Growing with dinosaurs: natural products from the Cretaceous relict Metasequoia glyptostroboides Hu &amp; Cheng—a molecular reservoir from the ancient world with potential in modern medicine

Juvik, Ole Johan; Nguyen, Xuan Hong Thy; Andersen, Heidi Lie; Fossen, Torgils

doi:10.1007/s11101-015-9395-3

Cited by 17 publications

(8 citation statements)

References 78 publications

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“…Sugiol (18) is also active against various foodborne pathogenic bacteria but neutralises Gram-positive bacteria more effectively than Gram-negative bacteria. When isolated from Metasequoia glyptostroboides cones, the compound was also found to demonstrate stronger antibacterial action against Gram-positive bacteria than the streptomycin used as a control [ 57 ]. Sugiol (18) has also been found to exhibit antiviral activity against the H1N1 virus in infected Madin-Darby canine kidney (MDCK) cells: no cytopathic changes were observed following 72 h of exposure following treatment with 500 μg mL −1 sugiol (18) .…”

Section: A Review Of Diterpenoid Compounds Isolated From Cl...mentioning

confidence: 99%

Biologically Active Diterpenoids in the Clerodendrum Genus—A Review

Kuźma

Gomulski

2022

IJMS

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One of the key areas of interest in pharmacognosy is that of the diterpenoids; many studies have been performed to identify new sources, their optimal isolation and biological properties. An important source of abietane-, pimarane-, clerodane-type diterpenoids and their derivatives are the members of the genus Clerodendrum, of the Lamiaceae. Due to their diverse chemical nature, and the type of plant material, a range of extraction techniques are needed with various temperatures, solvent types and extraction times, as well as the use of an ultrasound bath. The diterpenoids isolated from Clerodendrum demonstrate a range of cytotoxic, anti-proliferative, antibacterial, anti-parasitic and anti-inflammatory activities. This review describes the various biological activities of the diterpenoids isolated so far from species of Clerodendrum with the indication of the most active ones, as well as those from other plant sources, taking into account their structure in terms of their activity, and summarises the methods for their extraction.

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Section: A Review Of Diterpenoid Compounds Isolated From Cl...mentioning

confidence: 99%

Biologically Active Diterpenoids in the Clerodendrum Genus—A Review

Kuźma

Gomulski

2022

IJMS

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“…The signals with those characteristics are specific for 1,4disubstituted benzene. The chemical shift values of 1 H-NMR and 13 C-NMR from VDH 8-3-2 compound is concluded in Table 4 (Juvik et al, 2016). Mastura, Tonel Barus, Lamek Marpaung, & Partomuan Simanjuntak : Isolation and Antioxidant Activity of Phenolic Compounds from Halban Leaves (Vitex pinnata Linn) in Aceh Table 4.…”

Section: Identification Of Vdh 8-3-2 and Vdh 9-3-13 Compounds Based Omentioning

confidence: 99%

Isolation and Antioxidant Activity of Phenolic Compounds from Halban Leaves (Vitex pinnata Linn) in Aceh

Mastura

Barus

Marpaung

et al. 2020

EKW

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An isolation and identification of phenolic compounds from Halban Leaves (Vitex pinnata Linn), a traditional medicinal plant in Aceh, has been done. Halban leaves were extracted through methanol maceration followed by isolation. The methanol extract went into n-hexane and ethyl acetate partition consecutively resulting in 3 different fractions of ethyl acetate and n-hexane extract. The ethyl acetate fraction demonstrated the most promising antioxidant and cytotoxic activity. Therefore, purification of ethyl acetate fraction was done by column chromatography [SiO2; (i) n-hexane-ethyl acetate 10:1, 1:1 ; (ii) n-hexane-ethyl acetate = 2 : 1); (iii) n-hexane-acetone = 1:1]. The pure isolate as identified by using UV, IR, NMR, and MS spectra afforded 2 phenolic compounds, namely (1) 4-hydroxymethyl benzoate and (2) p-hydroxymethyl benzoic acid (PHBA). The antioxidant activity of compound 1 and cytotoxicity activity of 2 expressed in IC50 and LD50 was 41.08 ppm and 59.41 ppm, respectively.Abstrak: Isolasi dan identifikasi senyawa fenolik dari Daun Halban (Vite xpinnata Linn) tanaman obat tradisional asal Aceh telah dilakukan. Isolasi ini dilakukan dengan cara mengekstraksi daun halban dengan cara maserasi menggunakan pelarut metanol, Ekstrak metanol kemudian dipartiisi dengan n-heksan dan etilasetat secara berturut-turut sehingga diperoleh tiga ekstrak yaitu ekstrak etil asetat, n-heksan dan air. Ekstrak etil asetat memiliki bioaktivitas sebagai antioksidan dan juga toksisitas. Pemurnian dilanjutkan dengan cara kromatografi kolom [SiO2; (i) n-heksan-etilasetat 10:1, 1:1 ; (ii) n-heksan-etilasetat = 2 : 1); (iii) n-heksan-aseton = 1:1] dan diperoleh isolat murni. Isolat murni tersebut diidentifikasi berdasarkan interpretasi data spektra UV, IR, NMR dan MS. Hasil interpretasi data menunjukkan daun halban (V. pinnata Linn) mengandung dua senyawa fenolik yaitu (1) 4-hidroksi metil benzoat dan (2) asam para hidroksi benzoat (PHBA). Senyawa 1 memiliki aktivitas antioksidan dengan nilai IC50 = 41,08bpj dan senyawa 2 memiliki aktivitas toksisitas dengan nilai LC50 = 59,41.

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“…Thus, investigations of secondary substances in M. glyptostroboides have been conducted since the 1950s [9,10]. A significant number of the secondary substances, such as fatty acids, flavonoids, lignans, and terpenoids, have been isolated and characterized in leaves, stems, and cones including fossil leaves of M. glyptostroboides [11].…”

Section: Introductionmentioning

confidence: 99%

“…Terpenoids are the largest group of those secondary substances found in M. glyptostroboides. Dozens of new compounds were also characterized from the species, and majority of new compounds belongs to lignans and norlignans [11]. Lignans are widely distributed in the plant kingdom, but norlignans are mainly distributed in conifers [12].…”

Section: Introductionmentioning

confidence: 99%

Allelopathy and Allelopathic Substances of Fossil Tree Species Metasequoia glyptostroboides

et al. 2021

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Metasequoia glyptostroboides Hu et W.C. Cheng is one of the oldest living conifer species, and it has remained unchanged for millions of years compared to its fossils from the Cretaceous period. The species are cultivated in the parks, gardens, and roadsides in many countries. We investigated the allelopathy and allelopathic substances in fallen leaves of M. glyptostroboides. An aqueous methanol extract of the fallen leaves inhibited the growth of cress (Lepidium sativum L.), lettuce (Lactuca sativa L.), alfalfa (Medicago sativa L.), Lolium multiflorum Lam., Phleum pretense L., and Vulpia myuros (L.) C.C.Gmel. The extract was then purified by several chromatographic steps, and two allelopathic substances were isolated and determined by spectral data to be (+)-rhododendrol and 9-epi-blumenol C. The compound inhibited the growth of cress and L. multiflorum. M. glyptostroboides is a deciduous perennial tree, and accumulation of its fallen leaves occur on the soil under the trees. Therefore, those allelopathic substances in the fallen leaves may be liberated into the rhizosphere soil during the decomposition process of fallen leaves and provide a competitive advantage for M. glyptostrob through the growth inhibition of competing plant species nearby. Therefore, M. glyptostroboides is allelopathic, and (+)-rhododendrol and 9-epi-blumenol C may be contribute to the allelopathy.

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Growing with dinosaurs: natural products from the Cretaceous relict Metasequoia glyptostroboides Hu & Cheng—a molecular reservoir from the ancient world with potential in modern medicine

Cited by 17 publications

References 78 publications

Biologically Active Diterpenoids in the Clerodendrum Genus—A Review

Biologically Active Diterpenoids in the Clerodendrum Genus—A Review

Isolation and Antioxidant Activity of Phenolic Compounds from Halban Leaves (Vitex pinnata Linn) in Aceh

Allelopathy and Allelopathic Substances of Fossil Tree Species Metasequoia glyptostroboides

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