Table 3.

C-geranylated flavonoids isolated from P. tomentosa

Name of compound and ID	Isolation	Biological activity	Chemical structure

			R1	R2	R3	R4
Mimulone (syn. 6-geranylnaringenin, bonannione A) (21) (2S)	Flowers (Chen et al. 2009; Jiang et al. 2004; Kim et al. 2010a, b), fruit (Asai et al. 2008; Cho et al. 2012, 2013; Lee et al. 2014; Šmejkal et al. 2007a, 2008b)	Antioxidant (Šmejkal et al. 2007b; Zima et al. 2010), antioxidant and anti-inflammatory properties in vitro in S100B-induced human monocytes (Lin et al. 2011), anti-inflammatory activity in LPS-activated THP-1 cells (Peluso et al. 2010); antimicrobial against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. 2008b), antimicrobial against S. aureus and various methicillin resistatant strains of S. aureus (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059) (Navrátilová et al. 2013); cytotoxic [epithelioid cell line WB344 (Šmejkal et al. 2007b), human erythro-leukaemia cell line K562 (Šmejkal et al. 2008a), human ovarian cancer cell line A2780 (Murphy et al. 2005, 2006; Yoder et al. 2007), KB, KB-VIN, A549, DU145 (Rosselli et al. 2011), low activity against T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. 2010)]; SARS-CoV PLpro activity (Cho et al. 2013); hAChE, BChE inhibitor (Cho et al. 2012); significant inhibitory effects against Cp-NanI (a sialidase from C. perfringens) (Lee et al. 2014); weak estrogenic, no progestogenic and androgenic activity (Milligan et al. 2000); inactive against glutamate-induced neurotoxicity studied in primary-cultured rat cortical cells (Kim et al. 2010a, b)	H	H	OH	H
Diplacone (syn. propolin C, nymphaeol A) (22) (2S)	Flowers (Chen et al. 2009; Jiang et al. 2004; Kim et al. 2010a, b), fruit (Asai et al. 2008; Cho et al. 2012, 2013; Lee et al. 2014; Šmejkal et al. 2007a, 2008b)	Antioxidant (Kumazawa et al. 2007; Asai et al. 2008; Šmejkal et al. 2007b; Zima et al. 2010; Trusheva et al. 2011), prooxidant and anti-inflammatory (Hošek et al. 2013); antiherbivore (Kobayashi et al. 2008); antimicrobial against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. 2008b), antimicrobial against S. aureus, various methicillin resistant strains of S. aureus (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059)—most potent together with 31 (Navrátilová et al. 2013) and methicillin-susceptible S. aureus strain. Anti-MRSA, inactive against P. auruginosa (Raghukumar et al. 2010); antiphlogistic (TNF-α, similar to indomethacin) (Hošek et al. 2010), but no anti-inflammatory effect was observed in COX-2 inhibition assay (Phommart et al. 2005); cytotoxic (epithelioid cell line WB344 (Šmejkal et al. 2007a), T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. 2010), human erythro-leukaemia cell line K562 (Šmejkal et al. 2008a), KB human oral carcinoma, human breast cancer, human small cell lung cancer NCI-H187 (Phommart et al. 2005), induction of apoptosis via caspase activation, bid and cytochrome c release in human melanoma cells (Chen et al. 2004), human ovarian cancer cell line A2780 (Murphy et al. 2005, 2006; Yoder et al. 2007), PC-3, DU-145, Hep-3B cell line (Chen et al. 2012)); hAChE, BChE inhibitor (Cho et al. 2012), SARS-CoV PLpro activity (Cho et al. 2013); significant inhibitory effects against Cp-NanI (a sialidase from C. perfringens) (Lee et al. 2014); selective docking to Leishmania major N-myristoyltransferase (Ogungbe et al. 2014); antileishmanial activity (L. donovani amastigotes) (Salem et al. 2011); inactive against glutamate-induced neurotoxicity studied in primary-cultured rat cortical cells (Kim et al. 2010a, b)	H	OH	OH	H
Diplacol (23) (2R, 3R)	Fruit (Asai et al. 2008), flowers, leaves (Kobayashi et al. 2008)	Antioxidant (Asai et al. 2008); cytotoxic (human ovarian cancer cell line A2780) (Murphy et al. 2006; Yoder et al. 2007), low activity against T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. 2010)	OH	OH	OH	H
3′-O-methyldiplacone (24)	Fruit (Asai et al. 2008; Cho et al. 2012, 2013; Lee et al. 2014; Šmejkal et al. 2007a, 2008b), flowers and leaves (Kobayashi et al. 2008)	Antioxidant (Šmejkal et al. 2007a; Yazaki et al. 2009); SARS-CoV PLpro activity (Cho et al. 2013); weak hAChE, BChE inhibitor (Cho et al. 2012); significant inhibitory effects against Cp-NanI (a sialidase from C. perfringens) (Lee et al. 2014); strong docking energy to L. major pteridine reductase 1, selective docking to glycerol-3-phosphate dehydrogenase (Ogungbe et al. 2014), antileishmanial activity (L. donovani amastigotes) (Salem et al. 2011); activity against lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. 2010), human erythro-leukaemia cell line K562 (Šmejkal et al. 2008a); weak antimicrobial against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. 2008b), weak antimicrobial activity against S. aureus, various methicillin resistant strains of S. aureus (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059) (Navrátilová et al. 2013)	H	OMe	OH	H
3′-O-methyldiplacol (syn. diplacol 3′-O-methylether) (25) (2R, 3R)	Flowers (Kobayashi et al. 2008), fruit (Asai et al. 2008; Cho et al. 2012, 2013; Šmejkal et al. 2008b)	Antioxidant (Asai et al. 2008; Yazaki et al. 2009), antimicrobial against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. 2008b), antimicrobial against S. aureus and various methicillin resistant strains of S. aureus (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059)—most potent together with 27 (Navrátilová et al. 2013); cytotoxic (human erythro-leukaemia cell line K562) (Šmejkal et al. 2008a), low activity against T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. 2010); SARS-CoV PLpro activity (Cho et al. 2013); hAChE, BChE inhibitor (Cho et al. 2012); antileishmanial activity (L. donovani amastigotes) (Salem et al. 2011), selective docking to L. major methionyl tRNA synthetase (Ogungbe et al. 2014)	OH	OMe	OH	H
3′-O-methyl-5′-O-methyldiplacone (syn. 6-geranyl-4′,5,7-trihydroxy-3′,5′-dimethoxyflavanone) (26) (2S)	Fruit (Asai et al. 2008; Cho et al. 2012, 2013; Šmejkal et al. 2008b)	Antioxidant (Yazaki et al. 2009), antimicrobial against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. 2008b), antimicrobial against S. aureus and various methicillin resistant strains of S. aureus (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059) (Navrátilová et al. 2013); cytotoxic (multiple myeloma RPMI 8226 and U266 cell lines, human cervical cancer cells HeLa, BJ human fibroblast cell line (Šmejkal et al. 2010), human erythro-leukaemia cell line K562) (Šmejkal et al. 2008a); SARS-CoV PLpro activity (Cho et al. 2013); hAChE, BChE inhibitor (Cho et al. 2012)	H	OMe	OH	OMe
3′-O-methyl-5′-hydroxydiplacone (syn. 6-geranyl-4′,5,5′,7-tetrahydroxy-3′-methoxyflavanone) (27) (2S)	Immature fruit (Asai et al. 2008), fruit (Šmejkal et al. 2008b), leaves (Kobayashi et al. 2008)	Antioxidant (Asai et al. 2008; Yazaki et al. 2009; Zima et al. 2010); antimicrobial activity against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. 2008b), antimicrobial against S. aureus and various methicillin resistant strains of S. aureus (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059) (Navrátilová et al. 2013); cytotoxic (human erythro-leukamia cell line K562) (Šmejkal et al. 2008a), activity against T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. 2010)	H	OMe	OH	OH
3′-O-methyl-5′-methoxydiplacol (28) (racemic mixture of 2R, 3R and 2S, 3S)	Fruit (Šmejkal et al. 2007a)		OH	OMe	OH	OMe
6-Geranyl-5,7-dihydroxy-3′,4′-dimethoxyflavanone (29) (2S)	Immature fruit (Asai et al. 2008)	Antioxidant (Asai et al. 2008)	H	H	OMe	OMe
6-Geranyl-3′,5,7-tri-hydroxy-4′-methoxyflavanone (syn. 4′-O-methyldiplacone) (30) (2S)	Immature fruit (Asai et al. 2008), fruits (Cho et al. 2012, 2013; Lee et al. 2014)	Antioxidant (Asai et al. 2008); SARS-CoV PLpro activity (Cho et al. 2013); hAChE, BChE inhibitor (Cho et al. 2012); significant inhibitory effects against Cp-NanI (a sialidase from C. perfringens) (Lee et al. 2014); antileishmanial activity (L. donovani amastigotes) (Salem et al. 2011)	H	H	OMe	OH
6-Geranyl-3,3′,5,7-tetrahydroxy-4′-methoxyflavanone (syn. 4′-O-methyldiplacol) (31) (2R, 3R)	Immature fruit (Asai et al. 2008), fruit (Cho et al. 2012, 2013)	Antioxidant (Asai et al. 2008), SARS-CoV PLpro activity (Cho et al. 2013); hAChE, BChE inhibitor (Cho et al. 2012)	OH	H	OMe	OH
Schizolaenone C (32) (2S)	Fruit (Šmejkal et al. 2010)	Cytotoxic (T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, human cervical cancer cells HeLa, BJ human fibroblast cell line) (Šmejkal et al. 2010), cytotoxic (human ovarian cancer cell line A2780) (Murphy et al. 2006; antioxidant (Zima et al. 2010)	H	OH	H	OH
6-Geranyl-3,3′,5,5′,7-pentahydroxy-4′-methoxyflavanone (33) (2R, 3R)	Fruit (Cho et al. 2012)	hAChE, BChE inhibitor (Cho et al. 2012)	OH	OH	OMe	OH
6-Geranyl-3′,5,5′,7-tetrahydroxy-4′-methoxyflavanone (34) (2S)			H	OH	OMe	OH
Tomentodiplacone B (35) (2S)	Fruits (Šmejkal et al. 2008b)	Antioxidant (Yazaki et al. 2009; Zima et al. 2010); low direct cytotoxicity (human erythro-leukamia cell line K562) (Šmejkal et al. 2008a); low direct activity against T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. 2010), effect on cell cycle (THP-1 human monocytic leukaemia cells) (Kollár et al. 2011); antimicrobial against S. aureus and various methicillin resistant strains of S. aureus (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059) (Navrátilová et al. 2013), no antimicrobial activity on Gram-negative bacteria or yeast and on seven Gram-positive bacteria (Navrátilová et al. 2013; Šmejkal et al. 2008b)

			R
3,3′,4′, 5,7-Pentahydroxy-6-[7-hydroxy-3,7-dimethyl-2(E)octenyl] flavanone (36) (2R, 3R)	Immature fruit (Asai et al. 2008)	Antioxidant (Asai et al. 2008)	OH
Prokinawan (37) (2S)	Flowers (Kobayashi et al. 2008), immature fruit (Asai et al. 2008)	Antioxidant (Asai et al. 2008)	H

			R1	R2	R3
Tomentodiplacone (38) (2S)	Fruit (Šmejkal et al. 2008b)	Antioxidant (Yazaki et al. 2009); antimicrobial against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. 2008b), weak erythroid differentiation activity (Šmejkal et al. 2008a)	H	OMe	H
Tomentodiplacol (39) (2R, 3R)	Fruit (Šmejkal et al. 2007a)	Antioxidant (Šmejkal et al. 2007a)	OH	OMe	H
4′,5,5′,7-Tetrahydroxy-6-[6-hydroxy-3,7-dimethyl-2(E),7-octadienyl]-3′-methoxyflavanone (40) (2S)	Immature fruit (Asai et al. 2008)	Antioxidant (Asai et al. 2008)	H	OMe	OH
3,3′,4′,5,7-Pentahydroxy-6-[6-hydroxy-3,7-dimethyl-2(E),7-octadienyl]flavanone (41) (2R, 3R)	Immature fruit (Asai et al. 2008)	Antioxidant (Asai et al. 2008)	OH	OH	H
Tanariflavanone D (42) (2S)	Immature fruit (Asai et al. 2008), fruit (Schneiderová et al. 2013)	Antioxidant (Asai et al. 2008; Phommart et al. 2005); cytotoxic (human breast cancer cell line BC) (Phommart et al. 2005); no anti-inflammatory effect in COX-2 inhibition assay (Phommart et al. 2005)	H	H	OH
Tomentomimulol (43) (2R, 3R)	Fruit (Schneiderová et al. 2013)		OH	H	H
Mimulone B (44) (2S)	Fruit (Schneiderová et al. 2013)		H	H	H

			R
Tomentodiplacone C (45) (racemic mixture of 2R, 2S)	Fruit (Navrátilová et al. 2013)	Antimicrobial against S. aureus and various methicillin resistant strains of S. aureus (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059), no antimicrobial activity on Gram-negative bacteria, minor ability to affect the initiation of eukaryotic translation via dual-luciferase reported assay (firefly and renilla) in comparison with anisomycin (Navrátilová et al. 2013)	OMe
Mimulone E (46) (2S)	Fruit (Navrátilová et al. 2013)		H

			R
Tomentodiplacone D (47) (2S)	Fruit (Navrátilová et al. 2013)	Antimicrobial against S. aureus and various methicillin resistant strains of S. aureus (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059), no antimicrobial activity on Gram-negative bacteria, no ability to affect the initiation of eukaryotic translation via dual-luciferase reported assay (firefly and renilla) (Navrátilová et al. 2013)
Tomentodiplacone E (48) (2S)	Fruit (Navrátilová et al. 2013)
Tomentodiplacone F (49) (2S)	Fruit (Navrátilová et al. 2013)
Tomentodiplacone G (50) (2S)	Fruit (Navrátilová et al. 2013)	Antimicrobial against S. aureus and various methicillin resistant strains of S. aureus (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059), no antimicrobial activity on Gram-negative bacteria, no ability to affect the initiation of eukaryotic translation via dual-luciferase reported assay (firefly and renilla) (Navrátilová et al. 2013)
Tomentodiplacone H (51) (racemic mixture 2R, 2S)	Fruit (Navrátilová et al. 2013)
Tomentodiplacone I (52) (racemic mixture of 2R, 2S)	Fruit (Navrátilová et al. 2013)
Mimulone C (53) (2S)	Fruit (Navrátilová et al. 2013)	Antimicrobial against S. aureus and various methicillin resistant strains of S. aureus (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059), no antimicrobial activity on Gram-negative bacteria, 53 has no ability to affect the initiation of eukaryotic translation via dual-luciferase reported assay (firefly and renilla) (Navrátilová et al. 2013)
Mimulone D (54) (2S)	Fruit (Navrátilová et al. 2013)

			R1	R2	R3	R4
Tomentin A (55) (2S)	Fruit (Cho et al. 2013)	Activity against Severe acute respiratory syndrome corona virus (SARS-CoV PLpro, a reversible inhibitor 63 was the most potent compound tested (Cho et al. 2013)	H	H	OH	OH
Tomentin B (56) (2S)			H	H	OMe	OH
Tomentin C (57) (2S)			H	OH	OMe	OMe
Tomentin D (58) (2S)			H	OMe	OH	OMe
Tomentin E (59) (2R, 3S)			OH	H	OH	OMe