AROMA 502 | HERB 521

A Phytochemical in a matrix

The asorbic acid molecule is exactly the same in oranges or violets, but is embedded in very different chemical matrices.

Chemistry's Dynamic Matrix: The Living Plant

The asorbic acid molecule is exactly the same in oranges or violets, but is embedded in very different chemical matrices.

St. Johnswort, Hypericum perforatum

Hypericum exhibits synergistic action between hyperforin, hypericin, & other constituents including flavonoids and xanthones. Hyperforin is a type of phloroglucinol derivative, which is a type of polyphenol; hypericin is a bianthraquinone (aka naphthodianthrone), which is a type of quinone, which is a type of polyphenol; flavonoids are a type of polyphenol.


Dandelion, Taraxacum officinale

  • Synergism: "The combined action of constituents is greater than would be expected from a consideration of individual contributions" *
  • Polyvalent action: "A way of approaching treatment from several angles concurrently...multiple active constituents" *

*Synergy definitions from Trease & Evans ‘Pharmacognosy,’ 15th Ed. Pp 49-50. See ESCOP article on Synergy: See: J. Barnes. 1999. A close look at synergy and polyvalent action in medicinal plants. Inpharma 1185:3-4.

Examples of Synergy

Morning Glories, Ipomoea spp.

Herbs or Drugs?

Modern pharmaceuticals are often single purified chemical compounds. Not so long ago, many were botanicals with synergistic phtyochemical profiles.

Herbal drugs from Parke-Davis, Wonder Tower Museum, Genoa, KS

Violet, Viola spp.

Orange, Citrus sinensis

Ascorbic acid (reduced form; ascorbic acid is a type of organic acid), also known as ‘Vitamin C’

Kinds of Synergy

Ginkgo, Ginkgo biloba

  • Potentiating synergy: Enhancement of activity
  • Stabilization synergy: Protecting unstable constituents
  • Modification synergy: attenuation of toxicity

The polyphenolic compounds (flavonols, proanthocyanidins) & the terpenoid compounds (diterpene lactones or ginkgolides) have been demonstrated to work together synergistically.

Orange, Citrus sinensis (Blood Orange is Citrus sinensis v. sanguinella)

In a whole plant, multiple antioxidants work together in a process known as 'redox cycling' where they reactivate one another and prevent pro-oxidant activity

  • Citrus bioflavonoids (~60 kinds known)
  • Carotenoids (~20 known)
  • Vitamin C
  • Anthrocyanin (in Blood Oranges)

See: Maccarone, E. et. al. 1998. Cyanidin-3-(6"-Malonyl)-glucoside. An Important Anthocyanin of Blood Orange Juice. Ital. J. Food Sci. 10:367.

Black Pepper, Piper Nigrum

  • Ayurvedic "Trikatu" contains Black Pepper (Piper nigrum); enhances actions of other herbs in traditional formulas
  • Piperine is an alkaloid isolated from P. nigrum
  • Increased absorption of other constituents when taken concurrently
  • Delays catabolism of other constituents

See: Effect of Trikatu (Piperine) on the Pharmacokinetic Profile of Isoniazid in Rabbits,

Wild Licorice, Glycyrrhiza lepidota

  • Liquorice used in TCM with processed Aconite (Monkshood) to attenuate toxicity
  • Study: In a formula with aconite and ginger, increasing the amount of Liquorice decreased the amount of aconite that could be extracted.

Aconitine is the principle toxic alkaloid in Aconite. Glycyrrhiza lepidota is a relative of G. glabra which grows in the Western United States. See: P. Miaorong and L. Jing, pp 28-30, Proc. 40th Ann. Conf. Beijing Univ. Chinese Med., 1996.

Polyvalent Plantain

English or Narrow-leaf Plantain, Plantago lanceolata

Broad-leaf Plantain, Plantago major

  • Antiseptic: Aucubin
  • Astringent, drawing: tannins
  • Anti-inflammatory: flavonoids, iridoids
  • Skin healing: Mucilage, allatoin, tannins, sorbitol

Polyvalent: having multiple modes of action

Plantago major & P. lanceolata contain:

  • Iridoids: aucubin [0.3-2.5%], catalpol [0.3-2.1%], asperuloside (iridoids are a subclass of monoterpenes, which are a type of terpenoid) (aucubin degrades with heat or drying; best obtained in fresh plant material)
  • Flavonoids (a type of polyphenol)
  • Phenolic acids (a type of polyphenol)
  • Phenylpropanoid glycosides (a type of polyphenol)
  • Heteropolysaccharides containing D-galactose, L-arabinose, & ~ 40% uronic acids Allantoin (a nitrogenous derivative of urea)

References: Chiang, L.C., et. al. 2002. Antiviral activity of Plantago major extracts and related compounds in vitro. Antiviral Research 55:53-62.

Rønsted et. al. 2000. Chemotaxonomy of Plantago. Iridoid glycosides and caffeoyl phenylethanoid glycosides. Phytochemistry 55:337-348.

Synergy and Antioxidants

How do antioxidants work?

1. Free radicals are highly reactive and can damage other molecules, especially lipids and cell membranes.

2. The antioxidant can donate an electron to the free radical, which will neutralize it.

3. The antioxidant donates the "loose electron"

4. The free radical then has two electrons and is neutralized, but what about the antioxidant?

Why we need multiple Antioxidants

1. Some radicals can be stable because they have features which counterbalance the loss of an electron. Also, two radicals can join up to neutralize each other.

2. Stronger antioxidants reactivate weaker ones...

3. ---until a stable, harmless radical is formed

Copyright Notice : All material (other than photographs copyrighted to others, as noted, & original historical botanical illustrations as listed above) in Plant Constituents for Herbalists: Supportive Science for Herbal Medicine, is © 2003 - 2005 Lisa Ganora. Copyright protected under the Digital Millennium Copyright Act [http://]. Any use of materials in this presentation, including reproduction, distribution, or republication, in print or on a website, without prior written permission of the author, is strictly prohibited. All rights reserved. The information presented here is for educational purposes only. It is based on scientific studies, clinical results, or traditional usage as noted. The effects listed may not necessarily occur in all individuals. This information is not a substitute for health care from qualified practitioners. Contact: Lisa Ganora,

All rights reserved. © American College of Healthcare Sciences 2020

5005 S. Macadam Ave, Portland, OREGON • • DEAC ACCREDITED