TABLE 1.

The compounds isolated to date from P. ecklonii Benth.

	Isolated compounds	IUPAC name and CID number	Isolation and/or identification methods	Biological Activity a	Solvent extractor/plant part(s)	Ref.
	Terpenes and sterols
Diterpenes	Parviflorone D (1)	11-hydroxy-2α-(4-hydroxybenzoyloxy)-abieta-5,7,9(11),13-tetraene-12-one (1) [101967011]	MS + NMR	Antibacterial	DCM:EtAc	Gurlal (2005)
			NMR	Antiplasmodic	DCM/ap	Van Zyl et al. (2008)
					EtAc/ap	Nyila et al. (2009), Nyila et al. (2012)
			MS + NMR	Antibacterial	Acetone/wp	Simões et al. (2010)
				Antitumour	Acetone	Martens and Mithöfer (2005), Ozgen et al. (2008), Falé et al. (2009), Bhatt et al. (2013), Kumar and Pandey, (2013), Petersen (2013), Burmistrova et al. (2015), Andrade et al. (2018), Costa et al. (2018), Sitarek et al., (2020), Śliwiński et al. (2020)
				Antioxidant		Wellsow et al. (2006)
			-	Enzyme inhibition	-	(Nyila et al., 2009; Dai and Mumper, 2010)
	Parviflorone F (2)	11-hydroxy-2α-(3,4-dihydroxybenzoyloxy)-abieta-5,7,9(11),13-tetraene-12-one (2) [10389067]	NMR	N/A	Ether/ap	Uchida et al. (1980)
				Antiplasmodic	DCM/ap	van Zyl et al. (2007), Van Zyl et al., (2008)
				Antibacterial	EtAc/ap	(Nyila et al., 2009; Nyila, 2010)
			NMR	Antitumour	EtAc/ap	Nyila et al. (2009)
			-	Antioxidant	-	Narukawa et al. (2001)
			-	Enzyme inhibition	-	Nyila et al. (2009), Dai and Mumper, (2010)
	Parviflorone E (3)	11-Hydroxy-19-(3,4-dihydroxybenzoyloxy)-abieta-5,7,9(11),13-tetraene-12-one (3) [10366501]	NMR	Antiplasmodic	ap	Van Zyl et al. (2008)
			HPLC-DAD/MS	Anticariogenic	Metanol/ap	Figueiredo et al. (2014)
			-	Antioxidant	-	Narukawa et al. (2001)
	Sugiol(4)	12-hydroxyabieta-8,11,13-trien-7-one (4) [94162]	MS + NMR	Antibacterial, antiplasmodic	Acetone/wp	van Zyl et al., (2007), Simões et al., (2010)
				Antioxidant		Chao et al. (2005), Bajpai et al. (2014)
				Antiinflammatory		Chao et al. (2005)
				Antitumoral		Son et al. (2005)
Triterpenes	Mix of Ursolic acid (5) and Oleanolic acid (6)	3β-hydroxy-urs-12-en-28-oic acid (5) [64945]		Antiinflammatory (5) Antibacterial, antiviral, antiplasmodic (5 and 6), Antitumoral		Andersson et al. (2003), Checker et al. (2012)
		3β-hydroxyolean-12-en-28-oic acid (6) [10494]
Sterols	Mix of ß-sitosterol (7) and Stigmasterol (8)	3β-stigmast-5-en-3-ol (7) [222284]		Antibacterial		Liu et al. (2019)
		stigmasta-5,22(E)-dien-3ß-ol (8) [5280794]
	Phenolic compounds
Hydroxyccinamic acids	Caffeic acid (9)	3,4-dihydroxycinnamic acid (10) [689043]	NMR	Antimicrobial	Methanol:Water/ap	Hawas et al. (2008)
			HPLC-DAD	Antioxidant, enzyme inhibition	Water (decoction)	Gomes et al. (2012)
			-	Antiinflammatory	-	Da Cunha et al. (2004), Gamaro et al. (2011), Yang et al. (2013)
			-	Antitumoral	-	Hawas et al. (2008), Gomes et al. (2012)
	Caffeic acid derivatives
	Rosmarinic acid (10)	3,4-Dihydroxycinnamic acid (R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl ester (10) [5281792]	N/A	Antibacterial	Water (decoction)/ap	Figueiredo et al. (2010)
			HPLC-DAD	Antioxidant, enzyme inhibition	Water (decoction)	Falé et al. (2009), Gomes et al. (2012)
			-	Antiinflammatory		Gamaro et al. (2011)
			-	Antitumoral		Figueiredo et al. (2010)
	Nepetoidin A (11)	(Z,E)-[2-(3,5-dihydroxyphenyl)ethenyl] 3-(3,4-dihydroxyphenyl)-2-propenoate (11) [5316820]	HPLC-DAD/NMR	Anticariogenic	Methanol/ap	Figueiredo et al. (2014)
				Antifungal and antioxidant	Diethyl ether/ap	Grayer et al. (2003)
	Nepetoidin B (12)	(Z,E)-[2-(3,4-dihydroxyphenyl)ethenyl] 3-(3,4-dihydroxyphenyl)-2-propenoate (12) [5316819]		Anti-inflammatory (11 and 12)	-	Grayer et al. (2003)
	Chlorogenic acid (13)	5-O-cafeoilquinic acid (13) [1794427]	HPLC-DAD	Antioxidant, enzyme inhibition	Water (decoction)	Gomes et al. (2012)
Flavones	Apigenin (19)	4’,5,7-trihydroxyflavone (19) [5280443]	NMR	Antimicrobial	Methanol:Water/ap	Hawas et al. (2008)
			HPLC/LC-MS	N/A	Diethyl ether/ap	Grayer et al. (2010)
			No information provided	Antiplasmodic	-	Lehane and Saliba, (2008)
			-	Antioxidant	-	Velioglu et al. (1998), Pietta (2000)
			-	Anti-inflammatory	-	Nakanishi et al. (1990), Hirano et al., (2004), Kim et al. (2004), Choi et al. (2014), Lago et al. (2014)
			-	Antitumoral	-	Wu et al. (2014)
	Apigenin derivatives
	Apigetrin (15)	apigenin 7-O-β-glucoside (15) [5280704]	NMR	Antimicrobial	Methanol:Water/ap	Hawas et al. (2008)
	Apigenin 4',6-dimethoxy -7-O-β-glucoside (16)	apigenin 4',6-dimethoxy-7-O-β-glucoside (16) [44257792]
	Vitexin (17)	Apigenin-8-C-glucoside (17) [5280441]	-	Antioxidant	-	Borghi et al. (2013)
	Isovitexin (18)	Apigenin-6-C-glucoside (18) [162350]	NMR	Antimicrobial	Methanol:Water/ap	Lin et al. (2002), Choi et al. (2014)
	Luteolin (19)	3′,4′,5,7-tetrahydroxyflavone (19) [5280445]	-	Anti-inflammatory	-	Kim et al. (1999), Lin et al. (2008), Chen et al. (2014)
			-	Antitumoral	-	Lin et al. (2008)
	Cynaroside (20)	luteolin 7-O-glucoside (20) [5280637]	NMR	Antimicrobial, antioxidant	Methanol:Water/ap	Hawas et al. (2008)
						Odontuya et al. (2005)
	Cirsiol (21)	6-Hydroxyluteolin 6,7-dimethyl ether (21) [160237]	-	Antitumoral (acts as radiosensitizer)	-	Kang et al. (2013)
	Genkwanin (22)	4',5-Dihydroxy-7-methoxyflavone (22) [5281617]	HPLC/LC-MS	N/A	Diethyl ether/ap	Grayer et al. (2010)
	Ladanein (23)	scutellarein-5,7,4’-trimethyl ether (23) [3084066]
	Salvigenin (24)	Scutellarein 6,7,4’-trimethylether (24) [161271]		Antioxidant		Grayer et al. (2010)
	Cirsimaritin (25)	Scutellarein 6,7-dimethylether (25) [188323]		N/A		Grayer et al. (2010)
Flavanone	2(S)-4',5-dihydroxy-6,7-dimethoxyflavanone (26)	2(S)-4',5-dihydroxy-6,7-dimethoxyflavanone (26) [14078484]	NMR		Ether/ap	Uchida et al. (1980)
	Quinones
	Ecklonoquinone A (27)	[4,6-dimethyl-7,8-dioxo-1,9-di(propan-2-yl)dibenzo-p-dioxin-2-yl] 3-methylbutanoate (27) [21576878]	NMR	N/A	Ether/ap	Uchida et al. (1980)
	Ecklonoquinone B (28)	[4,9-Dimethyl-7,8-dioxo-1,6-di(propan-2-yl)dibenzo-p-dioxin-2-yl] 3-methylbutanoate (28) [21576879]

N/A, Not Applicable; ap, aerial parts (leaves); wp, the whole plant.

HPLC, High performance liquid chromatography; LC-MS, Liquid Chromatography-Mass Spectrometry; NMR, Nuclear Magnetic Resonance.

^aBiological activity presented in table is related to the compound (can be isolated from P. ecklonii and other species)