Table 3.
Biological activity of pentacyclic triterpenoid products derived by biotransformation.
| Microorganism | Initial Compound, Concentration | Derivative, Yield | Biological Activity | Reference |
|---|---|---|---|---|
| Fungi | ||||
| Rhizomucor miehei CECT 2749 | OA, 0.5 g/L | 1β,30-dihydroxy-OA (47), 5.0% | - * | [108] |
| 7β,30-dihydroxy-OA (48), 6.0% | - | |||
| 30-hydroxy-OA (25, queretaroic acid), 5.0% | Antitumor | |||
| OA methyl ester, 0.3 g/L | Methyl 3β,7β,30-trihydroxy-oleane-9(11),12-dien-28-oate (49), 15.0% | - | [112] | |
| Trichothecium roseum (M 95.56) | OA, 0.08 g/L | 7β,15α-dihydroxy-3-oxo-olean-12-en-28-oic acid (51), 7.5% | Anti-inflammatory | [114] |
| 15α-hydroxy-3-oxo-olean-12-en-28-oic acid (52), 6.25% | - | |||
| Circinella muscae AS 3.2695 | OA, 0.02 g/L | 7β,15α-dihydroxy-3-oxo-olean-12-en-28-oic acid (51), 6.1% | Anti-inflammatory | [15] |
| 7β-hydroxy-OA (53), 5.8% | Anti-inflammatory | |||
| 7β,21β-dihydroxy-OA (54), 4.2% | - | |||
| 7α,21β-dihydroxy-OA (55), 3.1% | - | |||
| 7β,15α-dihydroxy-OA (56), 4.9% | Anti-inflammatory | |||
| 7β-hydroxy-3-oxo-olean-12-en-28-oic acid (57), 3.8% | - | |||
| 7β,15α-dihydroxy-OA 28-O-β-d-glucopyranosyl ester (58), 4.7% | Anti-inflammatory | |||
| 21β-hydroxy-OA 28-O-β-D-glucopyranosyl ester (59), 5.1% | Anti-inflammatory | |||
| OA 28-O-β-D-glucopyranosyl ester (60), 5.5% | Anti-inflammatory | |||
| GA, 0.06 g/L | 7β-hydroxy-GA (61), 1.5% | Anti-inflammatory Antimicrobial |
[115] | |
| 15α-hydroxy-GA (62), 1.9% | Anti-inflammatory | |||
| 7β,15α-dihydroxy-GA (63), 1.8% | Anti-inflammatory Antioxidant Hepatoprotective |
|||
| 3,11-dioxo-7β-hydroxy-18β-olean-12-en-30-oic acid (64), 1.7% | Anti-inflammatory Antimicrobial |
|||
| 7β,15α-dihydroxy-3,11-dioxo-18β-olean-12-en-30-oic acid (65), 2.2% | Anti-inflammatory | |||
| 7β-hydroxy-11-oxo-18β-olean-12-en-30-oic acid 3-O-β-d-glucopyranoside (66), 1.8% | Anti-inflammatory | |||
| 7β-hydroxy-11-oxo-18β-olean-12-en-30-oic acid 3-O-β-d-6′-O-acetyl-glucopyranoside (67), 1.1% | Anti-inflammatory | |||
| 15α-hydroxy-11-oxo-18β-olean-12-en-30-oic acid 3-O-β-d-glucopyranoside (68), 2.5% | Anti-inflammatory | |||
| 15α-hydroxy-11-oxo-18β-olean-12-en-30-oic acid 3-O-β-d-6′-O-acetyl-glucopyranoside (69), 1.8% | Anti-inflammatory | |||
| 7β-hydroxy-GA 30-O-β-d-glucopyranoside (70), 2.2% | Anti-inflammatory | |||
| Rhizopus arrhizus AS 3.2893 | GA, 0.06 g/L | 7β-hydroxy-GA (61), 2.8% | Anti-inflammatory Antimicrobial |
[115] |
| 15α-hydroxy-GA (62), 2.2% | Anti-inflammatory | |||
| 7β,15α-dihydroxy-GA (63), 1.7% | Anti-inflammatory Antioxidant Hepatoprotective |
|||
| 3β-acetoxy-7β-hydroxy-11-oxo-18β-olean-12-en-30-oic acid (71), 1.7% | Anti-inflammatory | |||
| 7-oxo-GA (72), 1.3% | Anti-inflammatory | |||
| 7α-hydroxy-GA (73), 2.6% | Anti-inflammatory | |||
| 15α-hydroxy-7-oxo-GA (74), 1.3% | Anti-inflammatory | |||
| Colletotrichum lini AS 3.4486 | GA, 0.25 g/L | 7β,15α-dihydroxy-GA (63), NR ** | Anti-inflammatory Antioxidant Hepatoprotective |
[118] |
| Absidia pseudocylinderospora ATCC 24169 | GA, 1.0 g/L | 7β,15α-dihydroxy-GA (63), 18.0% | Anti-inflammatory Antioxidant Hepatoprotective |
[117] |
| Cunninghamella blakesleana CGMCC 3.970 | GA, 0.1 g/L | 15α,24-dihydroxy-GA (75), 0.11% | Anti-inflammatory | [14] |
| 15α,24-dihydroxy-3,11-dioxo-18β-olean-12-en-30-oic acid (76), 0.75% | - | |||
| 7β,24-dihydroxy-3,11-dioxo-18β-olean-12-en-30-oic acid (77), 0.16% | - | |||
| 3,11-dioxo-7β,15α,24-trihydroxy-18β-olean-12-en-30-oic acid (78), 0.29% | Anti-inflammatory | |||
| 7α,24-dihydroxy-3,11-dioxo-18β-olean-12-en-30-oic acid (79), 1.27% | Anti-inflammatory | |||
| C. blakesleana CGMCC 3.970 | GA, 0.3 g/L | 7β-hydroxy-GA (61), 30.0% | Anti-inflammatory Antimicrobial |
[116] |
| 3,11-dioxo-7β-hydroxy-18β-olean-12-en-30-oic acid (64), 25.0% | Anti-inflammatory Antimicrobial |
|||
| C. elegans TSY-0865 | GA, 0.4 g/L | 7β-hydroxy-GA (61), 2.5% | Anti-inflammatory Antimicrobial |
[119] |
| Syncephalastrum racemosum GCMCC 3.2500 | UA, 0.1 g/L | 7β,21β-dihydroxy-UA (80), 12.9% | - | [13] |
| 1β,21β-dihydroxy-UA (81), 3.9% | - | |||
| 1β-hydroxy-21-oxo-UA (82), 12.1% | - | |||
| 3β,21β-dihydroxy-urs-11-en-28,13-olide (83), 3.4% | Antihepatitis | |||
| 3β,7β,21β-trihydroxy-urs-11-en-28,13-olide (84), 2.9% | Antihepatitis | |||
| Gliocladium roseum CGMCC 3.3657 | UA, 0.1 g/L | 21β-hydroxy-3-oxo-urs-12-en-3,4-olide-28-oic acid (85), 8.0%) | - | [121] |
| 3,21-dioxo-urs-12-en-3,4-olide-28-oic acid (86), 6.25% | Antihepatitis | |||
| 21β-hydroxy-3,4-seco-ursane-4(23),12-diene-3,28-dioic acid (87), 1.5% | - | |||
| 21-oxo-3,4-seco-ursane-4(23),12-diene-3,28-dioic acid (88), 1.0% | Antihepatitis | |||
| Mucor spinosus AS 3.3450 | UA, 0.3 g/L | 7β-hydroxy-UA 28-ethanone (89), 5.04% | Antitumor | [122] |
| 7β,21β-dihydroxy-UA (81), 1.64% | - | |||
| 21β-hydroxy-urs-12-en-28-oic acid 3-O-β-d-glucopyranoside (90), 2.13% | - | |||
| Rhizopus chinensis CICC 40335 | OA, 0.2 g/L | 7β,21β-dihydroxy-OA (54), 53.75% | - | [34] |
| GA, 0.2 g/L | 7β-hydroxy-GA (61), 77.5% | Anti-inflammatory Antimicrobial |
||
| Bacteria | ||||
| Nocardia iowensis (DSM 45197, NRRL 5646) | OA, 0.3 g/L | Methyl 3β-hydroxy-olean-12-en-28-oat (91), 63.0% | Antitumor | [16] |
| Methyl 3-oxo-olean-12-en-28-oat (92, oleanonic acid methyl ester), 5.0% | Antitumor Antiprotozoal |
|||
| Metabolite 93 with hydroxyl and methyl groups, 2.0% | - | |||
| Streptomyces griseus ATCC 13273 | OA, 0.04 g/L | 3β-hydroxy-olean-12-ene-28,29-dioic acid (94), 21.9% | - | [128] |
| 3β,24-dihydroxy-olean-12-ene-28,29-dioic acid (95), 32.7% | - | |||
| 3β,21β,24-trihydroxy-olean-12-ene-28,29-dioic acid (96), 5.9% | Anti-inflammatory | |||
| S. griseus ATCC 13273 | UA, 0.04 g/L | 3β-hydroxy-urs-12-ene-28,30-dioic acid (97), 30.4% | - | [17] |
| 3β,24-dihydroxy-urs-12-ene-28,30-dioic acid (98), 31.6% | - | |||
| 3-oxo-UA, 0.04 g/L | 3-oxo-urs-12-ene-28,30-dioic acid (100), 24,1% | - | ||
| 24-hydroxy-3-oxo-urs-12-ene-28,30-dioic acid (101), 45.9% | - | |||
| 2α-hydroxy-UA, 0.04 g/L | 2α,3β-dihydroxy-urs-12-ene-28,30-dioic acid (102), 29.0% | - | ||
| 2α,3β,24-trihydroxy-urs-12-ene-28,30-dioic acid (103), 15.9% | - | |||
| Bacillus megaterium CGMCC 1.1741 | UA, 0.2 g/L | 1β,11α-dihydroxy-UA (104), 26.87% | - | [18] |
| 3-oxo-urs-12-en-28-oic acid (99), 6.23% | Anti-leishmania | |||
| 1β,11α-dihydroxy-3-oxo-urs-12-en-28-oic acid (105), 13.5% | Anti-inflammatory | |||
| 1β-hydroxy-3-oxo-urs-12-en-28,13-olide (106), 5.03% | Anti-inflammatory | |||
| 1β,11α-dihydroxy-3-oxo-urs-12-en-28-O-β-d-glucopyranoside (107), 8.57% | - | |||
| B. subtilis ATCC 6633 | 7β,21β-dihydroxy-OA, 0.2 g/L | 7β,21β-dihydroxy-olean-12-en-28-oic acid 3-O-β-d-glucopyranoside (108), 46.5% | - | [34] |
| GA, 0.2 g/L | GA 30-O-β-d-glucopyranoside (111), 27.5% | - | ||
| 7β-hydroxy-GA, 0.2 g/L | 7β-hydroxy-GA 30-O-β-d-glucopyranoside (68), 44.0% | - | ||
| S. griseus ATCC 13273 | 7β,21β-dihydroxy-OA, 0.2 g/L | 7β,21β,29-trihydroxy-OA (109), 26.0% | - | |
| 3β,7β,21β-trihydroxy-olean-12-ene-28,29-dioic acid (110), 15.0% | Neuroprotective | |||
Note: * Biological activity of the compound has not yet been detected. ** The value is not reported. GA, glycyrrhetinic acid; OA, oleanolic acid; UA, ursolic acid.