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Chemosystematics of Some Conifers of India

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Chemosystematics of Some Conifers of India Proc. Indian Acad. Sci. (Plant Sci.), Vol. 99, No. 3, June 1989, pp. 253-258. O Printed in India. Chemosystematics of some conifers of India SHEEJA M JOHN, M DANIEL and S D SABNIS Phytochemistry Laboratory, Department of Botany, Faculty of Science, M S University of Baroda, Baroda 390 002, India. MS received 6 June 1988; revised 13 December 1988 Abstract. Flavonoids and related phenolics in the leaves of 14 conifers were studied and their relevance in the taxonomy of the group was assessed. It is found that biflavones were absent from the Pinaceae and Taxaceae. The former family was also devoid of flavones and possessed a low frequency of incidence of flavonols. The entire flavonoid system was absent in Pinus. In the light of these chemical evidences, the identities of the Pinaceae and Taxaceae as separate orders Pinales and Taxales, are defended. The rest of the conifers are grouped in a new order, the Cupressales. The merger of Taxodiaceae and Cupressaceae is strongly opposed. Incorporating all the taxonomic evidences a new scheme of classification is proposed. Keywords. Chemotaxonomy;conifers; Pinales; Taxales; Cupressales; biflavones. 1. lntroduction The conifers are the representative gs'mnosperms of the present flora and constitute more than three fourths of the gymnosperms. In India 12-15 genera of conifers, containing more than 20 species, are available, mostly distributed in the Himalaya. Coulter and Chamberlain (1917) recognised two families of conifers, the Pinaceae and the Taxaceae. The Pinaceae possess distinct female strobili in which the overlapping scales protect the ovules. This family is divided into 4 tribes: (i) Abietineae, (ii) Taxodineae, (iii) Cupressineae and (iv) Araucarineae. The Taxaceae are a group in which distinct strobili are not formed and ovules are frequently exposed. This contains two tribes: (i) Podocarpineae and (ii) Taxineae. Since the Cephalotaxus possesses ovules arranged in cones and due to the interpretation that the solitary ovules of some Podocarps represent the ultimate stage in the reduction (and nota solitary terminal ovule as in Taxaceae), Pilger (1926) separated Cephalotaxus and Podocarpus from Taxaceae. He also raised many of the tribes of Coulter and Chamberlain (1917) to families. His order Coniferales contained 7 families i.e. the Taxaceae, Podocarpaceae, Araucariaceae, Cephalotaxaceae, Pinaceae, Taxodiaceae and Cupressaceae. Sahni (1920) and Florin (1958) recognised Taxales asa separate order containing Taxaceae and Cephalotaxaceae. Benson (1957) transferred Podocarpaceae and Cephalotaxaceae to Pinales and retained Taxaceae in Taxales. Sporne (1965) accepted this concept and classifŸ the conifers in two orders i.e. order Coniferales containing the Pinaceae, Taxodiaceae, Cupressaceae, Podocarpaceae, Cephalotaxaceae, Araucariaceae and the order Taxales with a single family, Taxaceae. In a recent schetne of classification, Keng (1975) brought Podocarpaceae and Cephalotaxaceae back into his Taxales while retaining the remaining families in Pinales. Based on a wide array of features ranging from gross morphology to phytochemistry, Eckenwalder (1976) proposed a merger of Taxodiaceae and Cupressaceae with the latter name having priority for the enlarged family. 253 254 Sheeja M John, M Daniel and S D Sabnis Conifers attracted the attention of the phytochemists because of the special polyphenolic compounds, the biflavonoids. These flavone-dimers, which were considered unique to some of the groups of gymnosperms, are now found to be occur¡ in many vascular plants. However, the near uniform presence of these compounds in certain orders of gymnosperms make them taxonomically significant. The absence of these compounds from Gnetales led to a strong debate on the validity of including this order in gymnosperms. Among conifers almost all the screened members of Pinaceae were found to be devoid of these compounds. Though biflavones were reported from the Taxaceae, these results are considered to be of questionable value because of the limitations of the techniques used and the failure of confirming their presence by later workers (Geiger and Quinn 1975). In the present study leaves of 14 conifers available in India have been screened for their flavonoids and related phenols. The plants studied belong to the genera Abies, PŸ Cedrus, Pinus (2) (Pinaceae), Taxodium (Taxodiaceae), Cupressus, Thuja, Juniperus (2) (Cupressaceae), Podocarpus (Podocarpaceae), Araucaria (Araucariaceae) Cephalotaxus (Cephalotaxaceae) and Taxus (Taxaceae). Of these Araucaria and Taxodium ate introductions to India. The data thus obtained have been utilised to assess the taxonomy of the group. A number of conifers have been studied for their terpenoids and sugar alcohols (Gibbs 1963). The wood phenolics of Pinus also ate extensively studied. The previous reports on the leaf flavonoids of the plants screened include sciadopitysin, amentoflavone and sequoiaflavone from Cephalotaxus (Khan et al 1971), amentoflavone and sciadopitysin from Taxodium distichum (Geiger and De Groot- Pfleiderer 1973), sciadopitysin and cupressuflavone from Juniperus recurra (Hameed et al 1973), amentoflavone and hinokiflavone from Thuja orientalis (Pelter et al 1970), amentoflavone and hinokiflavone from Araucaria cunninghamii (Geiger and Quinn 1975) and flavones and/or flavonols as well as proanthocyanidins from Thuja, Juniperus and Taxodium (Niemann 1988). 2. Mate¡ and methods Most of the plants were collected from the forests of Kashmir (Gulmarg and Pahalgam) where the vegetation is exclusively of conifers. Taxodium was available in Mahabaleshwar and Podocarpus from the Botanical garden of Poona University. The leaves of flowefing/fruiting shoots were used for the investigation. Al1 the plants have been identified and voucher specimens are deposited in the Herbarium of the University. Standard procedures (Harborne et al 1975; Markham 1982; Harborne 1984) were followed for the isolation and characterisation of the various flavonoids and stilbenes. 3o Results The distribution of various flavonoids and stilbenes in the leaves of 14 conifers is presented in table 1. It is found that 12 plants possessed flavonoids in their leaves. The different flavonoids encountered were flavones, flavonols, biflavones and proanthocyanidins. Flavones, flavonols and biflavones were seen in 10 plants. All the 4 plants which were devoid of the above mentioned compounds belonged to the Pinaceae. Table !. The distribution of various flavonoids and stilbenes in the leaves of certain conifers of India. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 Coniferales Pinaceae t~ Abies pindrow Spach. + + Cedrus deodara Loud. + + + + Picea smithiana Boiss. + + Pinus roxburtlh¡ Sarg. + P. wallichiana A B Jackson + Taxodiaceae Taxodium distichum Rich. + + + + Cupressaceae Cupressus sempervirens Linn. + + + + + + + + Juniperus communis Linn. + + + J. recurra Hato. + + + + Thuja orientalis Linn. + + + + + + Cephalotaxaceae + + + + Cephalotaxus .qriffithii Hk. f. E" Podocarpaceae Podocarpus neriifolius D Don. + + + + Araucariaceae Araucaria cunnin.qham¡ Ait + -4- Taxales Taxaceae Taxus baccata Linn. + + + + 1, Acacetin; 2, luteolin; 3, kaempferol; 4, quercetin; 5, 3-OMe quercetin; 6, 3'-OMe quercetin; 7, 3',4'-DiOMe quercetin; 8, myricetin; 9, cupressuflavone; 10, amentoflavone; 11, sciadopitysin; 12, kayaflavone; 13, hinokiflavone; 14, proanthocyanidins, 15, stilbenes, t.o L~ 256 Sheeja M John, M Daniel and S D Sabnis Flavones were located in 4 plants belonging to Cupressaceae, Araucariaceae and Taxaceae. Acacetin and Luteolin were the two flavones present in these plants. Flavonols were more widespread, having been located in 8 plants. The various flavonols identified were kaempferol (1 plant), quercetin (1) various methoxylated derivatives of quercetin (7) and my¡ (3). Araucaria and most of the members of Pinaceae were devoid of these compounds. Biflavones were seen in all the plants belonging to the Taxodiaceae (Taxodium), Cupressaceae (Cupressus, Thuja and Juniperus), Cephalotaxaceae (Cephalotaxus), and Podocarpaceae (Podocarpus). Cupressuflavone, amentoflavone, sciadopitysin, kayaflavone and hinokiflavone were the biflavones identified. None of the plants belonging to the Pinaceae, Araucariaceae and Taxaceae contained these compounds. Proanthocyanidins were located in all the plants except the two species of Pinus. Most of the proanthocyanidins identified were procyanidin and its methoxylated derivatives. Prodelphinidin and propelargonidin and their de¡ were rare. Stilbenes were present in all the members of the Pinaceae screened and were characteristically absent from all other plants. 4. Discussion Based on the dist¡ of flavones, flavonols, biflavones and stilbenes, 3 groups of conifers are visualised. The first group containing the Pinaceae, is very distinct in containing stilbenes confined to it and in not having biflavones or flavones. This group has a very low incidence of flavonols (1/5). The second group, inclusive of the Taxodiaceae, Cupressaceae, Podocarpaceae, Cephalotaxaceae, and Arauca¡ characteristically produces biflavones. Flavones and flavonols are widespread here and stilbenes are absent. The third group contain the Taxaceae and is different from both the other groups in the absence of biflavones and/or stilbenes. Since the Pinaceae have been found to be chemically distinct from the rest of the conifers, this family warrants a separate status away from other conifers. The absence of biflavones from Pinaceae was cited by Baker and Ollis (1961) in support for the
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