α-Santalol derivatives from Santalum album and their cytotoxic activities

Matsuo, Yukiko; Mimaki, Yoshihiro

doi:10.1016/j.phytochem.2012.02.007

Cited by 24 publications

(19 citation statements)

References 13 publications

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“…α-santalol is known to prevent chemically-induced UVB induced skin carcinogenesis in various animal models [9-12]. α-santalol induced apoptosis in prostate cancer cells via activation of caspase-3 and PARP cleavage [13] and human promyelocytic leukemia HL-60 cells [14]. α- santalol induced G2/M phase cell cycle in human epidermoid carcinoma A431 cells and p53 wild-type human melanoma UACC-62 cells and up-regulated the expression of p21 and suppressed expressions of mutated p53 in A431 cells [15].…”

Section: Introductionmentioning

confidence: 99%

RETRACTED ARTICLE: α-santalol inhibits the angiogenesis and growth of human prostate tumor growth by targeting vascular endothelial growth factor receptor 2-mediated AKT/mTOR/P70S6K signaling pathway

2013

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BackgroundVEGF receptor 2 (VEGFR2) inhibitors, as efficient antiangiogenesis agents, have been applied in the cancer treatment. However, recently, most of these anticancer drugs have some adverse effects. Discovery of novel VEGFR2 inhibitors as anticancer drug candidates is still needed.MethodsWe used α-santalol and analyzed its inhibitory effects on human umbilical vein endothelial cells (HUVECs) and Prostate tumor cells (PC-3 or LNCaP) in vitro. Tumor xenografts in nude mice were used to examine the in vivo activity of α-santalol.Resultsα-santalol significantly inhibits HUVEC proliferation, migration, invasion, and tube formation. Western blot analysis indicated that α-santalol inhibited VEGF-induced phosphorylation of VEGFR2 kinase and the downstream protein kinases including AKT, ERK, FAK, Src, mTOR, and pS6K in HUVEC, PC-3 and LNCaP cells. α-santalol treatment inhibited ex vivo and in vivo angiogenesis as evident by rat aortic and sponge implant angiogenesis assay. α-santalol significantly reduced the volume and the weight of solid tumors in prostate xenograft mouse model. The antiangiogenic effect by CD31 immunohistochemical staining indicated that α-santalol inhibited tumorigenesis by targeting angiogenesis. Furthermore, α-santalol reduced the cell viability and induced apoptosis in PC-3 cells, which were correlated with the downregulation of AKT, mTOR and P70S6K expressions. Molecular docking simulation indicated that α-santalol form hydrogen bonds and aromatic interactions within the ATP-binding region of the VEGFR2 kinase unit.Conclusionα-santalol inhibits angiogenesis by targeting VEGFR2 regulated AKT/mTOR/P70S6K signaling pathway, and could be used as a potential drug candidate for cancer therapy.

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Section: Introductionmentioning

confidence: 99%

RETRACTED ARTICLE: α-santalol inhibits the angiogenesis and growth of human prostate tumor growth by targeting vascular endothelial growth factor receptor 2-mediated AKT/mTOR/P70S6K signaling pathway

2013

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“…Etoposide and cis- 14) the β-santalol derivative with an aldehyde group at the terminal side chain moiety (6) showed the most potent cytotoxic activities. In the neosandalnol skeleton (2-6 and 12), the introduction of an exomethylene group in the side chain (4-6) seem to contribute partially to the cytotoxicity, whereas hydrogenation of the double-bond in the side chain (3 and 7) decreased in the activity.…”

Section: Resultsmentioning

confidence: 99%

“…[9][10][11] However, β-santalol, another major volatile sesquiterpene from S. album with the same bicyclo[2.2.1] heptane skeleton, shows few biological activities, including anti-Helicobacter pylori 12) and antiviral effects. 13) We have reported that a methanolic extract of S. album heartwood exhibited cytotoxicity against HL-60 cells with an IC 50 value of 2.1 µg/mL and isolated new α-santalol derivatives 14) and lignans, 15) some of which induced apoptotic cell death in HL-60 and A549 cells. These results prompted us to investigate the heartwood of S. album further.…”

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confidence: 98%

A Rare Type of Sesquiterpene and β-Santalol Derivatives from <i>Santalum album</i> and Their Cytotoxic Activities

2014

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A rare type of sesquiterpene with a spiro bicyclic system (1) and seven new (2-8) and four known (9-12) β -santalol derivatives were isolated from the heartwood of Santalum album (Santalaceae). The structures of these new compounds were determined by analysis of extensive spectroscopic data. The isolated compounds and derivatives were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, HSC-2 and HSC-4 human oral squamous cell carcinoma cell lines, and TIG-3 normal human diploid fibroblasts. cis-β -Santalol (9) and β -santaldiol (10) induced apoptotic cell death in HL-60 cells.

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“…Research on the components of S . album has focused on the search for new compounds, and the detailed analysis of the essential oil, etc. Studies have shown the activities of S .…”

Section: Introductionmentioning

confidence: 99%

“…There are many research reports about Santalum album L. (sandalwood). Research on the components of S. album has focused on the search for new compounds, [1][2][3] and the detailed analysis of the essential oil, [3,4] etc. Studies have shown the activities of S. album include antimicrobial and repellent effects against acari, [5,6] and chemopreventative effects on skin papillomas, [7] etc.…”

Section: Introductionmentioning

confidence: 99%

Prolonged anxiolytic‐like activity of sandalwood (Santalum album L.) oil in stress‐loaded mice

Satou

Miyagawa

Seimiya

et al. 2013

Flavour & Fragrance J

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The fragrance of Santalum album L. (sandalwood) has been used as a sedative. However, few reports have investigated the anxiolytic activity of sandalwood fragrance. Therefore, in this study, we examined the anxiolytic-like activity of hexane-extracted sandalwood oil (SAO). Male ICR mice, aged 5 weeks at the start of each experiment, were used. To mimic its clinical use, the effect of SAO after stress loading was investigated. Mice were individually housed in cages for 1 week and subjected to loaded water-immersion stress for 24 h. Next, SAO inhalation (i.h.) was initiated 90 min prior to the elevated plus maze (EPM) test. As a result, significant anxiolytic-like activity was observed at 4 μl/l air SAO i.h. In contrast, anxiolytic-like activity was not observed in non-stressed control mice. Additionally, mice were subjected to SAO i.h prior to water-immersion stress for 24 h in order to investigate its prolonged effect. As a result, significant anxiolytic-like activity was observed at 4 μl/l air SAO i.h. In contrast, anxiolytic-like activity was not observed in non-stressed control mice. The above results indicate that the anxiolytic-like activity of SAO i.h. is revealed under stress conditions and is prolonged for at least 24 h. Since the main components of SAO are (Z)-α-santalol (51.1%) and (Z)-β-santalol (28.5%), it is proposed that they are involved in mediating the characteristic anxiolytic-like activity of SAO.

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α-Santalol derivatives from Santalum album and their cytotoxic activities

Cited by 24 publications

References 13 publications

RETRACTED ARTICLE: α-santalol inhibits the angiogenesis and growth of human prostate tumor growth by targeting vascular endothelial growth factor receptor 2-mediated AKT/mTOR/P70S6K signaling pathway

RETRACTED ARTICLE: α-santalol inhibits the angiogenesis and growth of human prostate tumor growth by targeting vascular endothelial growth factor receptor 2-mediated AKT/mTOR/P70S6K signaling pathway

A Rare Type of Sesquiterpene and β-Santalol Derivatives from <i>Santalum album</i> and Their Cytotoxic Activities

Prolonged anxiolytic‐like activity of sandalwood (Santalum album L.) oil in stress‐loaded mice

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