Chemistry, Biology and Potential Applications of Honeybee Plant-Derived Products

Valuable Analytical Tools in Analysis of Honeybee Plant-Derived Compounds: Nuclear Magnetic Resonance Spectroscopy

Author(s): Clementina M.M. Santos and Artur M.S. Silva

Pp: 150-195 (46)

DOI: 10.2174/9781681082370116010008

* (Excluding Mailing and Handling)

Abstract

Over the past fifty years, Nuclear Magnetic Resonance (NMR) spectroscopy proved to be a powerful tool in the structural characterisation of bioactive compounds from natural sources. In this chapter we cover the basic theory behind each NMR technique used to determine the structure of several families of compounds (e.g. carbohydrates, phenolics and sesquiterpenoids) present in honey and propolis. We also provide basic information how 1D and 2D NMR techniques can help in the structure establishment of honeybee constituents. The 1H and 13C NMR data of several of these constituents are compiled and described, being some of them used as botanical and geographical markers. In the case of propolis, a list of compounds identified by NMR is presented. A basic overview in quantitative NMR determinations and in NMR coupled to chemometric methodologies highlights their use to detect honey adulteration and assign their authenticity.


Keywords: Adulteration, Authenticity, Botanical marker, 13C NMR, COSY, DEPT, DOSY, Geographical marker, HMBC, HMQC, 1H NMR, Honeybee, HSQC, Natural products, NMR spectroscopy, NOESY, Propolis, ROESY, Structure elucidation, TOCSY.

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      • 13. app/Models/UserAccess/UserAccess.php:1266
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      • 15. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 16. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 17. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • (select j.user_access_id,j.volume_id,j.user_id,j.from_ip,j.to_ip,j.type,j.track,"Trial Access" as access_base_text, CASE j.type WHEN 111 THEN true ELSE false END as terms_popup, "S" as content_download_type, null as restricted_user_access_key, null as restricted_user_access_type, CASE j.track WHEN 0 THEN false ELSE true END as tracksAccessByVolume,"chapter" as access_level, j.chapter_id from `user_access_chapter_trail` as `j` inner join `user_access_info` as `info` on `j`.`user_access_id` = `info`.`user_access_id` where ((j.from_ip <= 316202228 and j.to_ip >=316202228 )) and ((j.from_date <= 1740458528 and j.to_date >= 1740458528 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 9057) union (select j.user_access_id,j.volume_id,j.user_id,j.from_ip,j.to_ip,j.type,j.track,"Subscribed" as access_base_text, false as terms_popup, "S" as content_download_type, null as restricted_user_access_key, null as restricted_user_access_type, CASE j.track WHEN 0 THEN false ELSE true END as tracksAccessByVolume,"chapter" as access_level, j.chapter_id from `user_access_chapter_corporate` as `j` inner join `user_access_info` as `info` on `j`.`user_access_id` = `info`.`user_access_id` where ((j.from_ip <= 316202228 and j.to_ip >=316202228 )) and ((j.from_date <= 1740458528 and j.to_date >= 1740458528 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 9057) union (select j.user_access_id,j.volume_id,j.user_id,j.from_ip,j.to_ip,j.type,j.track,"Token Based Access" as access_base_text, false as terms_popup, "R" as content_download_type, j.uc_id as restricted_user_access_key, "v" as restricted_user_access_type, CASE j.track WHEN 0 THEN false ELSE true END as tracksAccessByVolume,"chapter" as access_level, j.chapter_id from `user_access_chapter_token` as `j` inner join `user_access_info` as `info` on `j`.`user_access_id` = `info`.`user_access_id` where ((j.from_ip <= 316202228 and j.to_ip >=316202228 )) and ((j.from_date <= 1740458528 and j.to_date >= 1740458528 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 9057)
      1msalphaeurekaselec_live_10_06_2022UserAccess.php#1266
      Backtrace
      • 13. app/Models/UserAccess/UserAccess.php:1266
      • 14. app/Http/Controllers/ChapterController.php:1549
      • 15. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 16. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 17. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • select b.banner_link, b.banner_name, b.banner_script, b.banner_remarks, b.banner_file_name, b.banner_placement, bd.content_type, bd.content_id from `tbl_banner` as `b` inner join `tbl_banner_detail` as `bd` on `bd`.`banner_id` = `b`.`banner_id` inner join `users` as `u` on `u`.`id` = `b`.`updated_by` where `b`.`banner_ebook` = 1 and `bd`.`content_type` = 'B' and `bd`.`content_id` = 1976 and `b`.`banner_from_date` <= 1740458528 and `b`.`banner_to_date` >= 1740458528 and `b`.`banner_status` = 'A' order by `b`.`banner_id` desc
      1.59msalphaeurekaselec_live_10_06_2022Banner.php#95
      Bindings
      • 0: 1
      • 1: B
      • 2: 1976
      • 3: 1740458528
      • 4: 1740458528
      • 5: A
      Backtrace
      • 13. app/Models/Banner.php:95
      • 14. app/Http/helpers.php:404
      • 17. vendor/laravel/framework/src/Illuminate/Filesystem/Filesystem.php:124
      • 18. vendor/laravel/framework/src/Illuminate/View/Engines/PhpEngine.php:58
      • 19. vendor/laravel/framework/src/Illuminate/View/Engines/CompilerEngine.php:73
    • select count(*) as aggregate from `uc_cart_products` where cart_id='99a61c10b464c8a57d421e3120dd848a'
      300μsalphaeurekaselec_live_10_06_2022Cart.php#271
      Backtrace
      • 15. app/Models/Cart.php:271
      • 16. view::layouts._header:260
      • 18. vendor/laravel/framework/src/Illuminate/Filesystem/Filesystem.php:124
      • 19. vendor/laravel/framework/src/Illuminate/View/Engines/PhpEngine.php:58
      • 20. vendor/laravel/framework/src/Illuminate/View/Engines/CompilerEngine.php:73
    App\Models\Keywords
    20Keywords.php#?
    App\Models\Chapter
    1Chapter.php#?
    App\Models\Ebook
    1Ebook.php#?
        _token
        ZPVjEGbS8VnrOKm0qudrM8MuK5LMkni9gAc60dJJ
        uc_cart_id
        99a61c10b464c8a57d421e3120dd848a
        _previous
        array:1 [ "url" => "http://alpha.eurekaselect.com/chapter/9057" ]
        _flash
        array:2 [ "old" => [] "new" => [] ]
        PHPDEBUGBAR_STACK_DATA
        []
        path_info
        /chapter/9057
        status_code
        200
        
        status_text
        OK
        format
        html
        content_type
        text/html; charset=UTF-8
        request_query
        []
        
        request_request
        []
        
        request_headers
        0 of 0
        array:8 [ "accept-encoding" => array:1 [ 0 => "gzip, deflate" ] "accept" => array:1 [ 0 => "text/html,application/xhtml+xml,application/xml;q=0.9,image/avif,image/webp,image/apng,*/*;q=0.8,application/signed-exchange;v=b3;q=0.7" ] "user-agent" => array:1 [ 0 => "Mozilla/5.0 AppleWebKit/537.36 (KHTML, like Gecko; compatible; ClaudeBot/1.0; +claudebot@anthropic.com)" ] "upgrade-insecure-requests" => array:1 [ 0 => "1" ] "cache-control" => array:1 [ 0 => "no-cache" ] "pragma" => array:1 [ 0 => "no-cache" ] "connection" => array:1 [ 0 => "keep-alive" ] "host" => array:1 [ 0 => "alpha.eurekaselect.com" ] ]
        request_cookies
        []
        
        response_headers
        0 of 0
        array:5 [ "content-type" => array:1 [ 0 => "text/html; charset=UTF-8" ] "cache-control" => array:1 [ 0 => "no-cache, private" ] "date" => array:1 [ 0 => "Tue, 25 Feb 2025 04:42:08 GMT" ] "set-cookie" => array:2 [ 0 => "XSRF-TOKEN=eyJpdiI6IjhIdk9ObzYvUFJjbnVLaU1VWFVTcVE9PSIsInZhbHVlIjoidWc3c3FJUXhqM2l1TXBpc1grZUdZS2pyVnJzeExDY1UxM1JRdmt3MHlVWDlCSGp1NEVOTE1udm1LeVBVcUpQc08yRlE3NFE3Zi9FQnNvQzdyZ2dLVk5DRUdjOXJ1bWlhWnhFcnFOZXVGL3BGSkNBMXc0Mm9NaEF3Y3U5MWUwRHQiLCJtYWMiOiJjNGRkMTFkNjJhNDQwMDViMWY5Y2IzYjJjMzc0MWQ5ZjkxNjgxMDk5ZGQyMTJlZDg4MGIxOGU1NWZiODUyODA4IiwidGFnIjoiIn0%3D; expires=Thu, 27 Feb 2025 16:42:08 GMT; Max-Age=216000; path=/; secure; samesite=laxXSRF-TOKEN=eyJpdiI6IjhIdk9ObzYvUFJjbnVLaU1VWFVTcVE9PSIsInZhbHVlIjoidWc3c3FJUXhqM2l1TXBpc1grZUdZS2pyVnJzeExDY1UxM1JRdmt3MHlVWDlCSGp1NEVOTE1udm1LeVBVcUpQc08yRlE3N" 1 => "alphaeurekaselectnet_session=eyJpdiI6InJKRmVZellBL2lVeWdtOWMvZEdQQnc9PSIsInZhbHVlIjoiM2tHN2xTRHBHelgzT1hqMzVvbTJjdlFoajVLUzgwSk41Mmx4L3RMeFl5aDM5b1IrME5NOWpadzNGYXFXZUJ0clc2QTVrN1AyUEp3dVlYN0FhbjZuRjNmUVlxektNOE1WYjBTc3dZTm9UTzFSUzhEK2x5S3h6dXpDOXJGOFZyTFoiLCJtYWMiOiJjMmY4NzlkZDliYzQwOGQwODdlYTE3NGFlZDc0OGFlODVjODAwMmFlMGM5ODI2MmNlZDFmMDhmOWNkNzIyYTUyIiwidGFnIjoiIn0%3D; path=/; secure; httponly; samesite=laxalphaeurekaselectnet_session=eyJpdiI6InJKRmVZellBL2lVeWdtOWMvZEdQQnc9PSIsInZhbHVlIjoiM2tHN2xTRHBHelgzT1hqMzVvbTJjdlFoajVLUzgwSk41Mmx4L3RMeFl5aDM5b1IrME5NOWpadzN" ] "Set-Cookie" => array:2 [ 0 => "XSRF-TOKEN=eyJpdiI6IjhIdk9ObzYvUFJjbnVLaU1VWFVTcVE9PSIsInZhbHVlIjoidWc3c3FJUXhqM2l1TXBpc1grZUdZS2pyVnJzeExDY1UxM1JRdmt3MHlVWDlCSGp1NEVOTE1udm1LeVBVcUpQc08yRlE3NFE3Zi9FQnNvQzdyZ2dLVk5DRUdjOXJ1bWlhWnhFcnFOZXVGL3BGSkNBMXc0Mm9NaEF3Y3U5MWUwRHQiLCJtYWMiOiJjNGRkMTFkNjJhNDQwMDViMWY5Y2IzYjJjMzc0MWQ5ZjkxNjgxMDk5ZGQyMTJlZDg4MGIxOGU1NWZiODUyODA4IiwidGFnIjoiIn0%3D; expires=Thu, 27-Feb-2025 16:42:08 GMT; path=/; secureXSRF-TOKEN=eyJpdiI6IjhIdk9ObzYvUFJjbnVLaU1VWFVTcVE9PSIsInZhbHVlIjoidWc3c3FJUXhqM2l1TXBpc1grZUdZS2pyVnJzeExDY1UxM1JRdmt3MHlVWDlCSGp1NEVOTE1udm1LeVBVcUpQc08yRlE3N" 1 => "alphaeurekaselectnet_session=eyJpdiI6InJKRmVZellBL2lVeWdtOWMvZEdQQnc9PSIsInZhbHVlIjoiM2tHN2xTRHBHelgzT1hqMzVvbTJjdlFoajVLUzgwSk41Mmx4L3RMeFl5aDM5b1IrME5NOWpadzNGYXFXZUJ0clc2QTVrN1AyUEp3dVlYN0FhbjZuRjNmUVlxektNOE1WYjBTc3dZTm9UTzFSUzhEK2x5S3h6dXpDOXJGOFZyTFoiLCJtYWMiOiJjMmY4NzlkZDliYzQwOGQwODdlYTE3NGFlZDc0OGFlODVjODAwMmFlMGM5ODI2MmNlZDFmMDhmOWNkNzIyYTUyIiwidGFnIjoiIn0%3D; path=/; secure; httponlyalphaeurekaselectnet_session=eyJpdiI6InJKRmVZellBL2lVeWdtOWMvZEdQQnc9PSIsInZhbHVlIjoiM2tHN2xTRHBHelgzT1hqMzVvbTJjdlFoajVLUzgwSk41Mmx4L3RMeFl5aDM5b1IrME5NOWpadzN" ] ]
        session_attributes
        0 of 0
        array:5 [ "_token" => "ZPVjEGbS8VnrOKm0qudrM8MuK5LMkni9gAc60dJJ" "uc_cart_id" => "99a61c10b464c8a57d421e3120dd848a" "_previous" => array:1 [ "url" => "http://alpha.eurekaselect.com/chapter/9057" ] "_flash" => array:2 [ "old" => [] "new" => [] ] "PHPDEBUGBAR_STACK_DATA" => [] ]
        ClearShow all
        Date ↕MethodURLData
        #12025-02-25 04:42:08GET/chapter/90571121922