Cytotoxic and natural killer cell stimulatory constituents of Phyllanthus songboiensis

Ren, Yulin; Yuan, Chunhua; Deng, Youcai; Kanagasabai, Ragu; Ninh, Tran Ngoc; Tú, Vương Tân; Chai, Hee Byung; Soejarto, Djaja D.; Fuchs, James R.; Yalowich, Jack C.; Yu, Jianhua; Kinghorn, A. Douglas

doi:10.1016/j.phytochem.2014.12.014

Cited by 32 publications

(37 citation statements)

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“…These are the first report of topoisomerases I and II inhibitory activities of compounds 1-14 except that topoisomerase II inhibitory activity of 9, 10 and 12 were reported previously. [35][36][37] The cytotoxicity of all the compounds isolated were tested on selected human cancer cell lines, lung carcinoma (A549), ovary adenocarcinoma (SK-OV-3), liver hepatoblastoma (HepG-2) and colon adenocarcinoma (HT-29) cell lines ( Table 1) In conclusion, fourteen compounds including two new guaiane type sesquiterpenoids were isolated from the flowers of I. japonica. Structures of 1 and 2 were determined based on spectroscopic data.…”

Section: Resultsmentioning

confidence: 99%

DNA Topoisomerase Inhibitory Activity of Constituents from the Flowers of <i>Inula japonica</i>

Piao

Kim

Zhang

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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Key words Inula japonica; topoisomerase I; topoisomerase IIInula japonica THUNB. (Asteraceae) is a traditional herbal medicine and is widely distributed in Korea, Japan and China, and the flowers of this plant have been used to relieve phlegm, peptic disorder, inflammation and detumescence.1) Some terpenes 2-7) and flavonoids 8,9) have previously been isolated from this medicinal plant and have been reported to possess diverse biological activities, such as anti-diabetes, 10) antihypolipidemia, 11) hepatoprotective, 12) anti-inflammatory 7) and anti-tumor 1,2,13) effects. We have been isolating compounds that inhibited topoisomerases I and II from the source of medicinal plants. [14][15][16][17][18] DNA topoisomerases are enzymes that control DNA topology in the cell and are targets of anticancer drugs. 19,20) Topoisomerase I cleaves and reseals one DNA strand at a time and does not require ATP for the complementary strand to pass through the enzyme-linked strand break, thereby effecting DNA relaxation. Topoisomerase II cleaves both strands of DNA during catalysis. In a reaction coupled to ATP binding and hydrolysis, these proteins cleave one DNA duplex, transport a second duplex through the break, and then religate the cleaved duplex. 21) Camptothecin (CPT) and etoposide (VP-16) are typical inhibitors of topoisomerases I and II, respectively. 19) In this paper, we report isolation of fourteen compounds from the flowers of I. japonica and their DNA topoisomerases I and II inhibitory activities and cytotoxicities. Results and DiscussionTwo new (1, 2) and twelve known compounds (3-14) were isolated by various chromatographic separations from the EtOAc extract of the flowers of I. japonica (Fig. 1) C-NMR and distortionless enhancement by polarization transfer (DEPT) spectra of 1 showed seventeen peaks due to three methyl, four methylene, five methine and five quaternary carbons. The corresponding proton signals were determined by 1 H-detected heteronuclear multiple quantum coherence (HMQC) spectrum.The

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Section: Resultsmentioning

confidence: 99%

DNA Topoisomerase Inhibitory Activity of Constituents from the Flowers of <i>Inula japonica</i>

Piao

Kim

Zhang

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Analysis of the dichapetalin derivatives and their cytotoxic activity against cancer cell lines indicates that a methylenedioxy group connected at the C-3′ and C-4′ position is not required for this type of activity, but the presence of a hydroxy group at the C-22 position can enhance cytotoxicity. In addition, a primary C-26 hydroxy group seems to play a key role in determining the cytotoxic potency of the dichapetalin-type triterpenes [108,110]. These preliminary SAR conclusions indicate that the antitumor potential of the dichapetalins could be improved by synthetic modification.…”

Section: Dichapetalin-type Triterpenoidsmentioning

confidence: 83%

“…In a more recent investigation by our group, a non-cytotoxic dichapetalin A analogue, (+)-songbodichapetalin (38) (▶ Fig. 7), was isolated from the aerial parts of Phyllanthus songboiensis N. N. Thin (Phyllanthaceae) collected in Vietnam [110].…”

Section: Dichapetalin-type Triterpenoidsmentioning

confidence: 99%

Natural Product Triterpenoids and Their Semi-Synthetic Derivatives with Potential Anticancer Activity

Ren

Kinghorn

2019

Planta Med

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Triterpenoids are distributed widely in higher plants and are of interest because of their structural diversity and broad range of bioactivities. In particular, there is a very large literature on the propensity of a variety of triterpenoids to act as potential anticancer agents. In the present review, the anticancer potential is summarized for naturally occurring triterpenoids and their semi-synthetic derivatives, including examples of lupane-, oleanane-, ursane-, and cucurbitane-type pentacyclic triterpenoids, along with dammarane-type tetracyclic triterpenes including ginsenosides and their sapogenins and dichapetalins, which have been characterized as antitumor leads from higher plants. Preliminary structure-activity relationships and reported mechanisms of the antineoplastic-related activity are included. Prior studies for triterpenoids of plant origin are supportive of additional work being conducted on the more detailed biological and mechanistic evaluation for the progression of this type of natural products as possible cancer chemotherapeutic agents.

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“…Songbodichapetalin 375 is a new constituent of Phyllanthus songboiensis with cytotoxic activity. 139…”

Section: The Dammarane Groupmentioning

confidence: 99%

Triterpenoids

Hill

Connolly

2020

Nat. Prod. Rep.

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Cytotoxic and natural killer cell stimulatory constituents of Phyllanthus songboiensis

Cited by 32 publications

References 50 publications

DNA Topoisomerase Inhibitory Activity of Constituents from the Flowers of <i>Inula japonica</i>

DNA Topoisomerase Inhibitory Activity of Constituents from the Flowers of <i>Inula japonica</i>

Natural Product Triterpenoids and Their Semi-Synthetic Derivatives with Potential Anticancer Activity

Triterpenoids

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