Comment on Pyrrolizidine Alkaloids and Terpenes from Senecio (Asteraceae): Chemistry and Research Gaps in Africa
Abstract
1. Introduction
2. Phytochemistry of African Senecio
3. Conclusions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Species and Author | Y/N | Species and Author | Y/N | Species and Author | Y/N |
---|---|---|---|---|---|
S. abbreviatus S.Moore | N | S. glutinosus Thunb. | Y | S. paniculatus P.J. Bergius | Y |
S. abruptus Thunb. | N | S. gossweileri Torre | N | S. parascitus Hilliard | N |
S. acetosifolius Baker | N | S. gossypinus Baker | Y | S. parentalis Hilliard and B.L. Burtt | N |
S. achilleifolius DC. | N | S. gramineticola C. Jeffrey | N | S. parvifolius DC. (Synonym of S. carroensis) | N |
S. actinoleucus F.Muell. | N | S. gramineus Harv. | N | S. paucicalyculatus Klatt | Y |
S. acutifolius DC. | N | S. grandiflorus P.J. Bergius | Y | S. pauciflorus Baker | N |
S. adenostylifolius Humbert | N | S. gregatus Hilliard | N | S. pauciflosculosus C. Jeffrey | N |
S. adnatus DC. | Y | S. hadiensis Forssk. | Y | S. pearsonii Hutch. (Synonym of S. asperulus) | N |
S. adscendens (syn. andinus) Bojer | N | S. halimifolius L. | Y | S. pellucidus DC. | N |
S. aegyptius L. | Y | S. harveyanus MacOwan | N | S. peltophorus Brenan | N |
S. aequinoctialis R.E.Fr. | N | S. hastatus L. (Synonym of S. erosus and S. robertiifolius) | N | S. penninervius DC. | N |
S. aetfatensis B.Nord. | N | S. hastifolius (L.f.) Less. | N | S. pentactinus Klatt | N |
S. affinis DC. | Y | S. haygarthii M.Taylor ex Hilliard | N | S. pentecostus Hiern | N |
S. agapetes C.Jeffrey | N | S. hebdingii (Rauh and Buchloh) G.D. Rowley | N | S. perralderianus Coss. | N |
S. albanensis DC. | N | S. hedbergii C. Jeffrey | N | S. perrieri Humbert | N |
S. albanopsis Hilliard | N | S. hederiformis Cron | N | S. perrottetii DC. | N |
S. albifolius DC. | N | S. heliopsis Hilliard and B.L. Burtt | Y | S. persicifolius L. | N |
S. albopunctatus Bolus | N | S. helminthioides (Sch.Bip.) Hilliard | Y | S. petiolaris DC. | N |
S. aloides DC. | N | S. hermannii B. Nord. | N | S. petraeus Boiss. and Reut. | N |
S. altissimus Mill. | N | S. hesperidum Jahand, Maire, and Weiller | N | S. phalacrolaenus DC. | N |
S. ambositrensis Humbert | N | S. hieracioides DC. | Y | S. pillansii Levyns | N |
S. amplificatus C.Jeffrey | N | S. hildebrandtii Baker | N | S. pinifolius (L.) Spreng. | N |
S. anapetes C.Jeffrey | N | S. hirsutilobus Hilliard | N | S. pinnatifidus Less. | N |
S. andapensis Humbert | N | S. hirtifolius DC | N | S. pinnatipartitus Sch.Bip. ex Oliv. | N |
S. andohahelensis Humbert | N | S. hirto-crassus Humbert | N | S. pinnulatus Thunb. | N |
S. angulatus L.f. | Y | S. hochstetteri Sch.Bip. Ex A.Rich. | N | S. piptocoma O.Hoffm. | N |
S. angustifolius (Thunb.) Willd. | Y | S. hoggariensis Batt. and Trab. | Y | S. pirottae Chiov. | N |
S. anomalochrous Hilliard | N | S. hollandii Compton | N | S. plantagineoides C. Jeffrey | N |
S. antaisaka Humbert | N | S. holubii Hutch. and Burtt Davy | N | S. pleistophyllus C. Jeffrey | N |
S. antambolorum Humbert | N | S. humidanus C. Jeffrey | N | S. poggeanus Mattf. | N |
S. antandroi Scott Elliot | N | S. hypochoerideus DC. | Y | S. polelensis Hilliard | N |
S. anthemifolius Harv. | N | S. ilicifolius Thunb. | Y | S. polyadenus Hedberg | N |
S. antitensis Baker | N | S. ilsae A.Santos and ReY-Bet | N | S. polyanthemoides Sch.Bip. | Y |
S. aquifoliaceus DC. | N | S. immixtus C. Jeffrey | N | S. polyodon DC. | N |
S. arabidifolius O.Hoffm | N | S. inaequidens DC. | Y | S. poseideonis Hilliard and B.L. Burtt | N |
S. arenarius Thunb. | N | S. incomptus DC. | N | S. praeteritus Killick | N |
S. arniciflorus DC | N | S. incrassatus Lowe | N | S. propior S. Moore | N |
S. asperulus DC | Y | S. infirmus C. Jeffrey | N | S. prostratus Klatt | N |
S. auriculatissimus Britton | N | S. ingeliensis Hilliard | N | S. pseudolongifolius Sch.Bip ex J. Calvo | N |
S. austromontanus Hilliard | N | S. inornatus DC. | Y | S. pseudosubsessilis C. Jeffrey | N |
S. balensis S.Oritz and Vivero | N | S. intricatus S.Moore | N | S. ptarmicifolius Bory | N |
S. bampsianus Lisowski | N | S. isatideus DC. | Y | S. pterophorus DC. | Y |
S. barbatus DC. | N | S. isatidoides E. Phillips and C.A.Sm. | N | S. puberulus DC. | N |
S. baronii Humbert | N | S. jacksonii S. Moore | N | S. pubigerus L. | Y |
S. barorum Humbert | N | S. junceus (Less.) Harv. | N | S. purpureus L. | Y |
S. basalticus Hilliard | N | S. juniperinus L.f. | N | S. purtschelleri Engl. | N |
S. baurii Oliv. | N | S. junodii Hutch. and Burtt Davy | N | S. qathlambanus Hilliard | N |
S. belbeysius Delile | N | S. kacondensis S. Moore | N | S. quartziticola Humbert | N |
S. bellis Harv. | N | S. kalambatitrensis Humbert | N | S. quinquelobus (Thunb.) DC. | N |
S. bipinnatus Less. | N | S. kalingenwae Hilliard and B.L. Burtt | N | S. quinquenervius Sond. | N |
S. Bollei Sunding and C.Kunkel | Y | S. karaguensis O. Hoffm. | N | S. ragazzii Chiov. | N |
S. boutonii Baker | N | S. katangensis O. Hoffm. | N | S. randii S.Moore | N |
S. brachyantherus (Hiern) S.Moore | N | S. kayomborum Beentje | N | S. rehmannii Bolus | N |
S. brachypodus DC | Y | S. keniophytum R.E.Fr. | N | S. repandus Thunb. | N |
S. brevidentatus M.D. Hend | N | S. kerdousianus Gomiz and Llamas | N | S. reptans Turcz. | N |
S. brevilorus Hilliard | N | S. kuluensis S.Moore | N | S. resectus Bojer ex DC. | N |
S. brittenianus Hiern | N | S. kundelungensis Lisowski | N | S. retortus Benth. | N |
S. bryoniifolius Harv. | N | S. kuntzeanus Dinter | N | S. retrorsus DC. | Y |
S. bulbinefolius DC. | N | S. laevigatus Thunb. | N | S. rhammatophyllus Matt.f. | N |
S. bupleuroides DC. | Y | S. laevis Humbert | N | S. rhomboideus Harv. | Y |
S. burchellii DC. | Y | S. lamarckianus Bullock | N | S. rhyncholaenus DC. | N |
S. burtonii Hook.f. | Y | S. lanceus Aiton | N | S. rigidus L. | N |
S. byrnensis Hilliard | N | S. latecorymbosus Gilli | N | S. robertiifolius DC. | N |
S. cakilefolius DC. (Synonym of S. arenarius) | N | S. latibracteatus Humbert | N | S. roseiflorus R.E.Fr. | Y |
S. caloneotes Hilliard | N | S. laticipes Bruyns | N | S. rosmarinifolius L.f. | Y |
S. canabyi Humbert | N | S. latifolius DC. | Y | S. rugegensis Muschl. | N |
S. canaliculatus Bojer ex DC. | N | S. latissimifolius S. Moore | N | S. ruwenzoriensis S. Moore | Y |
S. canalipes DC. | N | S. lawalreeanus Lisowski | N | S. sabinjoensis Muschl. | N |
S. capuronii Humbert | N | S. laxus DC. | N | S. saboureaui Humbert | N |
S. cardaminifolius DC. | N | S. leandrii Humbert | N | S. sakalavorum Humbert | N |
S. carnosus Thunb. | N | S. lejolyanus Lisowski | N | S. sakamaliensis (Humbert) Humbert | N |
S. carroensis DC. | N | S. lelyi Hutch. | N | S. sandersonii Harv. | Y |
S. cathcartensis O. Hoffm. | Y | S. leptopterus Mesfin | N | S. saniensis Hilliard and B.L. Burtt | N |
S. caudatus DC. | N | S. lessingii Harv. | N | S. schimperi Sch.Bip. ex Hochst. | N |
S. cedrorum Raynal | N | S. letouzeyanus Lisowski | N | S. schultzii Hochst. ex A. Rich. | N |
S. chalureaui Humbert | N | S. leucadendron (G. Forst.) Hems.L. | N | S. schweinfurthii O.Hoffm. | Y |
S. chrysocoma Meerb. | Y | S. leucanthemifolius Poir. | Y | S. scitus Hutch. and Burtt Davy | N |
S. cinerascens Aiton | N | S. lewallei Lisowski | N | S. scoparius Harv. | N |
S. citriceps Hilliard and B.L.Burtt | N | S. lineatus DC. | N | S. semiamplexifolius De Wild. | N |
S. cochlearifolius Bojer ex DC. | N | S. linifolius L. | Y | S. seminiveus J.M. Wood and M.S. Evans | N |
S. coleophyllus Turcz. | N | S. Lisowskii Long Wang and Beentje | N | S. serratuloides DC. | Y |
S. comptonii J.C.Manning and Goldblatt | N | S. litorosus Fourc. | N | S. serrulatus DC. | N |
S. confertus Sch.Bip. Ex A.Rich. | N | S. littoreus Thunb. | N | S. serrurioides Turcz. | N |
S. conrathii N.E.Br. | Y | S. lividus L. | Y | S. shabensis Lisowski | N |
S. consanguineus DC. | Y | S. lobelioides DC. (Synonym of S. flavus) | N | S. simplicissimus Bojer ex DC. | N |
S. cordifolius L.f. | N | S. longiscapus Bojer ex DC. | Y | S. sisymbriifolius DC. | N |
S. cornu-cervi MacOwan | N | S. luembensis De Wild. and Muschl. | N | S. skirrhodon DC. | N |
S. coronatus (Thunb.) Harv. | Y | S. lycopodioides Schltr. | N | S. snowdenii Hutch. | N |
S. cotyledonis DC. | N | S. lydenburgensis Hutch. and Burtt Davy | Y | S. sociorum Bolus | N |
S. crassissimus Humbert | Y | S. lygodes Hiern | N | S. sophioides DC. | N |
S. crassiusculus DC. | N | S. lyratus Forssk. | Y | S. sororius C. Jeffrey | N |
S. crassorhizus De | N | S. mabberleyi C.Jeffrey | N | S. sotikensis S. Moore | N |
S. crenatus Thunb. | N | S. MacOwanii Hilliard | N | S. spartareus S. Moore | N |
S. crenulatus DC. | N | S. macrocephalus DC. | Y | S. speciosissimus J.C.Manning and Goldblatt | N |
S. crispatipilosus C.Jeffrey | N | S. macroglossoides Hilliard | N | S. speciosus Willd. | Y |
S. crispus Thunb. | Y | S. macroglossus DC. | N | S. spiraeifolius Thunb. | N |
S. cristimontanus Hilliard | N | S. macrospermus DC. | Y | S. squalidus L. | Y |
S. cryphiactis O.Hoffm. | N | S. madagascariensis Poir. | Y | S. stella-purpurea V.R.Clark, J.D.Vidal, and N.P.Barker | N |
S. cryptolanatus Killick | N | S. malacitanus Huter | Y | S. steudelii Sch.Bip. ex A. Rich. | N |
S. cyaneus O.Hoffm. | N | S. malaissei Lisowski | N | S. striatifolius DC. | N |
S. cymbalariifolius (L.) Less. | N | S. mandrarensis Humbert | N | S. strictifolius Hiern | N |
S. decaryi Humbert | N | S. maranguensis O.Hoffm. | N | S. subcanescens (DC.) Compton | N |
S. decurrens DC. | N | S. margaritae C.Jeffrey | N | S. subcoriaceus Schltr. | N |
S. deltoideus Less. | Y | S. marginalis Hilliard | N | S. subfractiflexus C. Jeffrey | N |
S. denisii Humbert | N | S. mariettae Muschl. | Y | S. submontanus Hilliard and B.L. Burtt | N |
S. dentatoalatus Mildbr. Ex C.Jeffrey | N | S. maritimus L.f. | Y | S. subrubriflorus O.Hoffm. | Y |
S. depauperatus Mattf. | N | S. marnieri Humbert | N | S. subsessilis Oliv. and Hiern | N |
S. diffusus L.f. | N | S. marojejyensis Humbert | N | S. subsinuatus DC. | N |
S. digitalifolius DC. | N | S. massaicus (Maire) Maire | Y | S. sylvaticus L. | Y |
S. dilungensis Lisowski | N | S. matricariifolius DC. | N | S. syringifolius O.Hoffm. | Y |
S. diodon DC. | N | S. mattirolii Chiov. | N | S. tabulicola Baker | N |
S. diphyllus De Wild. and Muschl. | N | S. mauricei Hilliard and B.L. Burtt | Y | S. tamoides DC. | Y |
S. discodregeanus Hilliard and B.L.Burtt | N | S. maydae Merxm. (Synonym of S. albopunctatus) | N | S. tanacetopsis Hilliard | N |
S. discokaraguensis C.Jeffrey | N | S. mbuluzensis Compton | N | S. teixeirae Torre | N |
S. dissidens Fourc. | N | S. melastomifolius Baker | N | S. telekii O.Hoffm. | N |
S. dissimulans Hilliard and B.L.Burtt | N | S. mesembryanthemoides Bojer ex DC. | N | S. telmateius Hilliard | N |
S. doryphoroides C.Jeffrey | N | S. mesogrammoides O.Hoffm. | N | S. tenellus DC. | N |
S. doryphorus Mattf. | N | S. meuselii Rauh | N | S. teneriffae Sch.Bip. ex Bolle | N |
S. dracunculoides DC. | N | S. meyeri-johannis EngL. | N | S. thamathuensis Hilliard | N |
S. dregeanus DC. | N | S. microalatus C. Jeffrey | N | S. thunbergii Harv. | N |
S. dumeticola S.Moore | N | S. microglossus DC. | Y | S. torticaulis Merxm. | N |
S. dumosus Fourc. | N | S. microspermus DC. | N | S. tortuosus DC. | N |
S. eenii (S.Moore) Merxm. | N | S. mimetes Hutch. and R.A. Dyer | N | S. trachylaenus Harv. | N |
S. elegans L. | N | S. mitophyllus C. Jeffrey | N | S. trachyphyllus Schltr. | N |
S. ellenbeckii O.Hoffm. | N | S. mlilwanensis Compton | N | S. transmarinus S. Moore | N |
S. eminens Compton | N | S. monticola DC. | N | S. triactinus S. Moore | N |
S. emirnensis DC. | N | S. mooreanus Hutch. and Burtt Davy | N | S. trilobus L. | N |
S. englerianus O.Hoffm. | N | S. moorei R.E.Fr. | N | S. triodontiphyllus C. Jeffrey | N |
S. eriobasis DC. (Synonym of S. erosus) | N | S. mooreioides C. Jeffrey | N | S. triplinervius DC. | N |
S. eriopus Willk. | N | S. morotonensis C. Jeffrey | N | S. triqueter Less. | N |
S. erlangeri O.Hoffm. | N | S. muCronatus Willd. | N | S. tsaratananensis Humbert | N |
S. erosus L.f. | N | S. multibracteatus Harv. | N | S. tugelensis J.M. Wood and M.S. Evans | N |
S. erubescens Aiton | Y | S. multicaulis DC. | N | S. tysonii MacOwan | N |
S. erysimoides DC. | N | S. multidenticulatus Humbert | N | S. ulopterus Thell. | N |
S. esterhuyseniae J.C.Manning and Goldblatt | N | S. muricatus Thunb. | N | S. umbellatus L. | Y |
S. euriopoides DC. | N | S. myriocephalus Sch.Bip. ex A.Rich. | N | S. umbricola Cron and B. Nord. | N |
S. evelynae Muschl. | N | S. nanus Sch.Bip. ex A. Rich. | N | S. umgeniensis Thell. | N |
S. exarachnoideus C.Jeffrey | N | S. napifolius MacOwan | N | S. unionis Sch.Bip. ex A. Rich. | N |
S. exuberans R.A.Dyer | N | S. natalicola Hilliard | N | S. urophyllus Conrath | N |
S. fanshawei Beentje | N | S. navicularis Humbert | N | S. urundensis S.Moore | N |
S. farinaceus Sch.Bip. Ex A.Rich. | N | S. navugabensis C. Jeffrey | N | S. vaingaindrani Scott Elliot | N |
S. flavus (Decne.) Sch.Bip. | Y | S. neo Bakeri Humbert | N | S. variabilis Sch.Bip. | N |
S. foeniculoides Harv. | N | S. neoviscidulus Soldano | N | S. venosus Harv. | N |
S. forbesii Oliv. and Hiern | N | S. ngandae Beentje | N | S. verbascifolius Burm.f. | N |
S. francoisii Humbert | N | S. ngoyanus Hilliard | N | S. vernalis Walds. and Kit. | Y |
S. fresenii Sch.Bip. | N | S. nyangani Beentje | N | S. vestitus P.J.Bergius | N |
S. gallicus Vill. Ex Chaix | Y | S. nyungwensis P. Maquet | N | S. vicinus S.Moore | N |
S. gariepiensis Cron | N | S. ochrocarpus Oliv. and Hiern | N | S. villifructus Hilliard | N |
S. garnieri Klatt | N | S. odontopterus DC. | N | S. vimineus DC. | N |
S. gazensis S.Moore | N | S. oederifolius DC. | N | S. vira-vira Hieron. | Y |
S. geniorum Humbert | N | S. ornatus S.Moore | N | S. vitellinoides Merxm. | N |
S. gerrardii Harv. | Y | S. othonniflorus DC. | N | S. vittarifolius Bojer ex DC. | N |
S. giessii Merxm. | N | S. oxyodontus DC. | Y | S. voigtii van Jaarzv. | N |
S. glaberrimus DC. | N | S. oxyriifolius DC. | Y | S. volcanicola C. Jeffrey | N |
S. glanduloso-lanosus Thell. | N | S. paarlensis DC. | N | S. vulgaris L. | Y |
S. glandulo-pilosus Volkens and Muschl. | N | S. pachyrhizus O. Hoffm. | N | S. waterbergensis S. Moore | N |
S. glastifolius L.f. | N | S. paludaffinis Hilliard | Y | S. windhoekensis Merxm. | N |
S. glaucus L. | Y | S. panduratus Less. (Synonym of S. erosus) | N | S. wittebergensis Compton | N |
S. glutinarius DC. | N | S. panduriformis Hilliard | N | S. xenostylus O. Hoffm. | N |
Species | Details |
---|---|
S. adnatus DC. | Toxic alkaloid (macrolide): Platyphylline [24]. |
S. aegyptius L. | Toxic alkaloids: Senecionine (pyrrolizidine) and otosenine (macrolide) [25]. |
S. aegyptius L. var. discoideus Boiss. | Sesquiterpenes: 1,10-epoxyfuranoeremophilane (in essential oil), with traces of monoterpenes [26]. Non-volatiles include 1-β-hydroxy-8-oxoeremophila-7,9-dien-12-oic acid, rutin, and quercetin-3-O-glucoside-7-O-rutinoside [27]. Novel eremophilane lactones also described [28]. |
S. affinis DC. | Sesquiterpenes: Cacalols and bisabolols [29]. |
S. angulatus L.f. | Toxic alkaloid: Angularine (pyrrolizidine) [30]. Phenols: Cynarin, chlorogenic acid and trans-ferulic acid [31]. Essential oils: α-Pinene, β-pinene, limonene, camphene, germacrene D, viridifloral, β-caryophyllene [32]. |
S. angustifolius (Thunb.) Willd. | Toxic alkaloids (pyrrolizidines): Senecionine N-oxide, retrorsine N-oxide, retrorsine, seneciphyline, senecionine, senkirkine [6]. |
S. asperulus DC. | Possible chemotypes. Terpenes: furoeremophilanes, α -humulene, ent-kaurenic acid, ent-kaurenol [33]. Toxic alkaloids: Pyrrolizidine alkaloid N-oxides (exact identity not known) [34]. |
S. bollei Sunding and C.Kunkel | Toxic alkaloid (pyrrolizidine): Senecivernine [35]. |
S. brachypodus DC. | Toxic alkaloid (pyrrolizidine): Rosmarinine [36]. |
S. bupleuroides DC. | Toxic alkaloid (pyrrolizidine): Retrorsine [37]. |
S. burchellii DC. | Toxic alkaloids (pyrrolizidine): Senecionine N-oxide and senkirkine [6]. |
S. burtonii Hook.F. | Sesquiterpene: Cacalolide derivative, 4α-[2′-hydroxymethylacryloxy]-1β-hydroxy-14-(5 → 6) abe oeremophilan-12,8-olide. Shikimic acid derivative, (3′E)-(1α)-3-hydroxymethyl-4β,5α-dimethoxycyclohex-2-enyloctadec-3′-enoate. Fatty acid derivatives, octacosan-1-ol, 3β-hydroxyolean-12-en-28-oic acid, and 3β-acetoxyolean-12-en-28-oic acid [38]. |
S. cathcartensis O.Hoffm. | Sesquiterpenes: Eremophilene derivatives [21]. |
S. chrysocoma Meerb. | Toxic alkaloids: 7-angelylplatynecine, 9-angelylplatynecine, sarracine, neosarracine [39], and other 7-Angelyl-1-methylenepyrrolizidines (pyrrolizidines) [40]. |
S. conrathii N.E.Br. | Sesquiterpenes: β-Farnesene, furoeremophilane derivatives, and germacrene D-4-ol [41]. Additionally, a nickel hyperaccumulator. |
S. consanguineous DC. | Toxic alkaloid: Retrorsine (pyrrolizidine), very low concentration [42]. |
S. coronatus (Thunb.) Harv. | Species did not contain toxic alkaloids [8], or mere traces, but further work necessary to know of the chemistry. |
S. crassissimus Humbert | Sesquiterpenes: Germacrene D, bicyclogermacrene, Z-caryophyllene epoxide and other epoxides. Triterpenes: Lupeol, its acetate, lupeone, β-amyrin acetate, β-amyrenone, glutin-5(6)-en-3β-ol, 28-oxo-β-amyrenone, and the angelate [43]. |
S. crispus Thunb. | Sesquiterpene dimers: Disesquiterpenoid derivative [44]. |
S. deltoideus Less. | Unusual sesquiterpenes, linear diterpenes, and polyunsaturated alkenes and -kynes [45]. Used as a medicine to treat gynaecological and obstetric disorders [46]. |
S. erubescens Aiton | Sesquiterpenes: Bisabolanes and eremophilanes [29]. |
S. flavus (Decne.) Sch.Bip. | Sesquiterpenes (Oxyeuryopsin derivatives): 3β-Methylbutyryloxyeuryopsin, 3β-angeloyloxyeuryopsin, 3β-senecioyloxyeuryopsin, 3β-hydroxyeuryopsin, euryopsin-3-one, furanoligularenone, and others [47]. |
S. gallicus Vill. Ex Chaix | Toxic alkaloids (pyrrolizidine): Ligularizine, senkirkine and senecionine N-oxide [48]. Essential oil: β-Phellandrene, apinene, germacrene-D, myrcene, α-copaene, sabinene, (Z)-β-ocimene, β-caryophyllene, p-cymene, β-pinene, α phellandrene, α-terpinolene, (E)-β-ocimene, α-humulene, azingiberene, and caryophyllene oxide [49]. |
S. gerrardii Harv. | Sesquiterpenes: Eremophilene derivatives [21]. |
S. glaucus L. | Essential oils: Isolongifolen-9-one, longiverbenone, 4-carene, p-cymene, thujone [50], m-mentha-1(7),8-diene, cis-m-mentha-2,8-diene, dehydrofukinone, α-terpinolene, 2,5-cyclohexadiene-1,4-dione,2-(1,1-dimethylethyl)-5-(2-methyl-2-propen-1-yl), sabinene, α-Fenchene and 1,3,8-p-menthatriene [51]. Phenols: Vanillic acid and gallic acid [52]. Flavonoids: Isorhamentin 3-O-β-D-glucoside, and isorhamentin 3-O-β-D-rutinoside. Benzofuran glucosides: 2,3-Dihydro-3β-hydroxyeuparin 3-O-glucopyranoside, isorhamentin 3-O-β-D-glucoside, and isorhamentin 3-O-β-D-rutinoside [53]. |
S. glaucus L. subsp. coronopifolius (syn. S. desfontainei). | Toxic alkaloids (pyrrolyzidine): Seneciphylline [25]. |
S. glutinosus Thunb. | Sesquiterpenes (seco-eremophilanes): Senglutinosin, 3α-hydroxy-10β-H-eremophil-11(13)-en-9-one, and nor-seco- glutinosone [33]. |
S. gossypinus Baker | Flavonoid: Kaempferol-3-O-α-L-arabinopyranoside. Triterpenes: α-Amyrin and β-amyrin [54]. |
S. grandiflorus P.J.Bergius | Sesquiterpenes (furano): Cacalol derivatives [55]. |
S. hadiensis Forssk. | Toxic alkaloids (macrolides): Rosmarinine, 12-O-acetylrosmarinine, neorosmarinine, hadiensine (1α-hydroxyplacyphylline), 12-O-acetylhadiewine, 12-O-acetylneohadiewine, and petitianine (2α-hydroxy-1,2-dihydroretronine) [56]. Sesquiterpenes (tricyclic): presilphiperfolan-2α,5α,8α-triol and presilphiperfolan-2α,5α,8α,10α-tetraol [57]. |
S. halimifolius L. | Sesquiterpenes (furano): Furanoeremophilanes [58]. |
S. heliopsis Hilliard and B.L.Burtt | Sesquiterpenes: Furanoeremophilanes and cacalols [29]. |
S. helminthioides (Sch.Bip.) Hilliard | Phenylpropenes: Trimethoxy-phenylpropenes [22]. |
S. hieracioides DC. | Sesquiterpenes (furo): 9,10-Dehydrofuranoeremophilane, ligularenolide, eremophil-7(11)-en-8,12-olide, 8,8′-epimeric dimers. Shikimic acid derivatives [59]. |
S. hoggariensis Batt. and Trab. | Phenols: 3,4-Dihydroxybenzoic acid, 4-hydroxybenzoic acid, 6,7-dihydroxycoumarin, vanillic acid, caffeic acid, p-coumaric acid, and ferulic acid [60]. |
S. hypochoerideus DC. | Sesquiterpenes (furano): Furanoeremophilanes [61]. |
S. ilicifolius Thunb. | Toxic alkaloid: Senecionine ‘responsible for bread-poisoning’ [62]. |
S. inaequidens DC | Toxic alkaloids (pyrrolizidine): Retrorsine, senecionine [42], senecivernine, integerrimine, and an analogue of retrorsine [63]. Possibly another chemotype with furanosesquiterpenes [58]. |
S. inornatus DC. | Toxic alkaloid (pyrrolizidine): O7-Angeloylretronecine [64]. Sesquiterpenes (furano): Furanoeremophilanes [58]. |
S. isatideus DC. | Vinyl-olefins: Polyunsaturated alkenes [65]. |
S. latifolius DC. | Toxic alkaloids: Retrorsine, isatidine, sceleratine, chlorodeoxysceleratine (merenskine), and the N-oxides of sceleratine and merenskine [66]. |
S. leucanthemifolius Poir. | Toxic alkaloids (pyrrolizidine): Integerrimine and senecionine [67]. Essential oils: α-hydroxy-p-cymene, carvacrol, nerol, carveol, and cis-α-bisabolene [68]. |
S. linifolius L. | Sesquiterpenes: furanoeremophilanes, i.e., maturinone and seven cacalohastin derivatives [69]. |
S. lividus L. | Sesquiterpenes: Eremophilanes [29]. Possibly essential oils: [70]. |
S. longiscapus Bojer ex DC. | Essential oils: Sabinene, elemicin, β-pinene, methyleugenol, α-pinene, and myrcene [71]. |
S. lydenburgensis Hutch. and Burtt Davy | Sesquiterpenes: Multiple cacalol derivatives [72]. |
S. lyratus Forssk. | Sterols: Sitosterol and stigmasterol. Triterpene: β-Amyrin [73]. |
S. macrocephalus DC. | Toxic alkaloids (pyrrolizidine): Traces of 7-senecioyl-9-sarracinylheliotridine and 7-angelyl-9-sarracinyl-heliotridine [74]. |
S. macrospermus DC. | Sesquiterpenes: Cacalohastin derivatives [75]. |
S. madagascariensis Poir. | Toxic alkaloids (pyrrolizidine): Senecivernine, senecionine, integerrimine, senkirkine, mucronatinine, retrorsine, usaramine, otosenine, acetylsenkirkine, desacetyldoronine, florosenine, and doronine [76]. |
S. malacitanus Huter | Toxic alkaloids (pyrrolizidine): Unnamed derivatives [77]. |
S. mariettae Muschl. | Toxic alkaloid (pyrrolizidine): Retrorsine [78]. |
S. maritimus L.f. | Alkanes: Polyunsaturated aklenes and -ynes. Furanosesquiterpene derivatives [79]. |
S. massaicus (Maire) Maire | Essential oil: p-Cymene, n-hexadecanoic acid, and docosane-11-decyl [80]. |
S. mauricei Hilliard and B.L.Burtt | Sesquiterpenes: Senmauricinol-(2-methyacrylat), hilliardinolisobutyrat, hilliardinol-(2-methylacrylat), 10β-hydroxy-1-oxo-6β-isobutyryloxy-2,3-dehydro-furanoeremophil-9-on, 2,3-desoxyhilliardinol-isobutyrat, 2,3-desoxohilliardinol-(2-methylacrylat), and 8,12-dioxo-7,11,9,10-tetradehydroeremophilan [81]. |
S. microglossus DC. | Sterols: Stigmasterol, sitosterol, dammaradienol, its 3-epimer, and the angelate. Sesquiterpenes: Germacrene D, y- and δ-cadinene, bisabolol, the angelate [41]. |
S. oxyodontus DC. | Sesquiterpene: Pentaynene sesquiterpene, bisabolene derivatives [82], and triquinane sesquiterpenes [83] p-Hydroxyacetophenone [82]. |
S. oxyriifolius DC. | Sesquiterpenes: Tricyclic bisabolol derivatives (epoxides) [84]. |
S. paludaffinis Hilliard | Sesquiterpenes: Cacalol and bisabolol derivatives [85]. |
S. paniculatus P.J.Bergius | Toxic alkaloids (pyrrolizidine): 7β-Angelyl-1-methylene-8α-pyrrolizidine, 7β-angelyl-1-methylene-8α-pyrrolizidine, 7β-angelyl-1-methylene8α-pyrrolizidine-4-oxide, 7-angelylhastanecine, 9-angelylhastanecine, 7-angelylplatynecine, 9-angelylplatynecine, 9-angelylplatynecine-4-oxide, sarracine, neosarracine, and retrorsine [86]. |
S. paucicalyculatus Klatt | Toxic alkaloids (pyrrolizidine): Retrorsine and isatidine [87]. |
S. polyanthemoides Sch.Bip. | Sesquiterpenes (furano): Cacalol derivatives [55]. Essential oils: Limonene, p-cymene, β-selinene, α-pinene, β-pinene, 1,8-cineole, caryophyllene oxide, and humulene epoxide II [88]. |
S. pterophorus DC. | Toxic alkaloids (pyrrolizidine): Retronecine, otonecine, platynecine, and rosmarinecine derivatives [89]. |
S. pubigerus L. | Sesquiterpenes: Germacrene D, bicyclogermacrene, beta-farnesene, and bisabolol derivatives. Toxic alkaloid (pyrrolizidine): acylpyrrole [90]. |
S. purpureus L. | Sesquiterpenes (eremophilenes): Diesters of seneremophilondiol, senescaposone and isosenescaposone, esterified with 4-methyl-5-acetoxy-pent-2-enoic acid [21]. |
S. retrorsus DC. | Toxic alkaloids (pyrrolizidine): Retrorsine, isatidine, and isatinecic acid [91]. |
S. rhomboideus Harv. | Sesquiterpenes: Eremophilene derivatives [21]. |
S. roseiflorus R.E.Fr. | Flavonoids: O-methylated, i.e., 5,4′-dihydroxy-7-dimethoxyflavanone [92]. |
S. rosmarinifolius L.f. | Toxic alkaloid (macrolide): Rosmarinine [62]. |
S. ruwenzoriensis S.Moore | Toxic alkaloids (pyrrolizidine): Isoline and bisline [93]. |
S. sandersonii Harv. | Sesquiterpenes: Diester and germacrene derivatives [94]. |
S. schweinfurthii O.Hoffm. | Toxic alkaloid (pyrrolizidine): 7β-Hydroxy-1-methylene-8α-pyrrolizidine N-oxide [95]. |
S. serratuloides DC. | Sterols: Phytosteroids and estran-3-one, 17-(acetyloxy)-2-methyl-, (2à,5à,17á) [96]. Used as a medicine to treat gynaecological and obstetric disorders [46]. |
S. speciosus Willd. | Toxic alkaloids (pyrrolizidine): 7-Senecioyl-9-sarracinylheliotridine and 7-angelyl-9-sarracinyl-heliotridine [74]. |
S. squalidus L. | Essential oils: p-Cymene and α-phellandrene [97]. |
S. subrubriflorus O.Hoffm. | Diterpenes: Sandaracopimarene derivatives. Sesquiterpene: Bisabolene derivative (4,7-oxide) [98]. |
S. sylvaticus L. | Sesquiterpenes: Alkenes, bicyclic derivatives, and furanosesquiterpenes [79]. |
S. syringifolius O.Hoffm. | Toxic alkaloids (pyrrolizidine): Angularine, rosmarinine, and 12-O-acetylrosmarine, together with their N-oxides [99]. |
S. tamoides DC. | Flavonoids: di-C-rhamnosylapigenin, mangiferin, and isomangiferin [100]. |
S. umbellatus L. | Sesquiterpenes: Furanoeremophilane derivatives [101]. |
S. vernalis Walds. and Kit. | Sesquiterpenes (furano): Cacalol derivatives [55]. |
S. vira-vira Hieron. | Toxic alkaloids (pyrrolizidine): Anacrotine, neoplatyphylline, uspallatine. Flavonoids: Quercitrin, rutin, isorhamnetin 3-O-β-robinobioside. Sterols: Sitosterol, campesterol, stimasterol, stimasta-3,5-dien-7-one, and stimasta-4,6-dien-3-one. Triterpenes: α-/β-amyrins [102]. |
S. vulgaris L. | Toxic alkaloids (pyrrolizidine): Senecionine, senecionine N-oxide, integerrimine N-oxide, seneciphylline N-oxide, retrorsine N-oxide, and spartioidine N-oxide [103]. Essential oils: α-Humulene, (E)-β-caryophyllene, terpinolene, ar-curcumene, and geranyl linalool [104]. |
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Sadgrove, N.J. Comment on Pyrrolizidine Alkaloids and Terpenes from Senecio (Asteraceae): Chemistry and Research Gaps in Africa. Molecules 2022, 27, 8868. https://doi.org/10.3390/molecules27248868
Sadgrove NJ. Comment on Pyrrolizidine Alkaloids and Terpenes from Senecio (Asteraceae): Chemistry and Research Gaps in Africa. Molecules. 2022; 27(24):8868. https://doi.org/10.3390/molecules27248868
Chicago/Turabian StyleSadgrove, Nicholas John. 2022. "Comment on Pyrrolizidine Alkaloids and Terpenes from Senecio (Asteraceae): Chemistry and Research Gaps in Africa" Molecules 27, no. 24: 8868. https://doi.org/10.3390/molecules27248868
APA StyleSadgrove, N. J. (2022). Comment on Pyrrolizidine Alkaloids and Terpenes from Senecio (Asteraceae): Chemistry and Research Gaps in Africa. Molecules, 27(24), 8868. https://doi.org/10.3390/molecules27248868