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Chemotaxonomy of Ferns, 3. Triterpenoids from Polypodium polypodioides
... P. hastata is used as a folk herb in traditional Chinese medicine for the treatment of a wide range of ailments, such as bronchitis, fever, and urinary tract infection, and it is especially useful in the external treatment of carbuncles, furunculosis and viper bites (Fang et al., 2007;Qian and Liu, 2011). Previous phytochemical investigations of this species have reported the identification of steroids (Yang et al., 2014), triterpenoids (Yang et al., 2014), polyphenols (Li et al., 2018), flavonoids (Duan et al., 2014), and fatty acid derivatives (Ageta and Arai, 1990), with varied biological activities, including antidiabetic (Ma et al., 2013) and antioxidative (Duan et al., 2014;Su et al., 2011) activities. Although many phytochemical studies have been conducted since 1928 (Suzuki, 1928), the effective components of P. hastata are not yet fully clarified. ...
A phytochemical investigation of Phymatopteris hastata led to the isolation of fourteen natural compounds, including a novel protocatechuic acid methyl ester, [protocatechuic acid methyl ester-4-O-(6′-O-protocatechuoyl)-β-d-glucopyranoside, 1], and one enantiomeric pair of new dihydroflavones (2a/2b), together with twelve known compounds (3∼14). The structures of the new compounds were elucidated following a comprehensive analysis of spectroscopic data from HR-ESI-MS, 1D and 2D NMR, and optical rotatory dispersion (ORD), as well as acidic hydrolysis. Compounds 1, 2, 4, 7, 9, 10, 12, and 13 were isolated from P. hastata for the first time. All compounds isolated from P. hastata were investigated for their α-glucosidase inhibitory activity in vitro. Compound 11 showed a significant α-glucosidase inhibitory activity (IC50 value of 88 ± 3.6 μg/mL) and acted as a noncompetitive inhibitor.
... This might ascribe the activity to phenolic compounds; nevertheless, the Pearson values dismiss the positive correlation between IC 50 values in the tyrosinase assay and TPC. Due to the fact that flavonoids have been described in certain species of the Polypodiaceae family [60,61], we might assume that anti-tyrosinase activity of methanolic and hexane extracts could be due to flavonoids; however, this is not completely in agreement with our results, and other authors have found that the inhibition of tyrosinase could be also due to cycloartanes derivatives isolated in PV [62][63][64]. ...
Ferns are poorly explored species from a pharmaceutical perspective compared to other terrestrial plants. In this work, the antioxidant and tyrosinase inhibitory activities of hydrophilic and lipophilic extracts, together with total polyphenol content, were evaluated in order to explore the potential cosmetic applications of four Spanish ferns collected in the Prades Mountains (Polypodium vulgare L., Asplenium adiantum-nigrum L., Asplenium trichomanes L., and Ceterach officinarum Willd). The antioxidant activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, oxygen radical absorbance capacity (ORAC) and xanthine/xanthine oxidase (X/XO) assays. The potential to avoid skin hyperpigmentation was tested by inhibiting the tyrosinase enzyme, as this causes melanin synthesis in the epidermis. All ferns were confirmed as antioxidant and anti-tyrosinase agents, but interestingly hydrophilic extracts (obtained with methanol) were more potent and effective compared to lipophilic extracts (obtained with hexane). Polypodium vulgare, Asplenium adiantum-nigrum, and Ceterach officinarum methanolic extracts performed the best as antioxidants. Polypodium vulgare methanolic extract also showed the highest activity as a tyrosinase inhibitor.
... The resurrection fern Pleopeltis polypodioides (L.) E.G. Andrews & Windham (Polypodiaceae), also known as Polypodium polypodioides, is an epiphyte that grows on tree limbs and is widespread from southeastern US through most of Latin America (Austin, 2004;Layton et al., 2010). Various terpenoids belonging to the hopane, serratane, cycloartane, malabaricane and polypodane groups have been isolated from this fern (Ageta and Arai, 1990). P. polypodioides was used by the Aztecs as diuretic, against renal stones, cystitis and liver infections. ...
Resurrection species are a group of land plants that can tolerate extreme desiccation of their vegetative tissues during harsh drought stress, and still quickly - often within hours - regain normal physiological and metabolic functions following rehydration. At the molecular level, this desiccation tolerance is attributed to basal cellular mechanisms including the constitutive expression of stress-associated genes and high levels of protective metabolites present already in the absence of stress, as well as to transcriptome and metabolome reconfigurations rapidly occurring during the initial phases of drought stress. Parts of this response is conferred by unique metabolites, including a diverse array of sugars, phenolic compounds, and polyols, some of which accumulate to high concentrations within the plant cell. In addition to drought stress, these metabolites are proposed to contribute to the protection against other abiotic stresses and to an increased oxidative stress tolerance. Recently, extracts of resurrection species and particular secondary metabolites therein were reported to display biological activities of importance to medicine, with e.g. antibacterial, anticancer, antifungal, antiviral activities, making them possible candidates for the development of novel drug substances as well as for cosmetics. Herein, we provide an overview of the metabolite composition of resurrection species, summarize the latest reports related to the use of natural products from resurrection plants, and outline their potential for medical applications.
... A total of 50 fractions of 300 ml each were collected and combined on the basis of TLC analysis leading to two main series (I and II). Series I (1.5 g) [fractions 1–37] was column chromatographed on silica gel and eluted with CH 2 Cl 2 –MeOH (3:1) to yield friedelin C 30 H 50 O [6, White powder; R f : 0.7 (CH 2 Cl 2 ); 3.9 mg; m.p.: 247–249 °C; m/z: 426] (Ageta and Arai, 1990). Series II (0.9 g) [fractions 38–50] eluted with CH 2 Cl 2 –MeOH (7:9) yielded friedelin-3β-ol C 30 H 52 O [5, White powder; R f : 0.6 (CH 2 Cl 2 ); 5.4 mg; m.p.: 229–231 °C; m/z: 428] (Fun et al., 2007; Ng'ang'a et al., 2008). ...
This study was designed to evaluate the antimycobacterial, antibacterial and antifungal activities of the methanol extract from the stem bark of Thecacoris annobonae Pax & K. Hoffm, that of aristolochic acid I (1) and other isolated compounds. The microplate alamar blue assay (MABA) and the broth microdilution method were used to determine the minimal inhibitory concentration (MIC) and minimal microbicidal concentration (MMC) of the above samples. The H+-ATPase-mediated proton pumping assay was used to evaluate a possible mechanism of action for both the methanol extract and aristolochic acid I. The results of the MIC determinations showed that the methanol extract and aristolochic acid I prevent the growth of all studied organisms. The results obtained in this study also showed that the methanol extract as well as aristolochic acid I inhibited the H+-ATPase activity. The overall results provided evidence that the methanol extract of T. annobonae might be a potential source of new antimicrobial drug against tuberculosis, and some bacterial and fungal diseases, but should be consumed with caution, bearing in mind that the main active component, aristolochic acid I is a potentially toxic compound.
An efficient, convenient short synthetic procedure for synthesis of the intricate 5A5B6C-ring fusion topologies of tricyclic spiranoid β-hydroxybutyrolactones through lactonization of the key intermediate trans-ɑ-hydroxyindenones with malonates is described. All...
Phytochemical investigations on Polypodium hastatum have led to the isolation of three isomers of coumaric acid glucosides. Their structures were identified as trans-melilotoside (1), trans-coumaric acid-3-O-β-Dglucopyranoside (2), and trans-coumaric acid-4-O-β-D-glucopyranoside (3) by spectroscopic analysis. Compound 2 is a new natural product.
Phytochemical investigation on the whole plant of Polypodiun hastatum Thunb. leads to the isolation of six flavonoids including (+)-afzelechin-5-O-β-D-apiofuranoside (1), kaempferol-7-O-α-L-rhamnopyranoside (2), juglanin (3), 3-O-α-L-arabinofuranosyl-kaempferol-7-O-α-L-rhamnopyranoside (4), 3-O-α-Lrhamnopyranosyl- kaempferol-7-O-α-L-rhamnopyranoside (5), and 3-O-β-D-apiofuranosyl-(1→2)-α-Lrhamnopyranosyl- kaempferol-7-O-α-L-rhamnopyranoside (6). Their structures were detrmined on the basis of spectroscopic analysis. All the flavonoids were obtained from the plant for the first time including a new one, (+)-afzelechin-5-O-β-D-apiofuranoside. Their antioxidative activity was evaluated via DPPH radical scavenging assay and ABTS•+ radical scavenging assay.
The evolutionary origin of land plants (embryophytes) from their green algal ancestors was a pivotal event in the history of life (388, 533). Morphological and genetic studies have identified two distinct lineages within the green algae, termed Chlorophyta and Charophyta (114, 466). There is a concept that land plants descended from ancestral charophycean algae, and currently this theory is supported by molecular, biochemical, and ultrastructural evidence (388, 533). Red algae (Fig. 9.1) seem to be the most anciently emerged group among the eukaryotes 9–32) (469). The red and green algae sisterhood has been recently supported by molecular analysis (551). Phylogenetic studies have also been shown that heterokont algae (brown and yellow-green algae) possess red-algal plastids (462). However, the brown algae, in comparison to the green algae, are considered evolutionarily to be very different from the green plants (green algae, bryophytes, vascular plants) and are not closely related to each other, according to modern phylogenetic results (111).
Ten malabaricane type triterpenes were isolated from the oleoresin of Ailanthus malabarica, out of which six (1-6) were new. For three of the known compounds (7-9), NMR assignments are being reported for the first time. Compound 10, a known one, is a new report from this source. The structures were established by extensive 1D and 2D NMR spectroscopy. The oleoresin and some of the isolates did not possess antimicrobial activity and did not lyse RBCs.
Copyright © 2014. Published by Elsevier B.V.
Phytochemical investigation on a Chinese fern Polypodium hastatum resulted in the isolation of three flavonoid glycosides, one steroid and one coumarin. Their structures were identified as β-sitosterol (1), coumarin (2), juglanin (3), kaempferol-7-O-α-l-rhamnopyranoside (4) and (+)-afzelechin-5-O-β-d-apiofuranoside (5) on the basis of spectroscopic analysis including UV, MS, 1D and 2D NMR, and chemical and physical properties. (+)-Afzelechin-5-O-β-d-apiofuranoside was a new flavonoid glycoside. Chemotaxonomic significance of this investigation was summarized.
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Brazil possesses great biological and cultural diversity, above all, in view of the great number of indigenous ethnic groups - 218 in all - that inhabit the five main biomas in Brazil. The purpose of this review is to analyze the relationship between chemical constituents of species utilized by several groups of Brazilian Indians and the uses/indications made of the species by these same groups using ethnopharmacological surveys by different researchers, as from the seventies. The 34 publications selected, involving 26 indigenous ethnic groups, showed a total of 307 species utilized for 67 different diseases or effects possibly related to the Central Nervous System (CNS). These plants belong to 85 taxonomic families, mostly Fabaceae, Asteraceae, Rubiaceae, Poaceae, Apocynaceae, Bignoniaceae, Euphorbiaceae, and Solanaceae. The chemical constitution of these plants was researched as from the Pubmed and Web of Science and the information obtained was crossed with different indigenous uses, grouped in 12 categories according to similarities between their expected effects on the CNS: analgesics, to counteract fever, tonics and/or adaptogens, hallucinogens, anxiolytics, anticonvulsants, head illnesses, hypnotics, stimulants, weight control, memory enhancers, and others. Some phytochemical classes were observed to be more common among plants utilized for certain purposes: flavonoids (analgesia, fever, anxiety, hypnotic, weight control, and as a stimulant), alkaloids (hallucinogens, head illnesses, and as a stimulant), essential oils (fever and anxiety), lignans (hallucinogen), tannins (anxiety), triterpenes and saponins (hypnotic). These data suggest that these phytochemical classes possibly possess a greater number of chemical constituents that perform the effects described or that, in some way, assist in determining the use of the plant by the Indians.
Squalene epoxidase converts squalene into oxidosqualene, the precursor of all known angiosperm cyclic triterpenoids, which include membrane sterols, brassinosteroid phytohormones, and non-steroidal triterpenoids. In this work, we have identified six putative Arabidopsis squalene epoxidase (SQE) enzymes and used heterologous expression in yeast to demonstrate that three of these enzymes, SQE1, SQE2, and SQE3, can epoxidize squalene. We isolated and characterized Arabidopsis sqe1 mutants and discovered severe developmental defects, including reduced root and hypocotyl elongation. Adult sqe1-3 and sqe1-4 plants have diminished stature and produce inviable seeds. The sqe1-3 mutant accumulates squalene, consistent with a block in the triterpenoid biosynthetic pathway. Therefore, SQE1 function is necessary for normal plant development, and the five SQE-like genes remaining in this mutant are not fully redundant with SQE1.
Arabidopsis thaliana is a well-established model organism for plant genetics, and its recently sequenced genome reveals a wealth of enzymes similar to known examples that biosynthesize secondary metabolites. We describe experiments that exploit this genomic information to identify novel terpenoids. A predicted open reading frame with high similarity to known oxidosqualene cyclases was shown to convert 3(S)-oxidosqualene to the previously unknown triterpene alcohol (3S,13S,14R)-malabarica-8,17,21-trien-3-ol, which we named thalianol. Genome mining offers a systematic approach to exhaustively characterize the biosynthetic potential of an organism, and is considerably more sensitive than classical approaches. Because even rare transcripts can be heterologously expressed at high levels, genome mining coupled to heterologous expression may be more sensitive than classical extraction approaches for isolating and characterizing trace metabolites.
From the rhizomes of Polypodium formosanum, new triterpenoids of the cycloartane group, (24R)-cyclolaudenol and (24R)-cyclomargenol, were isolated as the corresponding acetates, alcohols and ketones, and their structures were established. Also, from the rhizomes of P. niponicum eight acetates of cycloartane derivatives and two acetates of new methyl sterols were isolated and characterized.
7 mg, mp 240'; Y max(KBr) 3030, 1655,790; relRt 2.35
- Smut-Z4ae
Smut-Z4ae[2].-7
mg, mp 240'; Y max(KBr) 3030, 1655,790; relRt 2.35; eimsm/z [MI+ 410
Rel Rt 4.05; eims m/z
- Cycfoartenyl
Cycfoartenyl acetate [12].-Rel Rt 4.05; eims m/z [MI+ 468 (12), 453 (13), 408 (84), 393 (loo), 300
Fraction V was chromatographed on N203 (grade 111) with n- Orton acetal [14].-A white powder: 31 mg, mp 197-201'; [ c Y ] ~ ~ D +4.6" (c= 0.2, CHCI,); Y rnax Friedelin
- And Alcohols
ACETAL, KETONE, AND ALcOHoLs.-Fraction V was chromatographed on N203 (grade 111) with n-
Orton acetal [14].-A white powder: 31 mg, mp 197-201'; [ c Y ] ~ ~ D
+4.6" (c= 0.2, CHCI,); Y rnax
Friedelin [ l 8 ]. d O mg, rnp 27 1-272'; v rnax (KBr) 17 18.
Fraction Iv was chromatographed on si gel with n-he%an&&6 3Z-Nwcycfofu&ylacetare [ll].-Rel Rt 3.94; eims m/z
- Cycloartanoid Acetates
CYCLOARTANOID ACETATES.-Fraction Iv was chromatographed on si gel with n-he%an&&6
3Z-Nwcycfofu&ylacetare [ll].-Rel
Rt 3.94; eims m/z [MI+ 468 (3), 453 (18), 408 (loo), 300
88 (75%), eims 414 [MI+; stigmasterol, re1 Rt 2.50(16%), eims 412 [MI+; campesterol
- Sterofmzxture
Sterofmzxture.-Sitosterol, re1 Rt 2.88 (75%), eims 414 [MI+; stigmasterol, re1 Rt 2.50(16%), eims
412 [MI+; campesterol, re1 Rt 2.40 (1 l%), eims 400 [MI+.
- K Masuda
- K Shiojima
- H Ageta
K. Masuda, K. Shiojima, and H. Ageta, C h. Pbann. Bull., 37, 1140 (1989).
- G J B M Bory
G.J.B.M. Bory, Dict. Class. BHist. Nut., 6, 587 (1824).
- T Nakai
- H Ito
T. Nakai and H. Ito, J. Jpn. Bot., 1 1, 95 (1935).
-26 rng, rnp 245-246"; Y rnax (KBr) 3350
- Dryorrarsol
Dryorrarsol[19].-26 rng, rnp 245-246"; Y rnax (KBr) 3350, 1028.
- C Ching
C. Ching, AOU Pbytotaxon. Sin., 1 6, 16 (1978).
d O mg, rnp 27 1-272'; v rnax (KBr)
- Friedelin
Friedelin [ l 8 ]. d O mg, rnp 27 1-272'; v rnax (KBr) 17 18.
- G J B M Bory
G.J.B.M. Bory,Dict. Clars. BHist. Nut., 1 0, 176(1826).
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- F Bottari
- A Marsili
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- M Polvani
- A Mandelbaum
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(1967).
- Y Saiki
Y. Saiki, J. Pbytogmgr. and Taxon., 35, 75 (1987).
75 rng, mp 254255'; Y max (KBr) 3600
- Hydmxyhopune
Hydmxyhopune [15].-75
rng, mp 254255'; Y max (KBr) 3600, 3450, 1030.
- G Berti
- F Bottari
- A Mansili
- I Morelli
- A Mandelbaum
G. Berti, F. Bottari, A. Mansili, I. Morelli, and A. Mandelbaum, C h. Commun., 507 (1967).
- H Ageta
- K Shiojima
- K Masuda
H. Ageta, K. Shiojima, and K. Masuda, C h. Phunn. B d l., 30, 2272 (1982).
Fraction V was chromatographed on N203 (grade 111) with n-Orton acetal [14].-A white powder: 31 mg
- Ketone Acetal
- Alcohols
ACETAL, KETONE, AND ALcOHoLs.-Fraction V was chromatographed on N203 (grade 111) with n-Orton acetal [14].-A white powder: 31 mg, mp 197-201'; [ c Y ]~~D +4.6" (c= 0.2, CHCI,); Y rnax
Friedelin [ l 8 ].
Tentamen Pteridographiae
- C B Presl
C.B. Presl, "Tentamen Pteridographiae," Prague, 1836, p. 186.
H. Ageta and Y. Arai, Pbytwhistty, 22, 1808 (1983).
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- R Beugelmaw
- B C Das
H.E. Audier, R. Beugelmaw, and B.C. Das, Tetrabedmn Lett., 4343 (1966).
- H Ageta
- K Shiojima
- Y Arai
- T Kasama
- K Kajii
H. Ageta, K. Shiojima, Y. Arai, T. Kasama, and K. Kajii, Tetrubedmn Lett., 3297 (1975).
- T Takahashi
T. Takahashi, Nippon Kagaku Zasshi, 8 7, 101 (1966).