Natural Product Polyphenols of Relevance to Human Health

Figures & data

Figure 1 Phenolic acids and derivatives.

Figure 2 Basic flavonoid structure.

Figure 3 Representative structures of stilbenes and lignans.

Table 1 Potential chemopreventive agents isolated from edible plants.

Latin name	Compound	Activity	References
Broussonetia papyrifera (L.) Venten	3′-[γ-Hydroxymethyl-(E)-γ-methylallyl]-2,4,2′,4′-tetrahydroxychalcone 11′-O-coumarate (2S)-2′,4′-Dihydroxy-2′′(1-hydroxy-1-methylethyl)dihydrofuro[2,3-h]flavanone Isolicoflavonone (2S)-Abyssinone II	AE	Lee et al. (2001c)
Casimiroa edulis Llav. et Lex	Zapotin 2′,5,6-Trimethoxyflavone	HL-60	Mata-Greenwood et al. (2001)
Cerbera manghas L.	( − )-14-Hydroxy-3β-(3-O-methyl-6-deoxy-α-l-rhamnosyl)-11α, 12α-epoxy-(5β, 14β,17βH)–card-20(22)-enolide ( − )-14-Hydroxy-3β-(3-O-methyl-6-deoxy-α-l-glucopyranosyl)-11α, 12α-epoxy-(5β, 14β,17βH)–card-20(22)-enolide ( − )-17β-Neriifolin	AE	Chang et al. (2000a)
Cotinus coggygria Scop.	Disulfuretin, sulfuretin, sulfurein Gallic acid, methyl gallate Pentagalloyl glucose	AO	Westenburg et al. (2000)
Eugenia sandwicensis Gray	Gallic acid 3β-trans-p-coumaroyloxy-2α,23-dihydroxyolean-12-en-28-oic acid	AO MMOC	Gu et al. (2001)
Isodon excisus var coreanus Nakai	Inflexin Ursolic acid Ursolic acid 3-O-acetate	AE	Jeong et al. (2000)
Physalis philadelphica Lam.	2,3-Dihydro-3-methoxywithaphysacarpin Withaphysacarpin 24,25-Dihydrowithanolide	QR	Kennelly et al. (1997)
	Philadelphicalactone A/B Ixocarpalactone A/B 18-Hydroxywithanolide D Withanone	QR	Su et al. (2002b)
Tephrosia purpurea Pers.	7,4′ -Dihydroxy-3′,5′ -dimethoxyisoflavone ( + )-Tephropurpurin, ( + )-purpurin Pongamol, lanceolatin ( − )-Maackiain, ( − )-medicarpin ( − )-3-Hydroxy-4-methoxy-8,9-methylene- dioxypterocarpan	QR	Chang et al. (1997)
Thuja occidentalis L.	( + )-7-Oxo-13-epi-pimara-14,15-dien-18-oic acid ( + )-7-Oxo-13-epi-pimara-8,15-dien-18-oic acid ( + )-Isopimaric acid (1S,2S,3R)-( + )-Isopicryodeoxypodophyllotoxin ( − )-Deoxypodophyllotoxin ( − )-Deoxypodorhizone	ODC	Chang et al. (2000b)

AE, antiestogenic activity; AO, antioxidant activity; ODC, ornithine decarboxylase inhibitor; QR, quinone reductase inducer; HL-60, HL-60 cell differentiation inducer; MMOC, mouse mammary organ culture.

Table 2 Chemopreventive medicinal plants reported in animal carcinogenesis models.

Latin name (common name)	Active component/biological activity	References
Ajuga decumbens Thunb.	8-Acetylharpagide Inhibition of two stage mouse skin carcinogenesis and mouse pulmonary tumor	Takasaki et al. (1999b); Konoshima et al. (2000)
Aloe barbadensis Miller	Polysaccharide Inhibition of BP-DNA adduct formation Inhibition of ODC activity Inhibition of tyrosine kinase activity	Kim et al. (1999); Kim and Lee (1997)
Apium graveolens L. (celery seed oil)	p-Mentha-2,8-dien-1-ol, 3-n-butyl phthalide, sedanolide Induce GST Inhibition of BP-induced stomach cancer	Zheng et al. (1993)
Asteracantha longifolia Aees.	Methanol extract of seed Inhibition of hepatocarcinogenesis in Wistar rats Increase GPx and CAT, ODC	Ahmed et al. (2001)
Bolbostemma paniculatum (Maxim.) Franquet	Tubeimoside I and tubeimoside III Antitumor promotion activity against TPA	Yu et al. (1995)
Calophyllum inophyllum L.	Calocoumarin-A Inhibition of two-stage mouse skin carcinogenesis	Itoigawa et al. (2001)
Chelidonium majis L.	Inhibition of MNNG-induced glandular stomach carcinogenesis	Kim et al. (1997)
Coleogyne ramosissima Torr. Cowania mexicana D. Don.	Polyphenols Inhibition of two stage mouse skin carcinogenesis	Ito et al. (1999)
Coptis japonica (Thunb.) Makino	Inhibition of AOM-induced ACF	Fukutake et al. (1998)
Eucalyptus grandis Hill ex Maiden	Euglobal-G1(phloroglucinol-monoterpene) Inhibition of two-stage mouse skin carcinogensis Inhibition of 4-NQO–induced mouse pulmonary tumor	Takasaki et al. (2000); Takasaki et al. (1995)
Ferula narthex Boiss.	Antioxidant and inhibition ODC activity	Saleem et al. (2001f)
Ganoderma lucidum Karst.	GST induction Inhibition of lipid peroxidation and oxidative DNA damage	Kim et al. (1999); Lee et al. (2001)
Hibiscus sabdariffa L.	Antimutagenicity in Salmonella mutation assay	Chewonarin et al. (1999)
Ocimum sanctum L.	Extract of leaves Induce GST	Banerjee et al. (1996)
Picrorhiza kurroa Royle ex Benth.	Picroliv (iridoid glycoside mixture) Inhibition of 3-MC-induced sarcoma and DMBA-induced papilloma	Rajeshkumar and Kuttan (2001)
Scutellaria baicalensis Georgi	Inhibition of AOM-induced ACF	Fukutake et al. (1998)
Semecarpus anacardium L.	Antioxidant	Premalatha and Sachdanandam (1999)
Taraxacum japonicum Koidz	Inhibition of two-stage mouse skin carcinogenesis	Takasaki et al. (1999a)
Wistaria brachybotrys Sieb et Zucc.	Pendulon Inhibition of two-stage mouse skin carcinogenesis	Konoshima et al. (1997)

ACF, aberrant crypt foci; AOM, azoxymethane; BP CAT, catalase; GPx, glutathione peroxidase; GST, glutathione transferase; 23-MC, 3-methylcholanthrene; MNNG, N-methyl-N′-nitro-N-nitrosoguanidine; 4-NQO, 4-nitroquinoline-N-oxide; ODC, ornithine decarboxylase.

Table 3 Potential chemopreventive agents isolated from medicinal plants.

Latin name	Compound	Activity	References
Acnistus arborescens (L.) Schltdl.	7β-Acetoxywithanolide D 7β,16α-Diacetoxywithanolide D 4-Deoxy-7β,16α-diacetoxywithanolide D	QR	Minguzzi et al. (2002)
Aglaia ponapensis Kanehira	Desmethylrocaglamide	HL-60	Mata-Greenwood et al. (2001)
Aiphanes aculeate Willd.	Aiphanol	COX	Lee et al. (2001d)
Antirhea acutata (DC) Urb.	(6S)-Hydroxy-29-nor-3,4-seco-cycloart-4(30),24-dien-3-oic acid 8-[1-(3,4-Dihydroxyphenyl)-3-methoxy-3-oxopropyl]epicatechin	COX AO	Lee et al. (2001e)
Brassica campestris L.	Brassinin	QR	Gerhäuser et al. (1997a)
Brucea javanica (L.) Merr.	Yadanziolide S Flazin Bruceine Yadanxioside Bruceoside A Yadanzioside F	HL-60 COX MMOC	Su et al. (2002a)
	Guaiacylglycerol-β-O-6′ -(2-methoxy)cinnamyl alcohol Brusatol Dehydrobrusato Yadanziolide C Blumenol A	HL-60	Luyengi et al. (1996)
Chorizanthe diffusa Benth.	5,8,3′,4′,5′ -Pentahydroxy-3,7-dimethylflavone 5,7,3′,4′ -Tetrahydroxy-3-methylflavone 5,8,3′,4′ -Tetrahydroxy-3,7-dimethylflavone Quercetin 3′′ -O-Acetylquercetin	AO MMOC	Chung et al. (1999)
Daphniphyllum calycinum Benth.	5,6,7,4′ -Tetrahydroxyflavonol-3-O-rutinoside 3-O-Neopesperidoside	AO	Gamez et al. (1998)
Mundulea sericea (Willd.) A.Chev.	Deguelin	ODC	Udeani et al. (1997); Gerhäuser et al. (1997b)
	Munetone	ODC	Lee et al. (1999a)
Pachysandra procumbens Michx.	( − )-Pachyaximine A ( + )-Pachysamine B ( + )-(20S)-S-(Benzoylamino)-20-(dimethylamino-5α-pregn-2-en-4β-yl acetate	AE	Chang et al. (1998)
Petiveria alliacea L.	Dibenzyltridulfide 2-[(Phenylmethylditho)ethanol	HL-60	Mata-Greenwood et al. (2001)

AO, antioxidant activity; AE, anti-estrogenic activity; COX, cyclooxygenase inhibitor; ODC, ornithine decarboxylase inhibitor; QR, quinone reductase inducer; HL-60, HL-60 cell differentiation inducer; MMOC, mouse mammary organ culture.

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