381:
370:
400:
24:
136:
InChI=1S/C39H52N2O8/c1-31(48-39-37(45)36(44)35(43)32(2)49-39)27-24-22-20-18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-21-23-25-29-34(42)41-33(38(46)47)28-26-30-40/h3-25,29,31-33,35-37,39,43-45H,26-28,30,40H2,1-2H3,(H,41,42)(H,46,47)/b4-3+,7-5+,8-6+,11-9+,12-10+,15-13+,16-14+,19-17+,20-18+,23-21+,24-22+,29-25+/t31?,32-,33-,35-,36+,37+,39+/m0/s1
68:
392:
694:
Paradas M, Jurado R, Haidour A, RodrĂguez
Granger J, Sampedro MartĂnez A, de la Rosa Fraile M, Robles R, Justicia J, Cuerva JM (2012). "Clarifying the structure of granadaene: Total synthesis of related analogue - granadaene and confirmation of its absolute stereochemistry".
496:, Among the cyl operon, the cylE gene is required for pigment production, and transcription of cyl genes is regulated by the CovR/S two-component system, and a pathway for the pigment biosynthesis requiring all the genes of the
1828:
Huebner EM, GudjĂłnsdĂłttir MJ, Dacanay MB, Nguyen S, Brokaw A, Sharma K, Elfvin A, Hentz E, Rivera YR, Burd N, Shivakumar M, Coler B, Li M, Li A, Munson J, Orvis A, Coleman M, Jacobsson B, Rajagopal L, Adams
Waldorf KM. (2022).
1456:
Armistead B, Herrero-Foncubierta P, Coleman M, Quach P, Whidbey C, Justicia J, Tapia R, Casares R, Millán A, Haidour A, Rodriguez
Granger J, Vornhagen J, Santana-Ufret V, Merillat S, Waldorf KA, Cuerva JM, Rajagopal L (2020).
1756:
Armistead B, Herrero-Foncubierta P, Coleman M, Quach P, Whidbey C, Justicia J, Tapia R, Casares R, Millán A, Haidour A, Granger JR, Vornhagen J, Santana-Ufret V, Merillat S, Adams
Waldorf K, Cuerva JM, Rajagopal L. (2020).
614:
Nevertheless, 1–5% of GBS strains are non-hemolytic and do not produce pigment. These non-hemolytic and non-pigmented GBS strains (lacking pigment and hemolysin) are considered less virulent because of that.
1644:
Whidbey C, Vornhagen J, Gendrin C, Boldenow E, Samson JM, Doering K, Ngo L, Ezekwe EA Jr, Gundlach JH, Elovitz MA, Liggitt D, Duncan JA, Adams
Waldorf KM, Rajagopal L (2015).
2053:
1945:
1880:
1814:
1742:
1521:
1442:
1379:
1314:
1249:
931:
872:
426:
Non-terpenoid polyenes up to 10 conjugated double bonds are also a bizarre class of biologically natural products (laetiporic acids) found in the basidiomycete
152:
572:(a non-hemolytic non-pigmented Gram-positive bacterium) and the expression of the GBS cyl operon conferred hemolysis, pigmentation, and cytotoxicity to
1831:"Virulence, phenotype and genotype characteristics of invasive group B Streptococcus isolates obtained from Swedish pregnant women and neonates"
1145:"Propionibacterium jensenii produces the polyene pigment granadaene and has hemolytic properties similar to those of Streptococcus agalactiae"
1200:
Masanori Saito, Noriko
Shinozaki-Kuwahara, Osamu Tsudukibashi, Tomomi Hashizume-Takizawa, Ryoki Kobayashi, Tomoko Kurita-Ochiai (2018).
521:, where it could play a role in membrane stabilization, similar to the role of carotenes in other bacterial membranes. In addition to
549:, where it can cause defects such as red spots in some cheeses. Probably granadaene is also present in other related species such as
127:
1328:
Armistead B, Whidbey C, Iyer LM, Herrero-Foncubierta P, Quach P, Haidour A, Aravind L, Cuerva JM, Jaspan HB, Rajagopal L. (2020).
1894:
Jahn, K.; Shumba, P.; Quach, P.; MĂĽsken, M.; Wesche, J.; Greinacher, A.; Rajagopal, L.; Hammerschmidt, S.; Siemens, N. (2022).
291:
at the other. Granadaene contains 12 conjugated double bonds, a feature which is unprecedented among non-isoprenoid pigments.
359:
1330:"The cyl Genes Reveal the Biosynthetic and Evolutionary Origins of the Group B Streptococcus Hemolytic Lipid, Granadaene"
230:
2083:
1759:"Lipid analogs reveal features critical for hemolysis and diminish granadaene mediated Group B Streptococcus infection"
1459:"Lipid analogs reveal features critical for hemolysis and diminish granadaene mediated Group B Streptococcus infection"
1263:
Neuzil-Bunesova V, Ramirez Garcia A, Modrackova N, Makovska M, Sabolova M, Spröer C, Bunk B, Blom J, Schwab C (2022).
783:
449:
specific to β-hemolytic GBS, and because of that, detection of red colonies from clinical samples, when cultivated on
1003:"Identification of genetic determinants for the hemolytic activity of Streptococcus agalactiae by ISS1 transposition"
1538:
Whidbey C, Harrell MI, Burnside K, Ngo L, Becraft AK, Iyer LM, Aravind L, Hitti J, Waldorf KM, Rajagopal L (2013).
380:
369:
909:
263:
1961:"Non-haemolytic and non-pigmented group b streptococcus, an infrequent cause of early onset neonatal sepsis"
1202:"Pseudopropionibacterium rubrum sp. nov., a novel red-pigmented species isolated from human gingival sulcus"
1539:
2047:
1939:
1874:
1808:
1736:
1515:
1436:
1373:
1308:
1243:
866:
391:
36:
1646:"A streptococcal lipid toxin induces membrane permeabilization and pyroptosis leading to fetal injury"
503:
Like the biosynthesis of the pigment, the hemolytic activity also requires in GBS the 12 genes of the
2073:
1770:
1470:
1156:
650:
339:
823:
M Rosa-Fraile, J Rodriguez-Granger, M Cueto-Lopez, A Sampedro, E B Gaye, J M Haro, A Andreu (1999).
408:
355:
1424:
1231:
323:
2078:
2035:
1990:
1927:
1862:
1796:
1724:
1675:
1623:
1572:
1496:
1416:
1361:
1296:
1223:
1182:
1122:
1073:
1032:
983:
925:
854:
764:
712:
676:
470:
276:
88:
1540:"A hemolytic pigment of Group B Streptococcus allows bacterial penetration of human placenta"
735:"Characterization and Incidence of Pigment Production by Human Clinical Group B Streptococci"
2025:
2017:
1980:
1972:
1917:
1907:
1852:
1842:
1786:
1778:
1714:
1706:
1665:
1657:
1613:
1603:
1562:
1554:
1486:
1478:
1406:
1351:
1341:
1286:
1276:
1213:
1172:
1164:
1112:
1104:
1063:
1022:
1014:
973:
965:
844:
836:
798:
754:
746:
704:
666:
658:
608:
462:
446:
175:
2008:
Armistead B, Quach P, Snyder JM, Santana-Ufret V, Furuta A, Brokaw A, Rajagopal L. (2020).
588:
The hemolytic activity of granadene is strongly linked to the length of its polyene chain.
888:"Prevention of perinatal group B streptococcal disease: revised guidelines from CDC, 2010"
331:
1896:"Group B Streptococcal Hemolytic Pigment Impairs Platelet Function in a Two-Step Process"
1774:
1474:
1160:
654:
160:
C1(O)(O)(O)(O1)OC(C)C/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C(=O)N(CCCN)C(=O)O
44:)-5-Amino-2-oxyoctacosa-2,4,6,8,10,12,14,16,18,20,22,24-dodecaenoyl]amino]pentanoic acid
2030:
2009:
1985:
1960:
1922:
1895:
1857:
1830:
1791:
1758:
1719:
1694:
1670:
1645:
1618:
1591:
1567:
1491:
1356:
1329:
1291:
1264:
1177:
1144:
1068:
1051:
978:
953:
671:
638:
450:
416:
347:
224:
1695:"The Double Life of Group B Streptococcus: Asymptomatic Colonizer and Potent Pathogen"
1117:
1092:
825:"Use of Granada medium to detect group B streptococcal colonization in pregnant women"
759:
734:
113:
2067:
1052:"The cyl genes of Streptococcus agalactiae are involved in the production of pigment"
1027:
1018:
1002:
849:
824:
637:
Rosa-Fraile M, RodrĂguez-Granger J, Haidour-Benamin A, Cuerva JM, Sampedro A (2006).
518:
311:
1428:
1235:
840:
1608:
1108:
607:
cells, including platelets. Because of this, granadaene is considered an important
486:
474:
327:
280:
246:
784:"The Laetiporus polyketide synthase LpaA produces a series of antifungal polyenes"
399:
1411:
1394:
1001:
Spellerberg B, Pohl B, Haase G, Martin S, Weber-Heynemann J, LĂĽtticken R (1999).
750:
910:"Guidelines for the Detection and Identification of Group B Streptococcus. 2021"
478:
1847:
1782:
1482:
1395:"The pore-forming action of polyenes: From model membranes to living organisms"
802:
1710:
1281:
708:
639:"Granadaene: Proposed Structure of the Group B Streptococcus Polyenic Pigment"
604:
428:
335:
254:
209:
79:
2021:
1458:
1346:
887:
1976:
1661:
1218:
1201:
969:
600:
592:
508:
295:
284:
2039:
1994:
1931:
1866:
1800:
1728:
1679:
1627:
1576:
1500:
1420:
1365:
1300:
1227:
1186:
1077:
1036:
987:
858:
716:
680:
1912:
1126:
908:
Filkins L , Hauser J, Robinson-Dunn B, Tibbetts R, Boyanton B , Revell P.
1558:
1168:
768:
662:
420:
412:
363:
303:
288:
2010:"Hemolytic membrane vesicles of Group B Streptococcus promote infection"
580:
operon is sufficient for
Granadaene production in a heterologous host.
482:
315:
307:
258:
250:
100:
23:
493:
319:
507:
operon. Moreover,it has been proposed that granadaene is indeed the
223:
Except where otherwise noted, data are given for materials in their
1592:"Group B Streptococcus: Virulence Factors and Pathogenic Mechanism"
485:
necessary for the biosynthesis of granadaene in GBS are coded by a
1959:
Rodriguez-Granger J, Spellerberg B, Asam D, Rosa-Fraile M (2015).
398:
390:
379:
368:
299:
67:
57:
1393:
Kristanc L, Božič B, Jokhadar ŠZ, Dolenc MS, Gomišček G. (2019).
411:
of the granadaene (in DMSO/TFA) is almost identical to that of a
1265:"Feed Insects as a Reservoir of Granadaene-Producing Lactococci"
351:
954:"Group B streptococcal haemolysin and pigment, a tale of twins"
1693:
Armistead B, Oler E, Adams
Waldorf K, Rajagopal L. (2019).
1143:
Vanberg C, Lutnaes BF, Langsrud T, Nees IF, Holo H (2007).
415:
with a similar conjugated system of 12 double bonds (e.g.
279:
made up of a linear chain of 12 conjugated carbon-carbon
782:
Seibold PS. Lenz C. Gressler M. Hoffmeister D. (2020).
1050:
Spellerberg B, Martin S, Brandt C, LĂĽtticken R (2000).
419:), which is why the GBS pigment was considered to be a
395:
Ultraviolet/visible spectrum of granadaene, in DMSO+TFA
403:
Proposed metabolic pathway for granadaene biosynthesis
342:(TFA). Granadaene, can be extracted from cultures of
453:, allows the straightforward identification of GBS.
591:It has been proposed that granadaene is indeed the
338:, and in most solvents, it is soluble in DMSO–0.1%
576:. Proving that the expression of the genes of the
947:
945:
943:
941:
112:
1639:
1637:
1533:
1531:
1138:
1136:
952:Rosa-Fraile M, Dramsi S, Spellerberg B (2014).
445:Production of the red pigment granadaene is a
407:The fine-structure of the ultraviolet-visible
257:biosynthetic origin, that constitutes the red
728:
726:
8:
2052:: CS1 maint: multiple names: authors list (
1944:: CS1 maint: multiple names: authors list (
1879:: CS1 maint: multiple names: authors list (
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930:: CS1 maint: multiple names: authors list (
871:: CS1 maint: multiple names: authors list (
553:. Granadaene is also produced by strains of
632:
630:
628:
555:Lactocococcus garvieae/petaury/formosensis
87:
15:
2029:
1984:
1921:
1911:
1856:
1846:
1790:
1718:
1669:
1617:
1607:
1566:
1490:
1410:
1355:
1345:
1290:
1280:
1217:
1176:
1116:
1067:
1026:
977:
848:
758:
670:
517:The pigment is localized, in GBS, in the
599:, the GBS hemolysin is a broad-spectrum
624:
157:
132:
2045:
1937:
1872:
1806:
1734:
1513:
1434:
1371:
1306:
1241:
923:
886:Verani JR, McGee L, Schrag SJ (2010).
864:
529:genes has been reported in pigmented
387:on granada agar, anaerobic incubation
283:which is connected to the amino acid
139:Key: PPFISAQUKQQDHW-OBEWLBDZSA-N
7:
912:. American Society for Microbiology
525:the presence of granadaene and the
103:
2014:The Journal of Infectious Diseases
1069:10.1111/j.1574-6968.2000.tb09182.x
294:Granadaene is dark red, odorless,
14:
1019:10.1128/JB.181.10.3212-3219.1999
193:
187:
22:
841:10.1128/JCM.37.8.2674-2677.1999
227:(at 25 °C , 100 kPa).
1609:10.3390/microorganisms10122483
1109:10.1128/MMBR.48.3.181-198.1984
551:Pseudopropionibacterium rubrum
199:
181:
1:
1835:Ann Clin Microbiol Antimicrob
1399:Biochim Biophys Acta Biomembr
360:size-exclusion chromatography
1412:10.1016/j.bbamem.2018.11.006
751:10.1128/jcm.8.1.105-107.1978
733:Merrit K, Jacobs NJ (1978).
584:Granadaene and GBS Virulence
441:detection and identification
2100:
2016:. jiaa548 (8): 1488–1496.
1848:10.1186/s12941-022-00534-2
1783:10.1038/s41467-020-15282-0
1483:10.1038/s41467-020-15282-0
803:10.1038/s41429-020-00362-6
568:genes have been cloned in
500:operon has been proposed.
1711:10.1016/j.jmb.2019.01.035
1282:10.3389/fmicb.2022.848490
1093:"Bacterial tryterpenoids"
709:10.1016/j.bmc.2012.09.017
561:cluster is also present.
469:. It is the product of a
287:at one end and the sugar
267:(group B streptococcus).
221:
168:
148:
123:
49:
35:
30:
21:
1347:10.3389/fmicb.2019.03123
385:Streptococcus agalactiae
374:Streptococcus agalactiae
264:Streptococcus agalactiae
1662:10.15252/emmm.201404883
1219:10.1111/1348-0421.12592
970:10.1111/1574-6976.12071
366:LH using DMSO–0.1%TFA.
2022:10.1093/infdis/jiaa548
1590:Liu Y, Liu J. (2022).
1149:Appl Environ Microbiol
643:Appl Environ Microbiol
531:Acidipropionibacterium
404:
396:
388:
377:
358:(KOH) and purified by
275:Granadaene contains a
1977:10.1093/femspd/ftv089
1965:Pathogens and Disease
1913:10.3390/cells11101637
1463:Nature Communications
603:able to destroy many
402:
394:
383:
372:
1559:10.1084/jem.20122753
1169:10.1128/AEM.00545-07
1056:FEMS Microbiol. Lett
663:10.1128/aem.00756-06
457:Biological relevance
340:trifluoroacetic acid
2084:Biological pigments
1775:2020NatCo..11.1502A
1475:2020NatCo..11.1502A
1161:2007ApEnM..73.5501V
958:FEMS Microbiol. Rev
655:2006ApEnM..72.6367R
473:similar to that of
409:absorption spectrum
356:potassium hydroxide
217: g·mol
18:
1091:Taylor RF (1984).
897:. 59(RR-10): 1–32.
791:J Antibiot (Tokyo)
574:Lactococcus lactis
570:Lactococcus lactis
405:
397:
389:
378:
346:in granada broth (
324:dimethyl sulfoxide
261:characteristic of
231:Infobox references
16:
1705:(16): 2914–2931.
1206:Microbiol Immunol
1155:(17): 5501–5506.
1013:(10): 3212–3219.
703:(22): 6655–6661.
535:Propionibacterium
489:of 12 genes, the
471:metabolic pathway
461:Granadaene is an
277:conjugated system
239:Chemical compound
237:
236:
69:Interactive image
2091:
2058:
2057:
2051:
2043:
2033:
2005:
1999:
1998:
1988:
1956:
1950:
1949:
1943:
1935:
1925:
1915:
1891:
1885:
1884:
1878:
1870:
1860:
1850:
1825:
1819:
1818:
1812:
1804:
1794:
1753:
1747:
1746:
1740:
1732:
1722:
1690:
1684:
1683:
1673:
1641:
1632:
1631:
1621:
1611:
1587:
1581:
1580:
1570:
1553:(6): 1265–1281.
1544:
1535:
1526:
1525:
1519:
1511:
1509:
1507:
1494:
1453:
1447:
1446:
1440:
1432:
1414:
1390:
1384:
1383:
1377:
1369:
1359:
1349:
1334:Front. Microbiol
1325:
1319:
1318:
1312:
1304:
1294:
1284:
1269:Front. Microbiol
1260:
1254:
1253:
1247:
1239:
1221:
1197:
1191:
1190:
1180:
1140:
1131:
1130:
1120:
1088:
1082:
1081:
1071:
1047:
1041:
1040:
1030:
998:
992:
991:
981:
949:
936:
935:
929:
921:
919:
917:
905:
899:
898:
892:
883:
877:
876:
870:
862:
852:
835:(8): 2674–2677.
829:J Clin Microbiol
820:
814:
813:
811:
809:
788:
779:
773:
772:
762:
739:J Clin Microbiol
730:
721:
720:
691:
685:
684:
674:
649:(9): 6367–6370.
634:
609:virulence factor
557:group where the
463:organic compound
447:phenotypic trait
423:for many years.
376:in granada broth
216:
201:
195:
189:
183:
176:Chemical formula
116:
105:
91:
71:
26:
19:
2099:
2098:
2094:
2093:
2092:
2090:
2089:
2088:
2064:
2063:
2062:
2061:
2044:
2007:
2006:
2002:
1958:
1957:
1953:
1936:
1893:
1892:
1888:
1871:
1827:
1826:
1822:
1805:
1755:
1754:
1750:
1733:
1692:
1691:
1687:
1643:
1642:
1635:
1589:
1588:
1584:
1542:
1537:
1536:
1529:
1512:
1505:
1503:
1455:
1454:
1450:
1433:
1392:
1391:
1387:
1370:
1327:
1326:
1322:
1305:
1262:
1261:
1257:
1240:
1199:
1198:
1194:
1142:
1141:
1134:
1090:
1089:
1085:
1049:
1048:
1044:
1000:
999:
995:
951:
950:
939:
922:
915:
913:
907:
906:
902:
895:MMWR Recomm Rep
890:
885:
884:
880:
863:
822:
821:
817:
807:
805:
786:
781:
780:
776:
732:
731:
724:
697:Bioorg Med Chem
693:
692:
688:
636:
635:
626:
621:
586:
459:
443:
437:Granadaene and
332:tetrahydrofuran
273:
271:Characteristics
240:
233:
228:
214:
204:
198:
192:
186:
178:
164:
161:
156:
155:
144:
141:
140:
137:
131:
130:
119:
106:
94:
74:
61:
45:
12:
11:
5:
2097:
2095:
2087:
2086:
2081:
2076:
2066:
2065:
2060:
2059:
2000:
1951:
1886:
1820:
1748:
1685:
1656:(4): 488–505.
1633:
1596:Microorganisms
1582:
1527:
1448:
1405:(2): 418–430.
1385:
1320:
1275:: Art 848490.
1255:
1212:(6): 388–394.
1192:
1132:
1103:(3): 181–198.
1097:Microbiol. Rev
1083:
1062:(2): 125–128.
1042:
993:
964:(5): 932–946.
937:
900:
878:
815:
774:
745:(1): 105–107.
722:
686:
623:
622:
620:
617:
585:
582:
458:
455:
451:granada medium
442:
435:
417:alpha-carotene
348:granada medium
272:
269:
238:
235:
234:
229:
225:standard state
222:
219:
218:
212:
206:
205:
202:
196:
190:
184:
179:
174:
171:
170:
166:
165:
163:
162:
159:
151:
150:
149:
146:
145:
143:
142:
138:
135:
134:
126:
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120:
118:
117:
109:
107:
99:
96:
95:
93:
92:
84:
82:
76:
75:
73:
72:
64:
62:
55:
52:
51:
47:
46:
39:
33:
32:
28:
27:
13:
10:
9:
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475:biosynthesis
467:S.agalactiae
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328:acetonitrile
293:
281:double bonds
274:
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247:trivial name
242:
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50:Identifiers
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2074:Rhamnosides
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1763:Nat. Commun
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479:fatty acids
169:Properties
17:Granadaene
2068:Categories
1699:J Mol Biol
619:References
605:eukaryotic
539:A.jensenii
431:sulphureus
429:Laetiporus
336:chloroform
255:isoprenoid
243:Granadaene
210:Molar mass
80:ChemSpider
56:3D model (
37:IUPAC name
1841:(1): 43.
1547:J Exp Med
611:for GBS.
601:cytolysin
593:hemolysin
543:A.thoenii
509:hemolysin
296:insoluble
285:ornithine
114:101411594
2079:Polyenes
2040:32861213
1995:26449711
1932:35626674
1867:36229877
1801:32198389
1729:30711542
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717:23043725
681:16957264
421:carotene
413:carotene
364:Sephadex
350:without
326:(DMSO),
304:methanol
289:rhamnose
89:78444511
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1986:4626576
1923:9139542
1858:9560721
1792:7083881
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1671:4403049
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1471:Bibcode
1357:6985545
1292:9125021
1178:2042088
1157:Bibcode
1127:6387426
979:4315905
808:15 July
672:1563658
651:Bibcode
483:enzymes
316:acetone
308:ethanol
259:pigment
253:of non-
251:polyene
245:is the
215:676.851
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320:hexane
153:SMILES
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