Premarrubiin. A diterpenoid from Marrubium vulgare L

Henderson, M. S.; McCrindle, Robert

doi:10.1039/j39690002014

Cited by 34 publications

(35 citation statements)

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“…This could be the reason that poor incorporation of MVA into certain classes of isoprenoids could often be partly explained by compartmentation. It will be interesting to know whether the biosynthetic pathway in plastids Scheme 3 13 C labelling of IPP and marrubiin from [1][2][3][4][5][6][7][8][9][10][11][12][13] …”

Section: Biosynthesis Of Isoprenoids In Higher Plantsmentioning

confidence: 99%

“…The furanic labdane diterpene marrubiin is the bitter principle in extracts from the medicinal plant M. ulgare. The substance is formed from the authentic compound premarrubiin during extraction (for structures see Figure 1) [8]. The system has some features that make it suitable for biosynthetic studies : (1) marrubiin is accumulated in large amounts in the aerial parts of the plant as well as in differentiated shoot cultures, (2) the furanic moiety can be easily detected, (3) the compound is not volatile and (4) the labdane skeleton is derived from the direct cyclization Abbreviations used : GGPP, geranylgeranyl diphosphate ; IPP, isopentenyl diphosphate ; MVA, mevalonic acid.…”

Section: Introductionmentioning

confidence: 99%

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Biosynthesis of the labdane diterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway

Knöß

Reuter

Zapp

1997

Biochemical Journal

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The biosynthesis of the furanic labdane diterpene marrubiin has been studied in plantlets and shoot cultures of Marrubium vulgare(Lamiaceae). The use of [2-14C]acetate, [2-14C]pyruvate, [2-14C]mevalonic acid and [U-14C]glucose incorporation experiments showed that the labelling of sterols in etiolated shoot cultures of M. vulgare was in accordance with their biosynthesis via the acetate–mevalonate pathway. In contrast, the incorporation rates of these precursors into the diterpene marrubiin could not be explained by biosynthesis of this compound via the acetate–mevalonate pathway. Cultivation of etiolated shoot cultures of M. vulgare on medium containing [1-13C]glucose and subsequent 13C-NMR spectroscopy of marrubiin led to the conclusion that the biosynthesis of marrubiin follows a non-mevalonate pathway. All isoprenic units of 13C-labelled marrubiin were enriched in those carbons that correspond to positions 1 and 5 of a putative precursor isopentenyl diphosphate. This labelling pattern from [1-13C]glucose is consistent with an alternative pathway via trioses, which has already been shown to occur in Eubacteria and Gymnospermae. The labdane skeleton is a precursor of many other skeletal types of diterpenes. Therefore it becomes obvious that in connection with the few known examples of a non-mevalonate pathway to isoprenoids the formation of some isoprenoids in plants via a non-mevalonate pathway might be quite common.

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Section: Biosynthesis Of Isoprenoids In Higher Plantsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Biosynthesis of the labdane diterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway

Knöß

Reuter

Zapp

1997

Biochemical Journal

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“…This compound was identified as the bitter principle of the drug in the 19th century, and its structure was elucidated in 1953 (Cocker et al 1953). The structure and the conformation has been verified by X-ray studies (Busby et al 1983), and it has been found that the genuine compound occurring in the plant is premarrubiin (Henderson and McCrindle 1969). The amount of diterpenes in field grown plants is up to 4mg/g FW.…”

Section: Extraction and Structure Of Furanic Labdane Diterpenesmentioning

confidence: 96%

Marrubium vulgare (White Horehound): In Vitro Culture, and the Production of Diterpene Marrubiin and Other Secondary Metabolites

Knöß

1999

Medicinal and Aromatic Plants XI

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“…Premarrubiin, premarrubenol, and vulgarol have been also reported in M. vulgare shoots [17,42,43]. In a study, labdane skeleton was served as a precursor for many diterpenes and in the biosynthesis of marrubiin which follows a non-mevalonate pathway in plantlets and shoot culture of M. vulgare [44].…”

Section: Diterpenoidsmentioning

confidence: 99%

Marrubium vulgare L.: A review on phytochemical and pharmacological aspects

Lodhi¹,

Vadnere²,

Sharma³

et al. 2017

J Intercult Ethnopharmacol

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Marrubium vulgare L. (family: Lamiaceae), also known as the white horehound, is widely used as an herbal remedy for chronic coughs and colds. It is used in various disorders related to skin, liver, gastric, heart, and immune system. This review abridges phytochemical, pharmacological studies, and medicinal uses of M. vulgare and provides scientific proof for various ethnobotanical claims to identify gaps, which will give impulsion for novel research on M. vulgare based herbal medicines. This review summarizes selected scientific evidence on phytochemistry and pharmacological properties of M. vulgare over the past 48 years . Works related to M. vulgare was reviewed from various sources such as books, internet source, i.e., Google Search engine, PubMed, and Science Direct, and chemical abstract. The exhaustive literature was studied, and critical analysis was performed according to their phytochemical and pharmacological properties. Phytochemical investigations on different parts of M. vulgare have been reported the presence of flavonoids, steroids, terpenoids, tannins, saponins, and volatile oils (0.05%). The aerial parts contain marrubiin, together with ursolic acid and choline. Pharmacological activities such as antinociceptive, antispasmodic, antihypertensive, antidiabetic, gastroprotective, anti-inflammatory, antimicrobial, anticancer, antioxidant, and antihepatotoxic activity have been reported. M. vulgare has therapeutic potential in the treatment of inflammatory conditions, liver disorders, pain, cardiovascular, gastric, and diabetic conditions. Aerial parts of M. vulgare is a good source of labdane type diterpene especially marrubiin which is present in high concentrations. However, further scientific studies are needed to explore clinical efficacy, toxicity and to explore the therapeutic effect of major secondary metabolites such as diterpenes, phenylpropanoid, and phenylethanoid glycosides of M. vulgare.

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Premarrubiin. A diterpenoid from Marrubium vulgare L

Cited by 34 publications

References 0 publications

Biosynthesis of the labdane diterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway

Biosynthesis of the labdane diterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway

Marrubium vulgare (White Horehound): In Vitro Culture, and the Production of Diterpene Marrubiin and Other Secondary Metabolites

Marrubium vulgare L.: A review on phytochemical and pharmacological aspects

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