Dominant Secondary Metabolites Research Articles

Comprehensive Secondary Metabolite Profiling and Antioxidant Activity of Aqueous and Ethanol Extracts of Neolamarckia cadamba (Roxb.) Bosser Fruits.

Neolamarckia cadamba (Rubiaceae) is a well-recognized medicinal plant with recorded therapeutical attributes. However, a thorough assessment of active compounds in its fruits is lacking, limiting their use and valorization in pharmacological industries. Thus, this study investigated variations in the fruits' secondary metabolite (SM) profiles, as well as antioxidant activities in aqueous (WA) and ethanol (ET) extracts. Liquid chromatography-electrospray ionization tandem mass spectrometry identified 541 SMs, of which 14 and 1 (di-O-glucosylquinic acid) were specifically detected in ET and WA, respectively. Phenolic acids (36.97%), flavonoids (28.10%), terpenoids (12.20%), and alkaloids (9.98%) were the dominant SMs. The SM profiles of the fruits in WA and ET were quite different. We revealed 198 differentially extracted (DE) metabolites between WA and ET, including 62 flavonoids, 57 phenolic acids, 45 terpenoids, 14 alkaloids, etc. Most DE flavones (36 out of 40), terpenoids (45 out of 45), and alkaloids (12 out of 14) had higher content in ET. Catechin and its derivatives, procyanidins, and tannins had higher content in WA. ABTS and DPPH assays showed that the antioxidant activity of ET was significantly higher than that of WA. Our findings will facilitate the efficient extraction and evaluation of specific active compounds in N. cadamba.

Evaluation of Biological Potency of two Endemic Species Integrated with in vitro and in silico Approches: LC-MS/MS Analysis of the Plants.

In the present study, the main phytochemical components of endemic plant extracts and inhibitory potency were screened related to different biological activities. Seven compounds were quantified, and cyanidin-3-o-glucoside was the dominant secondary metabolite in the extract of plants. The extract from P. asiae-minoris (PAM) exhibited the best enzyme inhibitory activity against BChE (1.73±0.23 μg mL-1 ), tyrosinase (2.47±0.28 μg mL-1 ), α-glucosidase (5.28±0.66 μg mL-1 ), AChE (8.66±0.86 μg mL-1 ), and ACE (19.27±1.02 μg mL-1 ). In vitro antioxidant assay, PAM extract possessed the highest activity in respect of DPPH radical scavenging (24.29±0.23 μg/mL), ABTS⋅+ scavenging (13.50±0.27 μg/mL) and FRAP reducing power (1.56±0.01 μmol TE/g extract). MIC values ranged from 1-8 mg/mL for antibacterial ability, and the PAM extract showed a stronger effect for B. subtilis, E. faecalis, and E. coli at 1 mg/mL. The antiproliferative ability of A. bartinense (AB) extract demonstrated a suppressive effect (IC50 : 70.26 μg/mL) for pancreatic cancer cell lines. According to the affinity scores analysis, the cyanidin-3-o-glucoside demonstrated the lowest docking scores against ACE, AChE, BChE, and collagenase. It was found that the PAM extract exhibited better inhibitory capabilities than A. bartinense. The P. asiae-minoris plant, reported to be in the Critically Endangered (CR) category, should be conserved by culturing, considering its biological abilities.

Root-exuded benzoxazinoids can alleviate negative plant-soil feedbacks.

Plants can suppress the growth of other plants by modifying soil properties. These negative plant-soil feedbacks are often species-specific, suggesting that some plants possess resistance strategies. However, the underlying mechanisms remain largely unknown. Here, we investigated whether benzoxazinoids, a class of dominant secondary metabolites that are exuded into the soil by maize and other cereals, allow maize plants to cope with plant-soil feedbacks. We find that three out of five tested crop species reduce maize (Zea mays L.) performance via negative plant-soil feedbacks relative to the mean across species. This effect is partially alleviated by the capacity of maize plants to produce benzoxazinoids. Soil complementation with purified benzoxazinoids restores the protective effect for benzoxazinoid-deficient mutants. Sterilization and reinoculation experiments suggest that benzoxazinoid-mediated protection acts via changes in soil biota. Substantial variation of the protective effect between experiments and soil types illustrates context dependency. In conclusion, exuded plant secondary metabolites allow plants to cope with plant-soil feedbacks. These findings expand the functional repertoire of plant secondary metabolites and reveal a mechanism by which plants can resist negative effects of soil feedbacks. The uncovered phenomenon may represent a promising avenue to stabilize plant performance in crop rotations.

Profile Volatile Compounds in Essential Oils on Different Parts of Cardamom with Antioxidant Activity

Amomum compactum Soland Ex. Maton from the Zingiberaceae, known as Java cardamom in Indonesia, is a valuable medicinal plant because of its bioactivity. This study aims to identify and evaluate the bioactive compounds and antioxidant activity of Java cardamom parts (leaves, stems, rhizomes, fruits (pods and seeds)) to explore their bioactivity values. GC-MS analysis was used to identify the bioactive compounds of Java cardamom parts in essential oils. Antioxidant activity was carried out by two methods: DPPH and FRAP. GC-MS analysis of four parts of the Java cardamom obtained 47 compounds as monoterpenes (33), sesquiterpenes (9), hydrocarbons (1), fatty alcohols (1), fatty acids (1), fatty acid esters (1), and diterpenoids (1). 1.8-Cineol is the most dominant secondary metabolite and is found in every part of Java cardamom essential oil, with the highest content produced in Java cardamom steam essential oil (50.78%), followed by Java cardamom fruits essential oil (45.59%). Furthermore, the activity of DPPH and FRAP ranged from 19.07 (leaves) – 27.38 (stems) and 93.43 (stems) – 115.99 (fruits) mol TEAC/g FW. The maximum antioxidant activity is produced in Java cardamom fruit essential oil. Thus, it can be used as a source of producing metabolites as antioxidants in the pharmaceutical industry.

Composition of Phenolic Compounds in South African Schinus molle L. Berries.

The Schinus molle tree is notoriously invasive in most parts of the world, and yet as a pseudospice, its berries potentially possess some significant health benefits which need to be explored. Therefore, polar metabolome of seed + husks (SH), husks (H), and de-hulled (DH) berries were profiled and quantified by untargeted metabolomics approach using UPLC-QTOF-MS. A total of 13 gallotannins, three phenolic acids, a phenolic acid glucoside, three phenolic acid esters, an organic acid, a gallotannin derivative, and nine flavonoids were detected and quantified. Phenolic acids ranged between 12.2–295.7; 4.9–77; and 89.7–1613.1 mg/kg in SH, DH seeds and H respectively. Flavonoids ranged between 1.8–267.5; 73.4–80.4; and 124–564.3 mg/kg in SH, DH seeds and H respectively. Gallotannins ranged between 1.1–146.6; 14.8–21.8; and 48.1–664.8 mg/kg in SH, DH seeds and H respectively. Feruloyltartaric A, quercetin 3-O-glucuronide, catechin digalloylshikimic acid B as well as digalloyl quinic acid were some of the dominant secondary metabolites revealed. These results indicate that S. molle berries are a rich source of secondary metabolites with elevated concentrations in the husks, while DH seeds possess lower concentrations to none. These findings open important insights into the potential of S. molle berries as a natural source of antioxidants for the food and pharmaceutical industries.

Influence of Accelerated Solvent Extraction Conditions on the LC-ESI-MS/MS Polyphenolic Profile, Triterpenoid Content, and Antioxidant and Anti-lipoxygenase Activity of Rhododendron luteum Sweet Leaves.

Evaluation of native plant resources and their efficient use is one of the current trends in phytochemistry. The main aim of the present study was to investigate the biological activities of different Rhododendron luteum Sweet leaf extracts obtained with the use of accelerated solvent extraction using different solvents and extraction temperatures. All extracts were subjected to bioactivity assays, which revealed considerable anti-lipoxygenase (23.07–90.13% lipoxygenase inhibition) and antiradical potential. All samples exhibited high 2,2-diphenyl-1-picrylhydrazyl (DPPH•) (234.18–621.90 mg Trolox equivalents (TE)/g) and 2,2′-azino-bis-3(ethylbenzthiazoline-6-sulphonic acid) (ABTS•+) (88.79–349.41 mg TE/g) scavenging activity, high antioxidant potential in the Oxygen Radical Absorbance Capacity (ORAC) assay (495.77–1011.59 mg TE/g), and moderate ion chelating (Fe2+) capacity. The chemical profile of each sample was determined using liquid chromatography/electrospray ionization triple quadrupole mass spectrometry (LC-ESI-MS/MS) and spectrophotometric procedures. Twenty-three compounds representing seven polyphenol subclasses were detected and quantified, including some phenolic acids and flavonoids that had not been previously reported for this plant material. It was shown that 5-O-caffeoylquinic acid, protocatechuic acid, catechin, quercetin and its glycosides (hyperoside, isoquercetin, quercitrin), and pentacyclic triterpenes were the dominant secondary metabolites in R. luteum leaves. The antioxidant activity was found to be strongly related to different polyphenol groups and total triterpene content, while the anti-lipoxygenase potential was highly dependent on catechin.

The Gel Soap with Raw Materials of Lerak Fruit (Sapindus rarak DC)

Lerak (sapindus rarak DC) is one of the plants that is often used as a noble metal washer, facial cleanser as a remover for acne and as an insecticide, especially earthworms. In this study the manufacture of soap gel by using Lerak plants. Lerak fruit (Sapindus rarak DC) is one of the natural ingredients that can be used as an alternative in soap raw materials. Lerak fruit (S. rarak) contains several secondary metabolites. The most dominant secondary metabolite is saponin. These saponins act as raw material for making soap. The purpose of this study is the use of natural materials, especially Lerak fruit as raw material for gel soap Tests conducted on soap are foam test, soap quality with experiments on several stains and organoleptic soap tests. The results obtained Lerak fruit can be used as raw materials for soap. The foam test results on the soap found that the soap foaming durability was longer. The results of soap quality testing on several stains namely charcoal stains, soy sauce stains and sauces prove the soap can clean stains well. The organoleptic results get a distinctive aroma, odor, and average of density are 1.01.

EXPLORATION OF ANTIBACTERIAL AND ANTIPROLIFERATIVE SECONDARY METABOLITES FROM MARINE BACILLUS

Antiproliferative secondary metabolites producing bacterial strain AVSC4 isolated from marine sediments was identified as Bacillus flexus based on 16S rRNA gene sequence analysis. Under the strategy of liquid- liquid extraction, the crude extract was obtained showed significant antibacterial activity against different clinical pathogens. 0.5% methionine and 0.4% NaCl act as inducers for maximizing the growth and antibacterial activity of strain at pH 7 and 40°C. Heptadecanoic acid and methyl hexadecanoic acid were identified as major and dominant secondary metabolites by GC-MS analysis and also showed significant antiproliferative activity against HT-29 (Human colorectal adenocarcinoma) and A-549 (Lung Cancer) with IC50 value 93.4 µg/ml and 50.04 µg/ml.

Interacting Environmental Stress Factors Affects Targeted Metabolomic Profiles in Stored Natural Wheat and That Inoculated with F. graminearum.

Changes in environmental stress impact on secondary metabolite (SM) production profiles. Few studies have examined targeted SM production patterns in relation to interacting environmental conditions in stored cereals. The objectives were to examine the effect of water activity (aw; 0.95–0.90) x temperature (10–25 °C) on SM production on naturally contaminated stored wheat and that inoculated with Fusarium graminearum. Samples were analysed using Liquid Chromatography-Tandem Mass Spectrometry (LC-MS/MS) on (a) total number of known SMs, (b) their concentrations and (c) changes under environmental stress. 24 Fusarium metabolites were quantified. Interestingly, statistical differences (ChisSq., p < 0.001) were observed in the number of SMs produced under different sets of interacting environmental conditions. The dominant metabolites in natural stored grain were deoxynivalenol (DON) and nivalenol (NIV) followed by a range of enniatins (A, A1, B, B1), apicidin and DON-3-glucoside at 10 °C. Increasing temperature promoted the biosynthesis of other SMs such as aurofusarin, moniliformin, zearalenone (ZEN) and their derivatives. Natural wheat + F. graminearum inoculation resulted in a significant increase in the number of metabolites produced (ChisSq., p < 0.001). For ZEN and its derivatives, more was produced under cooler storage conditions. Fusarin C was enhanced in contrast to that for the enniatin group. The relative ratios of certain groups of targeted SM changed with environmental stress. Both temperature and aw affected the amounts of metabolites present, especially of DON and ZEN. This study suggests that the dominant SMs produced in stored temperate cereals are the mycotoxins for which legislation exists. However, there are changes in the ratios of key metabolites which could influence the relative contamination with individual compounds. Thus, in the future, under more extreme environmental stresses, different dominant SMs may be formed which could make present legislation out of step with the future contamination which might occur.

Antioxidant Activity of Dominant Plants Species in Obat Pahit from Lingga Malay Ethnic in Riau Archipelago

&lt;p&gt;&lt;em&gt;Obat Pahit&lt;/em&gt; is a potion that has been long commonly consumed by Lingga Malay society for generations as stamina keeper. The most dominant plants found in the packaging of the Obat Pahit were namely &lt;em&gt;Bauhunia semibifida, Cnestis palala&lt;/em&gt; and Penawa Root (3 species). This research aimed to investigate and determine activity of antioxidant contents in &lt;em&gt;Obat Pahit&lt;/em&gt; from five Traditional Medicine Practitioners (TMPs) in the district of Lingga. The tested samples were mashed then being soaked into 2 types of solvent: distilled water and methanol, containing HCl 1%. DPPH method was also used in this research. Quantitatively antioxidant activity test of &lt;em&gt;Obat Pahit&lt;/em&gt; from the five TMPs by using methanol solvent had extremely highest activity compared to the distilled water solvent. The test, using TLC plate by spraying the extract from three dominant plants with 0.1 mM of DPPH solution, produced a pale-yellow spots at a wavelength of 366 nm. On the other hand, the test using HPLC at wavelengths of 230 nm and 280 nm showed the presence of two dominant secondary metabolites contents: flavonoid and phenolic. IC50 (ppm) of &lt;em&gt;Bauhinia semibifida&lt;/em&gt; (6.6247), Penawa Root (5.0124) and &lt;em&gt;Cnestis palala&lt;/em&gt; (5.9968) were much lower than IC50 of mangosteen’s rind (41.7675), vitamin C (6.6612) and Stimuno drug (8.333). This antioxidant analysis has not been reported previously. This proof contributed greatly to uncovering potentially native natural resources as an indigenous Indonesian drug which is expected to decrease dependence on imported drugs especially imunomodulator, antihypertensive, antidiabet etc. This research would be beneficial and excellent manifestation for the development of natural antioxidant-based medicines from traditional knowledge of Indonesia’s local ethnicities.&lt;/p&gt;

Geraniin attenuates naloxone-precipitated morphine withdrawal and morphine-induced tolerance in mice.

Potentially life-threatening and unpleasant side effects associated with some analgesics have fueled the drive for the search for more analgesics with better side effect profiles. Geraniin, the most dominant secondary metabolite in the aqueous extract of the aerial parts of Phyllanthus muellerianus, has been shown to possess antinociceptive properties mediated partly by opioidergic mechanisms. The purpose of this study is to determine whether geraniin exhibits tolerance and if it is able to ameliorate withdrawal signs in naloxone-precipitated morphine withdrawal. After chronic treatment of mice with geraniin orally, the formalin test was used to ascertain whether tolerance will develop to its antinociceptive effects and if there is morphine-induced tolerance cross-generalization with geraniin. The effect of geraniin on naloxone-precipitated morphine withdrawal signs in morphine-dependent mice was also investigated. Geraniin (3-30 mg/kg) did not produce any tolerant effects after chronic administration and there was also no cross-generalization with the tolerant effects of morphine. Geraniin did not induce withdrawal signs but significantly reduced the number of jumps in morphine-dependent mice. Geraniin does not produce any tolerant effects like morphine and also reduced the signs associated with naloxone-precipitated morphine withdrawal in mice.

Extraction and Quantification of Bioactive Tyrian Purple Precursors: A Comparative and Validation Study from the Hypobranchial Gland of a Muricid Dicathais orbita.

Muricidae are marine molluscs known for the production of Tyrian purple and bioactive precursor compounds. A validation study for the extraction and analysis of secondary metabolites found in the hypobranchial gland of the muricid Dicathais orbita is reported, using high performance liquid chromatography–mass spectrometry (HPLC-MS) with diode array detector (DAD). Quantification of the dominant secondary metabolites from D. orbita is described, followed by a comparison of solvent extraction procedures and stability studies. The intra- and inter-day relative standard deviation (RSD) for tyrindoxyl sulphate was 0.46% and 0.17%, respectively. The quantification was linear for standards murexine, 6-bromoisatin, and tyrindoxyl sulphate. The limits of detection were 0.03, 0.004, and 0.07 mg/mL, respectively, and the limits of quantification were 0.09, 0.01, and 0.22 mg/mL, respectively. The results showed that alcoholic solvents were better for extracting choline ester and indoxyl sulphate ultimate precursors, while chloroform was more suitable for the extraction of the intermediate precursors. Multivariate analysis revealed significant differences in extract composition according to the solvent used. Stability testing showed an increase of the oxidative compounds 6-bromoisatin and putative tyrindoxyl S-oxide sulphate in the ethanol extracts while more degradation products were seen in the chloroform extracts after months of cold storage. The validated method was found to be simple, reproducible, precise, and suitable for quantification of the secondary metabolites of muricid molluscs for dye precursor and nutraceutical quality control, as well as applications in marine chemical ecology.

Anti-Nociceptive Effects of Geraniin and an Aqueous Extract of the Aerial Parts of Phyllanthus muellerianus (Kuntze) Exell. in Murine Models of Chemical Nociception

Plants from the genus Phyllanthus like Phyllanthus muellerianus have long been used in folk medicine for several ailments including fevers, toothache, dysmenorrhea, anemia and paralysis. Despite these folkloric uses, there is little scientific data supporting the use of this plant in the management of pain. The purpose of this study is to evaluate the aqueous extract of the aerial parts of Phyllanthus muellerianus and its dominant secondary metabolite, geraniin for potential anti-nociceptive effects. The acetic acid-induced abdominal writhing and formalin–induced nociception tests were used to assess the anti-nociceptive effects of the aqueous extract and geraniin. Morphine and diclofenac were used as standard anti-nociceptive agents. The involvement of opioidergic, adrenergic, muscarinic, adenosinergic, serotonergic and nitric oxide pathways in the anti-nociceptive effects of the extract and geraniin were evaluated by selective antagonism of these pathways. Additionally, the effects of voltage-sensitive Ca2+ channels and ATP-sensitive K+ channels were also assessed by selective blockade with nifedipine and glibenclamide respectively. Oral administration of the aqueous extract (30, 100, 300 mg kg-1) and geraniin (3, 10, 30 mg kg-1) produced significant anti-nociceptive effects in both models of chemical nociception. The anti-nociceptive effects of both the extract and geraniin were not antagonized by L-NAME (10 mg kg-1), yohimbine (3 mg kg-1), atropine (5 mg kg-1), theophylline (5 mg kg-1), ondansetron (0.5 mg kg-1) glibenclamide (8 mg kg-1) or nifedipine (10 mg kg-1). Naloxone (2 mg kg-1), however, reversed the anti-nociceptive effects of only geraniin. In conclusion, the aqueous extract and geraniin obtained from the aerial parts of Phyllanthus muellerianus possess both peripheral and central anti-nociceptive effects in murine models of chemical nociception with the anti-nociceptive action of geraniin involving possibly the opioidergic pathways.

Production of Panduratin A, Cardamomin and Sitosterol Using Cell Cultures of Fingerroot (Boesenbergia pandurata (Roxb.) Schlechter))

Fingerroot (Boesenbergia pandurata (Roxb.) Schlechter) is an important Southeast Asia especially Indonesian’s plant that has many pharmacological activities. This plant contains several secondary metabolites such as flavonoids and their prenylated derivates like panduratin A that can be produced trough tissue culture techniques. This study aimed to produce secondary metabolites mainly flavonoids in the fingerroot cell cultures and explain their biosynthetic relationship. Bud’s meristem of fingerroot were initiated to forming callus and shoot in appropriate medium and also induced to produce rhizomes in in vitro condition. Panduratin A content was determined using HPLC. The dominant secondary metabolites were isolated and characterized using, chemical reagents and spectroscopic methods. Panduratin A can be produced through callus and rhizomes formation of fingerroot. Other two secondary metabolites have been indentified as phytosterol and cardamonin with the content 285.85 ± 8.36 % and 316.35 ± 0.82 % respectively which were higher than the original plant. Panduratin A, phytosterol and cardamonin which are supposed to have pharmacological activities have been produced using cell culture of fingerroot Boesenbergia pandurata (Roxb.) Schlechter with higher level compared to the original plants.

In SilicoStudies on Fungal Metabolite against Skin Cancer Protein (4,5-Diarylisoxazole HSP90 Chaperone)

This work was to find out the dominant secondary metabolites derived from the fungus Trichoderma and to test them against skin cancer protein. The metabolites were extracted in 80% methanol from the fungal biomass of Trichoderma isolated from mangrove sediment. The crude methanol extract was purified and analysed for the secondary metabolites by GC-MS. Three predominant compounds (heptadecanoic acid, 16 methyl-, methyl ester; 9,12-octadecadienoic acid; cis-9-octadecenoic acid) identified in the extracts were screened against the skin cancer protein (Hsp90) by in-silico docking method. Of the compounds, heptadecanoic acid, 16 methyl, methyl ester was the most potent having the docking score of −11.4592 Kcal/mol. This value was better than the standard drug “dyclonine”. This work recommends the heptadecanoic acid, 16 methyl, methyl ester for further in vitro and in vivo studies towards its development as anticancer drug.

Closing the Wound

PLANT BIOLOGY In the normal cut and thrust of everyday life, nonfatal injuries are common, and organisms rely on rapid repair mechanisms to stanch the loss of fluids. Adolph et al. have studied the invasive tropical green alga Caulerpa taxifolia , which lives as single polyploid multinucleated cells. In the early 1980s, Caulerpa invaded the Mediterranean, and its mechanism of wound repair may have contributed to its high growth rates. When the algal cells are mechanically broken, a gelatinous material consisting of cross-linked proteins rapidly plugs the wound and results in two cells, each with a full genomic inheritance. Polymer formation depends on the enzymatic unmasking of caulerpenyne, the dominant secondary metabolite of the alga. Its 1,4-bis-enoylacetate moiety is transformed into a dialdehyde, which reacts with nucleophilic groups of algal proteins, forming a life-saving plug. — SMH Angew. Chem. Int. Ed. 44 , 10.1002/anie.200462276 (2005).

Rosa rugosa Thunb. ex Murray

Rosaceae, Rosoideae, Rosa L.; subgenus Eurosa Focke; section Cinnamomeae (DC.) Rehder. Japanese Rose. Rhizomatous multi-stemmed erect deciduous shrub, strongly suckering, mature clones forming impenetrable thickets. Rhizomes woody, with orange-brown cortex and triangulate scale leaves. Rhizome branches and suckers emerge from axillary buds subtended by scale leaves. In addition, suckers may arise from buds on the roots. Stems erect, sometimes arching, to 1.5( − 2) m, often much branched, tomentose when young, densely prickly. Cortex light yellowish brown. Prickles subulate, slender and straight, of all sizes down to acicles. Larger prickles tomentose, at least near the base, and usually glabrous in the apical part. Leaves alternate with (5–)7–9 leaflets contiguous on the rachis. Leaflets nearly equally sized, 2–5 × 1.5–3 cm, leathery and robust, widely elliptical, acute, with broadly cuneate or rounded base. Adaxial side dark green, conspicuously bullate or rugose, rather shiny. Abaxial side green-grey, tomentose to pubescent, with sessile pale glands, and with reticulate nervation. Leaf margin bluntly and simply crenate-serrate, involute, edge of teeth often deflexed. Petiole and rachis densely pubescent, and with many unequal subulate prickles. Stipules pale green, densely pubescent, 2.5 × 1–1.5 cm, divergent, the free part broadly ovate or deltoid. Flowers usually solitary or few together, 6–9 cm across, fragrant, nectarless. Sepals 2–3 cm, entire, with a broad, expanded tip, appressedly pubescent, aciculate and glandular (sometimes with stipitate glands), erect on the hip, persistent. Petals five, bright purplish-pink, sometimes white ( R. rugosa f. alba (Ware) Rehder). Stamens 200– 250 per flower, and styles often more than hundred. Styles pilose; stigmas in a large, domed head, sunk in the narrow, concave disc; disc 2.5–4 mm across; orifice large, at least half the diameter of the disc. A hypanthium (hip) encloses the achenes. It is depressed globose, 1.5–2 cm long and 2–2.5 cm wide, with a distinct neck below the sepals, dull green to orange when unripe, becoming glossy and brilliant red when ripe, most often smooth. Pedicel of the same length as the hip, tomentose, often with gland-tipped acicles, erect in flower, curved in fruit so that the hip points downwards. Achenes with a woody-bony pericarp enclosing the seed. Achenes broadly ovoid, obtusely angular, 4.0–6.0 mm long and 2.0–2.6 mm wide and 1.8–2.2 mm thick, with a distinct suture on both ventral and dorsal sides, hilum basal. Achene surface more or less lustrous, orange-brown. Mean seed (achene) mass is 6.6 mg. The albumen is oily. No subspecies of R. rugosa have been recognized in the British Isles. Despite the many cultivated varieties of the species, mainly forms close to the wild type are seen naturalized. However, naturalized clones may be confused with R. × hollandica (syn. R. × kamtchatica ). This taxon differs morphologically from R. rugosa by having soft-textured, dull leaflets, without prominent veins, less prickly stems, conspicuously glandular sepals, and smaller flowers and hips (Rutherford 1990). Taxonomic position: Rosa L., subgenus Eurosa Focke (syn. subgen. Rosa ), section Cinnamomeae (DC) Rehder (syn. sect. Rosa ; sect. Cassiorhodon Dumort.). Section Cinnamomeae is central in the subgenus Eurosa , which contains all but four of the approximately 150 Rosa species in the world. The diploid species of this section, including R. rugosa , are probably basal in the reticulate evolutionary series from diploid species to irregular polyploid species within this genus (Erlanson 1938; Grossi et al . 1998). Originally introduced as a garden and landscape ornamental, and widely used as rootstock for other cultivated roses, R. rugosa can be found in many different cultivated settings. Now a well-established naturalized alien occurring scattered throughout Britain and invasive in fixed dunes and other coastal habitats.

Tolerance of Marine Invertebrate Herbivores to Brown Algal Phlorotannins in Temperate Australasia

Estes and Steinberg hypothesized that the intensity of sublittoral marine plant—herbivore interactions among different temperate regions has differed over the past 5—10 million yr, due to differences in the influence of diving mammals that prey on marine herbivores. They argued that because diving predators have not occurred in temperate Australasia, densities of sublittoral herbivores have been historically higher there than in comparable North American systems. This has resulted in marine algae and herbivores in temperate Australasia having strong selective effects on each other. Estes and Steinberg predicted that one result of these strong interactions would be that invertebrate herbivores in temperate Australasia should have evolved greater tolerance to brown algal phlorotannins (polyphenolic compounds that are the dominant secondary metabolites in temperate brown seaweeds) than similar herbivores in North America. We tested this prediction for five invertebrate herbivores in temperate Australasia. Most work was done on three herbivores from New South Wales, Australia, the sea urchins (echinoids) Tripneustes gratilla and Centrostephanus rodgersii, and the gastropod (snail) Turbo undulata. Additional experiments were done using Evechinus chloroticus (urchin) and Cookia sulcata (gastropod) from New Zealand. Both the short—term effects of phlorotannins on feeding behavior, and the longer term effects of phlorotannins on the growth or mortality of herbivores were assessed by (a) feeding the herbivores an array of algal species that varied in their phenolic content, and (b) extracting mixed fractions of phlorotannins from the algae and using these extracts to experimentally manipulate the phlorotannin content of palatable agar disks. The phenolic content of algae used in feeding experiments in Australia was sampled seasonally for 3 yr, and the algae were divided into two groups. These included a phenolic—rich group of five species with a mean phenolic content = 7.02% dry mass (range of species means 6.6—7.2%), and a phenolic—poor group of four species with a mean of 2.69% (range of means = 2.2—3.1%). In strong contrast to earlier results from North America, no Australian herbivore consistently preferred phenolic—poor species over those rich in phenolics. Algal phenolic levels also were not correlated with feeding preferences of the New Zealand herbivores. The Australian herbivores were generally not deterred by the addition of extracted phlorotannins to agar disks at concentrations of 5 mg/mL (13.5% dry mass) in the disks. However, some extracts deterred some herbivores, indicating that the effects of phlorotannins on the herbivores are variable. The effects of phlorotannins at higher concentrations (8 mg/mL or 18.5% dry mass) were equivocal. Deterrence was increased in some instances, but elevated concentrations of phlorotannins from Carpophyllum maschalocarpum enhanced feeding by Tripneustes gratilla. Algal phenolic levels were not correlated with the growth of juvenile Tripneustes gratilla raised on a variety of algal diets for 7 mo in the field. Conversion efficiencies of algal biomass to urchin biomass by these echinoids also did not covary with algal phenolic content. Growth of T. gratilla on agar diets for 7 mo was not affected by the addition of phlorotannins extracted from Sargassum vestitum to the agar at a concentration of 5 mg/mL. Growth of the gastropod Turbo undulata over 9.5 mo on selected algal diets was fastest for one measure growth for snails fed a diet of the phenolic—poor Sargassum linearifolium, but algal phenolic levels were not correlated with growth of T. undulata for two other measures of growth. Moreover, conversion efficiencies of Turbo undulata did not vary with diet, indicating that any differences in growth among different diets were due to differences in consumption rather than some physiological effect. This last conclusion was supported in an experiment where T. undulata was grown on agar diets. Growth of the snails was not affected by the addition of phlorotannins from Sargassum vestitum or Ecklonia radiata to agar diets, and in this experiment the amount of different agar diets consumed did not differ. These results do not support proposals that algal phlorotannins function as generally effective "digestibility reducers" against marine invertebrate herbivores. The pattern of geographical variation in the production of phenolics by brown algae, and the responses of marine herbivores to these compounds, are also not easily explained by current theoretical models such as those based on plant apparency or resource availability. A number of the algae studied here also contained smaller nonpolar secondary metabolites such as terpenes or lactones. In general, these algae were the least palatable to the herbivores, and the herbivores grew most slowly when fed monospecific diets of algae rich in nonpolar secondary compounds. The one nonpolar compound that was tested experimentally, the terpine geranylacetone extracted from Cystophora moniliformis, significantly deterred feeding by Tripneustes gratilla. We suggest that nonpolar compounds will generally have stronger effects against Australasian herbivores than do phlorotannins.