메뉴 건너뛰기




Volumn 3, Issue 3, 2008, Pages 399-412

Structural elucidation of pimarane and isopimarane diterpenoids: The 13C NMR contribution

Author keywords

13C NMR; Diterpenoids; ent isopimarane; ent pimarane; Isopimarane; Pimarane

Indexed keywords

CARBENE; CARBON; DITERPENOID; HYDROXYL GROUP; ISOPIMARANE DITERPENOID; PIMARANE DITERPENOID; UNCLASSIFIED DRUG;

EID: 77953977982     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0800300317     Document Type: Review
Times cited : (15)

References (95)
  • 1
    • 0034876390 scopus 로고    scopus 로고
    • Sesqui-, di-, and triterpenoids as chemosystematic markers in extant conifers- A review
    • Otto A, Wilde V. (2001) Sesqui-, di-, and triterpenoids as chemosystematic markers in extant conifers- A review. The Botanical Review, 67, 141-238.
    • (2001) The Botanical Review , vol.67 , pp. 141-238
    • Otto, A.1    Wilde, V.2
  • 3
    • 33747671376 scopus 로고    scopus 로고
    • Structures, biogenetic relationships, and cytotoxicity of pimarane-derived from Petalostigma pubescens
    • and references therein
    • Grace MH, Jin Y, Wilson GR, Coates RM. (2006) Structures, biogenetic relationships, and cytotoxicity of pimarane-derived from Petalostigma pubescens. Phytochemistry, 67, 1708-1715 and references therein.
    • (2006) Phytochemistry , vol.67 , pp. 1708-1715
    • Grace, M.H.1    Jin, Y.2    Wilson, G.R.3    Coates, R.M.4
  • 4
    • 33745957353 scopus 로고    scopus 로고
    • Kaurane and pimarane-type diterpenes from the Viguiera species inhibit vascular smooth muscle contractility
    • and references therein
    • Ambrósio SR, Tirapelli CR, Costa FB, Oliveira AM. (2006) Kaurane and pimarane-type diterpenes from the Viguiera species inhibit vascular smooth muscle contractility. Life Science, 79, 925-933 and references therein.
    • (2006) Life Science , vol.79 , pp. 925-933
    • Ambrósio, S.R.1    Tirapelli, C.R.2    Costa, F.B.3    Oliveira, A.M.4
  • 5
    • 33947673878 scopus 로고    scopus 로고
    • Structure elucidation of organic compounds from natural sources using 1D and 2D NMR techniques
    • Topçu G, Ulubelen A. (2007) Structure elucidation of organic compounds from natural sources using 1D and 2D NMR techniques. Journal of Molecular Structure, 834-836, 57-73.
    • (2007) Journal of Molecular Structure , vol.834-836 , pp. 57-73
    • Topçu, G.1    Ulubelen, A.2
  • 6
    • 33947090963 scopus 로고
    • Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. X. Pimaradienes
    • Wenkert E, Buckwalter BL. (1972) Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. X. Pimaradienes. Journal of the American Chemical Society, 94, 4367-4369.
    • (1972) Journal of the American Chemical Society , vol.94 , pp. 4367-4369
    • Wenkert, E.1    Buckwalter, B.L.2
  • 8
    • 0343905353 scopus 로고
    • Diterpenoids from Rabdosia parvifolia
    • Li Y, Chen Y. (1990) Diterpenoids from Rabdosia parvifolia. Phytochemistry, 29, 3033-3034.
    • (1990) Phytochemistry , vol.29 , pp. 3033-3034
    • Li, Y.1    Chen, Y.2
  • 10
    • 0000858962 scopus 로고
    • Six diterpenes from Vellozia compacta
    • Pinto AC, Borges C. (1983) Six diterpenes from Vellozia compacta. Phytochemistry, 22, 2011-2015.
    • (1983) Phytochemistry , vol.22 , pp. 2011-2015
    • Pinto, A.C.1    Borges, C.2
  • 12
    • 0026664734 scopus 로고
    • Antibacterial diterpenes from the leaves and seeds of Juniperus excelsa M. Bieb
    • Muhammad I, Mossa JS, El-Feraly FS. (1992) Antibacterial diterpenes from the leaves and seeds of Juniperus excelsa M. Bieb. Phytotherapy Research, 6, 261-264.
    • (1992) Phytotherapy Research , vol.6 , pp. 261-264
    • Muhammad, I.1    Mossa, J.S.2    El-Feraly, F.S.3
  • 13
    • 0030207749 scopus 로고    scopus 로고
    • A phytotoxic pimarane diterpene of Sphaeropsis sapinea f. sp. cupressi, the pathogen of a canker disease of cypress
    • Evidente A, Sparapano L, Motta A, Giordano F, Fierro O, Frisullo F. (1996) A phytotoxic pimarane diterpene of Sphaeropsis sapinea f. sp. cupressi, the pathogen of a canker disease of cypress. Phytochemistry, 42, 1541-1546.
    • (1996) Phytochemistry , vol.42 , pp. 1541-1546
    • Evidente, A.1    Sparapano, L.2    Motta, A.3    Giordano, F.4    Fierro, O.5    Frisullo, F.6
  • 16
    • 0036683823 scopus 로고    scopus 로고
    • Ceriopsins A-D, diterpenoids from Ceriops decandra
    • Anjaneyulu ASR, Rao VL. (2002) Ceriopsins A-D, diterpenoids from Ceriops decandra. Phytochemistry, 60, 777-782.
    • (2002) Phytochemistry , vol.60 , pp. 777-782
    • Anjaneyulu, A.S.R.1    Rao, V.L.2
  • 17
    • 0037322920 scopus 로고    scopus 로고
    • Ent-pimarane type diterpenes from Gnaphalium gaudichaudianum
    • DOI 10.1016/S0031-9422(02)00611-8, PII S0031942202006118
    • Meragelman TL, Silva GL, Mongelli E, Gil RR. (2003) ent-Pimarane type diterpenes from Gnaphalium gaudichaudianum. Phytochemistry, 62, 569-572. (Pubitemid 36216074)
    • (2003) Phytochemistry , vol.62 , Issue.4 , pp. 569-572
    • Meragelman, T.L.1    Silva, G.L.2    Mongelli, E.3    Gil, R.R.4
  • 18
    • 0036597395 scopus 로고    scopus 로고
    • A new neuroprotective pinusolide derivative from the leaves of Biota orientalis
    • Koo KA, Sung SH, Kim YC. (2002) A new neuroprotective pinusolide derivative from the leaves of Biota orientalis. Chemical and Pharmaceutical Bulletin, 50, 834-836.
    • (2002) Chemical and Pharmaceutical Bulletin , vol.50 , pp. 834-836
    • Koo, K.A.1    Sung, S.H.2    Kim, Y.C.3
  • 22
    • 0035341558 scopus 로고    scopus 로고
    • Ent-Pimarane derivatives from Dysoxylum hainanense
    • Luo X-D, Wu S-H, Ma Y-B, Wu DG. (2001) ent-Pimarane derivatives from Dysoxylum hainanense. Phytochemistry, 57, 131-134.
    • (2001) Phytochemistry , vol.57 , pp. 131-134
    • Luo, X.-D.1    Wu, S.-H.2    Ma, Y.-B.3    Wu, D.G.4
  • 24
    • 0344441866 scopus 로고    scopus 로고
    • Ent-Isopimarane-type diterpenoids from the New Zealand liverwort Trichocolea mollissima
    • DOI 10.1016/j.phytochem.2003.08.022
    • Nagashima F, Murakami M, Takaoka S, Asakawa Y. (2003) ent-Isopimarane-type diterpenoids from the New Zealand liverwort Trichocolea mollissima. Phytochemistry, 64, 1319-1325. (Pubitemid 37442603)
    • (2003) Phytochemistry , vol.64 , Issue.8 , pp. 1319-1325
    • Nagashima, F.1    Murakami, M.2    Takaoka, S.3    Asakawa, Y.4
  • 25
    • 0001861641 scopus 로고
    • Oryzalexin E, a diterpene phytoalexin from UV-irradiated rice leaves
    • Kato H, Kodama O, Akatsuka T. (1993) Oryzalexin E, a diterpene phytoalexin from UV-irradiated rice leaves. Phytochemistry, 33, 79-81.
    • (1993) Phytochemistry , vol.33 , pp. 79-81
    • Kato, H.1    Kodama, O.2    Akatsuka, T.3
  • 28
    • 0030847223 scopus 로고    scopus 로고
    • Diterpenoid, sesquiterpenoid and secoiridoid glucosides from Aster auriculatus
    • Changzeng W, Dequan Y. (1997) Diterpenoid, sesquiterpenoid and secoiridoid glucosides from Aster auriculatus. Phytochemistry, 45, 1483-1487.
    • (1997) Phytochemistry , vol.45 , pp. 1483-1487
    • Changzeng, W.1    Dequan, Y.2
  • 32
    • 0001211544 scopus 로고
    • Pimaradiene diterpenes from Acanthopanax koreanum
    • Kim YH, Chung BS. (1988) Pimaradiene diterpenes from Acanthopanax koreanum. Journal of Natural Products, 51, 1080-1083.
    • (1988) Journal of Natural Products , vol.51 , pp. 1080-1083
    • Kim, Y.H.1    Chung, B.S.2
  • 33
    • 0043180185 scopus 로고
    • Foliosate, a bis-diterpene and 9-epi-ent-7,15-isopimaradiene derivatives from Calceolaria foliosa
    • Chamy MC, Piovano M, Garbarino JA, Gambaro V, Miranda C. (1989) Foliosate, a bis-diterpene and 9-epi-ent-7,15-isopimaradiene derivatives from Calceolaria foliosa. Phytochemistry, 28, 571-574.
    • (1989) Phytochemistry , vol.28 , pp. 571-574
    • Chamy, M.C.1    Piovano, M.2    Garbarino, J.A.3    Gambaro, V.4    Miranda, C.5
  • 42
    • 0001000849 scopus 로고
    • Diterpenes from Calceolaria latifolia
    • Garbarino JA, Molinari A. (1990) Diterpenes from Calceolaria latifolia. Phytochemistry, 29, 3037-3039.
    • (1990) Phytochemistry , vol.29 , pp. 3037-3039
    • Garbarino, J.A.1    Molinari, A.2
  • 44
    • 0028130916 scopus 로고
    • Oryzalexin F, a diterpene phytoalexin from UV-irradiated rice leaves
    • DOI 10.1016/S0031-9422(00)97064-X
    • Kato H, Kodama O, Akatsuka T. (1994) Oryzalexin F, a diterpene phytoalexin from UV-irradiated rice leaves. Phytochemistry, 36, 299-301. (Pubitemid 2084352)
    • (1994) Phytochemistry , vol.36 , Issue.2 , pp. 299-301
    • Kato, H.1    Kodama, O.2    Akatsuka, T.3
  • 46
    • 0001196863 scopus 로고
    • Diterpenes from the timber of 20 Erythroxylum species
    • Ansell SM, Pegel KH, Taylor DAH. (1993) Diterpenes from the timber of 20 Erythroxylum species. Phytochemistry, 32, 953-959.
    • (1993) Phytochemistry , vol.32 , pp. 953-959
    • Ansell, S.M.1    Pegel, K.H.2    Taylor, D.A.H.3
  • 47
    • 33645102597 scopus 로고
    • 9-epi-ent-7,15-Isopimaradiene derivatives from Calceolaria glandulosa
    • Piovano M, Chamy MC, Garbarino JA, Gambaro V. (1989) 9-epi-ent-7,15- Isopimaradiene derivatives from Calceolaria glandulosa. Phytochemistry, 28, 2844-2845.
    • (1989) Phytochemistry , vol.28 , pp. 2844-2845
    • Piovano, M.1    Chamy, M.C.2    Garbarino, J.A.3    Gambaro, V.4
  • 48
    • 0030915047 scopus 로고    scopus 로고
    • Sphaeropsidins B and C, phytotoxic pimarane diterpenes from Sphaeropsis sapinea f. sp. cupressi and Diplodia mutila
    • Evidente A, Sparapano L, Fierro O, Bruno G, Giordano F, Motta A. (1997) Sphaeropsidins B and C, phytotoxic pimarane diterpenes from Sphaeropsis sapinea f. sp. cupressi and Diplodia mutila. Phytochemistry, 45, 705-713.
    • (1997) Phytochemistry , vol.45 , pp. 705-713
    • Evidente, A.1    Sparapano, L.2    Fierro, O.3    Bruno, G.4    Giordano, F.5    Motta, A.6
  • 51
    • 0009476406 scopus 로고
    • Nuclear magnetic resonance spectroscopy. Carbon-13 chemical shifts in cycloalkanones
    • Weigert FJ, Roberts JD. (1970) Nuclear magnetic resonance spectroscopy. Carbon-13 chemical shifts in cycloalkanones. Journal of the American Chemical Society, 92, 1347-1350.
    • (1970) Journal of the American Chemical Society , vol.92 , pp. 1347-1350
    • Weigert, F.J.1    Roberts, J.D.2
  • 55
    • 0004543519 scopus 로고
    • Diterpenes with pimarane and cleistanthane skeleton from Vellozia piresiana
    • Pinto AC, Peixoto EM, Fiorani GM. (1984) Diterpenes with pimarane and cleistanthane skeleton from Vellozia piresiana Phytochemistry, 23, 1293-1296.
    • (1984) Phytochemistry , vol.23 , pp. 1293-1296
    • Pinto, A.C.1    Peixoto, E.M.2    Fiorani, G.M.3
  • 57
    • 0006262941 scopus 로고
    • Diterpene acids from Mikania triangularis
    • Cruz FG, Roque NF. (1992) Diterpene acids from Mikania triangularis. Phytochemistry, 31, 2793-2796.
    • (1992) Phytochemistry , vol.31 , pp. 2793-2796
    • Cruz, F.G.1    Roque, N.F.2
  • 61
  • 62
    • 0026656899 scopus 로고
    • Isolation and structure elucidation of a new isopimarane from Pulicaria wightiana
    • Chiplunkar YG, Nagasampagi BA. (1992) Isolation and structure elucidation of a new isopimarane from Pulicaria wightiana. Journal of Natural Products, 55, 1328-1329.
    • (1992) Journal of Natural Products , vol.55 , pp. 1328-1329
    • Chiplunkar, Y.G.1    Nagasampagi, B.A.2
  • 65
    • 0001749199 scopus 로고
    • Sandaracopimarene derivatives from Senecio subrubriflorus
    • Bohlmann F, Zdero C. (1982) Sandaracopimarene derivatives from Senecio subrubriflorus. Phytochemistry, 21, 1697-1700.
    • (1982) Phytochemistry , vol.21 , pp. 1697-1700
    • Bohlmann, F.1    Zdero, C.2
  • 67
    • 4644340335 scopus 로고
    • Diterpenoids from Salvia wiedemannii
    • Topçu G, Ulubelen A. (1990) Diterpenoids from Salvia wiedemannii. Phytochemistry, 29, 2346-2348.
    • (1990) Phytochemistry , vol.29 , pp. 2346-2348
    • Topçu, G.1    Ulubelen, A.2
  • 68
  • 71
    • 77953984470 scopus 로고
    • Chemical examination of Premna species: Part VII-Constituents of root bark of Premna latifolia var. cuneata
    • Rao CB, Raju GVS, Krishna PG, Chari VM. (1982) Chemical examination of Premna species: Part VII-Constituents of root bark of Premna latifolia var. cuneata. Indian Journal of Chemistry, 21B, 294-298.
    • (1982) Indian Journal of Chemistry , vol.21 B , pp. 294-298
    • Rao, C.B.1    Raju, G.V.S.2    Krishna, P.G.3    Chari, V.M.4
  • 72
    • 0028028525 scopus 로고
    • Rearranged isopimarenes and other diterpenoids from Satureja gilliesii
    • Labbé C, Castillo M, Fainia F, Coll J, Connolly JD. (1994) Rearranged isopimarenes and other diterpenoids from Satureja gilliesii. Phytochemistry, 36, 735-738.
    • (1994) Phytochemistry , vol.36 , pp. 735-738
    • Labbé, C.1    Castillo, M.2    Fainia, F.3    Coll, J.4    Connolly, J.D.5
  • 77
    • 77953978282 scopus 로고
    • 13C NMR of diterpenes: Use of the C-19 methyl group as a probe for locating a tetrasubstituted double bond
    • 13C NMR of diterpenes: use of the C-19 methyl group as a probe for locating a tetrasubstituted double bond. Magnetic Resonance in Chemistry, 25, 1090-1091.
    • (1987) Magnetic Resonance in Chemistry , vol.25 , pp. 1090-1091
    • Taran, M.1    Arreguy-San Miguel, B.2    Delmond, B.3
  • 78
    • 77954026107 scopus 로고
    • Configurationally dependent hydroxyl group effects on 13C nuclear magnetic resonance chemical shifts of olefinic carbons in cyclic six-membered allylic alcohols
    • Kaufman TS. (1988) Configurationally dependent hydroxyl group effects on 13C nuclear magnetic resonance chemical shifts of olefinic carbons in cyclic six-membered allylic alcohols. Canadian Journal of Chemistry, 66, 3128-3131.
    • (1988) Canadian Journal of Chemistry , vol.66 , pp. 3128-3131
    • Kaufman, T.S.1
  • 79
    • 77953984469 scopus 로고
    • 13C NMR of isopimarane diterpenes: 8,9-epoxyketones
    • Pinto AC, Abla MA, Pereira AL. (1989) 13C NMR of isopimarane diterpenes: 8,9-epoxyketones. Química Nova, 12, 388-389.
    • (1989) Química Nova , vol.12 , pp. 388-389
    • Pinto, A.C.1    Abla, M.A.2    Pereira, A.L.3
  • 86
    • 77953998204 scopus 로고
    • La configuracion de C(15) en ent-15,16-dihidroxi-ros-5-enos (ent-8,5-friedopimar-5-en-15,16-dioles)
    • Garcia-Alvarez MC, Rodriguez B. (1982) La configuracion de C(15) en ent-15,16-dihidroxi-ros-5-enos (ent-8,5-friedopimar-5-en-15,16-dioles). Anales de Química, 78, 214-219.
    • (1982) Anales de Química , vol.78 , pp. 214-219
    • Garcia-Alvarez, M.C.1    Rodriguez, B.2
  • 87
    • 0001749146 scopus 로고
    • 8(14),15-Sandaracopimaradiene-2á,18-diol, a minor constituent of the Rwandese medicinal plant Tetradenia riparia
    • Puyvelde LV, Kimpe N, Borremans F, Zhang W, Schamp N. (1987) 8(14),15-Sandaracopimaradiene-2á,18-diol, a minor constituent of the Rwandese medicinal plant Tetradenia riparia. Phytochemistry, 26, 493-495.
    • (1987) Phytochemistry , vol.26 , pp. 493-495
    • Puyvelde, L.V.1    Kimpe, N.2    Borremans, F.3    Zhang, W.4    Schamp, N.5
  • 90
    • 0027987088 scopus 로고
    • Diterpenoids of Juniperus foetidissima unripe berries
    • Sakar MK, San Feliciano A. (1994). Diterpenoids of Juniperus foetidissima unripe berries. Fitoterapia, 65, 304-306.
    • (1994) Fitoterapia , vol.65 , pp. 304-306
    • Sakar, M.K.1    San Feliciano, A.2
  • 93
    • 0031984792 scopus 로고    scopus 로고
    • The microbiological transformation of a 9-epi-entpimaradiene diterpene by Gibberella fujikuroi
    • Fraga BM, González P, Hernández MG, Chamy MC, Garbarino JA. (1998) The microbiological transformation of a 9-epi-entpimaradiene diterpene by Gibberella fujikuroi. Phytochemistry, 47, 211-215.
    • (1998) Phytochemistry , vol.47 , pp. 211-215
    • Fraga, B.M.1    González, P.2    Hernández, M.G.3    Chamy, M.C.4    Garbarino, J.A.5
  • 95
    • 0000733603 scopus 로고
    • ent-Pimaranes, ent-kauranes, heliangolides and other constituents of three Helianthus species
    • Herz W, Kulanthaivel P. (1984) ent-Pimaranes, ent-kauranes, heliangolides and other constituents of three Helianthus species. Phytochemistry, 23, 1453-1459.
    • (1984) Phytochemistry , vol.23 , pp. 1453-1459
    • Herz, W.1    Kulanthaivel, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.