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Volumn 87, Issue , 2013, Pages 51-59

Analysis of cannabinoids in laser-microdissected trichomes of medicinal Cannabis sativa using LCMS and cryogenic NMR

Author keywords

Cannabinoid biosynthesis; Cannabis sativa; Capitate sessile trichome; Capitate stalked trichome; Cryogenic nuclear magnetic resonance (NMR); Gland; Laser microdissection (LMD); Liquid chromatography mass spectrometry (LCMS); Scanning electron microscopy (SEM)

Indexed keywords

CANNABINOID; CANNABIS;

EID: 84872778316     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2012.11.001     Document Type: Article
Times cited : (140)

References (45)
  • 1
    • 50549083095 scopus 로고    scopus 로고
    • Structure determination and absolute configuration of cannabichromanone derivatives from high potency Cannabis sativa
    • S.A. Ahmed, S.A. Ross, D. Slade, M.M. Radwan, I.A. Khan, and M.A. Elsohly Structure determination and absolute configuration of cannabichromanone derivatives from high potency Cannabis sativa Tetrahedron Lett. 49 2008 6050 6053
    • (2008) Tetrahedron Lett. , vol.49 , pp. 6050-6053
    • Ahmed, S.A.1    Ross, S.A.2    Slade, D.3    Radwan, M.M.4    Khan, I.A.5    Elsohly, M.A.6
  • 3
    • 0036845188 scopus 로고    scopus 로고
    • Construction of a specialized cDNA library from plant cells isolated by laser capture microdissection: Toward comprehensive analysis of the genes expressed in the rice phloem
    • DOI 10.1046/j.1365-313X.2002.01423.x
    • T. Asano, T. Masumura, H. Kusano, S. Kikuchi, A. Kurita, H. Shimada, and K. Kadowaki Construction of a specialized cDNA library from plant cells isolated by laser capture microdissection: toward comprehensive analysis of the genes expressed in the rice phloem Plant J. 32 2002 401 408 (Pubitemid 35307272)
    • (2002) Plant Journal , vol.32 , Issue.3 , pp. 401-408
    • Asano, T.1    Masumura, T.2    Kusano, H.3    Kikuchi, S.4    Kurita, A.5    Shimada, H.6    Kadowaki, K.-I.7
  • 5
    • 23044450758 scopus 로고    scopus 로고
    • Be more specific! Laser-assisted microdissection of plant cells
    • DOI 10.1016/j.tplants.2005.06.006, PII S1360138505001524
    • R.C. Day, U. Grossniklaus, and R.C. Macknight Be more specific! Laser-assisted microdissection of plant cells Trends Plant Sci. 10 2005 397 406 (Pubitemid 41059668)
    • (2005) Trends in Plant Science , vol.10 , Issue.8 , pp. 397-406
    • Day, R.C.1    Grossniklaus, U.2    Macknight, R.C.3
  • 6
    • 0042629102 scopus 로고
    • Trichomes of Cannabis sativa L. (Cannabaceae)
    • P. Dayanandan, and P.B. Kaufman Trichomes of Cannabis sativa L. (Cannabaceae) Am. J. Bot. 63 1976 578 591
    • (1976) Am. J. Bot. , vol.63 , pp. 578-591
    • Dayanandan, P.1    Kaufman, P.B.2
  • 8
    • 27844525479 scopus 로고    scopus 로고
    • Chemical constituents of marijuana: The complex mixture of natural cannabinoids
    • DOI 10.1016/j.lfs.2005.09.011, PII S002432050500891X
    • M.A. ElSohly, and D. Slade Chemical constituents of marijuana: the complex mixture of natural cannabinoids Life Sci. 78 2005 539 548 (Pubitemid 41653504)
    • (2005) Life Sciences , vol.78 , Issue.5 , pp. 539-548
    • ElSohly, M.A.1    Slade, D.2
  • 9
    • 0015487169 scopus 로고
    • Trichomes and glands of Cannabis sativa L.
    • J.W. Fairbair Trichomes and glands of Cannabis sativa L. Bull. Narc. 24 1972 29 33
    • (1972) Bull. Narc. , vol.24 , pp. 29-33
    • Fairbair, J.W.1
  • 11
    • 0032496420 scopus 로고    scopus 로고
    • Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol
    • DOI 10.1016/S0014-5793(98)00450-5, PII S0014579398004505
    • M. Fellermeier, and M.H. Zenk Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol FEBS Lett. 427 1998 283 285 (Pubitemid 28225075)
    • (1998) FEBS Letters , vol.427 , Issue.2 , pp. 283-285
    • Fellermeier, M.1    Zenk, M.H.2
  • 12
    • 67449094111 scopus 로고    scopus 로고
    • Chemistry and biological activity of tetrahydrocannabinol and its derivatives
    • T. Flemming, R. Muntendam, C. Steup, and O. Kayser Chemistry and biological activity of tetrahydrocannabinol and its derivatives Top. Heterocycl. Chem. 10 2007 1 42
    • (2007) Top. Heterocycl. Chem. , vol.10 , pp. 1-42
    • Flemming, T.1    Muntendam, R.2    Steup, C.3    Kayser, O.4
  • 13
    • 0007609108 scopus 로고
    • Secretory cavity development in glandular trichomes of Cannabis sativa L. (Cannabaceae)
    • E.S. Kim, and P.G. Mahlberg Secretory cavity development in glandular trichomes of Cannabis sativa L. (Cannabaceae) Am. J. Bot. 78 1991 220 229
    • (1991) Am. J. Bot. , vol.78 , pp. 220-229
    • Kim, E.S.1    Mahlberg, P.G.2
  • 14
    • 0030946679 scopus 로고    scopus 로고
    • Immunochemical localization of tetrahydrocannabinol (THC) in cryofixed glandular trichomes of Cannabis (Cannabaceae)
    • E.S. Kim, and P.G. Mahlberg Immunochemical localization of tetrahydrocannabinol (THC) in cryofixed glandular trichomes of Cannabis (Cannabaceae) Am. J. Bot. 84 1997 336 342 (Pubitemid 27176612)
    • (1997) American Journal of Botany , vol.84 , Issue.3 , pp. 336-342
    • Kim, E.-S.1    Mahlberg, P.G.2
  • 15
    • 2142853618 scopus 로고    scopus 로고
    • Secretory vesicle formation in the secretory cavity of glandular trichomes of Cannabis sativa L. (Cannabaceae)
    • E.S. Kim, and P.G. Mahlberg Secretory vesicle formation in the secretory cavity of glandular trichomes of Cannabis sativa L. (Cannabaceae) Mol. Cells 15 2003 387 395
    • (2003) Mol. Cells , vol.15 , pp. 387-395
    • Kim, E.S.1    Mahlberg, P.G.2
  • 16
    • 0000663594 scopus 로고
    • Quantitative-analysis of cannabinoids in the secretory product from capitate-stalked glands of Cannabis sativa L. (Cannabaceae)
    • V.S. Lanyon, J.C. Turner, and P.G. Mahlberg Quantitative-analysis of cannabinoids in the secretory product from capitate-stalked glands of Cannabis sativa L. (Cannabaceae) Bot. Gaz. 142 1981 316 319
    • (1981) Bot. Gaz. , vol.142 , pp. 316-319
    • Lanyon, V.S.1    Turner, J.C.2    Mahlberg, P.G.3
  • 17
    • 31744438843 scopus 로고    scopus 로고
    • Concise synthesis of biologically interesting (±)-cannabichromene, (±)-cannabichromenic acid, and (±)-daurichromenic acid
    • R.Y. Lee, and X. Wang Concise synthesis of biologically interesting (±)-cannabichromene, (±)-cannabichromenic acid, and (±)-daurichromenic acid Bull. Korean Chem. Soc. 26 2005 1933 1936 (Pubitemid 43175426)
    • (2005) Bulletin of the Korean Chemical Society , vol.26 , Issue.12 , pp. 1933-1936
    • Yong, R.L.1    Wang, X.2
  • 18
    • 0017848783 scopus 로고
    • 9-trans- tetrahydrocannabinol on placebo Cannabis plant material
    • G.S. Lewis, and C.E. Turner Constituents of Cannabis sativa L. 13. Stability of dosage form prepared by impregnating synthetic (-)-Delta-9-trans- tetrahydrocannabinol on placebo cannabis plant material J. Pharm. Sci. 67 1978 876 878 (Pubitemid 8361263)
    • (1978) Journal of Pharmaceutical Sciences , vol.67 , Issue.6 , pp. 876-878
    • Lewis, G.S.1    Turner, C.E.2
  • 19
    • 33846820427 scopus 로고    scopus 로고
    • Microchemical analysis of laser-microdissected stone cells of Norway spruce by cryogenic nuclear magnetic resonance spectroscopy
    • DOI 10.1007/s00425-006-0376-z
    • S.-H. Li, B. Schneider, and J. Gershenzon Microchemical analysis of laser-microdissected stone cells of Norway spruce by cryogenic nuclear magnetic resonance spectroscopy Planta 225 2007 771 779 (Pubitemid 46204241)
    • (2007) Planta , vol.225 , Issue.3 , pp. 771-779
    • Li, S.-H.1    Schneider, B.2    Gershenzon, J.3
  • 20
    • 6344294365 scopus 로고    scopus 로고
    • Accumulation of cannabinoids in glandular trichomes of Cannabis (Cannabaceae)
    • DOI 10.1300/J237v09n01-04
    • P.G. Mahlberg, and E.S. Kim Accumulation of cannabinoids in glandular trichomes of Cannabis (Cannabaceae) J. Ind. Hemp 9 2004 15 36 (Pubitemid 39384608)
    • (2004) Journal of Industrial Hemp , vol.9 , Issue.1 , pp. 15-36
    • Mahlberg, P.G.1    Eun, S.K.2
  • 22
    • 0032211987 scopus 로고    scopus 로고
    • Purification and characterization of cannabichromenic acid synthase from Cannabis sativa
    • DOI 10.1016/S0031-9422(98)00278-7, PII S0031942298002787
    • S. Morimoto, K. Komatsu, F. Taura, and Y. Shoyama Purification and characterization of cannabichromenic acid synthase from Cannabis sativa Phytochemistry 49 1998 1525 1529 (Pubitemid 28559533)
    • (1998) Phytochemistry , vol.49 , Issue.6 , pp. 1525-1529
    • Morimoto, S.1    Komatsu, K.2    Taura, F.3    Shoyama, Y.4
  • 23
    • 34547094855 scopus 로고    scopus 로고
    • Identification and characterization of cannabinoids that induce cell death through mitochondrial permeability transition in cannabis leaf cells
    • DOI 10.1074/jbc.M700133200
    • S. Morimoto, Y. Tanaka, K. Sasaki, H. Tanaka, T. Fukamizu, Y. Shoyama, Y. Shoyama, and F. Taura Identification and characterization of cannabinoids that induce cell death through mitochondrial permeability transition in Cannabis leaf cells J. Biol. Chem. 282 2007 20739 20751 (Pubitemid 47100032)
    • (2007) Journal of Biological Chemistry , vol.282 , Issue.28 , pp. 20739-20751
    • Morimoto, S.1    Tanaka, Y.2    Sasaki, K.3    Tanaka, H.4    Fukamizu, T.5    Shoyama, Y.6    Shoyama, Y.7    Taura, F.8
  • 24
    • 69249228525 scopus 로고    scopus 로고
    • Localization of enzymes of artemisinin biosynthesis to the apical cells of glandular secretory trichomes of Artemisia annua L.
    • M.E. Olsson, L.M. Olofsson, A.L. Lindahl, A. Lundgren, M. Brodelius, and P.E. Brodelius Localization of enzymes of artemisinin biosynthesis to the apical cells of glandular secretory trichomes of Artemisia annua L. Phytochemistry 70 2009 1123 1128
    • (2009) Phytochemistry , vol.70 , pp. 1123-1128
    • Olsson, M.E.1    Olofsson, L.M.2    Lindahl, A.L.3    Lundgren, A.4    Brodelius, M.5    Brodelius, P.E.6
  • 26
    • 0024259238 scopus 로고
    • Histochemical detection of hemp trichomes and their correlation with the content
    • G. Petri, P. Oroszlan, and L. Fridvalszky Histochemical detection of hemp trichomes and their correlation with the content Acta Biol. Hung. 39 1988 59 74
    • (1988) Acta Biol. Hung. , vol.39 , pp. 59-74
    • Petri, G.1    Oroszlan, P.2    Fridvalszky, L.3
  • 29
    • 41349085587 scopus 로고    scopus 로고
    • Isolation and characterization of new cannabis constituents from a high potency variety
    • M.M. Radwan, S.A. Ross, D. Slade, S.A. Ahmed, F. Zulfiqar, and M.A. ElSohly Isolation and characterization of new cannabis constituents from a high potency variety Planta Med. 74 2008 327
    • (2008) Planta Med. , vol.74 , pp. 327
    • Radwan, M.M.1    Ross, S.A.2    Slade, D.3    Ahmed, S.A.4    Zulfiqar, F.5    Elsohly, M.A.6
  • 30
    • 0015507393 scopus 로고
    • Hashish 6. Conversion of (-)-Delta1(6)-tetrahydrocannabinol to (-)-Delta1(7)-tetrahydrocannabinol-stability of (-)-Delta1- and "(-)-Delta1(6)-tetrahydrocannabinols
    • R.K. Razdan, A.J. Puttick, B.A. Zitko, and G.R. Handrick Hashish 6. Conversion of (-)-Delta1(6)-tetrahydrocannabinol to (-)-Delta1(7)- tetrahydrocannabinol-stability of (-)-Delta1- and "(-)-Delta1(6)- tetrahydrocannabinols Experientia 28 1972 121
    • (1972) Experientia , vol.28 , pp. 121
    • Razdan, R.K.1    Puttick, A.J.2    Zitko, B.A.3    Handrick, G.R.4
  • 31
    • 23144452867 scopus 로고    scopus 로고
    • Evaluation of two-dimensional electrophoresis and liquid chromatography tandem mass spectrometry for tissue-specific protein profiling of laser-microdissected plant samples (vol. 26, pg. 2729, 2005)
    • M. Schad, M.S. Lipton, P. Giavalisco, R.D. Smith, and J. Kehr Evaluation of two-dimensional electrophoresis and liquid chromatography tandem mass spectrometry for tissue-specific protein profiling of laser-microdissected plant samples (vol. 26, pg. 2729, 2005) Electrophoresis 26 2005 3406
    • (2005) Electrophoresis , vol.26 , pp. 3406
    • Schad, M.1    Lipton, M.S.2    Giavalisco, P.3    Smith, R.D.4    Kehr, J.5
  • 32
    • 33745944637 scopus 로고    scopus 로고
    • Metabolic profiling of laser microdissected vascular bundles of Arabidopsis thaliana
    • M. Schad, R. Mungur, O. Fiehn, and J. Kehr Metabolic profiling of laser microdissected vascular bundles of Arabidopsis thaliana Plant Methods 1 2005 1 10
    • (2005) Plant Methods , vol.1 , pp. 1-10
    • Schad, M.1    Mungur, R.2    Fiehn, O.3    Kehr, J.4
  • 33
    • 43549084573 scopus 로고    scopus 로고
    • Harnessing plant trichome biochemistry for the production of useful compounds
    • DOI 10.1111/j.1365-313X.2008.03432.x
    • A.L. Schilmiller, R.L. Last, and E. Pichersky Harnessing plant trichome biochemistry for the production of useful compounds Plant J. 54 2008 702 711 (Pubitemid 351678040)
    • (2008) Plant Journal , vol.54 , Issue.4 , pp. 702-711
    • Schilmiller, A.L.1    Last, R.L.2    Pichersky, E.3
  • 34
    • 33846785445 scopus 로고    scopus 로고
    • Laser microdissection and cryogenic nuclear magnetic resonance spectroscopy: An alliance for cell type-specific metabolite profiling
    • DOI 10.1007/s00425-006-0404-z
    • B. Schneider, and D. Hölscher Laser microdissection and cryogenic nuclear magnetic resonance spectroscopy: an alliance for cell type-specific metabolite profiling Planta 225 2007 763 770 (Pubitemid 46204240)
    • (2007) Planta , vol.225 , Issue.3 , pp. 763-770
    • Schneider, B.1    Holscher, D.2
  • 35
    • 4544339836 scopus 로고    scopus 로고
    • 1-tetrahydrocannabinolic acid synthase from Cannabis sativa L.
    • DOI 10.1074/jbc.M403693200
    • S. Sirikantaramas, S. Morimoto, Y. Shoyama, Y. Ishikawa, Y. Wada, Y. Shoyama, and F. Taura The gene controlling marijuana psychoactivity-molecular cloning and heterologous expression of Delta(1)-tetrahydrocannabinolic acid synthase from Cannabis sativa L. J. Biol. Chem. 279 2004 39767 39774 (Pubitemid 39258246)
    • (2004) Journal of Biological Chemistry , vol.279 , Issue.38 , pp. 39767-39774
    • Sirikantaramas, S.1    Morimoto, S.2    Shoyama, Y.3    Ishikawa, Y.4    Wada, Y.5    Shoyama, Y.6    Taura, F.7
  • 36
    • 26444467058 scopus 로고    scopus 로고
    • Tetrahydrocannabinolic acid synthase, the enzyme controlling marijuana psychoactivity, is secreted into the storage cavity of the glandular trichomes
    • DOI 10.1093/pcp/pci166
    • S. Sirikantaramas, F. Taura, Y. Tanaka, Y. Ishikawa, S. Morimoto, and Y. Shoyama Tetrahydrocannabinolic acid synthase, the enzyme controlling marijuana psychoactivity, is secreted into the storage cavity of the glandular trichomes Plant Cell Physiol. 46 2005 1578 1582 (Pubitemid 41436600)
    • (2005) Plant and Cell Physiology , vol.46 , Issue.9 , pp. 1578-1582
    • Sirikantaramas, S.1    Taura, F.2    Tanaka, Y.3    Ishikawa, Y.4    Morimoto, S.5    Shoyama, Y.6
  • 37
    • 0030055554 scopus 로고    scopus 로고
    • Purification and characterization of cannabidiolic-acid synthase from Cannabis sativa L. Biochemical analysis of a novel enzyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic acid
    • DOI 10.1074/jbc.271.29.17411
    • F. Taura, S. Morimoto, and Y. Shoyama Purification and characterization of cannabidiolic-acid synthase from Cannabis sativa L. Biochemical analysis of a novel enzyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic acid J. Biol. Chem. 271 1996 17411 17416 (Pubitemid 26244305)
    • (1996) Journal of Biological Chemistry , vol.271 , Issue.29 , pp. 17411-17416
    • Taura, F.1    Morimoto, S.2    Shoyama, Y.3
  • 38
    • 0028886934 scopus 로고
    • First direct evidence for the mechanism of Delta(1)- tetrahydricannabinolic acid biosynthesis
    • F. Taura, S. Morimoto, Y. Shoyama, and R. Mechoulam First direct evidence for the mechanism of Delta(1)-tetrahydricannabinolic acid biosynthesis J. Am. Chem. Soc. 117 1995 9766 9767
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9766-9767
    • Taura, F.1    Morimoto, S.2    Shoyama, Y.3    Mechoulam, R.4
  • 39
    • 34548481515 scopus 로고    scopus 로고
    • Phytocannabiniods in Cannabis sativa: Recent studies on biosynthetic enzymes
    • DOI 10.1002/cbdv.200790145
    • F. Taura, S. Sirikantaramas, Y. Shoyama, Y. Shoyama, and S. Morimoto Phytocannabinoids in Cannabis sativa: recent studies on biosynthetic enzymes Chem. Biodivers. 4 2007 1649 1663 (Pubitemid 47377198)
    • (2007) Chemistry and Biodiversity , vol.4 , Issue.8 , pp. 1649-1663
    • Taura, F.1    Sirikantaramas, S.2    Shoyama, Y.3    Shoyama, Y.4    Morimoto, S.5
  • 40
    • 34250179866 scopus 로고    scopus 로고
    • Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa
    • DOI 10.1016/j.febslet.2007.05.043, PII S0014579307005728
    • F. Taura, S. Sirikantaramas, Y. Shoyama, K. Yoshikai, Y. Shoyama, and S. Morimoto Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa FEBS Lett. 581 2007 2929 2934 (Pubitemid 46899035)
    • (2007) FEBS Letters , vol.581 , Issue.16 , pp. 2929-2934
    • Taura, F.1    Sirikantaramas, S.2    Shoyama, Y.3    Yoshikai, K.4    Shoyama, Y.5    Morimoto, S.6
  • 41
    • 0001702589 scopus 로고
    • Quantitative-determination of cannabinoids in individual glandular trichomes of Cannabis sativa L. (Cannabaceae)
    • J.C. Turner, J.K. Hemphill, and P.G. Mahlberg Quantitative-determination of cannabinoids in individual glandular trichomes of Cannabis sativa L. (Cannabaceae) Am. J. Bot. 65 1978 1103 1106
    • (1978) Am. J. Bot. , vol.65 , pp. 1103-1106
    • Turner, J.C.1    Hemphill, J.K.2    Mahlberg, P.G.3
  • 42
    • 0008246420 scopus 로고
    • Trichomes and cannabinoid content of developing leaves and bracts of Cannabis sativa L. (Cannabaceae)
    • J.C. Turner, J.K. Hemphill, and P.G. Mahlberg Trichomes and cannabinoid content of developing leaves and bracts of Cannabis sativa L. (Cannabaceae) Am. J. Bot. 67 1980 1397 1406
    • (1980) Am. J. Bot. , vol.67 , pp. 1397-1406
    • Turner, J.C.1    Hemphill, J.K.2    Mahlberg, P.G.3
  • 43
    • 0019785749 scopus 로고
    • Interrelationships of glandular trichomes and cannabinoid content. I. Developing pistillate bracts of Cannabis sativa L. (Cannabaceae)
    • J.C. Turner, J.K. Hemphill, and P.G. Mahlberg Interrelationships of glandular trichomes and cannabinoid content. 1. Developing pistillate bracts of Cannabis sativa L. (Cannabaceae) Bull. Narc. 33 1981 59 69 (Pubitemid 12243118)
    • (1981) Bulletin on Narcotics , vol.33 , Issue.2 , pp. 59-69
    • Turner, J.C.1    Hemphill, J.K.2    Mahlberg, P.G.3
  • 45
    • 33746139659 scopus 로고    scopus 로고
    • History of cannabis as a medicine: A review
    • DOI 10.1590/S1516-44462006000200015
    • A.W. Zuardi History of cannabis as a medicine: a review Rev. Bras. Psiquiatr. 28 2006 153 157 (Pubitemid 44086488)
    • (2006) Revista Brasileira de Psiquiatria , vol.28 , Issue.2 , pp. 153-157
    • Zuardi, A.W.1


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