Antimalarial 9-Methoxystrobilurins, Oudemansins, and Related Polyketides from Cultures of Basidiomycete <i>Favolaschia</i> Species

Kornsakulkarn, Jittra; Palasarn, Somporn; Choowong, Wilunda; Thongpanchang, Tienthong; Boonyuen, Nattawut; Choeyklin, Rattaket; Boonpratuang, Thitiya; Isaka, Masahiko; Thongpanchang, Chawanee

doi:10.1021/acs.jnatprod.9b00647

Cited by 23 publications

(33 citation statements)

References 26 publications

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“…In addition, the acetonide derivative of 8 was used to produce 8a (Figure ). The NOESY correlations of 8a indicated that the protons connected to C-4, C-5, and C-9 are α-oriented. The NOESY correlation of H-8/H-2 revealed the β-orientation of H-2.…”

Section: Resultsmentioning

confidence: 99%

Secondary Metabolites from Annulohypoxylon sp. and Structural Revision of Emericellins A and B

Gan

Wang

et al. 2022

J. Nat. Prod.

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Seven previously undescribed compounds were isolated from the endophytic fungus Annulohypoxylon sp. KYG-19 (family Xylariaceae), including three gymnomitrane-type sesquiterpenes xylariacinols A, B, and D (1, 2, and 4), one bisabolane-type sesquiterpene annulnol F (6), one phenol derivative lariacinol G (7), and two polyhydroxy compounds hypoxylonols H and I (8 and 9), together with two known gymnomitrane-type sesquiterpenes emericellin A (3) and 3gymnomitren-15-ol (5). The assignments of their structures was determined by extensive spectroscopic and spectrometric analysis, acetonide analysis, Mosher's method, and X-ray crystallography. In addition, the structures of emericellins A and B, which were reported to possess an unprecedented tricyclo[4, 4, 2, 1]hendecane scaffold, were revised by comparing their spectroscopic data with those of 1 and 3. Compounds 1 and 4 exhibited antibacterial activity against Escherichia coli with minimum inhibitory concentrations of 4 and 2 μg/mL, respectively.

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Section: Resultsmentioning

confidence: 99%

Secondary Metabolites from Annulohypoxylon sp. and Structural Revision of Emericellins A and B

Gan

Wang

et al. 2022

J. Nat. Prod.

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“…9 The method was also applied successfully with the natural product (5S,6R,Z)-3-methyl-6-phenyl-3-hexene-1,5,6-triol. 10 A good-quality crystal of (R)-THENA-(2S,3S)-butane-2,3-diol was collected. The X-ray diffraction analysis clearly showed the THENA plane and the deshielding zone which affected the chemical shift of the methyl protons of the diol part.…”

Section: Cluster Synlettmentioning

confidence: 99%

“…9 The method was also applied successfully with the natural product (5 S ,6 R , Z )-3-methyl-6-phenyl-3- hexene-1,5,6-triol. 10…”

mentioning

confidence: 99%

Methods for Determination of Absolute Configurations of Chiral Diols by THENA Ester and NMR Shift Difference

Thongpanchang

Dolsophon

Soponpong

et al. 2022

Synlett

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Determination of the absolute configuration of chiral secondary diols by chiral derivatizing agent (CDA) and NMR shift difference is of great challenge due to the complication from the interference of the aromatic anisotropic shielding effect of the two CDAs in close proximity. In this work, tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid (THENA) was introduced as an alternative CDA for diols to overcome such complexity. Since the deshielding effect of THENA is weaker than the shielding effect of other CDAs, THENA would allow the direct analysis of the chemical shift difference in determining the absolute configuration of the chiral diols. In addition, an analytical method based on Riguera’s model could also be used to confirm the assignment. With a good agreement between the assigned configuration based on both analytical models, the absolute configuration of the chiral diols could be assigned with reliability.

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“…manipularis. Kornsakulkarn et al (2019) reported that Favolaschia sp. BCC 1868 and F. Calocera BCC 36684 isolates have 9methoxystrobilurins G,K compounds as antimalarial drugs.…”

Section: Favolaschia Spmentioning

confidence: 99%

Notes Some Macro Fungi From Taman Eden 100, Kawasan Toba, Sumatera Utara, Indonesia: Description and Its Potency

Nurhayat¹,

Putra²,

Anita³

et al. 2021

BES

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Background: The record and research on macrofungi from Taman Eden 100, Toba-Samosir Regency, North Sumatra, Indonesia, was conducted to provide some information about their current status and potential use in the future. Methods: This research was divided into three steps: exploration, identification, and literature studies of the potential use from the identified macrofungi. Results: The research had successfully identified 14 macrofungi that were classified into 4 orders and 9 families. All the macrofungi found were Basidiomycota, namely Gymnopilus sp., Marasmiellus sp.1, Marasmiellus sp.2, Marasmius sp., Favolaschia sp., Coprinellus sp., Coprinopsis sp., Auricularia sp.1, Auricularia sp.2, Auricularia sp.3, Auricularia sp.4, Tylopilus sp., Suillus sp., and Russula sp. The identified macrofungi are potentially used as food supplements, medicine, bio-fertilisers, bioherbicides, and bioremediation agents based on the literature. Conclusions: Taman Eden 100 has a unique fungal diversity of macrofungi and has never been published in a scientific journal. Further investigations are needed to determine the fungal diversity and potential use of macrofungi in other places in Taman Eden 100.

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Antimalarial 9-Methoxystrobilurins, Oudemansins, and Related Polyketides from Cultures of Basidiomycete Favolaschia Species

Cited by 23 publications

References 26 publications

Secondary Metabolites from Annulohypoxylon sp. and Structural Revision of Emericellins A and B

Secondary Metabolites from Annulohypoxylon sp. and Structural Revision of Emericellins A and B

Methods for Determination of Absolute Configurations of Chiral Diols by THENA Ester and NMR Shift Difference

Notes Some Macro Fungi From Taman Eden 100, Kawasan Toba, Sumatera Utara, Indonesia: Description and Its Potency

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