: An Overview of Chemical and Biological Diversity

Liu

Zhang

2020

Marine Drugs

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Natural polypropionates (PPs) are a large subgroup of polyketides with diverse structural features and bioactivities. Most of the PPs are discovered from marine organisms including mollusks, fungi and actinomycetes, while some of them are also isolated from terrestrial resources. An increasing number of studies about PPs have been carried out in the past two decades and an updated review is needed. In this current review, we summarize the chemical structures and biological activities of 164 natural PPs reported in 67 research papers from 1999 to 2020. The isolation, structural features and bioactivities of these PPs are discussed in detail. The chemical diversity, bioactive diversity, biodiversity and the relationship between chemical classes and the bioactivities are also concluded.

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Polypropionates from the South African Marine Mollusk Siphonaria oculus

Cited by 12 publications

References 14 publications

Marine natural products

Marine natural products

Actinofuranones D-I from a Lichen-Associated Actinomycetes, Streptomyces gramineus, and Their Anti-Inflammatory Effects

Natural Polypropionates in 1999–2020: An Overview of Chemical and Biological Diversity

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