TECHNICAL INFOR MA T ION

Originality from
The Innovation Development Fund

Prepared by
Technical Supervision by Sombat Wanauppathamkul
Postgraduate Education and The Innovation Development Fund &
Research Program in Chemistry International Laboratories Corp., Ltd.

ISBN 974-229-502-6 www.plaitanoids.com

Contents

Plai : Zingiber cassumunar Roxb.

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

1
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 Fund
First 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.

ISBN 974-229-502-6

2
Introduction
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
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.
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.
3
Product Description
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.
PlaitanoidsTM
Essential Oil
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
4
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- CH3
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 OH
studies, Plai extracts have been
proven to have anti-inflammatory
CH3 CH3
and anti-bacterial effects.
Terpinen-4-ol
(1)
Liquid Extract H3CO
OCH3
Powder Extract (E)-1-(3',4'-Dimethoxyphenyl)butadiene = DMPBD
(3)
Extraction and Spray Dry Process
Steam distilled Plai
95% Alcohol
4 days
Separate the waste from the liquid
Evaporate at controlled temp./pressure
PlaitanoidsTM - Liquid Extract
Add additive
Spray dry at controlled temp.
PlaitanoidsTM - Powder Extract
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.

Product Availability

1. PlaitanoidsTM Essential Oil

2. PlaitanoidsTM Liquid Extract
3. PlaitanoidsTM Powder Extract

5
Pure Compounds Isolated from Zingiber cassumunar Roxb.

CH3

H 3CO H3CO OAc

OH

H 3CO H3CO
CH3 CH3

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

H OCH3 H3CO OCH3 H3CO OCH3

H H H

OCH3 OCH3 OCH3

OCH3 OCH3 OCH3

H H H

H OCH3 H OCH3 H 3CO OCH3

(5) (6) (7)

O O
H 3CO OH H 3CO
H3CO OCH3

H 3CO H 3CO HO OH
(8) (9) (10)
OCH3

OH
OCH3
OH
H 3CO

OCH3
O O
O HO

H 3CO
HO OH
OCH3
OCH3 (11) OCH3 (12)

OCH3 OCH3

OH OH

OH OH

OCH3 OCH3
O HO
H3CO O HO

H 3CO
H3CO
OCH3
OCH3
(13) (14)

OCH3 OCH3

OH OH

OH OH

OCH3 OCH3

O HO H 3CO O HO

H 3CO H 3CO

OCH3 OCH3
(15) (16)

6
Biological Activities

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)

7
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.

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

8
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.

9
Literature Review: Ethnopharmacological Use 31
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.
10
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, torn
muscles 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).
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.
11
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.
12
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.
3
2
Fig. 1 Zingiber cassumunar Roxb.
1. whole plant
2. rhizome
1 3. inflorescence
 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).

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

Detection with
Spot* hRf Value
UV254 Anisaldehyde- Vanillin-Sufuric acid
Sulfuric 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

13
Literature Review:
Chemical Constituents and Biological Activities

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.
1 CH3
Anti-inflammatory, 11, 20, 26
Anti-microbial

OH

CH3 CH3

Terpinen-4-ol (1)

2 Anti-microbial 1, 20, 26

CH3 CH3

Sabinene (17)

Arylbutanoids
IItem Structure Biological Activity Ref.
1 H 3CO
Anti-inflammatory 11, 12,
19, 20,
26, 31
H 3CO

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

2 H 3CO Anti-inflammatory, 11, 12,

Analgesic 19, 20
H 3CO

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

3 H 3CO OH
Uterine relaxant, 7, 10, 11,
Anti-inflammatory, 16, 20,
Smooth muscle 24, 27
H 3CO
relaxant,
(E)-4-(3',4'-Dimethoxyphenyl)but-3-en-1-ol Anti-histamine
(8)

14
Arylbutanoids
Item Structure Biological Activity Ref.
4 H3CO OAc
Anti-inflammatory 7, 10, 20,
24, 27

H3CO

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

5 H 3CO O-Pal - 11,12

H 3CO

(E)-4-(3',4'-Dimethoxyphenyl)but-3-enyl
palmitate (18)

6 OH - 24
H 3CO

H 3CO

(E)-3-Hydroxy-1-(3',4'-dimethoxyphenyl)but-
1-ene (19)

7 OH - 24

H 3CO OH

H 3CO

(E)-2-Hydroxy-4-(3',4'-dimethoxyphenyl)but-
3-en-1-ol (20)

OCH3
8 - 24
H 3CO OH

H 3CO

(E)-2-Methoxy-4-(3',4'-dimethoxyphenyl)but-
3-en-1-ol (21)

9 H 3CO - 20

H 3CO

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

15
Arylbutanoids
Item Structure Biological Activity Ref.
10 - 24
H 3CO OH

HO

(E)-4-(4'-Hydroxy-3'-methoxyphenyl)but-2-
en-1-ol (23)

11 H 3CO OAc
- 24

HO

(E)-4-(4'-Hydroxy-3'-methoxyphenyl)but-3-
enyl acetate (24)

12 H 3CO
- 12

H 3CO OCH3

4-(2',4',5'-Trimethoxyphenyl)but-1,3-diene
(25)

13 H 3CO
- 11, 12

H 3CO OCH3

(E)-1-(2',4',5'-Trimethoxyphenyl)but-1-ene
(26)

Cyclobutyl Derivative
Item Structure Biological Activity Ref.

1 - 21
H3CO OCH3

H3CO OCH3

cis-1,2-bis[(E)-3",4"-
Dimethoxystyryl]cyclobutane (27)

16
Curcuminoid Derivatives
Item Structure Biological Activity Ref.
1 Anti-inflammatory, 2
O O
Anti-oxidative,
H3CO OCH3
Anti-tyrosinase,
HO OH Anti-microbial

Curcumin (10)

CH3 O O

2 Anti-oxidative, 22
Anti-inflammatory
H 3CO HO OH

OCH3 OCH3 OCH3

Cassumunin A (11)

OCH3 CH3 O O
3 Anti-oxidative, 22
Anti-inflammatory
H 3CO HO OH

OCH3 OCH3 OCH3

Cassumunin B (12)

OCH3
4 H3CO
Anti-oxidative, 22
Anti-inflammatory
O O

HO OH

OCH3 OCH3

Cassumunin C (13)
OCH3

OH
5 Anti-oxidative 23
OH

OCH3

O HO

H 3CO

OCH3

Cassumunarin A (14)

6 OCH3 Anti-oxidative 23
OH

OH

OCH3

O OH

H3CO

OCH3 Cassumunarin B (15)

17
Curcuminoid Derivatives
Item Structure Biological Activity Ref.
7 Anti-oxidative 23
OCH3

OH

OH

OCH3

H3CO O OH

H3CO

OCH3

Cassumunarin C (16)

Naphthoquinones
Item Structure Biological Activity Ref.

1 O - 7, 9, 11

OCH3

OCH3

OCH3

2-Methoxy-8-(3',4'-dimethoxyphenyl)-1,4-
naphthoquinone (28)

2 - 9, 11

OCH3

H3CO O

OCH3

OCH3

2-Methoxy-8-(2',4',5'-trimethoxyphenyl)-1,4-
naphthoquinone (29)

18
Cyclohexane Derivatives
Item Structure Biological Activity Ref.

OCH3
1 H
- 21

OCH3

OCH3

H3CO OCH3

trans-3-(2',4',5'-Trimethoxyphenyl)-4-
[(E)-3"',4"'-dimethoxystyryl]cyclohex-1-ene (30)

OCH3

2 H - 11
OCH3

OCH3

H3CO OCH3

cis-3-(2',4',5'-Trimethoxyphenyl)-4-[(E)-3"',4"'-
dimethoxystyryl]cyclohex-1-ene (31)

OCH3
3 - 11, 21
H

OCH3

OCH3

OCH3

trans-3-(3',4'-Dimethoxyphenyl]-4-(E)-
3"',4"'-dimethoxystyryl)cyclohex-1-ene (32)

H3CO OCH3
4 - 11
H

OCH3

OCH3

OCH3

trans-3-(3',4'-Dimethoxyphenyl)-4-(E)-
2"',4"',5"'-trimethoxystyryl]cyclohex-1-ene (33)

19
Cyclohexane Derivatives
Item Structure Biological Activity Ref.

H3CO OCH3
5 Anti-inflammatory 7, 10,
H
11, 27
OCH3

OCH3

H 3CO OCH3

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

OCH3

6 H Anti-inflammatory 7, 11,
OCH3 12, 27

OCH3

OCH3

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

H3CO OCH3
7 Anti-inflammatory 7, 11,
H
12, 21, 27
OCH3

OCH3

OCH3

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

20
 Literature Review:
Chemical Constituent Comparison of Plai Rhizomes20,26,32

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
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.

Table 3 Essential oil composition(%) of the different source rhizomes of Zingiber cassumunar
Roxb. (A) : Indonesia20; (B) : Thailand-Prachinburi;26 (C) : Thailand - TISTR32

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

CH3

1 = sabinene 2 = α-terpinene
OH
3 = γ-terpinene 4 = terpinen-4-ol
CH3 CH3 CH3 CH3
5 = DMPBD
sabinene

terpinen-4-ol

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

21
Safety 33
Dermal Safety
In 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 Safety
Acute 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.
Products
22
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.
Selected References

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.

23
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.htm
33. 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.

24
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