Aurantiomide

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Aurantiomide
Aurantiomide A.png
Aurantiomide B.png
Aurantiomide C.png
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • A:InChI=1S/C19H24N4O4/c1-11(2)10-19(27-3)18-21-13-7-5-4-6-12(13)17(26)23(18)14(16(25)22-19)8-9-15(20)24/h4-7,11,14H,8-10H2,1-3H3,(H2,20,24)(H,22,25)/t14-,19+/m0/s1
    Key: YQGOVBHFRUCFDP-IFXJQAMLSA-N
  • B:InChI=1S/C18H22N4O4/c1-10(2)9-18(26)17-20-12-6-4-3-5-11(12)16(25)22(17)13(15(24)21-18)7-8-14(19)23/h3-6,10,13,26H,7-9H2,1-2H3,(H2,19,23)(H,21,24)/t13-,18+/m0/s1
    Key: VZHFOIYILDANRZ-SCLBCKFNSA-N
  • C:InChI=1S/C18H20N4O3/c1-10(2)9-13-16-20-12-6-4-3-5-11(12)18(25)22(16)14(17(24)21-13)7-8-15(19)23/h3-6,9-10,14H,7-8H2,1-2H3,(H2,19,23)(H,21,24)/b13-9-/t14-/m0/s1
    Key: UKYRPVOCKVERNT-XXYUJHKVSA-N
  • A:CC(C)C[C@]1(c2nc3ccccc3c(=O)n2[C@H](C(=O)N1)CCC(=O)N)OC
  • B:CC(C)C[C@]1(c2nc3ccccc3c(=O)n2[C@H](C(=O)N1)CCC(=O)N)O
  • C:CC(C)/C=C\1/C2=NC3=CC=CC=C3C(=O)N2[C@H](C(=O)N1)CCC(=O)N
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Aurantiomides are quinazoline alkaloids isolated from the fungus Penicillium aurantiogriseum . [1] Aurantiomide is contained in the traditional Chinese medicine LeZhe. [2]

Related Research Articles

<i>Penicillium</i> Genus of fungi

Penicillium is a genus of ascomycetous fungi that is part of the mycobiome of many species and is of major importance in the natural environment, in food spoilage, and in food and drug production.

Penicillium aurantiogriseum is a plant pathogen infecting asparagus and strawberry. Chemical compounds isolated from Penicillium aurantiogriseum include anicequol and auranthine.

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

Communesin B is a cytotoxic fungi isolate from marine Penicillium strains. Its cytotoxicity makes it a potential anticancer compound.

Fellutanine A, B, C and D are bio-active diketopiperazine alkaloids isolated from the cultures of Penicillium fellutanum, that belongs to a class of naturally occurring 2,5-diketopiperazines. Originally they were thought to be based on the "trans" cyclic dipetide cyclo(L-Trp-D-Trp) but were later shown to be based on the "cis" cyclic dipetide cyclo(L-Trp-L-Trp). This was also confirmed when fellutanine A, B and C were isolated from Penicillium simplicissimum. The fellutanines A−C, are non-annulated analogues of cyclo(L-Trp-L-Trp), but unlike their diannulated analogue fellutanine D are not cytotoxic.

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

Quinocitrinines are quinoline alkaloids isolated from a permafrost Penicillium.

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

Piscarinines are bioactive alkaloid isolates of Penicillium piscarium NKM F-961 and Penicillium piscarium Westling that belong to a class of naturally occurring 2,5-diketopiperazines. The cytotoxic dehydroproline tryptophan derivatives piscarinines A and B were shown to be active against the prostate cancer cell line LNCAP.

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

Meleagrin and its derivatives such as oxaline are bio-active benzylisoquinoline alkaloids made by various species of Penicillium fungi. It is similar to other fungal alkaloids, such as Roquefortine C, which is made as an intermediate in the same biosynthetic pathway.

<span class="mw-page-title-main">14-Norpseurotin A</span> Chemical compound

14-Norpseurotin A is an alkaloid and a bio-active metabolite of Aspergillus, featuring an oxa-spiro-lactam core.

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

Dideoxyverticillin A, also known as (+)-11,11′-dideoxyverticillin A, is a complex epipolythiodioxopiperazine initially isolated from the marine fungus Penicillium sp. in 1999. It has also been found in the marine fungus Bionectriaceae, and belongs to a class of naturally occurring 2,5-diketopiperazines.

Fungal isolates have been researched for decades. Because fungi often exist in thin mycelial monolayers, with no protective shell, immune system, and limited mobility, they have developed the ability to synthesize a variety of unusual compounds for survival. Researchers have discovered fungal isolates with anticancer, antimicrobial, immunomodulatory, and other bio-active properties. The first statins, β-Lactam antibiotics, as well as a few important antifungals, were discovered in fungi.

Penicillium chermesinum is an anamorph fungus species of the genus of Penicillium which was isolated from soil from Nova Scotia in Canada.Penicillium chermesinum produces plastatin, luteosporin, xanthomegnin, azaphilones, p-terphenyls and costaclavine.

Penicillium citrinum is an anamorph, mesophilic fungus species of the genus of Penicillium which produces tanzawaic acid A-D, ACC, Mevastatin, Quinocitrinine A, Quinocitrinine B, and nephrotoxic citrinin. Penicillium citrinum is often found on moldy citrus fruits and occasionally it occurs in tropical spices and cereals. This Penicillium species also causes mortality for the mosquito Culex quinquefasciatus. Because of its mesophilic character, Penicillium citrinum occurs worldwide. The first statin (Mevastatin) was 1970 isolated from this species.

Penicillium corylophilum is a species of the genus of Penicillium which occurs in damp buildings in United States, Canada and western Europe but it can also be found in a variety of foods and mosquitoes. Penicillium corylophilum produces the alkaloid epoxyagroclavine and citrinin and is a pathogen to mosquitoes.

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

Penicillium herquei is an anamorph, filamentous species of the genus of Penicillium which produces citreorosein, emodin, hualyzin, herquline B, janthinone, citrinin and duclauxin,.

Penicillium palitans is an anamorph species of fungus in the genus Penicillium which was isolated from cheese and ancient permafrost deposits. Penicillium palitans produces viridicatin, cyclopiazonic acid, roquefortine, palitantin and ochratoxin A

Penicillium paneum is a species of fungus in the genus Penicillium which can spoil cereal grains. Penicillium paneum produces 1-Octen-3-ol and penipanoid A, penipanoid B, penipanoid C, patulin and roquefortine C

Penicillium thymicola is a halotolerant species of fungus in the genus Penicillium which produces okaramine A, daldinin D, alantrypinone, seranttrypinone, fumiquinazoline F and fumiquinazoline G.

Penicillium vinaceum is an anamorph species of fungus in the genus Penicillium which produces penicillivinacine, vinaxanthone and citrmycetin.

<span class="mw-page-title-main">Phomoxanthone</span> Class of chemical compounds

The phomoxanthones are a loosely defined class of natural products. The two founding members of this class are phomoxanthone A and phomoxanthone B. Other compounds were later also classified as phomoxanthones, although a unifying nomenclature has not yet been established. The structure of all phomoxanthones is derived from a dimer of two covalently linked tetrahydroxanthones, and they differ mainly in the position of this link as well as in the acetylation status of their hydroxy groups. The phomoxanthones are structurally closely related to other tetrahydroxanthone dimers such as the secalonic acids and the eumitrins. While most phomoxanthones were discovered in fungi of the genus Phomopsis, most notably in the species Phomopsis longicolla, some have also been found in Penicillium sp.

References

  1. Xin, Zhi Hong; Fang, Yuchun; Du, Lin; Zhu, Tianjiao; Duan, Lin; Chen, Juan; Gu, Qian-Qun; Zhu, Wei-Ming (2007). "Aurantiomides A−C, Quinazoline Alkaloids from the Sponge-Derived Fungus Penicillium aurantiogriseum SP0-19". Journal of Natural Products. 70 (5): 853–855. doi:10.1021/np060516h. ISSN   0163-3864. PMID   17455978.
  2. Melrose, James; Smith, Margaret M. (9 October 2022). "Natural and Semi-Synthetic Flavonoid Anti-SARS-CoV-2 Agents for the Treatment of Long COVID-19 Disease and Neurodegenerative Disorders of Cognitive Decline". Frontiers in Bioscience-Elite. 14 (4): 27. doi: 10.31083/j.fbe1404027 .