A new serratene triterpenoid from <i>Lycopodium japonicum</i>

Sun, Zhang‐Hua; Li, Wei; Yin, Sheng

doi:10.1080/10286020.2016.1208182

Cited by 10 publications

(5 citation statements)

References 13 publications

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“…Therefore, our sample of the major product was acetylated and analyzed by NMR, which showed complete agreement with the literature values. We also measured 1 H and 13 C NMR in pyridine- d 5 as solvent, which showed complete agreement with the literature data …”

supporting

confidence: 92%

“…Among serratane-type triterpenes, 5 possesses a structure that agrees with this data. The literature data for 5 were reported with pyridine-d 5 as a solvent, 17 while the data for diacetylated 5 were reported with CDCl 3 . 8 Therefore, our sample of the major product was acetylated and analyzed by NMR, which showed complete agreement with the literature values.…”

mentioning

confidence: 99%

“…We also measured 1 H and 13 C NMR in pyridine-d 5 as solvent, which showed complete agreement with the literature data. 17 To further clarify the structure including the stereochemistry of the tertiary hydroxyl group at C14, the diacetylated sample was subjected to dehydration conditions using SOCl 2 . Under such conditions, 5 having a β-hydroxyl group at C14 would result in production of serratenediol bearing an olefin between C14−C15, while the α-epimer would give a mixture of serratenediol and its olefinic isomer isoserratenediol having an olefin between C13−C14.…”

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confidence: 99%

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Identification of Serratane Synthase Gene from the Fern Lycopodium clavatum

et al. 2017

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Ferns are known to produce onoceroids including onoceranes and serratanes having unusual structures among triterpenes. From the fern Lycopodium clavatum, a novel onoceroid synthase gene was cloned that showed high sequence identity with a previously identified α-onocerin synthase. Functional analysis by coexpression with pre-α-onocerin synthase in yeast led to the production of tohogenol and serratenediol. The result suggested that serratanes are directly biosynthesized from pre-α-onocerin and not from α-onocerin as previously assumed.

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confidence: 92%

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confidence: 99%

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confidence: 99%

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Identification of Serratane Synthase Gene from the Fern Lycopodium clavatum

et al. 2017

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“…It has been revealed that Lycopodium alkaloids, which possess unprecedented diverse heterocyclic structures, are the major constituents of L. Herba . This herb has also been found to contain triterpenoids [14,15], anthraquinones [16], volatile oils [17], and flavonoids [18]. According to the chemist Ayer [19], Lycopodium alkaloids can be divided into four structural types; namelylycopodine-type, lycodine-type, fawcettimine-type, and miscellaneous-type, which typically contain lycodoline (LDL), α-obscurine (OSR), fawcettimine, and phlegmarine [13], respectively.…”

Section: Introductionmentioning

confidence: 99%

Pharmacokinetic Studies of Three Alkaloids in Rats After Intragastrical Administration of Lycopodii Herba Extract by LC-MS/MS

Wang

et al. 2019

Molecules

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Lycopodii Herba is a widely used traditional medicinal herb, and contains diverse fascinating alkaloids. In this study, a fast and sensitive LC-MS/MS method for the simultaneous determination of lycodoline, α-obscurine, and N-demethyl-α-obscurine from Lycopodii Herba in rat plasma and brain tissue was developed and validated. Biological samples were extracted via a protein precipitation procedure using methanol as the extraction solvent and Huperzine B as the internal standard. Chromatographic separation was carried out using a Thermo Syncronis-C18 column (50 mm × 2.1 mm, 5 μm) and a gradient mobile phase containing methanol and water with 0.05% formic acid. The three alkaloids were detected by positive electrospray ionization in selective reaction monitoring mode. The selectivity, crosstalk, carryover effect, linearity, accuracy, precision, extraction recovery, matrix effect, and stability of the current method were validated. Then, using the validated method, the plasma pharmacokinetics and brain tissue distribution of the alkaloids in rats were investigated after intragastrical administration of Lycopodii Herba extract. The three alkaloids were shown to be rapidly absorbed into the blood (Tmax, 0.79–1.58 h), and then also eliminated rapidly (t1/2, 1.27–2.24 h). All of them could pass through the blood–brain barrier. The method provides a new research approach to expand preclinical studies of Lycopodii Herba.

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“…This plant was used as a traditional herbal medicine for the treatment of arthritis pain, contusion and myasthenia [1][2]. Previous phytochemical investigations of L. japonicum were mainly focused on the lycopodium alkaloids [3][4][5][6], and serratene-type triterpenoids [7][8][9][10], which were characteristic constituents of this genus. However, there has been little research on other types of compounds, such as flavonoids and lignans.…”

Section: Introductionmentioning

confidence: 99%

Two New Lignans from Lycopodium japonicum Thunb.

Ren¹,

Zou²,

Liu³

et al. 2019

Rec.Nat.Prod.

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Two new lignans, named lycojaponicumoside A (1) and B (2), together with four known compounds (3˗6) were isolated from the n-BuOH extract of Lycopodium japonicum. Their structures were elucidated on the basis of extensive spectroscopic methods, especially various NMR techniques, HRESIMS and circular dichroism (CD). The absolute configuration of compound 1 was established by the calculation of electronic circular dichroism (ECD) curves. All of the compounds were evaluated for their cytotoxic activities against A549 and HepG2 human cancer cell lines, but those compounds did not exhibit cytotoxicity.

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A new serratene triterpenoid from Lycopodium japonicum

Cited by 10 publications

References 13 publications

Identification of Serratane Synthase Gene from the Fern Lycopodium clavatum

Identification of Serratane Synthase Gene from the Fern Lycopodium clavatum

Pharmacokinetic Studies of Three Alkaloids in Rats After Intragastrical Administration of Lycopodii Herba Extract by LC-MS/MS

Two New Lignans from Lycopodium japonicum Thunb.

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