Structural determination of two new sesquiterpenes biotransformed from germacrone by <i>Mucor alternata</i>

Jia, Ning; Ma, Xiao; Lan, Xin Xiu; Jin, Wei; Guo, Dan

doi:10.1002/mrc.2148

Cited by 11 publications

(2 citation statements)

References 13 publications

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“…And then the carbonyl group was reduction to obtain the compound 2 (Sayed 2001 ). Besides, the possible intermediate II, 2′-Z auraptene B ( 3 ), was formed through the hydroxylation of C-9′, which was further hydroxylated at C-4′ or C-5′ to obtain compound 4 or compound 5 , respectively (Silva et al 2013 ; Niu et al 2008 ). The biotransformation of cis -auraptene by Mucor polymorphosporus involved oxidation, hydroxylation and reduction.…”

Section: Resultsmentioning

confidence: 99%

A new terpene coumarin microbial transformed by Mucor polymorphosporus induces apoptosis of human gastric cancer cell line MGC-803

Wang

et al. 2018

Arch. Pharm. Res.

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2′-Z auraptene (1) is a synthesized monoterpene coumarin with anticancer activity against human gastric cancer cells. In order to find new potential anticancer agent, Mucor polymorphosporus was used to transform cis-auraptene. Four new terpene coumarins with notable changes in the skeletal backbone, 2′-Z auraptene A-D (2–5), were obtained and evaluated for their antiproliferative effects against human normal gastric epithelium cells and human gastric cancer cells. These new compounds showed selective cytotoxic activity against MGC-803 cells with IC50 values from 0.78 ± 0.13 to 10.78 ± 1.83 μM and the therapeutic index could also be significantly improved (TI = 59.0) compared with that of 1 (TI = 5.5). The structures of these metabolites were elucidated through extensive spectroscopic methods, and the possible biotransformation pathway of 1 by Mucor polymorphosporus was also proposed. Furthermore, the mechanism of the antiproliferative effects against MGC-803 cells of the most potent compound, 2′-Z auraptene A (2), was characterized. Annexin V/PI staining and abnormal expression of apoptosis-related protein suggested that compound 2 induces apoptosis in gastric cancer MGC-803 cells. Therefore, it is possible that compound 2 has the potential to be applied in gastric cancer therapy.Electronic supplementary materialThe online version of this article (10.1007/s12272-018-1028-0) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

A new terpene coumarin microbial transformed by Mucor polymorphosporus induces apoptosis of human gastric cancer cell line MGC-803

Wang

et al. 2018

Arch. Pharm. Res.

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“…In an effort to enhance the activity of 4, microbial transformation of this compound was performed using Mucor alternata yielding two new compounds, (1S, 4S, 5S, 10R)-isozedoarondiol (5) and (1R, 4S, 5S, 10R)-diepoxy-12-hydroxygermacrone (6) ( Fig. 2) (Jia et al 2008;Niu et al 2008). Sclareolide (7), a natural product isolated from several plant species, displays antifungal, phytotoxic and cytotoxic activities against several human tumor cell lines.…”

Section: Biotransformation Of Sesquiterpenoidsmentioning

confidence: 99%

Terpenoid biotransformations by Mucor species

et al. 2013

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Terpenoids are natural products of great interest due to their widespread use in agrochemicals, drugs, fragrances, flavouring and pigments. Biocatalysts are increasingly being used in the search for new derivatives with improved properties especially to obtain structurally novel leads for new drugs which are difficult to obtain using conventional organic chemical methods. This review, covering up to the end of 2012, reports on the application of Mucor species as catalysts in terpenoid biotransformation to obtain new drug targets, enhance pharmacological activity or decrease the unwanted effects of starting material.

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Structural determination of two new triterpenoids biotransformed from glycyrrhetinic acid by Mucor polymorphosporus

Xin

Yang

Gou

et al. 2009

Magnetic Reson in Chemistry

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Structural determination of two new sesquiterpenes biotransformed from germacrone by Mucor alternata

Cited by 11 publications

References 13 publications

A new terpene coumarin microbial transformed by Mucor polymorphosporus induces apoptosis of human gastric cancer cell line MGC-803

A new terpene coumarin microbial transformed by Mucor polymorphosporus induces apoptosis of human gastric cancer cell line MGC-803

Terpenoid biotransformations by Mucor species

Structural determination of two new triterpenoids biotransformed from glycyrrhetinic acid by Mucor polymorphosporus

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