Novel triterpenoids and glycosides from durian exert pronounced anti-inflammatory activities

Feng, Jianying; Yi, Xin; Huang, Wenjie; Wang, Yihai; He, Xiangjiu

doi:10.1016/j.foodchem.2017.08.097

Cited by 24 publications

(22 citation statements)

References 22 publications

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“…With the close cooperation of biochemists, microbiologists, and genetic scientists, microbial biosynthesis can become a promising technology for obtaining valuable pentacyclic triterpenoids. The compounds discussed in the review exhibit antitumor, antiviral, hepatoprotective, neuroprotective, and other activities [5,7,42,60,74,82,83]. Despite the wide range of known biological properties, the use of pentacyclic triterpenoids in pharmacology and medicine is limited because of their high hydrophobicity.…”

Section: Discussionmentioning

confidence: 99%

“…The most available oleanane triterpenoids are oleanolic acid 1 (OA, 3β-hydroxy-olean-12-en-28-oic acid, C 30 H 48 O 3 , CAS 508-02-1) and glycyrrhetinic acid 2 (GA, 3β-hydroxy-11-oxo-18β-olean-12-en-30-oic acid, C 30 H 46 O 4 , CAS 471- , and ursolic acid 3 (UA, 3β-hydroxy-urs-12-en-28-oic acid, C 30 H 48 O 3 , CAS 77-52-1) is the most available ursane triterpenoid. Biosynthesis of oleanane and ursane pentacyclic triterpenoids in plants occurs by conversion of the acyclic triterpene squalene (4) to 2,3-oxidosqualene (5) and its further cyclization by specific enzyme complexes (oxidosqualene cyclase) via β-amyrin (6) or α-amyrin (7), respectively [36,37]. The carbon skeletons of these triterpenoids consist of five condensed cyclohexane rings.…”

Section: Distribution In Naturementioning

confidence: 99%

“…UA could be an effective antidiabetic agent due to its ability to inhibit α-glucosidase activity [60]. OA and UA exhibited their inhibitory effects against lypopolysaccharide (LPS)-induced NO production in RAW 264.7 cells that determined their anti-inflammatory activity [7].…”

Section: Biological Activities Of Triterpenic Acids and Their Native mentioning

confidence: 99%

“…Thus, the OA derivatives 22β-acetoxy-3,25-epoxy-3α-hydroxyolean-12-en-28-oic acid (26) Oleanane derivatives from Panax stipuleanatus (C3, C28-diglycosides 32-34) and Astilbe rivularis (3β-trans-p-coumaroyloxy-olean-12-en-27-oic acid (35) and 6β-hydroxy-3-oxoolean-12-en-27-oic acid (36)) as well as oleanane and ursane polyhydroxylated derivatives (37)(38)(39)(40) from Rosa laevigata exhibited anti-inflammatory activities [88][89][90] due to the suppression of TGFBIp-mediated hyperpermeability in vitro and in vivo as well [90]. Ursane derivatives from Durio zibethinus were shown to exhibit a more pronounced anti-inflammatory effect in LPS-induced NO production in RAW 264.7 cell inhibition tests compared to oleanane triterpenoids, for which the activity was reduced by C2 hydroxylation [7].…”

Section: Biological Activities Of Triterpenic Acids and Their Native mentioning

confidence: 99%

“…Naturally occurring triterpenoids are represented by more than 100 various types of skeletons [2]. Native triterpenoids, in particular, oleanane and ursane representatives, are of interest for researchers due to their availability and multiple biological activities, including antimicrobial, anti-inflammatory, antitumor, cytotoxic, hepatoprotective, and other activities [3][4][5][6][7]. Triterpenic molecules, however, are highly hydrophobic which significantly limits their use as effective pharmacological agents.…”

Section: Introductionmentioning

confidence: 99%

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Biotransformation of Oleanane and Ursane Triterpenic Acids

2020

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Oleanane and ursane pentacyclic triterpenoids are secondary metabolites of plants found in various climatic zones and regions. This group of compounds is highly attractive due to their diverse biological properties and possible use as intermediates in the synthesis of new pharmacologically promising substances. By now, their antiviral, anti-inflammatory, antimicrobial, antitumor, and other activities have been confirmed. In the last decade, methods of microbial synthesis of these compounds and their further biotransformation using microorganisms are gaining much popularity. The present review provides clear evidence that industrial microbiology can be a promising way to obtain valuable pharmacologically active compounds in environmentally friendly conditions without processing huge amounts of plant biomass and using hazardous and expensive chemicals. This review summarizes data on distribution, microbial synthesis, and biological activities of native oleanane and ursane triterpenoids. Much emphasis is put on the processes of microbial transformation of selected oleanane and ursane pentacyclic triterpenoids and on the bioactivity assessment of the obtained derivatives.

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