Protoberberine Alkaloids and Cancer Chemopreventive Properties of Compounds from <i>Alangium salviifolium</i>

Pailee, Phanruethai; Prachyawarakorn, Vilailak; Mahidol, Chulabhorn; Ruchirawat, Somsak; Kittakoop, Prasat

doi:10.1002/ejoc.201100423

Cited by 29 publications

(34 citation statements)

References 25 publications

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“…The structures of all synthetic compounds were supported by 1 H and 13 C NMR spectra, and by mass spectra. The physical and spectroscopic data for our synthetic alangiumkaloid A ( 1 ) and B ( 2 ) are consistent with those for natural alangiumkaloids A ( 1 ) and B ( 2 ) in all respects …”

Section: Resultssupporting

confidence: 81%

“…Two 8-oxoprotoberberine alkaloids, alangiumkaloids A (1) and B (2), were isolated from Alangium salviiforlium by Kittakoop and co-workers in 2011 ( Figure 1). [1] The cytotoxic activity of 1 and 2 along with that of other alangiumkaloids was evaluated against four cancer cell lines: MOLT-3, HepG2, A549, and HuCCA-1. Alangiumkaloid A (1) was reported to exhibit weak cytotoxic activity toward the MOLT-3 cancer cell line (IC 50 13.0 μM).…”

Section: Introductionmentioning

confidence: 99%

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Total Synthesis of Two 8‐Oxoprotoberberine Alkaloids: Alangiumkaloids A and B

et al. 2018

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A new and versatile synthetic route for 8‐oxoprotoberberine 17 through synthesis of isoquinolinone 16 and construction of a B‐ring is described. The key step is the synthesis of isoquinolinone 14 through thermal cyclization of 2‐alkynylbenzaldehyde oxime 12 to afford isoquinoline N‐oxide 13, followed by a Reissert–Henze‐type reaction. The first total synthesis of 8‐oxoprotoberberine alkaloid alangiumkaloids A and B was achieved by using this strategy.

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Section: Resultssupporting

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Two 8‐Oxoprotoberberine Alkaloids: Alangiumkaloids A and B

et al. 2018

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“…Biologically active ingredients of A. salvifolium include flavinoids, glycosides, alkaloids and saponins 19,20 . Nine protoberberine alkaloids have been isolated from A. salviifolium, among which, 27-O-trans-caffeoylcylicodiscic acid (3) and myriceric acid B (4) exhibited cytotoxic activity towards the MOLT-3 cell line, while 3-O-demethyl-2-O-methylalangiside (5) selectively inhibited the growth of the HepG2 cancer cell line 21 .…”

Section: Alangium Salviifoliummentioning

confidence: 99%

Anti-cancer potential of South Asian plants

Rahman

2013

Nat. Prod. Bioprospect.

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Phyto-chemicals are increasingly being used in the treatment of cancer because of their availability, potential anti-cancer activity with less adverse effects when compared with chemotherapy. The variation of climate and geography in South Asian countries provides a nursing environment for the growth of versatile plant species, that are repeatedly drawing attention of the scientific community. In this review, we have focused on the anti-cancer potential of thirty plants, which are commonly found in Bangladesh, India, Nepal, Pakistan and Sri Lanka, with their mechanisms of action. In particular, we have discussed the bio-active components that display anti-cancer activity, which have been identified in these plants. This review may help researchers to profile plants with known anti-cancer effect of this region and further investigations of anti-cancer agents in medicinal plants from South Asia.

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“…Alangiside, on the other hand, was devoid of significant cytotoxicity against any of the cell lines tested, as demonstrated by GI 50 values higher than 45.74 μM. An earlier report had shown this alkaloid to be inactive against MOLT-3, HepG2, A549, and HuCCA-1 cancer cell lines (Pailee, Prachyawarakorn, Mahidol, Ruchirawat, & Kittakoop, 2011), which confirms the low anticancer potential of alangiside.…”

Section: Caspase-3 Activity Assaymentioning

confidence: 56%

Cytotoxic alkaloids from Pogonopus tubulosus: G2/M cell cycle arrest and inhibition of DNA topoisomerase IIα by isotubulosine

Filippin

Portela

Rodrigues

et al. 2018

Phytotherapy Research

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Phytochemical investigation of Pogonopus tubulosus trunk led to the isolation of isotubulosine and alangiside, tetrahydroisoquinoline indolic monoterpene alkaloids reported here for the first time for the family Rubiaceae and the genus Pogonopus, respectively. Isotubulosine proved cytotoxic against MCF‐7, PC‐3, 786‐0, HT‐29, and HL‐60 human cancer cell lines, with GI50 values ranging from 5.26 to 20.61 μM, in addition to causing G2/M arrest, possibly by inhibiting DNA topoisomerase IIα. Alangiside showed weak cytotoxicity against MCF‐7 and HL‐60 and proved inactive against PC‐3, HT‐29, and 786‐0 cell lines, with no sign of apoptosis. The alkaloid structures were established on the basis of 1D‐ and/or 2D‐NMR, optical rotation, and HR ESIMS data. Complete 1H NMR assignments of isotubulosine were also performed, using 1H‐1H COSY, HSQC, HMBC, NOESY, and 1H J‐resolved techniques and employing experimental and calculated values of homonuclear coupling constants based on the lowest energy conformations. The foregoing results provide new information on the cytotoxicity and mechanism of action of tetrahydroisoquinoline indole monoterpene‐type alkaloids and reveal isotubulosine to merit further studies as a potential anticancer agent.

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Protoberberine Alkaloids and Cancer Chemopreventive Properties of Compounds from Alangium salviifolium

Cited by 29 publications

References 25 publications

Total Synthesis of Two 8‐Oxoprotoberberine Alkaloids: Alangiumkaloids A and B

Total Synthesis of Two 8‐Oxoprotoberberine Alkaloids: Alangiumkaloids A and B

Anti-cancer potential of South Asian plants

Cytotoxic alkaloids from Pogonopus tubulosus: G2/M cell cycle arrest and inhibition of DNA topoisomerase IIα by isotubulosine

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