Biotransformations of Imbricatolic Acid by Aspergillus niger and Rhizopus nigricans Cultures

Schmeda-Hirschmann, Guillermo; Aranda, Carlos; Kurina, Marcela; Rodrı́guez, Jaime A.; Theoduloz, Cristina

doi:10.3390/12051092

Cited by 13 publications

(2 citation statements)

References 33 publications

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“…Functionalized derivatives of sesquiterpenes [5,6] and triterpenes [7] have also been obtained as fungal metabolites. Reports on the biotransformation of many different types of diterpenes, such as labdane [8], trachylobane [9,10], stemodane [11], aphidicolane [12], pimaradiene [13], abietane [14], taxane [15], atisane [16], and beyerane [17] are also very frequently found in the literature.…”

Section: Introductionmentioning

confidence: 99%

The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations

et al. 2014

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Abstract:The use of biotransformations in organic chemistry is widespread, with highlights of interesting applications in the functionalization of natural products containing unactivated carbons, like the kaurane diterpenes. A number of compounds with kaurane skeletons can be isolated in large amounts from several plant species and a myriad of biological activities has been related to these compounds. Studies on structure versus activity have showed that, in most cases, in kaurane diterpenes, activity increases with the increase of functionalization. Since naturally occurring kaurane diterpenes usually have limited functional groups to be used as targets for semi-synthetic modifications, production of more polar derivatives from kaurane diterpenes have been achieved mostly through the use of fungal biotransformations. In this review, selected examples the wonderful chemical diversity produced by fungi in kaurane diterpenes is presented. This diversity includes mainly hydroxylation of nearly all carbon atoms of the kaurane molecule, many of them carried out stereoselectively, as well as ring rearrangements, among other chemical modifications. Sources of starting materials, general biotransformation protocols employed, OPEN ACCESSMolecules 2014, 19 1857 fungi with most consistent regioselectivity towards kaurane skeleton, as well as biological activities associated with starting materials and products are also described.

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Section: Introductionmentioning

confidence: 99%

The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations

et al. 2014

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“…The researchers used isosteviol as a substrate for Fusarium verticilloides (Sacc.) to select for therapeutic metabolites of isosteviol [128]. Hydroxyl groups were introduced to isosteviol by fungi.…”

Section: Stevia Rebaudiana Bertonimentioning

confidence: 99%

Mechanisms of phytochemicals from murraya koenigii and stevia rebuadiana in cell model of diabetes, hepatocellular carcinoma and cholangiocarcinoma under hyperglycemic conditions

Nooron

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Diabetes mellitus (DM) is a group of metabolic disorders in which high blood glucose levels over a prolonged period, caused by deficiency of insulin production from the pancreas, or by the insulin resistance. Several epidemiological studies suggest that diabetic population is not only at increased risk of cardiovascular complications, but also at substantially higher risk of many types of malignancies.?Hyperglycemia induced free radical reactive oxygen species (ROS) production, which is a major cause of cell injury and organ damage, especially affects pancreatic beta cells. Whereas insulin resistance in skeletal muscle tissue and adipocyte are the major sites of postprandial glucose disposal, and enhancing glucose uptake into this tissue may decrease insulin resistance in type 2 diabetes patients. Moreover, Hyperglycemia and hyperinsulinemia in DM also showed the strong relation with cholangiocarcinoma proliferation and migration, the high prevalence cancer in the Northeast of Thailand. The study of phytochemical chemistry form?Murraya koenigii?and?Stevia rebuadiana?were conducted to investigate their pharmacological properties in various model that related to DM such as hyperglycemia, insulin resistance as well as in cancer cell line. Mahanine, a carbazole alkaloid from?Murraya koenigii?showed the outstanding protective effects in high glucose induced oxidative stress in RIN-m5F pancreatic beta cells via suppression of NADPH oxidase gene expression. Moreover, mahanine increased the insulin secretion by stimulating the pancreatic duodenum homeobox-1(PDX-1) expression and translocation, proinsulin (PRE-INS), and glucose transporter 2 (GLUT2) and glucokinase (GCK) gene expression. In addition mahanine enhanced the insulin sensitizing effects in skeletal muscle and adipocyte cells by increased glucose uptake and promoted glucose transporter 4 (GLUT4) translocation via activation of the Akt signaling pathway. Furthermore, mahanine showed the potent cytotoxicity in HepG2 human hepatocellular carcinoma and HuCCT1 and KKU-100 human cholangiocarcinoma cells, which was associated with increased the expression levels of MITF. Whereas the phytochemical chemistry from?S.?rebuadian;?steviol, isosteviol and 7 ?-OHisosteviol, also presented the anti-diabetes effects by increased the glucose uptake and GLUT 4 translocation but least potent than mahanine. These study suggested that mahanine have anti-diabetic potential for treating diabetes and anti-cancer,?which potentially to?use as concomitant herbal medicine?in cancer and/or diabetes patient without concerning of cancer treatment-induced DM and DM treatment-induced cancer.?

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Microbial transformation of antimalarial terpenoids

Parshikov

Netrusov

Sutherland

2012

Biotechnology Advances

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Biotransformations of Imbricatolic Acid by Aspergillus niger and Rhizopus nigricans Cultures

Cited by 13 publications

References 33 publications

The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations

The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations

Mechanisms of phytochemicals from murraya koenigii and stevia rebuadiana in cell model of diabetes, hepatocellular carcinoma and cholangiocarcinoma under hyperglycemic conditions

Microbial transformation of antimalarial terpenoids

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