Aspergillusene

Last updated
Aspergillusene A.svg
Aspergillusene A
Aspergillusene B.svg
Aspergillusene B
Aspergillusene C.svg
Aspergillusene C

Aspergillusenes are a group of chemical compounds first isolated from a strain of sea fan-derived fungus Aspergillus sydowii . [1] They are sesquiterpenes of the bisabolane-type. [2]

A laboratory synthesis of aspergillusene B was reported in 2020. [3]

Related Research Articles

<i>Aspergillus niger</i> Species of fungus

Aspergillus niger is a mold classified within the Nigri section of the Aspergillus genus. The Aspergillus genus consists of common molds found throughout the environment within soil and water, on vegetation, in fecal matter, on decomposing matter, and suspended in the air. Species within this genus often grow quickly and can sporulate within a few days of germination. A combination of characteristics unique to A. niger makes the microbe invaluable to the production of many acids, proteins and bioactive compounds. Characteristics including extensive metabolic diversity, high production yield, secretion capability, and the ability to conduct post-translational modifications are responsible for A. niger's robust production of secondary metabolites. A. niger's capability to withstand extremely acidic conditions makes it especially important to the industrial production of citric acid.

<span class="mw-page-title-main">Homoserine</span> Chemical compound

Homoserine (also called isothreonine) is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH2OH. l-Homoserine is not one of the common amino acids encoded by DNA. It differs from the proteinogenic amino acid serine by insertion of an additional -CH2- unit into the backbone. Homoserine, or its lactone form, is the product of a cyanogen bromide cleavage of a peptide by degradation of methionine.

<i>Tripterygium wilfordii</i> Species of flowering plant

Tripterygium wilfordii, or léi gōng téng (Mandarin), sometimes called thunder god vine but more properly translated thunder duke vine, is a vine used in traditional Chinese medicine.

<span class="mw-page-title-main">Caryophyllene</span> Chemical compound

Caryophyllene, more formally (−)-β-caryophyllene,(BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene and α-humulene, a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

<span class="mw-page-title-main">Artificial enzyme</span>

An artificial enzyme is a synthetic organic molecule or ion that recreates one or more functions of an enzyme. It seeks to deliver catalysis at rates and selectivity observed in naturally occurring enzymes.

<span class="mw-page-title-main">Marine fungi</span> Species of fungi that live in marine or estuarine environments

Marine fungi are species of fungi that live in marine or estuarine environments. They are not a taxonomic group, but share a common habitat. Obligate marine fungi grow exclusively in the marine habitat while wholly or sporadically submerged in sea water. Facultative marine fungi normally occupy terrestrial or freshwater habitats, but are capable of living or even sporulating in a marine habitat. About 444 species of marine fungi have been described, including seven genera and ten species of basidiomycetes, and 177 genera and 360 species of ascomycetes. The remainder of the marine fungi are chytrids and mitosporic or asexual fungi. Many species of marine fungi are known only from spores and it is likely a large number of species have yet to be discovered. In fact, it is thought that less than 1% of all marine fungal species have been described, due to difficulty in targeting marine fungal DNA and difficulties that arise in attempting to grow cultures of marine fungi. It is impracticable to culture many of these fungi, but their nature can be investigated by examining seawater samples and undertaking rDNA analysis of the fungal material found.

Aspergillus sydowii is a pathogenic fungus that causes several diseases in humans. It has been implicated in the death of sea fan corals in the Caribbean Sea.

<i>N</i>-Sulfinyl imine

N-Sulfinyl imines are a class of imines bearing a sulfinyl group attached to nitrogen. These imines display useful stereoselectivity reactivity and due to the presence of the chiral electron withdrawing N-sulfinyl group. They allow 1,2-addition of organometallic reagents to imines. The N-sulfinyl group exerts powerful and predictable stereodirecting effects resulting in high levels of asymmetric induction. Racemization of the newly created carbon-nitrogen stereo center is prevented because anions are stabilized at nitrogen. The sulfinyl chiral auxiliary is readily removed by simple acid hydrolysis. The addition of organometallic reagents to N-sulfinyl imines is the most reliable and versatile method for the asymmetric synthesis of amine derivatives. These building blocks have been employed in the asymmetric synthesis of numerous biologically active compounds.

<span class="mw-page-title-main">Fellutamide</span>

Fellutamides are tripeptide derivatives from Penicillium fellutanum and other fungi. They are potent proteasome inhibitor that stimulates nerve growth factor synthesis in vitro.

<span class="mw-page-title-main">Versicolamide B</span>

(-)-Versicolamide B and (+)-Versicolamide B are spiroindole alkaloids isolated from the fungus Aspergillus that belong to a class of naturally occurring 2,5-diketopiperazines. The versicolamides are structurally complex spiro-cyclized versions of prenylated cyclo(L-Trp-L-Pro) derivatives which possess a unique spiro-fusion to a pyrrolidine at the 3-position of the oxindole core together with the bicyclo[2.2.2]diazaoctane ring system. While (-)-versicolamide B was isolated from the marine fungus Aspergillus sp. the enantiomer (+)-versicolamide B was isolated from the terrestrial fungi Aspergillus versicolor NRRL. The total asymmetric syntheses of both enantiomers have been achieved and the implications of their biosynthesis have been investigated.

Aspergillusol A is an alpha-glucosidase inhibitor isolated from marine Aspergillus. Structurally, it consists of an erythritol group in the center, with two hydroxyimino-phenylpropanoyl groups attached to it from either side. It was synthesized in 2010 by researchers from King Fahd University of Petroleum and Minerals, starting with 4-hydroxybenzaldehyde.

Penicillium decaturense is a species of the genus of Penicillium which was isolated from a fungus in North America. Penicillium decaturense produces citrinin, 15-Deoxyoxalicine B, decaturins A and decaturins A

<span class="mw-page-title-main">Carbon quantum dots</span>

Carbon quantum dots also commonly called Carbon dots are carbon nanoparticles which are less than 10 nm in size and have some form of surface passivation.

A polyhydride or superhydride is a compound that contains an abnormally large amount of hydrogen. This can be described as high hydrogen stoichiometry. Examples include iron pentahydride FeH5, LiH6, and LiH7. By contrast, the more well known lithium hydride only has one hydrogen atom.

Borate sulfides are chemical mixed anion compounds that contain any kind of borate and sulfide ions. They are distinct from thioborates in which sulfur atoms replace oxygen in borates. There are also analogous borate selenides, with selenium ions instead of sulfur.

Selenogallates are chemical compounds which contain anionic units of selenium connected to gallium. They can be considered as gallates where selenium substitutes for oxygen. Similar compounds include the thiogallates and selenostannates. They are in the category of chalcogenotrielates or more broadly chalcogenometallates.

Sulfidostannates, or thiostannates are chemical compounds containing anions composed of tin linked with sulfur. They can be considered as stannates with sulfur substituting for oxygen. Related compounds include the thiosilicates, and thiogermannates, and by varying the chalcogen: selenostannates, and tellurostannates. Oxothiostannates have oxygen in addition to sulfur. Thiostannates can be classed as chalcogenidometalates, thiometallates, chalcogenidotetrelates, thiotetrelates, and chalcogenidostannates. Tin is almost always in the +4 oxidation state in thiostannates, although a couple of mixed sulfides in the +2 state are known,

A tellurite fluoride is a mixed anion compound containing tellurite and fluoride ions. They have also been called oxyfluorotellurate(IV) where IV is the oxidation state of tellurium in tellurite.

The oxalate phosphites are chemical compounds containing oxalate and phosphite anions. They are also called oxalatophosphites or phosphite oxalates. Oxalate phosphates can form metal organic framework compounds.

Sulfidogermanates or thiogermanates are chemical compounds containing anions with sulfur atoms bound to germanium. They are in the class of chalcogenidotetrelates. Related compounds include thiosilicates, thiostannates, selenidogermanates, telluridogermanates and selenidostannates.

References

  1. Trisuwan, K; Rukachaisirikul, V; Kaewpet, M; Phongpaichit, S; Hutadilok-Towatana, N; Preedanon, S; Sakayaroj, J (2013-08-12). "Sesquiterpene and xanthone derivatives from the sea fan-derived fungus Aspergillus sydowii PSU-F154". J Nat Prod. 74 (7): 1663–7. doi:10.1021/np200374j. PMID   21718031.
  2. Liu, Nianzhen; Peng, Shuai; Yang, Jie; Cong, Ziwen; Lin, Xiuping; Liao, Shengrong; Yang, Bin; Zhou, Xuefeng; Zhou, Xiaojiang; Liu, Yonghong; Wang, Junfeng (2019). "Structurally diverse sesquiterpenoids and polyketides from a sponge-associated fungus Aspergillus sydowii SCSIO41301". Fitoterapia. 135: 27–32. doi:10.1016/j.fitote.2019.03.031. PMID   30946944. S2CID   96432484.
  3. Grabovyi, Gennadii A.; Bhatti, Aisha; Mohr, Justin T. (2020). "Total Synthesis of Benzofuran-Based Aspergillusene B via Halogenative Aromatization of Enones". Organic Letters. 22 (11): 4196–4200. doi:10.1021/acs.orglett.0c01259. PMID   32437168. S2CID   218831928.