197:
24:
134:
428:
486:
Animal models suggest lupeol may act as an anti-inflammatory agent. A 1998 study found lupeol to decrease paw swelling in rats by 39%, compared to 35% for the standardized control compound
261:
InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21?,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1
988:
Bani S, Kaul A, Khan B, Ahmad SF, Suri KA, Gupta BD, Satti NK, Qazi GN (April 2006). "Suppression of T lymphocyte activity by lupeol isolated from
Crataeva religiosa".
769:
747:
1084:"Lupeol and stigmasterol suppress tumor angiogenesis and inhibit cholangiocarcinoma growth in mice via downregulation of tumor necrosis factor-α"
953:
Saleem M, Afaq F, Adhami VM, Mukhtar H (July 2004). "Lupeol modulates NF-kappaB and PI3K/Akt pathways and inhibits skin cancer in CD-1 mice".
448:
274:
712:
Surendra K, Corey EJ (October 2009). "A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol".
918:
Nigam N, Prasad S, Shukla Y (November 2007). "Preventive effects of lupeol on DMBA induced DNA alkylation damage in mouse skin".
1082:
Kangsamaksin T, Chaithongyot S, Wootthichairangsan C, Hanchaina R, Tangshewinsirikul C, Svasti J (2017-12-12). Ahmad A (ed.).
80:)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopentachrysen-9-ol
784:
636:
Starks CM, Williams RB, Norman VL, Lawrence JA, Goering MG, O'Neil-Johnson M, Hu JF, Rice SM, Eldridge GR (June 2011).
597:"Natural anti-inflammatory terpenoids in Camellia japonica leaf and probable biosynthesis pathways of the metabolome"
252:
530:
Lupeol has been found to have a contraceptive effect due to its inhibiting effect on the calcium channel of sperm (
494:
343:
879:"Protective effects of lupeol and mango extract against androgen induced oxidative stress in Swiss albino mice"
751:
229:
192:
801:
Geetha T, Varalakshmi P (June 2001). "Anti-inflammatory activity of lupeol and lupeol linoleate in rats".
1152:
154:
537:
Lupeol has also been shown to exert anti-angiogenic and anti-cancer effects via the downregulation of
1157:
838:"Flavonoids with prolyl oligopeptidase inhibitory activity isolated from Scutellaria racemosa Pers"
362:. It has several potential medicinal properties, like anticancer and anti-inflammatory activity.
1033:"Regulation of the sperm calcium channel CatSper by endogenous steroids and plant triterpenoids"
794:
1162:
174:
498:
36:
1147:
1095:
836:
Marques MR, StĂĽker C, Kichik N, TarragĂł T, Giralt E, Morel AF, Dalcol II (September 2010).
238:
420:
reported a more efficient and enantioselective total synthesis of lupeol, starting from (
8:
110:
100:
1099:
685:
Stork G, Uyeo S, Wakamatsu T, Grieco P, Labovitz J (1971). "Total synthesis of lupeol".
196:
1118:
1083:
1059:
1032:
1013:
662:
637:
814:
1123:
1064:
1005:
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729:
667:
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962:
927:
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849:
810:
721:
694:
657:
649:
608:
387:
297:
218:
1108:
854:
837:
653:
480:
452:
451:
skeletons are formed as intermediates. The reactions are catalyzed by the enzyme
403:
382:
1037:
Proceedings of the
National Academy of Sciences of the United States of America
613:
596:
568:
337:
88:(3β,13ξ)-Lup-20(29)-en-3-ol; Clerodol; Monogynol B; Fagarasterol; Farganasterol
931:
1141:
622:
524:
520:
476:
407:
185:
1049:
1127:
1068:
1009:
974:
966:
939:
904:
863:
822:
733:
671:
487:
376:
359:
767:
516:
509:
698:
322:
165:
725:
424:)-8--2,6-dimethylocta-1,5-dienyl acetate by use of a polycyclization.
1001:
538:
444:
595:
Majumder, Soumya; Ghosh, Arindam; Bhattacharya, Malay (2020-08-27).
336:
Except where otherwise noted, data are given for materials in their
505:
464:
427:
417:
23:
133:
763:
761:
563:
542:
531:
515:
As an anti-inflammatory agent, lupeol functions primarily on the
205:
777:
International
Journal of Biomedical and Pharmaceutical Sciences
145:
758:
638:"Abronione, a rotenoid from the desert annual Abronia villosa"
371:
123:
635:
501:
inhibitor at high concentrations (in the millimolar range).
835:
594:
684:
282:
CC(1CC2(C)1()3()CC4()5(C)CC(O)C(C)(C)5()CC4(C)3(C)CC2)=C
952:
876:
1030:
504:
It is an effective inhibitor in laboratory models of
768:
Margareth B. C. Gallo; Miranda J. Sarachine (2009).
877:Prasad S, Kalra N, Singh M, Shukla Y (March 2008).
370:Lupeol is found in a variety of plants, including
987:
917:
800:
479:, antimicrobial, antiinflammatory, antitumor and
1139:
217:
109:
1031:Mannowetz N, Miller MR, Lishko PV (May 2017).
475:Lupeol has a complex pharmacology, displaying
711:
439:Lupeol is produced by several organisms from
493:One study has also found some activity as a
390:. Lupeol is present as a major component in
459:leaf revealed that lupeol is produced from
748:"Solanum lycopersicum lupeol biosynthesis"
358:is a pharmacologically active pentacyclic
195:
173:
1117:
1107:
1058:
1048:
894:
853:
661:
612:
237:
783:(Special Issue 1): 46–66. Archived from
714:Journal of the American Chemical Society
687:Journal of the American Chemical Society
601:Bulletin of the National Research Centre
455:. A recent study on the metabolomics of
1140:
365:
186:
153:
590:
588:
586:
584:
208:
13:
426:
397:
14:
1174:
770:"Biological activities of Lupeol"
581:
896:10.1111/j.1745-7262.2008.00313.x
495:dipeptidyl peptidase-4 inhibitor
309:
22:
1075:
1024:
981:
946:
911:
470:
434:
340:(at 25 °C , 100 kPa).
870:
829:
740:
705:
678:
629:
467:play the role as a precursor.
315:
303:
1:
815:10.1016/S0378-8741(01)00175-1
574:
1109:10.1371/journal.pone.0189628
920:Food and Chemical Toxicology
855:10.1016/j.fitote.2010.01.018
803:Journal of Ethnopharmacology
654:10.1016/j.phytol.2010.08.004
519:system. Lupeol to decreases
7:
557:
10:
1179:
883:Asian Journal of Andrology
614:10.1186/s42269-020-00397-7
406:of lupeol was reported by
932:10.1016/j.fct.2007.06.002
334:
290:
270:
248:
93:
85:
35:
30:
21:
1050:10.1073/pnas.1700367114
967:10.1038/sj.onc.1207641
642:Phytochemistry Letters
431:
416:In 2009, Surendra and
386:. It is also found in
990:Phytotherapy Research
525:T-helper type 2 cells
523:(IL-4) production by
499:prolyl oligopeptidase
430:
1100:2017PLoSO..1289628K
699:10.1021/ja00748a068
366:Natural occurrences
330: g·mol
18:
1153:Secondary alcohols
432:
344:Infobox references
16:
1043:(22): 5743–5748.
726:10.1021/ja906335u
551:Camellia japonica
457:Camellia japonica
392:Camellia japonica
352:Chemical compound
350:
349:
135:Interactive image
1170:
1132:
1131:
1121:
1111:
1094:(12): e0189628.
1079:
1073:
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1062:
1052:
1028:
1022:
1021:
1002:10.1002/ptr.1852
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868:
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857:
833:
827:
826:
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789:
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765:
756:
755:
750:. Archived from
744:
738:
737:
709:
703:
702:
682:
676:
675:
665:
633:
627:
626:
616:
592:
554:contain lupeol.
461:squalene epoxide
441:squalene epoxide
388:dandelion coffee
329:
317:
311:
305:
298:Chemical formula
241:
221:
210:
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177:
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137:
113:
26:
19:
15:
1178:
1177:
1173:
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1167:
1158:Total synthesis
1138:
1137:
1136:
1135:
1080:
1076:
1029:
1025:
986:
982:
961:(30): 5203–14.
951:
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912:
875:
871:
834:
830:
799:
795:
787:
772:
766:
759:
746:
745:
741:
720:(39): 13928–9.
710:
706:
683:
679:
634:
630:
593:
582:
577:
560:
481:chemopreventive
473:
453:lupeol synthase
437:
404:total synthesis
400:
398:Total synthesis
383:Abronia villosa
368:
353:
346:
341:
327:
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12:
11:
5:
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1074:
1023:
980:
945:
926:(11): 2331–5.
910:
869:
828:
793:
790:on 2010-10-25.
757:
754:on 2012-07-17.
739:
704:
677:
628:
579:
578:
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572:
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569:Betulinic acid
566:
559:
556:
548:The leaves of
472:
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1163:Cyclopentanes
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996:(4): 279–87.
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561:
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540:
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521:interleukin 4
518:
513:
511:
507:
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500:
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484:
482:
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477:antiprotozoal
468:
466:
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408:Gilbert Stork
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187:ECHA InfoCard
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1040:
1036:
1026:
993:
989:
983:
958:
954:
948:
923:
919:
913:
889:(2): 313–8.
886:
882:
872:
848:(6): 552–6.
845:
841:
831:
809:(1): 77–80.
806:
802:
796:
785:the original
780:
776:
752:the original
742:
717:
713:
707:
693:(19): 4945.
690:
686:
680:
648:(2): 72–74.
645:
641:
631:
604:
600:
549:
547:
536:
529:
514:
510:skin cancers
503:
492:
488:indomethacin
485:
483:properties.
474:
471:Pharmacology
456:
438:
435:Biosynthesis
421:
415:
410:
401:
391:
381:
377:Acacia visco
375:
369:
360:triterpenoid
355:
354:
155:ChEMBL289191
94:Identifiers
86:Other names
77:
73:
69:
65:
61:
57:
53:
49:
45:
41:
1148:Triterpenes
842:Fitoterapia
517:interleukin
291:Properties
193:100.008.082
1142:Categories
607:(1): 141.
575:References
449:baccharane
402:The first
323:Molar mass
239:O268W13H3O
166:ChemSpider
122:3D model (
101:CAS Number
37:IUPAC name
623:2522-8307
539:TNF-alpha
445:Dammarane
1128:29232409
1088:PLOS ONE
1069:28507119
1018:34485412
1010:16557610
975:15122342
955:Oncogene
940:17637493
905:18097535
864:20117183
823:11378285
734:19788328
672:21617767
558:See also
506:prostate
465:squalene
175:23089061
111:545-47-1
1119:5726636
1096:Bibcode
1060:5465908
663:3099468
564:Betulin
543:VEGFR-2
532:CatSper
328:426.729
206:PubChem
17:Lupeol
1126:
1116:
1067:
1057:
1016:
1008:
973:
938:
903:
862:
821:
732:
670:
660:
621:
463:where
394:leaf.
356:Lupeol
275:SMILES
219:259846
146:ChEMBL
31:Names
1014:S2CID
788:(PDF)
773:(PDF)
422:1E,5E
418:Corey
411:et al
372:mango
253:InChI
124:JSmol
1124:PMID
1065:PMID
1006:PMID
971:PMID
936:PMID
901:PMID
860:PMID
819:PMID
730:PMID
668:PMID
619:ISSN
541:and
508:and
497:and
447:and
380:and
230:UNII
76:,13b
72:,13a
68:,11b
64:,11a
1114:PMC
1104:doi
1055:PMC
1045:doi
1041:114
998:doi
963:doi
928:doi
891:doi
850:doi
811:doi
722:doi
718:131
695:doi
658:PMC
650:doi
609:doi
534:).
209:CID
56:,7a
52:,5b
48:,5a
44:,3a
1144::
1122:.
1112:.
1102:.
1092:12
1090:.
1086:.
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1012:.
1004:.
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992:.
969:.
959:23
957:.
934:.
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922:.
899:.
887:10
885:.
881:.
858:.
846:81
844:.
840:.
817:.
807:76
805:.
779:.
775:.
760:^
728:.
716:.
691:93
689:.
666:.
656:.
644:.
640:.
617:.
605:44
603:.
599:.
583:^
545:.
527:.
512:.
490:.
443:.
413:.
374:,
313:50
307:30
60:,9
40:(1
1130:.
1106::
1098::
1071:.
1047::
1020:.
1000::
977:.
965::
942:.
930::
907:.
893::
866:.
852::
825:.
813::
781:3
736:.
724::
701:.
697::
674:.
652::
646:4
625:.
611::
316:O
310:H
304:C
126:)
78:R
74:R
70:R
66:R
62:S
58:R
54:R
50:R
46:R
42:R
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