Originality fromThe Innovation Development Fund

Technical Supervision byPostgraduate Education and Research Program in Chemistry

TECHNICAL INFORMATION

Prepared bySombat WanauppathamkulThe Innovation Development Fund &International Laboratories Corp., Ltd.

www.plaitanoids.comISBN 974-229-502-6

1

Contents

Introduction ........................................................................................................................................................................................................ 3

Product Description .................................................................................................................................................................................. 4

Production Specification .................................................................................................................................................................... 5

Product Availability ................................................................................................................................................................................... 5

Pure Compounds Isolated from Zingiber cassumunar Roxb. .............................................................. 6

Biological Activities .................................................................................................................................................................................. 7

Application ......................................................................................................................................................................................................... 9

Literature Review:

Ethnopharmacological Use ...................................................................................................................................10

Description of the Plant ............................................................................................................................................... 12

Chemical Constituents and Biological Activities ......................................................................... 14

Chemical Constituent Comparison of Plai Rhizomes ............................................................. 21

Safety ...................................................................................................................................................................................................................... 23

Products .............................................................................................................................................................................................................. 23

Selected References ........................................................................................................................................................................... 24

Plai : Zingiber cassumunar Roxb.

2

Prepared by:

Sombat Wanauppathamkul

Project Coordinator, The Innovation Development Fund &

International Laboratories Corp., Ltd.

Originality:

The Innovation Development Fund

National Science and Technology Development Agency

Ministry of Science and Technology

Scientific Advisor:

Postgraduate Education and Research Program in Chemistry:

Chiang Mai University

Kasetsart University

Khon Kaen University

Mahidol University

Songkla University

Copyright:The Innovation Development FundFirst edition 2003

All rights reserved. No part of this

publication may be reproduced, stored

in a retrieval system or transmitted, in

any form or by any means, electronics,

mechanical, photocopying, recording or

otherwise, without written permission

of the copyright holders.

I S B N 9 7 4 - 2 2 9 - 5 0 2 - 6

3

Zingiber cassumunar Roxb.,

commonly known as Plai, is a Thai

herbal plant which has been

exploited for medicinal purposes in

Thailand and Southeast Asia for

centuries. Plai has long been

regarded by Thai massage therapists

as one of those oils necessary to have

in their kit to combat joint and muscle

problems. The plant has been

proven to be extremely useful for

human health and thus developed

into creams and massage oils for

relieving muscle pain. Furthermore,

it is well known that the essential oils

from Plai have also been shown to

cure acne, bruises, burnt skin, skin

inflammation, muscle pain, insect

bite, and asthmatic symptoms. They

are even proven to cope with cough

and respiratory symptoms as well.

Plai extracts exhibited anti-inflamma-

tory and anti-bacterial activities. A

number of pure compounds isolated

from the plants has been shown to

possess anti-microbial, topical and

oral anti-inflammatory, analgesic,

smooth muscle relaxant, anti-tyrosinase

and anti-oxidative activities. These

therapeutic indications and the

reported ethnomedical uses make

Plai an attractive candidate for the

development into cosmetics, spa

and skin beautification products.

Introduction

This Strategic Innovative Plai project is a

joint effort between the Innovation

Development Fund (IDF), the Postgraduate

Education and Research Program in

Chemistry (PERCH), and leading herbal

companies, with the goal to export Plai

products to both local and global markets.

The project could help restructure the

manufacturing and branding process in

the country as well as help in the promo-

tion of Thai herbal plants to play a leading

role in global markets.

IDF and PERCH have succeeded in the

development of a new “Plai” (Zingiber

cassumunar Roxb.) through “collaborative

innovation” between herbal companies.

The project benefited from PERCH’s Plai

research which has developed the

substances having the trademark

PlaitanoidsTM that will be exported in the

forms of PlaitanoidsTM essential oil,

PlaitanoidsTM liquid extract, and

PlaitanoidsTM powder extract for make-up,

shampoo, toothpaste, and spa industries.

With enough support, Plai and selected

pure compounds could be developed for

future pharmaceutical use.

Both IDF and PERCH aim to utilize the

research to meet the market’s demands,

especially in the starting-up of new

companies on a research-based industry,

therefore leading up to innovation to

increase national competitiveness.

Plant Name: Plai

Botanical Name: Zingiber cassumunar Roxb.

Plant Native to: Thailand, Indonesia, India

Parts Used: Rhizome

Traditional Thai Massage Usage: Muscle relaxant, joint pains, anti-acne

4

Steam Distillation Process

Cleaning of the two-year-old rhizomes of Plai

Thinly slice the rhizomes (about 1-2 mm)

Put into tray

Heat at the temperature of 80°C for 6 hours

PlaitanoidsTM - Essential Oil

Extraction and Spray Dry Process

Steam distilled Plai

Separate the waste from the liquid

PlaitanoidsTM - Liquid Extract

Evaporate at controlled temp./pressure

Spray dry at controlled temp.

PlaitanoidsTM - Powder Extract

95% Alcohol 4 days

Add additive

PlaitanoidsTM is the trademark of

ingredients containing groups of

compounds consisting of

arylbutanoids (e.g. DMPBD) and their

dimers, curcuminoids and essential

oils (e.g. terpinen-4-ol) derived from

the rhizomes of Zingiber cassumunar

Roxb. with collaborative innovation

from IDF, PERCH and leading compa-

nies based on the development of

new products and technologies.

Terpinen-4-ol and sabinene are

monoterpenes. They are major

constituents in essential oil from

Zingiber cassumunar Roxb. The

essential oil has been shown to exhibit

topical anti-inflammatory and anti-

microbial effects. DMPBD stands for

(E)-1-(3', 4'-dimethoxyphenyl)butadiene

found in essential oil and shown

strong anti-inflammatory effect.

According to the pharmacological

studies, Plai extracts have been

proven to have anti-inflammatory

and anti-bacterial effects.

Product Description

Essential Oil

PlaitanoidsTM

Powder Extract

Liquid Extract H3CO

OCH3

(E)-1-(3',4'-Dimethoxyphenyl)butadiene = DMPBD(3)

OH

CH3 CH3

CH3

Terpinen-4-ol(1)

5

Product Availability

Product Specification

PlaitanoidsTM

Plant: Zingiber cassumunar Roxb.

Thai Name: Plai

Plant Part Used: Rhizome

Active Ingredients: Essential oils (e.g. terpinen-4-ol, sabinene)

Arylbutanoids (e.g. DMPBD) and their dimers

Curcuminoids

Preservative: None

Microbial Count: <1,000 CFU/g

Storage: Store in a well closed container at cool dry place (<25°C)

PlaitanoidsTM is the trademark of ingredients containing a group of compounds

consisting of arylbutanoids (e.g. DPMBD) and/or essential oils (e.g. terpinen-4-ol)

derived from the rhizomes of Zingiber cassumunar Roxb. with collaborative

innovation from IDF, PERCH and leading companies based on the development of

new products and technologies.

1. PlaitanoidsTM Essential Oil2. PlaitanoidsTM Liquid Extract3. PlaitanoidsTM Powder Extract

6

Pure Compounds Isolated from Zingiber cassumunar Roxb.

(1) (2) (3) (4)

(5) (6) (7)

(8) (10)

(12)

(13) (14)

(15) (16)

CH3

CH3 CH3

OH

H3CO

H3CO

H3CO

H3COH3CO

H3CO

OH

H3CO

H3CO

H3CO

H3CO

H

H

H

H

H

H

H

H3CO

H

H

H3CO

OH

O OH

OH

O O

OH

H3CO

HO

H3CO

OH

O OH

OH

H3CO

OH

O OH

OH

H3CO

HO

O O

OH

H3CO

H3CO

OH

O OH

OH

H3CO

OH

O OH

OH

H3CO

OAc

OCH3OCH3OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

OCH3

(9)

(11)

7

The biological activities of Plai components can be summarized as follows:

Analgesic Activity

• (E)-1-(3',4'-Dimethoxyphenyl)but-1-ene (9)

Anti-inflammatory Activity

• Terpinen-4-ol (1)

• α-Pinene (2)

• (E)-1-(3',4'-Dimethoxyphenyl)butadiene - DMPBD (3)

• (E)-4-(3',4'-Dimethoxyphenyl)but-3-enyl acetate (4)

• cis-3-(3',4'-Dimethoxyphenyl)-4-[(E)-3"',4"'-dimethoxystyryl]cyclohex-1-ene (5)

• cis-3-(3',4'-Dimethoxyphenyl)-4-[(E)-2"',4"',5"'-trimethoxystyryl]cyclohex-1-ene (6)

• cis-3-(2',4',5’-Trimethoxyphenyl)-4-[(E)- 2"',4"',5"'-trimethoxystyryl]cyclohex-1-ene (7)

• (E)-4-(3',4'-Dimethoxyphenyl)but-3-en-1-ol (8)

• (E)-1-(3',4'-Dimethoxyphenyl)but-1-ene (9)

• Curcumin (10)

• Cassumunin A (11)

• Cassumunin B (12)

• Cassumunin C (13)

Anti-oxidative Activity

• Curcumin (10)

• Cassumunin A (11)

• Cassumunin B (12)

• Cassumunin C (13)

• Cassumunarin A (14)

• Cassumunarin B (15)

• Cassumunarin C (16)

Smooth Muscle Relaxant, Uterine Relaxant and Anti-histamine Activities

• (E)-4-(3',4'-Dimethoxyphenyl)but-3-en-1-ol (8)

Biological Activities

8

Table 1 ID50 for anti-inflammatory activity (model of 12-O-tetradecanoylphorbol-13-acetate-induced ear edema

in rats).

Sample ID50 (µg/ear)

Hexane extract 854

(E)-4-(3',4'-Dimethoxyphenyl)but-3-enyl acetate (4) 62

cis-3-(3',4'-Dimethoxyphenyl)-4-[(E)-3"',4"'-dimethoxystyryl]cyclohex-1-ene (5) 21

cis-3-(3',4'-Dimethoxyphenyl)-4-[(E)-2"',4"',5"'-trimethoxystyryl]cyclohex-1-ene (6) 20

cis-3-(2',4',5'-Trimethoxyphenyl)-4-[(E)- 2"',4"',5"'-trimethoxystyryl]cyclohex-1-ene (7) 2

(E)-4-(3',4'-Dimethoxyphenyl)but-3-en-1-ol (8) 47

Diclofenac 61

The rhizome of Zingiber cassumunar

Roxb. is widely used in Thai traditional

medicine for topical treatment of

sprains, contusions, joint inflamma-

tions, muscular pain, abscesses and

similar inflammation-related disorders.

The topical anti-inflammatory activity

of the five major components of the

essential oil demonstrated that (E)-1-

(3’,4’-dimethoxyphenyl)butadiene

(DMPBD, 3), terpinen-4-ol (1) and α-

pinene significantly inhibited edema

formation, whereas sabinene and γ-

terpinene were inactive up to 6 mg/

paw. The most active compound,

DMPBD, was found to be an anti-

inflammatory agent twice as potent

as the reference drug diclofenac

(ID50 = 3 vs 6 mg/paw, respectively).

Interestingly, the five compounds

isolated from hexane extract of the

rhizome were all found to be equally

or more potent anti-inflammatory

agents than the reference drug

diclofenac as shown in Table 1

whereas the potency of the

hexamethoxylated compound 7 was

ca 20-30 times higher than that of

diclofenac.

9

Application

Cosmetics

Spa product (e.g. massage oil, aromatherapy)

Shampoo and conditioner products

Toothpaste product

Anti-acne product

Anti-aging or anti-wrinkle product

Skin whitening product

Mosquito repellant product

Over-the-Counter Pharmaceutical

Analgesic and anti-inflamatory products

Safety

No side effect has been recorded when using Plai.

10

Literature Review: Ethnopharmacological Use31

Plai has long been regarded by Thai

massage therapists as one of those

oils necessary to have in their kit to

combat joint and muscle problems.

Plai is in the same family as ginger but

has different properties and more

intense actions. The fresh rhizome of

Plai is used in traditional Thai massage

for muscle relaxant and joint pains.

General Description:Essential oil of Plai is steam distilled

from the rhizome and has a pale

amber color. The scent is a cool,

green peppery one with a touch of a

bite. Active chemicals: sabinene (25-

45%), γ-terpinene (5-10%), α-terpinene

(2-5%), terpinen-4-ol (25-45%), and

(E)-1-(3’,4’-dimethoxyphenyl)butadiene

- in text as DMPBD (1-10%).

Actions:Analgesic, anti-neuralgic, anti-inflam-

matory, anti-septic, anti-spasmodic,

anti-toxic, anti-viral, carminative,

digestive, diuretic, febrifuge, laxative,

rubefacient, stimulant, stomachic,

tonic, vermifuge.

Applications:Aches and pains, inflammations, joint

problems, muscle spasms, sprains and

strains, torn muscles and ligaments

asthma, catarrh, chronic colds, colic,

constipation, diarrhea, fevers, flatu-

lence, heartburn, immune problems,

influenza, nausea, respiratory problems.

A) Analgesic, anti-neuralgic, anti-inflammatory, sprains and strains, tornmuscles and ligaments: On inflamed

joints, applying Plai, straight on; has

been found to ease off the pain for

upwards of 18 hours, which is incred-

ible since no other oil has been found

to change pain levels so far. On joints

that were inflamed due to injury, Plai

was best combined with oils such as

black pepper and lemon or neroli,

Himalayan cedar and orange. These

combinations worked to take the

swelling down, calm the pain and

speed up the healing time consider-

ably. Dilutions were one bottle of 10%

concentration in a vegetable gel and

a small roller bottle with no dilution -

blends were all oils equal parts. The

analgesic topical preparation has

also been formulated and distributed

by the General Pharmaceutical

Organization (GPO).

11

B) Post Operative Care: Plai, nutmeg

and lemon have been used as a post

operative surgical blend on a knee

surgery. These were of equal amounts

in a 10% concentration in a roller

bottle and applied above and below

the surgical area. Tissue inflammation

and swelling was significantly lower

than in an area that had had the

same surgery without the use of the

Plai. With the Plai blend, no normal

narcotics were needed to control the

post surgical pain.

C) Anti-histaminic: Plai, while being

of the ginger family, does not possess

the classic heat that is common to

the rhizomes. It has a cooling action

on inflamed areas, be them joints

and muscles or kidneys and lungs.

Clients have found that using Plai for

asthma along with tarragon (or

rosemary) and cypress causes the

attacks to greatly diminish in intensity.

D) Irritable Bowel Syndrome: For

digestive upsets, Plai along with black

pepper, orange and tarragon has

been used to counter irritable bowel

syndrome. This blend was applied

over the abdomen after each bowel

movement or anytime there were

any cramping or pain in the abdomi-

nal area. Within three applications, all

problems calmed down.

E) Menstrual Cramps: Can be

alleviated from a blend with Linden

Blossom, Plai, Marjoram and Orange.

This was applied across the lower

back and front abdomen every 15

minutes until pain subsided. It was

found that after three applications all

cramps ceased and blood clots

diminished.

F) Other Benefits: Dr Daniel Penoel

and Pierre Francome, Ph.D. in

“L’aromatherapie Exactement”:

Zingiber cassumunar Roxb. is anti-

inflammatory, carminative, anti-pyretic,

and a bronchodilator. They suggest

that it could be useful for asthma,

digestive problems, dysmenorrhoea,

and inflammation of the colon.

12

1

2

3

Literature Review: Description of the Plant25

The rhizome part of the herb has a

yellow to green color with fleshy thick

texture containing multiple sessile

tubers. Leaf stems 1 to 1.5 m tall.

Leaves distichous, oblong-lanceolate,

20 to 30 cm long and 2 to 8 cm wide,

pubescent below; ligule very short,

bilobed, pubescent; sheath glabrous

or hairy. Inflorescences scapose;

peduncle 8 to 30 cm long, with

pubescent sheaths. Spike ovoid-

ellipsoid; bracts greenish red, narrowly

obovate or rhomboid, 2.5 to 3.5 cm

long; bracteole shorter than bract,

ovate, 3-dentate. Calyx truncate,

glabrous. Corolla tube ca. 2.5 cm

long, pale yellow, dorsal lobe

cymbiform, lateral lobe linear-

lanceolate. Labellum pale yellow,

suborbicular, apex emarginate,

lateral lobe ovate-oblong, append-

age slightly longer than anther;

stamen pale yellow. Ovary inferior,

3-celled. Fruit, small, globose capsule

ca. 0.5-1 cm (Fig. 1).

Description: Odor, pleasant aromatic;

taste, pungent. The odor is reported

as strong and reminiscent of a

mixture of ginger, camphor and

turmeric, the taste as hot and

camphoraceous.

Identification:

A) To 500 mg of the sample, in

powder, add 5 ml of chloroform, set

aside for 5 minutes and filter (solution

A). Examine 1 ml of solution A under

ultraviolet light (366 nm): a greenish

yellow fluorescence is observed.

B) To 1 ml of solution A, add 0.2 ml of

acetic anhydride-sulfuric acid TS: a reddish

brown color is produced.

C) To 1 ml of solution A, add 1 ml of boric

acid-methanol TS: an orange color is

produced.

D) Carry out the test as described in the

“Thin-layer Chromatography”, using silica

gel GF254 as the coating substance and a

mixture of 70 volumes of hexane 30

volumes of ethyl acetate as the mobile

phase but allowing the solvent front to

ascend 15 cm above the line of applica-

tion. Apply separately to the plate, 2 µl of

solution A and 3 µl of solution B. Prepare

solution A by extracting 2.5 g of the

sample, in powder, with hexane until

complete extraction is effected. Evapo-

rate the hexane extract to dryness and

dissolve the residue in 5 ml of chloroform.

Fig. 1 Zingiber cassumunar Roxb.

1. whole plant

2. rhizome

3. inflorescence

13

Table 2. hRf values of components in hexane extract of the Rhizome of Zingiber cassumunar Roxb.

Spot* hRf ValueDetection with

UV254 Anisaldehyde- Vanillin-Sufuric acidSulfuric acid TS (Color) TS (color)

1 10-13 - red red-brown

2 14-16 quenching brown olive-green

3 16-19 quenching carmine-red dark pink

4 20-22 - violet violet

5 24-28 quenching olive-green purple

6 31-35 quenching wine-red blue-violet

7 42-45 quenching violet red

8 49-52 quenching dark pink light orange

9 58-61 quenching blue-violet violet

10 62-64 - blue-violet pink

11 68-72 quenching dark blue-violet blue-purple

12 73-76 quenching light orange dark blue

13 84-88 - brown-red light brown

*1 = curcumin (15)2 = 2-Methoxy-8-(3',4'-dimethoxyphenyl)-1,4-napthaquinone (29)3 = [(E)-4-(3',4'-dimethoxyphenyl)]but-3-en-1-ol (8)5 = cis-3-(2',4',5'-trimethoxyphenyl)-4-[(E)-2"',4"',5"'-trimethoxystyryl]cyclohex-1-ene (7)6 = cis-3-(3' ,4'-dimethoxyphenyl)-4-[(E)-2"',4"',5"'-trimethoxystyryl]cyclohex-1-ene (6)7 = cis-3-(3',4'-dimethoxyphenyl)-4-[(E)-3"',4"'-dimethoxystyryl]cyclohex-1-ene (5)8 = (E)-4-(3',4'-dimethoxyphenyl)but-3-enyl acetate (4)4, 9-13 = unknown

For solution B dissolve 1 mg of

curcumin in 1 ml of chloroform.

After removal of the plate from the

chromatographic chamber, allow it

to dry in air and examine under

ultraviolet light (254 nm), marking the

quenching spots. The spots obtained

with solution A correspond in hRf

values to the spot number 2, 3, 5, 6, 7,

and 8. Several spots of higher hRf

values are also observed (Table 2).

Spray the plate with anisaldehyde-

sulfuric acid TS and heat at 110°C for

10 to 15 minutes; spots due to those

of numbers 2, 3, 5, 6, 7, and 8 in Table

2 are brown, carmine-red, olive

green, wine-red, violet, and dark

pink, respectively. Red spot due to

curcumin (hRf value 10 to 13) and

other spots of different colors are

observed (Table 2).

Repeat the same procedure on

another plate but spray with vanillin-

sulfuric acid TS and heat at 110C for

10 to 15 minutes; the spots due to

those of number 2, 3, 5, 6, 7, and 8

are olive-green, dark pink, purple,

blue-violet, red, and light orange,

respectively. Red-brown spot due to

curcumin and other spots of different

colors are observed (Table 2).

14

Arylbutanoids

IItem Structure Biological Activity Ref.

Literature Review:

Chemical Constituents and Biological Activities

1

2

1

2

3

Anti-inflammatory,

Anti-microbial

Anti-microbial

Anti-inflammatory

Anti-inflammatory,

Analgesic

Uterine relaxant,

Anti-inflammatory,

Smooth muscle

relaxant,

Anti-histamine

11, 20, 26

1, 20, 26

11, 12,

19, 20,

26, 31

11, 12,

19, 20

7, 10, 11,

16, 20,

24, 27

Essential oil of Plai is steam distilled from the rhizome and has a pale amber color.

The scent is a cool, green peppery one with a touch of a bite. Active chemicals in

Plai are sabinene (27-34%), γ-terpinene (6-8%), α-terpinene (4-5%), terpinen-4-ol

(30-35%), and (E)-1-(3’,4’-dimethoxyphenyl) butadiene (12-19%).

Some Chemical Constituents from Zingiber cassumunar Roxb.

Monoterpenes

Item Structure Biological Activity Ref.

CH3

CH3 CH3

OH

CH3 CH3

Terpinen-4-ol (1)

Sabinene (17)

(E)-1-(3',4'-Dimethoxyphenyl)butadiene

= DMPBD (3)

(E)-1-(3',4'-Dimethoxyphenyl)but-1-ene (9)

(E)-4-(3',4'-Dimethoxyphenyl)but-3-en-1-ol

(8)

H3CO

H3CO

H3CO

H3CO

H3CO

H3CO

OH

15

Arylbutanoids

Item Structure Biological Activity Ref.

7, 10, 20,

24, 27

11,12

24

24

24

20

Anti-inflammatory

-

-

-

-

-

4

5

6

7

8

9

(E)-4-(3',4'-Dimethoxyphenyl)but-3-enyl

acetate (4)

(E)-4-(3',4'-Dimethoxyphenyl)but-3-enyl

palmitate (18)

(E)-3-Hydroxy-1-(3',4'-dimethoxyphenyl)but-

1-ene (19)

(E)-2-Hydroxy-4-(3',4'-dimethoxyphenyl)but-

3-en-1-ol (20)

(E)-2-Methoxy-4-(3',4'-dimethoxyphenyl)but-

3-en-1-ol (21)

1-(3',4'-Dimethoxyphenyl)butane (22)

H3CO

H3CO

OAc

H3CO

H3CO O-Pal

H3CO

OH

H3CO

H3CO

H3CO

OH

OH

H3CO

H3CO

OH

OCH3

H3CO

H3CO

16

Cyclobutyl Derivative

Item Structure Biological Activity Ref.

Arylbutanoids

Item Structure Biological Activity Ref.

10

11

12

13

(E)-4-(4'-Hydroxy-3'-methoxyphenyl)but-2-

en-1-ol (23)

(E)-4-(4'-Hydroxy-3'-methoxyphenyl)but-3-

enyl acetate (24)

4-(2',4',5'-Trimethoxyphenyl)but-1,3-diene

(25)

(E)-1-(2',4',5'-Trimethoxyphenyl)but-1-ene

(26)

24

24

12

11, 12

H3CO

HO

OH

H3CO

HO

OAc

H3CO

H3CO OCH3

H3CO

H3CO

OCH3

H3CO

H3CO OCH3

OCH3

-

-

-

-

1

cis-1,2-bis[(E)-3",4"-

Dimethoxystyryl]cyclobutane (27)

- 21

17

Curcuminoid Derivatives

Item Structure Biological Activity Ref.

Curcumin (10)

Cassumunin A (11)

Cassumunin B (12)

Cassumunin C (13)

Cassumunarin A (14)

Cassumunarin B (15)

Anti-inflammatory,

Anti-oxidative,

Anti-tyrosinase,

Anti-microbial

Anti-oxidative,

Anti-inflammatory

Anti-oxidative,

Anti-inflammatory

Anti-oxidative,

Anti-inflammatory

Anti-oxidative

Anti-oxidative

2

22

22

22

23

23

1

2

3

4

5

6

H3CO HO

O OCH3

OH

OCH3 OCH3 OCH3

H3CO HO

O OCH3

OH

OCH3 OCH3OCH3

OCH3

HO

O O

OH

OCH3

OCH3

OCH3

H3CO

H3CO

OH

O OH

OH

OCH3

OCH3

OCH3

OH

OH

OH

OCH3

OCH3

O

OCH3

H3CO

OH

O O

H3CO

HO

OCH3

18

Curcuminoid Derivatives

Item Structure Biological Activity Ref.

Naphthoquinones

Item Structure Biological Activity Ref.

Cassumunarin C (16)

2-Methoxy-8-(3',4'-dimethoxyphenyl)-1,4-

naphthoquinone (28)

2-Methoxy-8-(2',4',5'-trimethoxyphenyl)-1,4-

naphthoquinone (29)

7

1

2

Anti-oxidative

-

-

23

7, 9, 11

9, 11

O

O

OCH3

OCH3

OCH3

O

O

OCH3

OCH3

OCH3

H3CO

OH

OHO

OH

OCH3

OCH3

OCH3

H3CO

H3CO

19

Cyclohexane Derivatives

Item Structure Biological Activity Ref.

trans-3-(2',4',5'-Trimethoxyphenyl)-4-

[(E)-3"',4"'-dimethoxystyryl]cyclohex-1-ene (30)

cis-3-(2',4',5'-Trimethoxyphenyl)-4-[(E)-3"',4"'-

dimethoxystyryl]cyclohex-1-ene (31)

trans-3-(3',4'-Dimethoxyphenyl]-4-(E)-

3"',4"'-dimethoxystyryl)cyclohex-1-ene (32)

trans-3-(3',4'-Dimethoxyphenyl)-4-(E)-

2"',4"',5"'-trimethoxystyryl]cyclohex-1-ene (33)

1

2

3

4

-

-

-

-

21

11

11, 21

11

H3CO

OCH3

OCH3

OCH3

OCH3

H

H

H3CO

OCH3

OCH3

OCH3

OCH3

H

H

OCH3

OCH3

OCH3

OCH3

H

H

H3CO OCH3

OCH3

OCH3

OCH3

H

H

20

Cyclohexane Derivatives

Item Structure Biological Activity Ref.

5

6

7

7, 10,

11, 27

7, 11,

12, 27

7, 11,

12, 21, 27

Anti-inflammatory

Anti-inflammatory

Anti-inflammatory

cis-3-(2',4',5'-Trimethoxyphenyl)-4-[(E)-

2"',4"',5"'-trimethoxystyryl]cyclohex-1-ene (7)

cis-3-(3',4'-Dimethoxyphenyl)-4-[(E)-

3"',4"'-dimethoxystyryl]cyclohex-1-ene (5)

cis-3-(3',4'-Dimethoxyphenyl)-4-[(E)-

2"',4"',5"'-trimethoxystyryl]cyclohex-1-ene (6)

H

H

H3CO

H3CO OCH3

OCH3

OCH3

OCH3

H

H

OCH3

OCH3

OCH3

OCH3

H3CO

H

H

OCH3

OCH3

OCH3

OCH3

21

A major part of the oil consists of

monoterpenes with sabinene and

terpinen-4-ol as main constituents.

Sesquiterpenes accounted for a

small part of the oil with

sesquiphellandrene being the

principal constituent. In addition to

these terpenes, the oil contains a

number of phenylbutanoids. The

essential oil obtained by

hydrodistillation contained about 25%

of these phenylbutanoids whereas

the oil obtained by extraction with

Literature Review:

Chemical Constituent Comparison of Plai Rhizomes20,26,32

sab

ine

ne

terp

ine

n-4-

ol

CH3 CH3

OH

CH3 CH3

CH3

Fig. 2 GC chromatogram of essential oil of the rhizome of Zingiber cassumunar Roxb.

1 = sabinene 2 = ααααα-terpinene

3 = γγγγγ-terpinene 4 = terpinen-4-ol

5 = DMPBD

Compound A B C

Sabinene 10.1 44 34.7

Terpinen-4-ol 10.2 24 32.3

γ-Terpinene 3.6 9 6.7

α-Terpinene 2.0 6 3.7

DMPBD 9.8 6 7.2

Table 3 Essential oil composition(%) of the different source rhizomes of Zingiber cassumunar

Roxb. (A) : Indonesia20; (B) : Thailand-Prachinburi;26 (C) : Thailand - TISTR32

light petroleum and about 46%, with

trans-1-(3’,4’-dimethoxyphenyl)but-1-

ene, trans-1-(3’,4’-dimethoxyphenyl)

butadiene and trans-4-(3’,4’-

dimethoxyphenyl)but-3-enyl acetate

as the main constituents. The major

constituents in essential oil of Rhizome

of Z. cassumunar are shown in Table 3.

It is indicated that the quantities of

sabinene and terpinen-4-ol derived

from Thailand’s rhizome are more

than that of derived from Indonesia.

22

Dermal SafetyIn view of wide spread use of the

plant itself and products in the

market derived from the oil for anti-

inflammatory, analgesic and anti-

microbial activities together with

there is no report of the adverse

effect for the external usage, This

makes Plai an attractive candidate

for the developing various externally

useful products particularly essential

oil and cosmetics. However a

comprehensive safety testing

program is ongoing.

Oral SafetyAcute toxicity test of Plai revealed no

evidence of toxicity in mice when

given 10 g/kg body weight. The LD50

of 50% alcohol extract administered

per os or subcutaneous was more

than 20 g/kg and intraperitoneal was

14.8 g/kg.

Safety 33

Chronic toxicity test during 12 months

in 192 Wistar rats showed that Plai

forced fed 3.0 g/kg/day male rats

consumed less food than the control

by 12% therefore less body weight

gained. Hematological examination

also suggested all groups were

normal. Biochemical examination

indicated lower albumin but higher

SGOT and SGPT levels (p<0.05). There

was a positive correlation between

Plai’s concentration to the weight of

liver and spleen. No pathological

changes in other organs were

observed except in the liver of Plai

treated rats with evidence of hepatic

cirrhosis and hepatocarcinogenesis.

The detailed toxicological studies

including acute, subacute and

mutagenic studies will be initiated

with the DMPBD, a new pharmaco-

logical agent for the treatment of

inflammatory disorders.

Products

23

1. Casey TE et al. (1971) Essential Oil of “Phlai”, Zingiber cassumunar, Roxb.,

from Thailand. Trop Sc 13(3), 199-202.

2. Dechatiwongse T and Yoshihira K (1973) Chemical Studies on the Rhizome of

Plai (Zingiber cassumunar Roxb.). Bull Dept Med Sci 15(4), 1-15.

3. Anantasanta W and Asayakun S (1975) Study on Activities of Plai Juice for

Local Anaesthetic Effects. Chiang Mai Med Bull 14(3), 249-57. (in Thai)

4. Dechatiwongse T (1976) Isolation of Constituents from the Rhizome of Plai

(Zingiber cassumunar Roxb.). Bull Dept Med Sci 18(3), 75-9.

5. Dechatiwongse T (1979) Preparation of Plai Ointment (Zingiber cassumunar

Roxb.) as a Mosquito Repellant. Bull. Dept. Med. Sci. 21(3), 187-92.

6. Kiatyingungsulee N et al. (1979) Some Pharmacological Studies of Active

Constituent in Plai (Zingiber cassumunar Roxb.). Bull. Dept. Med. Sci. 21(1),

13-25.

7. Amatayakul T et al. (1979) Chemistry and Crystal Structures of Some

Constituents of Zingiber cassumunar Aust J Chem 32, 71-88.

8. Ngearndee P et al. (1980) The Studies of Botanical and Pharmacognostical

Structures on “Plai” (Zingiber cassumunar Roxb.). Bull Dept Med Sci 22(1),

187-92.

9. Dinter H and Hansel R (1980) The Structures of Cassumunaquinones 1 and 2

from Zingiber cassumunar. Z Naturforsch 35c, 154-5.

10. Tuntiwachwuttikul P et al. (1980) Syntheses of Some Constituents of Zingiber

cassumunar. Aust J Chem 33, 913-6.

11. Kuroyanagi M et al. (1980) Further Characterization of the Constituents of a

Thai Medicinal Plant, Zingiber cassumunar Roxb. Chem Pharm Bull 28(10),

2948-59.

12. Tuntiwachwuttikul P et al. (1981) Phenylbutanoids from Zingiber cassumunar.

Phytochemistry 20(5), 1164-5.

13. Rukachaisirikul N et al. (1983) Insecticides from Zingiber cassumunar Roxb.

Songklanakarin J Sci Technol 5(4), 353-8.

14. Tuchinda M et al. (1984) Study of Plai (Zingiber cassumunar Roxb.) in Asth-

matic Children. Siriraj Hosp Gaz 36(1), 1-5.

15. Yongchaiyud P et al. (1985) Efficacy and Tolerance of Zingiber cassumunar

Roxb. in Bronchial Asthma. Siriraj Hosp Gaz 37(6), 435-40.

16. Kanjanapothi D et al. (1987) A Uterine Relaxant Compound from Zingiber

cassumunar. Planta Med 53(4), 329-32.

17. Pongsakorn S et al. (1988) Pharmacokinetic Studies of Compound B Isolated

from Plai (Zingiber cassumunar Roxb.) in Rat. Vajira Medical Journal 32(3),

101-4.

18. Leksawasdi P and Wongwiggarn R (1990) Using Plai and Turmeric Extracts

and the Parasite, Braconids, in the Control of Soybean Leaf Roller,

Lamprosema diemenalis Guenee. J. Sci. Fac. CMU 17, 11-6.

19. Ozaki Y, Kawahara N and Harada M (1991) Anti-inflammatory Effect of

Zingiber cassumunar Roxb. and Its Active Principles. Chem Pharm Bull 39(9),

2353-6.

Selected References

24

20. Taroeno, Brophy JJ and Zwaving JH (1991) Analysis of the Essential Oil of

Zingiber cassumunar Roxb. from Indonesia. Flavour and Fragrance Journal 6,

161-3.

21. Jitoe A, Masuda T and Nakatai N (1993) Phenylbutanoid Dimers from

The Rhizomes of Zingiber cassumunar. Phytochemistry 32(2), 357-63.

22. Masuda T, Jitoe A and Nakatani N (1993) Structures of Cassumunin A, B, and

C, New Potent Antioxidants from Zingiber cassumunar. Chemistry Lett 189-92.

23. Jitoe A, Masuda T and Mabry TJ (1994) Novel Antioxidants, Cassumunarin A,

B, and C, from Zingiber cassumunar. Tetrahedron Lett 35(7), 981-4.

24. Masuda T and Jitoe A (1995) Phenylbutenoid Monomers from The Rhizomes

of Zingiber cassumunar. Phytochemistry 39(2), 459-61.

25. Ministry of Public Health. Department of Medical Sciences Vol. 1. (1995) Thai

Herbal Pharmacopoeia pp 51-6.

26. Pongprayoon U et al. (1996/97) Topical Anti-inflammatory Activity of The

Major Lipophilic Constituents of The Rhizome of Zingiber cassumunar Part I:

The Essential Oil. Phytomedicine 3(4), 319-22.

27. Pongprayoon U et al. (1996/97) Topical Anti-inflammatory Activity of The

Major Lipophilic Constituents of The Rhizome of Zingiber cassumunar Part II:

Hexane Extractives. Phytomedicine 3(4), 323-6.

28. Giwanon R et al. (2000) Antimicrobial Activity of Terpinen-4-ol and Sabinene.

Thai J. Pharma. Sci. 24S, 27.

29. Reutrakul V (2002) Medicinal Value of Some Zingiberaceous Plants. The

Journal of the Royal Institute of Thailand 27(4), 1165-72.

30. Research on Thai Aromatic Plants for Establishment of Essential Oil Database

(2003), Thailand Institute of Scientific and Technological Research (TISTR),

Bangkok, Thailand.

31. Jeenapomgsa R et al. (2003) Anti-inflammatory Activity of (E)-1-(3,4-

dimethoxyphenyl)butadiene from Zingiber cassumunar Roxb. J Ethnopharm

87, 143-8.

32. www.essentialoils.org/plai.htm33. Research Report from Department of Medical Science, Ministry of Public

Health. (in Thai)

- Koysukho R et al. (1987) Pharmacokinetic Studies of Plai (Zingiber

cassumunar Roxb.) in Animals.

- Sittisomwongse N et al. (1987) Dosage Form and Quality Control of Plai

- Sittisomwongse N et al. (1990) Study on Toxicity of Plai.

- Koysukho R et al.(1990) Study on Mutagunicity Effects of Plai Extracts and

Plai Pure Compounds.

- Dechatiwongse T et al. (1990) Analysis to Set up the Standard Control of

Plai Rhizome (Zingiber cassumunar Roxb., Rhizome).

- Koysukho R et al. (1990) Studies of Active Ingredients from Plai (Zingiber

cassumunar Roxb.) for Treatment of Asthma.

34. Informal Contact from the Medicinal Plant Information Center, Faculty of

Pharmacy, Mahidol University, Bangkok, Thailand.

The Innovation Development Fund 111 Thailand Science Park, Paholyothin Road

Klong 1, Klong Luang, Pathumthani 12120, Thailand Tel. +66-2-564 7000 ext.1451-1456

Fax +66-2-564 7000 ext.1460 E-mail: info@idf.or.th