Fused multicyclic polyketides with a two-spiro-carbon skeleton from mangrove-derived endophytic fungus <i>Epicoccum nigrum</i> SCNU-F0002

Yan, Zhangyuan; Li, Jialin; Ye, Geting; Chen, Tao; Li, Meimei; Liang, Yanmin; Long, Yuhua

doi:10.1039/d0ra05532h

Cited by 7 publications

(8 citation statements)

References 33 publications

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“…8 | Additional examples for anticipated natural products and suspected natural products awaiting cofirmation. a | iso-epicolactone (92) [75,76] , (+)brevianamide Y (93), [77][78][79] (±)-desoxyisobruceol (94) [80][81][82][83] , and (-)-prehalenaquinone (95) [84] are additional examples for molecules that were synthesized in the laboratory prior to their isolation. b | Cases of anticipated natural products that await isolation from natural sources: 8-epi-isoaplydactone (96), [85] dia-angiopterlactone B (97), [86] biyouyanagin C (98), [87] epi-pycnanthuquinone C (99), [88] 8-epi-homodimericin A (100), [89] intricarene side-product (101), [90] protected dia-millingtonine (102) [91] , diaincargranine B aglycone (103) [92] , diastereomer towards neonectrolides (104) [93] , preuisolactone precursor (105) [94] , nuphar alkaloid isomer (106) [95] , side-product towards (+)-norcembrene 5 (107) [96] , monolomaiviticin A (108) [97] , 2-epilankacyclinol (109) [98] , 3,7-epi-massadine (110) [99] , santarubin S (111) [100] , epiguajadial B (112) [101] , Δ 23,24 -perovskone (113) [102] , epi-pungiolide A (114) [103] , and iso-aspergilasine A (115) [104] .…”

Section: Discussionmentioning

confidence: 99%

Natural product anticipation through synthesis

2022

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Natural product synthesis remains one of the most vibrant and intellectually rewarding areas of chemistry, although the justifications for pursuing it have evolved over time. In the early years, the emphasis lay on structure elucidation and confirmation through synthesis, as exemplified by the celebrated studies on cocaine, morphine, strychnine and chlorophyll. This was followed by a phase where the sheer demonstration that highly complex molecules could be recreated in the laboratory in a rational manner was enough to justify the economic expense and intellectual agonies of a synthesis. Since then, syntheses of natural products have served as platforms for the demonstration of elegant strategies, for inventing new methodology "on the fly", or to demonstrate the usefulness and scope of methods established with simpler molecules. We now add another aspect that we find fascinating, viz. "Natural Product Anticipation". In this review, we survey cases where the synthesis of a compound in the laboratory has preceded its isolation from Nature. The focus of our review lies on examples where this anticipation of a natural product has triggered a successful search or where synthesis and isolation occurred independently. Finally, we highlight cases where such a possibility has been suggested but not yet confirmed, inviting further collaborations between synthetic and natural product chemists. The total synthesis of natural products has always been a major factor in the development of organic chemistry. The reasons for pursuing it have evolved as the field has progressed. In its early history, total synthesis mostly served to confirm the constitution and configuration of readily available natural products. With the advent of X-ray crystallography, NMR spectroscopy, and mass spectrometry, this aspect has become less important, although numerous recent cases exist where the structure of a natural product was settled through total synthesis. [1,2] As a consequence, the emphasis has shifted more toward reaction development and the definition of efficient synthetic strategies. In some cases, the desire to achieve a particular transformation has led to the invention of new reactions or reagents that did not exist before. [3] If a total synthesis is sufficiently efficient, it can also be used to deliver a prized natural product on scale that can otherwise only be procured at great expense or by ignoring environmental concerns. [4] Many other motivations for total synthesis exist, ranging from its value as a training ground for medicinal chemists to the satisfaction that comes with solving the sheer intellectual challenge that it represents. [5,6] In this account, we wish to highlight yet another reason to pursue it: Natural Product Anticipation.In the early days of organic synthesis, there must have been many cases where a compound was prepared in the laboratory and considered "synthetic" that was subsequently identified as a natural product. For instance, Gabriel made aminoacetone (1) in 1893 using his eponymous method. [7,8]...

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Section: Discussionmentioning

confidence: 99%

Natural product anticipation through synthesis

2022

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“…49 As the isomer of benzofuran, compounds of isobenzofuran and its derivatives include 46 metabolites from mangroveassociated fungi. The Epicoccum strain was the source of the isobenzofuran, including 5,6-dihydroxy-7-methoxy-4-methylisobenzofuran-1(3H)-one (282), 49 (+)-epicoccone C ( 283), (À)-epicoccone C ( 284), epicoccone D-F (285-287), 158,159 epicolactone A (288), 158 and a pair of polyketides (AE)-isoepicolactone (289 and 290) with a two-spiro-carbon skeleton. 159 From the Mycosphaerella strain, a new isobenzofuranone dimer, dibefurin B (291), and an isobenzofuranone monomer 292 were isolated.…”

Section: Reviewmentioning

confidence: 99%

“…The Epicoccum strain was the source of the isobenzofuran, including 5,6-dihydroxy-7-methoxy-4-methylisobenzofuran-1(3H)-one (282), 49 (+)-epicoccone C ( 283), (À)-epicoccone C ( 284), epicoccone D-F (285-287), 158,159 epicolactone A (288), 158 and a pair of polyketides (AE)-isoepicolactone (289 and 290) with a two-spiro-carbon skeleton. 159 From the Mycosphaerella strain, a new isobenzofuranone dimer, dibefurin B (291), and an isobenzofuranone monomer 292 were isolated. 160 The Ascomycota strain yielded three new isobenzofuran derivatives, ascomfurans A-C (293-295).…”

Section: Reviewmentioning

confidence: 99%

Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities

et al. 2022

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“…Heterospirocyclic compounds widely exist in various pharmacological agents and agricultural products, and can be used as anticancer, anticonvulsant, and antimicrobial agents. 49 Wang et al reported the synthesis of spiroox-azine derivatives through immobilized CALB-initiated multicomponent reaction from nitrostyrene, cyclohexanone, p-nitrobenzaldehyde, and acetamide substrates, enabling six C-C/C-N bonds and two heterocycles in one-pot operation (►Scheme 17A). 50 When p-nitrobenzaldehyde was replaced by other aromatic aldehydes, the yield was very low.…”

Section: Synthesis Of Other Heterocyclic Compoundsmentioning

confidence: 99%

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

Wang

Shen

et al. 2021

Pharmaceutical Fronts

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Heterocyclic compounds are representative of a larger class of organic compounds, and worthy of attention for many reasons, chief of which is the participation of heterocyclic scaffolds in the skeleton structure of many drugs. Lipases are enzymes with catalytic versatility, and play a key role in catalyzing the reaction of carbon–carbon bond formation, allowing the production of different compounds. This article reviewed the lipase-catalyzed aldol reaction, Knoevenagel reaction, Michael reaction, Mannich reaction, etc., in the synthesis of several classes of heterocyclic compounds with important physiological and pharmacological activities, and also prospected the research focus in lipase-catalyzed chemistry transformations in the future.

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Fused multicyclic polyketides with a two-spiro-carbon skeleton from mangrove-derived endophytic fungus Epicoccum nigrum SCNU-F0002

Abstract: A pair of uncommon fused multicyclic polyketides, (±)-isoepicolactone and one new isobenzofuranone monomer, together with four other known biosynthetically related compounds were isolated from the fermentation of fungus Epicoccum nigrum SCNU-F0002.

Cited by 7 publications

References 33 publications

Natural product anticipation through synthesis

Natural product anticipation through synthesis

Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

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