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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

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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., This Strategic Innovative Plai project is a


commonly known as Plai, is a Thai joint effort between the Innovation
herbal plant which has been Development Fund (IDF), the Postgraduate
exploited for medicinal purposes in Education and Research Program in
Thailand and Southeast Asia for Chemistry (PERCH), and leading herbal
centuries. Plai has long been companies, with the goal to export Plai
regarded by Thai massage therapists products to both local and global markets.
as one of those oils necessary to have
in their kit to combat joint and muscle The project could help restructure the
problems. The plant has been manufacturing and branding process in
proven to be extremely useful for the country as well as help in the promo-
human health and thus developed tion of Thai herbal plants to play a leading
into creams and massage oils for role in global markets.
relieving muscle pain. Furthermore,
it is well known that the essential oils IDF and PERCH have succeeded in the
from Plai have also been shown to development of a new “Plai” (Zingiber
cure acne, bruises, burnt skin, skin cassumunar Roxb.) through “collaborative
inflammation, muscle pain, insect innovation” between herbal companies.
bite, and asthmatic symptoms. They The project benefited from PERCH’s Plai
are even proven to cope with cough research which has developed the
and respiratory symptoms as well. substances having the trademark
PlaitanoidsTM that will be exported in the
Plai extracts exhibited anti-inflamma- forms of PlaitanoidsTM essential oil,
tory and anti-bacterial activities. A PlaitanoidsTM liquid extract, and
number of pure compounds isolated PlaitanoidsTM powder extract for make-up,
from the plants has been shown to shampoo, toothpaste, and spa industries.
possess anti-microbial, topical and With enough support, Plai and selected
oral anti-inflammatory, analgesic, pure compounds could be developed for
smooth muscle relaxant, anti-tyrosinase future pharmaceutical use.
and anti-oxidative activities. These
therapeutic indications and the Both IDF and PERCH aim to utilize the
reported ethnomedical uses make research to meet the market’s demands,
Plai an attractive candidate for the especially in the starting-up of new
development into cosmetics, spa companies on a research-based industry,
and skin beautification products. therefore leading up to innovation to
increase national competitiveness.

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Product Description

PlaitanoidsTM is the trademark of Terpinen-4-ol and sabinene are


ingredients containing groups of monoterpenes. They are major
compounds consisting of constituents in essential oil from
arylbutanoids (e.g. DMPBD) and their Zingiber cassumunar Roxb. The
dimers, curcuminoids and essential essential oil has been shown to exhibit
oils (e.g. terpinen-4-ol) derived from topical anti-inflammatory and anti- CH3
the rhizomes of Zingiber cassumunar microbial effects. DMPBD stands for
Roxb. with collaborative innovation (E)-1-(3', 4'-dimethoxyphenyl)butadiene
from IDF, PERCH and leading compa- found in essential oil and shown
nies based on the development of strong anti-inflammatory effect.
new products and technologies. 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)

PlaitanoidsTM

Essential Oil Liquid Extract H3CO

OCH3
Powder Extract (E)-1-(3',4'-Dimethoxyphenyl)butadiene = DMPBD
(3)

Steam Distillation Process Extraction and Spray Dry Process

Cleaning of the two-year-old rhizomes of Plai Steam distilled Plai


95% Alcohol
4 days

Thinly slice the rhizomes (about 1-2 mm) Separate the waste from the liquid

Evaporate at controlled temp./pressure


Put into tray

PlaitanoidsTM - Liquid Extract

Add additive
Heat at the temperature of 80°C for 6 hours
Spray dry at controlled temp.

PlaitanoidsTM - Essential Oil PlaitanoidsTM - Powder Extract

4
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

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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)

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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 DMPBD, was found to be an anti-
Roxb. is widely used in Thai traditional inflammatory agent twice as potent
medicine for topical treatment of as the reference drug diclofenac
sprains, contusions, joint inflamma- (ID50 = 3 vs 6 mg/paw, respectively).
tions, muscular pain, abscesses and
similar inflammation-related disorders. Interestingly, the five compounds
The topical anti-inflammatory activity isolated from hexane extract of the
of the five major components of the rhizome were all found to be equally
essential oil demonstrated that (E)-1- or more potent anti-inflammatory
(3’,4’-dimethoxyphenyl)butadiene agents than the reference drug
(DMPBD, 3), terpinen-4-ol (1) and α- diclofenac as shown in Table 1
pinene significantly inhibited edema whereas the potency of the
formation, whereas sabinene and γ- hexamethoxylated compound 7 was
terpinene were inactive up to 6 mg/ ca 20-30 times higher than that of
paw. The most active compound, 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

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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.

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Literature Review: Ethnopharmacological Use 31

Plai has long been regarded by Thai Applications:


massage therapists as one of those Aches and pains, inflammations, joint
oils necessary to have in their kit to problems, muscle spasms, sprains and
combat joint and muscle problems. strains, torn muscles and ligaments
Plai is in the same family as ginger but asthma, catarrh, chronic colds, colic,
has different properties and more constipation, diarrhea, fevers, flatu-
intense actions. The fresh rhizome of lence, heartburn, immune problems,
Plai is used in traditional Thai massage influenza, nausea, respiratory problems.
for muscle relaxant and joint pains.
A) Analgesic, anti-neuralgic, anti-
General Description: inflammatory, sprains and strains, torn
Essential oil of Plai is steam distilled muscles and ligaments: On inflamed
from the rhizome and has a pale joints, applying Plai, straight on; has
amber color. The scent is a cool, been found to ease off the pain for
green peppery one with a touch of a upwards of 18 hours, which is incred-
bite. Active chemicals: sabinene (25- ible since no other oil has been found
45%), γ-terpinene (5-10%), α-terpinene to change pain levels so far. On joints
(2-5%), terpinen-4-ol (25-45%), and that were inflamed due to injury, Plai
(E)-1-(3’,4’-dimethoxyphenyl)butadiene was best combined with oils such as
- in text as DMPBD (1-10%). black pepper and lemon or neroli,
Himalayan cedar and orange. These
Actions: combinations worked to take the
Analgesic, anti-neuralgic, anti-inflam- swelling down, calm the pain and
matory, anti-septic, anti-spasmodic, speed up the healing time consider-
anti-toxic, anti-viral, carminative, ably. Dilutions were one bottle of 10%
digestive, diuretic, febrifuge, laxative, concentration in a vegetable gel and
rubefacient, stimulant, stomachic, a small roller bottle with no dilution -
tonic, vermifuge. blends were all oils equal parts. The
analgesic topical preparation has
also been formulated and distributed
by the General Pharmaceutical
Organization (GPO).

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B) Post Operative Care: Plai, nutmeg D) Irritable Bowel Syndrome: For
and lemon have been used as a post digestive upsets, Plai along with black
operative surgical blend on a knee pepper, orange and tarragon has
surgery. These were of equal amounts been used to counter irritable bowel
in a 10% concentration in a roller syndrome. This blend was applied
bottle and applied above and below over the abdomen after each bowel
the surgical area. Tissue inflammation movement or anytime there were
and swelling was significantly lower any cramping or pain in the abdomi-
than in an area that had had the nal area. Within three applications, all
same surgery without the use of the problems calmed down.
Plai. With the Plai blend, no normal
narcotics were needed to control the E) Menstrual Cramps: Can be
post surgical pain. alleviated from a blend with Linden
Blossom, Plai, Marjoram and Orange.
C) Anti-histaminic: Plai, while being This was applied across the lower
of the ginger family, does not possess back and front abdomen every 15
the classic heat that is common to minutes until pain subsided. It was
the rhizomes. It has a cooling action found that after three applications all
on inflamed areas, be them joints cramps ceased and blood clots
and muscles or kidneys and lungs. diminished.
Clients have found that using Plai for
asthma along with tarragon (or F) Other Benefits: Dr Daniel Penoel
rosemary) and cypress causes the and Pierre Francome, Ph.D. in
attacks to greatly diminish in intensity. “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.

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Literature Review: Description of the Plant25

The rhizome part of the herb has a B) To 1 ml of solution A, add 0.2 ml of


yellow to green color with fleshy thick acetic anhydride-sulfuric acid TS: a reddish
texture containing multiple sessile brown color is produced.
tubers. Leaf stems 1 to 1.5 m tall.
Leaves distichous, oblong-lanceolate, C) To 1 ml of solution A, add 1 ml of boric
20 to 30 cm long and 2 to 8 cm wide, acid-methanol TS: an orange color is
pubescent below; ligule very short, produced.
bilobed, pubescent; sheath glabrous
or hairy. Inflorescences scapose; D) Carry out the test as described in the
peduncle 8 to 30 cm long, with “Thin-layer Chromatography”, using silica
pubescent sheaths. Spike ovoid- gel GF254 as the coating substance and a
ellipsoid; bracts greenish red, narrowly mixture of 70 volumes of hexane 30
obovate or rhomboid, 2.5 to 3.5 cm volumes of ethyl acetate as the mobile
long; bracteole shorter than bract, phase but allowing the solvent front to
ovate, 3-dentate. Calyx truncate, ascend 15 cm above the line of applica-
glabrous. Corolla tube ca. 2.5 cm tion. Apply separately to the plate, 2 µl of
long, pale yellow, dorsal lobe solution A and 3 µl of solution B. Prepare
cymbiform, lateral lobe linear- solution A by extracting 2.5 g of the
lanceolate. Labellum pale yellow, sample, in powder, with hexane until
suborbicular, apex emarginate, complete extraction is effected. Evapo-
lateral lobe ovate-oblong, append- rate the hexane extract to dryness and
age slightly longer than anther; dissolve the residue in 5 ml of chloroform.
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 3
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 2
A). Examine 1 ml of solution A under
ultraviolet light (366 nm): a greenish
yellow fluorescence is observed. Fig. 1 Zingiber cassumunar Roxb.
1. whole plant
2. rhizome
1 3. inflorescence

12
For solution B dissolve 1 mg of green, wine-red, violet, and dark
curcumin in 1 ml of chloroform. pink, respectively. Red spot due to
After removal of the plate from the curcumin (hRf value 10 to 13) and
chromatographic chamber, allow it other spots of different colors are
to dry in air and examine under observed (Table 2).
ultraviolet light (254 nm), marking the
quenching spots. The spots obtained Repeat the same procedure on
with solution A correspond in hRf another plate but spray with vanillin-
values to the spot number 2, 3, 5, 6, 7, sulfuric acid TS and heat at 110C for
and 8. Several spots of higher hRf 10 to 15 minutes; the spots due to
values are also observed (Table 2). those of number 2, 3, 5, 6, 7, and 8
Spray the plate with anisaldehyde- are olive-green, dark pink, purple,
sulfuric acid TS and heat at 110°C for blue-violet, red, and light orange,
10 to 15 minutes; spots due to those respectively. Red-brown spot due to
of numbers 2, 3, 5, 6, 7, and 8 in Table curcumin and other spots of different
2 are brown, carmine-red, olive 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

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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 light petroleum and about 46%, with
monoterpenes with sabinene and trans-1-(3’,4’-dimethoxyphenyl)but-1-
terpinen-4-ol as main constituents. ene, trans-1-(3’,4’-dimethoxyphenyl)
Sesquiterpenes accounted for a butadiene and trans-4-(3’,4’-
small part of the oil with dimethoxyphenyl)but-3-enyl acetate
sesquiphellandrene being the as the main constituents. The major
principal constituent. In addition to constituents in essential oil of Rhizome
these terpenes, the oil contains a of Z. cassumunar are shown in Table 3.
number of phenylbutanoids. The
essential oil obtained by It is indicated that the quantities of
hydrodistillation contained about 25% sabinene and terpinen-4-ol derived
of these phenylbutanoids whereas from Thailand’s rhizome are more
the oil obtained by extraction with 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 Chronic toxicity test during 12 months
plant itself and products in the in 192 Wistar rats showed that Plai
market derived from the oil for anti- forced fed 3.0 g/kg/day male rats
inflammatory, analgesic and anti- consumed less food than the control
microbial activities together with by 12% therefore less body weight
there is no report of the adverse gained. Hematological examination
effect for the external usage, This also suggested all groups were
makes Plai an attractive candidate normal. Biochemical examination
for the developing various externally indicated lower albumin but higher
useful products particularly essential SGOT and SGPT levels (p<0.05). There
oil and cosmetics. However a was a positive correlation between
comprehensive safety testing Plai’s concentration to the weight of
program is ongoing. liver and spleen. No pathological
changes in other organs were
Oral Safety observed except in the liver of Plai
Acute toxicity test of Plai revealed no treated rats with evidence of hepatic
evidence of toxicity in mice when cirrhosis and hepatocarcinogenesis.
given 10 g/kg body weight. The LD50 The detailed toxicological studies
of 50% alcohol extract administered including acute, subacute and
per os or subcutaneous was more mutagenic studies will be initiated
than 20 g/kg and intraperitoneal was with the DMPBD, a new pharmaco-
14.8 g/kg. logical agent for the treatment of
inflammatory disorders.

Products

22
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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