Comprehensive Profiling of Phenolic Compounds in White and Red Chinese Bayberries (Morella rubra Sieb. et Zucc.) and Their Developmental Variations Using Tandem Mass Spectral Molecular Networking.

Chemical structural characterization of phenolic compounds from the red ("Biqi") and white ("Shuijing") bayberries was carried out in the present study. With the aid of Global Natural Products Social Molecular Networking (GNPS), 18 flavonoid glycosides and 13 proanthocyanidins (PACs) in bayberry extracts were tentatively identified. Three cyanidin-3-glucoside derivatives (cyanidin-acetylapiosyl-glucoside, catechin-cyanidin-3-glucoside, and gallocatechin-cyanidin-3-glucoside), two quercetin derivatives (quercetin-3-arabinoside and quercetin-3-glucuronide), patuletin-7-glucoside, and individual PACs consisting of (epi)catechin or (epi)gallocatechin units were reported for the first time in bayberry fruits. In addition, "Biqi" exhibited a considerable increase of flavonoid glycoside content together with a dramatic decrease in the content of PACs in mature fruits, while "Shuijing" showed a decrease in levels of PACs but failed to accumulate flavonoid glycosides during fruit development.

Phytochemicals with Added Value from Morella and Myrica Species.

Terrestrial plants, due to their sessile nature, are highly exposed to environmental pressure and therefore need to produce very effective molecules that enable them to survive all the threats. Myrica and Morella (Myricaceae) are taxonomically close genera, which include species of trees or shrubs with edible fruits that exhibit relevant uses in traditional medicine. For instance, in Chinese or Japanese folk medicine, they are used to treat diarrhea, digestive problems, headache, burns, and skin diseases. A wide array of compounds isolated from different parts of Myrica and/or Morella species possess several biological activities, like anticancer, antidiabetic, anti-obesity, and cardio-/neuro-/hepatoprotective activities, both in vitro and in vivo, with myricanol, myricitrin, quercitrin, and betulin being the most promising. There are still many other compounds isolated from both genera whose biological activities have not been evaluated, which represents an excellent opportunity to discover new applications for those compounds and valorize Morella/Myrica species.

Diarylheptanoid Glycosides of Morella salicifolia Bark.

A methanolic extract of Morella salicifolia bark was fractionated by various chromatographic techniques yielding six previously unknown cyclic diarylheptanoids, namely, 7-hydroxymyricanol 5-O-ß-d-glucopyranoside (1), juglanin B 3-O-ß-d-glucopyranoside (2), 16-hydroxyjuglanin B 17-O-ß-d-glucopyranoside (3), myricanone 5-O-ß-d-gluco-pranosyl-(1→6)-ß-d-glucopyranoside (4), neomyricanone 5-O-ß-d-glucopranosyl-(1→6)-ß-d-glucopyranoside (5), and myricanone 17-O-α-l-arabino-furanosyl-(1→6)-ß-d-glucopyranoside (6), respectively, together with 10 known cyclic diarylheptanoids. The structural diversity of the diarylheptanoid pattern in M. salicifolia resulted from varying glycosidation at C-3, C-5, and C-17 as well as from substitution at C-11 with hydroxy, carbonyl or sulfate groups, respectively. Structure elucidation of the isolated compounds was achieved on the basis of one- and two-dimensional nuclear magnetic resonance (NMR) as well as high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) analyses. The absolute configuration of the glycosides was confirmed after hydrolysis and synthesis of O-(S)-methyl butyrated (SMB) sugar derivatives by comparison of their ¹H-NMR data with those of reference sugars. Additionally, absolute configuration of diarylheptanoid aglycones at C-11 was determined by electronic circular dichroism (ECD) spectra simulation and comparison with experimental CD spectra after hydrolysis.

Morella serrata (Lam.) Killick stabilizes biomembrane and rejuvenates sexual competence in male Wistar rats.

ETHNOPHARMACOLOGICAL RELEVANCE: Morella serrata L. is an indigenous medicinal plant to South and southern Africa with folkloric applications as aphrodisiac, laxative, antimicrobial, anti-inflammatory, analgesic, anti-hypertensive, antitussive and antidiabetic agent. AIM OF THE STUDY: This study evaluated the membrane stabilization and aphrodisiac potentials of its aqueous root extract in male Wistar rats. MATERIALS AND METHODS: While the membrane stabilization of the extract was investigated against bovine erythrocytes (BE), the male rats for the aphrodisiac study were randomized into five groups with animals in group 1 given sterile placebo and served as control. The rats in group 2 were treated with 7.14mg/kg body weight of PowMaxM, while animals in groups 3, 4 and 5 were administered with the extract (100, 200 and 400mg/kg, respectively). All treatments (1mL) were done once daily for 4 weeks via oral gavaging and their mating behavioural, testicular, spermatogenetic and antioxidant parameters were evaluated. RESULTS: With the exception of the mount, intromission and post ejaculatory latencies that were dose-dependently reduced by the extract, other mating parameters were significantly improved when compared with the control. Similar patterns of significant improvement were also observed on the testes-body weight ratio, quality and viability of sperm cells as well as testicular concentrations of proteins, cholesterol, glycogen, testosterone, follicle stimulating hormone, leuitenizing hormone and glutathione (reduced) subsequent to treatment with the extract. Although, administration of M. serrata had no significant (p>0.05) effect on the testicular activity of gamma glutamyl transferase, those of lactate dehydrogenase, phosphatases (alkaline and acid), superoxide dismutase and catalase were significantly (p<0.05) induced in the treated animals. The extract also conferred respective significant (p<0.05) membrane stabilization potential of 66.02% and 60.87% on the BE against hypotonic solution and heat-induced hemolysis relative to 62.14% and 40.19% for ibuprofen. The effect elicited by the extract at the tested doses could partly be attributed to its antioxidant and adaptogenic constituents. CONCLUSION: The data presented in this study have enriched biochemical information on the root extract of M. serrata as a viable source of phytonutrients that could be potentially useful for the development of aphrodisiac drugs, and thus lending scientific credence to its much touted sex enhancing attributes by the Basothos of the eastern Free State Province of South Africa.

Purification of Flavonoids from Chinese Bayberry (Morella rubra Sieb. et Zucc.) Fruit Extracts and α-Glucosidase Inhibitory Activities of Different Fractionations.

Chinese bayberry (Morella rubra Sieb. et Zucc.) fruit have a diverse flavonoid composition responsible for the various medicinal activities, including anti-diabetes. In the present study, efficient simultaneous purification of four flavonoid glycosides, i.e., cyanidin-3-O-glucoside (1), myricetin-3-O-rhamnoside (2), quercetin-3-O-galactoside (3), quercetin-3-O-rhamnoside (4), from Chinese bayberry pulp was established by the combination of solid phase extract (SPE) by C18 Sep-Pak(®) cartridge column chromatography and semi-preparative HPLC (Prep-HPLC), which was followed by HPLC and LC-MS identification. The purified flavonoid glycosides, as well as different fractions of fruit extracts of six bayberry cultivars, were investigated for α-glucosidase inhibitory activities. The flavonol extracts (50% methanol elution fraction) of six cultivars showed strong α-glucosidase inhibitory activities (IC50 = 15.4-69.5 µg/mL), which were higher than that of positive control acarbose (IC50 = 383.2 µg/mL). Four purified compounds 1-4 exerted α-glucosidase inhibitory activities, with IC50 values of 1444.3 µg/mL, 418.8 µg/mL, 556.4 µg/mL, and 491.8 µg/mL, respectively. Such results may provide important evidence for the potential anti-diabetic activity of different cultivars of Chinese bayberry fruit and the possible bioactive compounds involved.

Recent Breakthroughs in the Antioxidant and Anti-Inflammatory Effects of Morella and Myrica Species.

Oxidative stress is one of the risk factors for the development of several chronic diseases, such as diabetes, cancer, cardiovascular and neurodegenerative diseases. Antioxidants are therefore highly sought and can be seen as a type of preventive medicine against several diseases. Myrica and Morella genus (Myricaceae) are taxonomically very close and their species are trees or shrubs with edible fruits that exhibit relevant uses in traditional medicine, for instance in Chinese or Japanese folk medicine they are used to treat diarrhea, digestive problems, headache, burns and skin diseases. Nearly 36 compounds were isolated from different morphological parts of Myrica and/or Morella species and their antioxidant and anti-inflammatory activities evaluated. Thirteen of these compounds exhibit greater effects than the positive controls used. Adenodimerin A was the most active compound reported (in a 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay EC50= 7.9 ± 0.3 µM). These results are just one aspect of the antioxidant and anti-inflammatory evaluations reported regarding Myrica and Morella species, so a comprehensive overview on the current status, highlighting the antioxidant health promoting effect of these species, their key antioxidant compounds as well as the compounds with protective effects against oxidative stress related diseases such as inflammation, is relevant.

Medicinal potential of Morella serata (Lam.) Killick (Myricaceae) root extracts: biological and pharmacological activities.

BACKGROUND: Morella serata is a South African medicinal plant used in the treatment of microbial infections and to enhance male sexual performance. There is dearth of information in scientific literature on its efficacy and safety. METHODS: In the present study, the root extracts were investigated for the phytochemicals that may be present the antibacterial, anticandida activity using 96 wells microtitre plate method and cytotoxicity using brine shrimp (Artemia salina) lethality assay. RESULTS: The qualitative phytochemical screening revealed the presence of tannins, saponins, flavonoids, terpenoids and steroids. All the extracts including water inhibited both Gram positive and Gram negative bacteria strains at minimum inhibitory concentrations (MIC) ranging from 0.09 - 6.25 mgmL-1. The best activity was observed in the acetone extract inhibiting all the bacteria tested at MIC range of 0.09 - 0.78 mgmL-1 except Shigella flexneri KZN that was inhibited at 1.56 mgmL-1. Similarly, all the extracts suppressed the growth of all Candida species and Trichophyton mucoides at MIC ranging from 0.13 - 3.13 mgmL-1. The cytotoxicity assay revealed potent cytotoxic potential of M. serata methanol and ethanol root extracts by displaying LC50 of 0.26 and 0.18 µgmL-1 respectively. CONCLUSION: The results obtained from the present study indicated broad spectrum antimicrobial activity and justifies the use of the plant in the treatment of infectious diseases. Also the species could be a good natural source of antitumor compounds considering its lethality against brine shrimp nauplii.

Three new cyclic diarylheptanoids and other phenolic compounds from the bark of Myrica rubra and their melanogenesis inhibitory and radical scavenging activities.

Ten cyclic diarylheptanoids (1-10), including three new compounds: myricanone 5-O-alpha-L-arabinofuranosyl-(1-->6)-beta-D-glucopyranoside (7), myricanone 17-O-beta-D-(6'-O-galloyl)-glucopyranoside (8), and 16-methoxy acerogenin B 9-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (10), along with two flavonoids (11, 12), were isolated from the extracts of Myrica rubra (Myricaceae) bark. The structures of new compounds were determined on the basis of spectroscopic methods. On evaluation of compounds 1-12 against the melanogenesis in the B16 melanoma cells, six compounds, 3, 5, 7, 8, 10, and 12, exhibited inhibitory effects with 30-56% reduction of melanin content at 25 microg/mL with no or very weak toxicity to the cells (82-103% of cell viability at 25 microg/mL). In addition, upon evaluation of compounds 1-12 against the scavenging activities of free radicals [against the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical], seven compounds, 1, 3, 5, 6, 8, 11, and 12, showed potent scavenging activity [IC(50) 2-21 microM (0.6-7.3 microg/mL)].

Shifts in litterfall and dominant nitrogen sources after expansion of shrub thickets.

Woody encroachment into herbaceous ecosystems is emerging as an important ecological response to global change. A primary concern is alterations in C and N cycling and associated variations across a variety of ecosystems. We quantified seasonal variation in litterfall and litter N concentration in Morella cerifera shrub thickets to assess changes in litterfall and associated N input after shrub expansion on an Atlantic coast barrier island. We also used the natural abundance of (15)N to estimate the proportion of litterfall N originating from symbiotic N fixation. Litterfall for shrub thickets ranged from 8,991 +/- 247 to 3,810 +/- 399 kg ha(-1) year(-1) and generally declined with increasing thicket age. Litterfall in three of the four thickets exceeded previous estimates of aboveground annual net primary production in adjacent grasslands by 300-400%. Leaf N concentration was also higher after shrub expansion and, coupled with low N resorption efficiency and high litterfall, resulted in a return of as much as 169 kg N ha(-1) year(-1) to the soil. We estimated that approximately 70% of N returned to the soil was from symbiotic N fixation resulting in an ecosystem input of between 37 and 118 kg ha(-1) year(-1) of atmospheric N depending on site. Considering the extensive cover of shrub thickets on Virginia barrier islands, N fixation by shrubs is likely the largest single source of N to the system. The shift from grassland to shrub thicket on barrier islands results in a substantial increase in litterfall and foliar N concentration that will likely have a major impact on the size and cycling of ecosystem C and N pools. Increasing C and N availability in these nutrient-poor soils is likely to permanently reduce cover of native grasses and alter community structure by favoring species with greater N requirements.

Composition and cytotoxic activity of the leaf essential oil of Comptonia peregrina (L.) Coulter.

Comptonia peregrina (L.) Coulter, a native plant from Canada used in traditional medicine against cancer, was extracted by hydrodistillation. Two fractions were collected, one over 0-30 min and one over 30-60 min, to assess the influence of time of hydrodistillation on the composition of essential oil. The chemical composition of these two extracts was determined by GC and GC-MS analyses. Fifty five components were identified: beta-caryophyllene (23.69% and 15.16%) and alpha-humulene (9.67% and 7.43%) were the major components in the 0-30 min and 30-60 min fractions, respectively, while beta-myrcene was detected in a higher amount in the 0-30 min fraction (12.58%) than in the 30-60 min fraction (0.15%). The cytotoxic activities of these fractions were assessed against human lung carcinoma cell line A-549 and human colon adenocarcinoma cell line DLD-1. Only the 30-60 min fraction was found to be active against both tumor cell lines, with GI(50) values of 66 +/- 12 microg/mL for A-549 and of 46 +/- 7 microg/mL for DLD-1. Two sesquiterpenes present in the oil, alpha-humulene and (E)-nerolidol, have been found to be cytotoxic against both tumor cell lines.

Antidiabetic principles of natural medicines. V. Aldose reductase inhibitors from Myrcia multiflora DC. (2): Structures of myrciacitrins III, IV, and V.

Following the characterization of myrciacitrins I and II and myrciaphenones A and B, three new flavanone glucosides, myrciacitrins III, IV, and V, were isolated from the leaves of Brazilian Myrcia multiflora. The structures of new myrciacitrins were elucidated on the basis of physicochemical and chemical evidence. Myrciacitrins were found to show potent inhibitory activity on aldose reductase.