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753 Terms

1

cancer

- rapid and uncontrolled formation and growth of abnormal cells in the body

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carcinogen

- cancer-causing substance, nicotine (Tobacco leaves, Tannins)

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may apple (Podophyllum peltatum)

- root extract useful for treating skin cancers

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may apple - active ingredient

- aliphatic alkaloids and podophyllin
- podophyllotoxin and alpha-peltatin

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podophyllotoxin

- destabilizes microtubules and prevents cell division and DNA replication
- treat HPV
- derivatives used to treat cancer
- embryotoxic

<p>- destabilizes microtubules and prevents cell division and DNA replication<br>- treat HPV<br>- derivatives used to treat cancer<br>- embryotoxic</p>
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autumn crocus (Colchicuma autumnale)

- extracts inhibit cell division
- contains colchicine ALKALOID

-disrupts spindle formation during mitosis

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colchicine

- alkaloid
- inhibits mitosis
- disrupts microtubules
- treat Gout
- derivatives used to cancer
- narrow therapeutic index
- can damage bone marrow

<p>- alkaloid<br>- inhibits mitosis<br>- disrupts microtubules<br>- treat Gout<br>- derivatives used to cancer<br>- narrow therapeutic index<br>- can damage bone marrow</p>
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red clover (Trifolium pratense)

- contains isoflavone genistein as an antioxidant
- evidence for effectiveness against breast cancer

-Salve made from the flowers

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Pacific yew (Taxus brevifolia)

- contains taxol (paclitaxel)
- shade tree in temperate rainforest

-gymnosperm

-Endemic to pacific coastal rainforests of the mountains

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taxine

- toxic alkaloid mixture, made of 7+ alkaloids

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English yew (Taxus baccata)

- wood historically used for axe handles and bows
- second oldest tree on the planet

-Economic use in Europe

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genus Taxus

- evergreen shrubs
- contain taxine

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taxol (paclitaxel)

- alkaloid
- active anti-cancer agent
- not an ingredient in taxine
- concentrated in the bark (2g in 15kg of bark)
- hydrophobic so IV delivery is difficult

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taxol - mechanism

- M phase of the cell cycle, blocks replication
- binds to microtubules and prevents spindle disassembly
- interrupts cell cycle (anaphase/telophase) and growth is stopped

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taxol analogues

- may be more effective than taxol

not cost effective

Very hydrophobic normally- analogues can improve water solubility

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Taxol supply problems

treatment = 2g

requires 15kg of bark

would need 25000kg of bark to meet demand

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Madagascar periwinkle (Catharanthus roseus)

- traditionally used for wasp stings, stop bleeding, eyewash, adn diabetes treatment

  • not traditional anti cancer
    - extracts (vinblastine and vincristine) inhibits leukemia

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vinblastine and vincristine

- anti-cancer
- treat acute lymphoblastic leukemia
- help with Hodgkin's

<p>- anti-cancer<br>- treat acute lymphoblastic leukemia<br>- help with Hodgkin's</p><p></p>
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vinblastine and vincristine - mechanism

- during M phase
- block microtubule assembly during prophase

Spindle does not form, mitosis is arrested; cell replication is inhibited

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bloodroot (Sanguinaria canadensis)

- traditionally used sap to treat breast cancer
- used in conjunction with surgery to treat skin cancers
- contains sanguinarine (Alkaloid)

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sanguinarine

- alkaloid
- used to treat skin cancer
- used in oral rinses and toothpastes- antimicrobial uses

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1800s-1900s

- purification of plant compounds
- synthesis of compound in labs
- medicine turns away from herbs and towards technology

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1970s-now

- understanding of biochemical pathways
- genes start being cloned
- genomics comes of age
- synthetic biology begins to unravel pathways

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biosynthesis of taxol

- MEP pathway and alpha-phenylalanine both have separate pathways

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Philippines is a biodiversity hotspot

Mega Diverse- 5000+ endemic species and borders marine

Estimated 13 500 plant species, with 3 500 of them as indigenous to the region

• Mostly tropical or subtropical forests, mountainous regions

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Ethnocultural diversity

Approximately 110 major Indigenous groups in the Philippines, with around 150 languages

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Drug use policy

Former president Rodrigo Duterte

Extrajudicial killing allowed if death was resulted to drug dispersal and use

Cannabis possession: 12-20 years <300g

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What is ethnobotany

Relies on indigenously- informed plant identification, foraging, and cultivation in use as food, medicine and shelter

• Approximately 25% of drugs in conventional medication have been associated in some way with plant products

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Babaylans

Were second only in command to the datus (regional chieftains) during pre-colonial times

• Role came through spiritual possession, had a spirit familiar

• Functioned as warriors, healers, record keepers, priestesses, and sages

• Generally female, but transgender, male or non- binary babaylans existed

• Were ostracized post- Spanish colonization

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Albularyos

Adapted from the Spanish term herbolario

• Contemporary to Babaylans

Albularyos

• General practitioner, counsellor

• Cupping, herbal concoctions, bone alignment, etc.

• Mostly present in rural areas

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Indigenously informed traditional medicine

• Surveys constructed to quantify and record traditional knowledge of medicinal plants

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Contemporary Filipino traditional medicine

interest in traditional medicine has persisted for several reasons

– Local knowledge

– Availability of resources

– Anecdotal evidence

– Distrust of modern healthcare

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Philippines income inequality

As there is no universal healthcare in the Philippines, a single trip to the doctor can cost between P500-1500

Health care not accessible

1 traditional, complementary, or alternative medicine (TCAM) health practitioner for every 300 Filipinos

• 1 doctor to >26, 000 Filipinos

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Medication in the Philippines is not financially accessible

Over 80% of commonly prescribed medications cost more than a single day’s income of the lowest paid government worker

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The widespread use of traditional medicines

Despite the income disparity,rural and urban communities both rely on traditional medicine

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Flora de Filipinas

A landmark botanical atlas illustrating Filipino medicinal plants in detail along with their uses

– Also included folklore insights

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Tungkod Pari: A plant of war

Ti plant, Cordyline fruticosa: roots were harvested for diarrhea treatment

– In folklore: the Ifugao tribe planted these near rice plantations to drive evil spirits away and for ritualistic use

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Duhat: A sweet treat

Java Plum, Syzygium jambolanum: leaves can be smoked as a tobacco alternative, wounds can cleaned with bark reduction

– In folklore: trees are hiding places of Engkanto (Elves), and Pugots

– Java plums were part of offerings to Mandurugos (Filipino shapeshifting vampires) so they would not harm a family

regulates blood sugar levels

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Tuli

Tuli: a male rite of passage

– Traditionally performed by a manunuli, boys around 8-12 years old undergo a dorsal slit circumcision

– Boys are told to chew bayabas (Psidium guajava, guava) leaves during the procedure, with the chewed mixture applied afterwards to stop the bleeding

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Bayabas antioxidant- leaf of guava plant

Antioxidants interact with free radicals that are produced during oxidation: these compounds are found in guava leaves

• Quercetin acts as a spasmolytic and as an antioxidant

• Rutin exhibits high free radical scavenging activity

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Bayabas as an antimicrobial

Guava leaves have polyphenols that have been shown to inhibit various microorganisms

– Tanninscanchelate extracellular iron, pass through bacterial cell walls and interfere with metabolism, disrupt cell membranes and inhibit cell wall synthesis

– Phenolshavebeenshownto interfere with ergosterol, a component of fungal cell walls

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Why Bayabas is an effective antimicrobial

Bacteria generally exist in biofilms

– Bacterial biofilms are more resistant to treatment

• Guava leaf extract has been shown to disrupt quorum sensing- dependent biofilms growth

– alpha-copaene binds CviR

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Bayabas in wound healing

Antioxidants quench free radicals incurred by damaged cells and promote angiogenesis

Triterpenes facilitate wound closing by inhibition of proinflammatory components such as interleukin-6 (IL-6) and upregulating anti- inflammatory cytokines like interleukin-10 (IL-10)

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The NIRPROMP prompt

The National Integrated Research Program on Medicinal Plants (NIRPROMP) was established in 1974 as a collaboration between the University of the Philippines Manila (UPM) and the Department of Science and Technology (DOST) government branch

– Goals:

• Discover new (and substitute) drugs

from plants

• Develop drugs in various dosages to establish an autonomous Filipino pharmaceutical industry

• Generate new sources of revenue via cash crops

Dr. Nelia Cortes-Maramba

Faced backlash

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NIRPROMP continued to examine the medical plants

identified for

– safety,

– efficacy,

– quality,

– availability of raw material,

– and propagation studies of the raw herbs

• After investigation into all 480 plants, 10 were chosen to focus on

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Lagundi

Selected for further investigation as respiratory illness was identified as one of the symptoms in the Filipino population that would be easiest to treat

• Identified four main bioactive components

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Initial lagundi bioactive identification

Leaf extracts identified chrysoplenol-D, casticin, luteolin, isoorientin as bioactive components

– Compounds were found to work synergistically together, and performed weakly alone

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Lagundi as an antitussive

Flavonoids:

– Chrysoplenol-D: muscle relaxant

– casticin, luteolin, isoorientin that function as anti- histamines

• Leukotrieneinhibitors • Lagundinin: a recently

discovered iridoid

– A deterrent involved with plant defense

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Lagundi as a mucolytic and bronchodilator

Flavonoids bind to polymers and fibrins to dissolve sticky mucus in the lungs

• Bronchodilation occurs via the inhibition of

phosphodiesterase and calcium channels by flavonoids and tannins

– Extracts also show mast cell stabilization and antieosinophilic activity

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Lagundi Clinical trials

1980s clinical studies ensued

– 119 participants that had a cough were screened and given either lagundi or a placebo

– Patients improved with lagundi without side effects

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The lagundi tablet

1993: NIRPROMP develops a

tablet

– Leaves are dried and processed into a tablet form

• 1995: The Department of Health releases a list of officially endorsed medicinal plants: the ten promising plant pupils

• 1996: The Bureau of Food and Drugs approves lagundi tablets for commercial production as medicinal tablets for cough, cold, and asthma

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Lagundi backlash

Healthcare professionals were hesitant to endorse lagundi despite clinical evidence

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The lagundi cough syrup

1999: developed a cough syrup through decoction of leaves

• Now the second most popular cough medication in the Philippines

• Many offshoots from different companies now

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Information Transfer Act (2009)

Technology developed with government funds must be completely transferred to establishments like universities to evolve the work into useful products and services

• The Government then formally transferred the lagundi cough syrup to UPM for future R&D, licensing and commercialization

• This act allowed the University to attain 60% of royalties from developed products (as compared to 40% before the act) and 40% for the government

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What does the pharmacy market look like

today?

Filipinos are paying

– x4 more for generic drugs and

– up to 22x more for branded products compared to international reference prices established by the World Health Organization

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Biopiracy

Biopiracy: exploitation of indigenous resources for commercialization without due acknowledgement of source materials

• The Philippines loses approximately 8.1 Million USD annually in royalties for a single pharmaceutical product derived from Philippine genetic resources that was patented by a foreign company

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Bitter gourd Ampalaya

mixture patented by New Jersey pharmaceutical company to treat diabetes

• Research into developing new drugs from plants is slow, not well funded

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Traditional and Alternative Medicine Act

10 patented herbal medications

established to encourage research on developing traditional medicine for widespread market use

– Includes standardization, advocacy, and protection of resources

– Created the Philippine Institute of Traditional and Alternative Health Care (PITAHC)

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Indigenous knowledge acquisition •

PITAHC has constructed

– Documentation of our cultural heritage on the Philippine Traditional Medicine (PTM)

– Encyclopedia of Medicinal Plants

– Philippine Herbal Pharmacopoeia Book

– NationwideProfilingSurveyof Traditional and Alternative Health Care Practitioners (TAHC) in the Philippines

– Conferences/workshops to disseminate information

• Caveat: most of these texts don’t seem to be publicly accessible (yet)

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Access and benefit sharing (ABS)

Founded in 2021

– Focused on gaining prior informed consent (PIC) from parties and establishing mutually agreed terms (MATs) to ensure equitable access and benefit to genetic resources and their benefits

• First instance in 2023 between Herbanext Laboratories, the Ayta people, and banaba (Lagerstroemia speciosa) for diabetes

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61

Sir William Osler

- father of modern medicine
- co-founder of John Hopkins Hospital
- instituted the residence program in hospitals

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opium poppy (Papaver somniferum)

- produces morphine along with many other alkaloids (codeine, thebaine, oripavine)
- annual, 120 day growth cycle
- grow in temperate, warm climates in a variety of soils

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opium poppy - medicinal history

Spain 4200 BC - poppy pots
Egypt 1500 BC - Ebers Papyrus
Crete 1300 BC - poppy goddess
Europe 1483 - Canon of Medicine
late 1800s - opium medicines
early 1900s - heroin cough syrup

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opium poppy - production

- licit and illicit production globally
- licit in Europe, India, Australia
- illicit in Central America and Southeast Asia

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opiate requirements

- 84% of morphine is converted to codeine to meet social demands

alkaloid

<p>- 84% of morphine is converted to codeine to meet social demands</p><p>alkaloid</p>
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opiate shortages

- many countries are underestiamiting the opiate needs or not putting forth any useful estimates
- need extensive paperwork and approval just to study the opium poppy, nevermind to grow the plant

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Tasmanian poppy industry

- largest legal producer, restricted licensing
- over 20,000 hectares, $3k per hectare
- must prevent regrowth
- warning notices on fences

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mu opioid receptor

- located in brain and cortex
- respiratory depression
- euphoria
- sedation
- physical dependence
- B-endorphin, enkephalin
- morphine, fentanyl, sufentanil

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kappa opioid receptor

- located in the brain
- analgesia
- dysphoria
- met-enkephalin, Leu-enkephalin
- deltorphin

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delta opioid receptor

- located in brain
- analgesia
- anti-depression
- dynorphin A and B
- buprenorphine

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opioid agonists

- morphine, heroin

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opioid antagonist

- naloxone, naltrexone, beta-funaltrexamine

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endogenous opioid system

- mediates many physiological effects
- pain
- respiratory control
- appetite
- thermoregulation

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Alkaloid diverse metabolites

Starts with benzylisoquinoline

Dopamine + 4-HPAA = Norcoclaurine

Decoration- O/N methylation, hydroxylation, acetylation, reductions/ oxidation

Enzyme types- Methyltransferases, cytochromes P450, NADPH reductase, FAD oxidoreductase

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heroin

- illegal opioid
- produced by adding two acetyl groups to a molecule of morphine
- 3x times as potent as morphine

-Morphine prodrug

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opium harvesting

- late afternoon
- incision is make with a knife
- latex oozes out
- dried latex is collected in the morning
- can be re-bled 3 to 10 times

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Modularity and repetition

similar gene groups work together in pathways, synteny

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morphine biosynthesis

1) tyrosine is converted to dopamine and 4-HPAA
2) dopamine and 4-HPAA are combined to form Norcoclaurine
3) 11 more steps to get codeine
4) CODM converts codeine to morphine

<p>1) tyrosine is converted to dopamine and 4-HPAA<br>2) dopamine and 4-HPAA are combined to form Norcoclaurine<br>3) 11 more steps to get codeine<br>4) CODM converts codeine to morphine</p>
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Norman poppy (top1)

- EMS mutation of commercial morphine seed
- produces thebaine and oripavine only
- reduced reliance on opium
- mutation likely occurs in DIOX1/T6ODM due to lack of production of codeine and morphine

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Comparative transcriptomics

1 gene suppressed in norman poppy

Microarray probe found the gene that was downregulated

3 genes today with Danovo

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DIOX3/CODM (3-O-demethylation)

- converts thebaine to oripavine
- converts codeine to morphine

Horizontal steps

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DIOX1/T6ODM (6-O-demethylation)

- converts thebaine to codeine
- converts oripavine to morphine

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O-Demethylation in humans

CYP2D6

Liver cytochrome P450

Detoxifies ~25% of all pharmaceuticals

Catalyze the 3-O-Demethylation of codeine to morphine

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opioid production

knowt flashcard image
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opium varieties Production system

Morphine → morphine + codeine

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Gene silencing for DIOX-a

DIOX-a silences- T6ODM, DIOX2, CODM (thebaine and morphine)

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Top1 production system

Thebaine → Oxycodone, Buprenorphine, Hydrocodone

Oripavine → Hydromorphone, Oxymorphone, Naltrexone

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Virus induced gene silencing

Synthetic combined with agrobacterium, put into leaves of poppy, silence gene of interest.

Transient technology

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Gene silencing DIOX-b

DIOX-b silences- T6ODM (high thebaine and morphine)

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Gene silencing DIOX-c

DIOX-c silences- DIOX2 (not integral to process)

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Gene silencing DIOX-d

DIOX-d silences-CODM (Have thebaine, codeine, less morphine)

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92

the dark ages

- little knowledge on cause or treatment of malaria

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Horace Walpole

- described malaria as "bad air from swamps and marshes"

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Charles Louis Alphonse Laveran

- French surgeon who noticed parasites in blood of a malaria patient

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malaria

- kills 300-500 million people each year
- spread worldwide
- correlation with swamps

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malaria - cause

- four species of protozoans

- parasite held in the mouth of Anopheles mosquito in sporozoite form

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malaria - effects

- recurring bouts of fever and chills and anemia
- cerebral malaria results in death if left untreated

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malaria - mechanism of action

- sporozoite form multiplies in liver, creating merozoites
- merozoites invade RBC and deplete hemoglobin
- RBC rupture and release merozoites
- rupture causes fever

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Cinchona officinalis bark

- contains quinine, which is used to treat malaria

First species to be described

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Pelletier and Caventou

- isolated alkaloid quinine

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