A New Drimane Sesquiterpene, Isomers of Manoyl Oxide and Other Volatile Constituents from the Resin “Ladano” of<i>Cistus incanus</i>subsp.<i>creticus</i>(L.) Heywood

Demetzos, Costas; Mitaku, Sofia; Loukis, A.; Harvala, Catherine; Gally, A.

doi:10.1080/10412905.1994.9698322

Cited by 12 publications

(25 citation statements)

References 6 publications

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“…The oil (1.65 g), was chromatographed over 30 g silica gel 60 using n-hexane (500 ml), n-hexane-Et20 (950 ml), followed of CH2CI2 (600 ml) and CH2C12-MeOH (1100 ml) mixtures of increasing polarity, 210 fractions of 15 ml each, were taken and combined based upon TLC monitoring, into 16 fractions (A-Q). In the fraction B (n-hexane-Et20, 98:2), drimane-7,9(11)-diene (4), was identified by GC-MS (RI = 1469) using literature data (8,10). Fraction B was re-chromatographed over 20 g A1203 (neutral 70-230 mesh) using n-hexane as solvent, yielding pure 4 (10mg).…”

Section: Creticusmentioning

confidence: 99%

“…The essential oil of the resin Ladano was re-investigated after fractionation by CC (8). Among the known terpenes identified previously from the essential oil, two labdane type diterpenes which have not been reported in the literature (8), were detected using GC-MS. Ent-3J-hydroxy-13-epi-manoyl oxide (5) was isolated, while its acetylated derivative ent-3/3acetoxy-13-epi-manoyl oxide (7) was obtained after acetylation of 5. Compounds 5 and 7 had identical spectroscopic data obtained from GC-MS analysis, with those of the two detected labdane diterpenes of the oil.…”

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confidence: 99%

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Chemical Analysis and Antimicrobial Activity of the Resin Ladano, of its Essential Oil and of the Isolated Compounds**

Demetzos¹,

Stahl²,

Anastassaki³

et al. 1999

Planta Med

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Fractionation of the resin Ladano from Cistus creticus subsp. creticus and susceptibility testing using the chromatographic fractions showed that its antistaphylococcal activity was mainly due to the diterpene sclareol. The antimicrobial activity of its essential oil, of the chromatographic fractions, and of the isolated compounds was also evaluated against Staphylococcus aureus, Staphylococcus epidermidis, and Staphylococcus hominis.

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Section: Creticusmentioning

confidence: 99%

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confidence: 99%

Chemical Analysis and Antimicrobial Activity of the Resin Ladano, of its Essential Oil and of the Isolated Compounds**

Demetzos¹,

Stahl²,

Anastassaki³

et al. 1999

Planta Med

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“…The resin produced by C. creticus trichomes consists mainly of terpenoids and flavonoids (Chinou et al 1994;Demetzos et al 1994aDemetzos et al , b, 1989 therefore, the presence of ESTs involved in their biosynthesis was as expected. However, the EST analysis revealed the presence of cDNAs in the library encoding enzymes participating in phenylpropanoid biosynthesis, an indication that low molecular weight phenylpropanoids may also contribute to the characteristic odor of C. creticus subsp.…”

Section: Discussionmentioning

confidence: 62%

Transcriptome analysis approaches for the isolation of trichome-specific genes from the medicinal plant Cistus creticus subsp. creticus

et al. 2008

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Cistus creticus subsp. creticus is a plant of intrinsic scientific interest due to the distinctive pharmaceutical properties of its resin. Labdane-type diterpenes, the main constituents of the resin, exhibit considerable antibacterial and cytotoxic activities. In this study chemical analysis of isolated trichomes from different developmental stages revealed that young leaves of 1-2 cm length displayed the highest content of labdane-type diterpenes (80 mg/g fresh weight) whereas trichomes from older leaves (2-3 or 3-4 cm) exhibited gradual decreased concentrations. A cDNA library was constructed enriched in transcripts from trichomes isolated from young leaves, which are characterized by high levels of labdane-type diterpenes. Functional annotation of 2,022 expressed sequence tags (ESTs) from the trichome cDNA library based on homology to A. thaliana genes suggested that 8% of the putative identified sequences were secondary metabolism-related and involved primarily in flavonoid and terpenoid biosynthesis. A significant proportion of the ESTs (38%) displayed no significant similarity to any other DNA deposited in databases, indicating a yet unknown function. Custom DNA microarrays constructed with 1,248 individual clones from the cDNA library facilitated transcriptome comparisons between trichomes and trichome-free tissues. In addition, gene expression studies in various Cistus tissues and organs for one of the genes highlighted as the most differentially expressed by the microarray experiments revealed a putative sesquiterpene synthase with a trichome-specific expression pattern. Full length cDNA isolation and heterologous expression in E. coli followed by biochemical analysis, led to the characterization of the produced protein as germacrene B synthase.

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“…The compounds identified within the LS223 sample by GC-MS analysis are shown in Table 2. Figure 8 depicts the chromatogram of sample LS223, sclareolide and manoyloxide (marked with 1* and 2*') which are the main components of resin ladan, an exudate of Cistus creticus, a plant that grows in Greece, more precisely on the island of Crete (Demetzos et al 1994). From historical research, it seems that the name "Ladon" written on the LS223 sample label may also refer to "ladan" resin.…”

Section: Ls232 Resin Scamon and Ls223 Ladonmentioning

confidence: 99%

“…From historical research, it seems that the name "Ladon" written on the LS223 sample label may also refer to "ladan" resin. Folk medicine used this resin to treat various diseases (Demetzos et al 1994)-e.g. abdominal pain (Rivera et al 2019)-and in the cosmetic industry to create perfumes (Mackonochie and Heinrich 2019).…”

Section: Ls232 Resin Scamon and Ls223 Ladonmentioning

confidence: 99%

New insights into the composition of historical remedies and pharmaceutical formulations: the identification of natural resins and balsams by gas chromatographic-mass spectrometric investigations

Izzo

Lodi

Pascual

2020

Archaeol Anthropol Sci

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The present paper reports one of the first studies on the identification of natural resins and balsams in modern era drug formulations. Gas chromatography coupled with mass spectrometry (GC-MS) was applied to investigate the composition of ancient remedies and pharmaceutical formulations coming from the Spezieria di Santa Maria della Scala in Rome, founded at the end of the seventeenth century by the Discalced Carmelites. The obtained results highlight the presence of complex mixtures containing resinaceous and lipidic-based compounds. Thanks to the detection of characteristic markers, it was possible to identify several natural resins, such as guaiacum resin, ladano resin and scammony resin. Balsamic and aromatic compounds characteristic of essential oils were identified as well. In addition, an anti-inflammatory ointment, composed by mixing Venetian turpentine, a Pinaceae resin and a triterpene resin exudate of a plant from South America, was found among the analysed formulations. Combining the analytical results, the historical research and the botanical composition, it was possible to formulate compositional hypotheses of this historical medicine and provided some indications about their use in health. The study of historical drugs is not only important to know the practices handed down by apothecaries in the past, but also fundamental to reconstruct historical recipes that can inspire new dermatological, cosmetic, hygienic and current curative products.

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A New Drimane Sesquiterpene, Isomers of Manoyl Oxide and Other Volatile Constituents from the Resin “Ladano” ofCistus incanussubsp.creticus(L.) Heywood

Cited by 12 publications

References 6 publications

Chemical Analysis and Antimicrobial Activity of the Resin Ladano, of its Essential Oil and of the Isolated Compounds**

Chemical Analysis and Antimicrobial Activity of the Resin Ladano, of its Essential Oil and of the Isolated Compounds**

Transcriptome analysis approaches for the isolation of trichome-specific genes from the medicinal plant Cistus creticus subsp. creticus

New insights into the composition of historical remedies and pharmaceutical formulations: the identification of natural resins and balsams by gas chromatographic-mass spectrometric investigations

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