ChemInform Abstract: Diterpenoids from the Japanese Liverwort Jungermannia infusca.

Nagashima, Fumihiro; Takaoka, Shigeru; Asakawa, Yoshinori

doi:10.1002/chin.199902190

Cited by 4 publications

(5 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Purification and structural characterization of both compounds by NMR (Figs S20 – S23 and Tables S6 & S7) revealed that SsSS removes the diphosphate and forms a tertiary alcohol, ent -kolavelool ( 35 )(Soares et al, 2014), while KgTS removes the diphosphate and forms an additional carbon-carbon double bond, producing the exo -methylene containing (5 R ,8 R ,9 S ,10 R )-cleroda-3,13(16),14-triene ( 36 ), which has been previously observed (Nagashima et al, 1998). Notably, SsSS and KgTS also readily react with kolavenyl diphosphate ( 13 ) resulting in enantiomeric products to those observed with 12 , as indicated by their identical retention times and mass spectra upon non-chiral GC-MS analysis (Fig.…”

Section: Resultssupporting

confidence: 53%

Extreme promiscuity of a bacterial and a plant diterpene synthase enables combinatorial biosynthesis

Jia

Potter

Peters

2016

Metabolic Engineering

View full text Add to dashboard Cite

Diterpenes are widely distributed across many biological kingdoms, where they serve a diverse range of physiological functions, and some have significant industrial utility. Their biosynthesis involves class I diterpene synthases (DTSs), whose activity can be preceded by that of class II diterpene cyclases (DTCs). Here, a modular metabolic engineering system was used to examine the promiscuity of DTSs. Strikingly, both a bacterial and plant DTS were found to exhibit extreme promiscuity, reacting with all available precursors with orthogonal activity, producing an olefin or hydroxyl group, respectively. Such DTS promiscuity enables combinatorial biosynthesis, with remarkably high yields for these unoptimized non-native enzymatic combinations (up to 15 mg/L). Indeed, it was possible to readily characterize the 13 unknown products. Notably, 16 of the observed diterpenes were previously inaccessible, and these results provide biosynthetic routes that are further expected to enable assembly of more extended pathways to produce additionally elaborated ‘non-natural’ diterpenoids.

show abstract

Section: Resultssupporting

confidence: 53%

Extreme promiscuity of a bacterial and a plant diterpene synthase enables combinatorial biosynthesis

Jia

Potter

Peters

2016

Metabolic Engineering

View full text Add to dashboard Cite

show abstract

“…Systematic column chromatography fractionation of hexane and CH 2 Cl 2 extracts from the aerial parts of C. pulchella lead to the isolation of the furanoid ent-clerodanes (À)-hardwikiic acid (1) (Misra et al, 1979), methyl (À)-hardwikiate (2) (Misra et al, 1979), (À)-hautriwaic acid lactone (3) (Bohlmann and Grenz, 1972;Hsü et al, 1971), methyl (À)-nidoresedate (4) (Pandey et al, 1984), methyl (À)-strictate (5) (Tandon and Rastogi, 1979;Pandey et al, 1984), together with (+)-(13E)-labd-13-ene-8,15-diol (6) (Nagashima et al, 1998;Forster et al, 1985), and (+)-isoabienol (7) (Nagashima et al, 1998;Cabrera et al, 1983). In addition, bcaryophyllene oxide (Krebs et al, 1990), sphatulenol (Tinto et al, 1992), eudesm-4(15)-en-1b,6a-diol (Sun et al, 2004), lupeoyl stearate (Razdan et al, 1996), a-amyrin and b-amyrin stearates (Mendes et al, 1999), b-sitosterol 3-O-b-D-glucoside (Ahmad et al, 2003), stigmasterol 3-O-b-D-glucoside (Ahmad et al, 2003), bsitosterol, stigmasterol and stigmastenol were also isolated from this source.…”

Section: Resultsmentioning

confidence: 99%

“…Clerodanes and labdanes with related structures are often isolated from the same organism, since it is considered that the clerodane skeleton biogenetically derives from a labdane via series of methyl and hydride shifts (Dewick, 2009). In some cases, a species can elaborate both the normal labdane-type and the ent-clerodane-type (neoclerodane) diterpenoids (Nagashima et al, 1998;Rijo et al, 2002). It is also of interest that cis and trans ent-clerodane compounds are known (Merritt and Ley, 1992) and that the stereochemistry of some furanoid ent-clerodanes has been revised (Pandey et al, 1984).…”

Section: Introductionmentioning

confidence: 99%

Absolute configuration of labdanes and ent-clerodanes from Chromolaena pulchella by vibrational circular dichroism

et al. 2011

View full text Add to dashboard Cite

“…cordifolia [101] , Jungermannia rotundata [102] , Jungermannia hattoriana [103] , Jungermannia infusca [104][105][106] , Jungermannia subulata (cell suspension culture) [107] , Jackiella javanica [108,109] , Pellia endiviifolia [110] , P. perrottetiana [111] , …”

Section: Diterpenoidsmentioning

confidence: 99%

Therapeutic potential of bryophytes and derived compounds against cancer

Dey

Mukherjee²

2015

Journal of Acute Disease

View full text Add to dashboard Cite

A B S T R A C TObjective: Bryophytes, taxonomically placed between the algae and the pteridophytes, are divided into three classes such as Liverworts, Hornworts and Mosses. Indigenous use involves this small group of plants to treat various diseases. Bryophytes have been investigated pharmacologically for active biomolecules. Several constituents with therapeutic potential have been isolated, characterized and investigated for antibacterial, antifungal, antiviral, antioxidative, antiinflamatory and anticancerous efficacy. Methods: The present review deals with the literature covering the anticancerous potential of bryophytes. Apart from the examples of the compounds and the containing bryophyte genera, the authors have tried to include the examples of cancer cell lines on which the efficacy have been tested and the mode of action of certain cytotoxic agents. Results: Crude extracts and isolated compounds from bryophytes were found to possess potent cytotoxic properties. Different types of terpenoids and bibenzyls have been reported among the most potent cytotoxic compounds. Most of these compounds were found to induce apoptosis by activating a number of genes and enzymes. Biochemical markers such as DNA fragmentation, nuclear condensation, proteolysis of poly (ADPribose) polymerase, activation of caspases, inhibition of antiapoptotic nuclear transcriptional factor-kappaB, activation of p38 mitogen-activated protein kinase etc. have been found to be associated with apoptotic and necrotic response. Conclusions: This review summarizes recent scientific findings and suggests further investigations to evaluate the cytotoxic efficacy of bryophytes.

show abstract

ChemInform Abstract: Diterpenoids from the Japanese Liverwort Jungermannia infusca.

Cited by 4 publications

References 1 publication

Extreme promiscuity of a bacterial and a plant diterpene synthase enables combinatorial biosynthesis

Extreme promiscuity of a bacterial and a plant diterpene synthase enables combinatorial biosynthesis

Absolute configuration of labdanes and ent-clerodanes from Chromolaena pulchella by vibrational circular dichroism

Therapeutic potential of bryophytes and derived compounds against cancer

Contact Info

Product

Resources

About