Selection of chemical markers for the quality control of medicinal plants of the genus Cecropia

Figures & data

Table 1. Compounds in Cecropia sp. with Herb Mars score on potential biological activities.

Compound	Plant species	Plant part	Concentration	Biological activity	Ranking score	Standard available	References
Phenolic acids
Chlorogenic acid	C. obtusifolia	Leaves	DL↑, AE↑, BuE ↑	Anti-diabetic	5	Y	(Andrade-Cetto & Wiedenfeld 2001; Andrade-Cetto & Heinrich 2005; Revilla-Monsalve et al. 2007; Alonso-Castro et al. 2008; Andrade-Cetto et al. 2008)
	C. obtusifolia y C. peltata	Leaves	ME↑	Anti-diabetic	5	Y	(Nicasio et al. 2005; Andrade-Cetto et al. 2007)
	C. glaziovii	Leaves	AE↑	Anti-inflammatory, anti-hypertensive	5	Y	(Tanae et al. 2007; Costa et al. 2011a; Müller et al. 2016)
	C. pachystachya	Leaves	DL↑, ME↑, AE↑	Anti-diabetic, anti-inflammatory, wound healing, leishmanicidal, neuroprotective, QS inhibitor	5	Y	(Aragão et al. 2010; Costa et al. 2011a; Cruz et al. 2013; Gazal et al. 2014; Maquiaveli et al. 2014; Pacheco et al. 2014; Gazal et al. 2015; Duque et al. 2016; Ortmann et al. 2016)
	C. hololeuca	Leaves	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
Caffeic acid	C. glaziovii	Leaves	EtE↓	NR	1	Y	(Arend et al. 2011)
Vanillic acid	C. obtusifolia	Leaves	DCME↑	Anti-inflammatory	0	Y	(Guerrero et al. 2010; Kim et al. 2011)
Flavonoids
Isoorientin	C. obtusifolia	Leaves	DL↑, AE↑, BuE↑	Anti-diabetic	5	Y	(Andrade-Cetto & Wiedenfeld 2001; Revilla-Monsalve et al. 2007; Andrade-Cetto et al. 2008)
	C. peltata	Leaves	NR	Anti-diabetic	1	Y	(Andrade-Cetto et al. 2007)
	C. glaziovii	Leaves	AE↑	Anti-inflammatory, anti-hypertensive, anti-ulcer and anti-secretory gastric activities	5	Y	(Tanae et al. 2007; Souccar et al. 2008; Costa et al. 2014; Müller et al. 2016)
		Stipules	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
	C. pachystachya	Leaves	DL↑, ME↑, AE↑	Anti-diabetic, anti-inflammatory, anti-depressant, wound healing, neuroprotective, QS inhibitor	5	Y	(Oliveira et al. 2003; Chanmahasathien et al. 2004; Aragão et al. 2010; Costa et al. 2011a; Brango-Vanegas et al. 2014; Gazal et al. 2014; Pacheco et al. 2014; Gazal et al. 2015; Duque et al. 2016; Ortmann et al. 2016)
	C. hololeuca	Leaves	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
Orientin	C. glaziovii	Leaves	AE↑	Anti-hypertensive, anti-ulcer and anti-secretory gastric activities	5	Y	(Tanae et al. 2007; Souccar et al. 2008)
	C. pachystachya	Leaves	DL↑, ME↑, AE↑	Anti-diabetic, anti-inflammatory, anti-depressant, wound healing, leishmanicidal, neuroprotective, QS inhibitor	5	Y	(Chanmahasathien et al. 2004; Aragão et al. 2010; Costa et al. 2011a; Cruz et al. 2013; Brango-Vanegas et al. 2014; Gazal et al. 2014; Maquiaveli et al. 2014; Pacheco et al. 2014; Gazal et al. 2015; Duque et al. 2016; Ortmann et al. 2016)
	C. hololeuca	Leaves	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
Isovitexin	C. glaziovii	Leaves	AE↑	Anti-inflammatory, anti-hypertensive, anti-ulcer and anti-secretory gastric activities	5	Y	(Tanae et al. 2007; Souccar et al. 2008; Costa et al. 2011a; 2014)
	C. pachystachya	Leaves	ME↑ AE↑	Anti-depressant, leishmanicidal, neuroprotective, QS inhibitor	5	Y	(Lacaille-Dubois et al. 2001; Costa et al. 2011a; Brango-Vanegas et al. 2014; Gazal et al. 2014; 2015; Ortmann et al. 2016)
Vitexin	C. pachystachya	Leaves	DL↓ ME↓	Anti-inflammatory, QS inhibitor	3	Y	(Chanmahasathien et al. 2004; Brango-Vanegas et al. 2014)
Rutin	C. pachystachya	Leaves	DL↓ ME↑	Anti-inflammatory, QS inhibitor	5	Y	(Chanmahasathien et al. 2004; Brango-Vanegas et al. 2014)
Isoquercitrin	C. glaziovii	Stipules and leaves	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
	C. pachystachya	Leaves	NR	Leishmanicidal, neuroprotective, anti-depressant	1	Y	(Lacaille-Dubois et al. 2001; Cruz et al. 2013; Gazal et al. 2014; 2015; Ortmann et al. 2016)
Quercetin	C. pachystachya	Leaves	NR	Leishmanicidal	1	Y	(Cruz et al. 2013)
Apigenin	C. pachystachya	Leaves	NR	Leishmanicidal	1	Y	(Cruz et al. 2013)
Apigenin-6-galactosyl-6′′-O-galactopyranoside	C. pachystachya	Leaves	DL↓	NR	0	N	(Oliveira et al. 2003)
Luteolin	C. pachystachya	Leaves	NR	Leishmanicidal	1	Y	(Cruz et al. 2013)
Catechin	C. glaziovii	Leaves	AE ↑ (Tanae et al. 2007)	Anti-hypertensive, anti-depressant-like effect, anti-ulcer and anti-secretory gastric activities	5	Y	(Rocha et al. 2007; Tanae et al. 2007; Souccar et al. 2008)
		Stipules	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
	C. pachystachya	Leaves	NR	Anti-hypertensive, leishmanicidal	1	Y	(Lacaille-Dubois et al. 2001; Cruz et al. 2013)
	C. hololeuca	Leaves	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
Epicatechin	C. glaziovii	Leaves	AE ↑	Anti-hypertensive, anti-ulcer and anti-secretory gastric activities	5	Y	(Tanae et al. 2007; Souccar et al. 2008)
		Stipules	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
	C. pachystachya	Leaves	NR	Anti-hypertensive, leishmanicidal	1	Y	(Lacaille-Dubois et al. 2001; Cruz et al. 2013)
	C. hololeuca	Leaves	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
Procyanidin B2	C. glaziovii	Leaves	AE ↑	Anti-hypertensive, anti-depressant-like effect, anti-ulcer and anti-secretory gastric activities	5	Y	(Rocha et al. 2007; Tanae et al. 2007; Souccar et al. 2008)
		Stipules	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
	C. pachystachya	Leaves	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
	C. hololeuca	Leaves	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
Procyanidin B3 isomer	C. glaziovii	Leaves	AE↑	Anti-hypertensive, anti-depressant-like effect, anti-ulcer and anti-secretory gastric activities	0	N	(Rocha et al. 2007; Tanae et al. 2007; Souccar et al. 2008)
Procyanidin B5	C. glaziovii	Leaves	AE↑	Anti-hypertensive, anti-ulcer and anti-secretory gastric activities	5	Y	(Tanae et al. 2007; Souccar et al. 2008)
Procyanidin C1	C. glaziovii	Leaves	AE↑	Anti-hypertensive, anti-ulcer and anti-secretory gastric activities	5	Y	(Tanae et al. 2007; Souccar et al. 2008)
		Stipules	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
	C. hololeuca	Leaves	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
Protocatechuic acid	C. pachystachya	Leaves	NR	NR	1	Y	(Lacaille-Dubois et al. 2001)
	C. hololeuca	Leaves	NR	Anti-hypertensive	1	Y	(Lacaille-Dubois et al. 2001)
Terpenic and steroidal compounds
2-α-Acetoxy-3β,19α -dihydroxy-11α,12α -epoxy-ursan-28,13β-olide	C. pachystachya	Roots	DL↓	NR	0	N	(Machado et al. 2008)
2-α-Acetyl tormentic acid	C. pachystachya	Roots	NR	Cytotoxic	0	N	(Rocha et al. 2007, 2012a)
2-O-Acetyl euscaphic acid	C. pachystachya	Roots	DL↑	NR	0	N	(Machado et al. 2008)
3-β-Acetoxy-2α,19α-dihydroxy-11α,12α-epoxy-ursan-28,13β-olide	C. pachystachya	Roots	DL↓	NR	0	N	(Machado et al. 2008)
3-β-Acetyl tormentic acid	C. pachystachya	Roots	DL↓	Cytotoxic	0	N	(Oliveira et al. 2005; Rocha et al. 2007, 2012a)
4,22-Cholestadien-3-one	C. obtusifolia	Leaves	DCME↑	NR	0	N	(Guerrero et al. 2010)
4-Cholestene-3,24-dione	C. obtusifolia	Leaves	DCME↑	NR	0	N	(Guerrero et al. 2010)
α-Amyrin	C. pachystachya	Leaves	DL↑, DCME↑	Anti-inflammatory	5	Y	(Schinella et al. 2008)
β-Sitosterol	C. obtusifolia	Leaves	NR	Anti-inflammatory	1	Y	(Andrade-Cetto & Heinrich 2005; Loizou et al. 2010)
	C. pachystachya	Leaves	DL↑, DCME↑	Anti-inflammatory	5	Y	(Hikawczuk et al. 1998; Schinella et al. 2008)
Euscaphic acid	C. pachystachya	Roots	DL↓	Cytotoxic	0	Y	(Oliveira et al. 2005; Rocha et al. 2007, 2012a)
Isoarjulonic acid	C. pachystachya	Roots	DL↓	NR	0	N	(Oliveira et al. 2005)
Oleanolic acid	C. pachystachya	Leaves	NR	Anti-inflammatory	1	Y	(Hikawczuk et al. 1998)
Pomolic acid	C. pachystachya	Leaves	DL↑ DCME↑	Anti-inflammatory	5	Y	(Schinella et al. 2008)
Stigmast-4-en-3-one	C. obtusifolia	Leaves	DCME↑	Anti-inflammatory, anti-diabetic	1	Y	(Jamaluddin et al. 1995; Alexander-Lindo et al. 2004; Guerrero et al. 2010; Tewtrakul et al. 2010)
Stigmasterol	C. obtusifolia	Leaves	NR	Anti-inflammatory	1	Y	(Andrade-Cetto & Heinrich 2005; Gabay et al. 2010)
Tormentic acid	C. pachystachya	Root-wood	DL↑ EtE↑	Anti-inflammatory, anti-malaric and cytotoxic	5	Y	(Oliveira et al. 2005; Rocha et al. 2007, 2012a; Uchoa et al. 2010)
Ursolic acid	C. pachystachya	Leaves	DL↑ DCME↑	Anti-inflammatory	5	Y	(Schinella et al. 2008)
Anthraquinones
Aloe-emodin	C. obtusifolia	Leaves	NR	Anti-inflammatory	1	Y	(Choi et al. 2013; Yan et al. 2013; Kshirsagar et al. 2014; Park et al. 2016)
Chrysophanol	C. obtusifolia	Leaves	NR	Anti-inflammatory	1	Y	(Choi et al. 2013; Yan et al. 2013; Kshirsagar et al. 2014; Park et al. 2016)
Emodin	C. obtusifolia	Leaves	NR	Anti-inflammatory	1	Y	(Choi et al. 2013; Yan et al. 2013; Kshirsagar et al. 2014; Park et al. 2016)
Physcion	C. obtusifolia	Leaves	NR	Anti-inflammatory	1	Y	(Choi et al. 2013; Yan et al. 2013; Kshirsagar et al. 2014; Park et al. 2016)
Rehin	C. obtusifolia	Leaves	NR	Anti-inflammatory	1	Y	(Choi et al. 2013; Yan et al. 2013; Kshirsagar et al. 2014; Park et al. 2016)
Other compounds
1-(2-Methyl-1-nonen-8-il)-aziridine	C. obtusifolia	Leaves	NR	NR	0	N	(Andrade-Cetto & Heinrich 2005)
2-Methylbenzaldehyde	C. obtusifolia	Leaves	DCME↑	NR	0	N	(Guerrero et al. 2010)
2,3-Dihydrobenzofuran	C. obtusifolia	Leaves	DCME↑	NR	0	Y	(Guerrero et al. 2010)
3′-Methoxyacetophenone	C. obtusifolia	Leaves	DCME↑	NR	0	Y	(Guerrero et al. 2010)
4-Ethyl-5-(n-3valeroil)-6-hexahy- drocoumarin	C. obtusifolia	Leaves	NR	NR	0	N	(Andrade-Cetto & Heinrich 2005)
4-Vinyl-2-methoxy-phenol	C. obtusifolia	Leaves	DCME↑	NR	0	Y	(Guerrero et al. 2010)
Palmitic acid	C. obtusifolia	Leaves	DCME↑	Anti-inflammatory	1	Y	(Guerrero et al. 2010; Aparna et al. 2012)
Stearic acid	C. obtusifolia	Leaves	DCME↑	Anti-inflammatory	1	Y	(Guerrero et al. 2010; Pan et al. 2010)
trans-Phytol	C. pachystachya	Leaves	DL↑, DCME↑	Anti-inflammatory	5	Y	(Schinella et al. 2008)

DL: Dried material; AE: aqueous extract; BuE: butanolic extract; ME: methanolic extract; DCME: dichloromethane extract; HE: hexane extract; NR Not reported. Too low concentration (↓↓): <5 μg/g in the herb or finished product. Low concentration (↓): 5-50 μg/g in the herb or finished product. Relative high concentration (↑): >50 μg/g in the herb or finished product..

Figure 1. Chemical structures of selected markers: chlorogenic acid (1), isoorientin (2), orientin (3), isovitexin (4), vitexin (5), rutin (6), catechin (7), epicatechin (8), procyanidin B2 (9), procyanidin B5 (10), procyanidin C1 (11), β-sitosterol (12), α-amyrin (13), pomolic acid (14), tormentic acid (15), ursolic acid (16).

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