Schulzeines A−C, New α-Glucosidase Inhibitors from the Marine Sponge <i>Penares schulzei</i><sup>1</sup>

Takada, Kentaro; Uehara, Taisuke; Nakao, Yoichi; Matsunaga, Shigeki; Soest, R.W.M. van; Fusetani, Nobuhiro

doi:10.1021/ja037368r

Cited by 113 publications

(74 citation statements)

References 18 publications

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“…Three new isoquinoline alkaloids, schulzeines A (8), B (9), and C (10), were isolated from the marine sponge Penares schulzei [17]. Schulzeines A-C encompass two amino acids and a C 28 fatty acid, the last of which was sulfated.…”

Section: Alkaloids Tinospora Cordifoliamentioning

confidence: 99%

“…Schulzeines A-C encompass two amino acids and a C 28 fatty acid, the last of which was sulfated. Schulzeines A-C inhibit α-glucosidase with IC 50 values of 48-170 nM [17].…”

Section: Alkaloids Tinospora Cordifoliamentioning

confidence: 99%

“…Three quinolizidine alkaloids, javaberine A (16), javaberine A hexaacetate (17), and javaberine B hexaacetate (18), were isolated from Talinum paniculatum Gaertner (Portulacaceae); they are inhibitors of TNF-α production by macrophages and fat cells, and T. paniculatum is useful as a dieting supplement and for prevention of diabetes [20]. Three quinolizidine alkaloids, lupanine (19), 13-α-OH lupanine (20), and 17-oxo-lupanine (21) Five isoquinoline alkaloids, berberine chloride (26), berberine sulfate (27), berberine iodide (28), palmatine sulfate (29), and palmatine chloride (30), have been isolated from the root of Coptis japonica makino var.…”

Section: Alkaloids Tinospora Cordifoliamentioning

confidence: 99%

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Antidiabetic Agents from Medicinal Plants

Jung¹,

Park²,

Lee³

et al. 2006

CMC

464

268

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Currently available therapeutic options for non-insulin-dependent diabetes mellitus, such as dietary modification, oral hypoglycemics, and insulin, have limitations of their own. Many natural products and herbal medicines have been recommended for the treatment of diabetes. The present paper reviews medicinal plants that have shown experimental or clinical antidiabetic activity and that have been used in traditional systems of medicine; the review also covers natural products (active natural components and crude extracts) isolated from the medicinal plants and reported during 2001 to 2005. Many kinds of natural products, such as terpenoids, alkaloids, flavonoids, phenolics, and some others, have shown antidiabetic potential. Particularly, schulzeines A, B, and C, radicamines A and B, 2,5-imino-1,2,5-trideoxy-L-glucitol, beta-homofuconojirimycin, myrciacitrin IV, dehydrotrametenolic acid, corosolic acid (Glucosol), 4-(alpha-rhamnopyranosyl)ellagic acid, and 1,2,3,4,6-pentagalloylglucose have shown significant antidiabetic activities. Among active medicinal herbs, Momordica charantia L. (Cucurbitaceae), Pterocarpus marsupium Roxb. (Leguminoceae), and Trigonella foenum graecum L. (Leguminosae) have been reported as beneficial for treatment of type 2 diabetes.

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Section: Alkaloids Tinospora Cordifoliamentioning

confidence: 99%

“…Schulzeines A-C encompass two amino acids and a C 28 fatty acid, the last of which was sulfated. Schulzeines A-C inhibit α-glucosidase with IC 50 values of 48-170 nM [17].…”

Section: Alkaloids Tinospora Cordifoliamentioning

confidence: 99%

Section: Alkaloids Tinospora Cordifoliamentioning

confidence: 99%

See 1 more Smart Citation

Antidiabetic Agents from Medicinal Plants

Jung¹,

Park²,

Lee³

et al. 2006

CMC

464

268

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“…and schulzeines A-C (Penares schulzei), which inhibits a-glucosidase with IC 50 values between 48 and 170 nM. 12 However, no chemistry has been reported from sponges belonging to the genus Ecionemia.…”

Section: Introductionmentioning

confidence: 99%

Ecionines A and B, two new cytotoxic pyridoacridine alkaloids from the Australian marine sponge, Ecionemia geodides

et al. 2010

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a b s t r a c tChemical investigations of the Australian marine sponge Ecionemia geodides resulted in the isolation of two new pyridoacridine alkaloids, ecionines A (1) and B (2), along with the previously isolated marine natural products, biemnadin (3) and meridine (4). Compounds 1 and 2 both contain an imine moiety, which is rare for the pyridoacridine structure class. The chemical structures of 1 and 2 were determined by extensive 1D and 2D NMR and MS data analyses. All compounds were tested against a panel of human bladder cancer cell lines, the increasingly metastatic TSU-Pr1 series (TSU-Pr1, TSU-Pr1-B1 and TSU-Pr1-B2) and the superficial bladder cancer cell line 5637. Ecionine A (1) displayed cytotoxicity against all cell lines, with IC 50 values ranging from 3 to 7 mM. This is the first report of chemistry from the sponge genus Ecionemia.Crown

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“…7,8) Furthermore, recent investigations have reported that the compounds with cinnamic amide unit have strong a-glucosidase inhibition activities. [9][10][11] These motivated us to carry out further structural modifications on oleanolic acid by incorporating different cinnamic amide units.In the present paper, a series of analogues with the oleanolic acid core and different cinnamic amide ligands were designed, synthesized, and evaluated as a-glucosidase inhibitors (Fig. 1, Table 1).…”

mentioning

confidence: 99%

Synthesis of New .ALPHA.-Glucosidase Inhibitors Based on Oleanolic Acid Incorporating Cinnamic Amides

Nie

Luo

Wang

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Type II diabetes mellitus affects approximately 215 million people worldwide. It is currently clear that aggressive control of hyperglycemia in patients with type II diabetes can attenuate the development of chronic complications such as retinopathy and nephropathy.1) To date, therapy for type II diabetes relies mainly on several approaches intended to suppress the hyperglycemia, which include reducing gut glucose absorption. Therefore inhibition of a-glucosidase, an enzyme catalyzing the cleavage of glycosidic bonds in oligosaccharides or glycoconjugates, is a choice to control elevated glucose level in blood.Oleanolic acid is the hypoglycemic component in many Traditional Chinese Medicines (TCMs). In previous reports, some oleanolic acid derivatives have been designed, synthesized based on inhibitor of glycogen phosphorylase (GP). 2-6)But it was found that oleanolic acid and its derivates were used to suppress the hyperglycemia for not only inhibitor of glycogen phosphorylase but also inhibitors of a-glucosidase in our previous research. 7,8) Furthermore, recent investigations have reported that the compounds with cinnamic amide unit have strong a-glucosidase inhibition activities. [9][10][11] These motivated us to carry out further structural modifications on oleanolic acid by incorporating different cinnamic amide units.In the present paper, a series of analogues with the oleanolic acid core and different cinnamic amide ligands were designed, synthesized, and evaluated as a-glucosidase inhibitors (Fig. 1, Table 1). Their structure-activity relationships also were analyzed. Results and DiscussionWith oleanolic acid as a lead compound, we sought to identify a series of oleanolic acid derivatives as novel a-glucosidase inhibitor. Synthetic efforts were focused on structural modifications at C-3 and C-28 positions. The synthetic route of 28-substituted oleanolic acid derivatives is outlined in Chart 1. Piperazine fragment was induced in order to link cinnamic amide unit with oleanolic acid at C-28.Oleanolic acid unit and cinnamic amide unit were connected at N-1 and N-4 positions of piperazine, respectively. On basis of these, 3,28-disubstituted oleanolic acid deriva- Department of Medicinal Chemistry, China Pharmaceutical University; 24 Tongjia Xiang, Nanjing 210009, People's Republic of China. Received March 24, 2011; accepted May 24, 2011; published online May 30, 2011 A series of a a-glucosidase inhibitors with the oleanolic acid core and different cinnamic amide ligands were designed and synthesized. Their preliminary structure-activity relationships were analyzed. In general, the compounds with 3,28-disubstituted oleanolic acid exhibited stronger activity than those 28-monosubstituted analogues, and variation of cinnamic amide substitution significantly affected a a-glucosidase inhibition activities. Most of the compounds showed potent inhibitory activity against a a-glucosidase with much greater efficacy than a typical a a-glucosidase inhibitor, acarbose. Synthesis of New a a-Glucosidase Inhibitors ...

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Schulzeines A−C, New α-Glucosidase Inhibitors from the Marine Sponge Penares schulzei¹

Cited by 113 publications

References 18 publications

Antidiabetic Agents from Medicinal Plants

Antidiabetic Agents from Medicinal Plants

Ecionines A and B, two new cytotoxic pyridoacridine alkaloids from the Australian marine sponge, Ecionemia geodides

Synthesis of New .ALPHA.-Glucosidase Inhibitors Based on Oleanolic Acid Incorporating Cinnamic Amides

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Schulzeines A−C, New α-Glucosidase Inhibitors from the Marine Sponge Penares schulzei1

Cited by 113 publications

References 18 publications

Antidiabetic Agents from Medicinal Plants

Antidiabetic Agents from Medicinal Plants

Ecionines A and B, two new cytotoxic pyridoacridine alkaloids from the Australian marine sponge, Ecionemia geodides

Synthesis of New .ALPHA.-Glucosidase Inhibitors Based on Oleanolic Acid Incorporating Cinnamic Amides

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Schulzeines A−C, New α-Glucosidase Inhibitors from the Marine Sponge Penares schulzei¹