Structures of two natural hypotensive Diels-Alder type adducts, mulberrofurans F and G, from the cultivated mulberry tree (Morus lhou Kiodz.)

Fukai, Toshio; Hano, Yoshio; Hirakura, Kazuhiro; Nomura, Taro; Uzawa, Jun; Fukushima, Kazutaka

doi:10.1248/cpb.33.3195

Cited by 69 publications

(47 citation statements)

References 2 publications

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“…1) were isolated from the bark extract of Morus alba L. with ordinaland reversed-phase column chromatography and subsequent preparative HPLC. Compounds 1 5) and 2 8) were identified by MS and 1 H-NMR comparison with the literature data. On evaluation of these compounds for their cytotoxicities on HL60 and CRL1579 cell lines, compound 1 exhibited potent activity against both HL60 (IC 50 1.7 mM) and CRL1579 (9.8 mM) cell lines which were almost comparable with those of a reference compound, cisplatin (Table 1).…”

Section: Resultsmentioning

confidence: 96%

“…Fraction E12-2 (74 mg) eluted with MeOH-H 2 O (3 : 2) was subjected to reversed-phase preparative HPLC on an ODS column (Pegasil ODS-II 5 mm column, 25 cmϫ10 mm i.d. ; Senshu Scientific Co., Ltd., Tokyo, Japan) eluted with MeCN-H 2 O-AcOH (55 : 45 : 1; flow rate 3.0 ml/min) to yield albanol A (1, mulberrofuran G; 13.1 mg; retention time 16.8 min) 5) and mulberofuran Q (2; 1.8 mg; 10.3 min). Cytotoxicity Assay Cytotoxicity assay was performed according to the previous method.…”

Section: Methodsmentioning

confidence: 99%

“…2,3) Recently, albanol A 4) (mulberrofuran G 5) ) (1) and several other related compounds, isolated from the stem bark of M. australis, have been reported to show potent cytotoxic activities against four human cancer cell lines, lung (A549), stomach (BGC 823), colon (HCT-8), and ovarian (A2780) cancer cell lines, by means of the thiazolyl blue tetrazolium bromide (MTT) assay. 3) In the course of our search for potential bioactive compounds from natural sources, 6,7) we were especially interested to undertake the investigation on the mechanisms of cytotoxic action of the "Diels-Alder-type adducts".…”

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Albanol A from the Root Bark of Morus alba L. Induces Apoptotic Cell Death in HL60 Human Leukemia Cell Line

et al. 2010

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Mulberry (Morus spp.; Moraceae), whose leaves represent indispensable food for silkworms, has been widely cultivated in China and Japan since early times. On the other hand, the root bark of mulberry (Mori Radicis Cortex) has been used in the traditional Chinese medicine as antiphlogistic, diuretic, antitussive, expectorant, antiheadache, and antipyretic. 1)Many novel compounds, regarded biogenetically as "DielsAlder-type adducts" of dehydroprenyl phenols and chalcone derivatives, have been isolated from several Morus species.2,3) Recently, albanol A 4) (mulberrofuran G 5) ) (1) and several other related compounds, isolated from the stem bark of M. australis, have been reported to show potent cytotoxic activities against four human cancer cell lines, lung (A549), stomach (BGC 823), colon (HCT-8), and ovarian (A2780) cancer cell lines, by means of the thiazolyl blue tetrazolium bromide (MTT) assay.3) In the course of our search for potential bioactive compounds from natural sources, 6,7) we were especially interested to undertake the investigation on the mechanisms of cytotoxic action of the "Diels-Alder-type adducts". In this study, we have isolated albanol A (1) and mulberofuran Q (2) from the root bark of M. alba, and have evaluated their cytotoxic activity against human leukemia (HL60) and human melanoma (CRL1579) cells. In addition, we have studied the apoptosis-inducing activity of albanol A (1), which exhibited potent cytotoxicity against HL60 cells, and the mechanisms of apoptotic cell death in HL60. Results and DiscussionAlbanol A (1) and mulberofuran Q (2) (Fig. 1) were isolated from the bark extract of Morus alba L. with ordinaland reversed-phase column chromatography and subsequent preparative HPLC. Compounds 1 5) and 2 8) were identified by MS and 1 H-NMR comparison with the literature data. On evaluation of these compounds for their cytotoxicities on HL60 and CRL1579 cell lines, compound 1 exhibited potent activity against both HL60 (IC 50 1.7 mM) and CRL1579 (9.8 mM) cell lines which were almost comparable with those of a reference compound, cisplatin (Table 1).Compound 1 was then evaluated for its inducing activity of early apoptosis on HL60 cells. Exposure of the membrane phospholipid, phosphatidylserine, to the external cellular environment is one of the earliest markers of apoptotic cell death.9) Annexin V is a calcium-dependent phospholipidbinding protein with high affinity for phosphatidylserine expressed on the cell surface. Propidium iodide (PI) does not enter whole cells with intact membranes and was used to differentiate between early apoptotic (Annexin V possitive, PI negative), late apoptotic (Annexin V, PI double positive), or necrotic cell death (Annexin V negative, PI positive). The proportion of early apoptotic HL60 cells (lower right) was significantly increased after 6 h of incubation with 1 (30 mM) Albanol A (1), isolated from the root bark extract of Morus alba (mulberry), was evaluated for the cytotoxic and apoptosis-inducing activities in human leukemia (HL60) cells, and ...

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Section: Resultsmentioning

confidence: 96%

Section: Methodsmentioning

confidence: 99%

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Albanol A from the Root Bark of Morus alba L. Induces Apoptotic Cell Death in HL60 Human Leukemia Cell Line

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“…14) Therefore, this herb has also been applied for the control of inflammation, diabetes, and bronchial asthma. 15,16) Recently, a few papers have reported the hypotensive 31,32) and antiviral 33,34) effects of natural Diels-Alder type adducts or flavonoids or HEMA. Specifically, HEMA inhibits cAMP phosphodiesterase activity, 35) and flavonoids and related compounds from mulberry tree regulate the arachidonate metabolism in rat platelet homogenates.…”

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Inhibitory Effects of Morus alba on Compound 48/80-Induced Anaphylactic Reactions and Anti-Chicken Gamma Globulin IgE- Mediated Mast Cell Activation

Chai

Lee

Han

et al. 2005

Biological & Pharmaceutical Bulletin

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Mast cells are widely distributed throughout vascularized tissues and certain epithelia.1) Mast cells are responsible for a variety of allergic disorders including allergic rhinitis, dermatitis, asthma, and food allergies, as well as catastrophic anaphylactic reactions to insect stings and some drugs. These cells respond to IgE-directed antigens via the high-affinity receptor for IgE, Fce RI, by releasing granules that contain preformed inflammatory mediators and generating inflammatory lipids and cytokines. 2,3) Species of the genus Dorstenia (Moraceae) are perennial, herbaceous plants that are widely distributed in tropical Africa, Asia, Middle-East, Central and South America. 4,5) Moraceae comprises a large family of sixty genera and nearly 1400 species, including important groups such as Artocarpus, Morus, and Ficus. The species of Morus have been shown to exhibit anti-HIV, anti-oxidative, anti-hypotensive, and cytotoxic activities. [6][7][8] Plants of this genus are known to be rich in flavonoids, 9,10) a group of chemicals shown to have potent antiviral activities against herpes simplex virus, rhinovirus, human immunodeficiency virus, and various respiratory viruses. [11][12][13] This herb has been long used as an antiphlogistic, diuretic, and expectorant, 14) and also applied for control of inflammation, diabetes, and bronchial asthma. 15,16) The phenolic constituents and flavonoids of mulberry tree inhibits cAMP phosphodiesterase activity and regulates arachidonate metabolism in rat platelet homogenates. 17) Although studies have demonstrated that various effects of M. alba on numerous disease, the anti-allergic activity of the root bark of M. alba is poorly understood. Since calcium and cAMP have been shown to play a pivotal role in the mast cell activations, we have assessed the effect of the root bark of M. alba on calcium uptake and change of intracellular cAMP in mast cells. In this paper, we show that the root bark of M. alba inhibits the compound 48/80-induced systemic anaphylactic shock and anti-CGG IgE-induced rat peritoneal mast cell activations and the increased vascular permeability while cAMP level is increased. In addition, its effects are compared with disodium cromoglycate (DSCG), a known cell stabilizer which inhibits the release of pre-formed and newly synthesized chemical mediators from a variety of cells involved in allergic and inflammatory responses. 18) MATERIALS AND METHODS MaterialsCompound 48/80, bovine serum albumin (BSA), disodium cromoglycate (DSCG) and HEPES, chicken gamma globulin (CGG) were purchased from Sigma Chemical Co. (MO, U.S.A.). DSCG, an antianaphylactic agent, was used as positive control in order to compare with HEMA activity. Percoll solution was purchased from Pharmacia (Uppsala, Sweden). Anti-CGG IgE antibodies were supplied by Hern-Ku Lee works for department of immunology, Chonbuk National University Medical School.Experimental Animals Male ICR mice and SpragueDawley rats aged 8-10 weeks were purchased from Dae Han Experimental Animal Center (Daejeon, Korea...

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“…8) The root bark of M. alba is commonly known by the Chinese name of "Sang-Bai-Pi" and is widely used for its anti-inflammatory, antihypertensive, diuretic, and antipyretic effects. 9) M. alba extracts have also been reported to possess hypotensive, 10) hypoglycemic, 11) hepatoprotective, 12) neuroprotective, 13) and anti-inflammatory 14) activities. However, while M. alba extracts have been reported to exert antidepressant or antistress activities in various animal models, little is known about the antidepressant-like effects of active compounds from the root bark of M. alba extracts.…”

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Antidepressant-Like Effects of Sanggenon G, Isolated from the Root Bark of <i>Morus alba</i>, in Rats: Involvement of the Serotonergic System

Lim

Jung

Park

et al. 2015

Biological & Pharmaceutical Bulletin

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The root bark of Morus alba is commonly used as an alternative medicine due to its numerous health benefits in humans. However, the antidepressant effects of various active components from M. alba have not been fully elucidated. In this study, we aimed to determine whether sanggenon G, an active compound isolated from the root bark of M. alba, exhibited antidepressant-like activity in rats subjected to forced swim test ( Key words Morus alba; sanggenon G; depression; serotonin; forced swim testDepression is a chronic disease that has an enormous impact on society. According to the predictions of the World Health Organization, by the year 2020, depression will be the second leading global burden of illness.1) Despite recent progress in the development of clinically relevant antidepressant drugs, currently available antidepressant are not totally effective and are associated with many undesirable adverse effects.2) Because of the limitations of antidepressant drugs, alternative approaches, such as medicinal herbs, have been studied for their potential applications in the treatment of depression.3,4) Moreover, many herbal extracts have been shown to have antidepressant effects in a variety of animal models. For example, Hypericum perforatum, also known as St. John's wort, is widely used for the treatment of mild to moderate depression. 5) Panax ginseng, commonly known as Korea Ginseng, has been investigated experimentally and clinically for its stress-attenuating activity. 6,7)The mulberry tree (Morus alba L.), one of the most wellknown and widely distributed trees of the family Moraceae, is extensively cultivated in East Asia; the leaves of M. alba L. are an indispensable food source for silkworms, and the fruits are consumed in normal diets.8) The root bark of M. alba is commonly known by the Chinese name of "Sang-Bai-Pi" and is widely used for its anti-inflammatory, antihypertensive, diuretic, and antipyretic effects. 9) M. alba extracts have also been reported to possess hypotensive, 10) hypoglycemic, 11) hepatoprotective, 12) neuroprotective, 13) and anti-inflammatory 14) activities. However, while M. alba extracts have been reported to exert antidepressant or antistress activities in various animal models, little is known about the antidepressant-like effects of active compounds from the root bark of M. alba extracts. [15][16][17][18] In the present study, the antidepressant-like effects of sanggenon G (Fig. 1), a major phenolic compound isolated from the ethyl acetate-soluble fraction of the root bark of M. alba, were investigated in response to the forced swim test (FST) in rats. Moreover, to determine the neurobiological effects underlying the antidepressant-like activity of the sanggenon G, corticosterone responses and c-Fos immunoreactivity were evaluated in rats exposed to FST.

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Structures of two natural hypotensive Diels-Alder type adducts, mulberrofurans F and G, from the cultivated mulberry tree (Morus lhou Kiodz.)

Cited by 69 publications

References 2 publications

Albanol A from the Root Bark of Morus alba L. Induces Apoptotic Cell Death in HL60 Human Leukemia Cell Line

Albanol A from the Root Bark of Morus alba L. Induces Apoptotic Cell Death in HL60 Human Leukemia Cell Line

Inhibitory Effects of Morus alba on Compound 48/80-Induced Anaphylactic Reactions and Anti-Chicken Gamma Globulin IgE- Mediated Mast Cell Activation

Antidepressant-Like Effects of Sanggenon G, Isolated from the Root Bark of <i>Morus alba</i>, in Rats: Involvement of the Serotonergic System

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