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Analysis of cannabinoids in laser-microdissected trichomes of medicinal Cannabis sativa using LCMS and cryogenic NMR.
Phytochemistry. 2013 Mar; 87:51-9.P

Abstract

Trichomes, especially the capitate-stalked glandular hairs, are well known as the main sites of cannabinoid and essential oil production of Cannabis sativa. In this study the distribution and density of various types of Cannabis sativa L. trichomes, have been investigated by scanning electron microscopy (SEM). Furthermore, glandular trichomes were isolated over the flowering period (8 weeks) by laser microdissection (LMD) and the cannabinoid profile analyzed by LCMS. Cannabinoids were detected in extracts of 25-143 collected cells of capitate-sessile and capitate stalked trichomes and separately in the gland (head) and the stem of the latter. Δ(9)-Tetrahydrocannabinolic acid [THCA (1)], cannabidiolic acid [CBDA (2)], and cannabigerolic acid [CBGA (3)] were identified as most-abundant compounds in all analyzed samples while their decarboxylated derivatives, Δ(9)-tetrahydrocannabinol [THC (4)], cannabidiol [CBD (5)], and cannabigerol [CBG (6)], co-detected in all samples, were present at significantly lower levels. Cannabichromene [CBC (8)] along with cannabinol (CBN (9)) were identified as minor compounds only in the samples of intact capitate-stalked trichomes and their heads harvested from 8-week old plants. Cryogenic nuclear magnetic resonance spectroscopy (NMR) was used to confirm the occurrence of major cannabinoids, THCA (1) and CBDA (2), in capitate-stalked and capitate-sessile trichomes. Cryogenic NMR enabled the additional identification of cannabichromenic acid [CBCA (7)] in the dissected trichomes, which was not possible by LCMS as standard was not available. The hereby documented detection of metabolites in the stems of capitate-stalked trichomes indicates a complex biosynthesis and localization over the trichome cells forming the glandular secretion unit.

Authors+Show Affiliations

Department of Technical Biochemistry, Technical University of Dortmund, Technische Biochemie, Dortmund, Germany.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23280038

Citation

Happyana, Nizar, et al. "Analysis of Cannabinoids in Laser-microdissected Trichomes of Medicinal Cannabis Sativa Using LCMS and Cryogenic NMR." Phytochemistry, vol. 87, 2013, pp. 51-9.
Happyana N, Agnolet S, Muntendam R, et al. Analysis of cannabinoids in laser-microdissected trichomes of medicinal Cannabis sativa using LCMS and cryogenic NMR. Phytochemistry. 2013;87:51-9.
Happyana, N., Agnolet, S., Muntendam, R., Van Dam, A., Schneider, B., & Kayser, O. (2013). Analysis of cannabinoids in laser-microdissected trichomes of medicinal Cannabis sativa using LCMS and cryogenic NMR. Phytochemistry, 87, 51-9. https://doi.org/10.1016/j.phytochem.2012.11.001
Happyana N, et al. Analysis of Cannabinoids in Laser-microdissected Trichomes of Medicinal Cannabis Sativa Using LCMS and Cryogenic NMR. Phytochemistry. 2013;87:51-9. PubMed PMID: 23280038.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Analysis of cannabinoids in laser-microdissected trichomes of medicinal Cannabis sativa using LCMS and cryogenic NMR. AU - Happyana,Nizar, AU - Agnolet,Sara, AU - Muntendam,Remco, AU - Van Dam,Annie, AU - Schneider,Bernd, AU - Kayser,Oliver, Y1 - 2012/12/29/ PY - 2012/07/27/received PY - 2012/11/05/accepted PY - 2013/1/3/entrez PY - 2013/1/3/pubmed PY - 2013/8/9/medline SP - 51 EP - 9 JF - Phytochemistry JO - Phytochemistry VL - 87 N2 - Trichomes, especially the capitate-stalked glandular hairs, are well known as the main sites of cannabinoid and essential oil production of Cannabis sativa. In this study the distribution and density of various types of Cannabis sativa L. trichomes, have been investigated by scanning electron microscopy (SEM). Furthermore, glandular trichomes were isolated over the flowering period (8 weeks) by laser microdissection (LMD) and the cannabinoid profile analyzed by LCMS. Cannabinoids were detected in extracts of 25-143 collected cells of capitate-sessile and capitate stalked trichomes and separately in the gland (head) and the stem of the latter. Δ(9)-Tetrahydrocannabinolic acid [THCA (1)], cannabidiolic acid [CBDA (2)], and cannabigerolic acid [CBGA (3)] were identified as most-abundant compounds in all analyzed samples while their decarboxylated derivatives, Δ(9)-tetrahydrocannabinol [THC (4)], cannabidiol [CBD (5)], and cannabigerol [CBG (6)], co-detected in all samples, were present at significantly lower levels. Cannabichromene [CBC (8)] along with cannabinol (CBN (9)) were identified as minor compounds only in the samples of intact capitate-stalked trichomes and their heads harvested from 8-week old plants. Cryogenic nuclear magnetic resonance spectroscopy (NMR) was used to confirm the occurrence of major cannabinoids, THCA (1) and CBDA (2), in capitate-stalked and capitate-sessile trichomes. Cryogenic NMR enabled the additional identification of cannabichromenic acid [CBCA (7)] in the dissected trichomes, which was not possible by LCMS as standard was not available. The hereby documented detection of metabolites in the stems of capitate-stalked trichomes indicates a complex biosynthesis and localization over the trichome cells forming the glandular secretion unit. SN - 1873-3700 UR - https://www.unboundmedicine.com/medline/citation/23280038/Analysis_of_cannabinoids_in_laser_microdissected_trichomes_of_medicinal_Cannabis_sativa_using_LCMS_and_cryogenic_NMR_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(12)00475-X DB - PRIME DP - Unbound Medicine ER -