239:
628:
24:
681:
797:
559:
517:
456:
366:
793:, Δ-capnellene-8β,10α-diol is advantageous in its selectivity for the COX isoenzyme COX-2, avoiding many of the gastrointestinal side effects associated with the inhibition of COX-1. This fact would allow for the administration of Δ-capnellene-8β,10α-diol in higher doses, potentially offering significant relief from neuropathic pain.
530:-tricycloundecane ring system. Consequently, the first known isolation of a capnellane derivative was not capnellene but a capnellanol. As part of an ongoing search for terpenoids from marine sources, Kaisin et al. (1974) characterized the most abundant terpenoid, Δ-capnellene-3β,8β,10α-triol, from colonies of
586:
and the settlement of larvae on the coral’s surface. However, the details of this defense mechanism have not been extensively explored. Although the natural synthesis of capnellene and its derivatives is not yet understood, the sesquiterpene hydrocarbon precapnelladiene has been isolated from the
549:
Kaisin et al. (1974) coined the name “capnellane” for the hydrocarbon skeleton on which the molecule was based. However, Shiekh et al. (1976) also claim to have originated the name. The first isolation of the hydrocarbon form, Δ9-capnellene, was achieved in 1978. Since then, numerous groups have
692:
Since the 1960s, marine organisms with robust chemical defense systems have been targeted for “molecular mining,” a method of drug discovery that probes organisms of interest for useful compounds. Chemical agents involved in the defense systems of these organisms often exhibit antibacterial,
599:
Capnellene has been a popular target for synthesis due to its molecular architecture, its role in the defense mechanism of soft corals, and the challenge posed by the high degree of stereochemical sophistication and the complexity of the undecane skeleton. In 1981, the first stereocontrolled
788:
behavior in the mouse model for neuropathic pain in a dose-dependent manner. Additionally, treatment with Δ-capnellene-8β,10α-diol inhibited the up-regulation of immunoreactivity in the mouse model, specifically targeting the production of COX-2. Unlike many
1072:
Sheikh, Y; Singy, G.; Kaisin, M.; Eggert, H.; Djerassi, Carl; Tursch, B.; Daloze, D.; Braekman, J.C. (1976). "Terpenoids—LXXI, Chemical studies of marine invertebrates—XIV. Four representatives of a novel sesquiterpene class—the capnellane skeleton".
873:
Mehta, Goverdhan.; Murthy, A. Narayana.; Reddy, D. Sivakumar.; Reddy, A. Veera. (1986). "A general approach to linearly fused triquinane natural products. Total syntheses of (.+-.)-hirsutene, (.+-.)-coriolin, and (.+-.)-capnellene".
600:
synthesis of (±)-Δ-capnellene was performed in nine steps, with an overall yield of 60%. Their starting reagent was a dimethylated cyclopentenyl carboxaldehyde and the overall synthesis took the form of a series of pentane ring
577:
is a widely distributed genus of soft coral, found primarily in the tropical reefs of
Indonesia. These corals produce a variety of sterols, sesquiterpenes and diterpenes. Specifically, the capnellanol derivatives found in
1291:
Little, R. Daniel; Carroll, Gary L.; Petersen, Jeffrey L. (1983). "Total synthesis of the marine natural product .DELTA.9(12)-capnellene. Reversal of regiochemistry in the intramolecular 1,3-diyl trapping reaction".
1017:
Kaisin, M; Sheikh, Y.M.; Durham, L.J.; Djerassi, C.; Tursch, B.; Daloze, D.; Braekman, J.C.; Losman, D.; Karlsson, R. (1974). "Capnellane - a new tricyclic sesquiterpene skeleton from the soft coral ?".
693:
anti-inflammatory, and chemotherapeutic properties. Capnellene derivatives and their terrestrial counterparts, hirsutanes, demonstrate antibacterial and antitumor properties with pharmacological potential.
669:. The second 5-membered ring is formed via Nazarov cyclization, and the product is prepared for a second palladium-catalyzed coupling. This step yields another divinyl ketone, which can be cyclized to an
1319:
Crisp, G. T.; Scott, William J.; Stille, John K. (1984). "Palladium-catalyzed carbonylative coupling of vinyl triflates with organostannanes. A total synthesis of (.+-.)-.DELTA.9(12)-capnellene".
634:
Since the first synthesis, many investigators have successfully assembled capnellene and its derivatives. Approaches to this synthesis are diverse, and include central steps such as annululation,
1350:; Down, John; Gayler, Ken R.; Satkunanathan, Narmatha; Khalil, Zeinab (December 2006). "Therapeutic applications of conotoxins that target the neuronal nicotinic acetylcholine receptor".
120:
1100:
Ayanoglu, E; Gebreyesus, T.; Beechan, C.M.; Djerassi, Carl; Kaisin, M. (1978). "Terpenoids LXXV. Δ9(12)-capnellene, a new sesquiterpene hydrocarbon from the soft coral ? ?".
1210:
Ayanoglu, Eser; Gebreyesus, Tarakegn; Beechan, Curtis M.; Djerassi, Carl (1979). "Terpenoids—LXXVI1Precapnelladiene, a possible biosynthetic precursor of the capnellane skeleton".
665:. The readily prepared trimethylcyclopentanone can be converted into vinyl triflate, which is coupled with vinylstannane in the first palladium-catalyzed step to yield the desired
764:
transmission, the neuronal process that responds noxious stimuli. Two capnellene derivatives Δ-capnellene-8β,10α-diol and 8α-acetoxy-Δ-capnellene-10α-ol demonstrate potential as
742:
cell lines, while 3β-acetoxycapnellene-8β,10α,14β-triol was active against leukemia cell lines. The antitumor properties of capnellene derivatives have yet to be explored
379:
1264:
Curran, D; Chen, Meng-Hsin (1985). "Radical-initiated polyolefinic cyclizations in condensed cyclopentanoid synthesis. Total synthesis of (±)-Δ9(12)-capnellene".
1426:
Morris, L; Jaspars, Marcel; Adamson, Katy; Woods, Samantha; Wallace, Heather M. (1998). "The capnellenes revisited: New structures and new biological activity".
278:
478:
unit. Capnellene is the presumed biosynthetic precursor to the capnellanols, a group of alcohols based on the capnellene skeleton that are also produced by
1488:
Jean, Yen-Hsuan; Chen, Wu-Fu; Sung, Chun-Sung; Duh, Chang-Yih; Huang, Shi-Ying; Lin, Chan-Shing; Tai, Ming-Hon; Tzeng, Shun-Fen; Wen, Zhi-Hong (2009).
1386:
947:
Ciereszko, LS (March 1962). "Chemistry of coelenterates. III. Occurrence of antimicrobial terpenoid compounds in the zooxanthellae of alcyonarians".
790:
987:
Paquette, Leo A.; Stevens, Kenneth E. (1984). "Stereocontrolled total synthesis of the triquinane marine sesquiterpene Δ9(12)-capnellene".
1453:
Chang, Chin-Hsiang; Wen, Zhi-Hong; Wang, Shang-Kwei; Duh, Chang-Yih (2008). "Capnellenes from the
Formosan Soft CoralCapnella imbricata".
1490:"Capnellene, a natural marine compound derived from soft coral, attenuates chronic constriction injury-induced neuropathic pain in rats"
253:
474:. However, it is a non-isoprenoid sesquiterpene, meaning that unlike most sesquiterpenes its structure is not based on a repeated
444:Δ-capnellene, also referred to simply as capnellene in the literature, is a monounsaturated hydrocarbon of the molecular formula C
1127:
Kaisin, M.; Braekman, J.C.; Daloze, D.; Tursch, B. (1985). "Novel acetoxycapnellenes from the alcyonacean capnella imbricata".
1237:
Singh, V; Prathap, S.; Porinchu, M. (1997). "A novel, stereospecific total synthesis of (±)-Δ9(12)-capnellene from p-cresol".
336:
494:
The capnellane group became a focal point for synthesis in the 1970s and 80’s. Scientists believed that these compounds had
452:. It features a tricyclic skeleton, a geminal dimethyl group, a tertiary methyl group, and an exocyclic methylene group.
1562:
642:, and trapping reactions. The most heavily cited synthesis in the literature involves two key intermediates formed by a
196:
217:
386:
738:
cell lines. In the same study, capnellene-8β-ol demonstrated selective toxicity for the renal leiomyoblastoma and
841:
Stille, John R.; Grubbs, Robert H. (1986). "Synthesis of (.+-.)-.DELTA.9,12-capnellene using titanium reagents".
1547:
565:
Naturally occurring alcohol derivatives of capnellene have been isolated using simple acetone extraction from
816:
1542:
1409:
760:. Neuropathic pain is characterized by damage to peripheral or central nerves that results in pathological
1552:
535:
262:
InChI=1S/C15H24/c1-10-5-6-11-9-15(4)8-7-14(2,3)13(15)12(10)11/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15-/m0/s1
1557:
777:
605:
588:
543:
627:
513:. It was also postulated that capnellenes also protect the soft coral by preventing larval settlement.
1045:
Karlsson, R. (1977). "The structure and absolute configuration of Δ9(12)-capnellene-3β,8β,10α-triol".
910:
234:
40:
639:
613:
421:
416:. Since the 1970s, capnellene has been targeted for synthesis by numerous investigators due to its
86:
1387:"Cytotoxic Activity of Capnellene-8b,10a-diol Derivatives from a Taiwanese Soft Coral Capnella sp"
674:
621:
1519:
1470:
1367:
964:
926:
651:
635:
433:
160:
1509:
1501:
1462:
1435:
1401:
1359:
1328:
1301:
1273:
1246:
1219:
1192:
1136:
1109:
1082:
1054:
1027:
996:
956:
918:
883:
850:
773:
757:
539:
301:
205:
96:
719:
643:
417:
624:, formed the third ring and a simple dehydration reaction yielded the target capnellene.
238:
140:
914:
1514:
1489:
960:
901:
Burkholder, P. R.; Burkholder, L. M. (1958). "Antimicrobial
Activity of Horny Corals".
739:
723:
666:
583:
357:
1439:
1277:
1250:
1223:
1196:
1140:
1113:
1031:
1536:
1505:
1086:
735:
495:
471:
463:
429:
185:
785:
731:
706:
483:
425:
1363:
922:
1347:
761:
756:
Capnellene derivatives have recently been identified as possible treatments for
680:
655:
510:
402:
796:
558:
23:
1058:
765:
617:
601:
570:
516:
502:
320:
151:
647:
526:
is a rich source of many non-isoprenoid sesquiterpenes, which all share the
506:
499:
413:
1523:
1474:
1405:
1371:
1183:
Liu, H; Kulkarni, M.G. (1985). "Total synthesis of (±)-Δ9(12)-capnellene".
968:
930:
420:, functionality, and the interesting geometry of the carbon skeleton. Many
1154:
768:
capable of attenuating neuropathic pain. These compounds have been shown
727:
726:(WiDr) human tumor cell lines. The diol was also effective against human
710:
702:
662:
658:
609:
475:
407:
1332:
1305:
887:
854:
744:
498:
properties, based on an earlier discovery of antimicrobial activity in
467:
455:
172:
1466:
795:
679:
626:
557:
515:
1000:
356:
Except where otherwise noted, data are given for materials in their
677:, and converted to an alkene via olefination to yield capnellene.
670:
131:
119:
109:
715:
616:
of the dienone. A regiospecific cyclopentannulation, using
454:
222:
424:
derivatives of capnellene have demonstrated potential as a
587:
same coral and research suggests that may be a biogenetic
550:
isolated both Δ-capnellene and its alcohol derivatives.
374:
1385:
Shen, Y.; Tzeng, G.; Kuo, Y.; Taha Khalil, A. (2008).
982:
980:
978:
582:
serve as a defense system by inhibiting the growth of
836:
834:
832:
830:
772:to reduce two proteins that mediate inflammation,
486:of these compounds has not yet been elucidated.
184:
95:
1012:
1010:
817:"KNApSAcK Metabolite Information - C00021780"
540:nuclear magnetic resonance (NMR) spectroscopy
8:
61:)-4,4,6a-Trimethyl-3-methylidenedecahydro-3a
942:
940:
237:
159:
15:
1513:
204:
1321:Journal of the American Chemical Society
1294:Journal of the American Chemical Society
876:Journal of the American Chemical Society
843:Journal of the American Chemical Society
604:. The second pentane ring was formed by
868:
866:
864:
808:
714:against cervical epitheloid carcinoma (
612:by vinylmagnesium bromide, followed by
283:
258:
233:
1178:
1176:
1346:Livett, Bruce G.; Sandall, David W.;
791:non-steroidal anti-inflammatory drugs
784:, Δ-capnellene-8β,10α-diol inhibited
265:Key: YZTNUNFLAAHBMK-ABHRYQDASA-N
139:
7:
1155:"Ocean Coral 'offers pain therapy'"
505:and a later study of antimicrobial
412:, a species of soft coral found in
401:is a naturally occurring tricyclic
175:
961:10.1111/j.2164-0947.1962.tb01426.x
14:
569:, a species of soft coral (order
1506:10.1111/j.1476-5381.2009.00323.x
1047:Acta Crystallographica Section B
705:derivatives exhibit significant
538:of the triol were determined by
364:
22:
1494:British Journal of Pharmacology
701:Capnellene-8β,10α-diol and its
360:(at 25 °C , 100 kPa).
337:Occupational safety and health
1:
1440:10.1016/S0040-4020(98)00784-4
1364:10.1016/j.toxicon.2006.07.023
1278:10.1016/S0040-4039(01)80834-0
1251:10.1016/S0040-4039(97)00501-7
1224:10.1016/S0040-4020(01)93720-2
1197:10.1016/S0040-4039(00)94967-0
1141:10.1016/S0040-4020(01)96474-9
1114:10.1016/S0040-4039(01)94636-2
1032:10.1016/S0040-4039(01)92222-1
989:Canadian Journal of Chemistry
923:10.1126/science.127.3307.1174
573:) known as Kenya Tree Coral.
286:C1(=C)\2(CC1)C3(2C(C)(C)CC3)C
1087:10.1016/0040-4020(76)85041-7
752:Anti-inflammatory properties
1455:Journal of Natural Products
436:and anti-tumor properties.
1579:
1059:10.1107/S0567740877005548
730:, renal leiomyoblastoma,
354:
334:
329:
294:
274:
249:
79:
71:
65:-cyclopentapentalen-3a-ol
39:
34:
21:
718:, oral epidermoid (KB),
74:Capnellene, Δ-capnellene
542:and later confirmed by
1406:10.1002/jccs.200800123
955:(5 Series II): 502–3.
821:www.knapsackfamily.com
800:
776:(COX-2) and inducible
684:
631:
620:and an intramolecular
562:
536:absolute configuration
520:
459:
799:
778:nitric oxide synthase
683:
630:
561:
544:x-ray crystallography
534:. The structure and
519:
462:Capnellene is also a
458:
325:204.357
697:Antitumor properties
41:Preferred IUPAC name
1563:Tricyclic compounds
1434:(42): 12953–12958.
1333:10.1021/ja00336a033
1306:10.1021/ja00342a048
1266:Tetrahedron Letters
1239:Tetrahedron Letters
1185:Tetrahedron Letters
1102:Tetrahedron Letters
1020:Tetrahedron Letters
915:1958Sci...127.1174B
888:10.1021/ja00272a046
855:10.1021/ja00264a058
640:radical cyclization
614:Nazarov cyclization
18:
1394:J. Chin. Chem. Soc
949:Trans N Y Acad Sci
801:
685:
632:
622:aldol condensation
567:Capnella imbricata
563:
532:Capnella imbricata
524:Capnella imbricata
521:
480:Capnella imbricata
460:
387:Infobox references
16:
1467:10.1021/np0706116
1327:(24): 7500–7606.
1272:(41): 4991–4994.
1245:(16): 2911–2914.
1191:(40): 4847–4850.
1108:(19): 1671–1674.
1026:(26): 2239–2242.
995:(11): 2415–2420.
882:(12): 3443–3452.
722:(Daoy) and colon
636:olefin metathesis
554:Natural isolation
470:that are natural
434:anti-inflammatory
395:Chemical compound
393:
392:
218:CompTox Dashboard
121:Interactive image
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1517:
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1408:. Archived from
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1337:
1336:
1316:
1310:
1309:
1288:
1282:
1281:
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1255:
1254:
1234:
1228:
1227:
1218:(9): 1035–1039.
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1201:
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1170:
1168:
1166:
1151:
1145:
1144:
1124:
1118:
1117:
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1069:
1063:
1062:
1053:(4): 1143–1147.
1042:
1036:
1035:
1014:
1005:
1004:
984:
973:
972:
944:
935:
934:
909:(3307): 1174–5.
898:
892:
891:
870:
859:
858:
838:
825:
824:
813:
774:cyclooxygenase-2
758:neuropathic pain
426:chemotherapeutic
377:
371:
368:
367:
302:Chemical formula
242:
241:
226:
224:
208:
188:
177:
163:
143:
123:
99:
29:(−)-Δ-capnellene
26:
19:
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1577:
1573:
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1567:
1548:Total synthesis
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1161:. 4 August 2009
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1081:(10): 1171–78.
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1001:10.1139/v84-415
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720:medulloblastoma
699:
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644:Stille reaction
597:
595:Total synthesis
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451:
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418:stereochemistry
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5:
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1543:Sesquiterpenes
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1534:
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1480:
1445:
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1415:on 2012-04-02.
1400:(4): 828–833.
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1300:(4): 928–932.
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1135:(6): 1067–72.
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893:
860:
849:(4): 855–856.
826:
807:
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802:
753:
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740:ovarian cancer
724:adenocarcinoma
698:
695:
689:
686:
667:divinyl ketone
596:
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584:microorganisms
555:
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491:
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482:, however the
472:semiochemicals
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1553:Cyclopentanes
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1500:(3): 713–25.
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1461:(4): 619–21.
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1358:(7): 810–29.
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141:CHEBI:192742
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766:analgesics
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