Structures of isotanshinones

Kakisawa, Hiroshi; Hayashi, Teruo; Yamazaki, Takahiro

doi:10.1016/s0040-4039(01)87676-0

Cited by 45 publications

(31 citation statements)

References 6 publications

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“…This group is characterized by 1,4 pquinone. Of these nine royleanone tanshinones, besides six isotanshinones, there are also the paraquinone compounds with an enolic group in (27)(28)(29)(30)(31)(32) ring C, e.g., danshenxinkun A, danshenxinkun B, and danshenxinkun C [13]. Danshenxinkun also belongs to the royleanone type of 1,4 p-quinone.…”

Section: Royleanone Tanshinonementioning

confidence: 99%

“…In the royleanone tanshinones, there are also six isotanshinones in very low content; they are isotanshinone I (33), isotanshinone IIA (34), isocryptotanshinone (35) [28], isodihydrotanshinone I (36) [29], iso-2-hydroxy dihydrotanshinone I (37) [21], and isotanshinone IIB (38) [30], of which only a few compounds have been tested for their bioactivities. For example, isotanshinone IIB has an inhibitory effect on platelet aggregation induced by ADP and collagen.…”

Section: Royleanone Tanshinonementioning

confidence: 99%

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Liposoluble Chemical Constituents in Danshen

Luo

2014

Dan Shen (Salvia Miltiorrhiza) in Medicine

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Section: Royleanone Tanshinonementioning

confidence: 99%

Section: Royleanone Tanshinonementioning

confidence: 99%

Liposoluble Chemical Constituents in Danshen

Luo

2014

Dan Shen (Salvia Miltiorrhiza) in Medicine

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“…The isolated compounds were identified as isotanshinone IIA (1), dihydroisotanshinone I (2), and isocryptotanshinone (3) by analysis of NMR and MS data, together with comparison of their spectral data with those in the literature. [20][21][22] Compounds 1-3 inhibited the hydrolysis of the pNPP catalyzed by PTP1B in a dose-dependent manner with IC 50 values of 11.4Ϯ0.6 mM, 22.4Ϯ 0.6 mM and 56.1Ϯ6.3 mM, respectively (Table 1). A known phosphatase inhibitor, RK-682, was employed as a positive control.…”

Section: Resultsmentioning

confidence: 99%

PTP1B Inhibitory Effect of Abietane Diterpenes Isolated from Salvia miltiorrhiza

Han

et al. 2005

Biological & Pharmaceutical Bulletin

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The reversible protein tyrosine phosphorylation by protein tyrosine kinases (PTK) and protein tyrosine phosphatases (PTP) is a key element of the signaling pathways induced by environmental stimuli.1,2) One of the intracellular PTPases, protein tyrosine phosphatase 1B (PTP1B) has been implicated in the negative regulation of insulin signaling by dephosphorylating the insulin receptor (IR) as well as its substrate, insulin receptor substrate-1 (IRS-1) and insulin receptor substrate-2 (IRS-2).3-5) The protein levels are increased in insulin-resistant diabetes patients and the deletion of PTP1B in mice has been shown to increase insulin sensitivity.6-8) Thus, inhibiting PTP1B action by using antisense oligonucleotides or small molecule inhibitors represents one of the novel therapeutic approaches for the treatment of insulin resistance.9,10) There have been a number of reports on the designing and development of synthetic PTP1B inhibitors, 11) and several classes of plant-derived secondary metabolites have been described as PTP1B inhibitors. 12)The dried root of Salvia miltiorrhiza BUNGE (Labiatae), called 'Danshen' in China, is one of the most popular traditional Chinese medicines. This plant has been used for the treatment of various diseases such as menstrual disorder, menorrhalgia, insomnia, blood circulation diseases, angina pectoris, and inflammation. Particularly, the drug is valuable in the treatment of coronary heart diseases.13) The major constituents in the root of S. miltiorrhiza are abietane-type diterpene pigments, so called tanshinones, which have ortho-or para-naphthoquinone chromophores. 14) They are unique components found in the Salvia genus and many of them exhibit diverse biological activities. [15][16][17][18] In the study, the MeOH extract of the dried root of S. miltiorrhiza displayed significant PTP1B inhibitory effect and the further study was conducted to isolate and identify the active principles. MATERIALS AND METHODS Plant MaterialsThe dried roots of S. miltiorrhiza were purchased from Il-sin Pharmaceutical Co., Ltd. in Daejeon, Korea. A voucher specimen (no. 162) has been deposited in the author's laboratory.Extraction and Isolation The dried roots of S. miltiorrhiza (1 kg) were extracted with MeOH (4 l) for 24 h. A portion (300 ml) of the resulting MeOH extract was concentrated. The dried extract (2.64 g) was subjected to silica gel column chromatography (Merck Kieselgel 60; 100 g; 0.015-0.040 mm particle size; 4.5ϫ18.5 cm). The column was eluted with a gradient consisting of hexane-EtOAc (95 : 5, 1800 ml; 93 : 7, 400 ml; 90 : 10, 400 ml; 80 : 20, 400 ml; 70 : 30, 200 ml; 50 : 50, 200 ml; 40 : 60, 200 ml; 20 : 80, 200 ml; 100% EtOAc 200 ml; collecting 200 ml fraction) and 200 ml; 80 : 20, 200 ml; 70 : 30, 200 ml; collecting 200 ml fraction). Fractions of similar composition as determined by TLC analysis were pooled, affording 11 fractions (fr. 1-11). Fr. 2 (23 mg, eluted between 700 to 800 ml) yielded 1 (4.6 mg) by preparative reversed phase HPLC using a gradient from 60 to 100% C...

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“…It is used widely in a clinical setting in China for dilating blood vessels and improving blood flow (Wang et al, 1978;Microcirculation Group, 1978;Onitsuka et al, 1983;Chen, 1984). Salviae Miltiorrhizae Radix has been reported to contain naphthoquinone derivatives as its active components (Kakisawa et af., 1968;Inouye and Kakisawa, 1969;Kakisawa et al, 1969;Shibata et al, 1982).…”

Section: Introductionmentioning

confidence: 99%

Effects on blood pressure of caffeic acid analogues isolated from Salviae Miltiorrhizae Radix in rats with adenine‐induced renal hypertension

Yokozawa

Zhou

Oura

et al. 1995

Phytotherapy Research

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The effects of caffeic acid analogues isolated from Salviae Miltiorrhizae Radix were examined in rats with adenine-induced renal failure and hypertension. Systolic, mean and diastolic blood pressures were decreased after magnesium lithospermate B administration. Oral administration of lithospermic acid B also decreased these blood pressure values even though the effects were weaker than those of magnesium lithospermate B. However, rats given lithospermic acid, rosmarinic acid or caffeic acid showed no appreciable changes in systolic, mean or diastolic blood pressure throughout the experimental period. Urinary excretion of both kallikrein and sodium was increased significantly in rats given magnesium lithospermate B or lithospermic acid B. These results indicate that the action of these compounds shows a structure-specific pattern.

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Structures of isotanshinones

Cited by 45 publications

References 6 publications

Liposoluble Chemical Constituents in Danshen

Liposoluble Chemical Constituents in Danshen

PTP1B Inhibitory Effect of Abietane Diterpenes Isolated from Salvia miltiorrhiza

Effects on blood pressure of caffeic acid analogues isolated from Salviae Miltiorrhizae Radix in rats with adenine‐induced renal hypertension

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