Distribution of photoactive β‐carboline alkaloids across Passiflora caerulea floral organs

Abstract

This study reports valuable information regarding the presence and concentration of a series of photoactive β‐carboline (βCs) alkaloids (norharmane, harmane, harmine, harmol, harmaline, and harmalol) and their distribution across the floral age and organs of Passiflora caerulea. UHPLC–MS/MS data reported herein reveal that the βCs' content ranged from 1 to 110 μg kg−1, depending on the floral organ and age. In certain physiologically relevant organs, such as anthers, βCs' content was one order of magnitude higher than in other organs, suggesting a special role for βCs in this specific organ. βCs' content also varied in a structure‐dependent manner. Alkaloids bearing a hydroxyl group at position C(7) of the main βC ring were present at concentrations one order of magnitude higher than other βC derivatives investigated. UV–visible and fluorescence spectroscopy of the flower extracts provided complementary information regarding other biologically relevant groups of chromophores (phenolic/indolic derivatives, flavonoids/carotenes, and chlorophylls). Since flowers are constantly exposed to solar radiation, the presence of photoactive βCs in floral organs may have several (photo)biological implications that are further discussed.

Exploring potooxidative degradation pathways of harmol and harmalol alkaloids in water: effects of pH, excitation sources and atmospheric conditions

“…10 Additionally, compounds 1 and 2 are found in Passiflora caerulea floral organs ( i.e. , anthers, corona, stigmas, petals and sepals), 6 and their role in pollinator discrimination was hypothesized. 6,10…”

“…, anthers, corona, stigmas, petals and sepals), 6 and their role in pollinator discrimination was hypothesized. 6,10…”

“…b-Carbolines (bCs) are heterocycle alkaloids found in various biological systems. [1][2][3][4][5][6] The biosynthesis of bCs involves an enzymatic Pictet-Spengler condensation between tryptophan and aldehydes, leading to the formation of 1,2,3,4-tetrahydro-and 3,4-dihydro-bC derivatives. Subsequent chemical/enzymatic reactions may yield diverse bCs, including the full aromatic derivatives.…”

“…8 Notably, 7-hydroxy-1-methyl-9H-pyrido [3,4-b]indole, harmol (1), and the corresponding 3,4-dihydro-derivative, harmalol (2) (Scheme 1), are prominent constituents of Peganum harmala seed extracts 9 and floral nectar. 10 Additionally, compounds 1 and 2 are found in Passiflora caerulea floral organs (i.e., anthers, corona, stigmas, petals and sepals), 6 and their role in pollinator discrimination was hypothesized. 6,10 From the pharmacological and biochemical viewpoints, these compounds are shown to be promising pharmaceutical drugs.…”

“…10 Additionally, compounds 1 and 2 are found in Passiflora caerulea floral organs (i.e., anthers, corona, stigmas, petals and sepals), 6 and their role in pollinator discrimination was hypothesized. 6,10 From the pharmacological and biochemical viewpoints, these compounds are shown to be promising pharmaceutical drugs. 11,12 These alkaloids show antitumor, 13,14 antimicrobial, [15][16][17][18] cell growth inhibitory, 12 and in vivo and in vitro antioxidant [19][20][21] properties, among many others.…”