No full-text available
To read the full-text of this research,
you can request a copy directly from the authors.
Isolation of free cis and trans-phytol from the red alga Gracilaria andersoniana
... In H. verticillata also, the E-isomer is predicted by the library check. Both Z and the E phytols have been isolated as unbounded molecules from the red algae, Gracilaria andersonia (19). The current study founded more lipids compounds in H. verticillata than Byju et al , (20) study that recorded fifteen compounds while Pandi and Rajkumar(4) found six compounds. ...
... From our preliminary studies, N. oculata was selected since its ethyl acetate extract showed interesting antimicrobial activity against E. faecalis (MIC 128 μg/mL), S. aureus (MIC 256 μg/mL), B. cereus (MIC 256 μg/mL), and P. aeruginosa (MIC 256 μg/mL), and significant cytotoxic activity against MCF7, HepG2, SK-LU-1, and KB with IC 50 values of 41.93 ± 4.51 to 65.08 ± 3.19 μg/mL. This is the first report on the chemical investigation and biological activity of N. oculata, which led to the isolation and identification, based on MS and NMR data and comparison with literature, of the compounds as (22E,24R)-ergosta-7,9,22-trien-3β-ol (1) [10], (22E,24R)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (2) [11], (22E,24R)-ergosta-7,22-dien-3β,5α,6β-triol (3) [12], phytol (4) [13], palmitic acid (5) [14], stearic acid (6) [14], and linoleic acid (7) [15]. ...
From our preliminary studies, N. oculata was selected since its ethyl acetate extract showed interesting antimicrobial
activity against E. faecalis (MIC 128 μg/mL), S. aureus (MIC 256 μg/mL), B. cereus (MIC 256 μg/mL), and P. aeruginosa
(MIC 256 μg/mL), and significant cytotoxic activity against MCF7, HepG2, SK-LU-1, and KB with IC50 values of 41.93 ± 4.51
to 65.08 ± 3.19 μg/mL. This is the first report on the chemical investigation and biological activity of N. oculata, which
led to the isolation and identification, based on MS and NMR data and comparison with literature, of the compounds as
(22E,24R)-ergosta-7,9,22-trien-3β-ol (1) [10], (22E,24R)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (2) [11], (22E,24R)-ergosta-
7,22-dien-3β,5α,6β-triol (3) [12], phytol (4) [13], palmitic acid (5) [14], stearic acid (6) [14], and linoleic acid (7) [15].
Compounds 1–3 were tested for antimicrobial activity. Compound 1 shows remarkable activity against E. faecalis,
S. aureus, and the yeast C. albicans with MIC values of 16, 64, and 128 μg/mL, respectively. Compound 3 is active against all
of the tested microorganisms with MIC values of 128–256 μg/mL. Compound 2 shows no activity against any of the tested
microorganisms.
The cytotoxicity of isolated compounds 1–3 was tested against HepG2, MCF7, SK-LU-1, and KB cancer cell lines.
Among these compounds, compound 1 was the most active against all of the tested cancer cell lines with IC50 values in the range
of 22.17 ± 0.73 to 41.59 ± 1.68 μM. Compound 2 exhibits weak activity with IC50 values of 51.93 ± 2.51 to 65.08 ± 1.39 μM.
Compound 3 shows no cytotoxicity against all of the tested cancer cell lines.
... In H. verticillata also, the E-isomer is predicted by the library check. Both Z and the E phytols have been isolated as unbounded molecules from the red algae, Gracilaria andersonia (19). The current study founded more lipids compounds in H. verticillata than Byju et al , (20) study that recorded fifteen compounds while Pandi and Rajkumar(4) found six compounds. ...
Hydrilla verticillata (Linn.F.) considered as an invasive species in Iraq. Our study aimed to identified the concentration of lipid compounds in that plant whicht collected from Euphrates River/ Kufa-Iraq. Twenty-three compounds were identified. The most prevailing compounds were Hexadecanoic acid, methyl ester (26.26%), 9,12-Octadecadienoic acid (Z,Z)-, methyl ester (19.07%) and phytol (11.83%) as major components, and their structures were elucidated. In present study, we concluded that this species (H. verticillata) is a good source of many fatty acids especially octadecadienoic acid and phytol, and we suggested to create new studies deals with using this plant in pharmaceutical products.
... 3-Hydroxyolean-12-en-1-one (7). Colorless 13 [19]. ...
... 13 C NMR (150 MHz, MeOD) δ C -183.5 (C-8), 171.7 (C-6), 113.2 (C-7), 87.1 (C-5), 66.7 (C-3), 47.8 (C-2), 46.6 (C-4), 36.6 (C-1), 29.9 (C-11), 27.4 (C-9), and 26.8 (C-12). The structure of subfraction F A432 were identified as shown and named isololiolide (7) by comparison of their physical and spectral data (1H-NMR, 13C-NMR, MS) with reported values (Peng and Yu 1993) (Fig. 4) 12H, s, H-19, 19′, 20, 20′) The data are essentially consistent with the reported literature of zeaxanthin (James and John 1976); therefore, the structure of subfraction F A441 was assigned as shown and named zeaxanthin (8) (Fig. 4). Fig. 4 Structure of ten compounds isolated from Ulva prolifera essentially consistent with the reported literature of cholest-5en-3-ol (Wison et al. 1996); therefore, the structure of subfraction F A442 was established as shown and named cholest-5-en-3-ol (9) (Fig. 4). ...
Ten compounds (1~10) were successfully isolated from green algae Ulva prolifera through the combination of silica gel column chromatography, Sephadex LH-20 column chromatography and repeated preparative thin-layer chromatography. These ten compounds showed antialgal activity against red tide microalgae. Among them, compounds 3, 6, and 7 showed stronger antialgal activity against red tide microalgae. Furthermore, their structure was identified on the basis of spectroscopic data. There are three glycoglycerolipids: 1-O-octadecanoic acid-3-O-β-D-galactopyranosyl glycerol (2), 1-O-palmitoyl-3-O-β-D-galactopyranosyl glycerol (4), and 1-O-palmitoyl-2-O-oleoyl-3-O-β-D-galactopyranosyl glycerol (5); two monoglycerides: glycerol monopalmitate (1), 9-hexadecenoic acid, 2,3-dihydroxypropyl ester (3); two terpenoids: loliolide (6) and lsololiolide (7); one lipid-soluble pigments: zeaxanthin (8); one sterol: cholest-5-en-3-ol (9); and one alkaloid: pyrrolopiperazine-2,5-dione (10). These compounds were isolated from U. prolifera for the first time, and compounds 2, 3, 5, and 8 were isolated from marine macroalgae for the first time.
... compounds included a neolignan (1) and an ellagic acid analog (2). The known compounds included the neolignan, neotaiwanensol B (3) ; two alkenylphenols, sarmentosumols A (4) and B (5) ; 10 amide alkaloids, (2E,4E)-Nisobutylhexadeca-2,4-dienamide (7) (Reisch et al., 1985), (2E,4E)-N-isobutyl-2,4-decadienamide (8) (Yasuda et al., 1981), 1-[7-(1,3benzodioxol-5-yl)-1-oxo-2,4-heptadienyl]piperidine (9) (Araujo-Junior et al., 1997), retrofractamide A (10) (Park et al., 2002), dehydropipernonaline (11) (Shoji et al., 1986), (2E,4E)-N-isobutyl-7-(3,4-methylenedioxyphenyl)hepta-2,4-dienamide (12) , (2E,8E)-N-[9-(3,4-methylenedioxyphenyl)-2,8-nonadienoyl] piperidine (13) (Tabuneng et al., 1983), retrofractamide C (14) (Banerji et al., 1985), piperolein B (15) (Tabuneng et al., 1983), and 5,6-dihydropiperlonguminine (16) (Navickiene et al., 2000); a monoterpene, pressafonin A (17) ; a diterpene, trans-phytol (18) (Sims and Pettus, 1976);a steroid, ergosta-4,6,8(14),22-tetraen-3-one (19) (He and Feng, 2000); a quinone, tocopherylquinone (20) (Zhao et al., 2010); a phenylpropanoid, 4allyl-1,2-phenylene diacetate (21) (Villegas et al., 2011); and a phenol derivative, monomethyl olivetol (Mcclanahan and Robertson, 1985) (22). The structures of the known compounds were determined by comparing their spectroscopic data with previously reported data. ...
Two new hydroxychavicol analogs nudibaccatumin A (1) and B (2), together with twenty known compounds were isolated from the methanol extract of Piper nudibaccatum. Their structures were elucidated by extensive spectroscopic analyses (1D and 2D NMR, HRESIMS, UV, IR and polarimetry). Hydroxychavicol is a known inhibitor of xanthine oxidase (XO). In the present study, hydroxychavicol and 5 natural analogs (1–5) were evaluated for their XO inhibitory activity. Neotaiwanensol B (3) (IC50 = 0.28 μM) showed a greater inhibitory effect than hydroxychavicol and allopurinol (the positive control). Two new compounds 1 and 2 showed a moderate inhibition activity with an IC50 value of 62.94 μM and 70.67 μM, respectively.
... (2) (Sims & Pettus Jr., 1976;Goodman et al., 1973), sitostenona (3), sitosterol (4) (Della Greca et al., 1990) e ácido vanílico (5) (Lai et al., 1985) foram identifi cadas através da comparação dos dados espectrais obtidos com os da literatura. Em Polygonaceae, a ocorrência deste ácido está restrita aos gêneros Polygonum (Adinarayanda et al., 1980;Ulubelen et al., 1992;Smorlarz, 2000) e Rumex (Djurdjevic et al., 1992). ...
RESUMO: O estudo químico das frações neutra em hexano das folhas e em diclorometano do caule de Coccoloba mollis resultou no isolamento de um triterpeno pentacíclico (simiarenol), que pela primeira vez ocorre em Polygonaceae, dois fi toesteróides (sitostenona e sitosterol), um diterpeno (trans-fi tol) e de um benzenóide (ácido vanílico) que está sendo descrito pela vez neste gênero. A identifi cação estrutural destes compostos foi feita com base na análise dos dados espectrais (IV, EM e RMN, incluindo DEPT e HMQC), bem como pela comparação com dados descritos na literatura. ABSTRACT: "Chemical constituents from leaves and stem of Coccoloba mollis Casaretto (Polygonaceae)". This work describes the isolation of a pentacyclic triterpene (simiarenol), described for the fi rst time in this family, two phytosteroids (sitostenone and sitosterol), a diterpene (trans-phytol) and a benzenoid (vanillic acid), described for the fi rst time in this genus, from leaves and stem of Coccoloba mollis. These compounds were identifi ed on basis of their spectral data (IR, MS and NMR, including DEPT and HMQC), as well as by comparison with literature data.
... e l s e v i e r . c o m / l o c a t e / p h y t o c h e m (Barrero et al., 1991), 13,15-dihydroxypodocarpa-8,11,13-triene (Georges et al., 2012, 7a-hydroxymanool (Jiang et al., 2001), 8-hydroxy-12-oxo-13-abieten-18-oic acid (Baltenweck-Guyot et al., 2000, trans-phytol (Sims et al., 1976); four sesquiterpenes: 4-[4-hydroxy-6-(hydroxymethyl)-2,6-dimethyl-1-cyclohex-1-en-1-yl] butan-2-one (Miyase et al., 1987), clovane-2b,9a-diol (Heymann et al., 1994), caryolane-1,9b-diol (Heymann et al., 1994), 8,9-dihydroxy-1(12)-caryophllene (Heymann et al., 1994); three lignans: dihydrodehydrodiconiferyl alcohol (Silva et al., 1989), pinoresinol (Abe and Yamauchi, 1988), prinsepiol (Kilidhar et al., 1982); and six other compounds: 4-hydroxy-3-methoxycinnamaldehyde (Kikuzaki et al., 1999), 5,4 0 -dihydroxy-3,7-dimethoxy-6methylflavone (10) , rhododendrol (Kubo et al., 1983), 4-(p-hydroxyphenyl)-2-butanone (Ayer and Singer, 1980), b-sitosterol (Hussain et al., 2008), and stigmastanone (Guerriero et al., 1993). ...
... Ž . reports of extractable cis-Z and trans-E phytol Ž . in a marine red alga Sims and Pettus, 1976 , of Ž phytyl esters in marine dinoflagellates Withers and . Nevenzel, 1977 and of phytol esterified to fatty Ž . ...
... Eleven known compounds were identified as, dehydroroemerine (2), (R)-roemerine (3), nuciferine (4), N-methylasimilobine (5), and anonaine (6) (Guinaudeau, Leboeuf, & Cave, 1975, 10-eicosanol (7), 3,7,11,15-tetramethyl-1-hexadecen-3-ol (isophytol) (8) (Ahmad & Ali, 1991), 3,7,11,15tetramethyl-2-hexadecen-1-ol (trans-phytol) (9) (Sims & Pettus, 1976), 7,11,15-trimethyl-2-hexadecanone (10) (Worner & Schreier, 1991) (Kojima, Sato, Hatano, & Ogura, 1990) and quercetin 3-O-b-Dglucopyranoside (12) (Markham, Ternai, Stanley, Geiger, & Mabry, 1978), by comparison of their spectral data with published values. This is the first report for the spectral data of 7, that was previously prepared synthetically (Churchward, Gibson, Meakins, & Mulley, 1950), and without any reference or spectral evidence isolated from Semiaquilegia adoxoides (Feng et al., 2006). ...
... Stereo-chemically, the (E)-phytol has long been known as the diterpenoid alcohol moiety of chlorophyll in plants (Phelan et al. 1986) and in H. verticillata also, the E-isomer is predicted by the library check. Both Z and the E phytols have been isolated as unbounded molecules from the red algae, Gracilaria andersonia (Sims and Pettus 1976) and certain marine green algae (Anjaneyulu et al. 1991). Phelan et al. (1986) , reported the presence of (E)-phytol as a volatile component in an animal system, as male wing pheromone of Ephestia elutella (Pyralidae). ...
The composition of the lipophilic extract from Hydrilla verticillata, the common aquatic weed collected from Sasthamkotta Lake, the largest freshwater lake in Kerala, south of the west coast of India, was investigated. The lake is a designated wetland of international importance under the Ramsar Convention since 2002. GC-MS study of the unsaponifiable lipophilic extract of H. verticillata confirmed the presence of 3,5,11,15-tetramethyl 1- hexadecen-3-ol (C20H40O) and phytol (C20H40O) as major components, and their structures were elucidated. Phytol and 3,5,11,15-tetramethyl 1- hexadecen3-ol are the two isomers of the diterpeneol (C20H40O) found in the unsaponifible lipophilic extract of H. verticillata and are formed by the hydrolysis of the alcohol moiety of chlorophyll. On quantification, an appreciable concentration of phytol (6.39 g Kg−1) was estimated. The feasibility to utilize H. verticillata to produce phytol is to be addressed by further studies since H. verticillata is considered as one of the world’s fast widely spread aquatic weeds on account of its numerous mechanisms of vegetative reproductions.
... This result is consistent with previous studies since cholesterol and other C-27 sterols are considered the primary sterols of the red algae (Fattorusso et al., 1975;Gibbons et al., 1967;Govindan et al., 1993;Hattab et al., 2006;Moses Babu et al., 1990). Besides, cholesterol has also been found in other species of Gracilaria Srinivas, 1992a, 1992b;Govindan et al., 1993;Henriquez et al., 1972;Sims and Pettus, 1976). ...
The analysis of the total methyl esters of fatty acids from the extracts of Gracilaria birdiae, Gracilaria caudata, Gracilaria cerviconis, Gracilaria domingensis collected in the coast of Paraíba, Northeast Brazil, as well as their chemotaxonomic significance are herein reported for the first time. They can be recognized as a group that represents analogous chemotaxonomic basis since they show common constituents in their composition, such as hexadecanoic acid and cholesterol. Differences found in the fatty acid composition between the studied species reinforce the proposal to transfer G. caudata for the genus Hydropuntia (H. caudata).
... Stereo-chemically, the (E)-phytol has long been known as the diterpenoid alcohol moiety of chlorophyll in plants (Phelan et al. 1986) and in H. verticillata also, the E-isomer is predicted by the library check. Both Z and the E phytols have been isolated as unbounded molecules from the red algae, Gracilaria andersonia (Sims and Pettus 1976) and certain marine green algae (Anjaneyulu et al. 1991). Phelan et al. (1986) , reported the presence of (E)-phytol as a volatile component in an animal system, as male wing pheromone of Ephestia elutella (Pyralidae). ...
... n-Hexane and ethyl acetate extracts from komatsuna and ethyl acetate extract from spinach showed marked inhibitory effects against TCDD-induced activation of AhR. To clarify the compounds inhibitory to AhR activation by TCDD, n-hexane and ethyl acetate extracts of komatsuna (ethyl acetate extract in spinach) were subjected to a combination of chromatographies over silica gel, Toyopearl HW-40 and MCIgel CHP 20P, to give phytol (1), 19) (7), 24) adenosine (8), guanosine (9) and uridine (10) 25) from spinach (Fig. 1). The identification of these compounds was established by comparing the physical and spectral data with literature values or by direct comparisons with authentic specimens. ...
As a part of our study to clarify the interaction of food ingredients with the aryl hydrocarbon receptor (AhR), we studied the interaction of 10 constituents (phytol, p-coumaric acid, 5 flavonol glycosides, adenosine, guanosine and uridine), isolated from aqueous alcohol extracts of spinach and komatsuna, with the AhR by applying the AhR-based bioassay for dioxins, the Ah-Immunoassay and the AhR-dependent luciferase reporter gene assay. Among them, flavonol glycosides and phytol had slight inhibitory effects on AhR activation by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) at high concentrations, however the effects were not comparable with those produced by kaempferol, regarded as one of the main antagonists of AhR. Also, flavonol glycosides showed weak luciferase inductions at high concentrations.
... Eleven known compounds were identified as, dehydroroemerine (2), (R)-roemerine (3), nuciferine (4), N-methylasimilobine (5), and anonaine (6) (Guinaudeau, Leboeuf, & Cave, 1975, 10-eicosanol (7), 3,7,11,15-tetramethyl-1-hexadecen-3-ol (isophytol) (8) (Ahmad & Ali, 1991), 3,7,11,15-tetramethyl-2-hexadecen-1-ol (trans-phytol) (9) (Sims & Pettus, 1976), 7,11,15-trimethyl-2-hexadecanone (10) (Worner & Schreier, 1991), βsitosterol-3-O-β-D-glucopyranoside (11) (Kojima, Sato, Hatano, & Ogura, 1990) and quercetin 3-O-β-D-glucopyranoside (12) (Markham, Ternai, Stanley, Geiger, & Mabry, 1978), by comparison of their spectral data with published values. This is the first report for the spectral data of 7, that was previously prepared synthetically (Churchward, Gibson, Meakins, & Mulley, 1950), and without any reference or spectral evidence isolated from Semiaquilegia adoxoides (Feng et al., 2006). ...
From the leaves of Nelumbo nucifera (an aquatic plant), one new compound, 24(R)-ethylcholest-6-ene-5α-ol-3-O-β-d-glucopyranoside (1), along with 11 known metabolites (2–12), were isolated and identified by spectroscopic methods including 1D- and 2D NMR. Antifungal activity for (R)-roemerine (3) (IC50/MIC = 4.5/10 μg/mL against Candida albicans) and antimalarial activity for (R)-roemerine (3) and N-methylasimilobine (5) (IC50 = 0.2 and 4.8 μg/mL for the D6 clone, respectively, and 0.4 and 4.8 μg/mL for the W2 clone, respectively) was observed. None of the compounds were cytotoxic to Vero cells up to a concentration of 23.8 μg/mL. NMR data for 10-eicosanol (7) and 7,11,15-trimethyl-2-hexadecanone (10) are presented for the first time. An analysis of the structure–activity relationship shows that the substituents in position C-1 and C-2 of aporphine alkaloids are crucial for the antimalarial activity.Graphical abstract24(R)-Ethylcholest-6-ene-5α-ol-3-O-β-d-glucopyranoside (1), along with 11 known compounds (2–12) including aporphine alkaloids, diterpenes, a steroid glycoside and a flavonoid glycoside were isolated from the leaves of Nelumbo nucifera and evaluated for their antifungal, antimalarial and for cytotoxic activities. Antifungal activity was observed for (R)-roemerine (3) and antimalarial activity for (R)-roemerine (3) and N-methylasimilobine (5). Position C-1 and C-2 of aporphine alkaloids is crucial for antimalarial activity.
One undescribed amide, pipermullesine A, two undescribed isoquinoline alkaloids, pipermullesines B and C, and six undescribed dipeptides, pipermullamides A–F, along with 28 known compounds, were isolated from the aerial parts of Piper mullesua. The structures of the undescribed compounds were elucidated based on the analysis of 1D and 2D NMR and MS data. Furthermore, the structures of pipermullesines A–C were confirmed by single crystal X-ray diffraction analysis. All isolates were evaluated for inhibitory activity against platelet aggregation induced by thrombin (IIa) or platelet-activating factor (PAF). (-)-Mangochinine, pellitorine, and (2E,4E)-N-isobutyl-2,4-dodecadienamide showed weak inhibitory activity against rabbit platelet aggregation induced by PAF, with IC50 values of 470.3 µg/mL, 614.9 µg/mL, and 579.7 µg/mL, respectively.
Graphical Abstract
Open image in new window
Ces travaux de thèse décrivent l’hémisynthèse de dérivés de l’acide grandiflorénique (AG). Ce produit naturel a dans un premier temps été converti en ent-kaur-9(11),16-dien-19-ol, composé qui a ensuite été estérifié dans les conditions de Steglich par une série d’acides benzoïques diversement substitués. Aux douze nouveaux composés ainsi obtenus a été ajoutée la synthèse du 9(11),16-dien-19-(2- méthyl-5-nitro-1H-imidazol-1-yl)éthyl-ent-kaurène. Ces dérivés de l’AG ont été soigneusement purifiés, puis complètement caractérisés (IR, SM, RMN 1D et 2D) en vue de leur évaluation biologique. L’activité antibactérienne a été testée sur différentes souches bactériennes comme Staphylococcus aureus, Enterococcus faecalis, Klebsiella pneumoniae, Pseudomonas aeruginosa et Escherichia coli. Les propriétés fongicides ont été évaluées sur Candida albicans et C. krusei. L’activité anti-inflammatoire in vivo a été étudiée sur des souris BIO:NMRI en utilisant le test de l’oedème de l’oreille induit par le xylol. Les dérivés d’acide grandiflorénique n’ont malheureusement montré aucune activité antibactérienne, ni antifongique, mais leur activité anti-inflammatoire s’est montrée prometteuse dans le cas de l’inflammation aiguë, le 9(11),16-dien-18-[2-(4-isobutylphényl)propyl]-ent-kaurène se révélant être le meilleur composé.
The possibility for mass production of phytol, inhibitory diterpene against ACAT (Acyl-CoA: Cholesterol acyltransferase) was investigated by using callus culture of lettuce. The callus were induced from lettuce cotyledon explants on MS medium containing 0.5 mg.L^{-1} NAA after 4 week`s culture. Adventitious roots were formed from the explants on MS medium containing 0.5 mg.L^{-1} IBA or 1.0 mg.L^{-1} NAA. Adventitious shoots and roots were emerged from the callus when the callus was transferred to MS medium containing auxin alone, or with cytokinin. The plant growth regulators and their concentrations for the organogenesis were 1.0 mg.L^{-1} NAA, 0.1 mg.L^{-1} BA, 0.5 mg.L^{-1} NAA with 0.1 mg.L^{-1} kinetin, or 0.5 g.L^{-1} 2.4-D with 1.0 mg.L^{-1} kinetin. Analyses of chlorophyll contents showed that chlorophyll contents were higher in morphogenic calli than in non-morphogenic calli. However, the chemical analyses of gas chromatography indicated that phytol contents were not proportionate to the chlorophyll contents of callus. The content of phytol was higher in callus than in lettuce cotyledon.ledon.
Chemical examination of aerial parts of the plant, Lagascea mollis has resulted in the isolation of two compounds, an acyclic diteipene alcohol which has been identified as (£)-phytol 1 and lauric amide 3. Their structures have been elucidated by spectral data and chemical transformations. This is the first report of isolation of both these compounds from this plant. It is noteworthy that compound 1 has been found to be a potent antimycobacterial agent and thus, L. mollis could be exploited as an alternative source.
The phytochemical investigation of Coussarea platyphylla led to the isolation of triterpenes betulonic and betulinic acid, monoterpenes monotropein and monotropein salt, the diterpene trans-phytol and esteroids. The structures of the isolated compounds were assigned on the basis of spectroscopic data, including two-dimensional NMR methods. The antiproliferative properties against human cancer cell lines and molluscicidal activity against Biomphalaria glabrata of the crude methanolic extract and of its fractions were investigated.
This review gives in depth coverage of natural products derived from West African medicinal plants with diverse biological activities. Unique compound classes from West African flora having remarkable biological activities have been highlighted, as well as a correlation between biological activities of the derived compounds and the uses of the plants in African traditional medicine and their chemotaxonomic classifications have also been included in the discussion. In the first part of the review, the focus is on alkaloids and flavonoids.
Three new polyacetylenes, 8 - (Z) - decene - 4, 6-diyne - 1, 3, 10-triol (1), 1, 3S, 8S - trihydroxydec - 9 - en - 4, 6 - yne (2), 3S, 8S - dihydroxydec - 9 - en - 4, 6 - yne 1 - O - β - D - glucopyranoside (3), and one new glucosyl caffeoate, 1 - O - ethyl - 6 - O - caffeoyl - β - D - glucopyranose (4), together with 34 known compounds were isolated from Artemisia capillaris. The structures of the new compounds were determined by extensive spectroscopic analyses including 1D and 2D NMR, HRESIMS, [α]D and CD experiments. Among them, 19 compounds showed activity inhibiting HBsAg secretion; 20 compounds showed activity inhibiting HBeAg secretion; and 25 compounds possessed inhibitory activity against HBV DNA replication according to our anti-HBV assay on HepG 2.2.15 cell line in vitro. The most active compound 12 could inhibit not only the secretions of HBsAg and HBeAg, but also HBV DNA replication with IC50 values of 15.02μM (SI=111.3), 9.00μM (SI=185.9) and 12.01μM (SI=139.2).
Behavioral and chemical evidence is presented for the identity of the male wing pheromone ofEphestia elutella (Hübner) and the role of this pheromone in courtship success is evaluated. Males with the forewing removed experienced a mating success rate less than half of that of either intact males or males that had only the wing gland area remaining of their forewings. GC-MS analysis and microchemical reactions indicated the presence of (E)-phytol and a series of saturated γ-lactones in a methylene chloride extract of the wings. Using an assay of female courtship behavioral response, (E)-phytol was found to evoke an intermediate level of response in females when presented alone, while the complete array of insect-derived γ-lactones produced no significant response. The combination of either γ-decalactone or γ-undecalactone with (E)-phytol in a 1∶2 ratio, however, elicited a female response equivalent to that produced by the unfractionated wing extract.
One new and 16 known compounds were isolated from Abies sibirica. Their structures were assigned mainly on the basis of NMR and MS spectroscopic data. In bioassay for anti-proliferative activity against four human tumor cells, compound 7 exhibited selective anti-proliferative activity against COLO-205 tumor cell with an IC50 value of 0.9 μg/mL.
The brown alga Desmarestia aculeata was found to contain β-carotene, plastoquinone-9, fucoxanthin and a C27 sterol with a novel side chain.
Epoxyparvinolide which belongs to a new class of sesquiterpenoid lactones, the secocaryophyllanolides, was isolated from Pogostemon parviflorus along with friedelin, friedelan-3-ol, phytol and sitosterol. Epoxyparvinolide was characterized as 4,5-epoxy-9,10-secocaryophyllen-9β,10-olide.
A new polyacetylenic fatty acid, (8E,12Z,15Z)-10-hydroxy-8,12,15-octadecatrien-4,6-diynoic acid (1), together with five known metabolites, including two linear diterpenes (3 and 4) and three sterols (5–7), has been isolated from the Chinese green alga Caulerpa racemosa. Its structure was determined on the basis of extensive spectroscopic analysis. Compound 1 represents the first example of polyacetylenic lipids from marine algae up to now, while compound 4 is characterized for the first time in the Caulerpaceae. Furthermore, the chemotaxonomic significance of these compounds was also summarized.
The red seaweed Gracilaria foliifera (Forsskal) Borgesen was examined for the presence of fatty acids, sterols, fatty alcohols and sugars. The fatty acids, identified by a combined GC-MS technique, showed the presence of five methyl esters as pentadecylate, palmitate, margarate, sterate and oleate. The sterol composition, analysed by mass spectrometry, revealed the presence of cholesterol, 22-dehydrocholesterol and desmosterol. An unsaturated fatty alcohol was isolated and its structure was determined by C-13-NMR as 2-methyl-triacont-5,10,16,22,27-pentaen-15-ol. A sugar was also isolated and its structure was characterised through pmr, cmr and F.D. mass spectral techniques as 6-O-dodecyl-alpha-D-glucopyranosyl-(1 --> 2)-beta-D-fructofuranosde.
Particulate samples from the water column were collected monthly from depths of 5–150m, between May 1996 and March 1997, in the northwestern Mediterranean Sea (Ligurian Sea) as part of the DYFAMED project within the French JGOFS program. These samples were analyzed by gas chromatography-electron impact mass spectrometry for their phytol and 3-methylidene-3,7,11-trimethylhexadecan-1,2-diol (phytyldiol) content. The corresponding Chlorophyll Phytyl side chain Photodegradation Index, molar ratio of phytyldiol to phytol, was calculated and the mean amount of chlorophyll photodegraded within the euphotic zone estimated. Seasonal differences in the chlorophyll photodegradation process appear in the one-year study. The chlorophyll appeared more photodegraded in the surface water (generally more than 40% photodegraded at 5–10m) than at the deep chlorophyll maximum (DCM) (40–50m) observed in the summer stratified waters (about 20% photodegraded). This difference was attributed to the healthy state of the phytoplankton community (coincidence with the highest primary production levels) and to the lower intensity of irradiance at the DCM level. On the other hand, the bulk of the detrital chlorophyll (chlorophyll associated with phytodetritus, phaeopigments) undergoes photodegradation before it sinks out of the photic zone. However, in January (winter mixed water) the pigments exported towards the sea floor were less photodegraded. This is thought to result from a shorter period of residence of the pigments in the photic zone due to vertical convection and grazing activity of macrozooplankton (salps), which are producers of rapid sinking fecal pellets.
Rates of photodegradation of chlorophylls in their entirety and of chlorophyll phytyl chains, and time evolution of the Chlorophyll Phytyl side-Chain Photodegradation Index (CPPI) under visible light exposure were determined and compared in laboratory experiments. Killed phytoplanktonic cells of two widespread Bacillariophyceae (Thalassiosira rotula Meun. and Skeletonema costatum (Grev.) Cleve), one widespread Prymnesiophyceae (Emiliania huxleyi (Lohm.) May and Mohler) and one Chlorophyceae (Dunaliella tertiolecta Butch) were used as source of pigments (chlorophyll a, chlorophyll b and phaeophytin a). Chlorophyll and chlorophyll phytyl chain photodegradation and CPPI evolution showed apparent first-order kinetics with respect to light exposure. The in vitro determined degradation rates were approximately 3.5 times higher for the chlorophyll tetrapyrrolic structure than for the phytyl chain. Few variations of the relative photodegradation constant rates were observed between strains: less than 34% for chlorophyll a and 25% for chlorophyll phytyl chain at 20°C. Nonetheless, the photo-oxidation process of the phytyl chain (Q10=2.0) seems more affected by temperature than does chlorophyll a (Q10=1.4). Phytol loss in the dark controls have been attributed to bacterial degradation, and, in the case of S. costatum, chlorophyllase dephytylation seems to have enhanced the potential for bacterial biodegradation. From these results, it clearly appears that in small detrital particles not only chlorophyll a, chlorophyll b and phaeophytin but also their phytyl chains may be rapidly photodegraded in the upper portion of the euphotic zone. The use of the CPPI for monitoring the chlorophyll photo-oxidation process in the aquatic environment is discussed.
84 chemical constituents were isolated from the leaves of Chamaecyparis formosensis. These components include 18 sesquiterpenes, 40 diterpenes, 8 flavones, 7 lignans and 11 miscellaneous compounds. Among them 3 sesquiterpenes, 7 diterpenes and one lignan are new compounds, the structures of which were determined by chemical and spectral methods.
From the aerial parts of Hyptis suaveolens, a novel triterpenoid, hyptadienic acid, was isolated and its structure elucidated as A(1)-1,19α-dihydroxy-urs-2(3),12-dien-28-oic acid. This is the first report of a naturally occurring A-ring contracted triterpene outside the lupane series.
Oxidation of E phytol and chlorophyll a phytyl chain by hydroxyl and peroxy radicals yielded several interesting isoprenoid compounds. Gas chromatography (GC) and GC—mass spectrometry analyses allowed us to identify notably 6,10,14-trimethylpentadecan-2-one, Z and E phytenals, Z and E 3,7,11,15-tetramethyl-2,3-epoxyhexadecanols and 3,7,11,15-tetramethylhexadecan-1,2,3-triol. Different mechanisms were proposed to explain the formation of these degradation products. The detection of Z and E 3,7,11,15-tetramethyl-2,3-epoxyhexadecanols and 3,7,11,15-tetramethylhexadecan-1, 2,3-triol after photodegradation of chlorophyll a in sea water shows that oxy-free radicals act parallel to 1O2 on the phytyl chain during the photodestructive oxidation of this pigment.
A new pyridone alkaloid, 5,6-dihydro-5-hydroxy-1H-pyridin-2-one (1), and a new ester, sintenin (=3-(3,4-dimethoxyphenyl)propyl 3-(3,4-dimethoxyphenyl)propanoate 2), together with three known compounds, 5,6-dihydro-1H-pyridin-2-one (3), d-sesamin (=5,5′-(3a,4,6,6a-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis[1,3-benzodioxole]; 4), and (E)-phytol (=3,7,11,15-tetramethylhexadec-2-en-1-ol; 5) have been isolated from the whole plant of Piper sintenense. The structures of the two new compounds were determined through spectral analyses. Among twenty isolates obtained so far, four compounds exhibited effective cytotoxicities against P-388, HT-29, or A549 cell lines in vitro.
Hypnea cornuta (Kutz.) J. Ag., H. musciformis (Wulf.) Lamour., H. pannosa J. Ag. and H. valentiae (Turn.) Mont., collected from the northern Arabian Sea coast of Pakistan. have been investigated for their fatty acid. sesquiterpene and sterol compositions using EI- and GC-MS and H-1- and C-13-NMR spectroscopy. Palmitic acid was present in largest quantity (55 - 57%) and oleic was the major (7.2-8.4%) unsaturated fatty acid. Filiformin, filiforminol and 10-bromo-7,12-dihydroxy-3,4-laurene were detected only in H. pannosa 22-dehydrocholesterol was the dominant sterol (41 %) in H. valentiae and cholesterol the major sterol (48 - 54%) in the other three species. Pentacosanoic, hexacosenoic and 7-hydroxy tetradec-4-enoic acids, cholestan-3-beta-ol and cholestan-3-beta,6-beta,7-alpha-triol are reported for the first time from any species of Hypnea. Hypnea pannosa and H. valentiae differed remarkably from the other two species, presumably due to their habitat ecology.
3-Methylidene-7,11,15-trimethylhexadecan-1,2-diol (phytyldiol), a specific isoprenoid marker of chlorophyll photodegradation, was identified by GC–EIMS from a number of marine water particles, sediment trap material and Quaternary marine sediment samples. The widespread occurrence of this marker gives for the first time measurable evidence of chlorophyll photodegradation process in marine ecosystems. The use of the molar ratio phytyldiol to phytol is proposed for the study of the photodegradation processes of chlorophyll occurring in the photic layer of the oceans.
The marine sponge Didiscus sp. contains six acyclic diterpenes: (3E,5E,10E)-7-hydroxy-13-keto-3,7,11,15-tetramethylhexadeca-1,3,5,10,14-pentaene (4), (3Z,5E,10E)-7-hydroxy-13-keto-3,7,11,15-tetramethylhexadeca-1,3,5,10,14-pentaene (5), (3E,5E,10E)-7-ethoxy-13-keto-3,7,11,15-tetramethylhexadeca-1,3,5,10,14-pentaene (9), (3Z,5E,10E)-7-ethoxy-13-keto-3,7,11,15-tetramethylhexadeca-1,3,5,10,14-pentaene (10), (3E,5E,10E)-7-ethoxy-3,7,11,15-tetramethylhexadeca-1,3,5,10,14-pentaene (11), and (3Z,5E,10E)-7-ethoxy-3,7,11,15-tetramethylhexadeca-1,3,5,10,14-pentaene (12).
The photodegradation of different lipid compounds was studied in killed cells of Phaeodactylum tricornutum and Dunaliella sp. Chlorophyll phytyl chain was photodegraded to 6,10,14-trimethylpentadecan-2-one and 3-methylidene-7,11,15-trimethylhexadecan-1,2-diol, sterols to 5α- and 6α/6β-hydroxysterols, carotenoids to loliolide and iso-loliolide, and unsaturated fatty acids to C7–C11ω-oxocarboxylic and α,ω-dicarboxylic acids. After elimination of the insufficiently specific photoproducts, 3-methylidene-7,11,15-trimethylhexadecan-1,2-diol, 5α- and 6α/6β-hydroxysterols, C7–C11ω-oxocarboxylic and α,ω-dicarboxylic acids (with C9 as the most abundant species) were selected to constitute a “pool” of useful indicators of photooxidative alterations of phytoplankton.
Twelve sesquiterpenes, seven phenylpropanoids, two sterols, one triterpene, one diterpene and one polyacetylenic compound were identified from the most polar fractions of the hexane extract of the aerial parts of Seseli vayredanum. Twelve of them are new natural products: lβ-senecioyloxy-5βH,6αH,7αH,1OαMe,11αH-eudesm-3-en- 6,12-olide, 1β-senecioyloxy-5βH,6αH,7aH,1OαMe,11αH-eudesma-2,4(15)-dien-6,12-olide, 2α-angeloyloxy-5β- hydroxy-7αH,10βMe-eudesm-3-en-1-one, 8α-angeloyloxy-10β-hydroxy-slov-3-en-6,12-olide, 10β-hydroxy-8α-senecioyloxy-slov-3-en-6,12-olide, 2-oxo-8α-senecioyloxy-5β,6αH-guai-1(10),3,7(11)-trien-6,12-olide, 8β-angeloyloxy-2-oxo- 5βH,6αH-guai-1(10),3,7(11)-trien-6,12-olide, 2-oxo-8β-senecioyloxy-5βH,6αH-guai-1(10),3,7(11)-trien-6,12-olide, 10β- acetoxy-got-angeloyloxy-3β-hydroxy-lβH,6αH,7αH,11αH- guai-4-en-6,12-olide, erythro-l-hydroxy-2-angeloyloxy-3′,4′- methylenedioxy-5′-methoxy-l-phenylpropane, threo-1-hydroxy-2-angeloyloxy-3′,4′-methylenedioxy-5′- methoxy-l- phenylpropane and 1-hydroxy-3′,4′-methylenedioxy-2′,5′-dimethoxy-1- phenylpropane. Their structures were established by spectroscopic methods and chemical correlations.
Six new laurane-type sesquiterpenoids were isolated from the red alga Laurencia nipponica Yamada and their structures were established on the basis of spectral and chemical evidence.
Three novel neo-clerodane diterpenoids, namely, 15,16-epoxy-7α,18-dihydroxy-15-oxo-ent-cleroda-3-ene,7α,15,18-trihydroxy-ent-cleroda-3-ene and 15,16-diacetoxy-7α,18-dihydroxy-ent-cleroda-3-ene, together with two known diterpenoids, 15,16-epoxy-18-hydroxy-15-methoxy-ent-cleroda-3-ene and 15,16-epoxy-7α,18-dihydroxy-15-methoxy-ent-cleroda-3-ene, were isolated from the aerial parts of Baccharis genistelloides. Eupatorin, cirsimaritin, 5-hydroxy-3′,4′,6,7-tetramethoxyflavone, spathulenol and trans-phytol were also identified from this Baccharis species.
Two varieties of Sideritis massoniana from Madeira (Madeira archipelago) and one from Fuerteventura (Canary Islands) have been examined. Diterpenes, triterpenes, sterols, flavonoids, coumarins and lignans have been isolated. A new coumarin, 7-demethyl-siderin acetate, and the uncommon sterol, 7-oxo-β-sitosterol, have been obtained from S. massoniana var. crassifolia. From the chemosystematic point of view these three taxa of Sideritis belong to one of the groups of the Canarian species of this genus, and should be classified as three different species.
Seven new diterpenes, featuring the rare 2,6-cyclo-xenicane skeleton, along with eleven previously reported metabolites were isolated from the organic extracts of the brown algae Dilophus fasciola and Dilophus spiralis. The structure elucidation of the isolated natural products was based on detailed analyses of their spectroscopic data (NMR, MS, IR, UV), whereas the assignment of their relative configurations was assisted by molecular modelling studies.Graphical abstract
A fresh cake of Chlorella cells was extracted with hot methanol and ether. The extracted lipid was saponified. The unsaponifiable substance, 2.7% of the dried Chlorella cells, was extracted with petroleum ether to separate hydrocarbons and higher alcohols. The extract was fractionated by the vacuum distillation, and each fraction was further separated by the solubility difference of the urea adducts followed by column chromatography. Small amounts of n-hexadecane and n-hexacosene were isolated besides phytol which was the major component of the unsaponifiable substance. Another unsaturated hydrocarbons with straight and branched chain were also found. The residue of the petroleum ether extract was extracted with ether to separate sterols, the major component of which was found to be ergosterol.
Phytol was identified in the chlorophyll-a-containing Fucus vesiculosus and Phormidium luridum by nuclear magnetic resonance, infrared, and mass spectroscopy, and by thin-layer chromatography. It was not accompanied by significant amounts of related isopentenoid alcohols. The development of highly precise control of the isopentenoid pathway leading to phytol and its esterification to chlorophyll is therefore indicated at an early evolutionary stage which seems to be related to the development of the porphyrin pathway but not to the development of chloroplastic and other major subcellular membranes.
The cis- and trans-structures assigned to nerol and geraniol respectively have been confirmed.
Ein Verfahren zur Bestimmung von Phytol nach seiner papierchromatographischen Isolierung aus dem „Unverseifbaren” wird beschrieben. Phytol ist in etiolierten Blttern und in chlorophyllfreien Pflanzenorganen nicht enthalten; es entsteht nur in ergrünenden Chloroplasten. Solange die Blattgrünmenge zunimmt, enthalten diese bedeutend mehr Phytol, als dem Chlorophyllgehalt entspricht. Phytol wurde auch in einigen Pflanzenölen und in der Butter nachgewiesen.
The formation of phytol from [2-14C]mevalonate but not from [1-14C]isopentenyl pyrophosphate was found to be inhibited by phytyl pyrophosphate. Both [U-14C] phytol and [U-14C]phytyl pyrophosphate were incorporated into chlorophyll. Whereas addition of unlabeled phytol reduced the incorporation of [U-14C]phytyl pyrophos-phate, unlabeled phytyl pyrophosphate stimulated the incorporation of [U-14C]phytol into chlorophyll. Phytyl pyrophosphate also stimulated the incorporation of δ-amino-[4-14C]laevulinate into chlorophyll; δ-amino laevulinate stimulated the incorporation of [2-14C]mevalonate, [1-14C]isopentenyl pyrophosphate, and [U-14C]phytol into chlorophyll.