The liverwort, Porella vernicosa complex produces a very hot tasting polygodial, a drimane-type sesquiterpene dialdehyde. The same compound has been isolated from two ferns, Thelypteris hispidula and Blechnum fluviatile, as well as from the higher plants Polygonum hydropiper, P. hydropiper f purpurascens (Polygonaceae), Cinnamosma, Caspicodendron, Canella and Warburgia species (Canellaceae), and Pseudowintera colorata, Tasmannia lanceolata, Drimys and Zygogynum species (Winteraceae). In addition, the liverworts and higher plants which elaborate polygodial and its related pungent drimane dials contain a small amount of α-tocopherol, γ-tocopherol or δ-tocotrienol. The present paper gives the results of a comparative study on the drimane-type sesquiterpenoids in some liverworts, ferns and higher plants, and the role of tocopherols in these plant groups.
AsakawaY. (1982) Chemical constituents of the Hepaticae. In Progress in the Chemistry of Organic Natural Products.HerzW, GrisebachH, KirbyGW. (Eds), vol. 42, Springer, Vienna, pp. 1–285.
2.
AsakawaY. (1995) Chemical constituents of the Bryophytes. In Progress in the Chemistry of Organic Natural Products.HerzW, KirbyGW, MooreRE, SteglichW, TammCh. (Eds), vol. 65, Springer, Vienna, pp. 1–618.
3.
AsakawaY, LudwiczukA, NagashimaF. (2012) Chemical constituents of bryophytes. Bio and chemical diversity, biologically activity and chemosystematics. In Progress in the Chemistry of Organic Natural Products. KinghornAD, FolkH, KobayashiJ. (Eds), vol. 95, Springer, Vienna, pp. 1–760.
4.
SocolskyC, MuruagaN, BardonA. (2005) Drimanes and other terpenoids from fern Thelypteris hispidula (Decne.) Reed. Chemistry and Biodiversity, 2, 1105–1108.
5.
NishikiM, PaetzC, BardonA, SocolskyC, ToyotaM, OisoY, AsakawaY. (2005) Pungent components and their related products of Argentinean Polygonum punctatum var. punctatum and Thelypteris hispidula (fern). 49 Kai Koryo Terupen oyobi Seiyu Kagaku ni kansuru Toronkai Koen Yoshishu (49th TEAC Abstract), Fukui, Japan, 230–232.
6.
AsakawaY, ToyotaM, OisoY, BragginsJE. (2001) Occurrence of polygodial and 1-(2,4,6-trimethoxyuphenyl)-but-2-en-1-one from some ferns and liverworts: role of pungent components in bryophytes and pteridophytes evolution. Chemical and Pharmaceutical Bulletin, 49, 1380–1381.
7.
BarnesCS, LoderJB. (1962) The structure of polygodial: a new sesquiterpene dialdehyde from Polygonum hydropiper L. Australian Journal of Chemistry, 15, 322–327.
8.
OhsukaA. (1963) The structure of tadeonal and isotadeonal components of Polygonum hydropiper L. Nippon Kagaku Zasshi, 84, 748–752.
9.
AsakawaY, TakemotoT. (1979) A new norsesquiterpene aldehyde and sesquiterpene hemiactal from the seed of Polygonum hydropiper. Experimentia35, 1420–1421.
10.
FukuyamaA, SatoT, AsakawaY, TakemotoT. (1982) A potent cytotoxic warburganal and related drimane-type sesquiterpenoids from Polygonum hydropiper. Phytochemistry, 21, 2895–2898.
11.
FukuyamaA, SatoT, MiuraI, AsakawaY. (1985) Drimane-type sesqui- and norsesquiterpenoids from Polygonum hydropiper. Phytochemistry, 24, 1521–1524.
MiyazawaM, TamuraN. (2007) Components of the essential oil from sprouts of Polygonum hydropiper L. (‘Benitade’). Flavour and Fragrance Journal, 22, 188–190.
WasmanSQ, MahmoodAA, SalehhuddinH, ZahraAA, SalmahI. (1996) Cytoprotective activities of Polygonum minus aqueous leaf extract on ethanol-induced gastric ulcer in rats. Journal of Medicinal Plants Research, 4, 2658–2665.
16.
BaharumSN, BanawanH, GhaniMA, MustaphaWAW, NoorNM. (2010) Analysis of chemical composition of the essential oil of Polygonum minutus Huds. Using two dimensional gas chromatography-time-for-flight mass spectrometry (GC-TOF MS). Molecules, 15, 7006–7015.
17.
YaacobKB. (1987) Keson oil: a natural source of aliphatic aldehydes. Perfumer & Flavorist, 12, 27–30.
18.
NurulH, RuzitaA, AronalAP. (2010) The antioxidant effects of Cosmos caudatus and Polygonum minutus in refrigerated duck meatballs. International Food Research Journal, 17, 893–904.
19.
AlvesTMA, RibeiroFL, KloosH, ZaniCL. (2001) Polygodial, the fingitoxic component from the Brazilian medicinal plant Polygonum punctatum. Memorio do Instituto Oswald Cruz, 96, 831–833.
20.
HarinantenainaL, TakaokaS. (2006) Cinnafragrins A-C, dimeric and trimeric drimane sesquiterpenoids from Cinnamosma fragrans, and structures revision of capsicodendrin. Journal of Natural Products, 69, 1193–1197.
21.
HarinantenainaL, AsakawaY, ClercqED. (2007) Cinamacrins A-C, cinnafragin D, and cytostatic metabolites with α-glucosidase inhibitory activity from Cinnamosma macrocarpa. Journal of Natural Products, 70, 277–282.
22.
HarinantenainaL, MatsunamiK, OtsukaH, KawahataM, YamaguchiK, AsakawaY. (2008) Secondary metabolites of Cinnamosma madagascariensis and their α-glucosidase inhibitory properties. Journal of Natural Products, 71, 123–126.
23.
KuboI, MatsumotoT, KakookaAB, MubiruNK. (1983) Structure of mukaadial, a molluscicide from Warburgia plants. Chemistry Letters, 7, 979–980.
24.
KuboI, TaniguchiM. (1988) Polygodial, an antifungal potentiator. Journal of Natural Products, 51, 22–29.
25.
KioyD, GrayAI, WatermanPG. (1990) A comparative study of the stem-bark drimane sesquitepene and volatile oils of Warburgia ugandensis and W. stuhlmannii. Phytochemsitry, 29, 3535–3538.
26.
MshimbyeMJ, MaumelaMC, DrewesSE. (1999) Novel and bioactive metabolites of Warburgia salutaris indigenous to the northern province, South Africa. Nigerian Journal of Natural Products and Medicine, 3, 28–30.
27.
MshimbyeMJ, MaumelaMC, DrewesSE. (1999) A drimane sesquiterpenoid lactone from Warburgia slutaris. Phytochemistry, 51, 435–438.
28.
RabeT, van StadenJ. (2000) Isolation of an antibacterial sesquiterpenoid from Warburgia salutaris. Journal of Ethonopharmacology, 73, 171–174.
29.
OlilaD, Opuda-AsiboJ, OdyekO. (2001) Bioassay-guided studies on the cytotoxic and in vitro trypanocidal activities of a sesquiterpene (muzigadial) derived from a Ugandan medicinal plant (Warburgia ugandesis). African Health Sciences, 1, 12–15.
30.
WubeAA, BucarF, GibbonsS, AsresK. (2005) Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. Phytochemistry, 66, 2309–2315.
31.
KuglerovaM, TesarovaH, GradeJ, HalamovaK, Wanyana-MaganyiO, van DammeP, KokoskaL., (2011) Antimicrobial and antioxidative effects of Ugandan medicinal barks. African Journal of Biotechnology, 10, 3628–3632.
32.
MahmoudII, KinghornAD, CordellGA, FarnsworthNR. (1980) Potential anticancer agents. XVI. Isolation of bicyclofarnesane sesquiterpenoids from Caspicodendron dinisii. Journal of Natural Products, 43, 365–371.
33.
BastosJK, KaplanMAC, GottliebOR. (1999) Drimane-type sesquiterpenoids as chemosystematic markers of Canellaceae. Journal of Brazilian Chemical Society, 10, 136–139.
YingB-P, PeiserG, JiY-Y, MathiasKM, KarasinaF, HwangY-S. (1995) Structure-activity relationship of phytotoxic sesquiterpenoids from Canella winterana. Journal of Agricultural and Food Chemistry, 43, 826–829.
36.
LoderJW. (1962) Occurrence of the sesquiterpenes polygodial and guaiol in the leaves of Drimys lanceolata (Poir.) Baill. Australian Journal of Chemistry, 15, 389–390.
37.
ReadC, MenaryR. (2000) Analysis of the contents of oil cells in Tasmannia lanceolata (Poir.) A. C. Smith (Winterceae). Annals of Botany, 86, 1193–1197.
38.
AppelHH, BondRPM, OvertonKH. (1963) Sesquiterpenoids-III. The constitution and stereochemistry of valdiviolide, fuegin, winterin and futronolide. Tetrahedron, 19, 635–641.
ChoudharyRK, OhS, LeeJ. (2011) An ethnomedicinal inventory of knotweeds of Indian Himalaya. Journal of Medicinal Plants Research, 5, 2095–2103.
41.
BurkillJH. (1966) Dictionary of economic products of the Malay peninsula, Art Printing works, Kuala Lumpur, Malaysia, Vol. 2, p. 1823.
42.
Oliveira-SimoesCM, Ribeiro-do-ValeRM, PoliA, NicolauM, ZaniM. (1989) Pharmacological investigation of Polygonum punctatum Elliott (=P. acre H. B. K.) extracts. Part I. Tests in vivo. Journal de pharmacie de Belgique, 44, 275–284.
43.
AlloucheN, APelC, MarinM-T, DumontetV, GueritteF, LitaudonM. (2009) Cytotoxic sesquiterpenoids from Winteraceae of Caledonia rainforest. Phytochemistry, 70, 546–553.
44.
McCallionRF, ColeALJ, WalkerJRL, BluntJW, MunroMHG. (1982) Antibiotic substances from New Zealand. II. Polygodial, an anti-Candida agent form Pseudowintera colorata. Planta Medica, 44, 134–138.
45.
WebbC, JohnsonP, SykesB (1990) Flowering plants of New Zealand. DSIR Botany, Christchurch, New Zealand, p. 104.
46.
MalheirosA, FilhoVC, SchmittCB, SantosARS, ScheidtC, CalixtoJB, MonacheFD, YunesRA. (2001) A sesquiterpene drimane with antinociceptive activity from Drimys winteri bark. Phytochemsitry, 57, 103–107.
47.
GerardPJ, PerryNB, RufLD, FosterLM. (1993) Antifeedant and insecticidal activity from Pseudowintera colorata (Winteraceae) on the webbing clothes moth, Tineola bisselliella (Lepodoptera:Tineidae) and the Australian carpet beetle, Anthrenocerus australis (Coleoptera: Dermestidae). Bulletin of Entomological Research, 83, 547–552.
48.
PerryNB, GouldKS. (2010) Hot chemistry from Horopito. Chemistry in New Zealand145–148.
49.
Forest Herbs Research, Scientific Summary Version 7 (August 2011). P. 1–15.
50.
HaraguchiH, OhmiI, SakaiS, FukudaA. (1996) Effect of Polygonum hydropiper sulfated flavonoids on lens aldose reductase and related enzymes. Journal of Natural Products, 59, 443–445.
51.
OnoK, NakaoM, ToyotaM, TerashiY, YamadaM, KohnoT, AsakawaY. (1998) Catechin production in cultured Polygonum hydropiper cells. Phytochemistry, 49, 1935–1939.
PengZF, StackD, BaumertA, SubramaniamR, GohNK, ChiaTF, TanSN, ChiaLS. (2003) Antioxidant flavonoids from leaves of Polygonum hydropiper. Phytochemistry, 62, 219–228.
54.
KuboI, LeeY-W, PetteiM, PilkiewiczF, NakanishiK. (1976) Potent army worm antifeedants from the East African Warburgia plants. Journal of the Chemical Society, Chemical Communication, 24, 1013–1014.
FurutaT, FukuyamaA, AsakawaY. (1986) Polygonolide, an isocoumarin from Polygonum hydropiper possessing anti-inflammatory activity. Phytochemistry, 25, 517–520.
57.
StarkenmannC, LucaL, NiclassY, PrazE, RoguetD. (2006) Comparison of volatile constituents of Persicaria odorata (Lour.) Sojak (Polygonum odoratum Lour.) and Persicaria hydropiper (L. Spach) (Polygonum hydropiper L). Journal of Agricultural and Food Chemistry, 54, 3067–3071.
58.
AsakawaY, ToyotaM, NagashimaF, HashimotoT, HassaneLE. (2000) Sesquiterpene lactones and acetogenin lactones from the Hepaticae and chemosystematics of the liverworts Frullania, Plagiochila and Porella. Heterocycles, 54, 1057–1093.
KomalaI, ItoT, NagashimaF, YagiY, AsakawaY. (2010) Cytotoxic, radical scavenging and anti-microbial activities of sesquiterpenoids from the Tahitian liverwort Mastigophora diclados (Bird.) Nees (Mastigophoraceae). Journal of Natural Medicine, 64, 417–422.
61.
HarriganGG, BajAN, GlassTE, GunatilakaAAL, KingstonDGI. (1993) Bioactive and other sesquiterpenoids from Porella cordaeana. Journal of Natural Products, 56, 921–925.
62.
RodriguezB, ZapataN, MedinaP, VinuelaE. (2005) A completely 1H and 13C NMR data assignment for four drimane sesquiterpenoids isolated from Drimys winteri. Magnetic Resonance in Chemistry, 43, 82–84.
63.
WaymanK, de LangePJ, LarsenL, SansomCE, PerryNB. (2010) Chemotaxonomy of Pseudowintera: sesquiterpene dialdehydes variants are species markers. Phytochemistry, 71, 766–772.
64.
OkudaRK, ScheuerPJ, HochlowskiJE, WalkerRP, FaulknerDJ. (1983) Sesquiterpenoid constituents of eight prostaome nudibranchs. Journal of Organic Chemistry, 48, 1866–1869.
65.
PengZF, StrackD, BaumertA, SubramanianR, GohNK, ChiaTF, TanSN, ChiaLS. (2003) Antioxidant flavonoids from leaves of Polygonum hydropiper. Phytochemistry, 62, 219–228.
66.
HasanMF, KhanA, HossainMS, RahmanM. (2009) The determination of antibacterial and antifungal activities of Polygonum hydropiper (L.) root extract. Advances in Biological Research, 3, 53–56.
67.
KuboI, FujitaK, LeeSH. (2001) Antifungal mechanism of polygodial. Journal of Agricultural and Food Chemistry, 49, 1607–1611.
68.
XuM, LitaudonM, KriefS, MartinM-T, KaseneneJ, KiremireB, DumontetV, GueritteF. (2009) Ugadenial A, a new drimane-type sesquiterpenoid from Warburgia ugandensis. Molecule, 14, 3844–3850.
69.
AsakawaY, DawsonGW, GriffithsDC, LallemandJ-Y, LeySV, MoriK, MuddA, Pezechk-LecclaireM, PickettJA, WatanabeH, WoodcockCM, Zong-NingZ. (1988) Activity of drimane antifeedants and related compounds against aphids, and comparative biological effects and chemical reactivity of (-)- and (+)-polygodial. Journal of Chemical Ecology, 14, 1845–1855.
70.
KonigWA, JoulainD, HochmuthDH. (2008) Mass Finder 4.0, Terpenoids and related constituents of essential oils. Available from: http://www.massfinder.com/.
