Secondary Metabolism Primary & Secondary metabolites Primary Metabolites: Secondary Metabolites: Sugar, starch, citric acid, Vitamines Pectins & algins (food additives) Phenolic compounds (coffee, vine, incense, perfumes) protein (seeds of Fabaeceae) Terpenoid compounds fatty oils (nuts, corn, (lemon scent, anis taste, bitter sesame, peanuts, sunflower, rape) taste of hops, tonic water, color cellulose (cotton, fiber, wood) Amines (smell of fish, algae, ) Alkaloids (coffeine etc.) Glycosides (Sinigrin from mustard, allicin from garlic, PEA in chocolate) Doctrine of Signatures The doctrine of signatures states that herbs that resemble various parts of the body can be used to treat ailments of that part of the body. Examples include the liverwort; snakeroot: an antidote for snake venom; lungwort; bloodroot; toothwort; and wormwood, to expel intestinal parasites. A theological justification was “The Almighty must have set his sign upon the various means of curing disease which he provided”. However some version of the doctrine exists also among Asians & Native Americans.

Medicinal plants based on the "Doctrine of Signatures" in Porta's Phytognomonica.

Plants for scaly diseases include pine cones, thistles, catkins, and lily bulbs. The snake and fish were added to show scaly skin. No doctrine but signatures Î Plants have glands

Clear giveaways = signatures = anatomical clues that plants have sequestered lots of active compounds Î glandular trichomes, lacticifers, idioblasts, resin canals, floral & extrafloral nectaries Secrets of Secretions Nectar is a sugar-rich liquid produced by plants in glands called nectaries. Nectaries are either within the flowers (Î floral nectaries)., or they are outside (Î extrafloral nectaries). In both cases they provide a nutrient source to animal mutualists. Floral nectaries are located at the bottom of the perianth, forcing pollinators to brush the flower's reproductive structures, the anthers and pistils. Extrafloral nectaries are located on the leaf petioles, mid-rib or leaf margin. Extrafloral nectaries can be found on species belonging to (amongst others) the genera Salix, Prunus (cherries) and Passiflora. Nectar can include other chemicals than sugars. 1. Nicotiana attenuata, a tobacco plant native to Utah, uses volatile benzyl acetone to attract birds but it also adds bitter nicotine to drive the bird away to visit others. 2. Rhododendrons and the California buckeye have neurotoxins such as aesculin & acetyl andromedol that do not harm bees but persist to poison the honey. Anatomical signatures Î f & ef nectaries Clear giveaways = signatures = anatomical clues that plants have sequestered lots of active compounds Î (1) glandular trichomes, (2) lacticifers, idioblasts,(3) resin canals, (4) floral & extrafloral nectaries

Nectar is a sugar- rich liquid in glands called nectaries. They are located either in flowers, or as extrafloral Position of ef nectaries Passion flower with ef varies nectaries, feeding necatries allied animals providing anti- herbivore protection Spices and perfumes – Apiacea or carrot/parsley family

Umbelliferae: umbel as inflorescense; flat-topped clusters of flowers Parsley (Petrosselinum crispum) leaf; dill (Anethum graveolens) leaf; cilantro (Coriandrum sativum) leaf and fruit (coriander spice) Spices and perfumes – Labiatea or mint family Mints have asymmetric, bilabiate (two-lipped) flowers, often in in axial nodes, square stems and opposite, fragrant leaves Rosemary (Rosmarinus officinalis), Thyme (Thymus vulgaris) antiseptic; Oregano (Origanum vulgare), Majoram (Origanum sp); Basil (Ocimum basilicum) Chatreuse; Sage (Salvia officinalis) stuffing, Peppermint (Mentha piperita); spearmint (Mentha spicata)

Picture of leaf glands Citrus family Pressurized vacuoles with essential oils protect citrus fruits. Interior of these fruits is isolated by thick cuticle and pectin layer. Simple Secretory Cells Simple secretory cells occur in the leaf parenchyma of lemongrass Andropogon spp. , bayleaf Laurus nobilis, citronella Cymbopogon spp. & patchouli Pogostemon patchouli, in the seeds of cardamon Eletteria cardamonum, the rhizome of ginger Zingiber offic. & turmeric Curcuma longa & the fruit walls of chillies Capsicum annuum, in the embryo of of nutmeg Myristica fragrans, the bark of cinnamon Cassia angustifolia & Cinnamonum zeylandicum, root of Valeriana offic. source: Secretory structures of aromatic and medicinal plants by KP & TG Svoboda Bastyr Library QK 725.S92.2002 Secrets of Secretion of Essential oils Secretory cavities are spherical intercellular spaces that are lined with one or more layers of secretory cells. These cavities are found in the peel of Citrus fruits where they appear irregularly as oblate to spherical in the pericarp, in the flavedo (yellow colored part).

source: Secretory structures of aromatic and medicinal plants by KP & TG Svoboda Bastyr Library QK 725.S92.2002 Secrets of Secretion of Essential oils Secretory cavities are spherical intercellular spaces that are lined with one or more layers of secretory cells. These cavities are found in the peel of Citrus fruits where they appear irregularly as oblate to spherical in the pericarp, in the flavedo (yellow colored part). Large secretory cavities are found in the flower buds of cloves Szygium aromaticum, the fruit walls of Pimenta dioica, the bark of myrrh Commiphora, benzoin Styrax and frankincense Boswellia and in the leaves of Eucalyptus spp. source: Secretory structures of aromatic and medicinal plants by KP & TG Svoboda Bastyr Library QK 725.S92.2002 Anatomical signatures Î glandular hairs Clear giveaways = signatures = anatomical clues that plants have sequestered lots of active compounds Î (1) glandular trichomes, (2) lacticifers, idioblasts,(3) resin canals, (4) floral & extrafloral nectaries Trichomes or hairs are fine outgrowths or appendages on Examples are hairs, glandular hairs, scales, and papillae.

Drosera leaf Coleus leaf

Cross section through stem of Digitalis or Leaf surface trichomes (Salvia divinorum). The foxglove plant shows glandular hair. upper leaf surface contains numerous multicellular, glandular and non-glandular trichomes (hairs). . Secrets of secretory hairs Glandular Trichomes are modified epidermal hairs and cover leaves, stems & the calyx in the Labiatae. Secretory cells are emanations that are either attached to a stalk or are sessile = attached to a basal cell in the epidermis. We find them in basil Ocimum basilicum, lavender Lavandula spp. Majoram & oregano Origanum spp., mint Mentha spp. & thyme Thymus spp. Secrets of Secretion of glandular hairs Glandular Trichomes are modified epidermal hairs and cover leaves, stems & the calyx in the Labiatae. Secretory cells are emanations that are either attached to a stalk or are sessile = attached to a basal cell in the epidermis. We find them in basil Ocimum basilicum, lavender Lavandula spp. Majoram & oregano Origanum spp., mint Mentha spp. & thyme Thymus spp. Also other families contain glandular hairs like hops Lupus humulus in Cannabinaeceae,

source: Secretory structures of aromatic and medicinal plants by KP & TG Svoboda Bastyr Library QK 725.S92.2002 Secrets of simple Secretion Epidermal cells. Many flowers lack glandular hairs and exude their essential oils from simple epidermal cells through the cuticle to the outside. This primitive mechanism is normally associated with very low yield of essential oils. It occurs in rose petals Rosa spp. , Acacia petals & those of jasmine Jasminum spp.

source: Secretory structures of aromatic and medicinal plants by KP & TG Svoboda Bastyr Library QK 725.S92.2002 Secrets of simple Secretion Epidermal cells. Many flowers lack glandular hairs and exude their essential oils from simple epidermal cells through the cuticle to the outside. Also buds of a number of species have simple epidermal cells that secrete resinous substances mixed with essential oils that can be used as balsams. This includes Aesculus, alnus, Betula, Populus (cottonwood , ), Prunus and Rhamnus.

source: Secretory structures of aromatic and medicinal plants by KP & TG Svoboda Bastyr Library QK 725.S92.2002 Secrets of simple Secretions Epidermal cells. Many flowers lack glandular hairs and exude their essential oils from simple epidermal cells through the cuticle to the outside. Also buds of a number of species have simple epidermal cells that secrete resinous substances mixed with essential oils that can be used as balsams. This includes Aesculus, alnus, Betula, Populus (cottonwood , Balm of Gilead), Prunus and Rhamnus.

Poplar Tree Leaf Bud Extract Could Fight Skin Aging ScienceDaily (June 8, 2011) — Antioxidants are popular anti-aging ingredients in skin creams, and now scientists are reporting a new source of these healthful substances -- leaf buds of poplar trees. Their study appears in the ACS' Journal of Agricultural and Food Chemistry. How to make Balm of Gilead salve! Poplar Tree Leaf Bud Extract Could Fight Skin Aging ScienceDaily (June 8, 2011) — Antioxidants are popular anti-aging ingredients in skin creams, and now scientists are reporting a new source of these healthful substances -- leaf buds of poplar trees. Their study appears in the ACS' Journal of Agricultural and Food Chemistry. 1. Collect buds in late winter. Ecological best is to wait until they fall down on their own after the young leaves push them 2. Extract resin by slowly simmering the buds in hot olive or other oil to release their resin, or place buds in a crock, cover them with oil, leaving them to “steep” for weeks or months 3. Make 1:1 ratio of beeswax or myrtle wax shavings and add it to warm (not hot) oil extract. Stir with wooden tool. 4. Some additions could include lanolin, vitamin E oil or coconut oil, all of which slightly change the properties and texture of the salve. Experiment with small batches Anatomical signatures Î lactifers Clear giveaways = signatures = anatomical clues that plants have sequestered lots of active compounds Î (1) glandular trichomes, (2) lacticifers, idioblasts,(3) resin canals, (4) floral & extrafloral nectaries

Latex is the stable dispersion of natural or synthetic microparticles in an aqueous medium.

Latex is a milky fluid found in 10% Hevea or rubber tree of all flowering plants.

It consists of proteins, alkaloids, starches, sugars, oils, tannins, resins, and gums that coagulates on exposure to air. It is usually exuded after tissue injury. poppies . Cut Euphorbia Euphorbia lathyris or Caper spurge is an erect biennial plant of European origin growing up to 1.5 m tall, with a glaucous blue-green stem and decussate opposite lanceolate leaves. All parts of the plant, including the seeds and roots are poisonous. Handling may cause skin irritation as the plant produces latex. While poisonous to humans and most livestock, goats eat it and are immune to the toxin. However, the toxin can be passed through the goat's milk

This plant is a good source of copious amounts of latex. Since the latex is an emulsion of hydrocarbons in water, this plant was investigated as a possible source of making petroleum. But then the oil prices dropped again and ...da da da Herbivores ... Help ...Herbivores

These are only the zoological antagonists of plants. You add to this representatives of the bacteria, fungi & other plants. Plants and Insects The majority of animals is herbivorous = feeds on plants! Spines, thorns, cuticle, camouflage, repelling smell, taste & deadly toxins are the reason that plants keep dominating (95 %!) the planet’s biomass Herbivores feed only on one to a few plant species because they can only overcome a few of the defense mechanisms. Even humans (only herbi species that cooks & selects population featuresby breeding) feed only on very small number of plants out of the 400 000 species on the planet. E.g. we feed only on the petioles of rhubarb leaves & discard the oxalate-rich blades. H Milky caustic, toxic juice flows through many plants with lactifers (pressurized vessels running in parallel with water- transporting xylem & sugar- transporting phloem). Occurring in Apocynaeceae, Euphorbiaecea, Asteraecea, Caricaceae, Moracea Why do Plants produce a Latex Polymer? 1905 H Kniep carried out classical experiment on chemical defense in plants. By repeated poking the midvein of Euphorbias he drained/milked them & found them now being eaten by snails. Kniep did not know that some insects have practiced his method regularly to avoid being poisoned or muzzled alive!

Drain the lactifer defense chemicals or suffer the consequences!1 R: Thomas Eisner “ For love of insects” Harvard University Press, 2003 Can Plants produce a Polymer muzzle for Insects? 1905 H Kniep carried out classical experiment on chemical defense in plants. By repeated poking the midvein of Euphorbias he drained/milked them & found them now being eaten by snails. Kniep did not know that some insects have practiced his method regularly to avoid being poisoned or muzzled alive!

Drain the lactifer defense chemicals or get muzzled !!!

R: Thomas Eisner “ For love of insects” Harvard University Press, 2003 Olmecs invented games with rubber balls

Visitors to the Amazon describe how Indians coated their feet with latex to be protected from … One of the most mystique nations of Central America were the Olmecs which invented ball games -a most important invention in the history of (wo)mankind. Anatomical signatures Î “Plants have idioblasts” Clear giveaways = signatures = anatomical clues that plants have sequestered lots of active compounds Î (1) glandular trichomes, (2) lacticifers, idioblasts,(3) resin canals, (4) floral & extrafloral nectaries Idioblasts are isolated cells which differ from neighboring plant cells by containing non-living substances. They store starch, excretory materials, pigments and minerals and can contain Ca oxalate raphides emerge from oil, latex, gum, resin, tannin or pigments irritated idioblasts etc. Some can contain mineral crystals such as acrid tasting and poisonous calcium oxalate or silica. Idioblasts are divided into three main categories: excretory, tracheoid and sclerenchymatous. When the end of the idioblast is broken the crystals or other substance is Cross sections of petals of various plants ejected by internal water pressure showing idioblasts around the vascular ring. CH Polymers: Resins

Resin is another hydrocarbon secretion of plants, particularly coniferous trees. It is used for production of varnishes, adhesives,; as an important source for incense and perfume. Resins likefrankincense and myrrh originate from ancient Egypt. Some resins are Some resins are soft & known ancient and as 'oleoresins', and when hardened like containing benzoic acid or amber. Amber cinnamic acid they are called often has balsams. Example inclusions of Balm of Gilead is a balm perfectly preserved (healing compound) made from fossil life ( known the resin of the buds of balsam from Jurassic poplar (Populus candicans), a Park). North American tree species. Anat. Signatures ÎPlants have resin ducts Clear giveaways = signatures = anatomical clues that plants have sequestered lots of active compounds Î (1) glandular trichomes, (2) lacticifers, idioblasts,(3) resin canals, (4) floral & extrafloral nectaries resin ducts are tubes that serve the defense against insects and other animals, which are engulfed by the Resin canals below the when boring into the hypodermis of pine leaf conifer's leaves.. Resin acids are protectants and wood preservatives that Mountain pine beetle drills into pine are produced by bark and encounters parenchymatous cells that resin flow, which surround the resin ducts could kill it. Poison oak fruit with resin canals.

resin ducts and resin blisters in balsam fir resin ducts are tubes that serve the defense against insects and other animals, which are engulfed by the when boring into the conifer's leaves.. Balsam fir Abies balsamea shows prominent Resin acids are protectants raised blisters full of resin (end of resin ducts) and wood preservatives that Mountain pine beetle drills into pine bark and encounters resin flow, which could kill it.

Resin became amber and pests became jewelry =Î Jurassic Park is the resin of trees

Mastic or Masticha is the resin from the Pistacia Lentiscus tree. The trees are commercially cultivated for the purpose of harvesting mastic tears. The very best mastic is said to come from the south side of the Greek Island of . The resin dries on the bark into a Clear, crystalline “tears” which are collected at the end of August,) The teardrops were the first version of in . As you masticate, they soften into a firm, chewy mouthful with flavors of licorice and pine. Typically mastic is sold as teardrops although it can also be found as a paste or a powder. The teardrops must usually be ground to a fine powder, usually with sugar, in order to be used for culinary purposes. Chewing Gum The original chewing gum was an invention of native Americans – the Mayans and them Northern tribes. Native American habits easily mislead the innocent White and Black invaders/ newcomers (Indian magic). (1) smoking tobacco (2) chewing tobacco and now (3) chewing gum.

•The ancient Greeks chewed mastiche - a chewing gum made from the resin of the mastic tree. •The ancient Mayans chewed chicle which is the sap from the sapodilla tree. •North American Indians chewed the sap from spruce trees and passed the habit along to the settlers. Resins –purifying incenses of old Mastic is the resin Pistacia lentiscus growing in only a few villages of the island of Chios. Wounded Pistachio trees have resin flow in August. is chewed like chewing gum. Î word masticate, trad. Greece Gum Benzoin is resin produced by the tall Styrax trees (S. benzoin & S. tonkinense) native to Indochina, also called the Java incense trees growing no taller than a person. Gum benzoin was used in Chinese perfumes due to its stable aroma, also in massage oil. The wounded bark fills with yellow fluid that hardens into a reddish mass. Gum guggul myrrh –like resin from the Iranina thorn tree Commiphora mukul, native to western Iran and Eastern India, perfume of Persian women at the time of Alexander’s conquest.. Balsam of Gilead, Balm of Mecca. Resin from 3 m tall trees of Commiphora opobalsamum native to Southern Yemen, kingdom of Saba (queen of Sheba’s gift to Solomon), later planted from Egypt to Palestine, remedy for ringworm + skin diseases. B of Gilead from N. American Populus candicans Î Flowers to Perfumes Î Labdanum

Labdanum is a sticky brown resin obtained from Cistus creticus the Cistus ladanifer (western rockrose Mediterranean) and Cistus creticus (eastern Mediterranean), species of rockrose. It has a long history of use in herbal medicine and as a perfume ingredient. In ancient times, resin was scraped from fur of goats and sheep that grazed on the cistus shrubs. The false beards worn by the pharaohs were actually the labdanum soaked hair of these goats. Labdanum is produced today for the perfume industry: The raw resin is usually extracted by boiling the leaves and twigs. The raw gum is a dark brown, rockrose harvest in fragrant mass It resembles Crete ambergris, which has been Benzoic acid in perfumes Benzoin resin = styrax resin = benzoin is obtained from the bark of trees in the genus Styrax. Benzoin Sumatra is obtained from Styrax benzoin grown on the island of Sumatra. Both varieties are pathogenic resins, which are exuded from the tree when it is damaged. Its principle component is benzoic acid.

In perfumery, benzoin is used as a fixative, slowing the dispersion of essential oils & other fragrances into the air. It is also used in medicine. Tincture of benzoin has two main medical uses: aseptic treatment for blisters damaged Leukoptape + skin, and as an inhalant in case of bronchitis & asthma. TOB treats blisters on Benzoin resin is important aroma in incensestrips: major comp. of incense of Russian Orthodox Christians also in Japanese incense, Indian incense, Chinese incense, and Papier d'Arménie. Sambrani is a popular Indian incense used to scent hair and prevent infections. Asafoetida – the ersatz Silphium of Greek antiquity Asafoetida = Europe’s forgotten spice? a repulsively smelling resin from the Iranian Fennel Ferula asa-foetida often adulterated with F. persica & F. galbanum – all tall stout umbellifers The secret of it was first discovered by Engelbert Kaempfer who travelled in Iran & Turkey under cover and wrote 1712 “Five studies ofexotic wonders, political, scientific and medical” Resins –purifying incenses of old Sandalwood: from wood and root of parasitic trees Santalum album, wounding causes gum to flow Î pure native to Indonesia and India. 1000 BC use in India as incense, perfume to enhance sexual attraction (sandalwood resembles male pheromone) and in oil paste applied as UV-protecting sunscreen! Red Sandalwood gives red powder like Santalum but lacks aroma. derived from different trees Pterocarpus santalina that form forests in Madagascar. Decorative wood for pagodas, statues etc. , spice in marzipan & biscuits. Aloeswood resin from tree Aquilaria mallantis native to Eastern has black hard dense wood. Muslim kingdom of Champa (South Vietn) Chinese med. uses it for nervousness, Ayurveda for mental illness. Myrrh reddish-brown resin from dried sap of tree Commiphora myrrha, native to Yemen & Somalia (Punt). Unlike other resins, myrrh expands and "blooms" when burned instead of melting or liquefying .not related to Myrrhis odorata = sweet cicely Secrets of Secretory Ducts Secretory ducts are elongated cavities that branch into networks that often pass between root and shoot. The cavities are lined with secretory cells, where the leucoplast produce the terpenes of the essential oils and secrete them into the cavity.

Another famous example are the resin ducts of in the xylem of the Coniferae reaching 4-10 cm length with 1 to 7 ducts per leaf. Here is the fruit of Juniperus communis Î source: Secretory structures of aromatic and medicinal plants by KP & TG Svoboda Bastyr Library QK 725.S92.2002 Secrets of Secretory Ducts Secretory ducts are elongated cavities that branch into networks that often pass between root and shoot. The cavities are lined with secretory cells, where the leucoplast produce the terpenes of the essential oils and secrete them into the cavity.

Another famous example are the resin ducts of in the xylem of the Coniferae reaching 4-10 cm length with 1 to 7 ducts per leaf.

Here are ducts from needles of Cedrus libanii Î source: Secretory structures of aromatic and medicinal plants by KP & TG Svoboda Bastyr Library QK 725.S92.2002 Gum-producing plants