Naturally occurring benzofuran: isolation, structure elucidation and total synthesis of 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[b]furancarbaldehyde, a novel adenosine A1 receptor ligand isolated from salvia miltiorrhiza bunge (danshen)

Yang, Zhen; Hon, Po‐Ming; Chui, Kuk Ying; Xu, Zun Le; Chang, Hua Hua; Lee, Chi-Ming; Cui, Yu Xin; Wong, H. N. C.; Poon, Chi Duen; Fung, B. M.

doi:10.1016/s0040-4039(00)78908-8

Cited by 68 publications

(65 citation statements)

References 13 publications

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“…The product was reprotected with a benzyl group, treated with diisobutyl aluminum hydride in dry tetrahydrofuran, selective-oxidized with manganese dioxide in ethyl acetate, and then finally deprotected with titanium tetrachloride in dichloromethane to obtain the target molecule as a yellowish solid. The desired product was confirmed by 1 H NMR and electron ionization/mass spectrometry and gave spectral data identical with literature values (Yang et al, 1991(Yang et al, , 1992Kuo and Wu, 1996) Cell Lines. Human oral epidermoid carcinoma KB cells, nasopharyngeal carcinoma HONE-1 cells, colorectal carcinoma HT29 cells, nonsmall cell lung cancer H460 cells, and glioblastoma multiforme DBTRG cells were maintained in RPMI 1640 medium supplied with 5% fetal bovine serum.…”

Section: Methodssupporting

confidence: 73%

Salvinal, a Novel Microtubule Inhibitor Isolated from Salvia miltiorrhizae Bunge (Danshen), with Antimitotic Activity in Multidrug-Sensitive and -Resistant Human Tumor Cells

Chang

Kuo

et al. 2004

Mol Pharmacol

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Aqueous extracts of Salvia miltiorrhizae Bunge have been extensively used in the treatment of cardiovascular disorders and cancer in Asia. Recently, a compound, 5-(3-hydroxypropyl)-7-methoxy-2-(3Ј-methoxy-4Ј-hydroxyphenyl)-3-benzo[b]furancarbaldehyde (salvinal), isolated from this plant showed inhibitory activity against tumor cell growth and induced apoptosis in human cancer cells. In the present study, we investigated the cytotoxic effect and mechanisms of action of salvinal in human cancer cell lines. Salvinal caused inhibition of cell growth (IC 50 range, 4 -17 M) in a variety of human cancer cell lines. Flow cytometry analysis showed that salvinal treatment resulted in a concentration-dependent accumulation of cells in the G 2 /M phase. We observed, using Hoechst 33258 dye staining, that salvinal blocked the cell cycle in mitosis. In vitro and in vivo examinations showed that salvinal inhibited tubulin polymerization in a concentration-dependent manner. Immunocytochemical studies demonstrated that salvinal treatment caused the changes of cellular microtubule network, similar to the effect of colchicine. In addition, salvinal treatment resulted in upregulation of cyclin B1 levels, activation of Cdc2 kinase, and Cdc25c phosphorylation. Furthermore, elevation of levels of MPM-2 phosphoepitopes in salvinal-treated cells in a concentration-dependent manner was also observed. Similar to the effect of other antitubulin agent, hyperphosphorylation of Bcl-2, induction of DNA fragmentation and activation of caspase-3 activity occurred in salvinal-treated cells. In particular, salvinal exhibited similar inhibitory activity against parental KB, Pglycoprotein-overexpressing KB vin10 and KB taxol-50 cells, and multidrug resistance-associated protein (MRP)-expressing etoposide-resistant KB 7D cells. Taken together, our data demonstrate that salvinal inhibits tubulin polymerization, arrests cell cycle at mitosis, and induces apoptosis. Notably, Salvinal is a poor substrate for transport by P-glycoprotein and MRP. Salvinal may be useful in the treatment of human cancers, particularly in patients with drug resistance.

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Section: Methodssupporting

confidence: 73%

Salvinal, a Novel Microtubule Inhibitor Isolated from Salvia miltiorrhizae Bunge (Danshen), with Antimitotic Activity in Multidrug-Sensitive and -Resistant Human Tumor Cells

Chang

Kuo

et al. 2004

Mol Pharmacol

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“…Whether extracting the effective fractions or a single compound, the most salient example is that of the research team at Hong Kong Chinese University, who isolated 1 mg of XH-14 [52] from 10 kg of raw Danshen. Of course, its bioactivity is also the property which attracted the chemists' attention.…”

Section: Preparative Methodsmentioning

confidence: 99%

“…Because it was initially isolated from the tissue culture medium of Danshen and its content in culture medium showed a dynamic change, it was (42)(43)(44)(45)(46)(47)(48)(49)(50)(51)(52)(53) speculated that it is related to the biosynthesis of cryptotanshinone. Compounds related to ferrugiol are 2-hydroxyferrugiol (51), sugiol (52) [22] and arucadiol (53) [31]. In fact, arucadiol is the same compound as miltiodiol, which was isolated by Kakisawa in early years.…”

Section: Compounds Related To Biogenesis Of Tanshinonementioning

confidence: 99%

“…They received attention because of their strongly inhibitory effect on aldose reductase, with an IC 50 of 0.014 and 0.042, respectively. Demethylcryptojaponol (58) [34] is very similar in structure to sugiol (52) and thus may be a transformed product of the latter. To avoid the occurrence of artifact products (for example, the above 1-hydroxytanshinone IIA was demonstrated to be an artifact product) during extraction of Danshen, some research teams in Japan emphasized that the fresh Danshen roots should be soaked immediately in methanol to avoid the production of artifact products.…”

Section: Other Compoundsmentioning

confidence: 99%

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Liposoluble Chemical Constituents in Danshen

Luo

2014

Dan Shen (Salvia Miltiorrhiza) in Medicine

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“…Danshen (Salvia miltiorrhiza Bunge) is used in traditional Chinese medicine for the treatment of diseases related to blood flow (13,14). Phytochemical analysis of Danshen plant has led to the isolation of a large number of compounds.…”

Section: Introductionmentioning

confidence: 99%

Tanshinone II is a potent candidate for treatment of lipopolysaccharide-induced acute lung injury in rat model

Zhang

Tan

et al. 2017

Oncol Lett

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Abstract. The present study aimed to investigate the effect of tanshinone II, isolated from Salvia miltiorrhiza Bunge, on lipopolysaccharide (LPS)-induced acute lung injury (ALI) in rats. Male Sprague-Dawley rats were divided into three groups: Control, LPS and tanshinone II. Animals in the tanshinone II and LPS groups were administered 10 mg/kg LPS, whereas those in the control group received an equal volume of normal saline. Tanshinone II treatment group were injected with 30 nm/kg tanshinone II at 1 h after LPS administration. The results revealed that LPS administration increased the bronchoalveolar lavage fluid protein concentration significantly compared with the control group. However, tanshinone II treatment significantly inhibited the LPS-induced increase in protein level. Treatment of the LPS-administered rats with tanshinone II prevented the formation of pulmonary edema, which was evidenced by low values for wet to dry lung weight ratio. The activity of myeloperoxidase and expression of malondialdehyde were significantly lower in lung homogenates from the tanshinone II group compared with the LPS group. Furthermore, tanshinone II treatment inhibited the expression of tumor necrosis factor-α and interleukin-6 in the blood plasma. Tissue sections of the tanshinone II group exhibited normal morphology and absence of neutrophil accumulation. However, in the LPS group, neutrophils accumulated and penetrated into the pulmonary tissues. These results suggested that tanshinone II protects the rats from LPS-induced ALI. Therefore tanshinone II may have clinical applications in the treatment of ALI.

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Naturally occurring benzofuran: isolation, structure elucidation and total synthesis of 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[b]furancarbaldehyde, a novel adenosine A1 receptor ligand isolated from salvia miltiorrhiza bunge (danshen)

Cited by 68 publications

References 13 publications

Salvinal, a Novel Microtubule Inhibitor Isolated from Salvia miltiorrhizae Bunge (Danshen), with Antimitotic Activity in Multidrug-Sensitive and -Resistant Human Tumor Cells

Salvinal, a Novel Microtubule Inhibitor Isolated from Salvia miltiorrhizae Bunge (Danshen), with Antimitotic Activity in Multidrug-Sensitive and -Resistant Human Tumor Cells

Liposoluble Chemical Constituents in Danshen

Tanshinone II is a potent candidate for treatment of lipopolysaccharide-induced acute lung injury in rat model

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