The isolation and structure of three new lignans from Justicia procumbens Linn. var. leucantha honda

Okigawa, Masayoshi; Maeda, Takako; Kawano, Nobusuke

doi:10.1016/s0040-4020(01)93074-1

Cited by 65 publications

(60 citation statements)

References 6 publications

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“…The NMR spectroscopic and spectrometric analyses were measured for compound 3 and all data taken together determined the structure of 3 as the arylnaphthalene lignanolide justicidin B, previously known from plants Justicia (Acanthaceae) [9,34] and Hoplophyllum (Rutaceae) [35] species and reported here for the first time from a microorganism. Water soluble compound 4 was isolated from the methanol extract of the mycelium, and the purification was achieved by column chromatography.…”

Section: Purification and Structure Elucidation Of The Active Compoundsmentioning

confidence: 73%

Novel Bioactive Metabolites from a Marine Derived Bacterium Nocardia sp. ALAA 2000

2008

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Extracts of the Egyptian marine actinomycete, Nocardia sp. ALAA 2000, were found to be highly bioactive. It was isolated from the marine red alga Laurenica spectabilis collected off the Ras-Gharib coast of the Red Sea, Egypt. According to detailed identification studies, the strain was classified as a member of the genus Nocardia. The cultivation and chemical analysis of this species yielded four structurally related compounds namely, chrysophanol 8-methyl ether (1), asphodelin; 4,7Ј-bichrysophanol (2) and justicidin B (3), in addition to a novel bioactive compound ayamycin; 1,1-dichloro-4-ethyl-5-(4-nitro-phenyl)-hexan-2-one (4) which is unique in contain both chlorination and a rarely observed nitro group. The compounds were isolated by a series of chromatographic steps and their structures of 1ϳ3 secured by detailed spectroscopic analysis of the MS and NMR data whereas that of 4 was elucidated by single crystal X-ray diffraction studies. These compounds displayed different potent antimicrobial activity against both Gram-positive and Gram-negative bacteria as well as fungi with MIC ranging from 0.1 to 10 mg/ml.

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Section: Purification and Structure Elucidation Of The Active Compoundsmentioning

confidence: 73%

Novel Bioactive Metabolites from a Marine Derived Bacterium Nocardia sp. ALAA 2000

2008

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“…32 The aglycone diphyllin (8) was generated by hydrolysis of phyllanthusmin C (4), and its structure was determined by comparison of its spectroscopic data with reference values. 12,35 All arylnaphthalene lignans isolated from P. poilanei in the present study and their semisynthetic analogues were evaluated for their cytotoxicity against HT-29 human colon cancer cells, using paclitaxel and etoposide as the positive controls (Table 3). 38 Compounds 1−4, 7, and 8 were found to be cytotoxic, of which 1 and 7 were the most potently active, with IC 50 values of 170 and 110 nM, respectively, but compounds 5, 6, and etoposide were inactive.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Potent cytotoxic arylnaphthalene lignan lactones from Phyllanthus poilanei

Ren¹,

Lantvit²,

Deng³

et al. 2014

Planta Med

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Two new (1 and 2) and four known arylnaphthalene lignan lactones (3−6) were isolated from different plant parts of Phyllanthus poilanei collected in Vietnam, with two further known analogues (7 and 8) being prepared from phyllanthusmin C (4). The structures of the new compounds were determined by interpretation of their spectroscopic data and by chemical methods, and the structure of phyllanthusmin D (1) was confirmed by single-crystal X-ray diffraction analysis. Several of these arylnaphthalene lignan lactones were cytotoxic toward HT-29 human colon cancer cells, with compounds 1 and 7-O- [(2,3,4- (7) found to be the most potent, exhibiting IC 50 values of 170 and 110 nM, respectively. Compound 1 showed activity when tested in an in vivo hollow fiber assay using HT-29 cells implanted in immunodeficient NCr nu/nu mice. Mechanistic studies showed that this compound mediated its cytotoxic effects by inducing tumor cell apoptosis through activation of caspase-3, but it did not inhibit DNA topoisomerase IIα activity. C ancer is a serious threat to human health, and the discovery and development of promising new agents to treat this condition is therefore an urgent need. Natural products and their semisynthetic derivatives are used widely in cancer chemotherapy.1,2 As an example, etoposide (VP-16) is a semisynthetic aryltetralin lignan lactone glycoside modeled on the natural product podophyllotoxin. It targets DNA topoisomerase II (topo II) and has been utilized for decades to treat several types of cancer.3 However, side effects have been reported for etoposide, including myelosuppression and the development of secondary leukemias linked to topo II inhibitory activity. 4 Thus, it is highly desirable to discover new agents to treat cancer showing diverse mechanisms of action.Etoposide is a semisynthetic epipodophyllotoxin glycoside derived from podophyllotoxin that is a naturally occurring aryltetralin lignan lactone containing four stereogenic centers at its C-7, -8, -7′, and -8′ positions. Podophyllotoxin is well known to occur in Podophyllum peltatum and P. emodi var. hexandrum (syn. Sinopodophyllum hexandrum) (Berberidaceae). 3,5,6 The latter plant has been found to contain both aryltetralin and arylnaphthalene lignan lactones. 7 In a manner different from aryltetralin lignan lactones, arylnaphthalene lignan lactones are based on a naphthalene unit rather than a tetrahydronaph-

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“…Me (767,768,769) RO (756), but an artefact formation during the extraction procedure, as initially assumed, has been ruled out by thorough investigations (757)(758)(759)(760).…”

Section: Arylnaphthalene Lignansmentioning

confidence: 98%

“…Justicidin C (318) and D (319) are identical to neojusticin Band A. One compound of type B ( 1-aryl-2,3-naphthalide lignans, Figs. H (797,768,798,775,776,799,BOO,779,772) Diphyllin (329) OH (801,802,803) (for further Refs., see text) sec ref.…”

Section: Arylnaphthalene Lignansmentioning

confidence: 99%

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Bringmann

Günther

Ochse

et al. 2001

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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The isolation and structure of three new lignans from Justicia procumbens Linn. var. leucantha honda

Cited by 65 publications

References 6 publications

Novel Bioactive Metabolites from a Marine Derived Bacterium Nocardia sp. ALAA 2000

Novel Bioactive Metabolites from a Marine Derived Bacterium Nocardia sp. ALAA 2000

Potent cytotoxic arylnaphthalene lignan lactones from Phyllanthus poilanei

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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