176:
27:
839:
Reddy, S. Divya; Siva, Bandi; Kumar, Katragunta; Babu, V.S. Phani; Sravanthi, Vemireddy; Boustie, Joel; Nayak, V. Lakshma; Tiwari, Ashok K.; Rao, CH. V.; Sridhar, B.; Shashikala, P.; Babu, K. Suresh (2019).
1051:
Silva, H.A.M.F.; Aires, A.L.; Soares, C.L.R.; Sá, J.L.F.; Martins, M.C.B.; Albuquerque, M.C.P.A.; Silva, T.G.; Brayner, F.A.; Alves, L.C.; Melo, A.M.M.A.; Silva, N.H. (2020). "Barbatic acid from
97:
724:
Robertson, Alexander; Stephenson, Richard John (1932). "222. Lichen acids. Part III. The constitution of barbatic acid and the syntheses of isorhizonic acid and methyl barbatate".
1227:
Martins, MĂ´nica
Cristina Barroso; Lima, Marcio James Gonçalves de; Silva, Flávia Pereira; Azevedo-Ximenes, Eulália; Silva, Nicácio Henrique da; Pereira, Eugênia Cristina (2010).
996:
Martins, Mônica; Silva, Monique; Silva, Hianna; Silva, Luanna; Albuquerque, Mônica; Aires, André; Falcão, Emerson; Pereira, Eugênia; de Melo, Ana; da Silva, Nicácio (2017).
438:
of barbatic acid (i.e., methyl 2-hydroxy-4-(2-hydrocy-4-methoxy-3,6-dimethylbenzoyloxy)-3,6-dimethylbenzoate, or barbatin) has been characterised. It is in the
747:
Asahina, Yasuhiko; Fuzikawa, Fukuziro (1934). "Untersuchungen ĂĽber
Flechtenstoffe, XLV. Mitteil.: Über die Identität der Coccellsäure mit der Barbatinsäure".
215:
1147:
Takahagi, Toshikazu; Ikezawa, Nobuhiro; Endo, Tsuyoshi; Ifuku, Kentaro; Yamamoto, Yoshikazu; Kinoshita, Yasuhiro; Takeshita, Shunji; Sato, Fumihiko (2006).
512:
1196:
Vivas, Mercedes; Millanes, Ana Maria; Filho Neli K., Lauro Xavier; Honda, EugĂŞnia C.; Pereira, Carlos
Vicente; Legaz, Maria-Estrella (2006).
783:
520:
560:
190:
1294:
807:
Stoeckli-Evans, H.; Blaser, D. (1991). "Structure of the methyl esters of barbatic and evernic acids: natural para-depsides".
967:"Analysis of secondary metabolites from lichen by high-performance liquid chromatography with a photodiode array detector"
199:
InChI=1S/C19H20O7/c1-8-7-13(11(4)16(20)14(8)18(22)23)26-19(24)15-9(2)6-12(25-5)10(3)17(15)21/h6-7,20-21H,1-5H3,(H,22,23)
574:
154:
1284:
297:
1269:
1274:
439:
922:
Yu, Xiang; Xi, Yin-Kai; Luo, Guo-Yong; Long, Yi; Yang, Wu-De (3 January 2022). "Synthesis of barbatic acid".
846:(lichenized ascomycetes, Parmeliaceae) using UPLC-ESI-QTOF-MS/MS and pro-apoptotic activity of barbatic acid"
596:
39:
965:
Yoshimura, Isao; Kinoshita, Yasuhiro; Yamamoto, Yoshikazu; Huneck, Siegfried; Yamada, Yasuyuki (1994).
1106:
Endo, Tsuyoshi; Takahagi, Toshikazu; Kinoshita, Yasuhiro; Yamamoto, Yoshikazu; Sato, Fumihiko (1998).
579:
1279:
493:
462:
447:
171:
551:
420:
346:
63:
1149:"Inhibition of PSII in atrazine-tolerant tobacco cells by barbatic acid, a lichen-derived depside"
1178:
1088:
947:
489:
356:
391:
name is 2-hydroxy-4-(2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy-3,6-dimethylbenzoic acid. Its
1170:
1129:
1080:
1033:
939:
877:
789:
779:
505:
477:
431:
527:, and verifying the presence of three peaks representing wavelengths of maximum absorption (λ
1244:
1160:
1119:
1072:
1023:
1013:
978:
931:
904:
867:
857:
816:
756:
729:
706:
675:
392:
313:
238:
73:
1289:
695:"XXII.—Contributions to the history of the orcins. Betorcinol and some of its derivatives"
592:
556:
497:
381:
369:
175:
117:
1233:(lichen) from Brazilian northeast: chemical characterization and antimicrobial activity"
1028:
997:
872:
841:
639:
588:
568:
564:
524:
412:
408:
351:
291:
1263:
1197:
1092:
966:
951:
643:
611:
476:
groups. The crystal structure of pure barbatic acid, determined using single crystal
465:
424:
279:
1249:
1228:
1182:
501:
435:
142:
935:
563:
at concentrations that are effective against the parasite. Barbatic acid inhibits
500:
was reported; the eight-step procedure starts with commercially available methyl
43:
2-Hydroxy-4-(2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy-3,6-dimethylbenzoic acid
1059:
schistosomicidal evaluation and ultrastructural analysis against adult worms of
607:
458:
443:
1076:
1018:
895:
Elix, John A.; Norfolk, Susan (1975). "Synthesis of para-β-orcinol depsides".
862:
820:
623:
516:
377:
266:
793:
760:
679:
555:, it may have potential use in the large-scale control and/or eradication of
619:
615:
532:
1174:
1133:
1084:
1037:
982:
943:
881:
664:"Beiträge zur Geschichte der Orcine: Betorcinol und einige seiner Derivate"
638:
experiments using various cancer cell lines suggest that barbatic acid has
26:
778:. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 48, 117, 239.
733:
710:
628:
545:
473:
469:
332:
1124:
1107:
1165:
1148:
634:
416:
321:
129:
908:
415:. In its purified crystalline form, it exists as various forms: small
606:
Laboratory experiments have demonstrated that barbatic acid has some
600:
454:
373:
317:
1108:"Inhibition of photosystem II of spinach by lichen-derived Depsides"
694:
663:
461:
and are inclined towards each other at 106.1°. There are two strong
290:
Except where otherwise noted, data are given for materials in their
549:
molluscicidal activity of barbatic acid against the human parasite
515:(HPLC) technique has been adapted to couple the HPLC output with a
388:
326:
108:
96:
86:
809:
587:
have been used to synthesise barbatic acid. The cells were given
749:
Berichte der
Deutschen Chemischen Gesellschaft (A and B Series)
354:
and
Charles Groves. The compound coccellic acid, isolated from
360:, was later shown to be the same compound as barbatic acid.
159:
523:. In this way, barbatic acid is detected by monitoring its
376:. The repeated action of this enzyme produces an 8-carbon
559:. Other research has shown that it is non-toxic to human
368:
Biosynthetically, barbatic acid is made of two units of
344:
The compound was first isolated in 1880 from the lichen
223:
CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2)C)C(=O)O)O)C)O)C)OC
998:"Barbatic acid offers a new possibility for control of
519:
to screen for lichen products based on their specific
1198:"Production of barbatic acid by immobilized cells of
543:
Some preliminary research suggests that based on the
372:
derivatives that are created by an aromatic synthase
842:"Comprehensive analysis of secondary metabolites in
834:
832:
830:
141:
567:by irreversible binding to the proteins in the
453:. In this crystal form, two highly substituted
419:prisms, long needles, or delicate thin sheets (
72:
699:Journal of the Chemical Society, Transactions
492:for barbatic acid was reported in 1975 using
8:
1237:Brazilian Archives of Biology and Technology
693:Stenhouse, John; Groves, Charles E. (1880).
662:Stenhouse, John; Groves, Charles E. (1880).
1210:Journal of the Hattori Botanical Laboratory
1153:Bioscience, Biotechnology, and Biochemistry
1112:Bioscience, Biotechnology, and Biochemistry
924:Journal of Asian Natural Products Research
324:. It is particularly common in the genera
174:
18:
1248:
1164:
1123:
1027:
1017:
871:
861:
726:Journal of the Chemical Society (Resumed)
646:activities combined with a low toxicity.
504:, producing barbatic acid in a 22% total
320:. It is in the structural class known as
654:
220:
195:
170:
16:Chemical compound found in some lichens
513:high-performance liquid chromatography
284:187 °C (369 °F; 460 K)
202:Key: NMKBRSYSHBPUPY-UHFFFAOYSA-N
116:
7:
776:Identification of Lichen Substances
472:substituents an the adjacent ester
132:
668:Justus Liebig's Annalen der Chemie
561:peripheral blood mononuclear cells
496:as a condensing agent. In 2022, a
14:
480:analysis, was reported in 2019.
250:
25:
1250:10.1590/s1516-89132010000100015
897:Australian Journal of Chemistry
294:(at 25 °C , 100 kPa).
427:is 187 °C (369 °F).
256:
244:
1:
936:10.1080/10286020.2021.2023506
622:activity against some tumour
531:) at 214, 276, and 310
1055:(lichen): Cytotoxicity and
521:ultraviolet–visible spectra
1311:
774:Huneck, Siegfried (1996).
1077:10.1016/j.tiv.2020.104771
1019:10.3390/molecules22040568
863:10.3390/molecules24122270
821:10.1107/s0108270191006340
517:photodiode array detector
288:
231:
211:
186:
56:
48:
38:
33:
24:
761:10.1002/cber.19340671103
680:10.1002/jlac.18802030304
457:rings are bridged by an
440:triclinic crystal system
330:(the beard lichens) and
1295:Dihydroxybenzoic acids
983:10.1002/PCA.2800050405
971:Phytochemical Analysis
1000:Biomphalaria glabrata
380:intermediate that is
316:that is made by some
1206:in calcium alginate"
1002:and schistosomiasis"
734:10.1039/jr9320001675
711:10.1039/ct8803700395
494:trifluoroacetic acid
1125:10.1271/bbb.62.2023
1065:Toxicology in Vitro
1061:Schistosoma mansoni
552:Schistosoma mansoni
274: g·mol
21:
1166:10.1271/bbb.70.266
357:Cladonia coccifera
298:Infobox references
19:
1285:Methoxy compounds
1118:(10): 2023–2027.
930:(12): 1150–1156.
909:10.1071/ch9751113
815:(12): 2620–2624.
785:978-3-642-85245-9
755:(11): 1793–1795.
614:activity. It has
575:Immobilised cells
478:X-ray diffraction
432:crystal structure
306:Chemical compound
304:
303:
155:CompTox Dashboard
98:Interactive image
1302:
1270:Carboxylic acids
1255:
1254:
1252:
1231:Cladia aggregata
1224:
1218:
1217:
1200:Cladonia miniata
1193:
1187:
1186:
1168:
1144:
1138:
1137:
1127:
1103:
1097:
1096:
1053:Cladia aggregata
1048:
1042:
1041:
1031:
1021:
993:
987:
986:
962:
956:
955:
919:
913:
912:
903:(5): 1113–1124.
892:
886:
885:
875:
865:
844:Usnea longissima
836:
825:
824:
804:
798:
797:
771:
765:
764:
744:
738:
737:
721:
715:
714:
690:
684:
683:
659:
580:Cladonia miniata
451:
393:chemical formula
387:Barbatic acid's
314:organic compound
273:
258:
252:
246:
239:Chemical formula
179:
178:
163:
161:
145:
134:
120:
100:
76:
29:
22:
1310:
1309:
1305:
1304:
1303:
1301:
1300:
1299:
1275:Lichen products
1260:
1259:
1258:
1226:
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1221:
1195:
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1190:
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1141:
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723:
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718:
692:
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687:
661:
660:
656:
652:
593:calcium acetate
557:schistosomiasis
541:
530:
498:total synthesis
486:
449:
411:of 360.36
406:
402:
398:
366:
342:
307:
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194:
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135:
123:
103:
90:
79:
66:
52:
51:Barbatinic acid
44:
17:
12:
11:
5:
1308:
1306:
1298:
1297:
1292:
1287:
1282:
1277:
1272:
1262:
1261:
1257:
1256:
1243:(1): 115–122.
1219:
1188:
1159:(1): 266–268.
1139:
1098:
1043:
988:
977:(4): 197–205.
957:
914:
887:
826:
799:
784:
766:
739:
716:
685:
674:(3): 285–305.
653:
651:
648:
640:antineoplastic
603:biosynthesis.
589:sodium acetate
577:of the lichen
569:photosystem II
565:photosynthesis
540:
537:
528:
525:retention time
485:
482:
466:hydrogen bonds
463:intramolecular
413:grams per mole
409:molecular mass
404:
400:
396:
365:
362:
352:John Stenhouse
341:
338:
305:
302:
301:
296:
292:standard state
289:
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172:DTXSID40170115
167:
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62:
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31:
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20:Barbatic acid
15:
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3:
2:
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859:
856:(12): e2270.
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689:
686:
681:
677:
673:
670:(in German).
669:
665:
658:
655:
649:
647:
645:
644:pro-apoptotic
641:
637:
636:
631:
630:
625:
621:
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612:antimicrobial
609:
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428:
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425:melting point
422:
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394:
390:
385:
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379:
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371:
363:
361:
359:
358:
353:
349:
348:
347:Usnea barbata
339:
337:
335:
334:
329:
328:
323:
319:
315:
311:
310:Barbatic acid
299:
293:
287:
283:
281:
280:Melting point
278:
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769:
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688:
671:
667:
657:
633:
627:
605:
584:
578:
573:
550:
544:
542:
510:
487:
468:between the
436:methyl ester
429:
386:
367:
355:
350:by chemists
345:
343:
331:
325:
309:
308:
118:CHEBI:144123
57:Identifiers
49:Other names
1280:Polyphenols
705:: 395–407.
608:antioxidant
459:ester group
444:space group
407:; it has a
370:orsellinate
232:Properties
1264:Categories
1216:: 855–863.
1071:: 104771.
1012:(4): 568.
650:References
624:cell lines
378:polyketide
364:Properties
267:Molar mass
85:3D model (
74:17636-16-7
64:CAS Number
40:IUPAC name
1093:210827117
1006:Molecules
952:245651506
850:Molecules
794:851387266
620:genotoxic
616:cytotoxic
597:precursor
571:complex.
490:synthesis
484:Synthesis
442:, in the
1204:parvipes
1183:13291222
1175:16428846
1134:27385453
1085:31935486
1057:in vitro
1038:28362351
944:34978467
882:31216770
728:: 1675.
629:in vitro
585:parvipes
546:in vitro
539:Research
502:atrarate
474:carbonyl
470:hydroxyl
421:lamellae
382:cyclized
333:Cladonia
322:depsides
1029:6154637
873:6630668
635:in vivo
446:called
434:of the
423:). Its
417:rhombic
340:History
318:lichens
272:360.362
130:PubChem
1290:Esters
1181:
1173:
1132:
1091:
1083:
1036:
1026:
950:
942:
880:
870:
792:
782:
626:. And
601:phenol
455:phenyl
374:enzyme
312:is an
216:SMILES
143:167666
34:Names
1202:var.
1179:S2CID
1089:S2CID
948:S2CID
595:as a
583:var.
506:yield
389:IUPAC
327:Usnea
191:InChI
109:ChEBI
87:JSmol
1171:PMID
1130:PMID
1081:PMID
1034:PMID
940:PMID
878:PMID
790:OCLC
780:ISBN
642:and
632:and
618:and
610:and
599:for
430:The
395:is C
1245:doi
1214:100
1161:doi
1120:doi
1073:doi
1063:".
1024:PMC
1014:doi
979:doi
932:doi
905:doi
868:PMC
858:doi
817:doi
757:doi
730:doi
707:doi
676:doi
672:203
591:or
529:max
160:EPA
133:CID
1266::
1241:53
1239:.
1235:.
1212:.
1208:.
1177:.
1169:.
1157:70
1155:.
1151:.
1128:.
1116:62
1114:.
1110:.
1087:.
1079:.
1069:65
1067:.
1032:.
1022:.
1010:22
1008:.
1004:.
973:.
969:.
946:.
938:.
928:24
926:.
901:28
899:.
876:.
866:.
854:24
852:.
848:.
829:^
813:47
811:.
788:.
753:67
751:.
703:37
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