Hachimycin

Last updated
Hachimycin
Hachimycin.svg
Clinical data
ATC code
Identifiers
  • (4E,6E,8E,10E,12E,14E,16E)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19-[7-(4-aminophenyl)-5-hydroxy-7-oxoheptan-2-yl]-25,27,31,33,35,37-hexahydroxy-18-methyl-21,23-dioxo-20,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic acid;(4E,6E,8E,10E,12E,14E,16E)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19-[7-(4-aminophenyl)-5-hydroxy-7-oxoheptan-2-yl]-27,29,31,33,35,37-hexahydroxy-18-methyl-21,23-dioxo-20,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C116H168N4O36
Molar mass 2194.612 g·mol−1
3D model (JSmol)
  • CC1C=CC=CC=CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC(CC(CC(CCCC(=O)CC(=O)OC1C(C)CCC(CC(=O)C3=CC=C(C=C3)N)O)O)O)O)O)O)O)C(=O)O)OC4C(C(C(C(O4)C)O)N)O.CC1C=CC=CC=CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC(CCCC(CC(CC(=O)CC(=O)OC1C(C)CCC(CC(=O)C3=CC=C(C=C3)N)O)O)O)O)O)O)O)C(=O)O)OC4C(C(C(C(O4)C)O)N)O
  • InChI=1S/2C58H84N2O18/c1-35-17-14-12-10-8-6-4-5-7-9-11-13-15-20-46(76-57-54(71)52(60)53(70)37(3)75-57)32-49-51(56(72)73)48(68)34-58(74,78-49)33-45(66)29-44(65)28-43(64)27-40(61)18-16-19-41(62)31-50(69)77-55(35)36(2)21-26-42(63)30-47(67)38-22-24-39(59)25-23-38;1-35-17-14-12-10-8-6-4-5-7-9-11-13-15-20-46(76-57-54(71)52(60)53(70)37(3)75-57)32-49-51(56(72)73)48(68)34-58(74,78-49)33-45(66)28-41(62)19-16-18-40(61)27-43(64)29-44(65)31-50(69)77-55(35)36(2)21-26-42(63)30-47(67)38-22-24-39(59)25-23-38/h4-15,17,20,22-25,35-37,40,42-46,48-49,51-55,57,61,63-66,68,70-71,74H,16,18-19,21,26-34,59-60H2,1-3H3,(H,72,73);4-15,17,20,22-25,35-37,40-43,45-46,48-49,51-55,57,61-64,66,68,70-71,74H,16,18-19,21,26-34,59-60H2,1-3H3,(H,72,73)/b5-4-,8-6-,9-7-,12-10-,13-11-,17-14-,20-15-;5-4+,8-6+,9-7+,12-10+,13-11+,17-14-,20-15+/t35?,36?,37-,40?,42?,43?,44?,45?,46?,48?,49?,51?,52+,53-,54+,55?,57+,58?;35?,36?,37-,40?,41?,42?,43?,45?,46?,48?,49?,51?,52+,53-,54+,55?,57+,58?/m11/s1 Yes check.svgY
  • Key:RZWQQZWPVPHLSY-UGMBPVHXSA-N Yes check.svgY
   (verify)

Hachimycin, also known as trichomycin, [1] is a polyene macrolide antibiotic, [2] antiprotozoal, [3] and antifungal derived from streptomyces. [4] It was first described in 1950, and in most research cases have been used for gynecological infections. [3]

Related Research Articles

<span class="mw-page-title-main">Macrolide</span> Class of natural products

The Macrolides are a class of natural products that consist of a large macrocyclic lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, may be attached. The lactone rings are usually 14-, 15-, or 16-membered. Macrolides belong to the polyketide class of natural products. Some macrolides have antibiotic or antifungal activity and are used as pharmaceutical drugs. Rapamycin is also a macrolide and was originally developed as an antifungal, but is now used as an immunosuppressant drug and is being investigated as a potential longevity therapeutic.

<span class="mw-page-title-main">Nystatin</span> Pharmaceutical drug

Nystatin, sold under the brandname Mycostatin among others, is an antifungal medication. It is used to treat Candida infections of the skin including diaper rash, thrush, esophageal candidiasis, and vaginal yeast infections. It may also be used to prevent candidiasis in those who are at high risk. Nystatin may be used by mouth, in the vagina, or applied to the skin.

<i>Streptomyces</i> Genus of bacteria

Streptomyces is the largest genus of Actinomycetota and the type genus of the family Streptomycetaceae. Over 500 species of Streptomyces bacteria have been described. As with the other Actinomycetota, streptomycetes are gram-positive, and have genomes with high GC content. Found predominantly in soil and decaying vegetation, most streptomycetes produce spores, and are noted for their distinct "earthy" odor that results from production of a volatile metabolite, geosmin.

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

Natamycin, also known as pimaricin, is an antifungal medication used to treat fungal infections around the eye. This includes infections of the eyelids, conjunctiva, and cornea. It is used as eyedrops. Natamycin is also used in the food industry as a preservative.

Polyene antimycotics, sometimes referred to as polyene antibiotics, are a class of antimicrobial polyene compounds that target fungi. These polyene antimycotics are typically obtained from some species of Streptomyces bacteria. Previously, polyenes were thought to bind to ergosterol in the fungal cell membrane and thus weakening it and causing leakage of K+ and Na+ ions, which could contribute to fungal cell death. However, more detailed studies of polyene molecular properties have challenged this model suggesting that polyenes instead bind and extract ergosterol directly from the cellular membrane thus disrupting the many cellular functions ergosterols perform. Amphotericin B, nystatin, and natamycin are examples of polyene antimycotics. They are a subgroup of macrolides.

<span class="mw-page-title-main">Lincosamides</span> Group of antibiotics

Lincosamides are a class of antibiotics, which include lincomycin, clindamycin, and pirlimycin.

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

Desosamine is a 3-(dimethylamino)-3,4,6-trideoxyhexose found in certain macrolide antibiotics such as the commonly prescribed erythromycin, azithromycin, clarithroymcin, methymycin, narbomycin, oleandomycin, picromycin and roxithromycin. As the name suggests, these macrolide antibiotics contain a macrolide or lactone ring and they are attached to the ring Desosamine which is crucial for bactericidal activity. The biological action of the desosamine-based macrolide antibiotics is to inhibit the bacterial ribosomal protein synthesis. These antibiotics which contain Desosamine are widely used to cure bacterial-causing infections in human respiratory system, skin, muscle tissues, and urethra.

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

Perimycin, also known as aminomycin and fungimycin, is polyene antibiotic produced by Streptomyces coelicolor var. aminophilus. The compound exhibits antifungal properties.

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

Pikromycin was studied by Brokmann and Hekel in 1951 and was the first antibiotic macrolide to be isolated. Pikromycin is synthesized through a type I polyketide synthase system in Streptomyces venezuelae, a species of Gram-positive bacterium in the genus Streptomyces. Pikromycin is derived from narbonolide, a 14-membered ring macrolide. Along with the narbonolide backbone, pikromycin includes a desosamine sugar and a hydroxyl group. Although Pikromycin is not a clinically useful antibiotic, it can be used as a raw material to synthesize antibiotic ketolide compounds such as ertythromycins and new epothilones.

Venturicidins are a group of antifungal compounds. The first member of this class was isolated from Streptomyces bacteria in 1961. Additional members of this class were subsequently isolated and characterized. An antifungal substance "aabomycin A" was isolated from Streptomyces in 1969. However, in 1990 it was reported that aabomycin A is actually a 3:1 mixture of two related components, which were then named aabomycin A1 and aabomycin A2. The structures of these were shown to be identical with those of the previously characterized compounds venturicidin A and venturicidin B, respectively. A new analog, venturicidin C, was recently reported from a Streptomyces isolated from thermal vents associated with the Ruth Mullins coal fire in Kentucky.

Naphthomycins are a group of closely related antimicrobial chemical compounds isolated from Streptomyces. They are considered a subclass of ansamycins.

Streptomyces isolates have yielded the majority of human, animal, and agricultural antibiotics, as well as a number of fundamental chemotherapy medicines. Streptomyces is the largest antibiotic-producing genus of Actinomycetota, producing chemotherapy, antibacterial, antifungal, antiparasitic drugs, and immunosuppressants. Streptomyces isolates are typically initiated with the aerial hyphal formation from the mycelium.

Streptomyces albidoflavus is a bacterium species from the genus of Streptomyces which has been isolated from soil from Poland. Streptomyces albidoflavus produces dibutyl phthalate and streptothricins.

Streptomyces cellulosae is a bacterium species from the genus of Streptomyces which has been isolated from garden soil. Streptomyces cellulosae produces fungichromin.

Streptomyces cirratus is a bacterium species from the genus of Streptomyces. Streptomyces cirratus produces phegomycin, phegomycin D, phegomycin DGPT, cirratiomycin A, cirramycin A and cirramycin B.'

Streptomyces coeruleorubidus is a bacterium species from the genus of Streptomyces which has been isolated from marine sediment. Streptomyces coeruleorubidus produces the following medications: pacidamycin 1, baumycin B1, baumycin B2, baumycin C1, feudomycin A, feudomycin B, feudomycin C, ficellomycin, feudomycinone A, and rubomycin.

Streptomyces coerulescens is a bacterium species from the genus of Streptomyces which has been isolated from soil. Streptomyces coerulescens produces gilvocarcin M, gilvocarcin V, coerulomycin and anantin.

Streptomyces durmitorensis is a bacterium species from the genus of Streptomyces which has been isolated from soil from the Durmitor National Park in Serbia and Montenegro.

Streptomyces lavenduligriseus is a bacterium species from the genus of Streptomyces. Streptomyces lavenduligriseus produces Pentenomycin II, Pentenomycin III and narangomyci.

Streptomyces lasiicapitis is a bacterium species from the genus of Streptomyces which has been isolated from the head of the ant Lasius fuliginosus. Streptomyces lasiicapitis produces the antibiotic kanchanamycin.

References

  1. "Trichomycin - C116H168N4O36 - PubChem" . Retrieved July 7, 2016.
  2. Mechlinski W, Schaffner CP (June 1980). "Characterization of aromatic heptaene macrolide antibiotics by high performance liquid chromatography". The Journal of Antibiotics. 33 (6): 591–9. doi: 10.7164/antibiotics.33.591 . PMID   6893446.
  3. 1 2 Nakano, Hiroshi; Hattori, Kiyoshi; Seki, Masahiro; Hirata, Yoshimasa (1956). "Studies on Trichomycin. III". The Journal of Antibiotics, Series A. 9 (5): 172–175. doi:10.11554/antibioticsa.9.5_172.
  4. Komori T (July 1990). "Trichomycin B, a polyene macrolide from Streptomyces". The Journal of Antibiotics. 43 (7): 778–82. doi: 10.7164/antibiotics.43.778 . PMID   2387771.