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Bot Med 2 > Plant Chemistry > Flashcards

Plant Chemistry Flashcards

1
Q

Pharmacognosy is:

A

the study of the physical, chemical, biochemical and biological properties of drugs, drug substances, or potential drugs or drug substances of natural origin as well as the search for new drugs from natural sources

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2
Q

Why should we study pharmacognosy?

A

to inform our decisions about crafting medicines, how to administer, potential interactions, and physiologic actions.

tea or tincture? how is it absorbed? stability of constituents? constituents present in essential oil? etc

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3
Q

What are secondary metabolites?

A

compounds not directly involved in the growth, reproduction, or photosynthesis of plants.

generally associated with defense, attraction of pollinators and symbiotes, & protection from environment (like UV)

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4
Q

Aromatic (benzene) ring with an -OH group:

A

Phenolics

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5
Q

Properties of phenolic constituents:

A
  • resonance stabilization
  • antioxidants
  • anti-inflammatories
  • anti-cancer
  • colorful pigments
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6
Q

T/F: Plant chemicals are group according to their chemical action on the body.

A

False!

they’re organized by their chemical structure

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7
Q

Simple phenolic compounds - properties:

A

single aromatic ring
smaller molecules are volatile
often form glycosides

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8
Q

Phenolic glycosides - properties:

A

phenolic with a sugar group

[aglycone + glycone]

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9
Q

Phenolic acids - properties:

A

at least one phenolic ring with an acidic carboxyl group

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10
Q

Tannins - properties:

A

astringents
phenolic acids w/ester [-o-] linkages to a sugar molecule
tighten tissues - taste dry in your mouth!

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11
Q

Derivatives of α-pyrone:

A

Coumarins

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12
Q

Coumarins with an additional O-heterocycle:

A

Furanocoumarins

these are photosensitizing

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13
Q

Properties of coumarins:

A
  • antioxidant
  • anti-inflammatory
  • appetite suppressant
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14
Q

Pigmented molecules:

A

Naphthoquinones

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15
Q

Properties of naphthoquinones:

A
  • fungicidal
  • antibacterial
  • insecticidal
  • phytotoxic
  • cytostatic
  • anticarcinogenic
  • antihelminthic
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16
Q

Polyphenolic compounds based on tri-aromatic ring structure with opposite phenolic groups on the middle ring:

A

Anthraquinones

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17
Q

Properties of anthroquinones:

A
  • laxative and purgatives
  • many are pigments
  • many are glycosides
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18
Q

Properties of flavonoids:

A
  • anti-cancer
  • anti-inflammatory
  • cooling
  • colorful
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19
Q

3-ring molecules with one benzene ring connected by only one carbon bond (usu 2 or 3):

A

flavonoids

20
Q

Structurally similar to flavonoids, but carrying a charge:

A

anthocyanidins

called anthocyanins when they have a glycoside

21
Q

Properties of anthocyanidins:

A
  • sap pigments (color depends on pH)
22
Q

Properties of anthocyanins:

A
  • odorless
  • flavorless
  • mildly astringent
23
Q

Properties of proanthocyanidins:

A
  • related to flavonoid pigments
  • no sugar moiety
  • oligomers & polymers of flavon-3-ol’s
24
Q

Dimeric compounds formed by two phenylpropene derivatives:

A

Lignans

25
Q

Properties of lignans:

A
  • major class of phytoestrogens
  • antioxidant function
  • some have toxicity
  • some are hepatoprotective
26
Q

Phenylpropene units linked head-to-head or head-to-tail:

A

Neolignans

27
Q

Synthesized from DMAPP and IPP 5-C precursors:

A

Terpenoids

28
Q

Characteristics of monoterpenes:

A

10-C molecules
low molecular wt
structural variations: monocyclic, bicyclic, acyclic
component in essential oils
small change in structure -> big change in action

29
Q

Cyclic structure with an Oxygen in the ring neighboring a ketone:

A

Lactone

30
Q

A cyclopentane ring fused to a 6-membered oxygen heterocycle, often occur as glycosides:

A

Iridoid - these are bitters

31
Q

Characteristics of sesquiterpenes:

A

15-C molecules
volatile
structural variations: monocyclic, bicyclic, acyclic

32
Q

A mixture of terpenoid molecules & aromatic compounds that combine to form a (semi-)solid substance that is excreted by plants for protection or in response to injury. :

A

Resin

The (semi-)solid portions are often di- & triterpenes
The aromatic portion is commonly mono- and sesquiterpenes

33
Q

Resins that have a polysaccharide component as well as volitile oils and heavier terpenes:

A

Gum resin

34
Q

Characteristics of triterpenes:

A 
30-C molecule
usu pentacyclic
precursor to plant steroids
usu water-soluble saponins
aglycones are oil soluble
35
Q

Amphipathic:

A

a chemical compound possessing hydrophilic and lipophilic properties.
e.g. triterpenoid saponins like glycyrrhizin

36
Q

Characteristics of steroidal saponins:

A

27-C molecule
multiple sugar units attached (usu 3-5)
many anti-inflammatory & adaptogenics in this class
“-genin” denotes the aglycone

37
Q

Characteristics of phytosterols:

A

tetracyclic
plant equivalent to cholesterol in animal cell membranes
plant growth regulators
found in plant oils and lipophilic extracts

38
Q

Characteristics of cardiac glycosides:

A

Tetracyclic sterol skeleton w/5-membered lactone ring

cardioactive substances from plants (digitalis, convallaria)

39
Q

Characteristics of tetraterpenes:

A

40-C molecules
lipophilic - multiple conjugated double bonds
terminal cyclic structures
lycopene is precursor
carotenoids concentrate in tissues providing antioxidant protection

40
Q

Oxygenated carotenoids are called:

A

Xanthophylls

they have ketone, hydroxyl, and epoxide groups on their rings

41
Q

Characteristics of alkaloids:

A

nitrogenous molecules (N in the ring)
occur as salts or N-oxides in plants
alkaline nature
soluble in hydroethanolic menstrum

42
Q

How do amines differ from alkaloids?

A

In amines, the N is not within the ring.

43
Q

Toxic alkaloids that build up in tissues over time and have a hepatotoxic & hepatocarcinogenic effect:

A

Pyrrolizidine alkaloids

Comfrey, butterburr, colt’s foot

44
Q

Characteristics of inulin:

A 
oligosaccharide
prebiotic
soluble fiber
named for inula helenium
sources: chicory, onion, garlic, artichoke, dandelion, burdock
45
Q

Heteropolysaccharides that can trap water in a 3D structure:

A

Pectins

  • soluble fiber
  • helical galacturonic acid backbone, various sugar side groups
46
Q

Characteristics of a mucilage:

A

forms gel/slime with water
soothing & emollient
significant crossover btw mucilages & immunomodulating polysaccharides
found in althea off, ulmus fulva

47
Q

Complex mix of heteropoly- & polysaccharide protein complexes that effect immune system function:

A

Immunomodulating polysaccharides

  • arabinogalactans
  • acemannans
  • beta-glucans

Bot Med 2 (7 decks)

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