Sesquiterpene lactones from Smyrnium cordifolium

In addition to previously obtained furanosesquiterpenes, two new eudesmanolides and a new glechomanolide were isolated from the fruits of Smyrnium cordifolium, while the roots gave two new eudesmanolides. The new compounds from the fruits were 1β-acetoxy-eudesman-4(15), 7(11)-dien-8,12-olide, 1β-acetoxy-8β-hydroxy-eudesman-4(15),7(11)-dien-8,12-olide, 1β,10α;4α,5β-diepoxy-8-hydroxy-glechomanolide, those obtained from the roots were smyrnicordiolide and the corresponding 8β-hydroxy derivative belonging to a new type of oxepine derivative.     

Glechomanolides and eudesmanolides from Smyrnium perfoliatum

In addition to five known sesquiterpenoids, six new compounds were isolated from Smyrnium perfoliatum. The new compounds were 1β-acetoxy-eudesma-3,7(11),8-trien-8,12-olide, 1β-acetoxyeudesma-4(15),7(11),8-trien-8,12-olide, 1β-10α;4α,5β-diepoxy-8β-isobutoxy-glechomanolide, 1β, 10α;4α,5β-diepoxy-8α-isobutoxy-glechomanolide, 1β,4α-dihydroxy-2α,3α-epoxy-eudesma-7(11),8-dien-8,12-olide, 1β,4α-dihydroxy-2α,3α-epoxy-8β-methoxy-eudesma-7(11)-en-8α,12-olide.     

Three new triterpenes from the lichen Xanthoria resendei

The three new migrated hopene type triterpenes 12α-acetoxy-3β-hydroxyfern-9(11)-ene, 3β,12α-dihydroxyfern-9(11)-ene and 3,12-diketofern-9(11)-ene have been isolated from the ether extracts of the lichen Xanthoria resendei, together with peroxyergosterol and the anthraquinone pigments physcion, fallacinal and fallacinol.     

Saturated mono-unsaturated long-chain hydrocarbon profiles of sweet oranges

Three varieties of midseason oranges, viz. Jaffa, Homosassa and Queen, were examined for their saturated and mono-unsaturated hydrocarbon composition in juice sacs. Hydrocarbons were isolated by lipid extraction of the juice sac powders followed by column, thin-layer and AgNO₃-TLC. After hydrogenation, the mono-unsaturated fraction and the saturated fraction were analyzed by GC. In the saturated fraction, the dominant linear hydrocarbon was C₂₃ while C₂₅ predominated in the monoene fraction. iso- And anteiso-branched hydrocarbons comprised between 53 and 63 % of the saturated fraction and only 20–26 % of the monoene fraction. Queen differed from Homosassa and Jaffa in the accumulation of higher percentages of saturated iso- and anteiso-branched hydrocarbons and conversely, showed lower percentages for these branched structures in the monoene fraction. Based on the total relative percentages of the three isomeric hydrocarbons, Homosassa could not be differentiated from Jaffa. The overall profiles for these two oranges, however. showed noticeable differences.     

Two new eudesmane sesquiterpenoids from Daucus carota L.

Two new eudesmane sesquiterpenoids were isolated from the fruits of Daucus carota L. The structures were established based on the interpretation of high-resolution MS and 1D- and 2D-NMR data, the absolute configuration of compound 1 was determined by single-crystal X-ray diffraction. The new compounds were elucidated as (1βH, 3βH, 5βH, 7αH)-4α, 10α-dimethyl-7β-isopropyl-1α, 3α, 4β, 11-tetrahydroxy decahydronaphthalene (1) and (1βH, 3βH, 5βH, 7αH)-4α, 10α-dimethyl-7β-isopropyl-1α, 3α, 4β-trihydroxy decahydronaphthalene-11-O-β-d-glucopyranoside (2). The compound 1 showed significant antioxidant activity.     

Structural analysis of trisialylated biantennary glycans isolated from mouse serum transferrin: Characterization of the sequence Neu5Gc(α2-3)Gal(β1-3)[Neu5Gc(α2-6)]GlcNAc(β1-2)Man

Five variants of mouse serum transferrin (mTf, designated mTf-I to mTf-V) with respect to carbohydrate composition have been isolated by DEAE-cellulose chromatography in the following relative percentages: mTf-I: 0.55; mTf-II: 0.79; mTf-III: 71.80; mTf-VI: 21.90 and mTf-V: 4.96. The primary structures of the major glycans from mTf-III and mTf-IV were determined by methylation analysis and ¹H-nuclear magnetic resonance (NMR) spectroscopy. All glycans possessed a common trimannosyl-N,N′-diacetylchitobiose core. From the glycovariant mTf-III two isomers of a conventional biantennary N-acetyllactosamine type were isolated, in which two N-glycolylneuraminic acid (Neu5Gc) residues are linked to galactose either by a (α2-6) or (α2-3) linkage. A subpopulation of this glycovariant contains a fucose residue (α1-6)-linked to GlcNAc-1. The structure of the major glycan found in variant mTf-IV contained an additional Neu5Gc and possessed the following new type of linkage: Neu5Gc(α2-3)Gal(β1-3)[Neu5Gc(α2-6)]GlcNAc(β1-2)Man(α1-3). In addition to this glycan, a minor compound contained the same antennae linked to Man(α1-6). In fraction mTf-V, which was found to be very heterogeneous by ¹H NMR analysis, carbohydrate composition and methylation analysis suggested the presence of tri′-antennary glycans sialylated by Neu5Gc α-2,6- and α-2,3-linked to the terminal galactose residues. In summary, mTf glycans differed from those of other analyzed mammalian transferrins by the presence of Neu5Gc and by a Neu5Gc(α2-6)GlcNAc linkage in trisialylated biantennary structures, reflecting in mouse liver, a high activity of CMP-Neu5Ac hydroxylase and (α2-6)GlcNAc sialyltransferase.     

Hypochaerin: a new sesquiterpene lactone from Hypochaeris setosus

Hypochaeris setosus contains desacetoxymatricarin, achillin, 1-hydroxy-6β,7α,11β-H-eudesm-4-en-6,12 olide, jacquinelin and hypochaerin, a new guaianolide, established as 3-oxo-4β,5α,6β,7α,11β-H-guai-1(2)-en-6,12 olide.     

The Antennal Sensilla of Oxelytrum erythrurum (Blanchard) and Oxelytrum apicale (Brullé) (Coleoptera: Silphidae)

The typology and placement of antennal sensilla of the carrion beetles Oxelytrum erythrurum (Blanchard) and Oxelytrum apicalis (Brullé) (Coleoptera: Silphidae) were studied using scanning electron microscopy. Two types of sensilla chaetica, two types of sensilla trichodea, four types of sensilla basiconica, one type of sensilla coeloconica, and an unidentified type of sensillum were found in both species. Sensilla chaetica type 1 are found on the antennomeres proximal to antennal club (A1?CA8); chaetica type 2 are found on the club (A9?CA11). Sensilla trichodea are found on A9?CA11; one type (T1) is found on the proximal portion of the club, the other type (T2) on the apical portion. Basiconica type 1 are found on the dorsal surface of A9?CA11; they are much denser on the apical portion of the antennal club than on the proximal. In O. erythrurum, a nocturnal species of the Chaco-Pampean plain, T2 two are found on A10 and A11. In Oxelytrum apicale, a mountain species, probably diurnal, only A11 bears T2, but they are denser than in the other species. It is suggested that O. apicale depends more on contact chemoreception than O. erythrurum. The ventral surface of the antennal clubs shows no remarkable difference between species.     

Terpenoids from seeds of Abies firma

Nine monoterpenoids, 16 sesquiterpenoids including two novel compounds, 12 diterpenoids and sitosterol were identified in seeds of Abies firma. Two new selinane-type compounds were isolated and their structures were determined as 4α-methoxy-selina-11-ene and 11-hydroxy-4α-methoxy-selinane on the basis of chemical and spectroscopic evidence.     

Saturated and mono-unsaturated long-chain hydrocarbon profiles from Citrus unshiu juice sacs

Six cultivars of satsuma mandarin—Kawano Wase, Owari, Silverhill, Foley, Sugiyama and Nobilis—were examined for content of saturated and mono-unsaturated long-chain hydrocarbons in their juice sacs. Linear hydrocarbons accounted for more than 53% of the saturates and more than 87% of the monoenes. In the saturated fraction the major linear hydrocarbon was C₂₅ while in the monoene fraction C₂₅ and C₂₉ predominated. The ratios of linear/iso C₂₃ and C₂₅ saturates were greater than in other citrus previously investigated. Kawano Wase had profiles quite different from the other cultivars. Foley and Owari can be differentiated from the other cultivars by their linear monoene profiles. Long-chain hydrocarbon profiles intrinsic to the mandarin species, C. unshiu, were compared with profiles of non-mandarin species.     

Diterpenes from Stevia monardaefolia

An investigation of Stevia monardaefolia resulted in the isolation of two new labdane type diterpenes, 6α-angeloyloxy nidorellol and 6α-angeloy     

Saturated and mono-unsaturated long-chain hydrocarbon profiles from mandarin juice sacs

The long-chain saturated and mono-unsaturated hydrocarbon content of the juice sacs of five mandarin cultivars (Mediterranean, Honey, Wilking, Kinnow, King) were examined. Normal homologues accounted for more than 47% of the saturated and more than 75% of the monoene hydrocarbons. In the saturated fraction the major hydrocarbon was n-C₂₅ but in the monoene fraction n-C₂₅ predominated in Kinnow and King while C₂₉ predominated in Mediterranean, Honey and Wilking. All five cultivars could be differentiated from each other and from other citrus species by their hydrocarbon patterns. The noticeably high normal/iso ratios of saturated C₂₃ and C₂₅ hydrocarbons previously shown to be characteristic of mandarin species, Citrus unshiu and C. reticulata, were also found in C. nobilis and C. deliciosa.     

Sesquiterpene lactones of Podanthus mitiqui

Ovatifolin and two new sesquiterpene lactones, deacetylovatifolin and arturin (1β-hydroxy-8β-angeloyloxy-eudesmane-4(15),11(13)-diene-6α,12-olide, have been isolated from stems and leaves of Podanthus mitiqui. Two of these compounds showed cytotoxic activity.     

A pregnane ester triglycoside from Sarcostemma brevistigma

A new pregnane ester glycoside, brevine, was isolated from the dried twigs of Sarcostemma brevistigma. Its chemical and spectroscopic properties were consistent with the structure 11-O-benzoyl-sarcogenin-3-O-α-L-diginopyranosyl (1 → 4)-O-α-L-diginopyranosyl(1 → 4)-O-α-L-diginopyranoside.     

Sesquiterpene lactones,flavonoids and anthraquinones from Asphodeline globifera and Asphodeline Damascena

The known compounds chrysoeriol, apigenin, luteolin, acacetin, scutellarein, 6-methoxyluteolin, apigenin 7-glucoside, luteolin 7-glucoside, esculetin, chrysophanol, asphodeline, mircocarpin, sitosterol, 1-β-acetoxyeudesman-4(15),7(11)dien-2α,12-olide and 1-β-acetoxy-8β-hydroxyeudesman-4(15),7(11)-dien-8α,12-olide were isolated from Asphodeline globifera and A. damascena. A new sesquiterpene lactone 1-β-acetoxy-8β-ethoxyeudesman-4(15),7(11)dien-8α, 12-olide was also characterized. These are the first reports of sesquiterpene lactones in Asphodeline and in the Liliaceae.     

Triterpenes from Maytenus horrida

The new triterpene 1β,3β,11α-trihydroxyolean-12-ene and the already known compounds, lupeol, germanicol, 3β-hydroxy-glutin-5-ene, β-amyrin, 3β-hydroxyolean-9(11),12-diene, 3-oxo-olean-9(11),12-diene, 3β,11α-dihydroxyolean-18-ene,3β,11α-dihydroxyolean-12-ene, 3β,29-dihydroxy-glutin-5-ene and dulcitol, were isolated from the root bark of Maytenus horrida.     

Callus-mediated organogenesis and effect of growth regulators on production of different valepotriates in Indian valerian (Valeriana jatamansi Jones.)

A reproducible and efficient callus-mediated shoot regeneration system was developed for the large-scale production of Valeriana jatamansi Jones., a highly medicinal plant species of global pharmaceutical importance. Effect of Murashige and Skoog (MS) medium supplemented with different concentrations of 2,4-dichlorophenoxyacetic acid (2,4-D), α-naphthaleneacetic acid (NAA) and indole-3-butyric acid (IBA) on callus induction and production of valepotriates accumulation was studied by using different explants. In V. jatamansi, the degree of callus induction varied significantly depending on explants type and the growth regulators used. Among different explants used, rhizomes have the highest callus induction potential followed by leaf. The callus induction frequency was found to be optimum in rhizome explants on media supplemented with 0.5 mg/l 2,4-D. The regenerative ability of proliferated compact calli was studied by the application of cytokinins alone and in combination with auxin. MS medium fortified with 0.75 mg/l thidiazuron in combination with 0.5 mg/l NAA showed the highest regeneration frequency (88.6 %) and produced the maximum number of shoot buds (15.20 ± 0.20) capable of growing into single plants. Vigorous callus obtained from MS medium supplemented with different concentrations of 2,4-D, NAA and IBA were used for industrially important valepotriates [acevaltrate (ACE), valtrate (VAL) and didrovaltrate (DID)] analysis. High performance liquid chromatography analysis of callus revealed that medium with 2,4-D (1 mg/l) was found responsible for increasing ACE and DID yield, whereas VAL production was higher in case of medium supplemented with NAA (1 mg/l). However, the accumulation of valepotriates in callus decreased in logarithmic phase after 8 weeks. IBA was not beneficial for the valepotriate synthesis, as it helped to accumulate significantly lower concentration of ACE, VAL and DID. Micropropagated plantlets with well-developed root system were successfully acclimatized in greenhouse condition, in root trainers containing garden soil with a survival frequency of 100 %. As Indian valerian is a highly traded medicinal plant due to extensive use of its industrially important secondary metabolites, the present system can be utilized to obtain mass multiplication of the species as well as for the stable biomass and continuous valepotriate production for the pharmaceutical industries.     

Diterpenoids from Acacia leucophloea

From the root bark of Acacia leucophloea (Mimosaceae) two new pimar-8(14)-ene diterpenoids have been isolated. Their structures have been established by chemical and spectroscopic means as 1β,15R,16-trihydroxypimar8(14)-ene(leucophleol) and 15R,16-epoxy-1β,11α-dihydroxypimar-8(14)-ene(leucophleoxol).     

Pyrophosphate: fructose-6-phosphate 1-phosphotransferase is involved in the tolerance of Arabidopsis seedlings to salt and osmotic stresses

In plants, pyrophosphate: fructose-6-phosphate 1-phosphotransferase (PFP) is a regulatory enzyme that participates in glycolysis and gluconeogenesis. Arabidopsis contains two PFPα subunit genes (PFPα1 and PFPα2) and two PFPβ subunit genes (PFPβ1 and PFPβ2). The single-knockout mutants of the PFP subunit genes were isolated, and double and quadruple pfp mutants were generated by crossing the single mutants. To elucidate the role of PFP in stress tolerance, the responses of the double and quadruple pfp knockout mutants to stress conditions, including osmotic and salt stresses, were examined. The seedling growth of the pfpα1/α2 and pfpβ1/β2 double mutants and the pfpα1/α2/β1/β2 quadruple mutant was severely retarded under salt and osmotic stress conditions compared with that of the wild type. The expression of PFP subunit genes increased in response to salt and osmotic stresses. In contrast, the vegetative growth of the wild type and pfp mutants after the seedling stage was similarly affected by salt and osmotic stresses. These findings suggest that PFP plays a role in the adaptation of Arabidopsis seedlings to salt and osmotic stresses.