Quinic and isochlorogenic acids were identified in sunflower’s seeds (Mourgue et al. 1975). Caffeic acid, the most predominant phenolic acid, along with p-hydroxybenzoic, p-coumaric, cinnamic, m-hydroxybenzoic, vanillic and syringic acids, was identified in both acid and base hydrolysates of sunflower seeds with only slight variations in concentrations among the cultivars (Leung et al. 1981). Relatively larger amounts of these acids were detected in the basic hydrolysates except in the cases of p-hydroxybenzoic, vanillic and syringic acids, indicating that these acids may exist in glycosidic form to a larger extent than in ester form in the cultivars examined. The principal phenolic constituents of sunflower seeds were chlorogenic acid (CGA), smaller quantities of caffeic acid, cinnamic, coumaric, ferulic, sinapic and hydroxy-cinnamic and traces of vanillic, syringic and hydroxybenzoic acids were also present (Pedrosa et al. 2000). Total tocopherol in H. annuus seeds (32 accessions) was determined as 389.8 mg/kg seed comprising mainly 97.9 mg α-tocopherol, 1.8 mg β-tocopherol and 0.3 mg γ-tocopherol (Velasco et al. 2004).

Six different phenolic compounds were extracted from sunflower seeds and kernels (Žilić et al. 2010). Chlorogenic acid was the most abundant phenol. The chlorogenic acid content strongly correlated with total phenols (R ² = 0.93). Other marked phenolics were caffeic acid, ferulic acid, rosmarinic acid, myricetin and rutin. The total tocopherols were significantly higher in kernels than in seeds of all sunflower hybrids. Concentrations in sunflower seeds ranged from 200.67 to 220.05 μg/g and from 256.62 to 267.49 μg/g in sunflower kernels where α-tocopherol was the dominant isomer in all samples. The α-tocopherol content was 98 % of averaged of the total tocopherols in all analyzed samples. β + γ-tocopherols were present in sunflower samples in amounts of 1.28–1.61 % of the total tocopherols. The level of δ-tocopherol was not significant in all sunflower samples and ranged from 0.42 to 0.52 % of the total tocopherols.

Seed reserve storage proteins of sunflowers were found to be globulins and albumins stored in protein bodies (Baudet and Mossé 1977; Buttrose and Lott 1978; Durante et al. 1989). The native globulin protein showed an apparent molecular weight of 300 K, but a 190 K band was present in some selfed sunflower lines (Durante et al. 1989). The globulin fraction amounted to 70–80 % of the total protein, light albumins constituted 20 % and 5–10 % for heavy albumins (Baudet and Mossé 1977). ‘Light’ albumins appeared as a rather homogeneous constituent with a low molecular weight of 11,000–1,600 (Raab and Schwenke 1975; Baudet and Mossé 1977) and an amino acid composition showing high amounts of methionine, cystine, arginine and glutamine (Baudet and Mossé 1977). ‘Heavy’ albumins possessed a molecular weight of 48,000 and a very different amino acid composition with a high level of lysine (Baudet and Mossé 1977). The major seed globulin called helianthinin was found to be an 11S protein with an oligomeric structure and 300 K MW (Schwenke et al. 1974, 1975) and to consist of 6 subunits (Plietz et al. 1978). Helianthinin was found to contain high contents of glutamic (26 %) and aspartic (14 %) acid and arginine (9.7 %) as well as a low content of sulphur-containing amino acids (Schwenke et al. 1979). 59 % of the acidic amino acids were present in an amidated form. The globulin contained 12 disulphide bridges per molecule. Low molecular weight (10,000–18,000) methionine-rich albumin was also found in sunflower seeds (Kortt and Caldwell 1990). The major albumins (4–8) contain high contents of glutamine/glutamic acid, asparagine/aspartic acid, arginine and cysteine, characteristic of the 2S class of seed storage proteins. One exception was the small glutamine/glutamic acid content of albumin 6. Two of the sunflower albumins (7 and 8) with Mr 10,000 were methionine-rich proteins containing 16 residues percent methionine as well as 8 residues percent cysteine. The methionine-rich 2S sunflower seed protein was found to consist of a single polypeptide chain of 103 amino acids (molecular mass 12,133 Da) which contained 16 residues of methionine and 8 residues of cysteine (Kortt et al. 1991). The sunflower protein exhibited 34 % identity with the methionine-rich Brazil nut 2S protein. Helianthinin was found to be the most abundant storage protein of sunflower seeds; two populations of the monomeric form of helianthinin with denaturation temperatures of 65 and 90 °C were found (González-Pérez et al. 2004). The structural and interfacial properties of five different fractions of sunflower seed storage proteins, namely, lipid transfer protein (LTP), the methionine-rich 2S albumin SFA8 (sunflower albumin 8) and three mixtures of non-methionine-rich 2S albumins called Alb1 and Alb2 proteins (sunflower albumins 1 and 2), were characterized (Berecz et al. 2010). Heating affected all of the protein fractions, with SFA8 and LTP becoming more surface active than the native proteins after heating and cooling. LTP appeared to be less thermostable. SFA8 generated the greatest elastic modulus and formed the most stable emulsions, whereas LTP showed poorer emulsification properties. The mixed 2S albumin fractions showed moderate levels of surface activity but had the poorest emulsification properties among the proteins studied.

Peroxisome membrane proteins (PMPs) were found in sunflower seed cotyledons (Jiang et al. 1994). Six prominent nondenatured PMP complexes and ten prominent sodium dodecyl sulfate (SDS)-denatured polypeptides were identified in the membranes of the three types of peroxisomes: glyoxysomes, transition peroxisomes and leaf-type peroxisomes in the cotyledons.

The four most abundant anthocyanins in the hulls of purple sunflower seeds were identified as cyanidin 3-glucoside, cyanidin 3-malonylglucoside, cyanidin 3-xyloside and cyanidin 3-malonylxyloside (Mazza and Gao 1993). From the exudate of germinating sunflower seeds was isolated a stereoisomer of diversifolide, 4,15-dinor-3-hydroxy-1(5)-xanthene-12,8-olide (designated sundiversifolide) with allelopathic activity (Ohno et al. 2001).

Analyses carried out in the United States reported that dried sunflower seed kernels have the following proximate composition (per 100 g edible portion): water 4.73 g, energy 584 kcal (2,445 kj), protein 20.78 g, total lipid 51.46 g, ash 3.02 g, carbohydrates 20.00 g, total dietary fibre 8.6 g, total sugars 2.62 g, Ca 78 mg, Fe 5.25 mg, Mg 325 mg, P 660 mg, K 645 mg, Na 9 mg, Zn 3.14 mg, Cu 0.824 mg, Mn 1.626 mg, Se 8.2 μg, vitamin C 1.4 mg, thiamine 0.555 mg, riboflavin 0.333 mg, niacin 2.832 mg, pantothenic acid 0.976 mg, vitamin B-6 0.366 mg, total folate 423 μg, choline 95.8 mg, vitamin A 53 IU, vitamin E (α-tocopherol) 0.05 mg, vitamin K (phylloquinone) 9 μg, β-carotene 32 μg, total saturated fatty acids 0.254 g, total monounsaturated fatty acids 0.303 g, total polyunsaturated fatty acids 0.627 g, phytosterols 124 mg, tryptophan 0.247 g, threonine 0.928 g, isoleucine 1.053 g, leucine 1.964 g, lysine 1.671 g, methionine 0.213 g, cystine 0.334 g, phenylalanine 1.103 g, tyrosine 0.827 g, valine 1.161 g, arginine 2.411 g, histidine 0.664 g, alanine 1.070 g, aspartic acid 2.916 g, glutamic acid 4.437 g, glycine 1.095 g, proline 1.099 g and serine 1.195 g (USDA 2012).

Sunflower oil is the non-volatile oil expressed from the seeds. British Pharmacopoeia Commission (2005) listed the following profile: palmitic acid (4–9 %), stearic acid (1–7 %), oleic acid (14–40 %) and linoleic acid (48–74 %). Sunflower oil also contains lecithin, tocopherols, carotenoids and waxes and has a high vitamin E content. It is a combination of monounsaturated and polyunsaturated fats with low saturated fat levels.

The seed lipids from five sunflower mutants, two with high-palmitic acid contents, one of them in high-oleic background and three with high-stearic acid contents, were found to have increased saturated fatty acid content with high levels of triacylglycerols (Alvarez-Ortega et al. 1997). No difference between mutants and standard sunflower lines (controls) was found in minor fatty acids: linolenic, arachidic and behenic. In the high-palmitic mutants, palmitoleic acid (16:1n−7) and some palmitolinoleic acid (16:2n−7, 16:2n−4) were present. Phosphatidylinositol, the lipid with the highest palmitic acid content in controls, also had the highest content of palmitic or stearic acids, depending on the mutant type. The triacylglycerol (TAG) composition of oils from new high-saturated sunflower lines was found to be characterized by triacylglycerol species with asclepic (cis,delta11-octadecenoic acid, isomer of oleic acid), araquidic or behenic acids (Fernández-Moya et al. 2000). The TAG molecular species that contained asclepic acid instead of oleic acid were found to have a longer retention time.

High-palmitoleic-acid sunflower mutant was found to have contents of unusual acyl chains up to 20 % (12 % of 16:1delta9, 5 % of 16:2delta9,12 and 6 % of 18:1delta11), whereas these fatty acids were found in negligible amounts in common sunflower cultivars (Salas et al. 2004). The high-palmitoleic-acid phenotype was associated with a concerted reduction in the fatty acid synthase II activity with respect to the control lines and an increase of stearoyl-ACP desaturase activity with respect to the high-palmitate mutant line. The high-palmitic, low-palmitoleic sunflower mutant lines CAS-18 and CAS-25 (with a high-oleic background) had been selected from the high-stearic mutant CAS-3 (Serrano-Vega et al. 2005). In these high-palmitic lines, desaturation of palmitic acid and the synthesis of palmitoleic acid and its derivatives (asclepic and palmitolinoleic acids) were reduced, and stearic content increased. Introducing a FA thioesterase from a high-palmitic line (e.g., CAS-5) into the high-stearic CAS-3 increased the stearic acid content from 27 to 32 % in the new high-stearic line CAS-31. Seed oils from new recombinant high-stearic sunflower lines CAS-29 and CAS-30 were found to contain up to 34.5 % of stearic acid, whereas CAS-15 and CAS-33 with a high-oleic-acid background contained only 24.9 and 17.4 % of stearic acid, respectively (Fernández-Moya et al. 2005).

As seen from above, there are various types of sunflower oils produced which differs in the levels and composition of fatty acid profiles. The USDA (2012) has analyzed the nutrient composition (per 100 g values) of various types of vegetable sunflower oils in the United States:

As a frying oil, sunflower oil behaves as a typical vegetable triglyceride. In cosmetics, it has smoothing properties and is considered noncomedogenic. Only the high-oleic variety possesses shelf life suitable for commercial cosmetic formulation.

Total carotenoids in H. annuus cv. Sunrich orange flower was 1023.8 ug/g FW, in cv. Sonia (orange flowers) 1599.6 ug/g FW, in cv. Sunrich lemon (yellow flowers) 305.2 ug/g FW, and in cv. Valentine (yellow flowers) 143.8 ug/g FW (Kishimoto et al. 2007).

Sixty-nine compounds were identified in the essential oils of leaves and flowers of sunflower plants. Significant percentage variations were recorded between the leaves and flowers oil content. The monoterpenes were the major compounds present in both essential oils examined. α-Pinene content was higher in flowers (72.6 %) than in leaves (28.6 %). The content of sabinene was about two times higher in leaves than in flowers.

Lipids in sunflower pollens rich in omega-3 linolenic acid including triglycerides, free fatty acids, phosphatidylethanolamines, phosphatidic acids and phosphatidylcholines were highly phagostimulatory (Lin and Mullin 1999). Other important phagostimulatory components included a hydroxycinnamic acid-polyamine amide, N(1),N(5),N(10)-tri[(E)-p-coumaroyl]spermidine and a flavonol, quercetin β-3-O-glucoside. The major component of sunflower pollen lipids was the seco-triterpene helianyl octanoate, followed by new β-diketones as second major group of compounds that included -phenyl-β-diketones (Schulz et al. 2000). Further lipid classes present were related hydroxyketones and diols and also present were β-dioxoalkanoic acids which most likely were biogenetic precursors of the diketones. Also, the composition of the pollen coat resembled the total extract, but lacked dioxoalkanoic acids and certain estolides. Sunflower pollen coat was found to be richer in lipids (8 %) than stigma (2.2 %) on fresh weight basis (Shakya and Bhatla 2010). Neutral lipids were preferentially found localized in the pollen coat. Neutral esters and triacylglycerols (TAGs) were the major lipidic constituents in pollen grains and stigma, respectively. Lignoceric acid (24:0) and cis-11-eicosenoic acid (20:1) were specifically expressed only in the pollen coat. Lipase activity was expressed both in pollen grains and stigma, while stigma exhibited a better expression of acyl-ester hydrolase activity than that of observed in both the pollen fractions. Expressions of two acyl-ester hydrolases (41 and 38 kDa) were found to be specific to pollen coat.

The saponified sunflower ligule extract afforded two esters of ent-kaur-16en-19-oic and ent-trachyloban-19-oic acids with thujanol (Pyrek 1984). The following diterpenoids were also identified: ent-kaur-16-en-19-al; ent-trachyloban-19-al; ent-kauran-16β-ol; ent-kauran-16α-ol; ent-kauran-16β, 19-diol; ent-atisan-16α-ol; and ent-atisan-16β-ol. Loliolide acetate was also isolated from an acetylated portion of the same extract. Three bisdesmosidic triterpenoid saponins, helianthoside 1 (1), 2 (2) and 3 (3), and monodesmoside 4 were isolated from sunflower flowers (Bader et al. 1991). Germacranolides 3-O-methylniveusin A and 1,10-O-dimethyl-3-dehydroargophyllin B diol, the eudesmanoic acid eudesma-1,3,11(13)-trien-12-oic acid and the diterpene 7-oxo-trachyloban-15α, 19-diol and 5-hydroxy-4,6,4′-trimethoxyaurone were isolated from the flower epicuticle of sunflower (Alfatafta and Mullin 1992). Two antifungal benzopyran derivatives, 6-acetyl-2,2-dimethyl-1,2-benzopyran (1) and 6-acetyl-7-hydroxy-2,2-dimethyl-1,2-benzopyran (2), were isolated from the ethanol extract of sunflower receptacles (Satoh et al. 1996).

Floral chemicals with insect feeding-deterrent activity included the following: sesquiterpene lactones (e.g., argophyllin A, 3-O-methylniveusin A and germacranolide angelates), diterpenes (grandifloric acid and its 15-angelate) and phenolics, flavonoids (nevadensin and quercetin β-7-O-glucoside) and dicaffeoylquinic acids (Mullin et al. 1991) and sesquiterpenes, germacranolides 3-O-methylniveusin A and 1,10-O-dimethyl-3-dehydroargophyllin B diol, the eudesmanoic acid eudesma-1,3,11(13)-trien-12-oic acid, the diterpene 7-oxo-trachyloban-15α, 19-diol and hydroxy-4,6,4′-trimethoxyaurone (Alfatafta and Mullins 1992).

Eleven diterpene compounds were obtained from the flower disc of H. annuus and identified as ent-kaurane-2α, 16α-diol (1) and ent-kaurane-15α,16α-epoxy-17-al-19-oic acid (2) and nine known diterpenes, ent-kaurane-16P-ol (3), phyllocladan-16β-ol (4), ent-atisan-16α-ol (5), grandifloric acid (6), angeloylgrandifloric acid (7), ent-kaurane-16-en-19-oic acid (8), ent-kaurane-17-hydroxy-15-en-19-oic acid (9), ent-kaurane-16β, 17-dihydroxy-19-oic acid (10) and ciliaric acid (11) (Suo et al. 2007). Two new oleanane-type triterpene glycosides, named helianthosides 4 (4) and 5 (5), along with four known triterpene glycosides, helianthosides 1 (1), 2 (2), 3 (3) and B (6), were isolated from an n-butanol-soluble fraction of a methanol extract of sunflower (Helianthus annuus) petals (Ukiya et al. 2007).

Eight fatty acid esters of triterpene alcohols (1–8), four free triterpene alcohols (9, 12, 17 and 18), four diterpene acids (19–22), two tocopherol-related compounds (23 and 24), four estolides (25–28), three syn-alkane-4,6-diols (29–31), one 1,3-dioxoalkanoic acid (32) and one aliphatic ketone (33), along with the mixture of free fatty acids, were isolated from the diethyl ether extract of the pollen grains of sunflower (Ukiya et al. 2003b). Sunpollenol and five other rearranged 3,4-seco-tirucallane-type triterpenoids (1–6) were isolated from the diethyl ether extract of the pollen grains of sunflower (Ukiya et al. 2003a). Two new diterpenes, 2β, 16β-ent-kaurane diol and 15α, 16α-epoxy-17β-al-ent-kaurane-19-oic acid, were isolated from Helianthus annuus (Suo et al. 2006).

Barker (1997) and Foster et al. (2003) found that nonpolar (pentane) and moderately polar (dichloromethane) extracts of sunflower bracts contained compounds that stimulated oviposition by females banded sunflower moth (BSFM) Cochylis hospes. Two diterpenoid alcohols ent-kauran-16α-ol and ent-atisan-16α-ol were isolated from a dichloromethane extract of pre-bloom sunflowers heads and found to stimulate female BSFM. Two diterpenoid alcohols, ent-kauran-16α-ol (1) and ent-atisan-16α-ol (2), along with ent-trachyloban-19-oic acid (3) and ent-kaur-16-en-19-oic acid (4), were isolated from pre-bloom sunflower heads as oviposition stimulants for the female BSFM (Morris et al. 2005). Compounds 3 and 4 failed to stimulate significant egg laying at any of the dosages tested. Three diterpenoids, grandifloric acid (1), 15β-hydroxy-ent-trachyloban-19-oic acid (2) and 17-hydroxy-16α-ent-kauran-19-oic acid (3), were isolated from polar fractions of pre-bloom sunflower head extract and found to stimulate oviposition by female BSFM (Morris et al. 2009).

Sesquiterpenes and sesquiterpene lactones such as germacrolides and heliangolides were found as major natural compounds in linear and capitate glandular trichomes of sunflower, Helianthus annuus (Göpfert et al. 2005, 2009, 2010). The key enzymes of sesquiterpene lactone biosynthesis in the glandular trichomes of sunflower anthers were identified as two germacrene A synthases HaGAS1 and HaGAS2 (Göpfert et al. 2009) which also occurred in the roots. In addition using reverse transcription-PCR experiments, a third germacrene A synthase, HaGAS3, was identified (Göpfert et al. 2010). The new enzyme occurred in plant tissues not linked to the presence of specific trichomes (e.g., cotyledons) and was absent in roots. The experiments showed that independently regulated pathways for the first cyclic sesquiterpene, germacrene A, were present in sunflower.

Sixty-nine compounds were identified in the essential oils of leaves and flowers of sunflower cultivars Carlos and Florom 350 plants grown in Tuscany, Italy (Ceccarini et al. 2004). The monoterpenes were the major compounds present in both essential oils examined. α-Pinene content was higher in flowers (72.6 %) than in leaves (28.6 %). The content of sabinene was about 2 times higher in leaves than in flowers. There were no significant differences between the essential oil compositions of the oils obtained from the same organs of the two cultivars. Pinene, cis-verbenol and β-gurjunene were in both the main volatiles but with significant quantitative differences; moreover, Florom oil was characterized by a greater variety of constituents (Cioni et al. 2005). The fixed oil and the waxes composition showed a general qualitative homogeneity, for both cultivars, even though marked quantitative differences were observable.

Sunflower flower was found to contain ubiquitin, a 76-amino acid protein, the most conserved polypeptide (Binet et al. 1989). Accumulation of polyubiquitin genes (UbB1 and UbB2) were found to be mainly induced by heat stress or during flower development (Binet et al. 1991a, b). Accumulation levels of the 0.7- and 1.6-kb mRNAs (monoubiquitin and hexaubiquitin, respectively) actually decreased during late embryogenesis. In contrast, tetraubiquitin (1.3 kb) mRNAs were approximately eight- to tenfold more abundant in mature seeds than in young embryos (Almoguera et al. 1995).

Sunflower leaf tissues contained allagochrome and chlorogenic acid (Habermann 1967). Sesquiterpene lactones niveusin C (I) and 15-hydroxy-3-dehydrodesoxyfruticin (II) were found in the young leaves (Spring and Hager 1982; Spring et al. 1982b, 1986). In leaves grown in high-intensity light (100 W/m⁻²), the concentration of sesquiterpene lactone (SQL) I increased sixfold and of SQL II 19-fold compared to leaves in low-intensity light (5 W/m⁻²) (Spring et al. 1986). Sesquiterpene lactones niveusin C, argophyllin B, 15-hydroxy-3-dehydrodesoxyfruticin and three germacranolides of the niveusin A-type were identified in the resinous content of multicellular capitate glandular trichomes of sunflower leaves (Spring et al. 1987, 1989). Seven sesquiterpene lactones 4,5-dihydroniveusin A, argophyllin B, argophyllin A, 15-hydroxy-3-dehydrodesoxyfruticin, niveusin B, 1,2-anhydridoniveusin A and an unidentified epoxide were isolated from sunflower leaves (Chou and Mullin 1993).

The medium polar fractions from sunflower leaf aqueous extracts afforded five guaianolides, the annuolides A–E (Macías et al. 1993b). From the medium polar active fractions, a sesquiterpene heliannoul A was isolated (Macías et al. 1993b). From the moderately polar fractions of sunflower leaf aqueous extract, 3 sesquiterpenes heliannuols B–D were isolated (Macías et al. 1994).

From an aqueous sunflower leaf extract, six new heliannuols were isolated: three 7,10-heliannanes, heliannuols F (1), I (4) and J (5), and three 7,11-heliannanes, heliannuols G (2), H (3) and K (6) (Macías et al. 1999c). Allelopathic sesquiterpene lactones found in the leaves included the following: 1,2-anhydrido-4,5-dihydroniveusin A, annuithrin, annuolides A,C,F,G, 8β-angeloyloxycumambranolide, helivypolides A–B, melampolides, heliangolides, cis,cis-germacranolides and trans,trans germacranolides (Macías et al. 1996a). Eleven allelopathic compounds (trivial and systematic names) were isolated from the leaves: heliannuol A (7R,11-heliannane-5,10S-diol), heliannuol B (7R,10R-heliann-8(9)-ene-5,11-diol), heliannuol C (8S*,11-heliann-7(14)-ene-5,10R*-diol), heliannuol D (7R,10R-helianane-5,11-diol), heliannuol E (8R,10R-heliann-7(14)-ene-5,11-diol), heliannuol F (5,11-dihydroxy-7S,10R-heliannan-8-one), heliannuol G (7S,11-heliann-9(10)-ene-5,8R-diol), heliannuol H (7S,11-heliann-9(10)-ene-5,8S-diol), heliannuol I (7R,8S-epoxy-7,10R-heliannane-5,11-diol), heliannuol J (7S,8R-epoxy-7,10R-heliannane-5,11-diol) and heliannuol K (5-hydroxy-7R,11-heliannan-10-one) (Macías et al. 2000). Five allelochemicals, chlorogenic, caffeic, syringic, vanillic and ferulic acids, were identified in the leaves (Ghafar et al. 2001). It has been found that total phenols in the leaves were more (0.0316 mM/g) as compared to the stem (0.016 mM/g).

Sesquiterpene lactones annuolide E and leptocarpin, and the sesquiterpenes heliannuols A, C, D, F, G, H, I and L, helibisabonol A and helibisabonol B and bisnorsesquiterpene, annuionone E, were isolated from CH₂Cl₂ leaf extract (Macías et al. 2002b). (±)-Helibisabonol A, a new sesquiterpene with phytotoxic activity, was isolated from sunflower leaves (Macías et al. 2002a). The polar bioactive fractions of the aqueous sunflower leaf extract yielded 10 lignans and a phenylpropanoid: pinoresinol (1), siringaresinol (2), medioresinol (3), buddlenol E (4), lariciresinol (5), 7-hydroxylariciresinol (6), neo-olivil (8), dihydro-dehydrodiconiferilic alcohol (9), l-(4′-hydroxy-3′-methoxyphenyl)-2-[4″-(3hydroxypropyl)-2″-methoxyphenoxy]-propane-l,3-diol (10) and 3-(4-hydroxy-3,5-dimethoxyphenyl) propan-l-ol (11) (Macías et al. 2004b). Compound 7 tanegool was isolated as a natural aglycone. The polar bioactive fractions of Helianthus annuus cv. Stella and SH-222 yielded eight apocarotenoids, annuionones A to H (Macías et al. 2004a). From the medium polar active fraction of leaf aqueous extract, allelopathic spiroterpenes heliespirones C–E were isolated (Macías and Galindo 2005).

Annuionone H was isolated from sunflower aqueous leaf extract (Anjum and Bajwa 2005). Six sesquiterpene lactones (annuolide H, helivypolides F, H, I and J, and helieudesmanolide A), 1,2-anhydroniveusin A, 1-methoxy-4,5-dihydroniveusin and 15-hydroxy-3-dehydrodeoxyfruticin were isolated from sunflower leaves (Macías et al. 2006a). From the medium, polar bioactive fractions of sunflower leaf aqueous extract heliespiranes with a novel spiro heterocyclic sesquiterpene skeleton, namely, heliespirones B and C, were isolated (Macías et al. 2006b).

Sunflower stems yielded small quantity of trachyloban-19-oic and (−)-kaur-16-en-19-oic acids trachyloban-19-oic and (−)-kaur-16-en-19-oic acids with antimicrobial property (Mitscher et al. 1983). The following main volatile components were found in the headspace profile of sunflower stems: α-pinene (86.2 %), β-pinene (4.1 %), butyl acetate (2.3 %) camphene (1.9 %) (Buchbauer et al. 1993). Other important components (<1 %) included the following: acetic acid, α-thujune, limonene, β-phellandrene, (E)-2-hexen-1-ol, 3-heptanol, decanal, octanol, benzaldehyde, noanol, 2-nonanol, linalool, bornyl acetate, geranyl acetate, β-caryophyllene and vanillin. Minor headspace constituents of sunflower stems included anisole, butanol, ethyl acetate, fenchone, hexanal, Z-3-hexenol, hexyl acetate, pentanol, propyl acetate, α-terpineol, β-thujone and 2-undecanol. Three alleochemicals were found in the stem (chlorogenic, ferulic and vanillic acids) and only one (ferulic acid) in the roots (Ghafar et al. 2001).

A sesquiterpene lactone, annuithrin, a germacranolide with an α-methylene-γ-lactone moiety, was isolated from sunflower (Spring et al. 1981). From the ethanol sunflower extract, a new germacranolide with an α-methylene-γ-lactone moiety, the heliangolide niveusin B and its ethoxy derivative, was isolated (Spring et al. 1982a). A furanoheliangolide derivative, 4,5-dihydroniveusin A, as well as niveusin B, argophyllin A and B, diterpene acid, grandifloric acid, ciliaric acid and 17-hydroxy-ent-isokaur-15(16)-en-19-oic acid were isolated from a Texas population of Helianthus annuus (Melek et al. 1985). The sesquiterpene (−)-heliespinore A, a potential allelopathic agent, was isolated from sunflower var. SH-222 (Macías et al. 1998a). Two allelochemicals, namely, sesquiterpene lactones, helivypolide D and helivypolide E and the bisnorsesquiterpene, annuionone D, were isolated from sunflower (Macías et al. 1999a). The polar bioactive fractions of Helianthus annuus cv. Stella and SH-222 yielded eight apocarotenoids, annuionones A to H (Macías et al. 2004a). Structures for annuionone A, B and E were revised. Five flavonoids, namely, the flavonol tambulin, the chalcones kukulcanin B and heliannone A and the flavanones heliannones B and C, were isolated from sunflower cultivar VYP (Macías et al. 1997). Three ionone-type bisnorsesquiterpenes annuionones A–C and the norbisabolene, helinorbisabone, were isolated from sunflower (Macías et al. 1998b). Two bioactive flavonoids heliannone A (1) and (R,S)-heliannone B (2) were identified from Helianthus annuus cultivars (Rao et al. 2001). The following allelochemicals were reported from sunflowers: (±)-heliannuol D (Vyvyan and Looper 2000), heliannuol C (Biswas et al. 2006), heliannuols A and K (Ghosh et al. 2007), heliannuol A and D (Tuhina et al. 2002) and natural enatiomers of (−)-heliespirone A and (+)-heliespirone C (Miyawaki et al. 2012). An ent-kaurane glucoside named helikauranoside A was isolated together with three known ent-kaurane-type diterpenoids: (−)-kaur-16-en-19-oic acid, grandifloric acid and paniculoside IV from sunflower aerial parts (Macías et al. 2008).