Frontiers in Medicinal Chemistry

Volume: 6

Bis and Tris Indole Alkaloids from Marine Organisms: New Leads for Drug Discovery

Author(s): Leena Gupta, Archna Talwar and P. M. S. Chauhan

Pp: 361-385 (25)

DOI: 10.2174/9781608054640113060016

* (Excluding Mailing and Handling)

Abstract

The marine organisms are a rich source of varied natural products with unique functionality. Marine natural products chemistry has undergone an explosive growth during the past three decades. A variety of natural products of new molecular structures with diverse biological activities have been reported from marine flora and fauna, thus ensuring for us motivation in the search of newer natural products. The bis and trisindole alkaloids are a class of marine natural products that show unique promise in the development of new drug leads.3-hydroxy staurosporine 51, an indolo carbazole having powerful antiproliferative activity. Hamacanthin A 1 and B 2, pyrazinone alkaloids have significant antimicrobial activity. Coscinamides 60-62 and Chondriamides 63-65 an indolic enamides which have anti-HIV and cytotoxic activity respectively. Gelluisine A 66 and B 67, trisindole alkaloids have strong anti-serotonin activity and strong affinity with somatostatin and neuropeptide Y receptors in receptor-binding assays. This report reviews the literature on these alkaloids from marine origin and highlights the isolation, structure, latest synthesis and specific biological activities include: cytotoxicity, antiviral, antiparasitic, serotonin antagonism and other pharmacological activities of sixty-nine bis and trisindole alkaloids.


Keywords: Bis and trisindole alkaloids, enamides, indolocarbazoles.

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      • 13. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
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      • 11. app/Models/ContentAccess.php:647
      • 12. app/Http/Controllers/ChapterController.php:1478
      • 13. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 14. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
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      • 13. app/Models/UserAccess/UserAccess.php:1266
      • 14. app/Http/Controllers/ChapterController.php:1518
      • 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 <= 51413955 and j.to_ip >=51413955 )) and ((j.from_date <= 1739834828 and j.to_date >= 1739834828 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 4722) 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 <= 51413955 and j.to_ip >=51413955 )) and ((j.from_date <= 1739834828 and j.to_date >= 1739834828 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 4722) 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 <= 51413955 and j.to_ip >=51413955 )) and ((j.from_date <= 1739834828 and j.to_date >= 1739834828 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 4722)
      600μsalphaeurekaselec_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` = 1146 and `b`.`banner_from_date` <= 1739834828 and `b`.`banner_to_date` >= 1739834828 and `b`.`banner_status` = 'A' order by `b`.`banner_id` desc
      1.09msalphaeurekaselec_live_10_06_2022Banner.php#95
      Bindings
      • 0: 1
      • 1: B
      • 2: 1146
      • 3: 1739834828
      • 4: 1739834828
      • 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='873ddb207e46de8d32c04d33a34bafeb'
      250μsalphaeurekaselec_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
    3Keywords.php#?
    App\Models\Chapter
    1Chapter.php#?
    App\Models\Ebook
    1Ebook.php#?
        _token
        GSPYVenHXTrDsE64TzReiLoJjaSJZs8dLpAs3mEE
        uc_cart_id
        873ddb207e46de8d32c04d33a34bafeb
        _previous
        array:1 [ "url" => "https://alpha.eurekaselect.com/chapter/4722" ]
        _flash
        array:2 [ "old" => [] "new" => [] ]
        PHPDEBUGBAR_STACK_DATA
        []
        path_info
        /chapter/4722
        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:17 [ "x-https" => array:1 [ 0 => "1" ] "host" => array:1 [ 0 => "alpha.eurekaselect.com" ] "priority" => array:1 [ 0 => "u=0, i" ] "cookie" => array:1 [ 0 => "wayfindertarget=eyJpdiI6InZVNFJVNW9JWGpqYTVDd3NvSDljZXc9PSIsInZhbHVlIjoiUzl5a1lFcWttOFBrN24xTktobzRQK1B0RXFMWk4xKzZXajFJWU5zTVMxYz0iLCJtYWMiOiI3ZDhhOWIxYTYzYTk3NWQ2NzgxN2I0NDlhNTk4YTIzYzQxZmEyMTg2YjA1NTMyOTRkYWQ1MTU0YzNmOGM4NTU3IiwidGFnIjoiIn0%3Dwayfindertarget=eyJpdiI6InZVNFJVNW9JWGpqYTVDd3NvSDljZXc9PSIsInZhbHVlIjoiUzl5a1lFcWttOFBrN24xTktobzRQK1B0RXFMWk4xKzZXajFJWU5zTVMxYz0iLCJtYWMiOiI3ZDhhOWIxYTYzYTk3" ] "accept-encoding" => array:1 [ 0 => "gzip, deflate, br, zstd" ] "sec-fetch-dest" => array:1 [ 0 => "document" ] "sec-fetch-user" => array:1 [ 0 => "?1" ] "sec-fetch-mode" => array:1 [ 0 => "navigate" ] "sec-fetch-site" => array:1 [ 0 => "none" ] "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" ] "sec-ch-ua-platform" => array:1 [ 0 => ""Windows"" ] "sec-ch-ua-mobile" => array:1 [ 0 => "?0" ] "sec-ch-ua" => array:1 [ 0 => ""HeadlessChrome";v="129", "Not=A?Brand";v="8", "Chromium";v="129"" ] "cache-control" => array:1 [ 0 => "no-cache" ] "pragma" => array:1 [ 0 => "no-cache" ] ]
        request_cookies
        0 of 0
        array:1 [ "wayfindertarget" => null ]
        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 => "Mon, 17 Feb 2025 23:27:08 GMT" ] "set-cookie" => array:2 [ 0 => "XSRF-TOKEN=eyJpdiI6InlhQmJSZkZYTTdWSWM4WmtqUks0V3c9PSIsInZhbHVlIjoiMzdjQ2pSaU1HNlg3amE4M3FudmtYS1h5YTk1WEZHZksvNFBpck1VK3FZT2dyYU5HaEROT0U2eUVyRHZvaHJYZzZ4TzJWWlVubHVVS1NqL0pHT3JKc0trSTlaZXV6WE1kekVQUEVKRjByUndtQ1FXSVJiTkxZVFR0d3ZTT3lKNG4iLCJtYWMiOiIzZGQxOGQ2OGI5OGM1YjA2N2Q2YmI2NjAxZTQxMWNhMDEzOGU2NzhiNTQwZDI3YmJlZWU4NmVhOTRmN2VjNjI5IiwidGFnIjoiIn0%3D; expires=Thu, 20 Feb 2025 11:27:08 GMT; Max-Age=216000; path=/; secure; samesite=laxXSRF-TOKEN=eyJpdiI6InlhQmJSZkZYTTdWSWM4WmtqUks0V3c9PSIsInZhbHVlIjoiMzdjQ2pSaU1HNlg3amE4M3FudmtYS1h5YTk1WEZHZksvNFBpck1VK3FZT2dyYU5HaEROT0U2eUVyRHZvaHJYZzZ4TzJWW" 1 => "alphaeurekaselectnet_session=eyJpdiI6IjFhYXI4ZWhDVk1JLzNhN2RtSmYvNlE9PSIsInZhbHVlIjoieTVOL2FoQ1lUaVA3MGhleTJxN3c2S2RoQUE3UXlpSUc1NWpJdURoSnY1V0lheGVraFE5SW9Bb2hCVVhVa05Mc3hMblVoaDFweHRkNFRMMXRxblltQkIyN2dicERPNGFiZ3REck1sa216NDhNdHFFUyt1TUY4VUkxNTl1WVBhNTkiLCJtYWMiOiJhMzRiN2FmNDRmNDY5ZjQ2Y2ZlYjI4NGNkM2YwZjJmN2MwMDNjYjBlMWNmMzAxZmVlYjMyNWE0YjY3MzNmZDVmIiwidGFnIjoiIn0%3D; path=/; secure; httponly; samesite=laxalphaeurekaselectnet_session=eyJpdiI6IjFhYXI4ZWhDVk1JLzNhN2RtSmYvNlE9PSIsInZhbHVlIjoieTVOL2FoQ1lUaVA3MGhleTJxN3c2S2RoQUE3UXlpSUc1NWpJdURoSnY1V0lheGVraFE5SW9Bb2h" ] "Set-Cookie" => array:2 [ 0 => "XSRF-TOKEN=eyJpdiI6InlhQmJSZkZYTTdWSWM4WmtqUks0V3c9PSIsInZhbHVlIjoiMzdjQ2pSaU1HNlg3amE4M3FudmtYS1h5YTk1WEZHZksvNFBpck1VK3FZT2dyYU5HaEROT0U2eUVyRHZvaHJYZzZ4TzJWWlVubHVVS1NqL0pHT3JKc0trSTlaZXV6WE1kekVQUEVKRjByUndtQ1FXSVJiTkxZVFR0d3ZTT3lKNG4iLCJtYWMiOiIzZGQxOGQ2OGI5OGM1YjA2N2Q2YmI2NjAxZTQxMWNhMDEzOGU2NzhiNTQwZDI3YmJlZWU4NmVhOTRmN2VjNjI5IiwidGFnIjoiIn0%3D; expires=Thu, 20-Feb-2025 11:27:08 GMT; path=/; secureXSRF-TOKEN=eyJpdiI6InlhQmJSZkZYTTdWSWM4WmtqUks0V3c9PSIsInZhbHVlIjoiMzdjQ2pSaU1HNlg3amE4M3FudmtYS1h5YTk1WEZHZksvNFBpck1VK3FZT2dyYU5HaEROT0U2eUVyRHZvaHJYZzZ4TzJWW" 1 => "alphaeurekaselectnet_session=eyJpdiI6IjFhYXI4ZWhDVk1JLzNhN2RtSmYvNlE9PSIsInZhbHVlIjoieTVOL2FoQ1lUaVA3MGhleTJxN3c2S2RoQUE3UXlpSUc1NWpJdURoSnY1V0lheGVraFE5SW9Bb2hCVVhVa05Mc3hMblVoaDFweHRkNFRMMXRxblltQkIyN2dicERPNGFiZ3REck1sa216NDhNdHFFUyt1TUY4VUkxNTl1WVBhNTkiLCJtYWMiOiJhMzRiN2FmNDRmNDY5ZjQ2Y2ZlYjI4NGNkM2YwZjJmN2MwMDNjYjBlMWNmMzAxZmVlYjMyNWE0YjY3MzNmZDVmIiwidGFnIjoiIn0%3D; path=/; secure; httponlyalphaeurekaselectnet_session=eyJpdiI6IjFhYXI4ZWhDVk1JLzNhN2RtSmYvNlE9PSIsInZhbHVlIjoieTVOL2FoQ1lUaVA3MGhleTJxN3c2S2RoQUE3UXlpSUc1NWpJdURoSnY1V0lheGVraFE5SW9Bb2h" ] ]
        session_attributes
        0 of 0
        array:5 [ "_token" => "GSPYVenHXTrDsE64TzReiLoJjaSJZs8dLpAs3mEE" "uc_cart_id" => "873ddb207e46de8d32c04d33a34bafeb" "_previous" => array:1 [ "url" => "https://alpha.eurekaselect.com/chapter/4722" ] "_flash" => array:2 [ "old" => [] "new" => [] ] "PHPDEBUGBAR_STACK_DATA" => [] ]
        ClearShow all
        Date ↕MethodURLData
        #12025-02-17 23:27:08GET/chapter/4722112195