Hypericum spp. volatile profiling and the potential significance in the quality control of new valuable raw material

he genus Hypericum (Guttiferae) is one of the most representative species in temperate zones and Turkey is one of the most important Mediterranean sites. Due to the increasing commercial value of Hyperici herba (Hypericum perforatum), many wild Turkish Hypericum species have received currently a considerable renewed interest as potential substitutes of the well-established H. perforatum crops for their similar content in the standardization bioactives (hypericins, hyperforins, and flavonoids). The present paper reported the volatile fingerprints of three selected wild Turkish Hypericum species recently characterized as H. perforatum bioactive-like profiles but lacking of the requested well-established usage in the EU market. In this context, the volatile constituents of the three-selected Hypericum spp. were investigated as additional discriminating markers to enhance the likelihood that this adulterating plant raw material will be detected before it is incorporated into finished H. perforatum products

Models of estimation on the content of secondary metabolites in some Hypericum species

In the present study, models for estimation of the content of main secondary metabolites, namely hypericin, pseudohypericin and hyperforin were developed for Hypericum originafolium Willd, Hypericum perfoliatum L. and Hypericum montbretii Spach. growing in Northern Turkey. Wild growing plants were harvested at vegetative, floral budding, full flowering, fresh fruiting, mature fruiting stages and dissected into stem, leaf and reproductive tissues. Actual secondary metabolite contents of plant materials were measured by High Performance Liquid Chromatography method. Multiple regression analysis with Excel 2003 computer package program was performed for each species and chemicals separately to develop multiple regression models. The produced equation for predicting the content of secondary metabolites in different tissues of the species was formulized as: SMC= [a + (b1 x S) + (b2 x L) + (b3 x RP) + (b4 x S²) + (b5 x (1/RP))] where SMC is whole plant secondary metabolite content, S is stem secondary metabolite content, L is leaf secondary metabolite content, RP is secondary metabolite content of reproductive parts and a, b1, b2, b3, b4, and b5 are coefficients?. The R2 coefficient values between predicted and observed contents of secondary metabolites were determined as 0.99 for H. originafolium, 0.95–0.98 for H. perfoliatum and 0.90–0.99 for H. montbretii. All R² values and standard errors were found to be significant at the P<0.05 level

Secondary Metabolites of Hypericum leptophyllum Hochst., an Endemic Turkish Species

In the present study, the presence of the phloroglucinol derivative hyperforin, the naphthodianthrones hypericin and pseudohypericin, the phenylpropane chlorogenic acid and the flavonoids rutin, hyperoside, kaempferol, isoquercetine, quercitrine, and quercetine was investigated in Hypericum leptophyllum Hochst., an endemic Turkish species for the first time. The aerial parts representing a total of 30 individuals were collected at full flowering and dissected into floral, leaf, and stem tissues. After being dried at room temperature, the plant materials were assayed for secondary metabolite concentrations by HPLC. Aerial plant parts accumulated chlorogenic acid, hyperoside, isoquercetine, quercitrine, and quercetine, but they did not accumulate hyperforin, hypericin, pseudohypericin, rutin, and kaempferol. Accumulation levels of the detected compounds varied with plant tissues. Such kind of data could be useful for elucidation of the chemotaxonomical significance of the corresponding compounds and phytochemical evaluation of this endemic species

Chemical and morphological diversity among wild populations of Hypericum aviculariifolium Jaub. et Spach subsp. depilatum (Freyn et Bornm.) N. Robson var. depilatum

In this study, the chemical and morphological diversity among eleven wild populations of Hypericum aviculariifolium Jaub. et Spach subsp. depilatum (Freyn et Bornm.) N. Robson var. depilatum, an endemic Turkish species was studied. These populations were investigated for their contents of hypericin, pseudohypericin, hyperforin, the chlorogenic, neochlorogenic, caffeic and 2,4-dihydroxybenzoic acids, hyperoside, quercitrin, isoquercitrin, avicularin, 13,118 biapigenin, (+)-catechin and (-)-epicatechin as well as for their morphological traits, including density of leaf light and dark glands, leaf area, leaf length/width ratio and plant height. The top two-thirds of the plants representing thirty individuals was harvested at full flowering from eleven sites and analyzed for the content of bioactive compounds by high-performance liquid chromatography after being dried at room temperature. Morphological characterization of the wild populations was performed on twenty randomly selected individuals from each plant-growing locality. The content of the tested compounds, except for caffeic acid and avicularin, and some morphological traits, namely, the density of leaf translucent glands and black nodules and leaf area varied significantly with the investigated populations. It was observed that hypericin and pseudohypericin contents were connected positively with leaf black nodule density, but negatively with leaf area and the contents of hyperforin, quercitrin and 13,118-biapigenin were correlated positively with leaf translucent gland density. Data presented here could be useful in determining future targets for further wide-ranging studies on this endemic species as well as in identifying superior germplasm in terms of high chemical content

Chemical composition of Hypericum pruinatum Boiss. and Bal. from wild populations of Northern Turkey

The present study was conducted to determine the variation in the content of several plant chemicals, namely hyperforin, hypericin, pseudohypericin, chlorogenic acid, rutin, hyperoside, isoquercetine, kaempferol, quercitrine and quercetine among five Hypericum pruinatum Boiss. & Bal. populations from Northern Turkey. The aerial parts representing a total of 30 shoots were collected at full flowering. After dried at room temperature, they were assayed for the chemicals by HPLC and the presence of isoquercetine and kaempferol in this species was reported by us for the first time. The populations varied significantly in chemical contents. Plants from Ladik population produced the highest amount of hypericin, chlorogenic acid, hyperoside, isoquercetine, quercitrine and quercetine. Hyperforin and rutin of whole shoots reached the highest level in Cankiri population. The chemical variation among the populations and plant parts was discussed as possible results of different genetic and environmental factors

Factors affecting the variation of bioactive compounds in Hypericum species

The genus Hypericum (Hypericaceae) consists of 484 species from 36 sections with worldwide distribution in different areas. Turkey is considered as hot spot for diversity of Hypericum genus. Despite numerous publications, Hypericum species still attracted considerable scientific interest due to pharmaceutically relevant secondary metabolites: naphthodianthrones, acylphloroglucinol derivatives, phenolic acids, flavonoid glycosides, biflavonoids, and some other valuable constituents. Phytochemical investigations carried out on different Hypericum species provided highly heterogeneous results. The content of bioactive compounds varies significantly due to many internal and external factors, including plant organs, phenological stage, genetic profile, environmental abiotic and biotic factors, such as growing site, light, temperature, radiation, soil drought and salinity, pathogens, and herbivores attack. The variations in content of bioactive compounds in plants are regarded as the main problem in the standardization of Hypericum-derived pharmaceuticals and dietary supplements. The review discusses the main factors contributing to the variations of bioactive compounds and what kind of modulations can increase quality of Hypericum raw material

Hypericum leptophyllum Hochst., an Endemic Turkish Species

In the present study, the presence of the phloroglucinol derivative hyperforin, the naphthodianthrones hypericin and pseudohypericin, the phenylpropane chlorogenic acid and the flavonoids rutin, hyperoside, kaempferol, isoquercetine, quercitrine, and quercetine was investigated in Hypericum leptophyllum Hochst., an endemic Turkish species for the first time. The aerial parts representing a total of 30 individuals were collected at full flowering and dissected into floral, leaf, and stem tissues. After being dried at room temperature, the plant materials were assayed for secondary metabolite concentrations by HPLC. Aerial plant parts accumulated chlorogenic acid, hyperoside, isoquercetine, quercitrine, and quercetine, but they did not accumulate hyperforin, hypericin, pseudohypericin, rutin, and kaempferol. Accumulation levels of the detected compounds varied with plant tissues. Such kind of data could be useful for elucidation of the chemotaxonomical significance of the corresponding compounds and phytochemical evaluation of this endemic species

Changes in the content of bioactive substances among Hypericum montbretii populations from Turkey

In the present study, we investigated the variation in the content of seventeen secondary metabolites among Hypericum montbretii Spach., Hypericaceae, populations from five different growing zones in Turkey for the first time.The plants were collected at full flowering, and after they were dried at room temperature, they were assayed for chemical contents by HPLC. Chemical constituents of plants varied significantly among populations except for 2,4-dihydroxybenzoic acid which was accumulated at similar levels. Plants from population - 1 yielded the highest amount of hypericin and pseudohypericin (1.27 and 2.97 mg/g, respectively) while hyperforin and adhyperforin accumulations were the highest in plants from population - 2 (6.64 and 1.24 mg/g, respectively). (+)-Catechin and (-)-epicatechin were accumulated at significantly higher levels by plants of population - 4 (1.54 and 4.35 mg/g, respectively). The highest accumulation level of the rest compounds namely, chlorogenic and neochlorogenic acids, amentoflavone, hyperoside, isoquercitrin, quercitrin, quercetin, avicularin and rutin was reached in plants from population-5 (2.64, 4.37, 2.35, 10.26, 3.52, 4.37, 1.55, 1.56 and 20.54 mg/g, respectively). The pronounced chemical diversity between populations is discussed to possibly be the result of different environmental, morphological and genetic factors

Morphogenetic and phenological changes in phenolic content of Hypericum leptophyllum, an endemic Turkish species

Jakstas, Valdas/0000-0001-7627-6263WOS: 000376827700003The present study was conducted to determine the morphogenetic and phenologic variations in the content of the main bioactive compounds in Hypericum leptophyllum Hochst., an endemic species from Turkish flora. Wild plants were harvested at five phenological stages: vegetative, floral budding, full flowering, fresh fruiting, and mature fruiting, and assayed for chemical content by HPLC. Results indicated that H. leptophyllum did not accumulate hypericin, pseudohypericin, hyperforin, and adhyperforin. the phenolic content in whole plants increased generally during plant phenology and higher accumulation levels were observed at flowering. Among the reproductive organs, amentoflavone, quercetin, avicularin, and hyperoside contents were the highest in floral buds (2.09, 2.18, 0.55, and 2.62 mg g-1 dry mass ( DM), respectively). Leaves harvested at the floral budding stage produced the highest content of chlorogenic acid, neochlorogenic acid, caffeic acid, and isoquercetin (53.32, 6.25, 0.03, and 1.91 mg g-1 DM, respectively), while leaves of plants at the vegetative stage of plant development accumulated the highest content of 2,4- dihydroxybenzoic acid and quercitrin (0.29 and 0.54 mg g(-1) DM, respectively). This is the first report of the presence of avicularin, rutin, ( C)- catechin, ( -)- epicatechin, amentoflavone, caffeic acid, neochlorogenic acid, and 2,4- dihydroxybenzoic acid in this species. Such data could be useful for the evaluation of new sources of bioactive compounds, as well as for increasing phytotaxonomic knowledge for the poorly studied Hypericum species