Cytotoxic Arylnaphthalene Lignans from Phyllanthus oligospermus

Wu, Shwu Jen; Wu, Tian Shung

doi:10.1248/cpb.54.1223

Cited by 35 publications

(33 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An L-arabinopyranosyl residue of 1 could be proposed based on the several lines of evidence that follow. First, both the NOESY correlations and the specific rotation value of 1 were consistent with those of the known compound 3, as reported 22 and isolated in the present study. Second, the NOESY correlations and specific rotation value of 1 were consistent with those determined for 4 (phyllanthusmin C) in this investigation.…”

Section: ■ Results and Discussionsupporting

confidence: 89%

“…When the cytotoxic CHCl 3 partitions were subjected to chromatographic separation guided by inhibitory activity against the HT-29 cell line, two new [phyllanthusmins D (1) and E (2)] and four known [phyllanthusmins A (6), 22 B (3), 22 and C (4) 22 and cleistanthin B (5) 26 ] arylnaphthalene lignan lactones were purified. The various plant collections and the compounds isolated from each collection are summarized in Table 1.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Thus, compound 1 was proposed as an O-acetyl analogue of the known compounds phyllanthusmins B (3) and C (4), with both being characterized from Phyllanthus oligospermus in a previous study. 22 Comparison of the NMR data of compound 1 with those of phyllanthusmins B (3) and C (4) ( Table 2 and Tables S1 and S2, Supporting Information) showed that these compounds displayed closely similar NMR resonances for the diphyllin aglycone unit but different resonances for their saccharide portions. An L-arabinopyranosyl residue of 1 could be proposed based on the several lines of evidence that follow.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…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-Phyllanthus acutissima, 19 P. myrtifolius, 20,21 P. oligospermus, 22 P. piscatorum, 23 and P. taxodiifolius; 24 and the Rutaceae, from Haplophyllum cappadocicum, 25 H. buxbaumii, 26,27 H. dauricum, 28 and H. patavinum.…”

mentioning

confidence: 99%

“…9,10,16,19,22,24,30,31 For example, justicidin A (a methylated diphyllin derivative) isolated from Justicia ciliata showed cytotoxicity toward several human cancer cell lines with IC 50 values in the range 2−7 ng/mL. 9 Justicidin B, a dehydroxylated diphyllin, was cytotoxic toward SKW-3 chronic lymphoid leukemia cells.…”

mentioning

confidence: 99%

See 4 more Smart Citations

Potent cytotoxic arylnaphthalene lignan lactones from Phyllanthus poilanei

Ren¹,

Lantvit²,

Deng³

et al. 2014

Planta Med

View full text Add to dashboard Cite

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-

show abstract

Section: ■ Results and Discussionsupporting

confidence: 89%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

Potent cytotoxic arylnaphthalene lignan lactones from Phyllanthus poilanei

Ren¹,

Lantvit²,

Deng³

et al. 2014

Planta Med

View full text Add to dashboard Cite

show abstract

Biological Properties of Lignans

Calvo‐Flores

Dobado

Isac‐García

et al. 2015

Lignin and Lignans as Renewable Raw Materials

View full text Add to dashboard Cite

New Lignans and Their Biological Activities

Zhang

Chen

Liang

et al. 2014

Chemistry & Biodiversity

View full text Add to dashboard Cite

Lignans, which are widely distributed in higher plants, represent a vast and rather diverse group of phenylpropane derivatives. They have attracted considerable attention due to their pharmacological activities. Some of the lignans have been developed approved therapeutics, and others are considered as lead structures for new drugs. This article is based on our previous review of lignans discovered in the period 2000-2004, and it provides a comprehensive compilation of the 354 new naturally occurring lignans obtained from 61 plant families between 2005 and 2011. We classified five main types according to their structural features, and provided the details of their sources, some typical structures, and diverse biological activities. A tabular compilation of the novel lignans by species is presented at the end. A total of 144 references were considered for this review.

show abstract

Cytotoxic Arylnaphthalene Lignans from Phyllanthus oligospermus

Cited by 35 publications

References 19 publications

Potent cytotoxic arylnaphthalene lignan lactones from Phyllanthus poilanei

Potent cytotoxic arylnaphthalene lignan lactones from Phyllanthus poilanei

Biological Properties of Lignans

New Lignans and Their Biological Activities

Contact Info

Product

Resources

About