Chemical structures, production and enzymatic transformations of sapogenins and saponins from Centella asiatica (L.) Urban

Azerad, Robert

doi:10.1016/j.fitote.2016.07.011

Cited by 53 publications

(30 citation statements)

References 113 publications

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“…9, 10, 11 Our previous studies demonstrated that the triterpenoid-rich fraction of this herb could ameliorate dextran sulfate sodium (DSS)-induced colitis in mice (unpublished data). Madecassoside, the most abundant triterpene in this herb, was shown to regulate the balance of Th17/Treg cells in a collagen-induced arthritis in rats.…”

mentioning

confidence: 97%

Madecassic acid, the contributor to the anti-colitis effect of madecassoside, enhances the shift of Th17 toward Treg cells via the PPARγ/AMPK/ACC1 pathway

Wang

Wei

et al. 2017

Cell Death Dis

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The imbalance between Th17 and Treg cells substantially contributes to the intestinal immune disturbance and subsequent tissue injury in ulcerative colitis. The triterpenoid-rich fraction of Centella asiatica was able to ameliorate dextran sulfate sodium-induced colitis in mice. Here we explored its active ingredient and underlying mechanism with a focus on restoring the Th17/Treg balance. The four main triterpenoids occurring in C. asiatica were shown to attenuate colitis in mice by oral administration. The most effective ingredient madecassoside lost anti-colitis effect when applied topically in the colon, and madecassic acid was recognized to be the active form of madecassoside. Oral administration of madecassic acid decreased the percentage of Th17 cells and downregulated the expression of RORγt, IL-17A, IL-17F, IL-21 and IL-22 and increased the percentage of Treg cells and the expression of Foxp3 and IL-10 in the colons of mice with colitis, but it did not affect Th1 and Th2 cells. Under Th17-polarizing conditions, madecassic acid downregulated ACC1 expression and enhanced the shift of Th17 cells toward Treg cells, but it did not affect the differentiation of Treg cells under Treg-polarizing conditions. Both compound C and AMPK siRNA inhibited the madecassic acid-mediated downregulation of ACC1 expression and shift of Th17 cells to Treg cells under Th17-polarizing conditions. GW9662, T0070907 and PPARγ siRNA blocked the effect of madecassic acid on AMPK activation, ACC1 expression and shift of Th17 cells to Treg cells. Furthermore, madecassic acid was identified as a PPARγ agonist, as it promoted PPARγ transactivation. The correlation between activation of PPARγ and AMPK, downregulation of ACC1 expression, restoration of Th17/Treg balance and attenuation of colitis by madecassic acid was validated in mice with DSS-induced colitis. In conclusion, madecassic acid was the active form of madecassoside in ameliorating colitis by restoring the Th17/Treg balance via regulating the PPARγ/AMPK/ACC1 pathway.

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confidence: 97%

Madecassic acid, the contributor to the anti-colitis effect of madecassoside, enhances the shift of Th17 toward Treg cells via the PPARγ/AMPK/ACC1 pathway

Wang

Wei

et al. 2017

Cell Death Dis

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“…To date, 33 oleanane- and ursane-type saponins have been reported in C. asiatica [ 26 ], all of them containing a glucose linked to the triterpene C-28 carboxyl, whereas no glucose linked with C-2α, C-3β, and C-23 positions has been observed. Therefore, it seems very likely that UGT73AH1 catalyzes glycosylation at the C-28 carboxyl function en route to the asiaticoside triterpene saponins.…”

Section: Resultsmentioning

confidence: 99%

Characterization of the Asiatic Acid Glucosyltransferase, UGT73AH1, Involved in Asiaticoside Biosynthesis in Centella asiatica (L.) Urban

Kim¹,

Jin²,

Lee³

et al. 2017

IJMS

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Centella asiatica (L.) Urban contains two ursane-type triterpene saponins, asiaticoside and madecassoside, as major secondary metabolites. In order to select candidate genes encoding UDP-glucosyltransferases (UGTs) involved in asiaticoside biosynthesis, we performed transcriptomic analysis of leaves elicited by methyl jasmonate (MeJA). Among the unigenes, 120 isotigs and 13 singletons of unique sequences were annotated as UGTs, including 37 putative full-length cDNAs, and 15 of the putative UGT genes were named according to the UGT committee nomenclature protocols. One of them, UGT73AH1, was characterized by heterologous expression in Escherichia coli BL21 (DE3) cells. After induction with IPTG, a total protein extract was assayed with UDP-glucose and asiatic acid. UPLC-QTOF/MS analysis showed that UGT73AH1 catalyzes the glycosylation of asiatic acid to its monoglucoside. It remains unclear whether glycosylation occurs on the triterpene C-2α, C-3β, C-23, or C-28 position. However, it is very likely that UGT73AH1 glucosylates the C-28 position, because only C-28 bears a glucose moiety in the final pathway product of asiatic acid, while C-2α, C-3β, and C-23 remain un-conjugated.

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“…When incubated with Chaetomium olivaceum, pseudoprotodioscin was transformed into eight saponins, three of which showed cell-protection activity against H 2 O 2 -induced H9c2 cardiomyocyte [175]. Data on the microbial transformations of one of the Centella plant saponins, the asiatic acid by Alternaria longipes, Penicillium lilacinum, Fusarium equiseti, and Streptomyces griseus, were recently reviewed, pointing out that some of the obtained derivatives showed improved characteristics in comparison with the parent compound [176].…”

Section: Microbial Transformations Of Saponins and Sapogeninsmentioning

confidence: 99%

Microbial Transformations of Plant Secondary Metabolites

Mutafova¹,

Fernandes²,

Mutafov³

et al. 2016

Bioprocessing of Plant in Vitro Systems

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The aim of this chapter is to present the authors' view on the place and role of microbial transformation reactions as a perspective means of processing of plantderived biologically active compounds into metabolites with new and/or increased activity and availability and decreased toxicity. Some microbial transformations providing information regarding metabolism in humans and mammals of plant-derived secondary metabolites applied as drugs and/or food additives are also considered.

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Chemical structures, production and enzymatic transformations of sapogenins and saponins from Centella asiatica (L.) Urban

Cited by 53 publications

References 113 publications

Madecassic acid, the contributor to the anti-colitis effect of madecassoside, enhances the shift of Th17 toward Treg cells via the PPARγ/AMPK/ACC1 pathway

Madecassic acid, the contributor to the anti-colitis effect of madecassoside, enhances the shift of Th17 toward Treg cells via the PPARγ/AMPK/ACC1 pathway

Characterization of the Asiatic Acid Glucosyltransferase, UGT73AH1, Involved in Asiaticoside Biosynthesis in Centella asiatica (L.) Urban

Microbial Transformations of Plant Secondary Metabolites

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