. 2022 Jul 13;27(14):4491. doi: 10.3390/molecules27144491

Table 1.

Antibacterial activity of known prenylated flavonoids from natural sources.

Plant Source	Compound	Bacteria	IC₅₀ (µg/mL) * or MIC (µg/mL)	PC (µg/mL)				Ref.
Asteraceae
*Helichrysum forskahlii* (J.F. Gmel.) Hilliard and Burtt (aerial parts)	Glabranin	B. subtilis S. aureus	3 6					[64]
Celastraceae
				AB	CI	VA		[63]
*Tripterygium wilfordii* Hook.f. (stems and roots)	Tripteryol B	C. neoformans P. aeruginosa VRE MRSA	3.0 * 8.6 * 4.3 * 4.5 *	0.8 - - -	- 0.1 - 0.2	- - 3.3 -
	(±)-5,4′-Dihydroxy-2′-methoxy-6′,6″-dimethypyraro-(2″,3″:7,8)-6-methyflavanone	MRSA S. aureus	2.1 * 2.6 *	- -	0.2 0.1	- -
	((2S)-5,7,4′-Trihydroxy-2′-methoxy-8,5′-di(3-methyl-2-butenyl)-6-methylflavanone	C. neoformans MRSA S. aureus	1.1 * 2.0 * 2.2 *	0.8 - -	- 0.2 0.10	- - -
Euphorbiaceae
*Macaranga tanarius* L. (fruit)	Propolin D	MSSA (n = 2) MRSA S. epidermidis	10 * 10 * 10 *					[107]
Fabaceae
				MO				[108]
*Amorpha fruticosa* L. (fruit)	Xanthoangelol	S. aureus MRSA	25 µM 3.1 µM	<0.9 µM 3.8 µM				[108]
*Amorpha fruticosa* L. (fruit)	Xanthoangelol	S. aureus MRSA E. faecalis VRE E. faecium VRE. faecium B. subtilis	6.3 3.1 12.5 6.3 12.5 3.1 3.1					[109]
				CI				[110]
*Dalea scandens* *(Miller) R. Clausen var. paucifolia* (roots)**	2(S)-5′-(-1‴,1‴-Dimethylallyl)-8-(3″,3″-dimethylallyl)-2′,4′,5,7-tetrahydroxyflavanone	S. aureus MRSA	1.6 1.6	0.2 0.2
	2(S)-5′-(-1‴,1‴-Dimethylallyl)-8-(3″,3″-dimethylallyl)-2′-methoxy-4′,5,7-trihydroxyflavanone		3.1 3.1
	5′-(1‴,1‴-Dimethylallyl)-8-(3″,3″-dimethylallyl)-2′,4′,5,7-tetrahydroxyflavone		3.1 3.1
*Dalea versicolor* Zucc. var. sessilis (A. Gray) Barneby (whole plants)	2(S)-5′-(1‴,1‴-Dimethylallyl)-8-(3″,3″-dimethylallyl)-2′,4′,5,7-tetrahydroxyflavanone	S. aureus	7.8					[111]
				OX				[112]
*Dalea searlsiae* (Gray) Barneby (roots and aerial parts)	Malheuran A	OSSA ORSA B. cereus	4.3 3.7 3.7	0.4 21.3 106.7
	Malheuran B		3.4 3.7 2.7
	Malheuran C		4.6 4.3 3
	Malheuran D		6.1 6.5 5.0
	(2S)-5′-(2-Methylbut-3-en-2-yl)-8-(3-methylbut-2-en-1-yl)-5,7,2′,4′-tetrahydroxyflavanone		3.1 3.4 2.3
	Prostratol F		6.8 6.4 8
				AP				[113]
*Derris reticulata* Craib. (stem)	Lupinifolin	S. aureus	8	0.3				[113]
				AP	ER			[114]
*Echinosophora koreensis* Nakai (roots)	Kenusanone C	S. epidermidis S. aureus	20 20	20 1.3	1.3 1.3
	Isosophoranone	S. epidermidis S. aureus	20 20	20 1.3	1.3 1.3
	Sophoraisoflavanone A	E. coli S. epidermidis S. aureus	20 20 20	1.3 20 1.3	1.3 1.3 1.3
	Kenusanone A	E. coli S. epidermidis S. aureus	20 20 20	1.3 20 1.3	1.3 1.3 1.3
	Sophoraflavanone D	E. coli S. epidermidis S. aureus	20 20 20	1.3 20 1.3	1.3 1.3 1.3
				NE				[115]
*Erythrina caffra* Thunb. (stem bark)	Abyssinone V 4′-O-methyl ether	E. coli B. subtilis	3.9 15.6	1.6 0.8
	6,8-Diprenylgenistein	S. aureus E. coli B. subtilis	7.8 7.8 15.6	0.8 1.6 0.8
	Alpinumisoflavone	S. aureus E. coli B. subtilis	3.9 3.9 7.8	0.8 1.6 0.8
				CI				[116]
*Erythrina lysistemon* Hutch. (stem bark)	Erybraedin A	B. cereus S. aureus S. epidermidis E. coli	1 2 2 2	0.02 0.1 0.1 0.1
	Phaseollidin	B. cereus S. aureus S. epidermidis	10 10 5	0.02 0.1 0.1
	Abyssinone V 4′-O-methyl ether	B. cereus	26	0.02
	Eryzerin C	B. cereus S. aureus S. epidermidis E. coli P. aeruginosa	10 5 2 5 5	0.02 0.1 0.1 0.1 0.1
	Alpinumisoflavone	B. cereus S. aureus P. aeruginosa	31 31 20	0.02 0.1 0.1
	Lysisteisoflavone	B. cereus S. epidermidis E. coli P. aeruginosa	2 26 6 31	0.02 0.1 0.1 0.1
*Larval stage of Melipotis perpendicularis* (Noctuidae) feeding on the leaves of Lonchocarpus minimiflorus Donn. Sm.**	Lonchocarpol A	MRSA VRE. faecium B. megaterium	0.8–1.6 0.8–1.6 1.0–2.0					[117]
				VA				[118]
*Millettia extensa* (Benth.) Baker (stem)	Millexatin A	S. aureus S. epidermidis B. subtilis	2 2 2	0.3 0.3 0.3
	Millexatin F		2 2 2
	Auriculatin		2 2 2
	Scandenone		2 4 2
	Auriculasin		4 4 8
*Millettia extensa* (Benth.) Baker (leaves and roots)	Millipurone	S. epidermidis B. cereus S. aureus	4 32 4	0.3 0.1 0.3				[119]
	Millexatin K	B. cereus S. aureus	32 32	0.1 0.3
	Millexatin L		32 32
	Millexatin D		8 8
	5,7,3′,4′-Tetrahydroxy-6,8-diprenylisoflavone = 6,8-diprenylorobol		16 32
				CI				[120]
*Pseudarthria hookeri* Wight and Arn. (whole plant)	Pseudarflavone A	E. coli P. aeruginosa S. aureus	4 16 8	0.3 0.1 0.3
	6-Prenylpinocembrin	E. coli E. faecalis S. aureus	4 16 8	0.3 8 0.3
	Boeravinone L	E. coli	16	0.3
*Psoralea corylifolia* L. (seeds)	Bavachin	S. aureus S. epidermidis	37 µM 37 µM					[121]
				GE	OF	AB		[122]
*Retama raetam* Forssk. Webb (flowers)	Licoflavone C	E. coli P. aeruginosa C. glabrata C. albicans C. parapsilosis C. krusei	7.8 15.6 15.6 15.6 15.6 15.6	- 0.5 - - - -	0.1 1 - - - -	- - 0.5 0.5 0.5 0.5
*Retama raetam* Forssk. Webb (flowers)	Derrone		7.8 15.6 7.8 7.8 7.8 7.8	- 0.5 - - - -	0.1 1 - - - -	- - 0.5 0.5 0.5 0.5
				ATB (n = 8)				[123]
*Sophora flavescens* Aiton (roots)	Kuraridin	S. aureus MRSA (n = 6)	8 8–16	0.1→128				[123]
				AP	ER			[114]
		E. coli S. epidermidis S. aureus	20 20 20	1.3 20 1.3	1.3 1.3 1.3
	Kurarinone	E. coli S. epidermidis S. aureus	20 20 20	1.3 20 1.3	1.3 1.3 1.3
				AP	VA			[124]
		MRSA VRE	2 2	250 250	2.5 150			[124]
	Sophoraflavanone G			AP	ER			[114]
		E. coli S. epidermidis S. aureus	20 20 20	1.3 20 1.3	1.3 1.3 1.3			[114]
				ATB (n = 8)				[123]
		S. aureus MRSA (n = 6)	2 2–4	0.1→128				[123]
				AP	OX			[125]
		MSSA MRSA (n = 11)	4 0.5–8	2 64–1024	0.3 256–1024			[125]
	7,9,2′,4′-Tetrahydroxy-8-isopentenyl-5-methoxychalcone	S. aureus MRSA (n = 5) VRE (n = 5)	1.0 1.0–15.6 7.8–15.6					[126]
Moraceae
				VA				[127]
*Artocarpus elasticus* ( leaves)	Elastichalcone C	S. aureus MRSA	8 4	1 1				[127]
				OX				[128]
*Artocarpus integer* (Thunb.) Merr. (roots)	Artocarpin	P. acnes S. aureus S. epidermidis	2 2 4	0.1 0.5 0.5
*Artocarpus integer* (Thunb.) Merr. (roots)	Cudraflavone C	P. acnes S. aureus S. epidermidis	2 2 4	0.1 0.5 0.5
				CI				[129]
*Artocarpus sepicanus* Diels (leaves)	Sepicanin A	MRSA	2.9 µM	0.8				[129]
				AP	ER	AB	MI	[114]
*Broussonetia papyrifera* (L.) Vent. (root bark)	Papyriflavonol A	E. coli S. epidermidis S. aureus S. cerevisiae	20 10 15 12.5	1.3 20 1.3 -	1.3 1.3 1.3 -	- - - 1.3	- - - 1.3
*Broussonetia papyrifera* (L.) Vent. (root bark)	Kazinol B	S. epidermidis S. aureus	20 20	20 1.3	1.3 1.3	- -
				GE	NY			[130]
*Dorstenia angusticornis* Engl. (twigs)	Gancaonin Q	B. cereus B. stearothermophilus B. subtilis E. faecalis	0.6 9.8 9.8 0.6	1.2 4.9 1.2 2.4	- - - -
	Stipulin	P. aeruginosa B. cereus E. faecalis	19.5 4.9 2.4	4.9 1.2 2.4	- - -
	Angusticornin B	E. coli P. aeruginosa B. cereus B. megaterium B. stearothermophilus B. subtilis S. aureus E. faecalis C. albicans C. krusei C. glabrata	1.2 9.8 1.2 2.4 2.4 1.2 2.4 1.2 0.6 1.2 0.6	1.2 4.9 1.2 2.4 4.9 1.2 4.9 2.4 - - -	- - - - - - - - 2.4 2.4 9.8
	Bartericin A	E. coli P. aeruginosa B. cereus B. megaterium B. stearothermophilus B. subtilis S. aureus E. faecalis C. albicans C. krusei C. glabrata	0.6 <0.3 0.6 1.2 2.4 1.2 0.6 0.6 0.6 1.2 0.6	1.2 4.9 1.2 2.4 4.9 1.2 4.9 2.4 - - -	- - - - - - - - 2.4 2.4 9.8
				ATB (n = 7)				[131]
*Dorstenia barteri* Bureau var. multiradiata (stems)	Isobavachalcone	MSSA (n = 2) MRSA (n = 6)	2–16 4–8	0.02→128				[131]
				GE	NY			[132]
		E. faecalis S. aureus B. cereus B. megaterium B. stearothermophilus B. subtilis C. albicans C. glabrata T. rubrum	0.3 0.3 0.6 0.6 0.3 0.6 0.3 0.3 1.2	4.9 2.4 1.2 2.4 4.9 1.2 - - -	- - - - - 2.4 2.4 4.9 1.2
	4-Hydroxylonchocarpin	E. faecalis S. aureus B. cereus B. megaterium B. stearothermophilus B. subtilis C. albicans C. glabrata T. rubrum	4.9 4.9 4.9 1.2 1.2 4.9 4.9 4.9 4.9	4.9 2.4 1.2 2.4 4.9 1.2 - - -	- - - - - - 2.4 2.4 1.2
	Kanzonol C	E. faecalis B. cereus B. megaterium B. stearothermophilus B. subtilis C. albicans C. glabrata	4.9 9.8 4.9 4.9 9.8 4.9 4.9	4.9 1.2 2.4 4.9 1.2 - -	- - - - - 2.4 2.4
				CH	NY			[133]
*Dorstenia mannii* Hook. f. (stems)	Dorsmanin C	P. aeruginosa	4	64	-
	Dorsmanin E	C. albicans	8	-	16
	Dorsmanin F	E. coli C. albicans	4 16	2 -	- 16
	Dorsmanin G	E. coli P. aeruginosa	16 8	2 64	- -
				VA	AP			[134]
*Maclura cochinchinensis* (Lour.) Corner (fruit and leaves)	Gancaonin M	E. faecalis S. aureus MRSA C. albicans	8 2 2 4	2 0.5 1 0.5	0.5 0.3 0.5 0.3
	Lupiwighteone		8 4 8 8
	Lupalbigenin		2 1 1 4
	Scandenone		4 2 2 8
	Auriculatin		2 2 2 2
	Millexatin F		4 1 2 4
	Derrone	S. aureus MRSA C. albicans	4 4 32	0.5 1 0.5	0.3 0.5 0.3
	Macluracochinone E	S. aureus MRSA C. albicans	8 32 32	0.5 1 0.5	0.3 0.5 0.3
				AP	OF	KE		[135]
*Maclura pomifera* (Rafin.) Schneider (fruit)	Scandenone	E. coli S. aureus B. subtilis E. faecalis C. albicans	2 0.5 8 0.5 1	2 0.1 0.5 0.5 -	0.1 0.5 1 1 -	- - - - 1		[135]
*Morus alba* L. (root bark)				KS	AP	ME		[136]
	Kuwanon C	S. aureus MRSA (n = 3)	2 2–4	2 4	4 8–16	32 128–256		[136]
				AP	CI	VA		[137]
		MRSA (n = 3) E. faecalis VRE (n = 3)	2 4 4–8	>16 8 8	8–128 <8 NT	- <16 512→>1024		[137]
				VA				[138]
		MSSA MRSA B. subtilis E. faecalis	2 2 4 4	2 2 ≤0.3 >128				[138]
				AP	CI	VA		[137]
	Kuwanon T	MRSA (n = 3) E. faecalis	4 4	>16 8	8–128 <8	- <16
	Morusinol	MRSA MRSA (n = 2)	16	>16	16	-
	Kuwanon U	MRSA MRSA (n = 2)	4–8	>16	16–128	-
				KS	AP	ME		[136]
		S. aureus MRSA (n = 3)	4 4–8	2 4	4 8–16	32 128–256		[136]
				AP	CI	VA		[137]
	Kuwanon E	MRSA (n = 3)	4–8	>16	8–128	-		[137]
				KS	AP	ME		[136]
		S. aureus MRSA (n = 3)	4 4	2 4	4 8–16	32 128–256		[136]
				ATB (n = 6)				[139]
		MSSA MRSA (n = 10)	4 4–16	4–128 4–256				[139]
				AP	CI	VA		[137]
	Morusin	MRSA (n = 3) E. faecalis VRE (n = 3)	2–4 8 4–8	>16 8 8	8–128 <8 -	- <16 512→>1024		[137]
				KS	AP	ME		[136]
		S. aureus MRSA (n = 3)	4 2–8	2 4	4 8–16	32 128–256		[136]
				VA				[138]
		MSSA MRSA B. subtilis E. faecalis	8 8 4 8	2 2 ≤0.3 >128				[138]
				ATB (n = 6)				[139]
		MSSA MRSA (n = 10)	16 8–32	4–128 4–256				[139]
				KS	AP	ME		[136]
	5′-Geranyl-5, 7, 2′, 4′ -tetrahydroxyflavone	S. aureus MRSA (n = 3)	2 2–4	2 4	4 8–16	32 128–256
	Kuwanon B	S. aureus MRSA (n = 3)	4 4	2 4	4 8–16	32 128–256
*Morus mongolica* Schneider (root bark)				AP	ER			[114]
	Morusin	S. epidermidis	20	20	1.3
	Kuwanon C	E. coli S. epidermidis S. aureus	10 6.3 6.3	1.3 20 1.3	1.3 1.3 1.3
Paulowniaceae
*Paulownia tomentosa* (Thunb.) Steud (fruit)	Tomentodiplacone B			ATB (n = 8)				[98]
	Tomentodiplacone B	S. aureus MRSA (n = 5)	8 8–16	0.1→32
	Mimulone	S. aureus MRSA (n = 5)	2 2–4	0.1→32
				CI				[140]
		B. cereus B. subtilis E. faecalis S. aureus	4 4 4 8	1 2 1 0.5
	Diplacone	B. cereus B. subtilis E. faecalis S. aureus	4 4 4 4	1 2 1 0.5
				ATB (n = 8)				[98]
		S. aureus MRSA (n = 5)	8 8–16	0.1→32
	3′-O-methyl-5′-hydroxydiplacone	S. aureus MRSA (n = 5)	4 4–8	0.1→32
				CI				[140]
		B. cereus B. subtilis E. faecalis S. aureus	4 4 4 2 4	1 2 1 0.5
	3′-O-methyl-5′-O-methyldiplacone	B. cereus B. subtilis E. faecalis S. aureus	4 4 4 4	1 2 1 0.5
				ATB (n = 8)				[98]
		S. aureus MRSA (n = 5)	2 4–8	0.1→32
	3′-O-methyldiplacol		4 4–8	0.1→32
				CI				[140]
		B. cereus B. subtilis E. faecalis S. aureus	2 4 4 2	1 2 1 0.5
	3′-O-methyldiplacone	B. cereus B. subtilis E. faecalis S. aureus	4 8 8 8	1 2 1 0.5
	Tomentodiplacone	B. cereus S. aureus	16 16	1 0.5
Propolis
Taiwanese green propolis	Propolin C	B. subtilis S. aureus (n = 3)	2.5 1.3–5					[141]
	Propolin D		5 10–20
	Propolin F		10 10–20
	Propolin G		10 10–20
Prenylated flavonoids obtained from indefinite source
FLAVONES
Albanin A		MSSA MRSA	32 32					[142]
Artocarpin			1 2
Broussoflavonol F			16 16
Corylifol C		MSSA	16
Glyasperin A				OX	VA	CH	ST	[143]
Glyasperin A		S. aureus	16–32	0.3–0.5	0.5–1	4	8–16	[143]
Kuwanon A		MSSA MRSA	4 8					[142]
Kuwanon C			1 1
Licoflavone B			32 32
Licoflavone B			16 32					[138]
Licoflavone C		MSSA	32 32					[142,144]
Licoflavonol		MSSA MRSA	8 8					[142]
Morusin			8 8
3′-Geranyl -3-prenyl-5,7,2′,4′-tetrahydroxyflavone			4 4
5,7,2′,4′-Tetra-hydroxy-3-geranylflavone			8 8
5,7,4′-Trihydroxy-3,6-dimethoxy-3′,5′-diprenylflavone		MRSA	32
5′-Geranyl-5,7,2′,4′-tetrahydroxyflavone		MSSA MRSA	2 2
6-Prenylapigenin		MSSA MRSA	32 32
6-Prenylquercetin 3-methyl ether		MSSA	32
8-Prenylkaempferol		MSSA MRSA	32 32
ISOFLAVONES
Eurycarpin A		MSSA MRSA	8 8					[142]
Gancaonin M			8 8					[142]
Glycyrrhisoflavone			32 32					[144]
Isoneobavaisoflavone			4 4					[142]
Isowighteone			16 16					[142]
Licoisoflavone A			32 32					[142,144]
Licoisoflavone B				OX	VA	CH	ST	[143]
Licoisoflavone B		S. aureus	4–8	0.3–0.5	0.5–1	4	8–16	[143]
Lupalbigenin		MSSA MRSA	1 1					[142]
Lupiwighteone		MSSA	32
Scandenone, syn. Warangalone		MSSA MRSA	8 2
Sophoraisoflavone A			32 32
Wighteone			8 8
6,8-Diprenylgenistein			4 2
6,8-Diprenylorobol			16 8
8-Prenyldaidzein			32 32
8-Prenylluteone			8 8
FLAVANONES
Bavachin		MSSA	32					[142]
Bavachinin A		MSSA MRSA	4 8
Euchrestaflavanone A			2 2
Glabrol			1 1
			2 2					[144]
				VA
		MRSA (n = 20)	1–4	2–16
Leachianone G		MSSA MRSA	32 32					[142]
Licoflavanone			32 32
Sophoraflavanone C			2 2
6-Prenylnaringenin			8 8
CHALCONES
Desmethylxanthohumol		MSSA MRSA	16 16
Isobavachalcone		MSSA MRSA	4 4
				TE				[145]
			1.6 3.1	0.2 >5.9				[145]
Kanzonol C			4 4					[142]
Licochalcone A			4 4					[142]
			2 4					[144]
				VA				[144]
		MRSA (n = 20)	1–8	2–16				[144]
				OX	VA	CH	ST	[143]
		S. aureus	4	0.3–0.5	0.5–1	4	8–16	[143]
Licochalcone B		MRSA	16					[142,144]
Licochalcone C		MSSA MRSA	4 4					[142,144]
				VA				[144]
		MRSA (n = 20)	1–16	2–16				[144]
Licochalcone D		MSSA MRSA	16 32					[142]
Licochalcone D			32 16					[144]
Licochalcone E			4 4					[142]
			4 4					[144]
				VA				[144]
		MRSA (n = 20)	0.5–16	2–16				[144]
				OX				[146]
		S. aureus MRSA (n = 6)	2 1–4	0.3 0.1–256				[146]
Xanthoangelol		MSSA	32					[142]
Xanthohumol		S. aureus (n = 3)	15.6–62.5					[147]
		MSSA MRSA	4 4					[142]
		S. epidermidis (n = 2) S. capitis ssp. ureolyticus S. aureus MRSA	2 2 2 4					[148]
4-Hydroxyderricin		MSSA MRSA	2 2					[142]
ISOFLAVEN
Glabrene		MSSA MRSA	16 16					[144]

Abbreviations: IC₅₀ (half-maximal inhibitory concentration), MIC (minimum inhibitory concentration), NT (not tested), PC (positive control). Microorganisms tested for the antimicrobial activity: B. cereus (Bacillus cereus), B. megaterium (Bacillus megaterium), B. stearothermophilus (Bacillus stearothermophilus), B. subtilis (Bacillus subtilis), C. albicans (Candida albicans), C. glabrata (Candida glabrata), C. krusei (Candida krusei), C. neoformans (Cryptococcus neoformans), E. coli (Escherichia coli), E. faecalis (Enterococcus faecalis), MRSA (methicillin-resistant Staphylococcus aureus), MSSA (methicillin-sensitive Staphylococcus aureus), ORSA (oxacillin-resistant S. aureus), OSSA (oxacillin-sensitive S. aureus), P. aeruginosa (Pseudomonas aeruginosa), S. aureus (Staphylococcus aureus), S. capitis spp. ureolyticus (Staphylococcus capitis spp. ureolyticus), S. cerevisiae (Saccharomyces cerevisiae), S. epidermidis (Staphylococcus epidermidis), T. rubrum (Trichophyton rubrum), VRE (vancomycin-resistant Enterococcus), VRE. faecium (vancomycin-resistant Enterococcus faecium). Standard antibiotics and antifungals: AB (amphotericin B), AM (amoxicillin), AP (ampicillin), CE (cefazolin), CH (chloramphenicol), CI (ciprofloxacin), CL (clarithromycin), CO (colistin), ER (erythromycin), GE (gentamicin), KE (ketoconazole), KS (kanamycin sulphate), ME (methicillin), MI (miconazole), MO (moxifloxacin), NE (neomycin), NY (nystatin), OF (ofloxacin), OX (oxacillin), PG (penicillin G), RI (rifampicin), ST (streptomycin), TE (tetracycline), VA (vancomycin).