Lanostane triterpenoids, spiro-astraodoric acid, and astraodoric acids E and F, from the edible mushroom Astraeus odoratus

Srisurichan, Suphongphan; Piapukiew, Jittra; Puthong, Songchan; Pornpakakul, Surachai

doi:10.1016/j.phytol.2017.05.020

Cited by 14 publications

(4 citation statements)

References 21 publications

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“…showed a negative Cotton effect at about 310 nm, suggesting the 9S configuration of 2. 14 Thus, the absolute configuration of 2 was determined as 3S, 5R, 7S, 9S, 10S, 13R, 14R, 17R, 20R, 21R, 24R. Compound 3 had a molecular formula of C 31 H 50 O 4 based on the HRESIMS peak m/z 487.3785 [M + H] + (calcd for C 31 H 51 O 4 487.3782).…”

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confidence: 68%

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Spiroinonotsuoxotriols A and B, Two Highly Rearranged Triterpenoids from Inonotus obliquus

Ying

Tong

et al. 2020

Org. Lett.

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Spiroinonotsuoxotriols A (1) and B (2), two highly rearranged pentacyclic triterpenoids featuring a novel 7(8 → 9)abeo-21,24-cyclo-lanostane skeleton, together with their proposed precursors 3–5, were isolated from the sclerotia of the white-rot fungus Inonotus obliquus. Their structures including the absolute configurations were elucidated by extensive spectroscopic analyses and single-crystal X-ray diffraction. The biogenetic pathway of 1 and 2 was proposed. Compounds 1 and 2 exhibited potent α-glucosidase inhibitory activity as compared with the positive control acarbose.

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confidence: 68%

“…In view of the close biosynthetic relationship, the circular dichroism (CD) spectra of 1 and 2 were compared. As shown in Figure , both 1 and 2 showed a negative Cotton effect at about 310 nm, suggesting the 9 S configuration of 2 . Thus, the absolute configuration of 2 was determined as 3 S , 5 R , 7 S , 9 S , 10 S , 13 R , 14 R , 17 R , 20 R , 21 R , 24 R .…”

mentioning

confidence: 84%

Spiroinonotsuoxotriols A and B, Two Highly Rearranged Triterpenoids from Inonotus obliquus

Ying

Tong

et al. 2020

Org. Lett.

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“…Spiro-astraodoric acid ( 264), a lanostane-type triterpenoid with a spirocyclic structure, was discovered in Astraeus odoratus, exhibiting cytotoxicity against various cancer cell lines [181]. Spirosacraoic acid A (265), with a rearranged tirucallane skeleton, was isolated from Boswellia sacra [182].…”

Section: B-nor Steroids and Triterpenoids Derived From Terrestrial So...mentioning

confidence: 99%

Naturally Occurring Nor-Steroids and Their Design and Pharmaceutical Application

Dembitsky

2024

Preprint

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The main focus of this review is to introduce readers to the fascinating class of lipid molecules known as norsteroids, exploring their distribution across various biotopes and their biological activities. The review provides an in-depth analysis of various modified steroids, including A, B, C, and D-norsteroids, each characterized by distinct structural alterations. These modifications, which range from the removal of specific methyl groups to changes in the steroid core, result in unique molecular architectures that significantly impact their biological activity and therapeutic potential. The discussion on A, B, C, and D-norsteroids sheds light on their unique configurations and how these structural modifications influence their pharmacological properties. The review also presents examples from natural sources that produce a diverse array of steroids with distinct structures, including the aforementioned A, B, C, and D-nor variants. These compounds, sourced from marine organisms like sponges, soft corals and starfish, as well as terrestrial entities such as plants, fungi, and bacteria. The exploration of these steroids encompasses their biosynthesis, ecological significance, and potential medical applications, highlighting a crucial area of interest in pharmacology and natural product chemistry. The review emphasizes the importance of researching these steroids for drug development, particularly in addressing diseases where conventional medications are inadequate or for conditions lacking sufficient therapeutic options. Examples of norsteroid synthesis are provided to illustrate the practical applications of this research.

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“…Given the increasing global demand for bioproducts associated with sustainable production, studies on fungi and its enzymes, particularly those that have potential for biotechnological application, have increased (Troiano et al, 2020). In this respect, gasteroid fungi (Basidiomycota) are recognized as important (Wang et al, 2014;Badshah et al, 2015;Srisurichan et al, 2017) for being able to produce several substances such as phenoloxidaseenzymes (PO) (Santana et al, 2016). PO have wide application in pollutantdegradation, effluent discoloration, wood pulp bleaching, removal of phenolics from wines, dyes oxidation, enzymatic conversion of chemical intermediates, biofuels production, xenobiotics degradation and bioremediation (Valmaseda et al, 1990;Banerjee and Vohra, 1991;D'Souza et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

Lignocellulosic supplementation of the culture medium for mycelial development and production of phenoloxidase enzymes from Amazonian strains of gasteroid fungi (Basidiomycota)

Santana,

Couceiro,

Campos

2024

J. Biotechnol. Biodivers.

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Strains of gasteroid fungi are capable of oxidizing phenolic components and producing enzymes of great commercial value. However, the difficulty in producing biomass and, consequently, the low levels of expression of enzymes produced by these fungi hinder the advancement of biotechnological studies. A possible alternative may be supplementing the culture medium with lignocellulosic substrates, as observed in the cultivation of edible mushrooms, for example. Thus, the objective of this study was to analyze the effect of supplementing a potato-based culture medium with different concentrations of wheat and rice bran on mycelial development and the production of phenoloxidase enzymes of Amazonian strains of Cyathus and Geastrum. The basidiomas were collected in the Amazon of Pará, and the strains were obtained from mycelial isolation on Potato Dextrose Agar (PDA) medium. The strains were inoculated in semi-solid and liquid potato-based medium containing 10% and 20% rice bran and 10% and 20% wheat bran. For a period of 20 days, mycelial growth was observed in solid form, and for 40 days, the development of the strains in liquid medium was monitored, all incubated at 25°C in the dark. Growth and production of fresh and dry biomass were measured, as well as the production of phenoloxidase, arising from growth in liquid medium. Supplementation using 10% wheat bran was the most promising for the radial growth of four of the six species tested (C. limbatus, G. hirsutum, G. echinulatum, and G. schweinitzii), in addition to being the best treatment for the production of biomass and phenoloxidase enzymes for all species. Considering that wheat bran is easily accessible, this study stimulates basic science, especially in the Amazon, where Funga is still underestimated in terms of diversity and biotechnological potential.

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Lanostane triterpenoids, spiro-astraodoric acid, and astraodoric acids E and F, from the edible mushroom Astraeus odoratus

Cited by 14 publications

References 21 publications

Spiroinonotsuoxotriols A and B, Two Highly Rearranged Triterpenoids from Inonotus obliquus

Spiroinonotsuoxotriols A and B, Two Highly Rearranged Triterpenoids from Inonotus obliquus

Naturally Occurring Nor-Steroids and Their Design and Pharmaceutical Application

Lignocellulosic supplementation of the culture medium for mycelial development and production of phenoloxidase enzymes from Amazonian strains of gasteroid fungi (Basidiomycota)

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